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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 7| July 2014| Page o802
https://doi.org/10.1107/S160053681401383X

Ethyl 2,6-bis­­(4-chloro­phen­yl)-1-iso­cyano-4-oxo­cyclo­hexa­ne­carboxyl­ate

Dawei Zhang,a Peng Yang,a Wei Liua and Jing Lib*

aCollege of Agricultural Sciences, Jilin University, Changchun, Jilin Province 130062, People's Republic of China, and bCollege of Life Sciences and Biotechnology, Heilongjiang Bayi Agricultural University, Heilongjiang Province 163319, People's Republic of China
*Correspondence e-mail: lijingroea@gmail.com

(Received 8 May 2014; accepted 13 June 2014; online 21 June 2014)

In the title compound, C22H19Cl2NO3, the central six-membered ring is in a twist-boat conformation. The two aryl groups are in equatorial positions, trans to each other and with a dihedral angle of 77.50 (2)° between them. One of the least hindered –CH2– groups and one of the aryl-substituted C atoms, with its axial H atom, are in the flagpole positions. The eth­oxy­carbonyl group is in an equatorial position and is cis to the second aryl group. In the crystal, molecules are linked via weak C—H⋯O hydrogen bonds, forming chains along [010].

Keywords: crystal structure.

CCDC reference: 1008201

Similar articles

Related literature

For the synthesis, see: Zhang et al. (2010[Zhang, D., Xu, X. & &Liu, Q. (2010). Synlett, 6, 917-920.]); Tan et al. (2009[Tan, J., Xu, X., Zhang, L., Li, Y. & Liu, Q. (2009). Angew. Chem. Int. Ed. 48, 2868-2872.]). For related structures, see: Rowland & Gill (1988[Rowland, A. T. & Gill, B. C. (1988). J. Org. Chem. 53, 434-437.]); Aleman et al. (2009[Aleman, C., Jiménez, A. I., Cativiela, C., Nussinov, R. & Casanovas, J. (2009). J. Org. Chem. 74, 7834-7843.]); Wu et al. (2011[Wu, B., Liu, G., Li, M., Zhang, Y., Zhang, S., Qiu, J., Xu, X., Ji, S. & Wang, X. (2011). Chem. Commun. 47, 3992-3994.]); Li et al. (2011[Li, Y., Xu, X., Tan, J., Xia, C., Zhang, D. & Liu, Q. (2011). J. Am. Chem. Soc. 133, 1775-1777.]). For other [5 + 1] annulation reactions, see: Bi et al. (2005[Bi, X., Dong, D., Liu, Q., Pan, W., Zhao, L. & Li, B. (2005). J. Am. Chem. Soc. 127, 4578-4579.]); Zhao et al. (2006[Zhao, L., Liang, F., Bi, X., Sun, S. & Liu, Q. (2006). J. Org. Chem. 71, 1094-1098.]); Fu et al. (2009[Fu, Z., Wang, M., Dong, Y., Liu, J. & Liu, Q. (2009). J. Org. Chem. 74, 6105-6110.]); Xu et al. (2012[Xu, X., Liu, Y. & Park, C. (2012). Angew. Chem. Int. Ed. 51, 9372-9376.]).

[Scheme 1]

Experimental

Crystal data

  • C22H19Cl2NO3

  • Mr = 416.28

  • Monoclinic, C 2/c

  • a = 21.6980 (17) Å

  • b = 11.0770 (19) Å

  • c = 17.515 (3) Å

  • β = 104.535 (2)°

  • V = 4075.0 (10) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.34 mm−1

  • T = 293 K

  • 0.21 × 0.19 × 0.15 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.932, Tmax = 0.951

  • 9983 measured reflections

  • 3602 independent reflections

  • 2584 reflections with I > 2σ(I)

  • Rint = 0.027
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.117

  • S = 1.01

  • 3602 reflections

  • 253 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C11—H11⋯O1i 0.98 2.57 3.218 (3) 123
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1008201

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S160053681401383X/lr2127sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681401383X/lr2127Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681401383X/lr2127Isup3.cml

checkCIF report


Experimental top

Synthesis and crystallization top

To the mixture of 1,5-bis­(4-chloro­phenyl)­penta-1,4-dien-3-one (303 mg, 1.0 mmol) and ethyl iso­cyano­acetate (0.132 mL, 1.2 mmol) in DMF (5 mL) was added 1,8-di­aza­bicyclo [5.4.0]undec-7-ene (DBU) (0.015 mL, 0.1 mmol) in one portion at room temperature. The reaction mixture was stirred at room temperature, and the reaction mixture was monitored by TLC. After the substrate 1,5-bis­(4-chloro­phenyl)­penta-1,4-dien-3-one was consumed, the resulting mixture was poured into ice-water (30 mL) under stirring. The precipitated solid was collected by filtration, washed with water (3 × 10 mL), and dried under vacuum to afford the crude product, which was purified by flash chromatography (silica gel, petroleum ether : di­ethyl ether = 3:1, V/V) to give ethyl 2,6-bis­(4-chloro­phenyl)-1-iso­cyano-4-oxo­cyclo­hexane­carboxyl­ate (387 mg, 93%). The material was recrystallized from a mixture of petroleum ether and di­ethyl ether to provide a crystalline solid.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.Hydrogen atoms were generated in idealized positions (according to the sp2 or sp3 geometries of their parent carbon), and then refined using a riding model with fixed C—H distances (C—H = 0.95–1.00 Å) and with Uiso(H) = 1.2Ueq(C).

Results and discussion top

[5+1] annulation is a novel strategy for the construction of six-membered cyclic compounds and total synthesis of natural products (Rowland & Gill, 1988; Wu et al., 2011; Li et al., 2011). The regiospecific [5+1] annulation reactions have drawn much attentions and both the five-carbon 1,5-bielectrophiles and the one-atom nucleophiles been explored extensively (Bi et al., 2005; Zhao et al., 2006; Fu et al., 2009; Xu et al., 2012). We have been dealing with functionalized ketene di­thio­acetals for several years and have succeeded in the preparation of six-membered aromatic and heterocyclic compounds based on [5C+1X] annulations (Zhang et al., 2010; Tan et al., 2009). The aromatic cyclic compounds are analogues of phenyl­alanine (Phe) which are potential moieties for the synthesis of peptide analogues with controlled fold in the backbone. The constrained ring systems play important roles in restricting torsional angle χ1 and in peptide receptor recognition processes (Aleman et al., 2009).

The crystal structure of title compound, a phenyl substituted highly constrained cyclo­hexane analogue of Ph, is reported in this paper. Due to the steric hindrance, the oxo­cyclo­hexane is in a twist-boat conformation (Fig. 1). The ethoxyl carbonyl and the two aryl groups are located in equatorial positions. The dihedral angle between two aromatic rings is 77.495 (20)°. The C7 axial hydrogen and the CH2 bonded to C10 are on the flagpole positions of the boat conformation, which give the least torsional strain. The equatorial ethoxyl carbonyl on C18 and the equatorial aryl group on C11 also lead the formation of a comparable stable boat conformation of this compound.

Related literature top

For the synthesis, see: Zhang et al. (2010); Tan et al. (2009). For related structures, see: Rowland & Gill (1988); Aleman et al. (2009); Wu et al. (2011); Li et al. (2011). For other [5+1] annulation reactions, see: Bi et al. (2005); Zhao et al. (2006); Fu et al. (2009); Xu et al. (2012).

Structure description top

[5+1] annulation is a novel strategy for the construction of six-membered cyclic compounds and total synthesis of natural products (Rowland & Gill, 1988; Wu et al., 2011; Li et al., 2011). The regiospecific [5+1] annulation reactions have drawn much attentions and both the five-carbon 1,5-bielectrophiles and the one-atom nucleophiles been explored extensively (Bi et al., 2005; Zhao et al., 2006; Fu et al., 2009; Xu et al., 2012). We have been dealing with functionalized ketene di­thio­acetals for several years and have succeeded in the preparation of six-membered aromatic and heterocyclic compounds based on [5C+1X] annulations (Zhang et al., 2010; Tan et al., 2009). The aromatic cyclic compounds are analogues of phenyl­alanine (Phe) which are potential moieties for the synthesis of peptide analogues with controlled fold in the backbone. The constrained ring systems play important roles in restricting torsional angle χ1 and in peptide receptor recognition processes (Aleman et al., 2009).

The crystal structure of title compound, a phenyl substituted highly constrained cyclo­hexane analogue of Ph, is reported in this paper. Due to the steric hindrance, the oxo­cyclo­hexane is in a twist-boat conformation (Fig. 1). The ethoxyl carbonyl and the two aryl groups are located in equatorial positions. The dihedral angle between two aromatic rings is 77.495 (20)°. The C7 axial hydrogen and the CH2 bonded to C10 are on the flagpole positions of the boat conformation, which give the least torsional strain. The equatorial ethoxyl carbonyl on C18 and the equatorial aryl group on C11 also lead the formation of a comparable stable boat conformation of this compound.

For the synthesis, see: Zhang et al. (2010); Tan et al. (2009). For related structures, see: Rowland & Gill (1988); Aleman et al. (2009); Wu et al. (2011); Li et al. (2011). For other [5+1] annulation reactions, see: Bi et al. (2005); Zhao et al. (2006); Fu et al. (2009); Xu et al. (2012).

Synthesis and crystallization top

To the mixture of 1,5-bis­(4-chloro­phenyl)­penta-1,4-dien-3-one (303 mg, 1.0 mmol) and ethyl iso­cyano­acetate (0.132 mL, 1.2 mmol) in DMF (5 mL) was added 1,8-di­aza­bicyclo [5.4.0]undec-7-ene (DBU) (0.015 mL, 0.1 mmol) in one portion at room temperature. The reaction mixture was stirred at room temperature, and the reaction mixture was monitored by TLC. After the substrate 1,5-bis­(4-chloro­phenyl)­penta-1,4-dien-3-one was consumed, the resulting mixture was poured into ice-water (30 mL) under stirring. The precipitated solid was collected by filtration, washed with water (3 × 10 mL), and dried under vacuum to afford the crude product, which was purified by flash chromatography (silica gel, petroleum ether : di­ethyl ether = 3:1, V/V) to give ethyl 2,6-bis­(4-chloro­phenyl)-1-iso­cyano-4-oxo­cyclo­hexane­carboxyl­ate (387 mg, 93%). The material was recrystallized from a mixture of petroleum ether and di­ethyl ether to provide a crystalline solid.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1.Hydrogen atoms were generated in idealized positions (according to the sp2 or sp3 geometries of their parent carbon), and then refined using a riding model with fixed C—H distances (C—H = 0.95–1.00 Å) and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level.
Ethyl 2,6-bis(4-chlorophenyl)-1-isocyano-4-oxocyclohexanecarboxylate top
Crystal data top
C22H19Cl2NO3F(000) = 1728
Mr = 416.28Dx = 1.357 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 106 reflections
a = 21.6980 (17) Åθ = 1.3–26.0°
b = 11.0770 (19) ŵ = 0.34 mm−1
c = 17.515 (3) ÅT = 293 K
β = 104.535 (2)°BLOCK, colorless
V = 4075.0 (10) Å30.21 × 0.19 × 0.15 mm
Z = 8
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		3602 independent reflections
Radiation source: fine-focus sealed tube2584 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −25→25
Tmin = 0.932, Tmax = 0.951k = −13→13
9983 measured reflectionsl = −20→9
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0514P)2 + 2.7869P]
where P = (Fo2 + 2Fc2)/3
3602 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.35 e Å−3
Crystal data top
C22H19Cl2NO3V = 4075.0 (10) Å3
Mr = 416.28Z = 8
Monoclinic, C2/cMo Kα radiation
a = 21.6980 (17) ŵ = 0.34 mm−1
b = 11.0770 (19) ÅT = 293 K
c = 17.515 (3) Å0.21 × 0.19 × 0.15 mm
β = 104.535 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		3602 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2584 reflections with I > 2σ(I)
Tmin = 0.932, Tmax = 0.951Rint = 0.027
9983 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.01Δρmax = 0.37 e Å−3
3602 reflectionsΔρmin = −0.35 e Å−3
253 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
xyzUiso*/Ueq
Cl2−0.01505 (3)0.07074 (6)0.62309 (5)0.0780 (2)
Cl10.59500 (4)0.06816 (9)0.99930 (6)0.1128 (4)
O20.30900 (7)0.21848 (13)0.84990 (9)0.0528 (4)
C120.18929 (9)0.19357 (17)0.66846 (12)0.0443 (5)
C180.30971 (9)0.15687 (17)0.72324 (12)0.0435 (5)
N10.30407 (9)0.04712 (16)0.67773 (12)0.0524 (5)
C110.25594 (9)0.24575 (18)0.68262 (12)0.0424 (5)
H110.25780.31290.71960.051*
C40.42949 (9)0.17517 (19)0.79764 (14)0.0492 (5)
O10.28944 (9)0.02289 (15)0.82275 (11)0.0759 (5)
C70.37764 (9)0.21213 (18)0.72628 (13)0.0477 (5)
H70.39010.17670.68110.057*
C190.30148 (9)0.12206 (19)0.80460 (13)0.0475 (5)
C90.33050 (11)0.3749 (2)0.63092 (15)0.0552 (6)
C170.15361 (10)0.2176 (2)0.72194 (14)0.0561 (6)
H170.17190.26080.76760.067*
O30.34259 (9)0.45029 (17)0.58723 (12)0.0832 (6)
C140.09922 (11)0.0868 (2)0.58857 (14)0.0567 (6)
H140.08110.04130.54400.068*
C100.27117 (10)0.2997 (2)0.60953 (13)0.0517 (5)
H10A0.27670.23520.57440.062*
H10B0.23580.34940.58180.062*
C150.06450 (10)0.1152 (2)0.64196 (15)0.0551 (6)
C80.37399 (10)0.34828 (19)0.71039 (14)0.0542 (6)
H8A0.35840.38880.75090.065*
H8B0.41620.37910.71250.065*
C130.16142 (10)0.12688 (19)0.60210 (13)0.0526 (6)
H130.18490.10860.56590.063*
C200.30188 (13)0.2027 (3)0.93036 (14)0.0705 (7)
H20A0.25950.22720.93270.085*
H20B0.30740.11830.94520.085*
C160.09146 (11)0.1789 (2)0.70886 (16)0.0646 (7)
H160.06800.19610.74530.078*
C30.46190 (11)0.2575 (2)0.85150 (16)0.0690 (7)
H30.44960.33810.84590.083*
C50.44867 (12)0.0562 (2)0.80921 (17)0.0694 (7)
H50.4275−0.00250.77440.083*
C10.53022 (11)0.1084 (3)0.92278 (17)0.0717 (7)
C60.49881 (14)0.0224 (3)0.87177 (19)0.0829 (9)
H60.5109−0.05820.87890.099*
C220.30053 (14)−0.0380 (2)0.63980 (18)0.0765 (8)
C20.51188 (12)0.2252 (3)0.91352 (18)0.0793 (8)
H20.53290.28340.94890.095*
C210.34862 (18)0.2745 (3)0.98441 (18)0.1104 (12)
H21A0.34370.26401.03700.166*
H21B0.34280.35810.96980.166*
H21C0.39050.24930.98250.166*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl20.0464 (3)0.0811 (5)0.1010 (6)−0.0096 (3)0.0083 (3)−0.0033 (4)
Cl10.0699 (5)0.1466 (8)0.1075 (7)0.0144 (5)−0.0045 (4)0.0360 (6)
O20.0637 (9)0.0523 (9)0.0461 (9)−0.0020 (7)0.0207 (7)0.0016 (7)
C120.0474 (11)0.0384 (10)0.0454 (12)0.0012 (9)0.0087 (10)0.0009 (9)
C180.0492 (11)0.0345 (10)0.0487 (13)−0.0035 (8)0.0159 (10)−0.0030 (9)
N10.0580 (11)0.0386 (10)0.0609 (12)−0.0003 (8)0.0153 (9)−0.0051 (9)
C110.0472 (11)0.0377 (10)0.0428 (12)−0.0030 (8)0.0122 (9)−0.0017 (9)
C40.0417 (11)0.0520 (12)0.0586 (14)−0.0016 (9)0.0216 (10)0.0030 (11)
O10.1060 (14)0.0511 (10)0.0770 (13)−0.0162 (9)0.0350 (11)0.0125 (9)
C70.0480 (12)0.0463 (12)0.0534 (13)−0.0034 (9)0.0210 (10)−0.0009 (10)
C190.0430 (11)0.0458 (12)0.0543 (14)−0.0024 (9)0.0136 (10)0.0049 (11)
C90.0647 (14)0.0492 (12)0.0582 (15)−0.0031 (11)0.0275 (12)0.0072 (12)
C170.0511 (13)0.0594 (14)0.0583 (15)−0.0059 (10)0.0147 (11)−0.0144 (12)
O30.0888 (13)0.0857 (13)0.0778 (13)−0.0170 (10)0.0257 (11)0.0318 (11)
C140.0580 (14)0.0522 (13)0.0528 (14)−0.0055 (10)0.0009 (11)−0.0060 (11)
C100.0611 (13)0.0484 (12)0.0456 (13)0.0006 (10)0.0133 (11)0.0013 (10)
C150.0456 (12)0.0486 (12)0.0674 (16)−0.0023 (10)0.0076 (11)0.0037 (12)
C80.0538 (12)0.0498 (13)0.0609 (15)−0.0114 (10)0.0179 (11)0.0043 (11)
C130.0548 (13)0.0538 (13)0.0491 (14)−0.0020 (10)0.0130 (11)−0.0039 (11)
C200.0799 (17)0.0865 (19)0.0499 (15)0.0054 (14)0.0254 (14)0.0099 (14)
C160.0535 (13)0.0734 (16)0.0714 (17)−0.0050 (12)0.0240 (13)−0.0131 (14)
C30.0583 (14)0.0608 (15)0.0810 (19)0.0014 (12)0.0046 (14)−0.0045 (14)
C50.0659 (15)0.0577 (15)0.0817 (19)0.0030 (12)0.0130 (14)0.0013 (14)
C10.0472 (13)0.095 (2)0.0732 (18)0.0015 (13)0.0148 (13)0.0141 (16)
C60.0760 (18)0.0686 (17)0.102 (2)0.0186 (15)0.0177 (17)0.0211 (17)
C220.0902 (19)0.0528 (15)0.083 (2)0.0022 (14)0.0155 (16)−0.0109 (15)
C20.0608 (16)0.087 (2)0.080 (2)−0.0032 (14)−0.0005 (15)−0.0080 (16)
C210.143 (3)0.130 (3)0.0617 (19)−0.051 (2)0.033 (2)−0.021 (2)
Geometric parameters (Å, º) top
Cl2—C151.745 (2)C14—C151.377 (3)
Cl1—C11.739 (3)C14—C131.383 (3)
O2—C191.316 (3)C14—H140.9300
O2—C201.466 (3)C10—H10A0.9700
C12—C131.382 (3)C10—H10B0.9700
C12—C171.383 (3)C15—C161.367 (3)
C12—C111.519 (3)C8—H8A0.9700
C18—N11.442 (3)C8—H8B0.9700
C18—C191.529 (3)C13—H130.9300
C18—C111.556 (3)C20—C211.441 (4)
C18—C71.584 (3)C20—H20A0.9700
N1—C221.144 (3)C20—H20B0.9700
C11—C101.523 (3)C16—H160.9300
C11—H110.9800C3—C21.376 (4)
C4—C31.373 (3)C3—H30.9300
C4—C51.382 (3)C5—C61.388 (4)
C4—C71.513 (3)C5—H50.9300
O1—C191.191 (3)C1—C21.352 (4)
C7—C81.532 (3)C1—C61.365 (4)
C7—H70.9800C6—H60.9300
C9—O31.205 (3)C2—H20.9300
C9—C101.500 (3)C21—H21A0.9600
C9—C81.502 (3)C21—H21B0.9600
C17—C161.378 (3)C21—H21C0.9600
C17—H170.9300
C19—O2—C20117.11 (18)H10A—C10—H10B108.0
C13—C12—C17118.1 (2)C16—C15—C14120.7 (2)
C13—C12—C11122.58 (19)C16—C15—Cl2119.88 (19)
C17—C12—C11119.21 (19)C14—C15—Cl2119.39 (18)
N1—C18—C19106.80 (16)C9—C8—C7110.72 (19)
N1—C18—C11109.33 (17)C9—C8—H8A109.5
C19—C18—C11109.64 (16)C7—C8—H8A109.5
N1—C18—C7107.07 (16)C9—C8—H8B109.5
C19—C18—C7113.03 (17)C7—C8—H8B109.5
C11—C18—C7110.82 (15)H8A—C8—H8B108.1
C22—N1—C18177.6 (2)C12—C13—C14121.2 (2)
C12—C11—C10114.26 (17)C12—C13—H13119.4
C12—C11—C18114.07 (16)C14—C13—H13119.4
C10—C11—C18109.69 (16)C21—C20—O2109.8 (2)
C12—C11—H11106.0C21—C20—H20A109.7
C10—C11—H11106.0O2—C20—H20A109.7
C18—C11—H11106.0C21—C20—H20B109.7
C3—C4—C5116.7 (2)O2—C20—H20B109.7
C3—C4—C7122.3 (2)H20A—C20—H20B108.2
C5—C4—C7120.9 (2)C15—C16—C17119.6 (2)
C4—C7—C8114.22 (18)C15—C16—H16120.2
C4—C7—C18114.57 (17)C17—C16—H16120.2
C8—C7—C18111.65 (16)C4—C3—C2122.4 (3)
C4—C7—H7105.1C4—C3—H3118.8
C8—C7—H7105.1C2—C3—H3118.8
C18—C7—H7105.1C4—C5—C6121.4 (3)
O1—C19—O2126.2 (2)C4—C5—H5119.3
O1—C19—C18124.5 (2)C6—C5—H5119.3
O2—C19—C18109.36 (17)C2—C1—C6120.4 (3)
O3—C9—C10122.4 (2)C2—C1—Cl1119.6 (2)
O3—C9—C8122.6 (2)C6—C1—Cl1120.0 (2)
C10—C9—C8114.99 (18)C1—C6—C5119.5 (3)
C16—C17—C12121.2 (2)C1—C6—H6120.2
C16—C17—H17119.4C5—C6—H6120.2
C12—C17—H17119.4C1—C2—C3119.6 (3)
C15—C14—C13119.1 (2)C1—C2—H2120.2
C15—C14—H14120.4C3—C2—H2120.2
C13—C14—H14120.4C20—C21—H21A109.5
C9—C10—C11111.22 (18)C20—C21—H21B109.5
C9—C10—H10A109.4H21A—C21—H21B109.5
C11—C10—H10A109.4C20—C21—H21C109.5
C9—C10—H10B109.4H21A—C21—H21C109.5
C11—C10—H10B109.4H21B—C21—H21C109.5
C19—C18—N1—C22−164 (6)C7—C18—C19—O259.8 (2)
C11—C18—N1—C2278 (6)C13—C12—C17—C16−1.5 (3)
C7—C18—N1—C22−43 (6)C11—C12—C17—C16175.7 (2)
C13—C12—C11—C1041.3 (3)O3—C9—C10—C11−160.1 (2)
C17—C12—C11—C10−135.7 (2)C8—C9—C10—C1120.6 (3)
C13—C12—C11—C18−86.0 (2)C12—C11—C10—C9166.34 (18)
C17—C12—C11—C1896.9 (2)C18—C11—C10—C9−64.1 (2)
N1—C18—C11—C1255.2 (2)C13—C14—C15—C16−2.0 (4)
C19—C18—C11—C12−61.5 (2)C13—C14—C15—Cl2177.18 (17)
C7—C18—C11—C12173.01 (17)O3—C9—C8—C7−139.3 (2)
N1—C18—C11—C10−74.4 (2)C10—C9—C8—C740.1 (3)
C19—C18—C11—C10168.84 (17)C4—C7—C8—C9169.06 (18)
C7—C18—C11—C1043.4 (2)C18—C7—C8—C9−58.9 (2)
C3—C4—C7—C811.8 (3)C17—C12—C13—C141.1 (3)
C5—C4—C7—C8−164.7 (2)C11—C12—C13—C14−176.0 (2)
C3—C4—C7—C18−118.7 (2)C15—C14—C13—C120.7 (3)
C5—C4—C7—C1864.7 (3)C19—O2—C20—C21140.9 (3)
N1—C18—C7—C4−93.2 (2)C14—C15—C16—C171.6 (4)
C19—C18—C7—C424.1 (2)Cl2—C15—C16—C17−177.61 (19)
C11—C18—C7—C4147.63 (18)C12—C17—C16—C150.2 (4)
N1—C18—C7—C8134.96 (19)C5—C4—C3—C21.1 (4)
C19—C18—C7—C8−107.7 (2)C7—C4—C3—C2−175.6 (2)
C11—C18—C7—C815.8 (2)C3—C4—C5—C6−0.8 (4)
C20—O2—C19—O1−0.1 (3)C7—C4—C5—C6176.0 (2)
C20—O2—C19—C18179.17 (17)C2—C1—C6—C51.3 (4)
N1—C18—C19—O1−3.5 (3)Cl1—C1—C6—C5−177.6 (2)
C11—C18—C19—O1114.8 (2)C4—C5—C6—C1−0.4 (4)
C7—C18—C19—O1−121.0 (2)C6—C1—C2—C3−1.0 (4)
N1—C18—C19—O2177.26 (16)Cl1—C1—C2—C3178.0 (2)
C11—C18—C19—O2−64.4 (2)C4—C3—C2—C1−0.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.982.573.218 (3)123
Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.982.573.218 (3)123
Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.
 

Acknowledgements

Financial support of this research by the Science and Technology Development Program Foundation of Jilin Province (No. 20140204022NY) and the Inter­disciplinary Innovation Fund of Jilin University (No. 450060481143) is gratefully acknowledged.

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Volume 70| Part 7| July 2014| Page o802
https://doi.org/10.1107/S160053681401383X
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