(2,5-Dichloro-4-hydroxy­phen­yl)(phen­yl)­methanone

Fun, H.-K.; Ng, S.-L.; Li, Z.; Xu, J.-H.

doi:10.1107/S1600536807026864

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(2,5-Dichloro-4-hydroxyphenyl)(phenyl)methanone

H.-K. Fun, S.-L. Ng, Z. Li and J.-H. Xu

The title compound, C₁₃H₈Cl₂O₂, crystallizes with two independent molecules in the asymmetric unit. Each of the two unique molecules is twisted about the C—C single bonds, making dihedral angles of 24.29 (5) and 73.01 (5)° between the two rings. In the crystal structure, the molecules are interlinked into columns along the b axis by intermolecular O—H

O and C—H

O interactions and short Cl

Cl and O

Cl contacts. In addition, the crystal packing is further stabilized by weak C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026864/is2171sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026864/is2171Isup2.hkl Contains datablock I

CCDC reference: 654887

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.044
wR factor = 0.134
Data-to-parameter ratio = 44.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.69 mm
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.72 Ratio
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1B   ..  O2A     ..       3.25 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2A   ..  O2B     ..       3.24 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The photochemistry of quinone compounds is of continuing research interest (Patai & Rappoport, 1988; Thomson, 1997). In continuation of our recent work on photoinduced reactions of quinones with alkynes (Zhang et al., 2000), the title compound, (I), was obtained by the reaction of photoexcited 2,5-dichlorobenzoquinone with trimethylsilyphenylethyne. A crystallographic analysis of (I) was carried out to elucidate its structure.

The asymmetric unit of (I) contains two unique molecules, labelled A and B (Fig. 1). Bond lengths and angles in the two molecules are similar, display normal values (Allen et al., 1987) and are comparable to those observed in related structures (Kutzke et al., 2000; Harrison et al., 2005). Each of the two unique molecules is twisted about C6—C7 and C7—C8 bonds with dihedral angle between the phenyl (C8—C13) and benzene (C1—C6) rings of 24.29 (5)° in molecule A and 73.01 (5)° in molecule B.

Intramolecular O1A—H1A···O2B and O9A—H9A···O1B interactions are observed in the molecular structure and another intramolecular O1A—H1A···Cl2A interaction generates a S(5) ring motif (Bernstein et al., 1995) (Table 1 and Fig. 1). In the crystal structure, the molecules are linked into columns along the b axis by intermolecular O1B—H1B···O2A, C5B—H5B···O2B, C9B—H9B···O1A, C10A—H10A···O2A interactions (Table 1) and short Cl1A···Cl2B contact (2 - x, 1 - y, -z) of 3.3109 (4) Å and short O2B···Cl2A (x, y, z) contact of 3.2387 (9) Å. In addition, the crystal structure is further stabilized by C—H···π interactions involving the C8A—C13A ring (centroid Cg1) and C8B—C13B ring (centroid Cg2; Table 1).

Related literature top

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For related literature on values of bond lengths and angles, see: Allen et al. (1987). For related structures, see: Harrison et al. (2005); Kutzke et al. (2000); Patai & Rappoport (1988); Thomson (1997); Zhang et al. (2000).

Experimental top

The title compound, (I), was synthesized by photo-induced reaction between 2,5-dichlorobenzoquinone (0.05M) and an excess amount of 1-phenyl-2-trimethyl-silylacetylene (0.1M) in a benzene solution. The title compound was isolated using silica gel column chromatography. Single crystal suitable for X-ray Diffraction analysis were obtained by slow evaporation of the solvent from a petroleum ether-acetone solution (v:v = 2:1).

