Ethyl (Z)-2-cyano-3-(9-ethyl-9H-carbazol-3-yl)prop-2-enoate

Asiri, A.M.; Akkurt, M.; Khan, S.A.; Khan, I.U.; Arshad, M.N.

doi:10.1107/S1600536809015505

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1169

doi:10.1107/S1600536809015505

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Ethyl (Z)-2-cyano-3-(9-ethyl-9H-carbazol-3-yl)prop-2-enoate

Abdullah Mohamed Asiri,^a Mehmet Akkurt,^b ^* Salman A. Khan,^a Islam Ullah Khan ^c and Muhammad N. Arshad ^c

^aChemistry Department, Faculty of Science, King Abdul-Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^cDepartment of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 22 April 2009; accepted 25 April 2009; online 30 April 2009)

In the title compound, C₂₀H₁₈N₂O₂, weak intermolecular C—H⋯O and C—H⋯N interactions generate a chain that runs parallel to the b axis and incorporates C(7) and R₂²(15) graph-set motifs. The supramolecular aggregation is completed by the presence of weak C—H⋯π interactions.

Related literature

For background to the applications of carbazole derivatives, see: Park et al. (1998 ); Kimoto et al. (2004 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₁₈N₂O₂
M_r = 318.36
Monoclinic, P 2₁ /n
a = 10.8030 (7) Å
b = 13.4443 (10) Å
c = 11.6160 (7) Å
β = 93.387 (5)°
V = 1684.15 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.35 × 0.10 × 0.05 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
19261 measured reflections
4195 independent reflections
1121 reflections with I > 2σ(I)
R_int = 0.146

Refinement

R[F² > 2σ(F²)] = 0.084
wR(F²) = 0.228
S = 0.91
4195 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1ⁱ	0.93	2.58	3.255 (5)	130
C12—H12⋯N2ⁱⁱ	0.93	2.58	3.491 (6)	165
C17—H17B⋯Cg2ⁱⁱⁱ	0.97	2.82	3.692 (5)	150
Symmetry codes: (i) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ . Cg2 is the centroid of the C7–C12 ring.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015505/hb2957sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015505/hb2957Isup2.hkl

checkCIF report

Comment top

Nonlinear optical (NLO) andelectro-optic (EO) properties of organic dyes have been the hot subject nowadays because of the potential applications in optical switching, optical telecommunication devices, optical disks, new type of dye lasers (Kimoto et al., 2004). Carbazole derivatives have important roles of optical material due to their special photorefractive, electrical, and chemical properties. Carbazoles are well known as a conjugated, good hole transporting, electron-donor, planar compound and easy to introduce solubilizing groups to rigid ring structure (Park et al., 1998).

The molecular structure of title compound (I) is shown in Fig. 1. The bond lengths and angles in (I) display normal values (Allen et al., 1987). The nine-membered ring N1/C1—C8 is essentially planar, with maximum deviations of 0.014 (5)Åfor C5 and -0.025 (4) Å for C7 from its mean plane, respectively. In the molecule of (I), the rest atoms of the molecule lie close to the nine-membered ring plane, with the maximum deviations of 1.110 (7), -0.467 (3) and -0.341 (5) Å, for C20, O1 and C18, respectively.

The crystal structure of (I) is stabilized by weak C—H···O and C—H···N interactions (Table 1, Fig. 2), that generates a chain which runs parallel to the baxis and has the graph-set motifs of C(7) and R₂²(15). The supramolecular aggregation is completed by the presence of C—H···π interactions (Table 1).

Related literature top

For background to the applications of carbazole derivatives, see: Park et al. (1998); Kimoto et al. (2004). For reference structural data, see: Allen et al. (1987). Cg2 is the centroid of the C7–C12 ring.

