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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2299.
Published online 2009 August 29. doi:  10.1107/S1600536809034084
PMCID: PMC2969996

3-(3,4-Dichloro­phen­yl)-1-(2-naphth­yl)prop-2-en-1-one

Abstract

The asymmetric unit of the title compound, C19H12Cl2O, 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.

Related literature

For a related structure, see Lu et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2299-scheme1.jpg

Experimental

Crystal data

  • C19H12Cl2O
  • M r = 327.19
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2299-efi1.jpg
  • a = 7.5273 (10) Å
  • b = 11.5212 (14) Å
  • c = 33.301 (4) Å
  • α = 92.338 (7)°
  • β = 96.469 (7)°
  • γ = 90.125 (6)°
  • V = 2867.1 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.45 mm−1
  • T = 113 K
  • 0.36 × 0.34 × 0.28 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.855, T max = 0.884
  • 26590 measured reflections
  • 13067 independent reflections
  • 10135 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.106
  • S = 1.07
  • 13067 reflections
  • 793 parameters
  • H-atom parameters constrained
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034084/cv2599sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034084/cv2599Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Dr Haibin Song of Nankai University for helpful discussions and the Science Foundation of Guangxi University for financial support.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

All H atoms were placed geometrically (C—H = 0.95 Å), and refined as riding with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
Four independent molecules of (I), shown with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

Crystal data

C19H12Cl2OZ = 8
Mr = 327.19F(000) = 1344
Triclinic, P1Dx = 1.516 Mg m3
Hall symbol: -P 1Melting point: 426-427 K K
a = 7.5273 (10) ÅMo Kα radiation, λ = 0.71070 Å
b = 11.5212 (14) ÅCell parameters from 4591 reflections
c = 33.301 (4) Åθ = 1.2–27.2°
α = 92.338 (7)°µ = 0.45 mm1
β = 96.469 (7)°T = 113 K
γ = 90.125 (6)°Block, yellow
V = 2867.1 (6) Å30.36 × 0.34 × 0.28 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer13067 independent reflections
Radiation source: Rotating anode10135 reflections with I > 2σ(I)
confocalRint = 0.023
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.9°
ω and [var phi] scansh = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −15→14
Tmin = 0.855, Tmax = 0.884l = −43→43
26590 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0577P)2 + 0.5613P] where P = (Fo2 + 2Fc2)/3
13067 reflections(Δ/σ)max = 0.001
793 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = −0.44 e Å3

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 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)

xyzUiso*/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)
Cl30.48364 (6)−0.02522 (3)−0.207594 (11)0.02037 (9)
Cl40.32062 (6)0.22617 (3)−0.204037 (11)0.02038 (9)
Cl50.80421 (6)0.47713 (3)0.292686 (11)0.02060 (9)
Cl60.97202 (6)0.22757 (4)0.295246 (12)0.02159 (10)
Cl70.29865 (6)−0.02818 (3)0.291430 (11)0.02085 (9)
Cl80.47357 (6)0.22092 (3)0.293851 (12)0.02095 (9)
O10.27954 (17)0.60599 (10)0.01527 (3)0.0239 (3)
O20.78508 (17)−0.10351 (10)0.01670 (3)0.0233 (3)
O30.73173 (17)0.60659 (10)0.51678 (3)0.0235 (3)
O40.23484 (17)−0.10235 (10)0.51615 (3)0.0234 (3)
C10.2845 (2)0.50007 (14)0.01544 (5)0.0163 (3)
C20.2051 (2)0.42617 (14)−0.01949 (5)0.0189 (3)
H20.18290.3461−0.01610.023*
C30.1646 (2)0.47136 (14)−0.05569 (5)0.0165 (3)
H30.19380.5509−0.05800.020*
C40.0788 (2)0.40906 (13)−0.09209 (4)0.0152 (3)
C50.0749 (2)0.46242 (14)−0.12922 (5)0.0159 (3)
H50.12670.5374−0.13030.019*
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)
H8−0.13280.1694−0.12530.020*
C90.0016 (2)0.29893 (13)−0.09119 (5)0.0165 (3)
H90.00450.2616−0.06620.020*
C100.3765 (2)0.49862 (13)0.08884 (5)0.0147 (3)
H100.32810.57450.09070.018*
C110.3692 (2)0.44034 (13)0.05170 (4)0.0153 (3)
C120.4422 (2)0.32751 (14)0.04866 (5)0.0181 (3)
H120.43370.28650.02320.022*
C130.5251 (2)0.27731 (14)0.08231 (5)0.0177 (3)
H130.57810.20300.07970.021*
C140.5329 (2)0.33478 (13)0.12094 (5)0.0150 (3)
C150.4553 (2)0.44688 (13)0.12426 (5)0.0148 (3)
C160.4588 (2)0.50344 (14)0.16303 (5)0.0174 (3)
H160.40640.57790.16560.021*
C170.5371 (2)0.45125 (15)0.19667 (5)0.0204 (3)
H170.53880.48980.22250.024*
C180.6154 (2)0.34067 (15)0.19333 (5)0.0214 (4)
H180.66940.30540.21690.026*
C190.6144 (2)0.28379 (14)0.15648 (5)0.0187 (3)
H190.66850.20960.15460.022*
C200.7887 (2)0.00248 (14)0.01717 (5)0.0171 (3)
C210.7086 (2)0.06819 (14)−0.01763 (5)0.0189 (3)
H210.68680.1490−0.01420.023*
C220.6668 (2)0.01464 (14)−0.05379 (5)0.0165 (3)
H220.6953−0.0654−0.05620.020*
C230.5808 (2)0.06863 (13)−0.09011 (4)0.0149 (3)
C240.5721 (2)0.00596 (13)−0.12721 (5)0.0151 (3)
H240.6211−0.0699−0.12840.018*
C250.4922 (2)0.05398 (13)−0.16234 (4)0.0153 (3)
C260.4207 (2)0.16467 (13)−0.16086 (4)0.0154 (3)
C270.4271 (2)0.22752 (14)−0.12403 (5)0.0167 (3)
H270.37650.3029−0.12300.020*
C280.5071 (2)0.18000 (14)−0.08905 (5)0.0167 (3)
H280.51200.2234−0.06410.020*
C290.8808 (2)0.02162 (13)0.09061 (5)0.0149 (3)
H290.8327−0.05400.09250.018*
C300.8731 (2)0.07115 (13)0.05331 (4)0.0154 (3)
C310.9453 (2)0.18380 (14)0.05041 (5)0.0180 (3)
H310.93650.21880.02490.022*
C321.0276 (2)0.24257 (14)0.08396 (5)0.0172 (3)
H321.07990.31660.08140.021*
C331.0355 (2)0.19405 (13)0.12265 (5)0.0155 (3)
C340.9595 (2)0.08219 (13)0.12592 (4)0.0149 (3)
C350.9641 (2)0.03472 (14)0.16475 (5)0.0174 (3)
H350.9130−0.03970.16740.021*
C361.0415 (2)0.09555 (15)0.19838 (5)0.0215 (3)
H361.04330.06320.22420.026*
C371.1188 (2)0.20578 (15)0.19500 (5)0.0221 (4)
H371.17270.24700.21860.027*
C381.1168 (2)0.25401 (14)0.15806 (5)0.0190 (3)
H381.17020.32810.15610.023*
C390.7281 (2)0.50044 (14)0.51735 (5)0.0170 (3)
C400.7726 (2)0.42625 (14)0.48243 (5)0.0189 (3)
H400.79650.34610.48580.023*
C410.7792 (2)0.47129 (14)0.44642 (5)0.0164 (3)
H410.74980.55110.44410.020*
C420.8279 (2)0.40890 (13)0.40996 (4)0.0147 (3)
C430.7975 (2)0.46376 (13)0.37293 (5)0.0154 (3)
H430.74720.53930.37200.019*
C440.8410 (2)0.40780 (14)0.33775 (4)0.0154 (3)
C450.9157 (2)0.29754 (14)0.33880 (5)0.0157 (3)
C460.9474 (2)0.24305 (14)0.37545 (5)0.0168 (3)
H460.99950.16800.37630.020*
C470.9029 (2)0.29816 (14)0.41062 (5)0.0168 (3)
H470.92380.26020.43550.020*
C480.7104 (2)0.49980 (13)0.59074 (5)0.0149 (3)
H480.76080.57580.59240.018*
C490.6802 (2)0.44107 (13)0.55364 (4)0.0153 (3)
C500.6039 (2)0.32813 (14)0.55080 (5)0.0175 (3)
H500.58600.28690.52540.021*
C510.5557 (2)0.27817 (14)0.58458 (5)0.0177 (3)
H510.50060.20360.58220.021*
C520.5868 (2)0.33593 (13)0.62308 (5)0.0155 (3)
C530.6675 (2)0.44834 (13)0.62628 (5)0.0146 (3)
C540.7031 (2)0.50529 (14)0.66494 (5)0.0183 (3)
H540.75710.58020.66740.022*
C550.6602 (2)0.45286 (15)0.69874 (5)0.0213 (3)
H550.68560.49140.72450.026*
C560.5787 (2)0.34214 (15)0.69557 (5)0.0227 (4)
H560.54890.30680.71920.027*
C570.5420 (2)0.28511 (14)0.65881 (5)0.0192 (3)
H570.48610.21080.65710.023*
C580.2305 (2)0.00346 (14)0.51642 (5)0.0172 (3)
C590.2745 (2)0.06893 (14)0.48147 (5)0.0188 (3)
H590.29940.14980.48480.023*
C600.2794 (2)0.01502 (14)0.44534 (5)0.0168 (3)
H600.2490−0.06530.44310.020*
C610.3273 (2)0.06839 (13)0.40872 (4)0.0154 (3)
C620.2955 (2)0.00500 (14)0.37185 (5)0.0158 (3)
H620.2441−0.07060.37110.019*
C630.3385 (2)0.05196 (14)0.33638 (4)0.0158 (3)
C640.4154 (2)0.16158 (14)0.33743 (4)0.0158 (3)
C650.4487 (2)0.22523 (14)0.37399 (5)0.0169 (3)
H650.50180.30030.37470.020*
C660.4045 (2)0.17903 (13)0.40931 (5)0.0166 (3)
H660.42680.22290.43420.020*
C670.2121 (2)0.02260 (13)0.58983 (5)0.0149 (3)
H670.2623−0.05280.59170.018*
C680.1818 (2)0.07219 (13)0.55265 (4)0.0155 (3)
C690.1058 (2)0.18394 (14)0.54959 (5)0.0177 (3)
H690.08850.21870.52410.021*
C700.0567 (2)0.24240 (14)0.58322 (5)0.0172 (3)
H700.00120.31610.58060.021*
C710.0880 (2)0.19411 (13)0.62188 (5)0.0154 (3)
C720.1689 (2)0.08319 (13)0.62524 (4)0.0142 (3)
C730.2038 (2)0.03555 (14)0.66403 (5)0.0176 (3)
H730.2579−0.03860.66660.021*
C740.1598 (2)0.09629 (15)0.69779 (5)0.0208 (3)
H740.18460.06420.72360.025*
C750.0781 (2)0.20611 (15)0.69434 (5)0.0212 (3)
H750.04810.24730.71790.025*
C760.0416 (2)0.25385 (14)0.65738 (5)0.0185 (3)
H76−0.01510.32730.65540.022*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0263 (2)0.0234 (2)0.01441 (18)−0.00252 (17)0.00050 (15)0.00574 (14)
Cl20.0233 (2)0.0231 (2)0.01752 (18)−0.00437 (16)−0.00162 (15)−0.00247 (14)
Cl30.0270 (2)0.0200 (2)0.01394 (17)0.00279 (16)0.00222 (15)−0.00196 (14)
Cl40.0227 (2)0.0206 (2)0.01712 (18)0.00368 (16)−0.00198 (15)0.00331 (14)
Cl50.0267 (2)0.0216 (2)0.01365 (17)0.00192 (16)0.00179 (15)0.00411 (14)
Cl60.0249 (2)0.0224 (2)0.01806 (18)0.00308 (16)0.00624 (15)−0.00309 (14)
Cl70.0281 (2)0.0203 (2)0.01389 (17)−0.00261 (16)0.00228 (15)−0.00151 (14)
Cl80.0238 (2)0.0222 (2)0.01798 (18)−0.00305 (16)0.00538 (15)0.00522 (14)
O10.0347 (7)0.0173 (6)0.0191 (6)−0.0015 (5)−0.0002 (5)0.0021 (4)
O20.0332 (7)0.0174 (6)0.0184 (6)0.0001 (5)−0.0009 (5)0.0001 (4)
O30.0353 (7)0.0173 (6)0.0183 (6)0.0016 (5)0.0048 (5)0.0015 (4)
O40.0342 (7)0.0177 (6)0.0183 (6)−0.0009 (5)0.0041 (5)0.0002 (4)
C10.0172 (8)0.0176 (8)0.0142 (7)−0.0026 (6)0.0023 (6)0.0018 (6)
C20.0214 (9)0.0175 (8)0.0176 (8)−0.0031 (7)0.0007 (6)0.0010 (6)
C30.0161 (8)0.0168 (8)0.0165 (7)−0.0007 (6)0.0013 (6)0.0000 (6)
C40.0131 (8)0.0165 (8)0.0160 (7)0.0014 (6)0.0017 (6)0.0011 (6)
C50.0140 (8)0.0157 (7)0.0180 (7)−0.0008 (6)0.0018 (6)0.0015 (6)
C60.0146 (8)0.0180 (8)0.0136 (7)0.0017 (6)0.0022 (6)0.0036 (6)
C70.0137 (8)0.0176 (8)0.0151 (7)0.0013 (6)0.0008 (6)−0.0015 (6)
C80.0170 (8)0.0142 (7)0.0198 (7)−0.0015 (6)0.0041 (6)0.0017 (6)
C90.0181 (8)0.0167 (8)0.0152 (7)0.0005 (6)0.0030 (6)0.0030 (6)
C100.0132 (8)0.0133 (7)0.0174 (7)−0.0008 (6)0.0014 (6)0.0005 (6)
C110.0155 (8)0.0164 (8)0.0143 (7)−0.0026 (6)0.0018 (6)0.0027 (6)
C120.0189 (9)0.0188 (8)0.0167 (7)−0.0021 (7)0.0042 (6)−0.0029 (6)
C130.0175 (8)0.0151 (8)0.0211 (8)0.0008 (6)0.0050 (6)−0.0002 (6)
C140.0110 (8)0.0150 (7)0.0194 (7)−0.0019 (6)0.0029 (6)0.0011 (6)
C150.0125 (8)0.0159 (7)0.0160 (7)−0.0015 (6)0.0017 (6)0.0015 (6)
C160.0161 (8)0.0184 (8)0.0174 (7)−0.0002 (6)0.0016 (6)−0.0020 (6)
C170.0201 (9)0.0249 (9)0.0159 (7)−0.0007 (7)0.0006 (6)−0.0002 (6)
C180.0189 (9)0.0251 (9)0.0196 (8)−0.0016 (7)−0.0025 (6)0.0061 (6)
C190.0162 (8)0.0167 (8)0.0234 (8)0.0006 (6)0.0015 (6)0.0042 (6)
C200.0173 (8)0.0193 (8)0.0147 (7)0.0020 (6)0.0021 (6)0.0014 (6)
C210.0214 (9)0.0174 (8)0.0177 (8)0.0024 (7)0.0008 (6)0.0014 (6)
C220.0157 (8)0.0165 (8)0.0175 (7)−0.0002 (6)0.0015 (6)0.0030 (6)
C230.0136 (8)0.0162 (7)0.0150 (7)−0.0014 (6)0.0013 (6)0.0018 (6)
C240.0145 (8)0.0145 (7)0.0164 (7)−0.0005 (6)0.0022 (6)0.0011 (6)
C250.0148 (8)0.0171 (8)0.0142 (7)−0.0027 (6)0.0030 (6)−0.0013 (6)
C260.0131 (8)0.0175 (8)0.0155 (7)−0.0007 (6)0.0003 (6)0.0030 (6)
C270.0152 (8)0.0144 (7)0.0207 (8)0.0012 (6)0.0028 (6)0.0002 (6)
C280.0175 (8)0.0171 (8)0.0155 (7)−0.0003 (6)0.0022 (6)−0.0012 (6)
C290.0137 (8)0.0139 (7)0.0174 (7)0.0007 (6)0.0022 (6)0.0013 (6)
C300.0142 (8)0.0166 (8)0.0154 (7)0.0022 (6)0.0020 (6)0.0006 (6)
C310.0204 (9)0.0193 (8)0.0152 (7)0.0017 (7)0.0046 (6)0.0046 (6)
C320.0167 (8)0.0155 (8)0.0205 (8)−0.0009 (6)0.0061 (6)0.0021 (6)
C330.0127 (8)0.0161 (7)0.0178 (7)0.0011 (6)0.0026 (6)0.0013 (6)
C340.0132 (8)0.0162 (7)0.0156 (7)0.0021 (6)0.0023 (6)0.0009 (6)
C350.0157 (8)0.0182 (8)0.0186 (8)0.0020 (6)0.0021 (6)0.0028 (6)
C360.0236 (9)0.0249 (9)0.0158 (7)0.0036 (7)0.0012 (6)0.0018 (6)
C370.0209 (9)0.0256 (9)0.0187 (8)0.0019 (7)−0.0013 (6)−0.0034 (6)
C380.0163 (8)0.0183 (8)0.0220 (8)−0.0007 (6)0.0014 (6)−0.0021 (6)
C390.0186 (8)0.0180 (8)0.0142 (7)0.0018 (6)0.0000 (6)0.0017 (6)
C400.0210 (9)0.0182 (8)0.0179 (8)0.0035 (7)0.0033 (6)0.0015 (6)
C410.0156 (8)0.0165 (8)0.0169 (7)0.0001 (6)0.0020 (6)−0.0001 (6)
C420.0140 (8)0.0156 (7)0.0144 (7)−0.0027 (6)0.0014 (6)0.0008 (6)
C430.0140 (8)0.0152 (7)0.0173 (7)−0.0003 (6)0.0018 (6)0.0022 (6)
C440.0144 (8)0.0178 (8)0.0140 (7)−0.0015 (6)0.0008 (6)0.0038 (6)
C450.0141 (8)0.0175 (8)0.0155 (7)−0.0010 (6)0.0031 (6)−0.0024 (6)
C460.0155 (8)0.0147 (7)0.0200 (8)0.0004 (6)0.0006 (6)0.0012 (6)
C470.0180 (8)0.0172 (8)0.0150 (7)−0.0006 (6)0.0000 (6)0.0032 (6)
C480.0144 (8)0.0135 (7)0.0167 (7)0.0007 (6)0.0008 (6)0.0014 (6)
C490.0136 (8)0.0173 (8)0.0151 (7)0.0024 (6)0.0010 (6)0.0019 (6)
C500.0175 (8)0.0175 (8)0.0166 (7)0.0021 (6)−0.0013 (6)−0.0023 (6)
C510.0142 (8)0.0152 (8)0.0230 (8)−0.0015 (6)−0.0008 (6)0.0008 (6)
C520.0117 (8)0.0163 (8)0.0185 (7)0.0019 (6)0.0008 (6)0.0028 (6)
C530.0107 (8)0.0172 (8)0.0161 (7)0.0014 (6)0.0013 (6)0.0014 (6)
C540.0165 (8)0.0198 (8)0.0182 (8)0.0005 (6)0.0006 (6)0.0002 (6)
C550.0203 (9)0.0295 (9)0.0140 (7)0.0033 (7)0.0015 (6)−0.0007 (6)
C560.0220 (9)0.0278 (9)0.0195 (8)0.0033 (7)0.0050 (7)0.0087 (7)
C570.0158 (8)0.0185 (8)0.0241 (8)0.0009 (6)0.0032 (6)0.0069 (6)
C580.0179 (8)0.0193 (8)0.0139 (7)−0.0020 (6)−0.0005 (6)0.0010 (6)
C590.0212 (9)0.0182 (8)0.0171 (7)−0.0031 (7)0.0024 (6)0.0017 (6)
C600.0162 (8)0.0174 (8)0.0170 (7)−0.0002 (6)0.0014 (6)0.0024 (6)
C610.0130 (8)0.0172 (8)0.0160 (7)0.0014 (6)0.0016 (6)0.0022 (6)
C620.0140 (8)0.0152 (7)0.0182 (7)−0.0006 (6)0.0012 (6)0.0016 (6)
C630.0146 (8)0.0183 (8)0.0142 (7)0.0019 (6)0.0010 (6)−0.0011 (6)
C640.0141 (8)0.0188 (8)0.0151 (7)0.0013 (6)0.0031 (6)0.0054 (6)
C650.0159 (8)0.0145 (7)0.0200 (8)−0.0015 (6)0.0007 (6)0.0018 (6)
C660.0175 (8)0.0164 (8)0.0153 (7)0.0003 (6)−0.0001 (6)−0.0006 (6)
C670.0141 (8)0.0139 (7)0.0167 (7)−0.0012 (6)0.0006 (6)0.0017 (6)
C680.0154 (8)0.0165 (8)0.0146 (7)−0.0034 (6)0.0011 (6)0.0008 (6)
C690.0182 (8)0.0185 (8)0.0159 (7)−0.0021 (6)−0.0016 (6)0.0042 (6)
C700.0152 (8)0.0152 (8)0.0208 (8)0.0016 (6)−0.0006 (6)0.0029 (6)
C710.0115 (8)0.0165 (8)0.0182 (7)−0.0020 (6)0.0005 (6)0.0018 (6)
C720.0109 (8)0.0160 (7)0.0157 (7)−0.0022 (6)0.0007 (6)0.0021 (6)
C730.0170 (8)0.0183 (8)0.0173 (7)−0.0001 (6)0.0007 (6)0.0030 (6)
C740.0240 (9)0.0232 (8)0.0150 (7)−0.0023 (7)0.0012 (6)0.0025 (6)
C750.0207 (9)0.0238 (9)0.0194 (8)−0.0020 (7)0.0052 (6)−0.0036 (6)
C760.0161 (8)0.0165 (8)0.0226 (8)0.0003 (6)0.0024 (6)−0.0013 (6)

Geometric parameters (Å, °)

Cl1—C61.7246 (15)C35—H350.9500
Cl2—C71.7275 (16)C36—C371.409 (2)
Cl3—C251.7244 (15)C36—H360.9500
Cl4—C261.7258 (15)C37—C381.369 (2)
Cl5—C441.7239 (15)C37—H370.9500
Cl6—C451.7255 (16)C38—H380.9500
Cl7—C631.7229 (16)C39—C401.484 (2)
Cl8—C641.7286 (15)C39—C491.491 (2)
O1—C11.2212 (19)C40—C411.332 (2)
O2—C201.2209 (19)C40—H400.9500
O3—C391.2241 (19)C41—C421.468 (2)
O4—C581.2193 (19)C41—H410.9500
C1—C21.482 (2)C42—C471.396 (2)
C1—C111.495 (2)C42—C431.405 (2)
C2—C31.337 (2)C43—C441.386 (2)
C2—H20.9500C43—H430.9500
C3—C41.467 (2)C44—C451.390 (2)
C3—H30.9500C45—C461.392 (2)
C4—C91.397 (2)C46—C471.384 (2)
C4—C51.400 (2)C46—H460.9500
C5—C61.387 (2)C47—H470.9500
C5—H50.9500C48—C491.380 (2)
C6—C71.389 (2)C48—C531.414 (2)
C7—C81.391 (2)C48—H480.9500
C8—C91.384 (2)C49—C501.417 (2)
C8—H80.9500C50—C511.368 (2)
C9—H90.9500C50—H500.9500
C10—C111.379 (2)C51—C521.415 (2)
C10—C151.414 (2)C51—H510.9500
C10—H100.9500C52—C571.421 (2)
C11—C121.417 (2)C52—C531.424 (2)
C12—C131.370 (2)C53—C541.419 (2)
C12—H120.9500C54—C551.369 (2)
C13—C141.418 (2)C54—H540.9500
C13—H130.9500C55—C561.409 (2)
C14—C191.420 (2)C55—H550.9500
C14—C151.424 (2)C56—C571.365 (2)
C15—C161.420 (2)C56—H560.9500
C16—C171.368 (2)C57—H570.9500
C16—H160.9500C58—C591.480 (2)
C17—C181.411 (2)C58—C681.497 (2)
C17—H170.9500C59—C601.336 (2)
C18—C191.366 (2)C59—H590.9500
C18—H180.9500C60—C611.468 (2)
C19—H190.9500C60—H600.9500
C20—C211.482 (2)C61—C661.398 (2)
C20—C301.492 (2)C61—C621.399 (2)
C21—C221.335 (2)C62—C631.389 (2)
C21—H210.9500C62—H620.9500
C22—C231.468 (2)C63—C641.386 (2)
C22—H220.9500C64—C651.393 (2)
C23—C281.400 (2)C65—C661.384 (2)
C23—C241.400 (2)C65—H650.9500
C24—C251.390 (2)C66—H660.9500
C24—H240.9500C67—C681.381 (2)
C25—C261.386 (2)C67—C721.415 (2)
C26—C271.395 (2)C67—H670.9500
C27—C281.384 (2)C68—C691.413 (2)
C27—H270.9500C69—C701.370 (2)
C28—H280.9500C69—H690.9500
C29—C301.383 (2)C70—C711.419 (2)
C29—C341.413 (2)C70—H700.9500
C29—H290.9500C71—C721.420 (2)
C30—C311.417 (2)C71—C761.421 (2)
C31—C321.368 (2)C72—C731.422 (2)
C31—H310.9500C73—C741.373 (2)
C32—C331.420 (2)C73—H730.9500
C32—H320.9500C74—C751.411 (2)
C33—C381.418 (2)C74—H740.9500
C33—C341.422 (2)C75—C761.368 (2)
C34—C351.421 (2)C75—H750.9500
C35—C361.369 (2)C76—H760.9500
O1—C1—C2121.90 (14)O3—C39—C40121.64 (14)
O1—C1—C11120.52 (14)O3—C39—C49120.78 (14)
C2—C1—C11117.57 (13)C40—C39—C49117.58 (13)
C3—C2—C1120.43 (15)C41—C40—C39120.45 (15)
C3—C2—H2119.8C41—C40—H40119.8
C1—C2—H2119.8C39—C40—H40119.8
C2—C3—C4125.77 (15)C40—C41—C42125.94 (15)
C2—C3—H3117.1C40—C41—H41117.0
C4—C3—H3117.1C42—C41—H41117.0
C9—C4—C5118.88 (14)C47—C42—C43118.94 (14)
C9—C4—C3122.70 (14)C47—C42—C41122.89 (13)
C5—C4—C3118.42 (14)C43—C42—C41118.16 (14)
C6—C5—C4120.36 (14)C44—C43—C42120.05 (14)
C6—C5—H5119.8C44—C43—H43120.0
C4—C5—H5119.8C42—C43—H43120.0
C5—C6—C7120.10 (14)C43—C44—C45120.46 (13)
C5—C6—Cl1119.34 (12)C43—C44—Cl5119.29 (12)
C7—C6—Cl1120.56 (12)C45—C44—Cl5120.24 (12)
C6—C7—C8120.04 (14)C44—C45—C46119.78 (14)
C6—C7—Cl2120.74 (12)C44—C45—Cl6120.85 (12)
C8—C7—Cl2119.21 (12)C46—C45—Cl6119.37 (12)
C9—C8—C7119.89 (15)C47—C46—C45119.99 (15)
C9—C8—H8120.1C47—C46—H46120.0
C7—C8—H8120.1C45—C46—H46120.0
C8—C9—C4120.72 (14)C46—C47—C42120.77 (14)
C8—C9—H9119.6C46—C47—H47119.6
C4—C9—H9119.6C42—C47—H47119.6
C11—C10—C15120.81 (14)C49—C48—C53120.84 (14)
C11—C10—H10119.6C49—C48—H48119.6
C15—C10—H10119.6C53—C48—H48119.6
C10—C11—C12119.97 (14)C48—C49—C50119.95 (14)
C10—C11—C1118.11 (14)C48—C49—C39118.11 (14)
C12—C11—C1121.91 (14)C50—C49—C39121.93 (14)
C13—C12—C11120.29 (14)C51—C50—C49120.23 (14)
C13—C12—H12119.9C51—C50—H50119.9
C11—C12—H12119.9C49—C50—H50119.9
C12—C13—C14120.88 (15)C50—C51—C52121.00 (15)
C12—C13—H13119.6C50—C51—H51119.5
C14—C13—H13119.6C52—C51—H51119.5
C13—C14—C19122.14 (14)C51—C52—C57122.25 (15)
C13—C14—C15118.93 (14)C51—C52—C53119.02 (14)
C19—C14—C15118.93 (14)C57—C52—C53118.72 (14)
C10—C15—C16121.85 (14)C48—C53—C54121.89 (14)
C10—C15—C14119.05 (14)C48—C53—C52118.90 (14)
C16—C15—C14119.10 (14)C54—C53—C52119.21 (14)
C17—C16—C15120.36 (15)C55—C54—C53120.37 (15)
C17—C16—H16119.8C55—C54—H54119.8
C15—C16—H16119.8C53—C54—H54119.8
C16—C17—C18120.52 (15)C54—C55—C56120.47 (15)
C16—C17—H17119.7C54—C55—H55119.8
C18—C17—H17119.7C56—C55—H55119.8
C19—C18—C17120.64 (14)C57—C56—C55120.64 (15)
C19—C18—H18119.7C57—C56—H56119.7
C17—C18—H18119.7C55—C56—H56119.7
C18—C19—C14120.44 (15)C56—C57—C52120.57 (15)
C18—C19—H19119.8C56—C57—H57119.7
C14—C19—H19119.8C52—C57—H57119.7
O2—C20—C21121.80 (14)O4—C58—C59121.78 (15)
O2—C20—C30120.90 (14)O4—C58—C68120.78 (14)
C21—C20—C30117.30 (14)C59—C58—C68117.44 (14)
C22—C21—C20120.46 (15)C60—C59—C58120.44 (15)
C22—C21—H21119.8C60—C59—H59119.8
C20—C21—H21119.8C58—C59—H59119.8
C21—C22—C23125.74 (15)C59—C60—C61126.00 (15)
C21—C22—H22117.1C59—C60—H60117.0
C23—C22—H22117.1C61—C60—H60117.0
C28—C23—C24118.84 (13)C66—C61—C62118.95 (14)
C28—C23—C22122.59 (14)C66—C61—C60122.73 (14)
C24—C23—C22118.57 (14)C62—C61—C60118.31 (14)
C25—C24—C23120.42 (14)C63—C62—C61120.37 (14)
C25—C24—H24119.8C63—C62—H62119.8
C23—C24—H24119.8C61—C62—H62119.8
C26—C25—C24120.08 (14)C64—C63—C62120.05 (14)
C26—C25—Cl3120.54 (12)C64—C63—Cl7120.53 (12)
C24—C25—Cl3119.38 (12)C62—C63—Cl7119.41 (12)
C25—C26—C27120.03 (14)C63—C64—C65120.10 (14)
C25—C26—Cl4120.98 (12)C63—C64—Cl8120.92 (12)
C27—C26—Cl4118.99 (12)C65—C64—Cl8118.98 (12)
C28—C27—C26119.96 (14)C66—C65—C64119.95 (15)
C28—C27—H27120.0C66—C65—H65120.0
C26—C27—H27120.0C64—C65—H65120.0
C27—C28—C23120.66 (14)C65—C66—C61120.57 (14)
C27—C28—H28119.7C65—C66—H66119.7
C23—C28—H28119.7C61—C66—H66119.7
C30—C29—C34120.75 (14)C68—C67—C72120.57 (14)
C30—C29—H29119.6C68—C67—H67119.7
C34—C29—H29119.6C72—C67—H67119.7
C29—C30—C31119.72 (14)C67—C68—C69120.09 (14)
C29—C30—C20118.11 (14)C67—C68—C58117.86 (14)
C31—C30—C20122.17 (13)C69—C68—C58122.05 (13)
C32—C31—C30120.61 (14)C70—C69—C68120.37 (14)
C32—C31—H31119.7C70—C69—H69119.8
C30—C31—H31119.7C68—C69—H69119.8
C31—C32—C33120.68 (14)C69—C70—C71120.73 (15)
C31—C32—H32119.7C69—C70—H70119.6
C33—C32—H32119.7C71—C70—H70119.6
C38—C33—C32121.89 (15)C70—C71—C72119.03 (14)
C38—C33—C34119.14 (14)C70—C71—C76121.91 (14)
C32—C33—C34118.96 (14)C72—C71—C76119.06 (14)
C29—C34—C35121.81 (14)C67—C72—C71119.14 (13)
C29—C34—C33119.22 (14)C67—C72—C73121.65 (14)
C35—C34—C33118.97 (14)C71—C72—C73119.21 (14)
C36—C35—C34120.39 (15)C74—C73—C72120.26 (15)
C36—C35—H35119.8C74—C73—H73119.9
C34—C35—H35119.8C72—C73—H73119.9
C35—C36—C37120.54 (15)C73—C74—C75120.41 (15)
C35—C36—H36119.7C73—C74—H74119.8
C37—C36—H36119.7C75—C74—H74119.8
C38—C37—C36120.57 (15)C76—C75—C74120.67 (15)
C38—C37—H37119.7C76—C75—H75119.7
C36—C37—H37119.7C74—C75—H75119.7
C37—C38—C33120.38 (15)C75—C76—C71120.37 (15)
C37—C38—H38119.8C75—C76—H76119.8
C33—C38—H38119.8C71—C76—H76119.8
O1—C1—C2—C316.4 (3)O3—C39—C40—C41−14.9 (3)
C11—C1—C2—C3−164.66 (15)C49—C39—C40—C41165.71 (15)
C1—C2—C3—C4−177.23 (15)C39—C40—C41—C42177.56 (15)
C2—C3—C4—C911.3 (3)C40—C41—C42—C47−11.3 (3)
C2—C3—C4—C5−168.55 (16)C40—C41—C42—C43168.90 (16)
C9—C4—C5—C6−0.1 (2)C47—C42—C43—C440.4 (2)
C3—C4—C5—C6179.73 (14)C41—C42—C43—C44−179.80 (14)
C4—C5—C6—C70.3 (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—C80.2 (2)C43—C44—C45—C46−0.1 (2)
Cl1—C6—C7—C8179.99 (12)Cl5—C44—C45—C46179.02 (12)
C5—C6—C7—Cl2178.97 (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—C470.6 (2)
Cl2—C7—C8—C9−179.68 (12)Cl6—C45—C46—C47179.97 (12)
C7—C8—C9—C41.1 (2)C45—C46—C47—C42−0.6 (2)
C5—C4—C9—C8−0.6 (2)C43—C42—C47—C460.1 (2)
C3—C4—C9—C8179.58 (15)C41—C42—C47—C46−179.70 (15)
C15—C10—C11—C12−0.5 (2)C53—C48—C49—C500.5 (2)
C15—C10—C11—C1−179.89 (14)C53—C48—C49—C39179.83 (14)
O1—C1—C11—C1025.3 (2)O3—C39—C49—C48−25.8 (2)
C2—C1—C11—C10−153.71 (15)C40—C39—C49—C48153.58 (15)
O1—C1—C11—C12−154.15 (16)O3—C39—C49—C50153.49 (16)
C2—C1—C11—C1226.9 (2)C40—C39—C49—C50−27.1 (2)
C10—C11—C12—C13−2.0 (2)C48—C49—C50—C511.7 (2)
C1—C11—C12—C13177.42 (15)C39—C49—C50—C51−177.61 (15)
C11—C12—C13—C142.7 (2)C49—C50—C51—C52−2.3 (2)
C12—C13—C14—C19178.56 (15)C50—C51—C52—C57−178.52 (15)
C12—C13—C14—C15−0.9 (2)C50—C51—C52—C530.8 (2)
C11—C10—C15—C16−177.72 (15)C49—C48—C53—C54177.73 (14)
C11—C10—C15—C142.2 (2)C49—C48—C53—C52−2.0 (2)
C13—C14—C15—C10−1.5 (2)C51—C52—C53—C481.4 (2)
C19—C14—C15—C10179.02 (14)C57—C52—C53—C48−179.30 (14)
C13—C14—C15—C16178.41 (14)C51—C52—C53—C54−178.39 (14)
C19—C14—C15—C16−1.1 (2)C57—C52—C53—C540.9 (2)
C10—C15—C16—C17−179.55 (15)C48—C53—C54—C55−179.85 (15)
C14—C15—C16—C170.6 (2)C52—C53—C54—C55−0.1 (2)
C15—C16—C17—C180.0 (3)C53—C54—C55—C56−0.6 (2)
C16—C17—C18—C190.0 (3)C54—C55—C56—C570.4 (3)
C17—C18—C19—C14−0.6 (3)C55—C56—C57—C520.5 (3)
C13—C14—C19—C18−178.40 (15)C51—C52—C57—C56178.14 (15)
C15—C14—C19—C181.1 (2)C53—C52—C57—C56−1.2 (2)
O2—C20—C21—C22−15.5 (3)O4—C58—C59—C6015.8 (3)
C30—C20—C21—C22165.11 (15)C68—C58—C59—C60−164.81 (15)
C20—C21—C22—C23177.45 (15)C58—C59—C60—C61−177.62 (15)
C21—C22—C23—C28−10.3 (3)C59—C60—C61—C6611.6 (3)
C21—C22—C23—C24169.81 (16)C59—C60—C61—C62−168.95 (16)
C28—C23—C24—C250.3 (2)C66—C61—C62—C63−0.6 (2)
C22—C23—C24—C25−179.82 (14)C60—C61—C62—C63179.96 (14)
C23—C24—C25—C260.1 (2)C61—C62—C63—C640.8 (2)
C23—C24—C25—Cl3179.94 (12)C61—C62—C63—Cl7179.76 (12)
C24—C25—C26—C27−0.7 (2)C62—C63—C64—C65−0.4 (2)
Cl3—C25—C26—C27179.46 (12)Cl7—C63—C64—C65−179.36 (12)
C24—C25—C26—Cl4−179.92 (12)C62—C63—C64—Cl8178.92 (12)
Cl3—C25—C26—Cl40.3 (2)Cl7—C63—C64—Cl8−0.02 (19)
C25—C26—C27—C280.9 (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—C610.4 (2)
C24—C23—C28—C270.0 (2)C62—C61—C66—C650.0 (2)
C22—C23—C28—C27−179.97 (15)C60—C61—C66—C65179.44 (15)
C34—C29—C30—C310.2 (2)C72—C67—C68—C69−0.5 (2)
C34—C29—C30—C20179.82 (14)C72—C67—C68—C58179.99 (14)
O2—C20—C30—C29−25.9 (2)O4—C58—C68—C6725.6 (2)
C21—C20—C30—C29153.50 (15)C59—C58—C68—C67−153.76 (15)
O2—C20—C30—C31153.74 (16)O4—C58—C68—C69−153.83 (16)
C21—C20—C30—C31−26.9 (2)C59—C58—C68—C6926.8 (2)
C29—C30—C31—C322.0 (2)C67—C68—C69—C70−1.9 (2)
C20—C30—C31—C32−177.58 (15)C58—C68—C69—C70177.53 (15)
C30—C31—C32—C33−2.7 (2)C68—C69—C70—C712.6 (2)
C31—C32—C33—C38−178.73 (15)C69—C70—C71—C72−0.9 (2)
C31—C32—C33—C341.2 (2)C69—C70—C71—C76178.78 (15)
C30—C29—C34—C35177.97 (15)C68—C67—C72—C712.3 (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—C291.0 (2)C76—C71—C72—C67178.80 (14)
C38—C33—C34—C351.3 (2)C70—C71—C72—C73178.71 (14)
C32—C33—C34—C35−178.64 (14)C76—C71—C72—C73−0.9 (2)
C29—C34—C35—C36179.91 (15)C67—C72—C73—C74−179.76 (15)
C33—C34—C35—C36−0.4 (2)C71—C72—C73—C740.0 (2)
C34—C35—C36—C37−0.3 (3)C72—C73—C74—C750.6 (3)
C35—C36—C37—C380.3 (3)C73—C74—C75—C76−0.1 (3)
C36—C37—C38—C330.5 (3)C74—C75—C76—C71−0.9 (3)
C32—C33—C38—C37178.59 (16)C70—C71—C76—C75−178.21 (15)
C34—C33—C38—C37−1.3 (2)C72—C71—C76—C751.4 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2599).

References

  • Lu, Z.-K., Huang, P.-M. & Yu, J.-F. (2006). Acta Cryst. E62, o5753–o5754.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2004). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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