Crystal structure of tetra­kis­(μ2-(E)-2,4-di­bromo-6-{[2-(pyridin-2-yl)eth­yl]imino­meth­yl}phen­olato)trizinc bis­­(perchlorate) aceto­nitrile disolvate

Abstract

The title compound, [Zn 3 (C 14 H 11 Br 2 N 2 O) 4 ](ClO 4 ) 2 ·2CH 3 CN, crystallizes as a symmetrical trinuclear cation with all three metal atoms being located on a twofold rotation axis. It contains a tetrahedral Zn II atom that bridges two six-coordinate Zn II atoms. The complex contains N- and O-donor atoms of four tridentate 2,4-dibromo-6-{[2-(pyridin-2-yl)ethyl]iminomethyl}phenolate ligands. The ratio of Zn II atoms to ligands is 3:4. The two terminal Zn II cations adopt distorted octahedral geometries and the central Zn II cation adopts a distorted tetrahedral geometry. In the cation there are π–π interactions between the dibromophenyl rings, as well as halogen-bonding interactions between the dibromophenyl rings in the cation, which stabilize its conformation. In addition, there are C—H...O interactions between the anions and both the cations and solvent molecules as well as C—H...N interactions between the cation and solvent molecules. These interspecies interactions link the cations, anions and solvent molecules into a complex three-dimensional array

Full text

1380 https://doi.org/10.1107/S2056989018012100 Acta Cryst. (2018). E74, 1380–1383
research communications
Received 20 August 2018
Accepted 26 August 2018
Edited by J. Jasinsk, Keene State College, USA
Keywords: crystal structure; Schiff base ligand;
trinuclear Zn complex; halogen interactions.
CCDC reference:1863971
Supporting information:this article has
supporting information at journals.iucr.org/e
Crystal structure of tetrakis(l
2
-(E)-2,4-dibromo-6-
{[2-(pyridin-2-yl)ethyl]iminomethyl}phenolato)-
trizinc bis(perchlorate) acetonitrile disolvate
Ugochukwu Okeke, Raymond Otchere, Yilma Gultneh and Ray J. Butcher*
Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA. *Correspondence
e-mail: rbutcher99@yahoo.com
The title compound, [Zn
3
(C
14
H
11
Br
2
N
2
O)
4
](ClO
4
)
2
2CH
3
CN, crystallizes as a
symmetrical trinuclear cation with all three metal atoms being located on a
twofold rotation axis. It contains a tetrahedral Zn
II
atom that bridges two six-
coordinate Zn
II
atoms. The complex contains N- and O-donor atoms of four
tridentate 2,4-dibromo-6-{[2-(pyridin-2-yl)ethyl]iminomethyl}phenolate ligands.
The ratio of Zn
II
atoms to ligands is 3:4. The two terminal Zn
II
cations adopt
distorted octahedral geometries and the central Zn
II
cation adopts a distorted
tetrahedral geometry. In the cation there are –interactions between the
dibromophenyl rings, as well as halogen-bonding interactions between the
dibromophenyl rings in the cation, which stabilize its conformation. In addition,
there are C—HO interactions between the anions and both the cations and
solvent molecules as well as C—HN interactions between the cation and
solvent molecules. These interspecies interactions link the cations, anions and
solvent molecules into a complex three-dimensional array
1. Chemical context
Zinc(II)-derived metalloenzymes are among the most
common found in biology. Some enzymes containing zinc(II)
include carbonic anhydrase, carboxypeptidase, and phospha-
tase (Bertini et al., 1994; McCall et al., 2000). It is of interest to
study zinc(II) complexes derived from tridentate Schiff base
ligands because of the possibility of forming stable complex
structures. Zinc(II) plays a structural role not only in enzymes
but much progress has been made to incorporate it into metal–
organic frameworks for drug storage and release, lumines-
cence studies, and hydrogen-storage applications (An et al.,
2009; Bauer et al., 2007; Rosi et al., 2003).
Related complexes have been studied for their photo-
luminescent properties (Kundu et al., 2015; Chakraborty et al.,
ISSN 2056-9890

