![](/logos/buttonlogos/cross.png)
![](/logos/buttonlogos/cross.png)
organic compounds
3-(3,4-Dichlorophenyl)-1-(2-naphthyl)prop-2-en-1-one
aForestry College, Guangxi University, Nanning 530005, People's Republic of China, and bChemistry Department, Guangxi Industrial Vocational Technical College, Nanning 530001, People's Republic of China
*Correspondence e-mail: lukz1886@yahoo.com.cn
The 19H12Cl2O, contains four independent molecules, which can be divided into two pairs of molecules with close values of the C—C(=O)—C=C torsion angles in each pair, viz. 165.12 (16) and 165.68 (15)° in one pair, and −164.66 (15) and −164.81 (15)° in the other pair. The crystal packing exhibits short intermolecular Cl⋯Cl contacts of 3.362 (1) Å.
of the title compound, CExperimental
Crystal data
|
Data collection: CrystalClear (Rigaku, 2005); cell CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2004
).
Supporting information
10.1107/S1600536809034084/cv2599sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809034084/cv2599Isup2.hkl
A mixture of 3,4-dichlorobenzaldehyde(5 mmol) and 2-(prop-1-en-2-yl) naphthalene benzaldehyde (10 mmol) was dissolved in aqueous ethanol (100 ml, 60% v/v). The solution of KOH (4.0 ml, 7.1 mmol) was slowly added and stirred at 323 K for 5 h. The resulting mixture was neutralized with 2 N HCl. The precipitate filtered off, washed with water, and crystallized from dichloromethane-methanol (1/4 v/v) to obtain (I) (m.p.426–427k). Crystals suitable for X-ray analysis were grown by slow evaporation of a methanol-dichloromethane (4/1 v/v) solution at room temperature over a period of 16 d.
All H atoms were placed geometrically (C—H = 0.95 Å), and refined as riding with Uiso(H) = 1.2Ueq(C).
Data collection: CrystalClear (Rigaku, 2005); cell
CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: CrystalStructure (Rigaku/MSC, 2004). ![]() | Fig. 1. Four independent molecules of (I), shown with 30% probability displacement ellipsoids (arbitrary spheres for H atoms). |
C19H12Cl2O | Z = 8 |
Mr = 327.19 | F(000) = 1344 |
Triclinic, P1 | Dx = 1.516 Mg m−3 |
Hall symbol: -P 1 | Melting point: 426-427 K K |
a = 7.5273 (10) Å | Mo Kα radiation, λ = 0.71070 Å |
b = 11.5212 (14) Å | Cell parameters from 4591 reflections |
c = 33.301 (4) Å | θ = 1.2–27.2° |
α = 92.338 (7)° | µ = 0.45 mm−1 |
β = 96.469 (7)° | T = 113 K |
γ = 90.125 (6)° | Block, yellow |
V = 2867.1 (6) Å3 | 0.36 × 0.34 × 0.28 mm |
Rigaku Saturn CCD area-detector diffractometer | 13067 independent reflections |
Radiation source: Rotating anode | 10135 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.023 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.9°, θmin = 1.9° |
ω and ϕ scans | h = −9→9 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −15→14 |
Tmin = 0.855, Tmax = 0.884 | l = −43→43 |
26590 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0577P)2 + 0.5613P] where P = (Fo2 + 2Fc2)/3 |
13067 reflections | (Δ/σ)max = 0.001 |
793 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
C19H12Cl2O | γ = 90.125 (6)° |
Mr = 327.19 | V = 2867.1 (6) Å3 |
Triclinic, P1 | Z = 8 |
a = 7.5273 (10) Å | Mo Kα radiation |
b = 11.5212 (14) Å | µ = 0.45 mm−1 |
c = 33.301 (4) Å | T = 113 K |
α = 92.338 (7)° | 0.36 × 0.34 × 0.28 mm |
β = 96.469 (7)° |
Rigaku Saturn CCD area-detector diffractometer | 13067 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 10135 reflections with I > 2σ(I) |
Tmin = 0.855, Tmax = 0.884 | Rint = 0.023 |
26590 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.37 e Å−3 |
13067 reflections | Δρmin = −0.44 e Å−3 |
793 parameters |
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 | ||
Cl1 | −0.00530 (6) | 0.47380 (4) | −0.209773 (11) | 0.02137 (10) | |
Cl2 | −0.18280 (6) | 0.22714 (4) | −0.206473 (12) | 0.02169 (10) | |
Cl3 | 0.48364 (6) | −0.02522 (3) | −0.207594 (11) | 0.02037 (9) | |
Cl4 | 0.32062 (6) | 0.22617 (3) | −0.204037 (11) | 0.02038 (9) | |
Cl5 | 0.80421 (6) | 0.47713 (3) | 0.292686 (11) | 0.02060 (9) | |
Cl6 | 0.97202 (6) | 0.22757 (4) | 0.295246 (12) | 0.02159 (10) | |
Cl7 | 0.29865 (6) | −0.02818 (3) | 0.291430 (11) | 0.02085 (9) | |
Cl8 | 0.47357 (6) | 0.22092 (3) | 0.293851 (12) | 0.02095 (9) | |
O1 | 0.27954 (17) | 0.60599 (10) | 0.01527 (3) | 0.0239 (3) | |
