4-(4-Meth­oxy­phen­yl)-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/S1600536811033897

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2470

doi:10.1107/S1600536811033897

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4-(4-Methoxyphenyl)-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, C₂₁H₁₆N₂O₂, 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 19.7 (1)°. The 4-substituted aromatic ring is bent away from the pyridine ring by 50.3 (1)° in order to avoid crowding the cyanide substituent. In the crystal, 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

C₂₁H₁₆N₂O₂
M_r = 328.36
Monoclinic, P 2₁ /c
a = 14.2016 (2) Å
b = 14.4725 (2) Å
c = 7.9935 (1) Å
β = 96.017 (1)°
V = 1633.87 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.818, T_max = 0.873
6187 measured reflections
3211 independent reflections
3011 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.096
S = 1.03
3211 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.90 (2)	1.94 (2)	2.823 (1)	166 (1)
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/S1600536811033897/xu5292sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033897/xu5292Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033897/xu5292Isup3.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 19.7 (1)°. The 4-subsituted aromatic ring is bent away from the pyridine ring by 50.3 (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 p-anisaldehyde (1.36 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. 587–589 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 C₂₁H₁₆N₂O₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₂₁H₁₆N₂O₂	F(000) = 688
M_r = 328.36	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4172 reflections
a = 14.2016 (2) Å	θ = 3.1–74.1°
b = 14.4725 (2) Å	µ = 0.70 mm⁻¹
c = 7.9935 (1) Å	T = 100 K
β = 96.017 (1)°	Prism, yellow
V = 1633.87 (4) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3211 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3011 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.014
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.2°, θ_min = 4.4°
ω scans	h = −17→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→17
T_min = 0.818, T_max = 0.873	l = −9→9
6187 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0566P)² + 0.481P] where P = (F_o² + 2F_c²)/3
3211 reflections	(Δ/σ)_max = 0.001
230 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₁H₁₆N₂O₂	V = 1633.87 (4) Å³
M_r = 328.36	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 14.2016 (2) Å	µ = 0.70 mm⁻¹
b = 14.4725 (2) Å	T = 100 K
c = 7.9935 (1) Å	0.30 × 0.25 × 0.20 mm
β = 96.017 (1)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3211 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3011 reflections with I > 2σ(I)
T_min = 0.818, T_max = 0.873	R_int = 0.014
6187 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.21 e Å⁻³
3211 reflections	Δρ_min = −0.21 e Å⁻³
230 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.38937 (5)	0.48227 (6)	0.53692 (9)	0.01885 (19)
O2	−0.13689 (6)	0.71903 (6)	0.05350 (12)	0.0263 (2)
N1	0.42821 (6)	0.55604 (6)	0.30260 (11)	0.0154 (2)
H1	0.4886 (11)	0.5401 (11)	0.3377 (19)	0.026 (4)*
N2	0.15375 (7)	0.53084 (7)	0.58833 (12)	0.0215 (2)
C1	0.40584 (8)	0.60068 (7)	0.15327 (13)	0.0150 (2)
C2	0.48272 (8)	0.62138 (7)	0.04885 (13)	0.0159 (2)