2013), drug therapeutic activity in DNA cleavage (Kumar et
al., 2011), and phosphatase mimetic activity (Kumar et al.,
2011; Gultneh et al., 1999). The coordination environment of
the title compound, illustrated in Fig. 1, has been observed in
zinc(II) complexes with tridentate N,N,Oligands (Hens &
Rajak, 2015; Kim et al., 2015). Transition metal complexes of
the related tridentate ligand, 1,3(2-pyridyliminometh-
yl)phenylenediamine, have been shown to form a variety of
interesting complex structures (Kundu et al., 2015; Kumar et
al., 2011; Bluhm et al., 2003; Souza et al., 2011; Sanyal et al.,
2014; Okeke et al., 2017a,b; Okeke et al., 2018). The presence
of a substituent on the aromatic group may change the
geometry, coordination number, and consequently the reac-
tivity of the resulting complexes especially because of its
location on the aromatic ring that coordinates to the metal ion
through the phenoxide oxygen atom.
In a continuation of our model studies of zinc complexes as
Lewis acid center in zinc-containing hydrolytic enzymes
(Gultneh et al., 1996; Gultneh et al., 1999; Okeke et al.,
2017a,b) we report the structure of the title compound. This
trinuclear zinc(II) complex has a 3:4 metal ion-to-ligand ratio.
Since the title compound lies on a crystallographic twofold
axis, the three zinc(II) ions form an angle of 180
o
and thus are
strictly linear. The central zinc atom is four coordinate and
may serve as a suitable complex for various reactions because
the Zn
II
Lewis acid metal center contains vacant coordination
sites for coordination to a nucleophile.
2. Structural commentary
The crystal structure of the title compound,
[Zn
3
(C
14
H
11
Br
2
N
2
O)
4
](ClO
4
)
2
2CH
3
CN, 1, contains a
complex cation as well as perchlorate anions and acetonitrile
solvent molecules and thus has an overall stoichiometry of
[Zn
3
(L)
4
](ClO
4
)
2
.
2CH
3
CN where Lis 2,4-dibromo-6-{[(2-
(pyridin-2-yl)ethyl]iminomethyl}phenolate. The compound
crystallizes in the monoclinic space group C2/cand the cation
consists of the four equivalent Lligands, uniformly coordin-
ated to three Zn
II
cations.
The trinuclear complex cation, [Zn
3
(L)
4
]
2+
, lies on a crys-
tallographic twofold axis (Fig. 1). The zinc(II) ions contain
varying coordination spheres. Zn1 and Zn3 adopt O
2
N
4
coordination spheres while the central zinc atom Zn2 adopts
an O
4
coordination sphere with a distorted tetrahedral
geometry with O—Zn—O bond angles ranging from
88.95 (11) to 120.11 (8)and Zn—O bond lengths of
1.9512 (19) and 1.9602 (19) A
˚. For the six-coordinate terminal
zinc atoms, as is usual for complexes containing both Schiff
base imine and pyridine N donors, the former form shorter
bonds [Zn1—N1 = 2.122 (2) A
˚and Zn3—-N3 = 2.067 (2) A
˚]
while the latter form longer bonds [Zn1—N2 = 2.148 (2) A
˚
and Zn3—N4 = 2.177 (2) A
˚] to zinc. The metrical parameters
involving the bridging phenolate O donors are significantly
different. The bonds to the central Zn2 are considerably
shorter than those to the terminal Zn1 and Zn3 [O1—Zn1 =
2.194 (2) A
˚; O2—Zn3 = 2.266 (2) A
˚; O1—Zn2 = 1.960 (2) A
˚;
O2—Zn2 = 1.951 (2) A
˚] and the bridging angles are Zn1—
O1—Zn2 = 96.78 (8)and Zn2—O2—Zn3 = 93.73 (8).The
distortion from an octahedral geometry can be seen from the
cis and trans angles which range from 77.49 (10) to 98.19 (9)
and 160.47 (13) to 173.41 (12), respectively. Since all three Zn
atoms lie on the twofold axis, the Zn1—Zn2—Zn3 bond angle
is exactly 180. These metrical parameters are similar to those
found in the most closely similar complex (Kim et al., 2015)
where Zn—O distances for the terminal Zn atoms range from
2.126 (3) to 2.155 (4) A
˚while those for the central Zn atom
range from 1.945 (3) to 1.965 (4) A
˚with Zn—O—Zn bridging
angles ranging from 97.3 (1) to 98.7 (1). The Zn—N
imine
and
Zn—N
py
bond lengths range from 2.077 (4) to 2.117 (4) A
˚and
2.140 (4) to 2.176 (4) A
˚, respectively. In this complex there is
no crystallographically imposed symmetry; however, the Zn—
Zn—Zn bond angle is still close to 180 at 172.51 (3).
research communications
Acta Cryst. (2018). E74, 1380–1383 Okeke et al. [Zn
3
(C
14
H
11
Br
2
N
2
O)
4
](ClO
4
)
2
2C
2
H
3
N1381
Table 1
Hydrogen-bond geometry (A
˚,).
D—HAD—H HADAD—HA
C9—H9ABr1
i
0.99 2.92 3.854 (3) 157
C9—H9AO1
i
0.99 2.60 3.317 (4) 129
C21—H21AO14 0.95 2.57 3.080 (4) 114
C22—H22AO14 0.99 2.58 3.099 (4) 113
C22—H22BBr4
ii
0.99 2.96 3.664 (3) 129
C23—H23AO12
iii
0.99 2.58 3.427 (4) 144
C28—H28AN3
i
0.95 2.60 3.236 (4) 125
C2S—H2S1O11 0.98 2.60 3.556 (4) 165
C2S—H2S2Br2 0.98 3.02 3.935 (4) 157
C2S—H2S2Br4 0.98 3.04 3.561 (3) 115
Symmetry codes: (i) xþ1;y;zþ1
2; (ii) x;yþ1;z1
2; (iii) xþ1
2;yþ3
2;z.
Figure 1
Diagram of the cation, tetrakis(
2
-(E)-2,4-dibromo-6-({[2-(pyridin-2-
yl)ethyl]iminomethyl}phenolato)trizinc, showing the parallel dibromo-
phenyl rings. Atomic displacement parameters are at the 30% probability
level.