O2 | 0.78508 (17) | −0.10351 (10) | 0.01670 (3) | 0.0233 (3) | |
O3 | 0.73173 (17) | 0.60659 (10) | 0.51678 (3) | 0.0235 (3) | |
O4 | 0.23484 (17) | −0.10235 (10) | 0.51615 (3) | 0.0234 (3) | |
C1 | 0.2845 (2) | 0.50007 (14) | 0.01544 (5) | 0.0163 (3) | |
C2 | 0.2051 (2) | 0.42617 (14) | −0.01949 (5) | 0.0189 (3) | |
H2 | 0.1829 | 0.3461 | −0.0161 | 0.023* | |
C3 | 0.1646 (2) | 0.47136 (14) | −0.05569 (5) | 0.0165 (3) | |
H3 | 0.1938 | 0.5509 | −0.0580 | 0.020* | |
C4 | 0.0788 (2) | 0.40906 (13) | −0.09209 (4) | 0.0152 (3) | |
C5 | 0.0749 (2) | 0.46242 (14) | −0.12922 (5) | 0.0159 (3) | |
H5 | 0.1267 | 0.5374 | −0.1303 | 0.019* | |
C6 | −0.0041 (2) | 0.40647 (13) | −0.16443 (4) | 0.0153 (3) | |
C7 | −0.0807 (2) | 0.29715 (13) | −0.16304 (4) | 0.0156 (3) | |
C8 | −0.0789 (2) | 0.24368 (14) | −0.12628 (5) | 0.0168 (3) | |
H8 | −0.1328 | 0.1694 | −0.1253 | 0.020* | |
C9 | 0.0016 (2) | 0.29893 (13) | −0.09119 (5) | 0.0165 (3) | |
H9 | 0.0045 | 0.2616 | −0.0662 | 0.020* | |
C10 | 0.3765 (2) | 0.49862 (13) | 0.08884 (5) | 0.0147 (3) | |
H10 | 0.3281 | 0.5745 | 0.0907 | 0.018* | |
C11 | 0.3692 (2) | 0.44034 (13) | 0.05170 (4) | 0.0153 (3) | |
C12 | 0.4422 (2) | 0.32751 (14) | 0.04866 (5) | 0.0181 (3) | |
H12 | 0.4337 | 0.2865 | 0.0232 | 0.022* | |
C13 | 0.5251 (2) | 0.27731 (14) | 0.08231 (5) | 0.0177 (3) | |
H13 | 0.5781 | 0.2030 | 0.0797 | 0.021* | |
C14 | 0.5329 (2) | 0.33478 (13) | 0.12094 (5) | 0.0150 (3) | |
C15 | 0.4553 (2) | 0.44688 (13) | 0.12426 (5) | 0.0148 (3) | |
C16 | 0.4588 (2) | 0.50344 (14) | 0.16303 (5) | 0.0174 (3) | |
H16 | 0.4064 | 0.5779 | 0.1656 | 0.021* | |
C17 | 0.5371 (2) | 0.45125 (15) | 0.19667 (5) | 0.0204 (3) | |
H17 | 0.5388 | 0.4898 | 0.2225 | 0.024* | |
C18 | 0.6154 (2) | 0.34067 (15) | 0.19333 (5) | 0.0214 (4) | |
H18 | 0.6694 | 0.3054 | 0.2169 | 0.026* | |
C19 | 0.6144 (2) | 0.28379 (14) | 0.15648 (5) | 0.0187 (3) | |
H19 | 0.6685 | 0.2096 | 0.1546 | 0.022* | |
C20 | 0.7887 (2) | 0.00248 (14) | 0.01717 (5) | 0.0171 (3) | |
C21 | 0.7086 (2) | 0.06819 (14) | −0.01763 (5) | 0.0189 (3) | |
H21 | 0.6868 | 0.1490 | −0.0142 | 0.023* | |
C22 | 0.6668 (2) | 0.01464 (14) | −0.05379 (5) | 0.0165 (3) | |
H22 | 0.6953 | −0.0654 | −0.0562 | 0.020* | |
C23 | 0.5808 (2) | 0.06863 (13) | −0.09011 (4) | 0.0149 (3) | |
C24 | 0.5721 (2) | 0.00596 (13) | −0.12721 (5) | 0.0151 (3) | |
H24 | 0.6211 | −0.0699 | −0.1284 | 0.018* | |
C25 | 0.4922 (2) | 0.05398 (13) | −0.16234 (4) | 0.0153 (3) | |
C26 | 0.4207 (2) | 0.16467 (13) | −0.16086 (4) | 0.0154 (3) | |
C27 | 0.4271 (2) | 0.22752 (14) | −0.12403 (5) | 0.0167 (3) | |
H27 | 0.3765 | 0.3029 | −0.1230 | 0.020* | |
C28 | 0.5071 (2) | 0.18000 (14) | −0.08905 (5) | 0.0167 (3) | |
H28 | 0.5120 | 0.2234 | −0.0641 | 0.020* | |
C29 | 0.8808 (2) | 0.02162 (13) | 0.09061 (5) | 0.0149 (3) | |
H29 | 0.8327 | −0.0540 | 0.0925 | 0.018* | |
C30 | 0.8731 (2) | 0.07115 (13) | 0.05331 (4) | 0.0154 (3) | |
C31 | 0.9453 (2) | 0.18380 (14) | 0.05041 (5) | 0.0180 (3) | |
H31 | 0.9365 | 0.2188 | 0.0249 | 0.022* | |
C32 | 1.0276 (2) | 0.24257 (14) | 0.08396 (5) | 0.0172 (3) | |
H32 | 1.0799 | 0.3166 | 0.0814 | 0.021* | |
C33 | 1.0355 (2) | 0.19405 (13) | 0.12265 (5) | 0.0155 (3) | |
C34 | 0.9595 (2) | 0.08219 (13) | 0.12592 (4) | 0.0149 (3) | |
C35 | 0.9641 (2) | 0.03472 (14) | 0.16475 (5) | 0.0174 (3) | |
H35 | 0.9130 | −0.0397 | 0.1674 | 0.021* | |
C36 | 1.0415 (2) | 0.09555 (15) | 0.19838 (5) | 0.0215 (3) | |
H36 | 1.0433 | 0.0632 | 0.2242 | 0.026* | |
C37 | 1.1188 (2) | 0.20578 (15) | 0.19500 (5) | 0.0221 (4) | |
H37 | 1.1727 | 0.2470 | 0.2186 | 0.027* | |
C38 | 1.1168 (2) | 0.25401 (14) | 0.15806 (5) | 0.0190 (3) | |
H38 | 1.1702 | 0.3281 | 0.1561 | 0.023* | |
C39 | 0.7281 (2) | 0.50044 (14) | 0.51735 (5) | 0.0170 (3) | |
C40 | 0.7726 (2) | 0.42625 (14) | 0.48243 (5) | 0.0189 (3) | |
H40 | 0.7965 | 0.3461 | 0.4858 | 0.023* | |
C41 | 0.7792 (2) | 0.47129 (14) | 0.44642 (5) | 0.0164 (3) | |
H41 | 0.7498 | 0.5511 | 0.4441 | 0.020* | |
C42 | 0.8279 (2) | 0.40890 (13) | 0.40996 (4) | 0.0147 (3) | |
C43 | 0.7975 (2) | 0.46376 (13) | 0.37293 (5) | 0.0154 (3) | |
H43 | 0.7472 | 0.5393 | 0.3720 | 0.019* | |
C44 | 0.8410 (2) | 0.40780 (14) | 0.33775 (4) | 0.0154 (3) | |
C45 | 0.9157 (2) | 0.29754 (14) | 0.33880 (5) | 0.0157 (3) | |