Experimental top

Equivalent molar quantities of N-ethyl carbazol-9-carboxaldehyde (1.0 g, 4.48 mmol) and ethylcyanoacetate (0.51 g, 4.48 mmol) were dissolved in 25 ml e thanol then heated at reflux. Pipyridine (one drop) was added to the solution and reflux was continued for 6 h. The solution was cooled to room temperature and the solid products were filtered and washed with ethanol (25 ml). Recrystalization from ethanol gave yellow prisms of (I). Yield: (0.4 g, 29%); m.p. 385 K; IR (KBr) ν_maxcm^-1. 3028 (C—H aromatic), 2978 (–C—H aliphatic), 2216 (CN), 1721(C=O), 1573 (C=C), 1225 (C—O), 1127 (C—N).). ¹H NMR(CDCl₃): δ 8.15 (H-1), 8.19 (H-2), 8.41(H-3), 7.45 (H-4), 7.33 (H-5), 7.54 (H-6), 7.45 (H-7), 8.74 (H-8), 4.39 (CH₃—CH₂—N), 1.41 (CH₃—CH₂—N), 4.39 (CH₃—CH₂—O), 1.41 (CH₃—CH₂—O).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I), showing 30% displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. View of the unit cell of (I), viewed along the c axis, showing the network of hydrogen bonds.

Ethyl (Z)-2-cyano-3-(9-ethyl-9H-carbazol-3-yl)prop-2-enoate top

Crystal data top

C₂₀H₁₈N₂O₂	F(000) = 672
M_r = 318.36	D_x = 1.256 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1000 reflections
a = 10.8030 (7) Å	θ = 2.3–18.8°
b = 13.4443 (10) Å	µ = 0.08 mm⁻¹
c = 11.6160 (7) Å	T = 296 K
β = 93.387 (5)°	Prism, yellow
V = 1684.15 (19) Å³	0.35 × 0.10 × 0.05 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	1121 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.146
Graphite monochromator	θ_max = 28.4°, θ_min = 2.3°
ω scans	h = −14→14
19261 measured reflections	k = −17→17
4195 independent reflections	l = −15→15

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.228	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.0844P)²] where P = (F_o² + 2F_c²)/3
4195 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₁₈N₂O₂	V = 1684.15 (19) Å³
M_r = 318.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.8030 (7) Å	µ = 0.08 mm⁻¹
b = 13.4443 (10) Å	T = 296 K
c = 11.6160 (7) Å	0.35 × 0.10 × 0.05 mm
β = 93.387 (5)°