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures top

	Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering. The dashed lines indicate intramolecular hydrogen bonds.
	Fig. 2. The crystal packing of (I), viewed down the a axis. The intermolecular O—H···O, C—H···O interactions and short Cl···Cl and O···Cl contacts are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

(2,5-Dichloro-4-hydroxyphenyl)(phenyl)methanone top

Crystal data top

C₁₃H₈Cl₂O₂	Z = 4
M_r = 267.09	F(000) = 544
Triclinic, P1	D_x = 1.543 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8450 (2) Å	Cell parameters from 9206 reflections
b = 12.1815 (3) Å	θ = 1.7–40.0°
c = 12.9442 (3) Å	µ = 0.55 mm⁻¹
α = 73.087 (1)°	T = 100 K
β = 80.468 (1)°	Needle, yellow
γ = 77.869 (1)°	0.69 × 0.14 × 0.13 mm
V = 1149.83 (5) Å³

Data collection top

Bruker SMART APEX II CCD area-detector diffractometer	14083 independent reflections
Radiation source: fine-focus sealed tube	10281 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 8.33 pixels mm^-1	θ_max = 40.0°, θ_min = 1.7°
ω scans	h = −14→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −22→22
T_min = 0.851, T_max = 0.932	l = −23→23
45186 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.07P)² + 0.1204P] where P = (F_o² + 2F_c²)/3
14083 reflections	(Δ/σ)_max < 0.001
315 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₃H₈Cl₂O₂	γ = 77.869 (1)°
M_r = 267.09	V = 1149.83 (5) Å³
Triclinic, P1	Z = 4
a = 7.8450 (2) Å	Mo Kα radiation
b = 12.1815 (3) Å	µ = 0.55 mm⁻¹
c = 12.9442 (3) Å	T = 100 K
α = 73.087 (1)°	0.69 × 0.14 × 0.13 mm
β = 80.468 (1)°

Data collection top

Bruker SMART APEX II CCD area-detector diffractometer	14083 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	10281 reflections with I > 2σ(I)
T_min = 0.851, T_max = 0.932	R_int = 0.045
45186 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.71 e Å⁻³
14083 reflections	Δρ_min = −0.40 e Å⁻³
315 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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 F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1A	1.21145 (4)	0.42758 (2)	0.14684 (2)	0.02036 (6)
Cl2A	1.11196 (4)	−0.08855 (2)	0.34500 (2)	0.02122 (6)
O1A	1.20212 (11)	0.02950 (7)	0.10794 (7)	0.01715 (14)
O2A	1.29008 (11)	0.33763 (7)	0.40468 (7)	0.01849 (14)
C1A	1.19193 (14)	0.28251 (8)	0.20409 (8)	0.01425 (15)
C2A	1.20829 (14)	0.21146 (9)	0.13519 (8)	0.01515 (16)
H2A	1.2358	0.2406	0.0608	0.018*
C3A	1.18331 (14)	0.09584 (9)	0.17802 (8)	0.01402 (15)
C4A	1.14106 (15)	0.05442 (9)	0.29037 (8)	0.01506 (16)
C5A	1.12360 (15)	0.12666 (9)	0.35824 (8)	0.01615 (17)
H5A	1.0928	0.0984	0.4324	0.019*
C6A	1.15179 (14)	0.24117 (8)	0.31614 (8)	0.01425 (15)
C7A	1.15246 (14)	0.30976 (9)	0.39545 (8)	0.01504 (16)
C8A	0.98836 (14)	0.33652 (9)	0.46450 (8)	0.01536 (16)
C9A	0.82712 (15)	0.33859 (10)	0.43122 (9)	0.01840 (18)
H9A	0.8233	0.3208	0.3665	0.022*
C10A	0.67211 (16)	0.36722 (11)	0.49482 (10)	0.02078 (19)
H10A	0.5645	0.3705	0.4719	0.025*
C11A	0.67853 (16)	0.39093 (11)	0.59253 (10)	0.0214 (2)
H11A	0.5749	0.4090	0.6355	0.026*
C12A	0.83915 (16)	0.38791 (10)	0.62660 (9)	0.02002 (19)
H12A	0.8424	0.4030	0.6926	0.024*
C13A	0.99431 (15)	0.36248 (9)	0.56253 (9)	0.01752 (17)
H13A	1.1014	0.3626	0.5843	0.021*
Cl1B	0.60271 (4)	−0.12704 (2)	0.38336 (2)	0.02222 (6)
Cl2B	0.78417 (4)	0.32958 (2)	0.05205 (2)	0.02021 (6)
O1B	0.57634 (12)	0.31234 (7)	0.26102 (7)	0.01826 (14)
O2B	0.99729 (10)	−0.13362 (7)	0.13368 (7)	0.01718 (14)
C1B	0.64770 (14)	−0.00127 (9)	0.28591 (8)	0.01513 (16)
C2B	0.58807 (14)	0.10414 (9)	0.31248 (8)	0.01622 (17)
H2B	0.5217	0.1056	0.3788	0.019*
C3B	0.62768 (14)	0.20750 (9)	0.23996 (9)	0.01485 (16)
C4B	0.73060 (14)	0.20223 (9)	0.14140 (8)	0.01504 (16)
C5B	0.79192 (14)	0.09678 (9)	0.11646 (8)	0.01471 (16)
H5B	0.8614	0.0951	0.0512	0.018*
C6B	0.75091 (13)	−0.00739 (8)	0.18803 (8)	0.01396 (15)
C7B	0.83740 (14)	−0.11867 (9)	0.15979 (8)	0.01430 (15)
C8B	0.73470 (14)	−0.20686 (9)	0.15805 (8)	0.01449 (15)
C9B	0.55771 (15)	−0.17591 (10)	0.14169 (9)	0.01820 (18)
H9B	0.4995	−0.1003	0.1382	0.022*
C10B	0.46854 (16)	−0.25846 (11)	0.13056 (10)	0.0214 (2)
H10B	0.3512	−0.2376	0.1180	0.026*
C11B	0.55468 (17)	−0.37246 (11)	0.13812 (10)	0.0219 (2)
H11B	0.4946	−0.4275	0.1308	0.026*
C12B	0.73054 (17)	−0.40425 (10)	0.15661 (10)	0.01992 (19)
H12B	0.7871	−0.4808	0.1633	0.024*
C13B	0.82109 (15)	−0.32137 (9)	0.16503 (9)	0.01722 (17)
H13B	0.9393	−0.3419	0.1753	0.021*
H1A	1.152 (3)	−0.026 (2)	0.1361 (19)	0.041 (6)*
H1B	0.483 (4)	0.308 (2)	0.313 (2)	0.067 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1A	0.02938 (14)	0.01235 (10)	0.01944 (11)	−0.00720 (9)	−0.00470 (9)	−0.00072 (8)
Cl2A	0.03286 (15)	0.01249 (10)	0.01933 (11)	−0.00818 (9)	−0.00370 (10)	−0.00230 (8)
O1A	0.0191 (3)	0.0172 (3)	0.0182 (3)	−0.0055 (3)	0.0006 (3)	−0.0091 (3)
O2A	0.0171 (3)	0.0186 (3)	0.0228 (4)	−0.0044 (3)	−0.0011 (3)	−0.0098 (3)
C1A	0.0165 (4)	0.0117 (3)	0.0150 (4)	−0.0046 (3)	−0.0017 (3)	−0.0028 (3)
C2A	0.0183 (4)	0.0141 (4)	0.0137 (4)	−0.0051 (3)	−0.0017 (3)	−0.0032 (3)
C3A	0.0144 (4)	0.0136 (4)	0.0152 (4)	−0.0028 (3)	−0.0018 (3)	−0.0051 (3)
C4A	0.0193 (4)	0.0114 (3)	0.0149 (4)	−0.0048 (3)	−0.0018 (3)	−0.0027 (3)
C5A	0.0215 (5)	0.0137 (4)	0.0138 (4)	−0.0051 (3)	−0.0009 (3)	−0.0038 (3)
C6A	0.0166 (4)	0.0122 (3)	0.0144 (4)	−0.0036 (3)	−0.0009 (3)	−0.0039 (3)
C7A	0.0176 (4)	0.0119 (3)	0.0157 (4)	−0.0028 (3)	−0.0016 (3)	−0.0038 (3)
C8A	0.0169 (4)	0.0130 (4)	0.0165 (4)	−0.0027 (3)	−0.0016 (3)	−0.0046 (3)
C9A	0.0188 (4)	0.0185 (4)	0.0190 (4)	−0.0029 (3)	−0.0027 (3)	−0.0066 (3)
C10A	0.0166 (4)	0.0225 (5)	0.0232 (5)	−0.0015 (4)	−0.0025 (4)	−0.0071 (4)
C11A	0.0204 (5)	0.0209 (5)	0.0205 (5)	0.0003 (4)	0.0002 (4)	−0.0058 (4)
C12A	0.0241 (5)	0.0187 (4)	0.0165 (4)	−0.0007 (4)	−0.0015 (4)	−0.0060 (3)
C13A	0.0202 (5)	0.0167 (4)	0.0170 (4)	−0.0025 (3)	−0.0034 (3)	−0.0062 (3)
Cl1B	0.03089 (14)	0.01500 (10)	0.01745 (11)	−0.00506 (9)	0.00498 (9)	−0.00264 (8)
Cl2B	0.02614 (13)	0.01347 (10)	0.01999 (11)	−0.00595 (8)	−0.00007 (9)	−0.00241 (8)
O1B	0.0192 (4)	0.0139 (3)	0.0231 (4)	−0.0017 (3)	−0.0004 (3)	−0.0090 (3)
O2B	0.0138 (3)	0.0177 (3)	0.0221 (3)	−0.0033 (2)	0.0003 (3)	−0.0093 (3)
C1B	0.0165 (4)	0.0130 (4)	0.0149 (4)	−0.0027 (3)	0.0007 (3)	−0.0034 (3)
C2B	0.0173 (4)	0.0153 (4)	0.0158 (4)	−0.0021 (3)	0.0005 (3)	−0.0055 (3)
C3B	0.0143 (4)	0.0137 (4)	0.0176 (4)	−0.0013 (3)	−0.0021 (3)	−0.0063 (3)
C4B	0.0169 (4)	0.0120 (3)	0.0162 (4)	−0.0030 (3)	−0.0014 (3)	−0.0035 (3)
C5B	0.0155 (4)	0.0136 (4)	0.0148 (4)	−0.0028 (3)	0.0002 (3)	−0.0044 (3)
C6B	0.0149 (4)	0.0122 (3)	0.0147 (4)	−0.0022 (3)	−0.0003 (3)	−0.0042 (3)
C7B	0.0153 (4)	0.0137 (4)	0.0143 (4)	−0.0025 (3)	−0.0007 (3)	−0.0049 (3)
C8B	0.0154 (4)	0.0130 (4)	0.0159 (4)	−0.0034 (3)	−0.0012 (3)	−0.0047 (3)
C9B	0.0157 (4)	0.0175 (4)	0.0221 (4)	−0.0026 (3)	−0.0013 (3)	−0.0069 (3)
C10B	0.0176 (5)	0.0231 (5)	0.0264 (5)	−0.0069 (4)	−0.0019 (4)	−0.0087 (4)
C11B	0.0247 (5)	0.0219 (5)	0.0231 (5)	−0.0109 (4)	−0.0005 (4)	−0.0083 (4)
C12B	0.0250 (5)	0.0147 (4)	0.0215 (4)	−0.0049 (4)	−0.0029 (4)	−0.0059 (3)
C13B	0.0190 (4)	0.0137 (4)	0.0194 (4)	−0.0018 (3)	−0.0032 (3)	−0.0052 (3)

Geometric parameters (Å, º) top

Cl1A—C1A	1.7347 (10)	Cl1B—C1B	1.7373 (10)
Cl2A—C4A	1.7270 (10)	Cl2B—C4B	1.7291 (10)
O1A—C3A	1.3526 (12)	O1B—C3B	1.3481 (12)
O1A—H1A	0.82 (2)	O1B—H1B	0.91 (3)
O2A—C7A	1.2310 (14)	O2B—C7B	1.2329 (13)
C1A—C2A	1.3878 (14)	C1B—C2B	1.3919 (14)
C1A—C6A	1.3953 (14)	C1B—C6B	1.3986 (14)
C2A—C3A	1.3982 (14)	C2B—C3B	1.3940 (15)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.4012 (14)	C3B—C4B	1.4030 (15)
C4A—C5A	1.3871 (14)	C4B—C5B	1.3842 (14)
C5A—C6A	1.3925 (14)	C5B—C6B	1.4003 (14)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.5016 (14)	C6B—C7B	1.5004 (13)
C7A—C8A	1.4746 (15)	C7B—C8B	1.4790 (15)
C8A—C9A	1.3954 (16)	C8B—C9B	1.3949 (16)
C8A—C13A	1.4041 (15)	C8B—C13B	1.4010 (14)
C9A—C10A	1.3913 (16)	C9B—C10B	1.3909 (17)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.3875 (17)	C10B—C11B	1.3940 (18)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.3924 (18)	C11B—C12B	1.3934 (18)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.3863 (16)	C12B—C13B	1.3881 (16)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—H13A	0.9300	C13B—H13B	0.9300

C3A—O1A—H1A	109.4 (16)	C3B—O1B—H1B	108.4 (18)
C2A—C1A—C6A	121.50 (9)	C2B—C1B—C6B	121.63 (9)
C2A—C1A—Cl1A	118.25 (8)	C2B—C1B—Cl1B	117.40 (8)
C6A—C1A—Cl1A	120.17 (8)	C6B—C1B—Cl1B	120.81 (8)
C1A—C2A—C3A	119.78 (9)	C1B—C2B—C3B	120.14 (9)
C1A—C2A—H2A	120.1	C1B—C2B—H2B	119.9
C3A—C2A—H2A	120.1	C3B—C2B—H2B	119.9
O1A—C3A—C2A	117.74 (9)	O1B—C3B—C2B	123.29 (9)
O1A—C3A—C4A	123.40 (9)	O1B—C3B—C4B	118.08 (9)
C2A—C3A—C4A	118.87 (9)	C2B—C3B—C4B	118.60 (9)
C5A—C4A—C3A	120.77 (9)	C5B—C4B—C3B	120.86 (9)
C5A—C4A—Cl2A	119.66 (8)	C5B—C4B—Cl2B	120.14 (8)
C3A—C4A—Cl2A	119.56 (8)	C3B—C4B—Cl2B	118.98 (8)
C4A—C5A—C6A	120.52 (9)	C4B—C5B—C6B	121.01 (9)
C4A—C5A—H5A	119.7	C4B—C5B—H5B	119.5
C6A—C5A—H5A	119.7	C6B—C5B—H5B	119.5
C5A—C6A—C1A	118.54 (9)	C1B—C6B—C5B	117.73 (9)
C5A—C6A—C7A	117.61 (9)	C1B—C6B—C7B	124.50 (9)
C1A—C6A—C7A	123.63 (9)	C5B—C6B—C7B	117.40 (9)
O2A—C7A—C8A	121.80 (9)	O2B—C7B—C8B	120.02 (9)
O2A—C7A—C6A	119.70 (10)	O2B—C7B—C6B	118.30 (9)
C8A—C7A—C6A	118.42 (9)	C8B—C7B—C6B	121.62 (9)
C9A—C8A—C13A	120.05 (10)	C9B—C8B—C13B	119.89 (10)
C9A—C8A—C7A	119.99 (10)	C9B—C8B—C7B	121.09 (9)
C13A—C8A—C7A	119.95 (10)	C13B—C8B—C7B	118.85 (10)
C10A—C9A—C8A	119.97 (10)	C10B—C9B—C8B	119.81 (10)
C10A—C9A—H9A	120.0	C10B—C9B—H9B	120.1
C8A—C9A—H9A	120.0	C8B—C9B—H9B	120.1
C11A—C10A—C9A	119.83 (11)	C9B—C10B—C11B	120.12 (11)
C11A—C10A—H10A	120.1	C9B—C10B—H10B	119.9
C9A—C10A—H10A	120.1	C11B—C10B—H10B	119.9
C10A—C11A—C12A	120.41 (11)	C12B—C11B—C10B	120.21 (11)
C10A—C11A—H11A	119.8	C12B—C11B—H11B	119.9
C12A—C11A—H11A	119.8	C10B—C11B—H11B	119.9
C13A—C12A—C11A	120.27 (11)	C13B—C12B—C11B	119.79 (10)
C13A—C12A—H12A	119.9	C13B—C12B—H12B	120.1
C11A—C12A—H12A	119.9	C11B—C12B—H12B	120.1
C12A—C13A—C8A	119.44 (11)	C12B—C13B—C8B	120.14 (11)
C12A—C13A—H13A	120.3	C12B—C13B—H13B	119.9
C8A—C13A—H13A	120.3	C8B—C13B—H13B	119.9

C6A—C1A—C2A—C3A	0.36 (16)	C6B—C1B—C2B—C3B	1.34 (17)
Cl1A—C1A—C2A—C3A	−176.33 (8)	Cl1B—C1B—C2B—C3B	176.73 (9)
C1A—C2A—C3A—O1A	−179.41 (10)	C1B—C2B—C3B—O1B	−179.05 (10)
C1A—C2A—C3A—C4A	0.35 (16)	C1B—C2B—C3B—C4B	−1.06 (16)
O1A—C3A—C4A—C5A	179.96 (10)	O1B—C3B—C4B—C5B	178.03 (10)
C2A—C3A—C4A—C5A	0.21 (16)	C2B—C3B—C4B—C5B	−0.07 (16)
O1A—C3A—C4A—Cl2A	0.43 (15)	O1B—C3B—C4B—Cl2B	−0.62 (14)
C2A—C3A—C4A—Cl2A	−179.32 (8)	C2B—C3B—C4B—Cl2B	−178.72 (8)
C3A—C4A—C5A—C6A	−1.49 (17)	C3B—C4B—C5B—C6B	0.97 (17)
Cl2A—C4A—C5A—C6A	178.04 (9)	Cl2B—C4B—C5B—C6B	179.60 (8)
C4A—C5A—C6A—C1A	2.16 (16)	C2B—C1B—C6B—C5B	−0.45 (16)
C4A—C5A—C6A—C7A	−172.64 (10)	Cl1B—C1B—C6B—C5B	−175.68 (8)
C2A—C1A—C6A—C5A	−1.61 (16)	C2B—C1B—C6B—C7B	172.36 (10)
Cl1A—C1A—C6A—C5A	175.02 (8)	Cl1B—C1B—C6B—C7B	−2.88 (16)
C2A—C1A—C6A—C7A	172.86 (10)	C4B—C5B—C6B—C1B	−0.70 (16)
Cl1A—C1A—C6A—C7A	−10.51 (15)	C4B—C5B—C6B—C7B	−174.02 (10)
C5A—C6A—C7A—O2A	111.68 (12)	C1B—C6B—C7B—O2B	−124.56 (12)
C1A—C6A—C7A—O2A	−62.84 (15)	C5B—C6B—C7B—O2B	48.27 (14)
C5A—C6A—C7A—C8A	−65.16 (13)	C1B—C6B—C7B—C8B	58.16 (15)
C1A—C6A—C7A—C8A	120.32 (11)	C5B—C6B—C7B—C8B	−129.01 (11)
O2A—C7A—C8A—C9A	159.50 (11)	O2B—C7B—C8B—C9B	−152.78 (11)
C6A—C7A—C8A—C9A	−23.73 (14)	C6B—C7B—C8B—C9B	24.46 (15)
O2A—C7A—C8A—C13A	−19.07 (16)	O2B—C7B—C8B—C13B	22.49 (15)
C6A—C7A—C8A—C13A	157.70 (10)	C6B—C7B—C8B—C13B	−160.27 (10)
C13A—C8A—C9A—C10A	0.47 (17)	C13B—C8B—C9B—C10B	−1.07 (17)
C7A—C8A—C9A—C10A	−178.10 (10)	C7B—C8B—C9B—C10B	174.15 (10)
C8A—C9A—C10A—C11A	−1.54 (18)	C8B—C9B—C10B—C11B	1.42 (18)
C9A—C10A—C11A—C12A	0.94 (18)	C9B—C10B—C11B—C12B	−0.15 (19)
C10A—C11A—C12A—C13A	0.75 (18)	C10B—C11B—C12B—C13B	−1.46 (18)
C11A—C12A—C13A—C8A	−1.81 (17)	C11B—C12B—C13B—C8B	1.81 (17)
C9A—C8A—C13A—C12A	1.21 (16)	C9B—C8B—C13B—C12B	−0.54 (16)
C7A—C8A—C13A—C12A	179.77 (10)	C7B—C8B—C13B—C12B	−175.87 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···Cl2A	0.82 (2)	2.57 (2)	3.0208 (9)	116 (2)
O1A—H1A···O2B	0.82 (2)	1.97 (2)	2.7241 (12)	153 (2)
C9A—H9A···O1B	0.93	2.58	3.3070 (15)	135
O1B—H1B···O2Aⁱ	0.91 (3)	1.80 (3)	2.6936 (13)	166 (2)
C5B—H5B···O2Bⁱⁱ	0.93	2.42	3.3336 (13)	167
C9B—H9B···O1Aⁱ	0.93	2.55	3.3268 (15)	142
C10A—H10A···O2Aⁱ	0.93	2.60	3.5115 (16)	168
C13A—H13A···Cg1ⁱⁱⁱ	0.93	3.34	3.6615 (12)	103
C2A—H2A···Cg2ⁱⁱ	0.93	2.65	3.5687 (11)	170

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z; (iii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₈Cl₂O₂
M_r	267.09
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.8450 (2), 12.1815 (3), 12.9442 (3)
α, β, γ (°)	73.087 (1), 80.468 (1), 77.869 (1)
V (Å³)	1149.83 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.69 × 0.14 × 0.13

Data collection
Diffractometer	Bruker SMART APEX II CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.851, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	45186, 14083, 10281
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.904

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.134, 1.03
No. of reflections	14083
No. of parameters	315
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.40

Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···Cl2A	0.82 (2)	2.57 (2)	3.0208 (9)	116 (2)
O1A—H1A···O2B	0.82 (2)	1.97 (2)	2.7241 (12)	153 (2)
C9A—H9A···O1B	0.93	2.58	3.3070 (15)	135
O1B—H1B···O2Aⁱ	0.91 (3)	1.80 (3)	2.6936 (13)	166 (2)
C5B—H5B···O2Bⁱⁱ	0.93	2.42	3.3336 (13)	167
C9B—H9B···O1Aⁱ	0.93	2.55	3.3268 (15)	142
C10A—H10A···O2Aⁱ	0.93	2.60	3.5115 (16)	168
C13A—H13A···Cg1ⁱⁱⁱ	0.93	3.34	3.6615 (12)	103
C2A—H2A···Cg2ⁱⁱ	0.93	2.65	3.5687 (11)	170

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z; (iii) −x+2, −y+1, −z+1.

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