3. Supramolecular features
In the cation there are –interactions between the di-
bromophenyl rings [centroid–centroid distance = 3.602 (2) A
˚;
CgIperp = 3.344 (1) A
˚; slippage = 1.319 (2) A
˚] as well as
halogen-bonding interactions [BrBr 3.6123 (5) A
˚;C—
BrBr, 129.08 (9)] between the dibromophenyl rings in the
cation, which stabilize its conformation. In addition there C–
HO interactions between the anions and both the cations
and solvent molecules as well as C—HN interactions
between the cation and solvent molecules (Table 1). These
interspecies interactions link the cations, anions and solvent
molecules into a complex three-dimensional array as shown in
Fig. 2.
4. Database survey
A search of the Cambridge Structural Database for complexes
of zinc coordinated to (E)-2-({[2-(pyridin-2-yl)ethyl]imino}-
methyl)phenolato type ligands gave 26 hits of which only one
was similar to the title compound in that it contained a
trinuclear Zn complex where this ligand was acting as a
bridging group to the central Zn atom (Diop et al., 2014) .
However, in this case each terminal Zn complex only provided
one bridging O atom and the coordination sphere of the
central Zn was hexacoordinate with six O-atom donors in
contrast to the title compound where the central Zn is four–
coordinate with the terminal Zn complexes provided two
bridging atoms through their phenolic O atoms. A search for
structures containing three zinc atoms with the central zinc
atom in an 
2
-O
4
environment and with the terminal zinc
atoms coordinated to Schiff base derivatives gave four hits
[MAYVEQ, Quilter et al., 2017; GOWGUW, Hens & Rajak,
2015; HUQVUL, Akine et al., 2009; KURPAL, Kim et al.,
2015] of which that using the ligand, 2-methyl-6-{[(pyridin-2-
ylmethyl)imino]methyl}phenol in the presence of NH
4
PF
6
resulted in a closely related trinuclear zinc complex with the
central Zn atom four-coordinate with only O-atom donors
from the bridging phenolate ligands (Kim et al., 2015). The
major differences between this complex and 1is a –CH
2
– link
between the imine N and pyridine ring in the former instead of
a –CH
2
-CH
2
– link in the latter, and different substituents on
the phenyl ring.
5. Synthesis and crystallization
2-(2-Pyridyl)ethylamine (0.3023 g, 2.474 mmol) was dissolved
in 50 mL of methanol. 3,5-Dibromosalicylaldehyde (0.6927 g,
2.474 mmol) was added to the solution and the mixture was
refluxed for 5 h. The zinc(II) complex was prepared by
reacting the ligand in 50 ml of methanol with Zn(ClO
4
)
2
6H
2
O
(1.3821 g, 3.712 mmol) with no added base. The mixture was
stirred at room temperature overnight. The methanol was
removed by rotary evaporation. The product was crystallized
by slow evaporation of a solution in acetonitrile giving pale-
yellow to colorless crystals.
1382 Okeke et al. [Zn
3
(C
14
H
11
Br
2
N
2
O)
4
](ClO
4
)
2
2C
2
H
3
NActa Cryst. (2018). E74, 1380–1383
research communications
Figure 2
Packing diagram viewed along the baxis showing the extensive C—HO, C —HN, and C—HBr interactions (shown as dashed lines) linking the
cations, anions, and solvent molecules into a complex three-dimensional array.

6. Refinement
Crystal data, data collection and structure refinement details
are summarized in Table 2. All hydrogen atoms were refined
using a riding model with C—H distances of 0.95 to 0.99 A
˚and
U
iso
(H) = 1.2U
eq
(C) or 1.5U
eq
(CH
3
).
Acknowledgements
UO and RO wish to acknowledge the College of Arts &
Sciences at Howard University for a Teaching Assistantship.
Funding information
RJB is grateful for the NSF award 1205608, Partnership for
Reduced Dimensional Materials for partial funding of this
research as well as the Howard University Nanoscience
Facility access to liquid nitrogen. RJB acknowledges the NSF
MRI program (grant No. CHE-0619278) for funds to purchase
an X-ray.
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research communications
Acta Cryst. (2018). E74, 1380–1383 Okeke et al. [Zn
3
(C
14
H
11
Br
2
N
2
O)
4
](ClO
4
)
2
2C
2
H
3
N1383
Table 2
Experimental details.
Crystal data
Chemical formula [Zn
3
(C
14
H
11
Br
2
N
2
O)
4
](ClO
4
)
2
-
2C
2
H
3
N
M
r
2009.39
Crystal system, space group Monoclinic, C2/c
Temperature (K) 100
a,b,c(A
˚) 30.797 (3), 13.8527 (12), 21.135 (3)
() 132.857 (1)
V(A
˚
3
) 6609.6 (13)
Z4
Radiation type Mo K
(mm
1
) 6.07
Crystal size (mm) 0.35 0.31 0.24
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Sheldrick,
1996)
T
min
,T
max
0.585, 0.746
No. of measured, independent and
observed [I>2(I)] reflections
23422, 7310, 5978
R
int
0.042
(sin /)
max
(A
˚
1
) 0.643
Refinement
R[F
2
>2(F
2
)], wR(F
2
), S0.028, 0.066, 1.01
No. of reflections 7310
No. of parameters 431
H-atom treatment H-atom parameters constrained

max
,
min
(e A
˚
3
) 0.52, 0.56
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXT (Sheldrick, 2015a),
SHELXL2018 (Sheldrick, 2015b) and SHELXTL (Sheldrick, 2008).

supporting information
sup-1
Acta Cryst. (2018). E74, 1380-1383
supporting information
Acta Cryst. (2018). E74, 1380-1383 [https://doi.org/10.1107/S2056989018012100]
Crystal structure of tetrakis(µ2-(E)-2,4-dibromo-6-{[2-(pyridin-2-yl)ethyl]imino-
methyl}phenolato)trizinc bis(perchlorate) acetonitrile disolvate
Ugochukwu Okeke, Raymond Otchere, Yilma Gultneh and Ray J. Butcher
Computing details
Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014);
program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018
(Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication:
SHELXTL (Sheldrick, 2008).
Tetrakis(µ2-(E)-2,4-dibromo-6-{[2-(pyridin-2-yl)ethyl]iminomethyl}phenolato)trizinc bis(perchlorate) acetonitrile
disolvate
Crystal data
[Zn3(C14H11Br2N2O)4](ClO4)2·2C2H3N
Mr = 2009.39
Monoclinic, C2/c
a = 30.797 (3) Å
b = 13.8527 (12) Å
c = 21.135 (3) Å
β = 132.857 (1)°
V = 6609.6 (13) Å3
Z = 4
F(000) = 3920
Dx = 2.019 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 6020 reflections
θ = 2.5–27.1°
µ = 6.07 mm−1
T = 100 K
Chunk, colorless
0.35 × 0.31 × 0.24 mm
Data collection
Bruker APEXII CCD
diffractometer
φ and ω scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Tmin = 0.585, Tmax = 0.746
23422 measured reflections
7310 independent reflections
5978 reflections with I > 2σ(I)
Rint = 0.042
θmax = 27.2°, θmin = 1.7°
h = −37→39
k = −17→17
l = −27→25
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.028
wR(F2) = 0.066
S = 1.01
7310 reflections
431 parameters
0 restraints
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0285P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.52 e Å−3
Δρmin = −0.56 e Å−3