Data collection top

Bruker SMART CCD diffractometer	1121 reflections with I > 2σ(I)
19261 measured reflections	R_int = 0.146
4195 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	0 restraints
wR(F²) = 0.228	H-atom parameters constrained
S = 0.91	Δρ_max = 0.32 e Å⁻³
4195 reflections	Δρ_min = −0.23 e Å⁻³
221 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O1	1.4145 (3)	0.8481 (2)	0.1597 (3)	0.0835 (14)
O2	1.5181 (3)	0.70597 (19)	0.1392 (2)	0.0621 (12)
N1	0.7557 (3)	0.6264 (3)	0.3838 (4)	0.0812 (19)
N2	1.3601 (4)	0.5077 (3)	0.2087 (4)	0.102 (2)
C1	0.7049 (4)	0.7186 (3)	0.4082 (4)	0.0608 (19)
C2	0.5892 (4)	0.7421 (4)	0.4444 (4)	0.085 (2)
C3	0.5636 (4)	0.8400 (4)	0.4611 (4)	0.087 (3)
C4	0.6497 (5)	0.9127 (4)	0.4426 (4)	0.079 (2)
C5	0.7649 (4)	0.8899 (3)	0.4064 (4)	0.0641 (19)
C6	0.7937 (4)	0.7906 (3)	0.3871 (3)	0.0502 (17)
C7	0.9004 (4)	0.7407 (3)	0.3476 (3)	0.0483 (17)
C8	0.8738 (4)	0.6380 (3)	0.3497 (4)	0.0571 (17)
C9	0.9580 (4)	0.5671 (3)	0.3175 (4)	0.0713 (19)
C10	1.0695 (4)	0.5990 (3)	0.2815 (3)	0.0613 (19)
C11	1.0991 (4)	0.7019 (3)	0.2751 (3)	0.0520 (17)
C12	1.0125 (4)	0.7700 (3)	0.3092 (3)	0.0520 (16)
C13	1.2138 (4)	0.7387 (3)	0.2355 (3)	0.0544 (16)
C14	1.3189 (4)	0.6959 (3)	0.2050 (3)	0.0526 (17)
C15	1.3401 (4)	0.5905 (4)	0.2063 (4)	0.0690 (19)
C16	1.4198 (4)	0.7584 (3)	0.1657 (4)	0.0579 (17)
C17	1.6223 (4)	0.7618 (3)	0.1012 (4)	0.0669 (17)
C18	1.7166 (4)	0.6885 (4)	0.0645 (4)	0.088 (2)
C19	0.6800 (6)	0.5253 (5)	0.3793 (6)	0.131 (3)
C20	0.6995 (6)	0.4966 (5)	0.4914 (6)	0.148 (4)
H2	0.53090	0.69290	0.45680	0.1020*
H3	0.48630	0.85800	0.48560	0.1040*
H4	0.62930	0.97890	0.45490	0.0950*
H5	0.82260	0.93980	0.39510	0.0770*
H9	0.93920	0.49970	0.32020	0.0860*
H10	1.12760	0.55220	0.26070	0.0740*
H12	1.03080	0.83750	0.30600	0.0620*
H13	1.21550	0.80770	0.22980	0.0650*
H17A	1.65730	0.80300	0.16350	0.0800*
H17B	1.59600	0.80470	0.03720	0.0800*
H18A	1.74330	0.64750	0.12900	0.1320*
H18B	1.78650	0.72350	0.03720	0.1320*
H18C	1.68040	0.64740	0.00390	0.1320*
H19A	0.59270	0.53590	0.35850	0.1570*
H19B	0.71370	0.47770	0.32670	0.1570*
H20A	0.78660	0.48700	0.50880	0.2220*
H20B	0.65620	0.43550	0.50350	0.2220*
H20C	0.66930	0.54720	0.54090	0.2220*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.078 (2)	0.046 (2)	0.130 (3)	−0.0031 (17)	0.0351 (19)	0.0023 (19)
O2	0.051 (2)	0.056 (2)	0.081 (2)	−0.0006 (16)	0.0186 (16)	0.0005 (15)
N1	0.066 (3)	0.039 (3)	0.142 (4)	−0.016 (2)	0.036 (2)	0.001 (2)
N2	0.092 (3)	0.052 (3)	0.165 (5)	0.015 (2)	0.042 (3)	0.006 (3)
C1	0.057 (3)	0.043 (3)	0.084 (4)	−0.004 (2)	0.017 (3)	−0.003 (2)
C2	0.058 (3)	0.071 (4)	0.128 (5)	−0.001 (3)	0.029 (3)	0.000 (3)
C3	0.062 (4)	0.077 (4)	0.124 (5)	0.016 (3)	0.027 (3)	−0.005 (3)
C4	0.074 (4)	0.059 (3)	0.107 (4)	0.014 (3)	0.021 (3)	−0.002 (3)
C5	0.060 (3)	0.054 (3)	0.080 (4)	0.010 (2)	0.019 (3)	0.002 (2)
C6	0.050 (3)	0.045 (3)	0.057 (3)	0.005 (2)	0.015 (2)	0.000 (2)
C7	0.052 (3)	0.043 (3)	0.051 (3)	−0.003 (2)	0.012 (2)	0.000 (2)
C8	0.049 (3)	0.046 (3)	0.078 (3)	−0.015 (2)	0.019 (2)	0.001 (2)
C9	0.065 (3)	0.036 (3)	0.116 (4)	−0.001 (3)	0.032 (3)	−0.004 (2)
C10	0.060 (3)	0.039 (3)	0.087 (4)	0.002 (2)	0.022 (3)	−0.006 (2)
C11	0.051 (3)	0.041 (3)	0.065 (3)	−0.004 (2)	0.012 (2)	0.000 (2)
C12	0.059 (3)	0.034 (2)	0.064 (3)	−0.003 (2)	0.013 (2)	−0.001 (2)
C13	0.059 (3)	0.038 (2)	0.067 (3)	−0.003 (2)	0.010 (2)	0.002 (2)
C14	0.050 (3)	0.039 (3)	0.070 (3)	0.001 (2)	0.014 (2)	−0.001 (2)
C15	0.059 (3)	0.056 (3)	0.095 (4)	0.004 (3)	0.031 (3)	0.001 (3)
C16	0.052 (3)	0.050 (3)	0.073 (3)	0.000 (3)	0.016 (2)	0.000 (2)
C17	0.050 (3)	0.074 (3)	0.078 (3)	−0.009 (3)	0.014 (3)	0.003 (3)
C18	0.068 (3)	0.094 (4)	0.103 (4)	0.012 (3)	0.020 (3)	0.009 (3)
C19	0.123 (5)	0.164 (7)	0.110 (6)	0.062 (5)	0.041 (5)	0.026 (5)
C20	0.156 (7)	0.134 (6)	0.156 (8)	0.028 (5)	0.023 (6)	−0.008 (5)