C3	0.57808 (8)	0.62155 (8)	0.11363 (14)	0.0186 (2)
H3	0.5951	0.6082	0.2292	0.022*
C4	0.64792 (8)	0.64118 (8)	0.00983 (15)	0.0218 (2)
H4	0.7127	0.6404	0.0540	0.026*
C5	0.62308 (9)	0.66197 (8)	−0.15877 (15)	0.0228 (3)
H5	0.6708	0.6763	−0.2294	0.027*
C6	0.52862 (8)	0.66177 (8)	−0.22408 (14)	0.0208 (2)
H6	0.5122	0.6759	−0.3395	0.025*
C7	0.45770 (8)	0.64121 (7)	−0.12269 (13)	0.0168 (2)
C8	0.35509 (8)	0.63521 (8)	−0.19115 (13)	0.0184 (2)
H8A	0.3387	0.5700	−0.2181	0.022*
H8B	0.3447	0.6714	−0.2965	0.022*
C9	0.29074 (8)	0.67172 (8)	−0.06574 (13)	0.0178 (2)
H9A	0.2994	0.7393	−0.0531	0.021*
H9B	0.2239	0.6599	−0.1085	0.021*
C10	0.31283 (7)	0.62548 (7)	0.10368 (13)	0.0151 (2)
C11	0.24237 (7)	0.60637 (7)	0.21242 (13)	0.0150 (2)
C12	0.26806 (7)	0.55905 (7)	0.36226 (13)	0.0149 (2)
C13	0.36372 (7)	0.52863 (7)	0.40914 (13)	0.0151 (2)
C14	0.20310 (7)	0.54250 (7)	0.48475 (13)	0.0159 (2)
C15	0.14293 (7)	0.63712 (7)	0.16970 (13)	0.0153 (2)
C16	0.12282 (8)	0.72862 (7)	0.12434 (13)	0.0161 (2)
H16	0.1736	0.7709	0.1196	0.019*
C17	0.03069 (8)	0.75948 (8)	0.08598 (14)	0.0177 (2)
H17	0.0184	0.8223	0.0569	0.021*
C18	−0.04357 (7)	0.69700 (8)	0.09073 (14)	0.0181 (2)
C19	−0.02511 (8)	0.60501 (8)	0.13544 (14)	0.0193 (2)
H19	−0.0759	0.5626	0.1386	0.023*
C20	0.06719 (8)	0.57570 (8)	0.17509 (13)	0.0174 (2)
H20	0.0793	0.5132	0.2063	0.021*
C21	−0.15928 (8)	0.81389 (9)	0.01842 (17)	0.0261 (3)
H21A	−0.2279	0.8207	−0.0075	0.039*
H21B	−0.1275	0.8344	−0.0781	0.039*
H21C	−0.1378	0.8516	0.1169	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0173 (4)	0.0238 (4)	0.0149 (4)	0.0045 (3)	−0.0007 (3)	0.0043 (3)
O2	0.0117 (4)	0.0218 (4)	0.0445 (5)	0.0017 (3)	−0.0010 (3)	0.0067 (4)
N1	0.0124 (4)	0.0186 (5)	0.0147 (4)	0.0027 (3)	−0.0015 (3)	0.0015 (3)
N2	0.0212 (5)	0.0219 (5)	0.0217 (5)	0.0001 (4)	0.0034 (4)	0.0016 (4)
C1	0.0168 (5)	0.0133 (5)	0.0141 (5)	0.0009 (4)	−0.0014 (4)	−0.0011 (4)
C2	0.0160 (5)	0.0136 (5)	0.0178 (5)	0.0014 (4)	0.0004 (4)	0.0001 (4)
C3	0.0179 (5)	0.0175 (5)	0.0199 (5)	0.0004 (4)	−0.0005 (4)	0.0024 (4)
C4	0.0157 (5)	0.0212 (6)	0.0281 (6)	−0.0009 (4)	0.0009 (4)	0.0022 (5)
C5	0.0221 (6)	0.0220 (6)	0.0254 (6)	−0.0017 (4)	0.0079 (4)	0.0020 (4)
C6	0.0252 (6)	0.0194 (5)	0.0181 (5)	0.0008 (4)	0.0032 (4)	0.0019 (4)
C7	0.0191 (5)	0.0143 (5)	0.0167 (5)	0.0017 (4)	0.0009 (4)	−0.0002 (4)
C8	0.0189 (5)	0.0224 (5)	0.0134 (5)	0.0023 (4)	−0.0009 (4)	0.0013 (4)
C9	0.0173 (5)	0.0208 (5)	0.0148 (5)	0.0033 (4)	−0.0004 (4)	0.0019 (4)
C10	0.0155 (5)	0.0151 (5)	0.0142 (5)	0.0011 (4)	−0.0013 (4)	−0.0006 (4)
C11	0.0157 (5)	0.0128 (5)	0.0156 (5)	0.0001 (4)	−0.0023 (4)	−0.0025 (4)
C12	0.0144 (5)	0.0147 (5)	0.0152 (5)	0.0005 (4)	−0.0003 (4)	−0.0010 (4)
C13	0.0162 (5)	0.0151 (5)	0.0138 (5)	0.0015 (4)	−0.0002 (4)	−0.0010 (4)
C14	0.0153 (5)	0.0141 (5)	0.0172 (5)	0.0014 (4)	−0.0038 (4)	−0.0003 (4)
C15	0.0146 (5)	0.0180 (5)	0.0128 (5)	0.0012 (4)	−0.0012 (4)	−0.0007 (4)
C16	0.0139 (5)	0.0175 (5)	0.0165 (5)	−0.0018 (4)	−0.0006 (4)	−0.0004 (4)
C17	0.0172 (5)	0.0155 (5)	0.0199 (5)	0.0009 (4)	−0.0003 (4)	0.0015 (4)
C18	0.0119 (5)	0.0206 (6)	0.0212 (5)	0.0016 (4)	−0.0013 (4)	0.0011 (4)
C19	0.0147 (5)	0.0186 (5)	0.0240 (6)	−0.0030 (4)	−0.0003 (4)	0.0006 (4)
C20	0.0179 (5)	0.0153 (5)	0.0183 (5)	0.0004 (4)	−0.0011 (4)	0.0008 (4)
C21	0.0168 (5)	0.0229 (6)	0.0383 (7)	0.0060 (5)	0.0012 (5)	0.0064 (5)

Geometric parameters (Å, º) top

O1—C13	1.2443 (13)	C8—H8B	0.9900
O2—C18	1.3653 (13)	C9—C10	1.5137 (14)
O2—C21	1.4304 (14)	C9—H9A	0.9900
N1—C1	1.3652 (13)	C9—H9B	0.9900
N1—C13	1.3729 (14)	C10—C11	1.4197 (15)
N1—H1	0.904 (16)	C11—C12	1.3947 (15)
N2—C14	1.1519 (15)	C11—C15	1.4859 (14)
C1—C10	1.3859 (15)	C12—C14	1.4341 (15)
C1—C2	1.4729 (15)	C12—C13	1.4399 (14)
C2—C3	1.3984 (15)	C15—C16	1.3947 (15)
C2—C7	1.4095 (15)	C15—C20	1.3994 (15)
C3—C4	1.3875 (16)	C16—C17	1.3860 (15)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.3898 (17)	C17—C18	1.3928 (16)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.3875 (17)	C18—C19	1.3961 (16)
C5—H5	0.9500	C19—C20	1.3826 (15)
C6—C7	1.3896 (16)	C19—H19	0.9500
C6—H6	0.9500	C20—H20	0.9500
C7—C8	1.5044 (15)	C21—H21A	0.9800
C8—C9	1.5204 (15)	C21—H21B	0.9800
C8—H8A	0.9900	C21—H21C	0.9800

C18—O2—C21	117.24 (9)	C1—C10—C11	119.10 (9)
C1—N1—C13	124.74 (9)	C1—C10—C9	118.18 (10)
C1—N1—H1	121.2 (10)	C11—C10—C9	122.72 (9)
C13—N1—H1	114.0 (9)	C12—C11—C10	118.93 (9)
N1—C1—C10	120.00 (10)	C12—C11—C15	120.07 (10)
N1—C1—C2	118.25 (9)	C10—C11—C15	120.99 (9)
C10—C1—C2	121.74 (9)	C11—C12—C14	122.63 (10)
C3—C2—C7	119.70 (10)	C11—C12—C13	121.90 (10)
C3—C2—C1	122.49 (10)	C14—C12—C13	115.35 (9)
C7—C2—C1	117.81 (10)	O1—C13—N1	120.54 (10)
C4—C3—C2	120.28 (10)	O1—C13—C12	124.44 (10)
C4—C3—H3	119.9	N1—C13—C12	115.01 (9)
C2—C3—H3	119.9	N2—C14—C12	177.04 (11)
C3—C4—C5	119.97 (11)	C16—C15—C20	118.30 (10)
C3—C4—H4	120.0	C16—C15—C11	120.52 (10)
C5—C4—H4	120.0	C20—C15—C11	121.18 (10)
C6—C5—C4	120.10 (11)	C17—C16—C15	121.76 (10)
C6—C5—H5	119.9	C17—C16—H16	119.1
C4—C5—H5	119.9	C15—C16—H16	119.1
C5—C6—C7	120.81 (10)	C16—C17—C18	118.99 (10)
C5—C6—H6	119.6	C16—C17—H17	120.5
C7—C6—H6	119.6	C18—C17—H17	120.5
C6—C7—C2	119.13 (10)	O2—C18—C17	124.26 (10)
C6—C7—C8	122.27 (10)	O2—C18—C19	115.50 (10)
C2—C7—C8	118.55 (10)	C17—C18—C19	120.24 (10)
C7—C8—C9	111.49 (9)	C20—C19—C18	119.96 (10)
C7—C8—H8A	109.3	C20—C19—H19	120.0
C9—C8—H8A	109.3	C18—C19—H19	120.0
C7—C8—H8B	109.3	C19—C20—C15	120.75 (10)
C9—C8—H8B	109.3	C19—C20—H20	119.6
H8A—C8—H8B	108.0	C15—C20—H20	119.6
C10—C9—C8	110.71 (9)	O2—C21—H21A	109.5
C10—C9—H9A	109.5	O2—C21—H21B	109.5
C8—C9—H9A	109.5	H21A—C21—H21B	109.5
C10—C9—H9B	109.5	O2—C21—H21C	109.5
C8—C9—H9B	109.5	H21A—C21—H21C	109.5
H9A—C9—H9B	108.1	H21B—C21—H21C	109.5

C13—N1—C1—C10	3.20 (16)	C1—C10—C11—C15	175.99 (9)
C13—N1—C1—C2	−176.95 (9)	C9—C10—C11—C15	−4.29 (16)
N1—C1—C2—C3	−18.44 (15)	C10—C11—C12—C14	175.55 (9)
C10—C1—C2—C3	161.41 (10)	C15—C11—C12—C14	−3.61 (16)
N1—C1—C2—C7	161.30 (10)	C10—C11—C12—C13	−0.36 (16)
C10—C1—C2—C7	−18.86 (15)	C15—C11—C12—C13	−179.53 (9)
C7—C2—C3—C4	0.04 (16)	C1—N1—C13—O1	174.67 (10)
C1—C2—C3—C4	179.77 (10)	C1—N1—C13—C12	−6.45 (15)
C2—C3—C4—C5	0.84 (17)	C11—C12—C13—O1	−176.24 (10)
C3—C4—C5—C6	−0.96 (18)	C14—C12—C13—O1	7.56 (16)
C4—C5—C6—C7	0.19 (18)	C11—C12—C13—N1	4.93 (15)
C5—C6—C7—C2	0.69 (17)	C14—C12—C13—N1	−171.27 (9)
C5—C6—C7—C8	−176.55 (11)	C12—C11—C15—C16	128.40 (11)
C3—C2—C7—C6	−0.80 (16)	C10—C11—C15—C16	−50.74 (14)
C1—C2—C7—C6	179.46 (10)	C12—C11—C15—C20	−51.08 (14)
C3—C2—C7—C8	176.55 (10)	C10—C11—C15—C20	129.78 (11)
C1—C2—C7—C8	−3.20 (15)	C20—C15—C16—C17	0.34 (16)
C6—C7—C8—C9	−144.07 (11)	C11—C15—C16—C17	−179.16 (10)
C2—C7—C8—C9	38.67 (14)	C15—C16—C17—C18	−0.89 (16)
C7—C8—C9—C10	−52.36 (12)	C21—O2—C18—C17	−4.32 (17)
N1—C1—C10—C11	1.94 (15)	C21—O2—C18—C19	175.79 (10)
C2—C1—C10—C11	−177.91 (9)	C16—C17—C18—O2	−179.15 (10)
N1—C1—C10—C9	−177.80 (9)	C16—C17—C18—C19	0.73 (16)
C2—C1—C10—C9	2.36 (15)	O2—C18—C19—C20	179.86 (10)
C8—C9—C10—C1	33.28 (13)	C17—C18—C19—C20	−0.04 (17)
C8—C9—C10—C11	−146.44 (10)	C18—C19—C20—C15	−0.53 (17)
C1—C10—C11—C12	−3.17 (15)	C16—C15—C20—C19	0.38 (16)
C9—C10—C11—C12	176.55 (10)	C11—C15—C20—C19	179.87 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.90 (2)	1.94 (2)	2.823 (1)	166 (1)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆N₂O₂
M_r	328.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.2016 (2), 14.4725 (2), 7.9935 (1)
β (°)	96.017 (1)
V (Å³)	1633.87 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.818, 0.873
No. of measured, independent and observed [I > 2σ(I)] reflections	6187, 3211, 3011
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.096, 1.03
No. of reflections	3211
No. of parameters	230
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21

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	0.90 (2)	1.94 (2)	2.823 (1)	166 (1)

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 o2470

doi:10.1107/S1600536811033897

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

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