supporting information
sup-2
Acta Cryst. (2018). E74, 1380-1383
Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance
matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate
(isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzU
iso*/Ueq
Zn1 0.500000 0.14227 (3) 0.250000 0.01098 (11)
Zn2 0.500000 0.36678 (3) 0.250000 0.00984 (10)
Zn3 0.500000 0.58950 (3) 0.250000 0.00943 (10)
Br1 0.32810 (2) 0.35929 (2) 0.03320 (2) 0.01421 (7)
Br2 0.23309 (2) 0.24841 (2) 0.17654 (2) 0.01768 (8)
Br3 0.57097 (2) 0.36780 (2) 0.49927 (2) 0.01481 (7)
Br4 0.34475 (2) 0.39606 (2) 0.38605 (2) 0.01633 (8)
O1 0.43973 (8) 0.26581 (13) 0.19910 (12) 0.0116 (4)
O2 0.50660 (8) 0.46259 (13) 0.32385 (12) 0.0105 (4)
N1 0.49899 (10) 0.15108 (16) 0.34924 (15) 0.0120 (5)
N2 0.57350 (10) 0.04396 (16) 0.32655 (16) 0.0128 (5)
N3 0.41056 (10) 0.56419 (16) 0.17387 (14) 0.0100 (5)
N4 0.48785 (10) 0.69446 (17) 0.16238 (15) 0.0120 (5)
C1 0.39443 (13) 0.26316 (19) 0.19470 (18) 0.0115 (6)
C2 0.33828 (12) 0.3003 (2) 0.12332 (18) 0.0125 (6)
C3 0.29034 (12) 0.2968 (2) 0.11669 (18) 0.0125 (6)
H3A 0.252883 0.321421 0.066928 0.015*
C4 0.29783 (13) 0.2567 (2) 0.18389 (19) 0.0134 (6)
C5 0.35244 (12) 0.2226 (2) 0.25680 (19) 0.0133 (6)
H5A 0.357743 0.198681 0.303803 0.016*
C6 0.40025 (13) 0.2231 (2) 0.26161 (19) 0.0125 (6)
C7 0.45614 (12) 0.1826 (2) 0.34060 (19) 0.0130 (6)
H7A 0.460954 0.179563 0.389986 0.016*
C8 0.54796 (13) 0.1062 (2) 0.43393 (19) 0.0165 (7)
H8A 0.539244 0.036827 0.431509 0.020*
H8B 0.550395 0.136791 0.478608 0.020*
C9 0.60749 (13) 0.1166 (2) 0.45962 (19) 0.0161 (7)
H9A 0.611367 0.183690 0.447945 0.019*
H9B 0.639425 0.105514 0.522545 0.019*
C10 0.61651 (13) 0.0488 (2) 0.41373 (19) 0.0146 (6)
C11 0.66718 (13) −0.0086 (2) 0.45956 (19) 0.0172 (7)
H11A 0.696529 −0.005330 0.520794 0.021*
C12 0.67487 (14) −0.0699 (2) 0.4164 (2) 0.0200 (7)
H12A 0.709631 −0.108159 0.447257 0.024*
C13 0.63092 (14) −0.0745 (2) 0.3273 (2) 0.0191 (7)
H13A 0.634965 −0.115895 0.295756 0.023*
C14 0.58105 (13) −0.0179 (2) 0.2852 (2) 0.0176 (7)
H14A 0.550541 −0.022584 0.224201 0.021*
C15 0.47154 (12) 0.45477 (19) 0.33930 (18) 0.0104 (6)

supporting information
sup-3
Acta Cryst. (2018). E74, 1380-1383
C16 0.49187 (12) 0.4129 (2) 0.41645 (18) 0.0112 (6)
C17 0.45533 (12) 0.3990 (2) 0.43196 (18) 0.0131 (6)
H17A 0.470451 0.370516 0.484520 0.016*
C18 0.39659 (13) 0.4268 (2) 0.37030 (19) 0.0123 (6)
C19 0.37482 (13) 0.4694 (2) 0.29449 (18) 0.0130 (6)
H19A 0.334411 0.488362 0.252538 0.016*
C20 0.41171 (12) 0.4850 (2) 0.27879 (18) 0.0111 (6)
C21 0.38403 (12) 0.52587 (19) 0.19498 (18) 0.0098 (6)
H21A 0.342005 0.523861 0.151561 0.012*
C22 0.37350 (12) 0.6000 (2) 0.08515 (18) 0.0124 (6)
H22A 0.331359 0.586806 0.053059 0.015*
H22B 0.383766 0.565070 0.055952 0.015*
C23 0.38206 (13) 0.7089 (2) 0.08335 (19) 0.0145 (6)
H23A 0.346350 0.734522 0.026604 0.017*
H23B 0.384761 0.740418 0.127954 0.017*
C24 0.43538 (13) 0.7373 (2) 0.09813 (19) 0.0129 (6)
C25 0.42998 (13) 0.8065 (2) 0.04501 (19) 0.0148 (6)
H25A 0.392689 0.835759 −0.000033 0.018*
C26 0.47876 (13) 0.8322 (2) 0.05796 (19) 0.0153 (6)
H26A 0.475620 0.879928 0.022729 0.018*
C27 0.53280 (13) 0.7871 (2) 0.12365 (19) 0.0156 (6)
H27A 0.567076 0.802490 0.133565 0.019*
C28 0.53512 (13) 0.7196 (2) 0.17379 (19) 0.0145 (6)
H28A 0.571971 0.689164 0.218806 0.017*
Cl1 0.27556 (3) 0.71818 (5) 0.15347 (5) 0.01814 (16)
O11 0.23291 (11) 0.65110 (17) 0.13573 (16) 0.0326 (6)
O12 0.25024 (10) 0.81314 (16) 0.12595 (16) 0.0285 (6)
O13 0.32715 (10) 0.7195 (2) 0.24425 (15) 0.0384 (7)
O14 0.29229 (12) 0.69039 (18) 0.10698 (18) 0.0383 (7)
N1S 0.08476 (12) 0.49951 (19) 0.11043 (17) 0.0250 (7)
C1S 0.13487 (15) 0.4960 (2) 0.1626 (2) 0.0208 (7)
C2S 0.19918 (14) 0.4933 (3) 0.2300 (2) 0.0327 (9)
H2S1 0.215955 0.538085 0.215527 0.049*
H2S2 0.213104 0.427731 0.234893 0.049*
H2S3 0.211812 0.512395 0.285114 0.049*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Zn1 0.0127 (2) 0.0081 (2) 0.0110 (2) 0.000 0.0076 (2) 0.000
Zn2 0.0117 (2) 0.0072 (2) 0.0126 (2) 0.000 0.0091 (2) 0.000
Zn3 0.0097 (2) 0.0082 (2) 0.0103 (2) 0.000 0.0068 (2) 0.000
Br1 0.01578 (15) 0.01304 (15) 0.01356 (14) −0.00108 (12) 0.00988 (13) 0.00087 (12)
Br2 0.01496 (15) 0.02397 (17) 0.01785 (15) −0.00013 (12) 0.01263 (14) −0.00039 (13)
Br3 0.01271 (14) 0.01568 (15) 0.01417 (15) 0.00158 (12) 0.00840 (13) 0.00163 (12)
Br4 0.01600 (15) 0.02204 (16) 0.01645 (15) −0.00221 (12) 0.01321 (13) 0.00029 (13)
O1 0.0112 (10) 0.0095 (10) 0.0142 (10) −0.0017 (8) 0.0087 (9) −0.0025 (8)
O2 0.0122 (10) 0.0106 (10) 0.0126 (10) −0.0008 (8) 0.0100 (9) −0.0022 (8)

