4-(1,3-Benzodioxol-5-yl)-2-oxo-1,2,5,6-tetra­hydro­benzo[h]quinoline-3-carbo­nitrile

Asiri, A.M.; Faidallah, H.M.; Al-Youbi, A.O.; Alamry, K.A.; Ng, S.W.

doi:10.1107/S1600536811033903

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2471

doi:10.1107/S1600536811033903

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4-(1,3-Benzodioxol-5-yl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile

Abdullah M. Asiri,^a Hassan M. Faidallah,^a Abdulrahman O. Al-Youbi,^a Khalid A. Alamry ^a and Seik Weng Ng ^b,^a ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 7 August 2011; accepted 19 August 2011; online 27 August 2011)

In the molecule of the title compound, C₂₁H₁₄N₂O₃, the tetrahydrobenzo[h]quinoline fused-ring system is buckled owing to the ethylene –CH₂CH₂– fragment, the benzene ring and the pyridine ring being twisted by 24.3 (1)°. The ring of the benzodioxol system is bent away from the pyridine ring by 61.4 (1)° in order to avoid crowding the cyanide substituent. Two molecules are linked by a pair of N—H⋯O hydrogen bonds to form a centrosymmetric dimer.

Related literature

For background to the anticancer properties of this class of compounds, see: Rostom et al. (2011 ).

Experimental

Crystal data

C₂₁H₁₄N₂O₃
M_r = 342.34
Monoclinic, P 2₁ /n
a = 7.6586 (3) Å
b = 16.5858 (5) Å
c = 13.3220 (6) Å
β = 104.164 (4)°
V = 1640.77 (11) Å³
Z = 4
Cu Kα radiation
μ = 0.77 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.802, T_max = 0.963
6078 measured reflections
3241 independent reflections
2962 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.100
S = 1.02
3241 reflections
239 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.93 (2)	1.85 (2)	2.778 (1)	175 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033903/xu5293sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033903/xu5293Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033903/xu5293Isup3.cml

checkCIF report

Comment top

The compound (Scheme I) belongs to a series of cyano-pyridinones that have been evaluated for their anticancer properties (Rostom et al., 2011). The tetrahydrobenzo[h]quinoline fused-ring system is buckled owing to the ethylene –CH₂CH₂– fragment, the benzene ring and the pyridine ring being twisted by 24.3 (1)°. The 4-subsituted aromatic ring is bent away from the pyridine ring by 61.4 (1) ° in order to avoid crowding the cyanide substituent (Fig. 1). Two molecules are linked by an N—H···O hydrogen bonds to form a centrosymmetric dimer (Table 1).

Related literature top

For background to the anticancer properties of this class of compounds, see: Rostom et al. (2011).

Experimental top

A mixture of piperonaldehyde (1.50 g, 10 mmol), 1-tetralone (1.46 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool, and the yellow precipitate that formed was filtered, washed with water, dried and recrystallized from ethanol; m.p. 593–595 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₁H₁₄N₂O₃ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

4-(1,3-Benzodioxol-5-yl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline- 3-carbonitrile top

