Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026864/is2171sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026864/is2171Isup2.hkl |
CCDC reference: 654887
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
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).
O-bound H atoms were located in a difference map and refined isotropically. The remaining H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C).
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).
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).
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).
C13H8Cl2O2 | Z = 4 |
Mr = 267.09 | F(000) = 544 |
Triclinic, P1 | Dx = 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 |
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 | Rint = 0.045 |
Detector resolution: 8.33 pixels mm-1 | θmax = 40.0°, θmin = 1.7° |
ω scans | h = −14→13 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −22→22 |
Tmin = 0.851, Tmax = 0.932 | l = −23→23 |
45186 measured reflections |
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(Fo2) + (0.07P)2 + 0.1204P] where P = (Fo2 + 2Fc2)/3 |
14083 reflections | (Δ/σ)max < 0.001 |
315 parameters | Δρmax = 0.71 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C13H8Cl2O2 | γ = 77.869 (1)° |
Mr = 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)° |
Bruker SMART APEX II CCD area-detector diffractometer | 14083 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 10281 reflections with I > 2σ(I) |
Tmin = 0.851, Tmax = 0.932 | Rint = 0.045 |
45186 measured reflections |
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 | Δρmax = 0.71 e Å−3 |
14083 reflections | Δρmin = −0.40 e Å−3 |
315 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.851, 0.932 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 45186, 14083, 10281 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.71, −0.40 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).
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. |
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).