C46 | 0.9474 (2) | 0.24305 (14) | 0.37545 (5) | 0.0168 (3) | |
H46 | 0.9995 | 0.1680 | 0.3763 | 0.020* | |
C47 | 0.9029 (2) | 0.29816 (14) | 0.41062 (5) | 0.0168 (3) | |
H47 | 0.9238 | 0.2602 | 0.4355 | 0.020* | |
C48 | 0.7104 (2) | 0.49980 (13) | 0.59074 (5) | 0.0149 (3) | |
H48 | 0.7608 | 0.5758 | 0.5924 | 0.018* | |
C49 | 0.6802 (2) | 0.44107 (13) | 0.55364 (4) | 0.0153 (3) | |
C50 | 0.6039 (2) | 0.32813 (14) | 0.55080 (5) | 0.0175 (3) | |
H50 | 0.5860 | 0.2869 | 0.5254 | 0.021* | |
C51 | 0.5557 (2) | 0.27817 (14) | 0.58458 (5) | 0.0177 (3) | |
H51 | 0.5006 | 0.2036 | 0.5822 | 0.021* | |
C52 | 0.5868 (2) | 0.33593 (13) | 0.62308 (5) | 0.0155 (3) | |
C53 | 0.6675 (2) | 0.44834 (13) | 0.62628 (5) | 0.0146 (3) | |
C54 | 0.7031 (2) | 0.50529 (14) | 0.66494 (5) | 0.0183 (3) | |
H54 | 0.7571 | 0.5802 | 0.6674 | 0.022* | |
C55 | 0.6602 (2) | 0.45286 (15) | 0.69874 (5) | 0.0213 (3) | |
H55 | 0.6856 | 0.4914 | 0.7245 | 0.026* | |
C56 | 0.5787 (2) | 0.34214 (15) | 0.69557 (5) | 0.0227 (4) | |
H56 | 0.5489 | 0.3068 | 0.7192 | 0.027* | |
C57 | 0.5420 (2) | 0.28511 (14) | 0.65881 (5) | 0.0192 (3) | |
H57 | 0.4861 | 0.2108 | 0.6571 | 0.023* | |
C58 | 0.2305 (2) | 0.00346 (14) | 0.51642 (5) | 0.0172 (3) | |
C59 | 0.2745 (2) | 0.06893 (14) | 0.48147 (5) | 0.0188 (3) | |
H59 | 0.2994 | 0.1498 | 0.4848 | 0.023* | |
C60 | 0.2794 (2) | 0.01502 (14) | 0.44534 (5) | 0.0168 (3) | |
H60 | 0.2490 | −0.0653 | 0.4431 | 0.020* | |
C61 | 0.3273 (2) | 0.06839 (13) | 0.40872 (4) | 0.0154 (3) | |
C62 | 0.2955 (2) | 0.00500 (14) | 0.37185 (5) | 0.0158 (3) | |
H62 | 0.2441 | −0.0706 | 0.3711 | 0.019* | |
C63 | 0.3385 (2) | 0.05196 (14) | 0.33638 (4) | 0.0158 (3) | |
C64 | 0.4154 (2) | 0.16158 (14) | 0.33743 (4) | 0.0158 (3) | |
C65 | 0.4487 (2) | 0.22523 (14) | 0.37399 (5) | 0.0169 (3) | |
H65 | 0.5018 | 0.3003 | 0.3747 | 0.020* | |
C66 | 0.4045 (2) | 0.17903 (13) | 0.40931 (5) | 0.0166 (3) | |
H66 | 0.4268 | 0.2229 | 0.4342 | 0.020* | |
C67 | 0.2121 (2) | 0.02260 (13) | 0.58983 (5) | 0.0149 (3) | |
H67 | 0.2623 | −0.0528 | 0.5917 | 0.018* | |
C68 | 0.1818 (2) | 0.07219 (13) | 0.55265 (4) | 0.0155 (3) | |
C69 | 0.1058 (2) | 0.18394 (14) | 0.54959 (5) | 0.0177 (3) | |
H69 | 0.0885 | 0.2187 | 0.5241 | 0.021* | |
C70 | 0.0567 (2) | 0.24240 (14) | 0.58322 (5) | 0.0172 (3) | |
H70 | 0.0012 | 0.3161 | 0.5806 | 0.021* | |
C71 | 0.0880 (2) | 0.19411 (13) | 0.62188 (5) | 0.0154 (3) | |
C72 | 0.1689 (2) | 0.08319 (13) | 0.62524 (4) | 0.0142 (3) | |
C73 | 0.2038 (2) | 0.03555 (14) | 0.66403 (5) | 0.0176 (3) | |
H73 | 0.2579 | −0.0386 | 0.6666 | 0.021* | |
C74 | 0.1598 (2) | 0.09629 (15) | 0.69779 (5) | 0.0208 (3) | |
H74 | 0.1846 | 0.0642 | 0.7236 | 0.025* | |
C75 | 0.0781 (2) | 0.20611 (15) | 0.69434 (5) | 0.0212 (3) | |
H75 | 0.0481 | 0.2473 | 0.7179 | 0.025* | |
C76 | 0.0416 (2) | 0.25385 (14) | 0.65738 (5) | 0.0185 (3) | |
H76 | −0.0151 | 0.3273 | 0.6554 | 0.022* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0263 (2) | 0.0234 (2) | 0.01441 (18) | −0.00252 (17) | 0.00050 (15) | 0.00574 (14) |
Cl2 | 0.0233 (2) | 0.0231 (2) | 0.01752 (18) | −0.00437 (16) | −0.00162 (15) | −0.00247 (14) |
Cl3 | 0.0270 (2) | 0.0200 (2) | 0.01394 (17) | 0.00279 (16) | 0.00222 (15) | −0.00196 (14) |
Cl4 | 0.0227 (2) | 0.0206 (2) | 0.01712 (18) | 0.00368 (16) | −0.00198 (15) | 0.00331 (14) |
Cl5 | 0.0267 (2) | 0.0216 (2) | 0.01365 (17) | 0.00192 (16) | 0.00179 (15) | 0.00411 (14) |
Cl6 | 0.0249 (2) | 0.0224 (2) | 0.01806 (18) | 0.00308 (16) | 0.00624 (15) | −0.00309 (14) |
Cl7 | 0.0281 (2) | 0.0203 (2) | 0.01389 (17) | −0.00261 (16) | 0.00228 (15) | −0.00151 (14) |
Cl8 | 0.0238 (2) | 0.0222 (2) | 0.01798 (18) | −0.00305 (16) | 0.00538 (15) | 0.00522 (14) |
O1 | 0.0347 (7) | 0.0173 (6) | 0.0191 (6) | −0.0015 (5) | −0.0002 (5) | 0.0021 (4) |
O2 | 0.0332 (7) | 0.0174 (6) | 0.0184 (6) | 0.0001 (5) | −0.0009 (5) | 0.0001 (4) |
O3 | 0.0353 (7) | 0.0173 (6) | 0.0183 (6) | 0.0016 (5) | 0.0048 (5) | 0.0015 (4) |
O4 | 0.0342 (7) | 0.0177 (6) | 0.0183 (6) | −0.0009 (5) | 0.0041 (5) | 0.0002 (4) |
C1 | 0.0172 (8) | 0.0176 (8) | 0.0142 (7) | −0.0026 (6) | 0.0023 (6) | 0.0018 (6) |
C2 | 0.0214 (9) | 0.0175 (8) | 0.0176 (8) | −0.0031 (7) | 0.0007 (6) | 0.0010 (6) |
C3 | 0.0161 (8) | 0.0168 (8) | 0.0165 (7) | −0.0007 (6) | 0.0013 (6) | 0.0000 (6) |