Geometric parameters (Å, º) top

O1—C16	1.209 (5)	C14—C15	1.435 (7)
O2—C16	1.326 (5)	C14—C16	1.470 (6)
O2—C17	1.444 (5)	C17—C18	1.497 (6)
N1—C1	1.392 (6)	C19—C20	1.363 (10)
N1—C8	1.367 (6)	C2—H2	0.9300
N1—C19	1.586 (8)	C3—H3	0.9300
N2—C15	1.134 (7)	C4—H4	0.9300
C1—C2	1.379 (6)	C5—H5	0.9300
C1—C6	1.395 (6)	C9—H9	0.9300
C2—C3	1.361 (8)	C10—H10	0.9300
C3—C4	1.375 (7)	C12—H12	0.9300
C4—C5	1.372 (7)	C13—H13	0.9300
C5—C6	1.392 (6)	C17—H17A	0.9700
C6—C7	1.432 (6)	C17—H17B	0.9700
C7—C8	1.411 (6)	C18—H18A	0.9600
C7—C12	1.373 (6)	C18—H18B	0.9600
C8—C9	1.384 (6)	C18—H18C	0.9600
C9—C10	1.367 (6)	C19—H19A	0.9700
C10—C11	1.423 (6)	C19—H19B	0.9700
C11—C12	1.384 (6)	C20—H20A	0.9600
C11—C13	1.435 (6)	C20—H20B	0.9600
C13—C14	1.339 (6)	C20—H20C	0.9600

C16—O2—C17	116.4 (3)	C3—C2—H2	121.00
C1—N1—C8	110.1 (4)	C2—C3—H3	119.00
C1—N1—C19	124.2 (4)	C4—C3—H3	119.00
C8—N1—C19	125.2 (4)	C3—C4—H4	119.00
N1—C1—C2	129.9 (4)	C5—C4—H4	119.00
N1—C1—C6	107.4 (4)	C4—C5—H5	121.00
C2—C1—C6	122.7 (4)	C6—C5—H5	121.00
C1—C2—C3	117.4 (4)	C8—C9—H9	121.00
C2—C3—C4	121.3 (4)	C10—C9—H9	121.00
C3—C4—C5	121.6 (5)	C9—C10—H10	119.00
C4—C5—C6	118.6 (4)	C11—C10—H10	119.00
C1—C6—C5	118.3 (4)	C7—C12—H12	119.00
C1—C6—C7	107.8 (4)	C11—C12—H12	119.00
C5—C6—C7	133.8 (4)	C11—C13—H13	113.00
C6—C7—C8	106.5 (4)	C14—C13—H13	113.00
C6—C7—C12	135.4 (4)	O2—C17—H17A	110.00
C8—C7—C12	118.1 (4)	O2—C17—H17B	110.00
N1—C8—C7	108.1 (4)	C18—C17—H17A	110.00
N1—C8—C9	129.7 (4)	C18—C17—H17B	110.00
C7—C8—C9	122.1 (4)	H17A—C17—H17B	108.00
C8—C9—C10	118.1 (4)	C17—C18—H18A	109.00
C9—C10—C11	121.7 (4)	C17—C18—H18B	109.00
C10—C11—C12	118.1 (4)	C17—C18—H18C	109.00
C10—C11—C13	123.6 (4)	H18A—C18—H18B	109.00
C12—C11—C13	118.4 (4)	H18A—C18—H18C	109.00
C7—C12—C11	121.8 (4)	H18B—C18—H18C	110.00
C11—C13—C14	134.3 (4)	N1—C19—H19A	112.00
C13—C14—C15	124.0 (4)	N1—C19—H19B	112.00
C13—C14—C16	119.5 (4)	C20—C19—H19A	112.00
C15—C14—C16	116.5 (4)	C20—C19—H19B	112.00
N2—C15—C14	178.1 (5)	H19A—C19—H19B	110.00
O1—C16—O2	123.6 (4)	C19—C20—H20A	109.00
O1—C16—C14	123.7 (4)	C19—C20—H20B	109.00
O2—C16—C14	112.8 (3)	C19—C20—H20C	109.00
O2—C17—C18	107.5 (3)	H20A—C20—H20B	110.00
N1—C19—C20	99.3 (5)	H20A—C20—H20C	109.00
C1—C2—H2	121.00	H20B—C20—H20C	109.00