Crystal data top

C₂₁H₁₄N₂O₃	F(000) = 712
M_r = 342.34	D_x = 1.386 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 3826 reflections
a = 7.6586 (3) Å	θ = 3.4–74.1°
b = 16.5858 (5) Å	µ = 0.77 mm⁻¹
c = 13.3220 (6) Å	T = 100 K
β = 104.164 (4)°	Prism, yellow
V = 1640.77 (11) Å³	0.30 × 0.20 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3241 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2962 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.014
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.3°, θ_min = 4.3°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −20→18
T_min = 0.802, T_max = 0.963	l = −12→16
6078 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0584P)² + 0.3916P] where P = (F_o² + 2F_c²)/3
3241 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₁H₁₄N₂O₃	V = 1640.77 (11) Å³
M_r = 342.34	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 7.6586 (3) Å	µ = 0.77 mm⁻¹
b = 16.5858 (5) Å	T = 100 K
c = 13.3220 (6) Å	0.30 × 0.20 × 0.05 mm
β = 104.164 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3241 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2962 reflections with I > 2σ(I)
T_min = 0.802, T_max = 0.963	R_int = 0.014
6078 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.21 e Å⁻³
3241 reflections	Δρ_min = −0.22 e Å⁻³
239 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.70432 (10)	0.53335 (5)	0.56250 (6)	0.0240 (2)
O2	1.17132 (13)	0.94538 (6)	0.60416 (10)	0.0444 (3)
O3	1.07114 (12)	1.02058 (5)	0.72509 (8)	0.0325 (2)
N1	0.46189 (12)	0.61383 (6)	0.49726 (7)	0.0200 (2)
H1	0.400 (2)	0.5663 (10)	0.4755 (12)	0.036 (4)*
N2	1.07002 (14)	0.65042 (6)	0.67925 (9)	0.0305 (3)
C1	0.38331 (15)	0.68751 (7)	0.47365 (8)	0.0197 (2)
C2	0.19123 (15)	0.69051 (7)	0.41849 (9)	0.0210 (2)
C3	0.07235 (15)	0.62711 (7)	0.42051 (9)	0.0233 (2)
H3	0.1138	0.5799	0.4594	0.028*
C4	−0.10680 (16)	0.63304 (7)	0.36557 (10)	0.0270 (3)
H4	−0.1877	0.5899	0.3671	0.032*
C5	−0.16769 (16)	0.70217 (8)	0.30833 (10)	0.0288 (3)
H5	−0.2899	0.7060	0.2705	0.035*
C6	−0.05002 (16)	0.76546 (7)	0.30652 (9)	0.0268 (3)
H6	−0.0922	0.8124	0.2672	0.032*
C7	0.12963 (16)	0.76085 (7)	0.36181 (9)	0.0232 (2)
C8	0.26177 (16)	0.82766 (7)	0.36083 (10)	0.0282 (3)
H8A	0.1958	0.8789	0.3413	0.034*
H8B	0.3302	0.8158	0.3084	0.034*
C9	0.39269 (16)	0.83692 (7)	0.46727 (10)	0.0271 (3)
H9A	0.4852	0.8778	0.4636	0.032*
H9B	0.3266	0.8555	0.5182	0.032*
C10	0.48223 (15)	0.75711 (7)	0.50141 (9)	0.0210 (2)
C11	0.66347 (15)	0.75062 (7)	0.55957 (9)	0.0212 (2)
C12	0.74037 (15)	0.67503 (7)	0.57985 (9)	0.0212 (2)
C13	0.63948 (15)	0.60256 (7)	0.54712 (8)	0.0201 (2)
C14	0.92402 (15)	0.66289 (7)	0.63508 (9)	0.0228 (3)
C15	0.76691 (15)	0.82441 (6)	0.60147 (9)	0.0213 (2)
C16	0.92690 (16)	0.84474 (7)	0.57344 (10)	0.0252 (3)
H16	0.9722	0.8130	0.5261	0.030*
C17	1.01415 (15)	0.91297 (7)	0.61812 (10)	0.0262 (3)
C18	0.95379 (16)	0.95848 (7)	0.68946 (9)	0.0238 (2)
C19	0.79788 (16)	0.94009 (7)	0.71780 (9)	0.0250 (3)
H19	0.7560	0.9718	0.7665	0.030*
C20	0.70363 (16)	0.87202 (7)	0.67114 (9)	0.0239 (2)
H20	0.5935	0.8579	0.6875	0.029*
C21	1.20431 (18)	1.01643 (8)	0.66633 (11)	0.0346 (3)
H21A	1.1967	1.0647	0.6218	0.041*
H21B	1.3263	1.0143	0.7134	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0226 (4)	0.0149 (4)	0.0296 (4)	0.0014 (3)	−0.0028 (3)	0.0014 (3)
O2	0.0336 (5)	0.0346 (5)	0.0716 (8)	−0.0158 (4)	0.0256 (5)	−0.0236 (5)
O3	0.0289 (4)	0.0224 (4)	0.0442 (5)	−0.0065 (3)	0.0051 (4)	−0.0121 (4)
N1	0.0196 (5)	0.0147 (4)	0.0226 (5)	−0.0005 (4)	−0.0007 (4)	−0.0004 (4)
N2	0.0250 (5)	0.0230 (5)	0.0375 (6)	0.0003 (4)	−0.0040 (4)	−0.0018 (4)
C1	0.0213 (5)	0.0186 (5)	0.0181 (5)	0.0018 (4)	0.0027 (4)	−0.0002 (4)
C2	0.0204 (5)	0.0203 (5)	0.0205 (5)	0.0026 (4)	0.0018 (4)	−0.0029 (4)
C3	0.0224 (5)	0.0219 (6)	0.0240 (6)	0.0024 (4)	0.0027 (4)	−0.0020 (4)
C4	0.0216 (5)	0.0269 (6)	0.0306 (6)	−0.0011 (5)	0.0028 (5)	−0.0049 (5)
C5	0.0209 (5)	0.0296 (6)	0.0316 (6)	0.0046 (5)	−0.0019 (5)	−0.0058 (5)
C6	0.0250 (6)	0.0229 (6)	0.0281 (6)	0.0067 (5)	−0.0022 (5)	−0.0018 (5)
C7	0.0234 (5)	0.0209 (5)	0.0235 (5)	0.0030 (4)	0.0021 (4)	−0.0032 (4)
C8	0.0254 (6)	0.0209 (6)	0.0338 (7)	0.0033 (4)	−0.0013 (5)	0.0056 (5)
C9	0.0245 (6)	0.0164 (5)	0.0362 (7)	0.0022 (4)	−0.0005 (5)	−0.0007 (5)
C10	0.0218 (5)	0.0174 (5)	0.0226 (5)	0.0020 (4)	0.0031 (4)	−0.0010 (4)
C11	0.0233 (5)	0.0181 (5)	0.0211 (5)	0.0002 (4)	0.0031 (4)	−0.0015 (4)
C12	0.0200 (5)	0.0189 (5)	0.0219 (5)	−0.0004 (4)	−0.0003 (4)	0.0000 (4)
C13	0.0210 (5)	0.0181 (5)	0.0190 (5)	0.0012 (4)	0.0007 (4)	0.0010 (4)
C14	0.0250 (6)	0.0150 (5)	0.0260 (6)	−0.0006 (4)	0.0016 (5)	−0.0020 (4)
C15	0.0226 (5)	0.0157 (5)	0.0222 (5)	0.0007 (4)	−0.0010 (4)	−0.0002 (4)
C16	0.0243 (5)	0.0214 (6)	0.0291 (6)	0.0003 (4)	0.0050 (5)	−0.0060 (5)
C17	0.0219 (5)	0.0217 (6)	0.0343 (6)	−0.0022 (4)	0.0054 (5)	−0.0026 (5)
C18	0.0267 (6)	0.0147 (5)	0.0258 (6)	−0.0017 (4)	−0.0015 (4)	−0.0020 (4)
C19	0.0315 (6)	0.0195 (5)	0.0232 (6)	0.0009 (4)	0.0051 (5)	−0.0026 (4)
C20	0.0266 (6)	0.0189 (5)	0.0255 (6)	−0.0012 (4)	0.0050 (5)	0.0000 (4)
C21	0.0342 (7)	0.0237 (6)	0.0449 (8)	−0.0085 (5)	0.0081 (6)	−0.0066 (6)

Geometric parameters (Å, º) top

O1—C13	1.2477 (14)	C8—C9	1.5309 (17)
O2—C17	1.3718 (15)	C8—H8A	0.9900
O2—C21	1.4269 (16)	C8—H8B	0.9900
O3—C18	1.3730 (14)	C9—C10	1.5088 (15)
O3—C21	1.4312 (17)	C9—H9A	0.9900
N1—C1	1.3645 (14)	C9—H9B	0.9900
N1—C13	1.3725 (14)	C10—C11	1.4185 (15)
N1—H1	0.931 (17)	C11—C12	1.3834 (15)
N2—C14	1.1477 (15)	C11—C15	1.4902 (15)
C1—C10	1.3807 (15)	C12—C14	1.4331 (15)
C1—C2	1.4756 (15)	C12—C13	1.4377 (15)
C2—C3	1.3955 (16)	C15—C20	1.3928 (16)
C2—C7	1.4068 (16)	C15—C16	1.4065 (17)
C3—C4	1.3916 (16)	C16—C17	1.3736 (16)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.3928 (18)	C17—C18	1.3790 (17)
C4—H4	0.9500	C18—C19	1.3718 (17)
C5—C6	1.3875 (18)	C19—C20	1.4010 (16)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.3948 (15)	C20—H20	0.9500
C6—H6	0.9500	C21—H21A	0.9900
C7—C8	1.5029 (17)	C21—H21B	0.9900

C17—O2—C21	106.35 (10)	C1—C10—C11	118.83 (10)
C18—O3—C21	105.58 (9)	C1—C10—C9	118.27 (10)
C1—N1—C13	124.23 (9)	C11—C10—C9	122.89 (10)
C1—N1—H1	121.6 (10)	C12—C11—C10	119.24 (10)
C13—N1—H1	114.0 (10)	C12—C11—C15	120.61 (10)
N1—C1—C10	120.33 (10)	C10—C11—C15	120.11 (10)
N1—C1—C2	118.34 (10)	C11—C12—C14	123.03 (10)
C10—C1—C2	121.33 (10)	C11—C12—C13	121.79 (10)
C3—C2—C7	120.03 (10)	C14—C12—C13	115.17 (10)
C3—C2—C1	122.72 (10)	O1—C13—N1	120.82 (10)
C7—C2—C1	117.25 (10)	O1—C13—C12	123.82 (10)
C4—C3—C2	120.04 (11)	N1—C13—C12	115.36 (9)
C4—C3—H3	120.0	N2—C14—C12	177.69 (12)
C2—C3—H3	120.0	C20—C15—C16	120.58 (10)
C5—C4—C3	120.07 (11)	C20—C15—C11	118.39 (10)
C5—C4—H4	120.0	C16—C15—C11	121.02 (10)
C3—C4—H4	120.0	C17—C16—C15	116.46 (11)
C6—C5—C4	120.03 (11)	C17—C16—H16	121.8
C6—C5—H5	120.0	C15—C16—H16	121.8
C4—C5—H5	120.0	O2—C17—C16	127.88 (11)
C5—C6—C7	120.68 (11)	O2—C17—C18	109.40 (10)
C5—C6—H6	119.7	C16—C17—C18	122.68 (11)
C7—C6—H6	119.7	O3—C18—C19	127.72 (11)
C6—C7—C2	119.13 (11)	O3—C18—C17	110.33 (11)
C6—C7—C8	122.30 (10)	C19—C18—C17	121.95 (11)
C2—C7—C8	118.55 (10)	C18—C19—C20	116.47 (11)
C7—C8—C9	110.84 (10)	C18—C19—H19	121.8
C7—C8—H8A	109.5	C20—C19—H19	121.8
C9—C8—H8A	109.5	C15—C20—C19	121.81 (11)
C7—C8—H8B	109.5	C15—C20—H20	119.1
C9—C8—H8B	109.5	C19—C20—H20	119.1
H8A—C8—H8B	108.1	O2—C21—O3	107.97 (10)
C10—C9—C8	109.72 (10)	O2—C21—H21A	110.1
C10—C9—H9A	109.7	O3—C21—H21A	110.1
C8—C9—H9A	109.7	O2—C21—H21B	110.1
C10—C9—H9B	109.7	O3—C21—H21B	110.1
C8—C9—H9B	109.7	H21A—C21—H21B	108.4
H9A—C9—H9B	108.2

C13—N1—C1—C10	−1.05 (17)	C10—C11—C12—C13	−2.52 (17)
C13—N1—C1—C2	179.18 (10)	C15—C11—C12—C13	175.21 (10)
N1—C1—C2—C3	22.74 (16)	C1—N1—C13—O1	−177.03 (10)
C10—C1—C2—C3	−157.03 (11)	C1—N1—C13—C12	3.52 (16)
N1—C1—C2—C7	−156.96 (10)	C11—C12—C13—O1	178.92 (11)
C10—C1—C2—C7	23.27 (16)	C14—C12—C13—O1	−1.53 (17)
C7—C2—C3—C4	0.69 (17)	C11—C12—C13—N1	−1.66 (16)
C1—C2—C3—C4	−179.00 (10)	C14—C12—C13—N1	177.90 (10)
C2—C3—C4—C5	0.11 (18)	C12—C11—C15—C20	−116.89 (13)
C3—C4—C5—C6	−0.38 (19)	C10—C11—C15—C20	60.82 (15)
C4—C5—C6—C7	−0.15 (19)	C12—C11—C15—C16	61.65 (16)
C5—C6—C7—C2	0.94 (17)	C10—C11—C15—C16	−120.64 (12)
C5—C6—C7—C8	179.27 (12)	C20—C15—C16—C17	−0.08 (17)
C3—C2—C7—C6	−1.21 (17)	C11—C15—C16—C17	−178.59 (11)
C1—C2—C7—C6	178.50 (10)	C21—O2—C17—C16	179.29 (13)
C3—C2—C7—C8	−179.60 (11)	C21—O2—C17—C18	−2.82 (15)
C1—C2—C7—C8	0.11 (16)	C15—C16—C17—O2	179.76 (12)
C6—C7—C8—C9	143.06 (11)	C15—C16—C17—C18	2.13 (18)
C2—C7—C8—C9	−38.60 (15)	C21—O3—C18—C19	−176.17 (12)
C7—C8—C9—C10	54.40 (14)	C21—O3—C18—C17	4.47 (13)
N1—C1—C10—C11	−3.38 (17)	O2—C17—C18—O3	−1.08 (14)
C2—C1—C10—C11	176.38 (10)	C16—C17—C18—O3	176.94 (11)
N1—C1—C10—C9	175.95 (10)	O2—C17—C18—C19	179.52 (11)
C2—C1—C10—C9	−4.29 (16)	C16—C17—C18—C19	−2.46 (19)
C8—C9—C10—C1	−34.42 (15)	O3—C18—C19—C20	−178.70 (11)
C8—C9—C10—C11	144.89 (11)	C17—C18—C19—C20	0.59 (17)
C1—C10—C11—C12	5.05 (17)	C16—C15—C20—C19	−1.71 (17)
C9—C10—C11—C12	−174.25 (11)	C11—C15—C20—C19	176.83 (10)
C1—C10—C11—C15	−172.70 (10)	C18—C19—C20—C15	1.44 (17)
C9—C10—C11—C15	8.01 (17)	C17—O2—C21—O3	5.54 (15)
C10—C11—C12—C14	177.96 (10)	C18—O3—C21—O2	−6.13 (14)
C15—C11—C12—C14	−4.31 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.93 (2)	1.85 (2)	2.778 (1)	175 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄N₂O₃
M_r	342.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.6586 (3), 16.5858 (5), 13.3220 (6)
β (°)	104.164 (4)
V (Å³)	1640.77 (11)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.30 × 0.20 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.802, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	6078, 3241, 2962
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.100, 1.02
No. of reflections	3241
No. of parameters	239
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.93 (2)	1.85 (2)	2.778 (1)	175 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank King Abdulaziz University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Rostom, S. A. F., Faidallah, H. M. & Al-Saadi, M. S. (2011). Med. Chem. Res. 20 (DOI: 10.1007/s00044-010-9469-0). Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 9| September 2011| Page o2471

doi:10.1107/S1600536811033903

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

4-(1,3-Benzodioxol-5-yl)-2-oxo-1,2,5,6-tetra­hydro­benzo[h]quinoline-3-carbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(1,3-Benzodioxol-5-yl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile