4-Chloro-3-ethyl­phenol

Abstract

The title compound, C
8
H
9
ClO, packs with two independent molecules in the asymmetric unit, without significant differences in corresponding bond lengths and angles, with the ethyl group in each oriented nearly perpendicular to the aromatic ring having ring-to-side chain torsion angles of 81.14 (18) and −81.06 (19)°. In the crystal, molecules form an O—H...O hydrogen-bonded chain extending along the
b
-axis direction, through the phenol groups in which the H atoms are disordered. These chains pack together in the solid state, giving a sheet lying parallel to (001),
via
an offset face-to-face π-stacking interaction characterized by a centroid–centroid distance of 3.580 (1) Å, together with a short intermolecular Cl...Cl contact [3.412 (1) Å].

Full text

4-Chloro-3-ethylphenol
Sean H. Majer and Joseph M. Tanski*
Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA
Correspondence e-mail: jotanski@vassar.edu
Received 3 June 2014; accepted 13 June 2014
Key indicators: single-crystal X-ray study; T = 125 K; mean (C–C) = 0.002 A
˚
;
R factor = 0.037; wR factor = 0.107; data-to-parameter ratio = 25.4.
The title compound, C
8
H
9
ClO, packs with two independent
molecules in the asymmetric unit, without significant differ-
ences in correspon ding bond lengths and angles, with the ethyl
group in each oriented nearly perpendicular to the aromatic
ring having ring-to-side chain torsion angles of 81.14 (18) and
81.06 (19)

. In the crystal, molecules form an O—HO
hydrogen-bonde d chain extending along the b-axis direction,
through the phenol groups in which the H atoms are
disordered. These chains pack together in the solid state,
giving a sheet lying parallel to (001), via an offset face-to-face
-stacking interaction characterized by a centroid–centroid
distance of 3.580 (1) A
˚
, togeth er with a short intermolecular
ClCl contact [3.412 (1) A
˚
].
Related literature
For information regarding the synthesis of 4-chloro-3-ethyl-
phenol, see the following patents: Awano et al. (1987) or
Schroetter et al. (1977). For applications in biological systems,
see: Gerbershagen et al. (2005); Low et al. (1997). For similar
chlorinated phenols, see: Cox (1995, 2003); Oswald et al.
(2005). For more information on -stacking, see: Lueckheide
et al. (2013) and on halogen–halogen interactions, see: Pedir-
eddi et al. (1994).
Experimental
Crystal data
C
8
H
9
ClO
M
r
= 156.60
Triclinic, P
1
a = 7.5580 (7) A
˚
b = 8.6854 (8) A
˚
c = 12.2520 (11) A
˚
 = 78.363 (1)

 = 78.762 (1)

 = 80.355 (1)

V = 765.72 (12) A
˚
3
Z =4
Mo K radiation
 = 0.42 mm
1
T = 125 K
0.20  0.15  0.10 mm
Data collection
Bruker APEXII CCD
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
T
min
= 0.910, T
max
= 0.949
17904 measured reflections
4656 independent reflections
4176 reflections with I >2(I)
R
int
= 0.019
Refinement
R[F
2
>2(F
2
)] = 0.037
wR(F
2
) = 0.107
S = 1.13
4656 reflections
183 parameters
4 restraints
H-atom parameters constrained

max
= 0.48 e A
˚
3

min
= 0.26 e A
˚
3
Table 1
Hydrogen-bond geometry (A
˚
,

).
D—HAD—H HADAD—HA
O1—H1O1
i
0.81 1.97 2.708 (3) 152
O1—H1AO2
i
0.81 1.86 2.6642 (17) 171
O2—H2O1
i
0.81 1.86 2.6642 (17) 168
O2—H2AO2
ii
0.82 1.91 2.704 (2) 166
Symmetry codes: (i) x þ 1; y þ 1; z þ 1; (ii) x þ 1; y; z þ 1.
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT
(Bruker, 2007); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine
structure: SHELXL97 (Sheldrick, 2008); molecular graphics:
SHELXTL (Sheldrick, 2008); software used to prepare material for
publication: SHELXTL, OLEX2 (Dolomanov et al., 2009) and
Mercury (Macrae et al., 2006).
This work was supported by Vassar College. X-ray facilities
were provided by the US National Science Foundation (grant
No. 0521237 to JMT).
Supporting information for this paper is available from the IUCr
electronic archives (Reference: ZS2303).
References
Awano, Y., Nakanishi, A. & Nonaka, Y. (1987). JP Patent 62 198 631.
Bruker (2007). SAINT, SADABS and APEX2. Bruxer AXS Inc., Madison,
Wisconsin, USA.
Cox, P. J. (1995). Acta Cryst. C51, 1361–1364.
Cox, P. J. (2003). Acta Cryst. C59, o533–o536.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann,
H. (2009). J. Appl. Cryst. 42, 339–341.
Gerbershagen, M. U., Fiege, M., Weisshorn, R., Kolodzie, K., Esch, J. S. &
Wappler, F. (2005). Anesth. Analg. 101, 710–714.
Low, A. M., Sormaz, L., Kwan, C.-Y. & Daniel, E. E. (1997). Br. J. Pharmacol.
122, 504–510.
Lueckheide, M., Rothman, N., Ko, B. & Tanski, J. M. (2013). Polyhedron, 58,
79–84.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor,
R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.
Oswald, I. D. H., Allan, D. R., Motherwell, W. D. S. & Parsons, S. (2005). Acta
Cryst. B61, 69–79.
Pedireddi, V. R., Reddy, D. S., Goud, B. S., Craig, D. C., Rae, A. D. & Desiraju,
G. R. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 2353–2360.
Schroetter, E., Weuffen, W. & Wigert, H. (1977). DD Patent 124 296.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
organic compounds
Acta Cryst. (2014). E70, o801 doi:10.1107/S1600536814013919 Majer and Tanski o801
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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Acta Cryst. (2014). E70, o801
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Acta Cryst. (2014). E70, o801 [doi:10.1107/S1600536814013919]
4-Chloro-3-ethylphenol
Sean H. Majer and Joseph M. Tanski
1. Comment
4-Chloro-3-ethylphenol, the title compound, can be synthesized by chlorination of 3-ethylphenol by SO
2
Cl
2
in the
presence of FeCl
3
in CCl
4
(Awano et al., 1987) or by adding the hydroxyl group to 1-ethyl-2-nitrobenzene followed by an
acidic workup and a Sandmeyer reaction with CuCl (Schroetter et al., 1977). The title compound has been found to be
useful in multiple biological applications, including testing the contracture in malignant hypothermia skeletal tissue (Low
et al., 1997) and in biological activity on Ca
2+
deposits in muscle cells (Gerbershagen et al., 2005).
The two independent molecules of the title compound in the asymmetric unit (Fig. 1) exhibit C—Cl bond lengths of
1.7430 (15) and 1.7469 (15) Å, and C—O bond lengths of 1.3751 (18) and 1.3778 (17) Å, respectively. These are in very
close agreement with analogous bond lengths in the stuctures of 4-chlorophenol (Oswald et al., 2005), 4-chloro-3-
methylphenol (Cox, 2003), and 4-chloro-3,5-dimethylphenol (Cox, 1995). The ethyl group is rotated nearly perpendicular
to the plane of the ring for each independent molecule, displaying very similar torsion angles of 81.14 (18)° (C4—C3—
C7—C8) and -81.06 (19)° (C12—C11—C15—C16). The structure forms a one-dimensional O—H···O hydrogen-bonded
chain through the phenol groups, in which the phenol protons are 50% rotationally disordered (Fig. 2). These chains run
parallel to the crystallographic b-axis. Each independent molecule forms hydrogen bonds with a neighboring equivalent
independent molecule, with an oxygen–oxygen distance (O1···O1
i
) of 2.708 (3) Å and an oxygen–oxygen distance
(O2···O2
ii
) of 2.704 (2) Å [for symmetry codes (i) and (ii), see Table 1]. These pairwise dimers are hydrogen-bonded to
one another resulting in a third unique hydrogen bond, (O1···O2
i
), with length 2.6642 (17) Å. A similar hydrogen-bonding
motif is found in the ordered one-dimensional hydrogen bonding chain in the structure of 4-chloro-3-methylphenol (Cox,
2003), where the O···O distances are similar at 2.711 (2) and 2.714 (2) Å. Unlike 4-chloro-3-methylphenol, where the
planes of the aromatic units on each side of the hydrogen-bonded chain are parallel, in the the title compound they form a
herringbone (edge-to-face or T) motif.
Neighboring hydrogen-bonded chains pack together in the solid state to form a two-dimensional sheet parallel to the 0 0
1 plane via an offset face-to-face π-stacking interaction of one of the two independent molecules, whereas the other
molecule does not engage in π-stacking (Fig. 3). The π-stacking is characterized by a centroid-to-centroid distance of
3.580 (1) Å, a plane-to-centroid distance of 3.410 (1) Å, and a ring offset or ring-slipage distance of 1.092 (3) Å
(Lueckheide et al., 2013). Neighboring sheets are further linked by a short intermolecular chlorine–chlorine contact
(Cl1···Cl2
iii
) of 3.412 (1) Å, which is less than the sum of the van der Waals radii of 3.50 Å for chlorine–chlorine
interactions (Pedireddi et al., 1994). For symmetry code (iii): -x, -y + 1, -z.
2. Experimental
4-Chloro-3-ethylphenol was purchased from Aldrich Chemical Company, USA, and recrystallized from hexanes.

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Acta Cryst. (2014). E70, o801
3. Refinement
All non-hydrogen atoms were refined anisotropically. Hydrogen atoms on carbon were included in calculated positions
and refined using a riding model with C–H = 0.95, 0.98 and 0.99 Å and U
iso
(H) = 1.2, 1.5 and 1.2 × U
eq
(C) of the aryl,
methyl and methylene C-atoms, respectively. The positions of the disordered phenolic hydrogen atoms were found in the
difference map and refined semi-freely at 50% occupancy using a distance restraint d(O–H) = 0.84 Å, and U
iso
(H) = 1.2×
U
eq
(O).
Figure 1
A view of the two independent molecules of the title compound with the atom numbering scheme. Displacement
ellipsoids are shown at the 50% probability level. The disordered phenolic hydrogen atoms are represented with dashed
open bonds.

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Acta Cryst. (2014). E70, o801
Figure 2
A view of the one-dimensional hydrogen-bonded chain extending along b, with displacement ellipsoids shown at the 50%
probability level. For symmetry codes (i) and (ii), see Table 1.

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Acta Cryst. (2014). E70, o801
Figure 3
A view of the offset face-to-face π-stacking in the structure of title compound, with a solid line indicating one interaction
and a dashed line indicating one of the Cl1···Cl2 interactions. For symmetry codes: (iii) -x, -y + 1, -z; (iv): -x, -y + 1, -z +
1. Displacement ellipsoids are shown at the 50% probability level.
4-chloro-3-ethylphenol
Crystal data
C
8
H
9
ClO
M
r
= 156.60
Triclinic, P1
Hall symbol: -P 1
a = 7.5580 (7) Å
b = 8.6854 (8) Å
c = 12.2520 (11) Å
α = 78.363 (1)°
β = 78.762 (1)°
γ = 80.355 (1)°
V = 765.72 (12) Å
3
Z = 4
F(000) = 328
D
x
= 1.358 Mg m
−3