C17—O2—C16—O1	−0.2 (6)	C1—C6—C7—C12	176.6 (4)
C17—O2—C16—C14	−179.2 (3)	C5—C6—C7—C8	178.3 (4)
C16—O2—C17—C18	−174.2 (4)	C5—C6—C7—C12	−3.3 (8)
C8—N1—C1—C2	179.6 (5)	C6—C7—C8—N1	2.4 (5)
C8—N1—C1—C6	0.8 (5)	C6—C7—C8—C9	−179.4 (4)
C19—N1—C1—C2	7.6 (8)	C12—C7—C8—N1	−176.4 (4)
C19—N1—C1—C6	−171.1 (5)	C12—C7—C8—C9	1.8 (6)
C1—N1—C8—C7	−2.1 (5)	C6—C7—C12—C11	−179.5 (4)
C1—N1—C8—C9	180.0 (5)	C8—C7—C12—C11	−1.1 (6)
C19—N1—C8—C7	169.8 (5)	N1—C8—C9—C10	177.0 (5)
C19—N1—C8—C9	−8.2 (8)	C7—C8—C9—C10	−0.8 (7)
C1—N1—C19—C20	−90.6 (6)	C8—C9—C10—C11	−0.9 (6)
C8—N1—C19—C20	98.7 (6)	C9—C10—C11—C12	1.5 (6)
N1—C1—C2—C3	−179.5 (5)	C9—C10—C11—C13	−178.6 (4)
C6—C1—C2—C3	−0.9 (7)	C10—C11—C12—C7	−0.4 (5)
N1—C1—C6—C5	−179.4 (4)	C13—C11—C12—C7	179.7 (3)
N1—C1—C6—C7	0.7 (5)	C10—C11—C13—C14	−5.7 (7)
C2—C1—C6—C5	1.7 (6)	C12—C11—C13—C14	174.2 (4)
C2—C1—C6—C7	−178.2 (4)	C11—C13—C14—C15	−0.1 (7)
C1—C2—C3—C4	0.0 (7)	C11—C13—C14—C16	179.0 (4)
C2—C3—C4—C5	0.1 (7)	C13—C14—C16—O1	0.6 (7)
C3—C4—C5—C6	0.7 (7)	C13—C14—C16—O2	179.6 (3)
C4—C5—C6—C1	−1.5 (6)	C15—C14—C16—O1	179.7 (4)
C4—C5—C6—C7	178.3 (4)	C15—C14—C16—O2	−1.3 (5)
C1—C6—C7—C8	−1.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.93	2.58	3.255 (5)	130
C12—H12···N2ⁱⁱ	0.93	2.58	3.491 (6)	165
C17—H17B···Cg2ⁱⁱⁱ	0.97	2.82	3.692 (5)	150

Symmetry codes: (i) −x+5/2, y−1/2, −z+1/2; (ii) −x+5/2, y+1/2, −z+1/2; (iii) x+1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₂O₂
M_r	318.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.8030 (7), 13.4443 (10), 11.6160 (7)
β (°)	93.387 (5)
V (Å³)	1684.15 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19261, 4195, 1121
R_int	0.146
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.228, 0.91
No. of reflections	4195
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.23

Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.93	2.58	3.255 (5)	130
C12—H12···N2ⁱⁱ	0.93	2.58	3.491 (6)	165
C17—H17B···Cg2ⁱⁱⁱ	0.97	2.82	3.692 (5)	150

Symmetry codes: (i) −x+5/2, y−1/2, −z+1/2; (ii) −x+5/2, y+1/2, −z+1/2; (iii) x+1/2, −y+3/2, z−1/2.

Acknowledgements

AMA acknowledges the Deanship of Scientific Research at KAU for grant No. 3–50/429.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2003). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kimoto, A., Cho, J. S., Higuchi, M. & Yamamoto, K. (2004). Macromolecules, 37, 5531–5537. Web of Science CrossRef CAS Google Scholar
Park, K. H., Yeon, K. M., Lee, M. Y., Lee, S. D., Shin, D. H., Lee, C. J. & Kim, N. (1998). Polymer, 39, 7061–7066. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar