4-(4-Chloro­phen­yl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7-octa­hydro­quinoline-3-carbonitrile

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

doi:10.1107/S1600536811036154

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2597

https://doi.org/10.1107/S1600536811036154

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4-(4-Chlorophenyl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7-octahydroquinoline-3-carbonitrile

Abdullah M. Asiri,^a,^b Abdulrahman O. Al-Youbi,^a Hassan M. Faidallah,^a Khadija O. Badahdah ^a and Seik Weng Ng ^c,^a ^*

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

(Received 5 September 2011; accepted 5 September 2011; online 14 September 2011)

The six-membered N-heterocyclic ring of title compound, C₁₇H₁₇ClN₂O, is fused with a methyl-substituted cyclohexene ring. The nitrogen-bearing ring has an envelope conformation with the benzene ring-bearing C atom lying 0.432 (6) Å out of the plane defined by the other five atoms (r.m.s. deviation 0.011 Å); its benzene substituent is aligned at 84.7 (1)° to the latter plane. The cyclohexene ring adopts a half-chair conformation. In the crystal, two molecules are linked about a center of inversion by pairs of N–H⋯O hydrogen bonds, generating dimers. An ethylene portion is disordered over two orientations in a 1:1 ratio. The crystal studied was a non-merohedral twin with a 15.3 (1)% minor component.

Related literature

For a similar compound that has two more H atoms, see: Asiri et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₇ClN₂O
M_r = 300.78
Monoclinic, P 2₁ /c
a = 11.0699 (7) Å
b = 7.6018 (3) Å
c = 18.2247 (9) Å
β = 100.505 (6)°
V = 1507.92 (13) Å³
Z = 4
Cu Kα radiation
μ = 2.24 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 = 0.554, T_max = 0.896
25955 measured reflections
6143 independent reflections
3143 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.079
wR(F²) = 0.273
S = 1.10
6140 reflections
199 parameters
18 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	2.07	2.923 (3)	162
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: https://doi.org/10.1107/S1600536811036154/xu5321sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036154/xu5321Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811036154/xu5321Isup3.cml

checkCIF report

Comment top

The compound (Scheme I) is a side product that was isolated along with 4-(4-chlorophenyl)-8-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3- carbonitrile, the expected product (Asiri et al., 2011); the proportion of the two compounds is unknown. The compound has one set of carbon-carbon double-bonds whereas the expected product has two, i.e., it has two more hydrogen atoms. Futhermore, the double-bond is now located in the methyl-substituted cyclohexene ring. The six-membered ring bearing an N atom that is fused with the cyclohexene ring. The nitrogen-bearing ring has the benzene-bearing C atom lying 0.432 (6) Å out of the plane defined by the other five atoms (r.m.s. deviation 0.011 Å); its benzene substituent is aligned at 84.7 (1) °. The cyclohexene ring adopts a half-chair conformation; an ethylene portion is disordered over two positions in a 1:1 ratio (Fig. 1). Two molecules are linked about a center-of-inversion by an N–H···O hydrogen bond to generate a dimer (Table 1).

Related literature top

For a similar compound that has two more H atoms, see: Asiri et al. (2011).

Experimental top

4-Chlorobenzaldehyde (1.4 g, 10 mmol), 2-methylcyclohexanone (1.2 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) were heated in ethanol (50 ml) for 6 h. The solid product was collected, washed with water and then recrystallized from ethanol.

One crystal was characterized as 4-(4-chlorophenyl)-8-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3- carbonitrile, the expected product (Asiri et al., 2011). The second type of crystal is not aromatic and it has two extra hydrogen atoms in the nitrogen-bearing ring (Scheme I).

Structure description top

For a similar compound that has two more H atoms, see: Asiri et al. (2011).

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 C₁₇H₁₇ClN₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

4-(4-Chlorophenyl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7- octahydroquinoline-3-carbonitrile top

Crystal data top

C₁₇H₁₇ClN₂O	F(000) = 632
M_r = 300.78	D_x = 1.325 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4615 reflections
a = 11.0699 (7) Å	θ = 4.1–74.2°
b = 7.6018 (3) Å	µ = 2.24 mm⁻¹
c = 18.2247 (9) Å	T = 100 K
β = 100.505 (6)°	Prism, colorless
V = 1507.92 (13) Å³	0.30 × 0.20 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	6143 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3143 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.020
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.6°, θ_min = 4.1°
ω scan	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −8→9
T_min = 0.554, T_max = 0.896	l = −22→22
25955 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.079	H-atom parameters constrained
wR(F²) = 0.273	w = 1/[σ²(F_o²) + (0.1311P)²] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
6140 reflections	Δρ_max = 0.68 e Å⁻³
199 parameters	Δρ_min = −0.46 e Å⁻³
18 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (12)