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Acta Cryst. (2014). E70, o801
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 9958 reflections
θ = 2.7–30.5°
µ = 0.42 mm
−1
T = 125 K
Block, colourless
0.20 × 0.15 × 0.10 mm
Data collection
Bruker APEXII CCD
diffractometer
Radiation source: fine-focus sealed tube
Graphite monochromator
φ and ω scans
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
T
min
= 0.910, T
max
= 0.949
17904 measured reflections
4656 independent reflections
4176 reflections with I > 2σ(I)
R
int
= 0.019
θ
max
= 30.5°, θ
min
= 1.7°
h = −10→10
k = −12→12
l = −17→17
Refinement
Refinement on F
2
Least-squares matrix: full
R[F
2
> 2σ(F
2
)] = 0.037
wR(F
2
) = 0.107
S = 1.13
4656 reflections
183 parameters
4 restraints
Primary atom site location: structure-invariant
direct methods
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
w = 1/[σ
2
(F
o
2
) + (0.0336P)
2
+ 0.751P]
where P = (F
o
2
+ 2F
c
2
)/3
(Δ/σ)
max
< 0.001
Δρ
max
= 0.48 e Å
−3
Δρ
min
= −0.26 e Å
−3
Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full
covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and
torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry.
An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F
2
against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F
2
,
conventional R-factors R are based on F, with F set to zero for negative F
2
. The threshold expression of F
2
> σ(F
2
) is used
only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F
2
are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å
2
)
xyzU
iso
*/U
eq
Occ. (<1)
Cl1 −0.28100 (5) 0.74811 (5) 0.30473 (4) 0.02708 (10)
O1 0.36924 (19) 0.62233 (15) 0.52135 (12) 0.0328 (3)
H1 0.4258 0.5340 0.5280 0.039* 0.50
H1A 0.4024 0.7019 0.5320 0.039* 0.50
C1 0.2194 (2) 0.65320 (17) 0.46838 (13) 0.0186 (3)
C2 0.20646 (19) 0.56371 (16) 0.38898 (12) 0.0173 (3)
H2B 0.3035 0.4836 0.3702 0.021*
C3 0.05376 (19) 0.58914 (16) 0.33626 (11) 0.0157 (2)
C4 −0.08454 (19) 0.70975 (17) 0.36563 (12) 0.0171 (3)
C5 −0.0719 (2) 0.80067 (17) 0.44421 (13) 0.0192 (3)
H5A −0.1676 0.8822 0.4622 0.023*
C6 0.0802 (2) 0.77258 (17) 0.49633 (12) 0.0197 (3)

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Acta Cryst. (2014). E70, o801
H6A 0.0894 0.8340 0.5505 0.024*
C7 0.0464 (2) 0.49276 (18) 0.24819 (13) 0.0207 (3)
H7A −0.0793 0.4686 0.2557 0.025*
H7B 0.1272 0.3910 0.2611 0.025*
C8 0.1054 (3) 0.5813 (2) 0.12819 (13) 0.0276 (3)
H8A 0.1021 0.5144 0.0733 0.041*
H8B 0.2294 0.6062 0.1207 0.041*
H8C 0.0223 0.6799 0.1140 0.041*
Cl2 0.36637 (6) 0.24774 (5) −0.04071 (3) 0.02827 (10)
O2 0.53688 (18) 0.12745 (14) 0.41968 (10) 0.0271 (3)
H2 0.5511 0.2054 0.4427 0.033* 0.50
H2A 0.5219 0.0420 0.4598 0.033* 0.50
C9 0.4935 (2) 0.15527 (17) 0.31266 (12) 0.0171 (3)
C10 0.37918 (19) 0.06378 (16) 0.28560 (12) 0.0172 (3)
H10A 0.3293 −0.0170 0.3419 0.021*
C11 0.33641 (19) 0.08887 (17) 0.17674 (12) 0.0172 (3)
C12 0.4129 (2) 0.20931 (18) 0.09713 (12) 0.0188 (3)
C13 0.5254 (2) 0.30228 (18) 0.12387 (13) 0.0204 (3)
H13A 0.5744 0.3839 0.0679 0.024*
C14 0.5662 (2) 0.27599 (18) 0.23228 (13) 0.0195 (3)
H14A 0.6426 0.3394 0.2513 0.023*
C15 0.2080 (2) −0.00900 (19) 0.15052 (14) 0.0233 (3)
H15A 0.2089 −0.1105 0.2046 0.028*
H15B 0.2514 −0.0339 0.0736 0.028*
C16 0.0132 (2) 0.0767 (2) 0.15729 (16) 0.0292 (3)
H16A −0.0649 0.0098 0.1385 0.044*
H16B 0.0116 0.1770 0.1036 0.044*
H16C −0.0320 0.0981 0.2341 0.044*
Atomic displacement parameters (Å
2
)
U
11
U
22
U
33
U
12
U
13
U
23
Cl1 0.01775 (17) 0.0333 (2) 0.0317 (2) 0.00267 (14) −0.00926 (14) −0.00914 (16)
O1 0.0381 (7) 0.0216 (5) 0.0469 (8) −0.0047 (5) −0.0307 (6) −0.0013 (5)
C1 0.0229 (7) 0.0145 (6) 0.0204 (6) −0.0042 (5) −0.0092 (5) −0.0007 (5)
C2 0.0173 (6) 0.0147 (6) 0.0199 (6) −0.0004 (5) −0.0041 (5) −0.0032 (5)
C3 0.0172 (6) 0.0154 (6) 0.0147 (6) −0.0028 (5) −0.0022 (5) −0.0027 (5)
C4 0.0152 (6) 0.0188 (6) 0.0172 (6) −0.0018 (5) −0.0030 (5) −0.0029 (5)
C5 0.0201 (6) 0.0165 (6) 0.0199 (6) −0.0011 (5) −0.0007 (5) −0.0042 (5)
C6 0.0262 (7) 0.0162 (6) 0.0180 (6) −0.0039 (5) −0.0045 (5) −0.0044 (5)
C7 0.0224 (7) 0.0223 (7) 0.0195 (6) −0.0016 (5) −0.0051 (5) −0.0084 (5)
C8 0.0329 (8) 0.0333 (8) 0.0170 (7) 0.0006 (7) −0.0055 (6) −0.0085 (6)
Cl2 0.0300 (2) 0.0399 (2) 0.01504 (16) −0.00312 (16) −0.00605 (13) −0.00440 (14)
O2 0.0433 (7) 0.0205 (5) 0.0222 (5) −0.0027 (5) −0.0190 (5) −0.0029 (4)
C9 0.0188 (6) 0.0160 (6) 0.0173 (6) 0.0007 (5) −0.0071 (5) −0.0035 (5)
C10 0.0184 (6) 0.0152 (6) 0.0180 (6) −0.0014 (5) −0.0048 (5) −0.0022 (5)
C11 0.0161 (6) 0.0174 (6) 0.0194 (6) 0.0012 (5) −0.0054 (5) −0.0063 (5)
C12 0.0182 (6) 0.0240 (7) 0.0140 (6) 0.0010 (5) −0.0042 (5) −0.0045 (5)

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Acta Cryst. (2014). E70, o801
C13 0.0185 (6) 0.0232 (7) 0.0183 (6) −0.0040 (5) −0.0016 (5) −0.0011 (5)
C14 0.0178 (6) 0.0200 (6) 0.0220 (7) −0.0036 (5) −0.0052 (5) −0.0039 (5)
C15 0.0236 (7) 0.0223 (7) 0.0280 (8) −0.0042 (6) −0.0098 (6) −0.0075 (6)
C16 0.0220 (7) 0.0332 (9) 0.0340 (9) −0.0055 (6) −0.0099 (6) −0.0031 (7)
Geometric parameters (Å, º)
Cl1—C4 1.7430 (15) Cl2—C12 1.7469 (15)
O1—C1 1.3751 (18) O2—C9 1.3778 (17)
O1—H1 0.8098 O2—H2 0.8144
O1—H1A 0.8145 O2—H2A 0.8150
C1—C2 1.388 (2) C9—C10 1.391 (2)
C1—C6 1.391 (2) C9—C14 1.392 (2)
C2—C3 1.395 (2) C10—C11 1.399 (2)
C2—H2B 0.9500 C10—H10A 0.9500
C3—C4 1.3993 (19) C11—C12 1.397 (2)
C3—C7 1.5072 (19) C11—C15 1.508 (2)
C4—C5 1.388 (2) C12—C13 1.388 (2)
C5—C6 1.385 (2) C13—C14 1.388 (2)
C5—H5A 0.9500 C13—H13A 0.9500
C6—H6A 0.9500 C14—H14A 0.9500
C7—C8 1.535 (2) C15—C16 1.529 (2)
C7—H7A 0.9900 C15—H15A 0.9900
C7—H7B 0.9900 C15—H15B 0.9900
C8—H8A 0.9800 C16—H16A 0.9800
C8—H8B 0.9800 C16—H16B 0.9800
C8—H8C 0.9800 C16—H16C 0.9800
C1—O1—H1 119.3 C9—O2—H2 115.6
C1—O1—H1A 113.5 C9—O2—H2A 118.3
H1—O1—H1A 126.1 H2—O2—H2A 124.2
O1—C1—C2 119.94 (14) O2—C9—C10 120.42 (13)
O1—C1—C6 119.55 (14) O2—C9—C14 118.89 (13)
C2—C1—C6 120.51 (13) C10—C9—C14 120.69 (13)
C1—C2—C3 121.26 (13) C9—C10—C11 121.06 (13)
C1—C2—H2B 119.4 C9—C10—H10A 119.5
C3—C2—H2B 119.4 C11—C10—H10A 119.5
C2—C3—C4 117.27 (13) C12—C11—C10 117.20 (13)
C2—C3—C7 119.86 (13) C12—C11—C15 122.80 (13)
C4—C3—C7 122.82 (13) C10—C11—C15 119.97 (13)
C5—C4—C3 121.79 (13) C13—C12—C11 122.05 (13)
C5—C4—Cl1 117.97 (11) C13—C12—Cl2 117.98 (12)
C3—C4—Cl1 120.23 (11) C11—C12—Cl2 119.97 (11)
C6—C5—C4 120.02 (13) C14—C13—C12 120.01 (14)
C6—C5—H5A 120.0 C14—C13—H13A 120.0
C4—C5—H5A 120.0 C12—C13—H13A 120.0
C5—C6—C1 119.14 (13) C13—C14—C9 118.97 (14)
C5—C6—H6A 120.4 C13—C14—H14A 120.5