C4 | 0.0131 (8) | 0.0165 (8) | 0.0160 (7) | 0.0014 (6) | 0.0017 (6) | 0.0011 (6) |
C5 | 0.0140 (8) | 0.0157 (7) | 0.0180 (7) | −0.0008 (6) | 0.0018 (6) | 0.0015 (6) |
C6 | 0.0146 (8) | 0.0180 (8) | 0.0136 (7) | 0.0017 (6) | 0.0022 (6) | 0.0036 (6) |
C7 | 0.0137 (8) | 0.0176 (8) | 0.0151 (7) | 0.0013 (6) | 0.0008 (6) | −0.0015 (6) |
C8 | 0.0170 (8) | 0.0142 (7) | 0.0198 (7) | −0.0015 (6) | 0.0041 (6) | 0.0017 (6) |
C9 | 0.0181 (8) | 0.0167 (8) | 0.0152 (7) | 0.0005 (6) | 0.0030 (6) | 0.0030 (6) |
C10 | 0.0132 (8) | 0.0133 (7) | 0.0174 (7) | −0.0008 (6) | 0.0014 (6) | 0.0005 (6) |
C11 | 0.0155 (8) | 0.0164 (8) | 0.0143 (7) | −0.0026 (6) | 0.0018 (6) | 0.0027 (6) |
C12 | 0.0189 (9) | 0.0188 (8) | 0.0167 (7) | −0.0021 (7) | 0.0042 (6) | −0.0029 (6) |
C13 | 0.0175 (8) | 0.0151 (8) | 0.0211 (8) | 0.0008 (6) | 0.0050 (6) | −0.0002 (6) |
C14 | 0.0110 (8) | 0.0150 (7) | 0.0194 (7) | −0.0019 (6) | 0.0029 (6) | 0.0011 (6) |
C15 | 0.0125 (8) | 0.0159 (7) | 0.0160 (7) | −0.0015 (6) | 0.0017 (6) | 0.0015 (6) |
C16 | 0.0161 (8) | 0.0184 (8) | 0.0174 (7) | −0.0002 (6) | 0.0016 (6) | −0.0020 (6) |
C17 | 0.0201 (9) | 0.0249 (9) | 0.0159 (7) | −0.0007 (7) | 0.0006 (6) | −0.0002 (6) |
C18 | 0.0189 (9) | 0.0251 (9) | 0.0196 (8) | −0.0016 (7) | −0.0025 (6) | 0.0061 (6) |
C19 | 0.0162 (8) | 0.0167 (8) | 0.0234 (8) | 0.0006 (6) | 0.0015 (6) | 0.0042 (6) |
C20 | 0.0173 (8) | 0.0193 (8) | 0.0147 (7) | 0.0020 (6) | 0.0021 (6) | 0.0014 (6) |
C21 | 0.0214 (9) | 0.0174 (8) | 0.0177 (8) | 0.0024 (7) | 0.0008 (6) | 0.0014 (6) |
C22 | 0.0157 (8) | 0.0165 (8) | 0.0175 (7) | −0.0002 (6) | 0.0015 (6) | 0.0030 (6) |
C23 | 0.0136 (8) | 0.0162 (7) | 0.0150 (7) | −0.0014 (6) | 0.0013 (6) | 0.0018 (6) |
C24 | 0.0145 (8) | 0.0145 (7) | 0.0164 (7) | −0.0005 (6) | 0.0022 (6) | 0.0011 (6) |
C25 | 0.0148 (8) | 0.0171 (8) | 0.0142 (7) | −0.0027 (6) | 0.0030 (6) | −0.0013 (6) |
C26 | 0.0131 (8) | 0.0175 (8) | 0.0155 (7) | −0.0007 (6) | 0.0003 (6) | 0.0030 (6) |
C27 | 0.0152 (8) | 0.0144 (7) | 0.0207 (8) | 0.0012 (6) | 0.0028 (6) | 0.0002 (6) |
C28 | 0.0175 (8) | 0.0171 (8) | 0.0155 (7) | −0.0003 (6) | 0.0022 (6) | −0.0012 (6) |
C29 | 0.0137 (8) | 0.0139 (7) | 0.0174 (7) | 0.0007 (6) | 0.0022 (6) | 0.0013 (6) |
C30 | 0.0142 (8) | 0.0166 (8) | 0.0154 (7) | 0.0022 (6) | 0.0020 (6) | 0.0006 (6) |
C31 | 0.0204 (9) | 0.0193 (8) | 0.0152 (7) | 0.0017 (7) | 0.0046 (6) | 0.0046 (6) |
C32 | 0.0167 (8) | 0.0155 (8) | 0.0205 (8) | −0.0009 (6) | 0.0061 (6) | 0.0021 (6) |
C33 | 0.0127 (8) | 0.0161 (7) | 0.0178 (7) | 0.0011 (6) | 0.0026 (6) | 0.0013 (6) |
C34 | 0.0132 (8) | 0.0162 (7) | 0.0156 (7) | 0.0021 (6) | 0.0023 (6) | 0.0009 (6) |
C35 | 0.0157 (8) | 0.0182 (8) | 0.0186 (8) | 0.0020 (6) | 0.0021 (6) | 0.0028 (6) |
C36 | 0.0236 (9) | 0.0249 (9) | 0.0158 (7) | 0.0036 (7) | 0.0012 (6) | 0.0018 (6) |
C37 | 0.0209 (9) | 0.0256 (9) | 0.0187 (8) | 0.0019 (7) | −0.0013 (6) | −0.0034 (6) |
C38 | 0.0163 (8) | 0.0183 (8) | 0.0220 (8) | −0.0007 (6) | 0.0014 (6) | −0.0021 (6) |
C39 | 0.0186 (8) | 0.0180 (8) | 0.0142 (7) | 0.0018 (6) | 0.0000 (6) | 0.0017 (6) |
C40 | 0.0210 (9) | 0.0182 (8) | 0.0179 (8) | 0.0035 (7) | 0.0033 (6) | 0.0015 (6) |
C41 | 0.0156 (8) | 0.0165 (8) | 0.0169 (7) | 0.0001 (6) | 0.0020 (6) | −0.0001 (6) |
C42 | 0.0140 (8) | 0.0156 (7) | 0.0144 (7) | −0.0027 (6) | 0.0014 (6) | 0.0008 (6) |
C43 | 0.0140 (8) | 0.0152 (7) | 0.0173 (7) | −0.0003 (6) | 0.0018 (6) | 0.0022 (6) |
C44 | 0.0144 (8) | 0.0178 (8) | 0.0140 (7) | −0.0015 (6) | 0.0008 (6) | 0.0038 (6) |
C45 | 0.0141 (8) | 0.0175 (8) | 0.0155 (7) | −0.0010 (6) | 0.0031 (6) | −0.0024 (6) |
C46 | 0.0155 (8) | 0.0147 (7) | 0.0200 (8) | 0.0004 (6) | 0.0006 (6) | 0.0012 (6) |
C47 | 0.0180 (8) | 0.0172 (8) | 0.0150 (7) | −0.0006 (6) | 0.0000 (6) | 0.0032 (6) |
C48 | 0.0144 (8) | 0.0135 (7) | 0.0167 (7) | 0.0007 (6) | 0.0008 (6) | 0.0014 (6) |
C49 | 0.0136 (8) | 0.0173 (8) | 0.0151 (7) | 0.0024 (6) | 0.0010 (6) | 0.0019 (6) |
C50 | 0.0175 (8) | 0.0175 (8) | 0.0166 (7) | 0.0021 (6) | −0.0013 (6) | −0.0023 (6) |
C51 | 0.0142 (8) | 0.0152 (8) | 0.0230 (8) | −0.0015 (6) | −0.0008 (6) | 0.0008 (6) |
C52 | 0.0117 (8) | 0.0163 (8) | 0.0185 (7) | 0.0019 (6) | 0.0008 (6) | 0.0028 (6) |
C53 | 0.0107 (8) | 0.0172 (8) | 0.0161 (7) | 0.0014 (6) | 0.0013 (6) | 0.0014 (6) |
C54 | 0.0165 (8) | 0.0198 (8) | 0.0182 (8) | 0.0005 (6) | 0.0006 (6) | 0.0002 (6) |
C55 | 0.0203 (9) | 0.0295 (9) | 0.0140 (7) | 0.0033 (7) | 0.0015 (6) | −0.0007 (6) |
C56 | 0.0220 (9) | 0.0278 (9) | 0.0195 (8) | 0.0033 (7) | 0.0050 (7) | 0.0087 (7) |
C57 | 0.0158 (8) | 0.0185 (8) | 0.0241 (8) | 0.0009 (6) | 0.0032 (6) | 0.0069 (6) |
C58 | 0.0179 (8) | 0.0193 (8) | 0.0139 (7) | −0.0020 (6) | −0.0005 (6) | 0.0010 (6) |
C59 | 0.0212 (9) | 0.0182 (8) | 0.0171 (7) | −0.0031 (7) | 0.0024 (6) | 0.0017 (6) |
C60 | 0.0162 (8) | 0.0174 (8) | 0.0170 (7) | −0.0002 (6) | 0.0014 (6) | 0.0024 (6) |
C61 | 0.0130 (8) | 0.0172 (8) | 0.0160 (7) | 0.0014 (6) | 0.0016 (6) | 0.0022 (6) |
C62 | 0.0140 (8) | 0.0152 (7) | 0.0182 (7) | −0.0006 (6) | 0.0012 (6) | 0.0016 (6) |
C63 | 0.0146 (8) | 0.0183 (8) | 0.0142 (7) | 0.0019 (6) | 0.0010 (6) | −0.0011 (6) |
C64 | 0.0141 (8) | 0.0188 (8) | 0.0151 (7) | 0.0013 (6) | 0.0031 (6) | 0.0054 (6) |
C65 | 0.0159 (8) | 0.0145 (7) | 0.0200 (8) | −0.0015 (6) | 0.0007 (6) | 0.0018 (6) |
C66 | 0.0175 (8) | 0.0164 (8) | 0.0153 (7) | 0.0003 (6) | −0.0001 (6) | −0.0006 (6) |
C67 | 0.0141 (8) | 0.0139 (7) | 0.0167 (7) | −0.0012 (6) | 0.0006 (6) | 0.0017 (6) |
C68 | 0.0154 (8) | 0.0165 (8) | 0.0146 (7) | −0.0034 (6) | 0.0011 (6) | 0.0008 (6) |
C69 | 0.0182 (8) | 0.0185 (8) | 0.0159 (7) | −0.0021 (6) | −0.0016 (6) | 0.0042 (6) |
C70 | 0.0152 (8) | 0.0152 (8) | 0.0208 (8) | 0.0016 (6) | −0.0006 (6) | 0.0029 (6) |
C71 | 0.0115 (8) | 0.0165 (8) | 0.0182 (7) | −0.0020 (6) | 0.0005 (6) | 0.0018 (6) |
C72 | 0.0109 (8) | 0.0160 (7) | 0.0157 (7) | −0.0022 (6) | 0.0007 (6) | 0.0021 (6) |
C73 | 0.0170 (8) | 0.0183 (8) | 0.0173 (7) | −0.0001 (6) | 0.0007 (6) | 0.0030 (6) |
C74 | 0.0240 (9) | 0.0232 (8) | 0.0150 (7) | −0.0023 (7) | 0.0012 (6) | 0.0025 (6) |
C75 | 0.0207 (9) | 0.0238 (9) | 0.0194 (8) | −0.0020 (7) | 0.0052 (6) | −0.0036 (6) |
C76 | 0.0161 (8) | 0.0165 (8) | 0.0226 (8) | 0.0003 (6) | 0.0024 (6) | −0.0013 (6) |
Cl1—C6 | 1.7246 (15) | C35—H35 | 0.9500 |
Cl2—C7 | 1.7275 (16) | C36—C37 | 1.409 (2) |
Cl3—C25 | 1.7244 (15) | C36—H36 | 0.9500 |
Cl4—C26 | 1.7258 (15) | C37—C38 | 1.369 (2) |
Cl5—C44 | 1.7239 (15) | C37—H37 | 0.9500 |
Cl6—C45 | 1.7255 (16) | C38—H38 | 0.9500 |
Cl7—C63 | 1.7229 (16) | C39—C40 | 1.484 (2) |
Cl8—C64 | 1.7286 (15) | C39—C49 | 1.491 (2) |
O1—C1 | 1.2212 (19) | C40—C41 | 1.332 (2) |
O2—C20 | 1.2209 (19) | C40—H40 | 0.9500 |
O3—C39 | 1.2241 (19) | C41—C42 | 1.468 (2) |
O4—C58 | 1.2193 (19) | C41—H41 | 0.9500 |
C1—C2 | 1.482 (2) | C42—C47 | 1.396 (2) |
C1—C11 | 1.495 (2) | C42—C43 | 1.405 (2) |
C2—C3 | 1.337 (2) | C43—C44 | 1.386 (2) |
C2—H2 | 0.9500 | C43—H43 | 0.9500 |
C3—C4 | 1.467 (2) | C44—C45 | 1.390 (2) |
C3—H3 | 0.9500 | C45—C46 | 1.392 (2) |
C4—C9 | 1.397 (2) | C46—C47 | 1.384 (2) |
C4—C5 | 1.400 (2) | C46—H46 | 0.9500 |
C5—C6 | 1.387 (2) | C47—H47 | 0.9500 |
C5—H5 | 0.9500 | C48—C49 | 1.380 (2) |
C6—C7 | 1.389 (2) | C48—C53 | 1.414 (2) |
C7—C8 | 1.391 (2) | C48—H48 | 0.9500 |
C8—C9 | 1.384 (2) | C49—C50 | 1.417 (2) |
C8—H8 | 0.9500 | C50—C51 | 1.368 (2) |
C9—H9 | 0.9500 | C50—H50 | 0.9500 |
C10—C11 | 1.379 (2) | C51—C52 | 1.415 (2) |
C10—C15 | 1.414 (2) | C51—H51 | 0.9500 |
C10—H10 | 0.9500 | C52—C57 | 1.421 (2) |
C11—C12 | 1.417 (2) | C52—C53 | 1.424 (2) |
C12—C13 | 1.370 (2) | C53—C54 | 1.419 (2) |
C12—H12 | 0.9500 | C54—C55 | 1.369 (2) |
C13—C14 | 1.418 (2) | C54—H54 | 0.9500 |
C13—H13 | 0.9500 | C55—C56 | 1.409 (2) |
C14—C19 | 1.420 (2) | C55—H55 | 0.9500 |
C14—C15 | 1.424 (2) | C56—C57 | 1.365 (2) |
C15—C16 | 1.420 (2) | C56—H56 | 0.9500 |
C16—C17 | 1.368 (2) | C57—H57 | 0.9500 |
C16—H16 | 0.9500 | C58—C59 | 1.480 (2) |
C17—C18 | 1.411 (2) | C58—C68 | 1.497 (2) |
C17—H17 | 0.9500 | C59—C60 | 1.336 (2) |
C18—C19 | 1.366 (2) | C59—H59 | 0.9500 |
C18—H18 | 0.9500 | C60—C61 | 1.468 (2) |
C19—H19 | 0.9500 | C60—H60 | 0.9500 |
C20—C21 | 1.482 (2) | C61—C66 | 1.398 (2) |
C20—C30 | 1.492 (2) | C61—C62 | 1.399 (2) |
C21—C22 | 1.335 (2) | C62—C63 | 1.389 (2) |
C21—H21 | 0.9500 | C62—H62 | 0.9500 |
C22—C23 | 1.468 (2) | C63—C64 | 1.386 (2) |
C22—H22 | 0.9500 | C64—C65 | 1.393 (2) |
C23—C28 | 1.400 (2) | C65—C66 | 1.384 (2) |
C23—C24 | 1.400 (2) | C65—H65 | 0.9500 |
C24—C25 | 1.390 (2) | C66—H66 | 0.9500 |
C24—H24 | 0.9500 | C67—C68 | 1.381 (2) |
C25—C26 | 1.386 (2) | C67—C72 | 1.415 (2) |
C26—C27 | 1.395 (2) | C67—H67 | 0.9500 |
C27—C28 | 1.384 (2) | C68—C69 | 1.413 (2) |
C27—H27 | 0.9500 | C69—C70 | 1.370 (2) |
C28—H28 | 0.9500 | C69—H69 | 0.9500 |
C29—C30 | 1.383 (2) | C70—C71 | 1.419 (2) |
C29—C34 | 1.413 (2) | C70—H70 | 0.9500 |
C29—H29 | 0.9500 | C71—C72 | 1.420 (2) |
C30—C31 | 1.417 (2) | C71—C76 | 1.421 (2) |
C31—C32 | 1.368 (2) | C72—C73 | 1.422 (2) |
C31—H31 | 0.9500 | C73—C74 | 1.373 (2) |
C32—C33 | 1.420 (2) | C73—H73 | 0.9500 |
C32—H32 | 0.9500 | C74—C75 | 1.411 (2) |
C33—C38 | 1.418 (2) | C74—H74 | 0.9500 |
C33—C34 | 1.422 (2) | C75—C76 | 1.368 (2) |
C34—C35 | 1.421 (2) | C75—H75 | 0.9500 |
C35—C36 | 1.369 (2) | C76—H76 | 0.9500 |
O1—C1—C2 | 121.90 (14) | O3—C39—C40 | 121.64 (14) |
O1—C1—C11 | 120.52 (14) | O3—C39—C49 | 120.78 (14) |
C2—C1—C11 | 117.57 (13) | C40—C39—C49 | 117.58 (13) |
C3—C2—C1 | 120.43 (15) | C41—C40—C39 | 120.45 (15) |
C3—C2—H2 | 119.8 | C41—C40—H40 | 119.8 |
C1—C2—H2 | 119.8 | C39—C40—H40 | 119.8 |
C2—C3—C4 | 125.77 (15) | C40—C41—C42 | 125.94 (15) |
C2—C3—H3 | 117.1 | C40—C41—H41 | 117.0 |
C4—C3—H3 | 117.1 | C42—C41—H41 | 117.0 |
C9—C4—C5 | 118.88 (14) | C47—C42—C43 | 118.94 (14) |
C9—C4—C3 | 122.70 (14) | C47—C42—C41 | 122.89 (13) |
C5—C4—C3 | 118.42 (14) | C43—C42—C41 | 118.16 (14) |
C6—C5—C4 | 120.36 (14) | C44—C43—C42 | 120.05 (14) |
C6—C5—H5 | 119.8 | C44—C43—H43 | 120.0 |
C4—C5—H5 | 119.8 | C42—C43—H43 | 120.0 |
C5—C6—C7 | 120.10 (14) | C43—C44—C45 | 120.46 (13) |
C5—C6—Cl1 | 119.34 (12) | C43—C44—Cl5 | 119.29 (12) |
C7—C6—Cl1 | 120.56 (12) | C45—C44—Cl5 | 120.24 (12) |
C6—C7—C8 | 120.04 (14) | C44—C45—C46 | 119.78 (14) |
C6—C7—Cl2 | 120.74 (12) | C44—C45—Cl6 | 120.85 (12) |
C8—C7—Cl2 | 119.21 (12) | C46—C45—Cl6 | 119.37 (12) |
C9—C8—C7 | 119.89 (15) | C47—C46—C45 | 119.99 (15) |
C9—C8—H8 | 120.1 | C47—C46—H46 | 120.0 |
C7—C8—H8 | 120.1 | C45—C46—H46 | 120.0 |
C8—C9—C4 | 120.72 (14) | C46—C47—C42 | 120.77 (14) |
C8—C9—H9 | 119.6 | C46—C47—H47 | 119.6 |
C4—C9—H9 | 119.6 | C42—C47—H47 | 119.6 |
C11—C10—C15 | 120.81 (14) | C49—C48—C53 | 120.84 (14) |
C11—C10—H10 | 119.6 | C49—C48—H48 | 119.6 |
C15—C10—H10 | 119.6 | C53—C48—H48 | 119.6 |
C10—C11—C12 | 119.97 (14) | C48—C49—C50 | 119.95 (14) |
C10—C11—C1 | 118.11 (14) | C48—C49—C39 | 118.11 (14) |
C12—C11—C1 | 121.91 (14) | C50—C49—C39 | 121.93 (14) |
C13—C12—C11 | 120.29 (14) | C51—C50—C49 | 120.23 (14) |
C13—C12—H12 | 119.9 | C51—C50—H50 | 119.9 |
C11—C12—H12 | 119.9 | C49—C50—H50 | 119.9 |
C12—C13—C14 | 120.88 (15) | C50—C51—C52 | 121.00 (15) |
C12—C13—H13 | 119.6 | C50—C51—H51 | 119.5 |
C14—C13—H13 | 119.6 | C52—C51—H51 | 119.5 |
C13—C14—C19 | 122.14 (14) | C51—C52—C57 | 122.25 (15) |
C13—C14—C15 | 118.93 (14) | C51—C52—C53 | 119.02 (14) |
C19—C14—C15 | 118.93 (14) | C57—C52—C53 | 118.72 (14) |
C10—C15—C16 | 121.85 (14) | C48—C53—C54 | 121.89 (14) |
C10—C15—C14 | 119.05 (14) | C48—C53—C52 | 118.90 (14) |
C16—C15—C14 | 119.10 (14) | C54—C53—C52 | 119.21 (14) |
C17—C16—C15 | 120.36 (15) | C55—C54—C53 | 120.37 (15) |
C17—C16—H16 | 119.8 | C55—C54—H54 | 119.8 |
C15—C16—H16 | 119.8 | C53—C54—H54 | 119.8 |
C16—C17—C18 | 120.52 (15) | C54—C55—C56 | 120.47 (15) |
C16—C17—H17 | 119.7 | C54—C55—H55 | 119.8 |
C18—C17—H17 | 119.7 | C56—C55—H55 | 119.8 |
C19—C18—C17 | 120.64 (14) | C57—C56—C55 | 120.64 (15) |
C19—C18—H18 | 119.7 | C57—C56—H56 | 119.7 |
C17—C18—H18 | 119.7 | C55—C56—H56 | 119.7 |
C18—C19—C14 | 120.44 (15) | C56—C57—C52 | 120.57 (15) |
C18—C19—H19 | 119.8 | C56—C57—H57 | 119.7 |
C14—C19—H19 | 119.8 | C52—C57—H57 | 119.7 |
O2—C20—C21 | 121.80 (14) | O4—C58—C59 | 121.78 (15) |
O2—C20—C30 | 120.90 (14) | O4—C58—C68 | 120.78 (14) |
C21—C20—C30 | 117.30 (14) | C59—C58—C68 | 117.44 (14) |
C22—C21—C20 | 120.46 (15) | C60—C59—C58 | 120.44 (15) |
C22—C21—H21 | 119.8 | C60—C59—H59 | 119.8 |
C20—C21—H21 | 119.8 | C58—C59—H59 | 119.8 |
C21—C22—C23 | 125.74 (15) | C59—C60—C61 | 126.00 (15) |
C21—C22—H22 | 117.1 | C59—C60—H60 | 117.0 |
C23—C22—H22 | 117.1 | C61—C60—H60 | 117.0 |
C28—C23—C24 | 118.84 (13) | C66—C61—C62 | 118.95 (14) |
C28—C23—C22 | 122.59 (14) | C66—C61—C60 | 122.73 (14) |
C24—C23—C22 | 118.57 (14) | C62—C61—C60 | 118.31 (14) |
C25—C24—C23 | 120.42 (14) | C63—C62—C61 | 120.37 (14) |
C25—C24—H24 | 119.8 | C63—C62—H62 | 119.8 |
C23—C24—H24 | 119.8 | C61—C62—H62 | 119.8 |
C26—C25—C24 | 120.08 (14) | C64—C63—C62 | 120.05 (14) |
C26—C25—Cl3 | 120.54 (12) | C64—C63—Cl7 | 120.53 (12) |
C24—C25—Cl3 | 119.38 (12) | C62—C63—Cl7 | 119.41 (12) |
C25—C26—C27 | 120.03 (14) | C63—C64—C65 | 120.10 (14) |
C25—C26—Cl4 | 120.98 (12) | C63—C64—Cl8 | 120.92 (12) |
C27—C26—Cl4 | 118.99 (12) | C65—C64—Cl8 | 118.98 (12) |
C28—C27—C26 | 119.96 (14) | C66—C65—C64 | 119.95 (15) |
C28—C27—H27 | 120.0 | C66—C65—H65 | 120.0 |
C26—C27—H27 | 120.0 | C64—C65—H65 | 120.0 |
C27—C28—C23 | 120.66 (14) | C65—C66—C61 | 120.57 (14) |
C27—C28—H28 | 119.7 | C65—C66—H66 | 119.7 |
C23—C28—H28 | 119.7 | C61—C66—H66 | 119.7 |
C30—C29—C34 | 120.75 (14) | C68—C67—C72 | 120.57 (14) |
C30—C29—H29 | 119.6 | C68—C67—H67 | 119.7 |
C34—C29—H29 | 119.6 | C72—C67—H67 | 119.7 |
C29—C30—C31 | 119.72 (14) | C67—C68—C69 | 120.09 (14) |
C29—C30—C20 | 118.11 (14) | C67—C68—C58 | 117.86 (14) |
C31—C30—C20 | 122.17 (13) | C69—C68—C58 | 122.05 (13) |
C32—C31—C30 | 120.61 (14) | C70—C69—C68 | 120.37 (14) |
C32—C31—H31 | 119.7 | C70—C69—H69 | 119.8 |
C30—C31—H31 | 119.7 | C68—C69—H69 | 119.8 |
C31—C32—C33 | 120.68 (14) | C69—C70—C71 | 120.73 (15) |
C31—C32—H32 | 119.7 | C69—C70—H70 | 119.6 |
C33—C32—H32 | 119.7 | C71—C70—H70 | 119.6 |
C38—C33—C32 | 121.89 (15) | C70—C71—C72 | 119.03 (14) |
C38—C33—C34 | 119.14 (14) | C70—C71—C76 | 121.91 (14) |
C32—C33—C34 | 118.96 (14) | C72—C71—C76 | 119.06 (14) |
C29—C34—C35 | 121.81 (14) | C67—C72—C71 | 119.14 (13) |
C29—C34—C33 | 119.22 (14) | C67—C72—C73 | 121.65 (14) |
C35—C34—C33 | 118.97 (14) | C71—C72—C73 | 119.21 (14) |
C36—C35—C34 | 120.39 (15) | C74—C73—C72 | 120.26 (15) |
C36—C35—H35 | 119.8 | C74—C73—H73 | 119.9 |
C34—C35—H35 | 119.8 | C72—C73—H73 | 119.9 |
C35—C36—C37 | 120.54 (15) | C73—C74—C75 | 120.41 (15) |
C35—C36—H36 | 119.7 | C73—C74—H74 | 119.8 |
C37—C36—H36 | 119.7 | C75—C74—H74 | 119.8 |
C38—C37—C36 | 120.57 (15) | C76—C75—C74 | 120.67 (15) |
C38—C37—H37 | 119.7 | C76—C75—H75 | 119.7 |
C36—C37—H37 | 119.7 | C74—C75—H75 | 119.7 |
C37—C38—C33 | 120.38 (15) | C75—C76—C71 | 120.37 (15) |
C37—C38—H38 | 119.8 | C75—C76—H76 | 119.8 |
C33—C38—H38 | 119.8 | C71—C76—H76 | 119.8 |
O1—C1—C2—C3 | 16.4 (3) | O3—C39—C40—C41 | −14.9 (3) |
C11—C1—C2—C3 | −164.66 (15) | C49—C39—C40—C41 | 165.71 (15) |
C1—C2—C3—C4 | −177.23 (15) | C39—C40—C41—C42 | 177.56 (15) |
C2—C3—C4—C9 | 11.3 (3) | C40—C41—C42—C47 | −11.3 (3) |
C2—C3—C4—C5 | −168.55 (16) | C40—C41—C42—C43 | 168.90 (16) |
C9—C4—C5—C6 | −0.1 (2) | C47—C42—C43—C44 | 0.4 (2) |
C3—C4—C5—C6 | 179.73 (14) | C41—C42—C43—C44 | −179.80 (14) |
C4—C5—C6—C7 | 0.3 (2) | C42—C43—C44—C45 | −0.3 (2) |
C4—C5—C6—Cl1 | −179.48 (12) | C42—C43—C44—Cl5 | −179.52 (12) |
C5—C6—C7—C8 | 0.2 (2) | C43—C44—C45—C46 | −0.1 (2) |
Cl1—C6—C7—C8 | 179.99 (12) | Cl5—C44—C45—C46 | 179.02 (12) |
C5—C6—C7—Cl2 | 178.97 (12) | C43—C44—C45—Cl6 | −179.46 (12) |
Cl1—C6—C7—Cl2 | −1.26 (19) | Cl5—C44—C45—Cl6 | −0.3 (2) |
C6—C7—C8—C9 | −0.9 (2) | C44—C45—C46—C47 | 0.6 (2) |
Cl2—C7—C8—C9 | −179.68 (12) | Cl6—C45—C46—C47 | 179.97 (12) |
C7—C8—C9—C4 | 1.1 (2) | C45—C46—C47—C42 | −0.6 (2) |
C5—C4—C9—C8 | −0.6 (2) | C43—C42—C47—C46 | 0.1 (2) |
C3—C4—C9—C8 | 179.58 (15) | C41—C42—C47—C46 | −179.70 (15) |
C15—C10—C11—C12 | −0.5 (2) | C53—C48—C49—C50 | 0.5 (2) |
C15—C10—C11—C1 | −179.89 (14) | C53—C48—C49—C39 | 179.83 (14) |
O1—C1—C11—C10 | 25.3 (2) | O3—C39—C49—C48 | −25.8 (2) |
C2—C1—C11—C10 | −153.71 (15) | C40—C39—C49—C48 | 153.58 (15) |
O1—C1—C11—C12 | −154.15 (16) | O3—C39—C49—C50 | 153.49 (16) |
C2—C1—C11—C12 | 26.9 (2) | C40—C39—C49—C50 | −27.1 (2) |
C10—C11—C12—C13 | −2.0 (2) | C48—C49—C50—C51 | 1.7 (2) |
C1—C11—C12—C13 | 177.42 (15) | C39—C49—C50—C51 | −177.61 (15) |
C11—C12—C13—C14 | 2.7 (2) | C49—C50—C51—C52 | −2.3 (2) |
C12—C13—C14—C19 | 178.56 (15) | C50—C51—C52—C57 | −178.52 (15) |
C12—C13—C14—C15 | −0.9 (2) | C50—C51—C52—C53 | 0.8 (2) |
C11—C10—C15—C16 | −177.72 (15) | C49—C48—C53—C54 | 177.73 (14) |
C11—C10—C15—C14 | 2.2 (2) | C49—C48—C53—C52 | −2.0 (2) |
C13—C14—C15—C10 | −1.5 (2) | C51—C52—C53—C48 | 1.4 (2) |
C19—C14—C15—C10 | 179.02 (14) | C57—C52—C53—C48 | −179.30 (14) |
C13—C14—C15—C16 | 178.41 (14) | C51—C52—C53—C54 | −178.39 (14) |
C19—C14—C15—C16 | −1.1 (2) | C57—C52—C53—C54 | 0.9 (2) |
C10—C15—C16—C17 | −179.55 (15) | C48—C53—C54—C55 | −179.85 (15) |
