2-[3-(2-Chloro­phen­yl)-5-oxo-1,5-diphenyl­pentyl­idene]malononitrile

Du, B.-X.; Zhou, J.; Li, Y.-L.; Wang, X.-S.

doi:10.1107/S1600536810050622

organic compounds

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Volume 67| Part 1| January 2011| Page o62

https://doi.org/10.1107/S1600536810050622

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2-[3-(2-Chlorophenyl)-5-oxo-1,5-diphenylpentylidene]malononitrile

Bai-Xiang Du,^a ^* Jie Zhou,^a Yu-Ling Li ^a and Xiang-Shan Wang ^a

^aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou Jiangsu 221116, People's Republic of China
^*Correspondence e-mail: dbx19722@xznu.edu.cn

(Received 25 November 2010; accepted 3 December 2010; online 11 December 2010)

In the title compound, C₂₆H₁₉ClN₂O, the 2-chlorophenyl group forms dihedral angles of 59.6 (1) and 31.9 (1)° with the phenyl rings. The two phenyl rings are inclined at a dihedral angle of 32.9 (1)° with respect to each other. In the crystal, an intermolecular C—H⋯N hydrogen bond links the molecules into a polymeric chain running along the c axis.

Related literature

For water as an attractive medium for organic reactions, see: Breslow (1991 ). For a related structure, see: Zhou et al. (2007 ).

Experimental

Crystal data

C₂₆H₁₉ClN₂O
M_r = 410.88
Orthorhombic, P b c a
a = 12.4450 (3) Å
b = 14.3866 (3) Å
c = 24.1913 (5) Å
V = 4331.24 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.50 × 0.39 × 0.29 mm

Data collection

Bruker SMART CCD area-detector diffractometer
34193 measured reflections
5019 independent reflections
2972 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.153
S = 1.04
5019 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯N1ⁱ	0.97	2.62	3.502 (3)	152
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810050622/pv2363sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050622/pv2363Isup2.hkl

checkCIF report

Comment top

There has been a growing recognition that water has become an attractive medium for many organic reactions (Breslow, 1991). Recently, we have demonstrated the Michal addition reaction between 2-(1-phenylethylidene)malononitrile and 1-phenyl-3-(2-chlorophenyl)propen-1-one in water without a catalyst and synthesized the title compound which is reported in this article.

In the title compound (Fig. 1), 2-chlorophenyl group forms dihedral angles of 59.6 (1) and 31.9 (1) ° with benzene rings (C1—C6) and (C15—C20), respectively. The two benzene rings are inclined with respect to each other at a dihedral angle of 32.9 (1) °. There is an intermolecular hydrogen bond C8—H8A···N1 (Table 1) resulting in a polymeric chain along the c-axis. In addition, two intramolecular interactions further stabilize the structure (Fig. 2).

Related literature top

For water as an attractive medium for organic reactions, see: Breslow (1991). For a related structure, see: Zhou et al. (2007).

Experimental top

The title compound was prepared by the reaction of 2-(1-phenylethylidene)malononitrile (0.168 g, 1.0 mmol) and 1-phenyl-3-(2-chlorophenyl)propen-1-one (0.242 g, 1.0 mmol) in water (10 ml) at reflux for 14 h (yield 82%, mp. 438–439 K). Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a dimethylformamide solution.

Structure description top

For water as an attractive medium for organic reactions, see: Breslow (1991). For a related structure, see: Zhou et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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

	Fig. 1. The molecular structure drawing for the title compound; displacement ellipsoids are drawn at 20% probability level.
	Fig. 2. The molecular packing diagram of the title compound showing intermolecular and intramolecular interactions by dashed lines.

2-[3-(2-Chlorophenyl)-5-oxo-1,5-diphenylpentylidene]malononitrile top

Crystal data top

C₂₆H₁₉ClN₂O	D_x = 1.260 Mg m⁻³
M_r = 410.88	Melting point = 438–439 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5457 reflections
a = 12.4450 (3) Å	θ = 2.7–22.0°
b = 14.3866 (3) Å	µ = 0.20 mm⁻¹
c = 24.1913 (5) Å	T = 296 K
V = 4331.24 (16) Å³	Block, orange
Z = 8	0.50 × 0.39 × 0.29 mm
F(000) = 1712

Data collection top

Bruker SMART CCD area-detector diffractometer	2972 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 27.6°, θ_min = 1.7°
φ and ω scans	h = −14→16
34193 measured reflections	k = −16→18
5019 independent reflections	l = −31→31

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0713P)² + 0.4979P] where P = (F_o² + 2F_c²)/3
5019 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₆H₁₉ClN₂O	V = 4331.24 (16) Å³
M_r = 410.88	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.4450 (3) Å	µ = 0.20 mm⁻¹
b = 14.3866 (3) Å	T = 296 K
c = 24.1913 (5) Å	0.50 × 0.39 × 0.29 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2972 reflections with I > 2σ(I)
34193 measured reflections	R_int = 0.042
5019 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
5019 reflections	Δρ_min = −0.27 e Å⁻³
271 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.39311 (5)	0.00962 (5)	0.68110 (3)	0.0971 (3)
C9	0.21419 (13)	0.09876 (11)	0.61061 (7)	0.0520 (4)
H9A	0.2428	0.1139	0.6473	0.062*
C8	0.10322 (13)	0.05493 (12)	0.61832 (8)	0.0560 (4)
H8A	0.0692	0.0488	0.5824	0.067*
H8B	0.1121	−0.0071	0.6334	0.067*
C21	0.29056 (14)	0.03111 (11)	0.58342 (8)	0.0556 (5)
C10	0.20485 (14)	0.18975 (11)	0.57755 (8)	0.0557 (4)
H10A	0.1812	0.1751	0.5403	0.067*
H10B	0.1501	0.2284	0.5945	0.067*
C11	0.30676 (14)	0.24393 (10)	0.57417 (8)	0.0544 (4)
C6	−0.08495 (15)	0.08221 (13)	0.66065 (8)	0.0572 (5)
C22	0.37359 (15)	−0.01196 (12)	0.61140 (10)	0.0678 (5)
C12	0.34607 (16)	0.27063 (12)	0.52452 (8)	0.0625 (5)
C15	0.35978 (16)	0.27215 (12)	0.62569 (8)	0.0610 (5)
O1	0.06454 (13)	0.17514 (13)	0.68188 (7)	0.1005 (6)
C7	0.03017 (16)	0.10937 (13)	0.65567 (8)	0.0615 (5)
N1	0.50586 (17)	0.38254 (14)	0.51232 (9)	0.0950 (6)
C13	0.43597 (18)	0.33273 (14)	0.51864 (9)	0.0727 (6)
C24	0.4281 (2)	−0.09442 (16)	0.53127 (15)	0.0962 (8)
H24A	0.4745	−0.1357	0.5137	0.115*
C1	−0.12962 (17)	0.00934 (14)	0.63200 (10)	0.0752 (6)
H1A	−0.0876	−0.0250	0.6076	0.090*
C20	0.2988 (2)	0.30836 (13)	0.66865 (8)	0.0747 (6)
H20A	0.2244	0.3114	0.6654	0.090*
C16	0.4708 (2)	0.26488 (16)	0.63205 (11)	0.0878 (7)
H16A	0.5128	0.2394	0.6041	0.105*
C26	0.27768 (18)	0.00750 (12)	0.52708 (10)	0.0721 (6)
H26A	0.2221	0.0341	0.5069	0.087*
C14	0.2967 (2)	0.24452 (15)	0.47332 (11)	0.0852 (7)
C5	−0.14936 (19)	0.13109 (16)	0.69652 (9)	0.0805 (6)
H5A	−0.1202	0.1799	0.7167	0.097*
C23	0.44248 (17)	−0.07472 (15)	0.58579 (13)	0.0880 (7)
H23A	0.4976	−0.1028	0.6057	0.106*
C25	0.3458 (2)	−0.05403 (15)	0.50173 (11)	0.0889 (7)
H25A	0.3365	−0.0685	0.4646	0.107*
C2	−0.2366 (2)	−0.01304 (19)	0.63923 (12)	0.0981 (8)
H2A	−0.2663	−0.0624	0.6197	0.118*
C3	−0.2987 (2)	0.0365 (2)	0.67466 (11)	0.0947 (8)
H3A	−0.3705	0.0207	0.6795	0.114*
C4	−0.25626 (19)	0.1091 (2)	0.70305 (10)	0.0921 (7)
H4A	−0.2992	0.1438	0.7268	0.111*
C18	0.4571 (4)	0.3335 (2)	0.72144 (15)	0.1327 (15)
H18A	0.4900	0.3550	0.7535	0.159*
N2	0.2593 (3)	0.22584 (17)	0.43153 (10)	0.1295 (10)
C17	0.5177 (3)	0.2960 (2)	0.68043 (17)	0.1288 (13)
H17A	0.5917	0.2912	0.6849	0.155*
C19	0.3479 (3)	0.33966 (17)	0.71595 (11)	0.1089 (10)
H19A	0.3068	0.3651	0.7443	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0767 (4)	0.1071 (5)	0.1076 (5)	0.0193 (3)	−0.0259 (3)	0.0111 (4)
C9	0.0472 (10)	0.0470 (9)	0.0617 (10)	0.0028 (7)	−0.0016 (8)	0.0037 (7)
C8	0.0494 (10)	0.0497 (9)	0.0687 (11)	0.0002 (8)	0.0018 (8)	0.0032 (8)
C21	0.0473 (10)	0.0425 (8)	0.0771 (12)	−0.0043 (7)	0.0066 (9)	0.0054 (8)
C10	0.0528 (11)	0.0448 (9)	0.0695 (11)	0.0022 (7)	−0.0056 (9)	0.0027 (8)
C11	0.0537 (11)	0.0370 (8)	0.0724 (12)	0.0059 (7)	−0.0006 (9)	0.0003 (8)
C6	0.0515 (11)	0.0589 (10)	0.0611 (11)	0.0043 (8)	0.0024 (8)	0.0024 (8)
C22	0.0484 (11)	0.0523 (10)	0.1027 (16)	0.0010 (8)	0.0065 (10)	0.0106 (10)
C12	0.0688 (12)	0.0474 (9)	0.0714 (12)	0.0021 (9)	0.0110 (10)	−0.0048 (9)
C15	0.0651 (12)	0.0435 (9)	0.0744 (13)	−0.0092 (8)	−0.0103 (10)	0.0107 (8)
O1	0.0712 (10)	0.1136 (13)	0.1167 (13)	−0.0219 (9)	0.0164 (9)	−0.0566 (11)
C7	0.0538 (11)	0.0636 (11)	0.0671 (12)	−0.0002 (9)	0.0001 (9)	−0.0066 (9)
N1	0.0909 (15)	0.0822 (13)	0.1118 (16)	−0.0147 (11)	0.0316 (12)	0.0016 (11)
C13	0.0747 (14)	0.0588 (12)	0.0846 (15)	0.0030 (11)	0.0227 (12)	−0.0024 (10)
C24	0.0767 (17)	0.0579 (13)	0.154 (3)	0.0045 (12)	0.0416 (18)	−0.0098 (15)
C1	0.0578 (13)	0.0751 (13)	0.0927 (15)	−0.0047 (10)	0.0077 (11)	−0.0159 (11)
C20	0.0963 (17)	0.0591 (12)	0.0689 (13)	−0.0124 (11)	−0.0060 (12)	0.0020 (10)
C16	0.0694 (15)	0.0785 (14)	0.1154 (19)	−0.0124 (12)	−0.0217 (14)	0.0221 (13)
C26	0.0755 (14)	0.0498 (10)	0.0912 (15)	0.0016 (9)	0.0152 (12)	0.0004 (10)
C14	0.118 (2)	0.0643 (13)	0.0733 (15)	−0.0065 (12)	0.0138 (14)	−0.0044 (11)
C5	0.0680 (14)	0.0882 (15)	0.0854 (15)	−0.0005 (12)	0.0126 (12)	−0.0168 (12)
C23	0.0545 (13)	0.0653 (13)	0.144 (2)	0.0088 (10)	0.0151 (14)	0.0067 (15)
C25	0.1003 (19)	0.0621 (13)	0.1042 (18)	−0.0081 (13)	0.0309 (15)	−0.0117 (12)
C2	0.0648 (15)	0.1060 (19)	0.124 (2)	−0.0228 (13)	0.0044 (15)	−0.0243 (16)
C3	0.0535 (14)	0.124 (2)	0.1068 (19)	−0.0112 (14)	0.0122 (13)	0.0044 (17)
C4	0.0614 (14)	0.1157 (19)	0.0992 (17)	0.0068 (14)	0.0222 (13)	−0.0104 (15)
C18	0.194 (4)	0.107 (2)	0.098 (2)	−0.067 (3)	−0.067 (3)	0.0279 (19)
N2	0.206 (3)	0.1064 (17)	0.0766 (15)	−0.0285 (19)	−0.0054 (16)	−0.0090 (13)
C17	0.110 (3)	0.121 (3)	0.155 (3)	−0.048 (2)	−0.071 (2)	0.050 (2)
C19	0.173 (3)	0.0812 (16)	0.0730 (16)	−0.0366 (19)	−0.0189 (19)	0.0037 (12)

Geometric parameters (Å, º) top

Cl1—C22	1.732 (3)	C24—C25	1.378 (4)
C9—C21	1.511 (2)	C24—H24A	0.9300
C9—C8	1.530 (2)	C1—C2	1.381 (3)
C9—C10	1.538 (2)	C1—H1A	0.9300
C9—H9A	0.9800	C20—C19	1.373 (3)
C8—C7	1.502 (3)	C20—H20A	0.9300
C8—H8A	0.9700	C16—C17	1.382 (4)
C8—H8B	0.9700	C16—H16A	0.9300
C21—C22	1.382 (3)	C26—C25	1.371 (3)
C21—C26	1.414 (3)	C26—H26A	0.9300
C10—C11	1.491 (2)	C14—N2	1.145 (3)
C10—H10A	0.9700	C5—C4	1.377 (3)
C10—H10B	0.9700	C5—H5A	0.9300
C11—C12	1.353 (2)	C23—H23A	0.9300
C11—C15	1.468 (3)	C25—H25A	0.9300
C6—C1	1.374 (3)	C2—C3	1.357 (4)
C6—C5	1.375 (3)	C2—H2A	0.9300
C6—C7	1.490 (3)	C3—C4	1.356 (4)
C22—C23	1.391 (3)	C3—H3A	0.9300
C12—C14	1.433 (3)	C4—H4A	0.9300
C12—C13	1.439 (3)	C18—C17	1.357 (5)
C15—C20	1.388 (3)	C18—C19	1.369 (5)
C15—C16	1.394 (3)	C18—H18A	0.9300
O1—C7	1.217 (2)	C17—H17A	0.9300
N1—C13	1.137 (3)	C19—H19A	0.9300
C24—C23	1.361 (4)

C21—C9—C8	110.83 (13)	C25—C24—H24A	119.6
C21—C9—C10	111.67 (14)	C6—C1—C2	120.3 (2)
C8—C9—C10	110.24 (13)	C6—C1—H1A	119.9
C21—C9—H9A	108.0	C2—C1—H1A	119.9
C8—C9—H9A	108.0	C19—C20—C15	120.2 (3)
C10—C9—H9A	108.0	C19—C20—H20A	119.9
C7—C8—C9	113.89 (15)	C15—C20—H20A	119.9
C7—C8—H8A	108.8	C17—C16—C15	119.2 (3)
C9—C8—H8A	108.8	C17—C16—H16A	120.4
C7—C8—H8B	108.8	C15—C16—H16A	120.4
C9—C8—H8B	108.8	C25—C26—C21	121.1 (2)
H8A—C8—H8B	107.7	C25—C26—H26A	119.5
C22—C21—C26	116.69 (18)	C21—C26—H26A	119.5
C22—C21—C9	123.08 (18)	N2—C14—C12	177.7 (3)
C26—C21—C9	120.21 (17)	C6—C5—C4	121.2 (2)
C11—C10—C9	114.15 (14)	C6—C5—H5A	119.4
C11—C10—H10A	108.7	C4—C5—H5A	119.4
C9—C10—H10A	108.7	C24—C23—C22	119.1 (2)
C11—C10—H10B	108.7	C24—C23—H23A	120.5
C9—C10—H10B	108.7	C22—C23—H23A	120.5
H10A—C10—H10B	107.6	C26—C25—C24	120.0 (3)
C12—C11—C15	120.85 (17)	C26—C25—H25A	120.0
C12—C11—C10	120.33 (17)	C24—C25—H25A	120.0
C15—C11—C10	118.72 (16)	C3—C2—C1	120.4 (2)
C1—C6—C5	118.21 (19)	C3—C2—H2A	119.8
C1—C6—C7	123.25 (17)	C1—C2—H2A	119.8
C5—C6—C7	118.53 (18)	C2—C3—C4	120.2 (2)
C21—C22—C23	122.3 (2)	C2—C3—H3A	119.9
C21—C22—Cl1	120.10 (16)	C4—C3—H3A	119.9
C23—C22—Cl1	117.62 (18)	C3—C4—C5	119.7 (2)
C11—C12—C14	122.55 (18)	C3—C4—H4A	120.2
C11—C12—C13	123.06 (19)	C5—C4—H4A	120.2
C14—C12—C13	114.25 (19)	C17—C18—C19	120.4 (3)
C20—C15—C16	119.2 (2)	C17—C18—H18A	119.8
C20—C15—C11	119.59 (18)	C19—C18—H18A	119.8
C16—C15—C11	121.2 (2)	C18—C17—C16	120.8 (3)
O1—C7—C6	119.99 (18)	C18—C17—H17A	119.6
O1—C7—C8	120.41 (18)	C16—C17—H17A	119.6
C6—C7—C8	119.60 (16)	C18—C19—C20	120.1 (3)
N1—C13—C12	177.8 (3)	C18—C19—H19A	120.0
C23—C24—C25	120.8 (2)	C20—C19—H19A	120.0
C23—C24—H24A	119.6

C21—C9—C8—C7	167.52 (15)	C11—C12—C13—N1	−157 (6)
C10—C9—C8—C7	−68.3 (2)	C14—C12—C13—N1	19 (6)
C8—C9—C21—C22	−107.58 (19)	C5—C6—C1—C2	0.4 (3)
C10—C9—C21—C22	129.09 (17)	C7—C6—C1—C2	179.0 (2)
C8—C9—C21—C26	71.0 (2)	C16—C15—C20—C19	2.4 (3)
C10—C9—C21—C26	−52.3 (2)	C11—C15—C20—C19	−176.51 (18)
C21—C9—C10—C11	−63.88 (19)	C20—C15—C16—C17	−1.6 (3)
C8—C9—C10—C11	172.46 (15)	C11—C15—C16—C17	177.3 (2)
C9—C10—C11—C12	126.58 (17)	C22—C21—C26—C25	−1.0 (3)
C9—C10—C11—C15	−56.9 (2)	C9—C21—C26—C25	−179.72 (17)
C26—C21—C22—C23	0.7 (3)	C11—C12—C14—N2	166 (8)
C9—C21—C22—C23	179.38 (17)	C13—C12—C14—N2	−9 (8)
C26—C21—C22—Cl1	−177.92 (13)	C1—C6—C5—C4	−1.1 (3)
C9—C21—C22—Cl1	0.7 (2)	C7—C6—C5—C4	−179.8 (2)
C15—C11—C12—C14	179.97 (18)	C25—C24—C23—C22	−0.9 (4)
C10—C11—C12—C14	−3.6 (3)	C21—C22—C23—C24	0.2 (3)
C15—C11—C12—C13	−4.6 (3)	Cl1—C22—C23—C24	178.89 (18)
C10—C11—C12—C13	171.84 (16)	C21—C26—C25—C24	0.4 (3)
C12—C11—C15—C20	132.33 (19)	C23—C24—C25—C26	0.6 (3)
C10—C11—C15—C20	−44.1 (2)	C6—C1—C2—C3	0.0 (4)
C12—C11—C15—C16	−46.5 (2)	C1—C2—C3—C4	0.5 (4)
C10—C11—C15—C16	137.02 (17)	C2—C3—C4—C5	−1.2 (4)
C1—C6—C7—O1	179.4 (2)	C6—C5—C4—C3	1.6 (4)
C5—C6—C7—O1	−2.0 (3)	C19—C18—C17—C16	1.1 (5)
C1—C6—C7—C8	−0.8 (3)	C15—C16—C17—C18	−0.1 (4)
C5—C6—C7—C8	177.80 (18)	C17—C18—C19—C20	−0.3 (4)
C9—C8—C7—O1	−8.8 (3)	C15—C20—C19—C18	−1.4 (4)
C9—C8—C7—C6	171.45 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N1ⁱ	0.97	2.62	3.502 (3)	152
C9—H9A···Cl1	0.98	2.53	3.083 (3)	115
C10—H10B···O1	0.97	2.48	3.071 (4)	119

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₉ClN₂O
M_r	410.88
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	12.4450 (3), 14.3866 (3), 24.1913 (5)
V (Å³)	4331.24 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.50 × 0.39 × 0.29

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	34193, 5019, 2972
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.153, 1.04
No. of reflections	5019
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.27

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N1ⁱ	0.97	2.62	3.502 (3)	151.8
C9—H9A···Cl1	0.98	2.53	3.083 (3)	115.3
C10—H10B···O1	0.97	2.48	3.071 (4)	119.1

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Acknowledgements

We are grateful to the Natural Science Foundation (08KJD150019) and the Qing Lan Project (08QLT001) of the Jiangsu Education Committee for financial support.

References

Breslow, R. (1991). Acc. Chem. Res. 24, 159–164. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhou, J.-X., Wang, X.-S. & Shi, D.-Q. (2007). Acta Cryst. E63, o2082–o2083. Web of Science CSD CrossRef IUCr Journals Google Scholar