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Acta Cryst. (2014). E70, o801
C1—C6—H6A 120.4 C9—C14—H14A 120.5
C3—C7—C8 111.60 (13) C11—C15—C16 112.21 (13)
C3—C7—H7A 109.3 C11—C15—H15A 109.2
C8—C7—H7A 109.3 C16—C15—H15A 109.2
C3—C7—H7B 109.3 C11—C15—H15B 109.2
C8—C7—H7B 109.3 C16—C15—H15B 109.2
H7A—C7—H7B 108.0 H15A—C15—H15B 107.9
C7—C8—H8A 109.5 C15—C16—H16A 109.5
C7—C8—H8B 109.5 C15—C16—H16B 109.5
H8A—C8—H8B 109.5 H16A—C16—H16B 109.5
C7—C8—H8C 109.5 C15—C16—H16C 109.5
H8A—C8—H8C 109.5 H16A—C16—H16C 109.5
H8B—C8—H8C 109.5 H16B—C16—H16C 109.5
O1—C1—C2—C3 178.12 (13) O2—C9—C10—C11 −178.90 (13)
C6—C1—C2—C3 −0.8 (2) C14—C9—C10—C11 1.0 (2)
C1—C2—C3—C4 0.8 (2) C9—C10—C11—C12 −0.1 (2)
C1—C2—C3—C7 178.38 (13) C9—C10—C11—C15 −178.34 (13)
C2—C3—C4—C5 −0.2 (2) C10—C11—C12—C13 −0.6 (2)
C7—C3—C4—C5 −177.72 (14) C15—C11—C12—C13 177.52 (14)
C2—C3—C4—Cl1 −179.38 (11) C10—C11—C12—Cl2 179.89 (11)
C7—C3—C4—Cl1 3.11 (19) C15—C11—C12—Cl2 −2.0 (2)
C3—C4—C5—C6 −0.3 (2) C11—C12—C13—C14 0.5 (2)
Cl1—C4—C5—C6 178.84 (11) Cl2—C12—C13—C14 −179.95 (12)
C4—C5—C6—C1 0.3 (2) C12—C13—C14—C9 0.3 (2)
O1—C1—C6—C5 −178.70 (14) O2—C9—C14—C13 178.84 (13)
C2—C1—C6—C5 0.2 (2) C10—C9—C14—C13 −1.1 (2)
C2—C3—C7—C8 −96.30 (16) C12—C11—C15—C16 −81.06 (19)
C4—C3—C7—C8 81.14 (18) C10—C11—C15—C16 97.03 (17)
Hydrogen-bond geometry (Å, º)
D—H···AD—H H···AD···AD—H···A
O1—H1···O1
i
0.81 1.97 2.708 (3) 152
O1—H1A···O2
i
0.81 1.86 2.6642 (17) 171
O2—H2···O1
i
0.81 1.86 2.6642 (17) 168
O2—H2A···O2
ii
0.82 1.91 2.704 (2) 166
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1.