C14—C15—C16—C17 | 0.6 (2) | C52—C53—C54—C55 | −0.1 (2) |
C15—C16—C17—C18 | 0.0 (3) | C53—C54—C55—C56 | −0.6 (2) |
C16—C17—C18—C19 | 0.0 (3) | C54—C55—C56—C57 | 0.4 (3) |
C17—C18—C19—C14 | −0.6 (3) | C55—C56—C57—C52 | 0.5 (3) |
C13—C14—C19—C18 | −178.40 (15) | C51—C52—C57—C56 | 178.14 (15) |
C15—C14—C19—C18 | 1.1 (2) | C53—C52—C57—C56 | −1.2 (2) |
O2—C20—C21—C22 | −15.5 (3) | O4—C58—C59—C60 | 15.8 (3) |
C30—C20—C21—C22 | 165.11 (15) | C68—C58—C59—C60 | −164.81 (15) |
C20—C21—C22—C23 | 177.45 (15) | C58—C59—C60—C61 | −177.62 (15) |
C21—C22—C23—C28 | −10.3 (3) | C59—C60—C61—C66 | 11.6 (3) |
C21—C22—C23—C24 | 169.81 (16) | C59—C60—C61—C62 | −168.95 (16) |
C28—C23—C24—C25 | 0.3 (2) | C66—C61—C62—C63 | −0.6 (2) |
C22—C23—C24—C25 | −179.82 (14) | C60—C61—C62—C63 | 179.96 (14) |
C23—C24—C25—C26 | 0.1 (2) | C61—C62—C63—C64 | 0.8 (2) |
C23—C24—C25—Cl3 | 179.94 (12) | C61—C62—C63—Cl7 | 179.76 (12) |
C24—C25—C26—C27 | −0.7 (2) | C62—C63—C64—C65 | −0.4 (2) |
Cl3—C25—C26—C27 | 179.46 (12) | Cl7—C63—C64—C65 | −179.36 (12) |
C24—C25—C26—Cl4 | −179.92 (12) | C62—C63—C64—Cl8 | 178.92 (12) |
Cl3—C25—C26—Cl4 | 0.3 (2) | Cl7—C63—C64—Cl8 | −0.02 (19) |
C25—C26—C27—C28 | 0.9 (2) | C63—C64—C65—C66 | −0.2 (2) |
Cl4—C26—C27—C28 | −179.85 (12) | Cl8—C64—C65—C66 | −179.51 (12) |
C26—C27—C28—C23 | −0.5 (2) | C64—C65—C66—C61 | 0.4 (2) |
C24—C23—C28—C27 | 0.0 (2) | C62—C61—C66—C65 | 0.0 (2) |
C22—C23—C28—C27 | −179.97 (15) | C60—C61—C66—C65 | 179.44 (15) |
C34—C29—C30—C31 | 0.2 (2) | C72—C67—C68—C69 | −0.5 (2) |
C34—C29—C30—C20 | 179.82 (14) | C72—C67—C68—C58 | 179.99 (14) |
O2—C20—C30—C29 | −25.9 (2) | O4—C58—C68—C67 | 25.6 (2) |
C21—C20—C30—C29 | 153.50 (15) | C59—C58—C68—C67 | −153.76 (15) |
O2—C20—C30—C31 | 153.74 (16) | O4—C58—C68—C69 | −153.83 (16) |
C21—C20—C30—C31 | −26.9 (2) | C59—C58—C68—C69 | 26.8 (2) |
C29—C30—C31—C32 | 2.0 (2) | C67—C68—C69—C70 | −1.9 (2) |
C20—C30—C31—C32 | −177.58 (15) | C58—C68—C69—C70 | 177.53 (15) |
C30—C31—C32—C33 | −2.7 (2) | C68—C69—C70—C71 | 2.6 (2) |
C31—C32—C33—C38 | −178.73 (15) | C69—C70—C71—C72 | −0.9 (2) |
C31—C32—C33—C34 | 1.2 (2) | C69—C70—C71—C76 | 178.78 (15) |
C30—C29—C34—C35 | 177.97 (15) | C68—C67—C72—C71 | 2.3 (2) |
C30—C29—C34—C33 | −1.7 (2) | C68—C67—C72—C73 | −178.02 (15) |
C38—C33—C34—C29 | −179.09 (14) | C70—C71—C72—C67 | −1.6 (2) |
C32—C33—C34—C29 | 1.0 (2) | C76—C71—C72—C67 | 178.80 (14) |
C38—C33—C34—C35 | 1.3 (2) | C70—C71—C72—C73 | 178.71 (14) |
C32—C33—C34—C35 | −178.64 (14) | C76—C71—C72—C73 | −0.9 (2) |
C29—C34—C35—C36 | 179.91 (15) | C67—C72—C73—C74 | −179.76 (15) |
C33—C34—C35—C36 | −0.4 (2) | C71—C72—C73—C74 | 0.0 (2) |
C34—C35—C36—C37 | −0.3 (3) | C72—C73—C74—C75 | 0.6 (3) |
C35—C36—C37—C38 | 0.3 (3) | C73—C74—C75—C76 | −0.1 (3) |
C36—C37—C38—C33 | 0.5 (3) | C74—C75—C76—C71 | −0.9 (3) |
C32—C33—C38—C37 | 178.59 (16) | C70—C71—C76—C75 | −178.21 (15) |
C34—C33—C38—C37 | −1.3 (2) | C72—C71—C76—C75 | 1.4 (2) |
Experimental details
Crystal data | |
Chemical formula | C19H12Cl2O |
Mr | 327.19 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 113 |
a, b, c (Å) | 7.5273 (10), 11.5212 (14), 33.301 (4) |
α, β, γ (°) | 92.338 (7), 96.469 (7), 90.125 (6) |
V (Å3) | 2867.1 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.45 |
Crystal size (mm) | 0.36 × 0.34 × 0.28 |
Data collection | |
Diffractometer | Rigaku Saturn CCD area-detector diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
Tmin, Tmax | 0.855, 0.884 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26590, 13067, 10135 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.659 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.106, 1.07 |
No. of reflections | 13067 |
No. of parameters | 793 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.44 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2004).
Acknowledgements
The authors thank Dr Haibin Song of Nankai University for helpful discussions and the Science Foundation of Guangxi University for financial support.
References
Lu, Z.-K., Huang, P.-M. & Yu, J.-F. (2006). Acta Cryst. E62, o5753–o5754. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound, (I), (Fig. 1) was prepared and structurally characterized as a part of our ongoing studies of pyrazoline derivatives (Lu et al., 2006).