supporting information
sup-4
Acta Cryst. (2018). E74, 1380-1383
N1 0.0125 (12) 0.0092 (12) 0.0115 (12) −0.0006 (10) 0.0070 (11) 0.0016 (10)
N2 0.0160 (12) 0.0068 (12) 0.0155 (12) −0.0018 (10) 0.0107 (11) 0.0007 (10)
N3 0.0119 (12) 0.0090 (12) 0.0100 (11) 0.0011 (10) 0.0079 (10) −0.0010 (10)
N4 0.0135 (12) 0.0096 (12) 0.0134 (12) −0.0011 (10) 0.0093 (11) −0.0005 (10)
C1 0.0139 (14) 0.0057 (13) 0.0140 (14) −0.0007 (11) 0.0092 (13) −0.0025 (11)
C2 0.0162 (15) 0.0079 (14) 0.0133 (14) −0.0048 (12) 0.0099 (13) −0.0029 (12)
C3 0.0129 (14) 0.0083 (14) 0.0144 (14) 0.0008 (11) 0.0086 (13) 0.0003 (12)
C4 0.0135 (14) 0.0126 (15) 0.0174 (15) −0.0033 (12) 0.0118 (13) −0.0028 (12)
C5 0.0151 (15) 0.0103 (14) 0.0148 (15) −0.0023 (12) 0.0104 (13) −0.0018 (12)
C6 0.0151 (15) 0.0059 (13) 0.0157 (15) −0.0012 (11) 0.0102 (13) −0.0020 (12)
C7 0.0167 (15) 0.0074 (14) 0.0145 (14) −0.0052 (12) 0.0104 (13) −0.0035 (12)
C8 0.0195 (16) 0.0128 (15) 0.0157 (15) 0.0013 (13) 0.0113 (14) 0.0029 (13)
C9 0.0156 (15) 0.0131 (15) 0.0122 (14) 0.0005 (12) 0.0066 (13) 0.0007 (12)
C10 0.0164 (15) 0.0113 (15) 0.0148 (15) −0.0024 (12) 0.0100 (13) 0.0008 (12)
C11 0.0128 (15) 0.0170 (16) 0.0136 (15) −0.0003 (12) 0.0057 (13) 0.0023 (13)
C12 0.0181 (16) 0.0130 (15) 0.0246 (17) 0.0033 (13) 0.0127 (15) 0.0041 (14)
C13 0.0238 (17) 0.0125 (15) 0.0221 (17) 0.0014 (13) 0.0160 (15) 0.0009 (13)
C14 0.0192 (16) 0.0120 (15) 0.0152 (15) −0.0014 (13) 0.0092 (14) 0.0006 (13)
C15 0.0143 (14) 0.0046 (13) 0.0163 (14) −0.0018 (11) 0.0120 (13) −0.0037 (11)
C16 0.0096 (14) 0.0110 (14) 0.0113 (14) 0.0008 (11) 0.0065 (12) −0.0020 (12)
C17 0.0175 (15) 0.0096 (14) 0.0119 (14) −0.0025 (12) 0.0099 (13) −0.0015 (12)
C18 0.0137 (14) 0.0132 (15) 0.0168 (15) −0.0026 (12) 0.0130 (13) −0.0030 (12)
C19 0.0137 (14) 0.0136 (15) 0.0110 (14) −0.0001 (12) 0.0082 (12) −0.0038 (12)
C20 0.0128 (14) 0.0082 (14) 0.0132 (14) −0.0014 (11) 0.0092 (12) −0.0014 (12)
C21 0.0080 (13) 0.0091 (14) 0.0114 (13) 0.0008 (11) 0.0062 (12) −0.0020 (11)
C22 0.0109 (14) 0.0154 (15) 0.0110 (14) −0.0017 (12) 0.0074 (12) −0.0013 (12)
C23 0.0154 (15) 0.0120 (15) 0.0146 (15) 0.0041 (12) 0.0096 (13) 0.0054 (12)
C24 0.0170 (15) 0.0085 (14) 0.0142 (14) −0.0024 (12) 0.0110 (13) −0.0033 (12)
C25 0.0168 (15) 0.0101 (14) 0.0154 (15) 0.0027 (12) 0.0102 (13) 0.0034 (12)
C26 0.0242 (16) 0.0113 (14) 0.0147 (15) −0.0012 (13) 0.0150 (14) 0.0003 (12)
C27 0.0181 (15) 0.0147 (15) 0.0171 (15) −0.0045 (13) 0.0133 (14) −0.0016 (13)
C28 0.0147 (15) 0.0129 (15) 0.0150 (15) 0.0011 (12) 0.0097 (13) 0.0002 (12)
Cl1 0.0169 (4) 0.0209 (4) 0.0201 (4) 0.0014 (3) 0.0140 (3) −0.0002 (3)
O11 0.0386 (15) 0.0322 (14) 0.0322 (14) −0.0188 (12) 0.0262 (13) −0.0101 (12)
O12 0.0306 (13) 0.0187 (12) 0.0425 (15) 0.0058 (10) 0.0273 (13) −0.0003 (11)
O13 0.0182 (13) 0.0659 (19) 0.0193 (13) −0.0026 (13) 0.0080 (11) 0.0072 (13)
O14 0.0582 (17) 0.0329 (15) 0.0568 (18) 0.0171 (13) 0.0521 (16) 0.0089 (13)
N1S 0.0239 (16) 0.0186 (15) 0.0221 (15) −0.0001 (12) 0.0115 (14) −0.0009 (12)
C1S 0.0312 (19) 0.0096 (15) 0.0246 (18) 0.0020 (14) 0.0202 (17) 0.0011 (13)
C2S 0.0239 (19) 0.0217 (18) 0.042 (2) 0.0014 (15) 0.0182 (18) 0.0031 (17)
Geometric parameters (Å, º)
Zn1—N1i2.122 (2) C9—C10 1.505 (4)
Zn1—N1 2.122 (2) C9—H9A 0.9900
Zn1—N2i2.148 (2) C9—H9B 0.9900
Zn1—N2 2.148 (2) C10—C11 1.396 (4)
Zn1—O1i2.1943 (19) C11—C12 1.379 (4)

supporting information
sup-5
Acta Cryst. (2018). E74, 1380-1383
Zn1—O1 2.1943 (19) C11—H11A 0.9500
Zn1—Zn2 3.1100 (7) C12—C13 1.384 (4)
Zn2—O2 1.9512 (19) C12—H12A 0.9500
Zn2—O2i1.9512 (19) C13—C14 1.381 (4)
Zn2—O1 1.9602 (19) C13—H13A 0.9500
Zn2—O1i1.9602 (19) C14—H14A 0.9500
Zn2—Zn3 3.0852 (7) C15—C16 1.414 (4)
Zn3—N3 2.067 (2) C15—C20 1.415 (4)
Zn3—N3i2.067 (2) C16—C17 1.383 (4)
Zn3—N4i2.177 (2) C17—C18 1.383 (4)
Zn3—N4 2.177 (2) C17—H17A 0.9500
Zn3—O2 2.2664 (19) C18—C19 1.380 (4)
Zn3—O2i2.2664 (19) C19—C20 1.400 (4)
Br1—C2 1.892 (3) C19—H19A 0.9500
Br2—C4 1.895 (3) C20—C21 1.460 (4)
Br3—C16 1.894 (3) C21—H21A 0.9500
Br4—C18 1.888 (3) C22—C23 1.536 (4)
O1—C1 1.334 (3) C22—H22A 0.9900
O2—C15 1.328 (3) C22—H22B 0.9900
N1—C7 1.280 (4) C23—C24 1.500 (4)
N1—C8 1.481 (4) C23—H23A 0.9900
N2—C14 1.351 (4) C23—H23B 0.9900
N2—C10 1.354 (4) C24—C25 1.398 (4)
N3—C21 1.282 (4) C25—C26 1.378 (4)
N3—C22 1.467 (3) C25—H25A 0.9500
N4—C28 1.350 (4) C26—C27 1.395 (4)
N4—C24 1.350 (4) C26—H26A 0.9500
C1—C2 1.408 (4) C27—C28 1.378 (4)
C1—C6 1.412 (4) C27—H27A 0.9500
C2—C3 1.386 (4) C28—H28A 0.9500
C3—C4 1.390 (4) Cl1—O13 1.435 (2)
C3—H3A 0.9500 Cl1—O11 1.435 (2)
C4—C5 1.379 (4) Cl1—O12 1.435 (2)
C5—C6 1.405 (4) Cl1—O14 1.438 (2)
C5—H5A 0.9500 N1S—C1S 1.134 (4)
C6—C7 1.468 (4) C1S—C2S 1.454 (5)
C7—H7A 0.9500 C2S—H2S1 0.9800
C8—C9 1.524 (4) C2S—H2S2 0.9800
C8—H8A 0.9900 C2S—H2S3 0.9800
C8—H8B 0.9900
N1i—Zn1—N1 173.41 (12) C1—C6—C7 122.7 (3)
N1i—Zn1—N2i90.48 (9) N1—C7—C6 126.2 (3)
N1—Zn1—N2i93.70 (9) N1—C7—H7A 116.9
N1i—Zn1—N2 93.70 (9) C6—C7—H7A 116.9
N1—Zn1—N2 90.48 (9) N1—C8—C9 112.4 (2)
N2i—Zn1—N2 101.31 (12) N1—C8—H8A 109.1
N1i—Zn1—O1i82.16 (8) C9—C8—H8A 109.1

supporting information
sup-6
Acta Cryst. (2018). E74, 1380-1383
N1—Zn1—O1i92.68 (8) N1—C8—H8B 109.1
N2i—Zn1—O1i166.02 (8) C9—C8—H8B 109.1
N2—Zn1—O1i91.06 (8) H8A—C8—H8B 107.9
N1i—Zn1—O1 92.68 (8) C10—C9—C8 114.6 (2)
N1—Zn1—O1 82.16 (8) C10—C9—H9A 108.6
N2i—Zn1—O1 91.06 (8) C8—C9—H9A 108.6
N2—Zn1—O1 166.02 (8) C10—C9—H9B 108.6
O1i—Zn1—O1 77.49 (10) C8—C9—H9B 108.6
N1i—Zn1—Zn2 86.70 (6) H9A—C9—H9B 107.6
N1—Zn1—Zn2 86.70 (6) N2—C10—C11 120.9 (3)
N2i—Zn1—Zn2 129.35 (6) N2—C10—C9 118.0 (3)
N2—Zn1—Zn2 129.34 (6) C11—C10—C9 121.1 (3)
O1i—Zn1—Zn2 38.75 (5) C12—C11—C10 120.4 (3)
O1—Zn1—Zn2 38.75 (5) C12—C11—H11A 119.8
O2—Zn2—O2i94.29 (11) C10—C11—H11A 119.8
O2—Zn2—O1 117.97 (8) C11—C12—C13 118.6 (3)
O2i—Zn2—O1 120.11 (8) C11—C12—H12A 120.7
O2—Zn2—O1i120.11 (8) C13—C12—H12A 120.7
O2i—Zn2—O1i117.96 (8) C14—C13—C12 118.7 (3)
O1—Zn2—O1i88.95 (11) C14—C13—H13A 120.7
O2—Zn2—Zn3 47.14 (6) C12—C13—H13A 120.7
O2i—Zn2—Zn3 47.14 (6) N2—C14—C13 123.3 (3)
O1—Zn2—Zn3 135.52 (6) N2—C14—H14A 118.4
O1i—Zn2—Zn3 135.52 (6) C13—C14—H14A 118.4
O2—Zn2—Zn1 132.86 (6) O2—C15—C16 121.4 (2)
O2i—Zn2—Zn1 132.86 (6) O2—C15—C20 122.1 (3)
O1—Zn2—Zn1 44.48 (6) C16—C15—C20 116.5 (3)
O1i—Zn2—Zn1 44.48 (6) C17—C16—C15 122.5 (3)
Zn3—Zn2—Zn1 180.0 C17—C16—Br3 118.5 (2)
N3—Zn3—N3i160.47 (13) C15—C16—Br3 118.9 (2)
N3—Zn3—N4i98.19 (9) C16—C17—C18 119.4 (3)
N3i—Zn3—N4i94.83 (9) C16—C17—H17A 120.3
N3—Zn3—N4 94.83 (9) C18—C17—H17A 120.3
N3i—Zn3—N4 98.19 (9) C19—C18—C17 120.3 (3)
N4i—Zn3—N4 96.20 (13) C19—C18—Br4 120.0 (2)
N3—Zn3—O2 81.50 (8) C17—C18—Br4 119.5 (2)
N3i—Zn3—O2 83.37 (8) C18—C19—C20 120.6 (3)
N4i—Zn3—O2 92.83 (8) C18—C19—H19A 119.7
N4—Zn3—O2 170.67 (8) C20—C19—H19A 119.7
N3—Zn3—O2i83.37 (8) C19—C20—C15 120.6 (3)
N3i—Zn3—O2i81.50 (8) C19—C20—C21 116.7 (3)
N4i—Zn3—O2i170.67 (8) C15—C20—C21 122.6 (3)
N4—Zn3—O2i92.83 (8) N3—C21—C20 126.8 (3)
O2—Zn3—O2i78.27 (10) N3—C21—H21A 116.6
N3—Zn3—Zn2 80.23 (6) C20—C21—H21A 116.6
N3i—Zn3—Zn2 80.23 (6) N3—C22—C23 111.5 (2)
N4i—Zn3—Zn2 131.90 (6) N3—C22—H22A 109.3
N4—Zn3—Zn2 131.90 (6) C23—C22—H22A 109.3

supporting information
sup-7
Acta Cryst. (2018). E74, 1380-1383
O2—Zn3—Zn2 39.13 (5) N3—C22—H22B 109.3
O2i—Zn3—Zn2 39.13 (5) C23—C22—H22B 109.3
C1—O1—Zn2 127.79 (17) H22A—C22—H22B 108.0
C1—O1—Zn1 120.56 (17) C24—C23—C22 115.8 (2)
Zn2—O1—Zn1 96.78 (8) C24—C23—H23A 108.3
C15—O2—Zn2 118.78 (16) C22—C23—H23A 108.3
C15—O2—Zn3 121.70 (16) C24—C23—H23B 108.3
Zn2—O2—Zn3 93.73 (8) C22—C23—H23B 108.3
C7—N1—C8 114.8 (3) H23A—C23—H23B 107.4
C7—N1—Zn1 125.8 (2) N4—C24—C25 121.1 (3)
C8—N1—Zn1 118.89 (19) N4—C24—C23 119.1 (3)
C14—N2—C10 118.1 (3) C25—C24—C23 119.8 (3)
C14—N2—Zn1 118.13 (19) C26—C25—C24 120.0 (3)
C10—N2—Zn1 123.2 (2) C26—C25—H25A 120.0
C21—N3—C22 117.3 (2) C24—C25—H25A 120.0
C21—N3—Zn3 128.81 (19) C25—C26—C27 118.9 (3)
C22—N3—Zn3 113.82 (17) C25—C26—H26A 120.5
C28—N4—C24 118.3 (3) C27—C26—H26A 120.5
C28—N4—Zn3 118.68 (19) C28—C27—C26 118.2 (3)
C24—N4—Zn3 123.00 (19) C28—C27—H27A 120.9
O1—C1—C2 121.9 (3) C26—C27—H27A 120.9
O1—C1—C6 121.8 (3) N4—C28—C27 123.5 (3)
C2—C1—C6 116.3 (3) N4—C28—H28A 118.2
C3—C2—C1 122.9 (3) C27—C28—H28A 118.2
C3—C2—Br1 118.5 (2) O13—Cl1—O11 110.02 (15)
C1—C2—Br1 118.6 (2) O13—Cl1—O12 109.40 (16)
C2—C3—C4 119.1 (3) O11—Cl1—O12 109.83 (15)
C2—C3—H3A 120.5 O13—Cl1—O14 109.36 (16)
C4—C3—H3A 120.5 O11—Cl1—O14 109.75 (16)
C5—C4—C3 120.5 (3) O12—Cl1—O14 108.47 (15)
C5—C4—Br2 119.1 (2) N1S—C1S—C2S 178.9 (4)
C3—C4—Br2 120.4 (2) C1S—C2S—H2S1 109.5
C4—C5—C6 120.0 (3) C1S—C2S—H2S2 109.5
C4—C5—H5A 120.0 H2S1—C2S—H2S2 109.5
C6—C5—H5A 120.0 C1S—C2S—H2S3 109.5
C5—C6—C1 121.1 (3) H2S1—C2S—H2S3 109.5
C5—C6—C7 116.1 (3) H2S2—C2S—H2S3 109.5
Zn2—O1—C1—C2 91.5 (3) Zn2—O2—C15—C16 98.9 (3)
Zn1—O1—C1—C2 −139.4 (2) Zn3—O2—C15—C16 −145.8 (2)
Zn2—O1—C1—C6 −88.3 (3) Zn2—O2—C15—C20 −79.1 (3)
Zn1—O1—C1—C6 40.8 (3) Zn3—O2—C15—C20 36.1 (3)
O1—C1—C2—C3 178.8 (3) O2—C15—C16—C17 −176.3 (3)
C6—C1—C2—C3 −1.4 (4) C20—C15—C16—C17 1.9 (4)
O1—C1—C2—Br1 −2.1 (4) O2—C15—C16—Br3 0.3 (4)
C6—C1—C2—Br1 177.7 (2) C20—C15—C16—Br3 178.48 (19)
C1—C2—C3—C4 1.4 (4) C15—C16—C17—C18 −0.1 (4)
Br1—C2—C3—C4 −177.8 (2) Br3—C16—C17—C18 −176.7 (2)

supporting information
sup-8
Acta Cryst. (2018). E74, 1380-1383
C2—C3—C4—C5 1.2 (4) C16—C17—C18—C19 −0.9 (4)
C2—C3—C4—Br2 −178.9 (2) C16—C17—C18—Br4 173.6 (2)
C3—C4—C5—C6 −3.6 (4) C17—C18—C19—C20 0.0 (4)
Br2—C4—C5—C6 176.5 (2) Br4—C18—C19—C20 −174.4 (2)
C4—C5—C6—C1 3.5 (4) C18—C19—C20—C15 1.9 (4)
C4—C5—C6—C7 −178.2 (3) C18—C19—C20—C21 176.9 (3)
O1—C1—C6—C5 178.7 (3) O2—C15—C20—C19 175.4 (2)
C2—C1—C6—C5 −1.1 (4) C16—C15—C20—C19 −2.7 (4)
O1—C1—C6—C7 0.6 (4) O2—C15—C20—C21 0.7 (4)
C2—C1—C6—C7 −179.2 (3) C16—C15—C20—C21 −177.5 (3)
C8—N1—C7—C6 −174.9 (3) C22—N3—C21—C20 179.5 (3)
Zn1—N1—C7—C6 −3.0 (4) Zn3—N3—C21—C20 −3.8 (4)
C5—C6—C7—N1 159.0 (3) C19—C20—C21—N3 164.3 (3)
C1—C6—C7—N1 −22.8 (4) C15—C20—C21—N3 −20.7 (4)
C7—N1—C8—C9 −150.8 (3) C21—N3—C22—C23 119.6 (3)
Zn1—N1—C8—C9 36.7 (3) Zn3—N3—C22—C23 −57.7 (3)
N1—C8—C9—C10 −76.7 (3) N3—C22—C23—C24 81.3 (3)
C14—N2—C10—C11 0.0 (4) C28—N4—C24—C25 −0.5 (4)
Zn1—N2—C10—C11 −171.6 (2) Zn3—N4—C24—C25 178.0 (2)
C14—N2—C10—C9 −179.0 (3) C28—N4—C24—C23 178.8 (3)
Zn1—N2—C10—C9 9.4 (4) Zn3—N4—C24—C23 −2.6 (4)
C8—C9—C10—N2 50.5 (4) C22—C23—C24—N4 −44.7 (4)
C8—C9—C10—C11 −128.5 (3) C22—C23—C24—C25 134.6 (3)
N2—C10—C11—C12 1.4 (5) N4—C24—C25—C26 −0.2 (4)
C9—C10—C11—C12 −179.6 (3) C23—C24—C25—C26 −179.5 (3)
C10—C11—C12—C13 −1.2 (5) C24—C25—C26—C27 1.0 (4)
C11—C12—C13—C14 −0.2 (5) C25—C26—C27—C28 −1.1 (4)
C10—N2—C14—C13 −1.5 (4) C24—N4—C28—C27 0.4 (4)
Zn1—N2—C14—C13 170.5 (2) Zn3—N4—C28—C27 −178.2 (2)
C12—C13—C14—N2 1.6 (5) C26—C27—C28—N4 0.4 (4)
Symmetry code: (i) −x+1, y, −z+1/2.
Hydrogen-bond geometry (Å, º)
D—H···AD—H H···AD···AD—H···A
C9—H9A···Br1i0.99 2.92 3.854 (3) 157
C9—H9A···O1i0.99 2.60 3.317 (4) 129
C21—H21A···O14 0.95 2.57 3.080 (4) 114
C22—H22A···O14 0.99 2.58 3.099 (4) 113
C22—H22B···Br4ii 0.99 2.96 3.664 (3) 129
C23—H23A···O12iii 0.99 2.58 3.427 (4) 144
C28—H28A···N3i0.95 2.60 3.236 (4) 125
C2S—H2S1···O11 0.98 2.60 3.556 (4) 165
C2S—H2S2···Br2 0.98 3.02 3.935 (4) 157
C2S—H2S2···Br4 0.98 3.04 3.561 (3) 115
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, −y+1, z−1/2; (iii) −x+1/2, −y+3/2, −z.