Crystal data top

C₁₇H₁₇ClN₂O	V = 1507.92 (13) Å³
M_r = 300.78	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.0699 (7) Å	µ = 2.24 mm⁻¹
b = 7.6018 (3) Å	T = 100 K
c = 18.2247 (9) Å	0.30 × 0.20 × 0.05 mm
β = 100.505 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	6143 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3143 reflections with I > 2σ(I)
T_min = 0.554, T_max = 0.896	R_int = 0.020
25955 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	18 restraints
wR(F²) = 0.273	H-atom parameters constrained
S = 1.10	Δρ_max = 0.68 e Å⁻³
6140 reflections	Δρ_min = −0.46 e Å⁻³
199 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.94318 (9)	0.09540 (11)	0.08219 (4)	0.0756 (3)
O1	0.5121 (3)	0.5375 (4)	0.41298 (14)	0.1111 (12)
N1	0.6012 (3)	0.2957 (3)	0.47183 (14)	0.0731 (8)
H1	0.5690	0.3234	0.5111	0.088*
N2	0.6458 (5)	0.6373 (4)	0.2684 (2)	0.1182 (15)
C1	0.6727 (3)	0.1423 (4)	0.47779 (17)	0.0667 (9)
C2	0.6849 (3)	0.0426 (4)	0.53982 (18)	0.0724 (9)
C3	0.6222 (4)	0.0736 (5)	0.6033 (2)	0.0845 (11)
H3A	0.6609	0.0020	0.6459	0.127*	0.50
H3B	0.5354	0.0410	0.5892	0.127*	0.50
H3C	0.6286	0.1983	0.6171	0.127*	0.50
H3D	0.5557	0.1589	0.5889	0.127*	0.50
H3E	0.6812	0.1198	0.6456	0.127*	0.50
H3F	0.5880	−0.0374	0.6177	0.127*	0.50
C4	0.7734 (15)	−0.1120 (17)	0.5423 (7)	0.102 (3)	0.50
H4A	0.7516	−0.2009	0.5774	0.123*	0.50
H4B	0.8573	−0.0698	0.5628	0.123*	0.50
C5	0.7757 (9)	−0.2041 (13)	0.4660 (5)	0.084 (3)	0.50
H5A	0.8353	−0.3025	0.4710	0.101*	0.50
H5B	0.6934	−0.2466	0.4420	0.101*	0.50
C6	0.8189 (4)	−0.0437 (5)	0.4237 (2)	0.1017 (15)
H6A	0.8961	0.0038	0.4531	0.122*	0.50
H6B	0.8364	−0.0839	0.3750	0.122*	0.50
H6C	0.8999	0.0116	0.4236	0.122*	0.50
H6D	0.8025	−0.1232	0.3800	0.122*	0.50
C4'	0.7531 (16)	−0.1306 (17)	0.5520 (8)	0.102 (3)	0.50
H4'A	0.6935	−0.2284	0.5498	0.123*	0.50
H4'B	0.8061	−0.1314	0.6020	0.123*	0.50
C5'	0.8316 (9)	−0.1565 (13)	0.4924 (4)	0.084 (3)	0.50
H5'A	0.9183	−0.1473	0.5179	0.101*	0.50
H5'B	0.8190	−0.2796	0.4749	0.101*	0.50
C7	0.7272 (4)	0.0954 (5)	0.4112 (2)	0.0914 (13)
H7	0.6568	0.0294	0.3813	0.110*
C8	0.7367 (3)	0.2397 (4)	0.36058 (16)	0.0606 (7)
H8	0.8027	0.3136	0.3905	0.073*
C9	0.6351 (4)	0.3604 (5)	0.3464 (2)	0.0936 (14)
H9	0.5698	0.2916	0.3134	0.112*
C10	0.5762 (4)	0.4046 (5)	0.41368 (19)	0.0866 (12)
C11	0.6450 (4)	0.5194 (4)	0.30371 (18)	0.0706 (9)
C12	0.7915 (3)	0.1957 (3)	0.29240 (15)	0.0555 (7)
C13	0.7323 (3)	0.0835 (4)	0.23823 (16)	0.0603 (7)
H13	0.6580	0.0285	0.2449	0.072*
C14	0.7794 (3)	0.0495 (4)	0.17398 (17)	0.0645 (8)
H14	0.7382	−0.0293	0.1373	0.077*
C15	0.8864 (3)	0.1311 (4)	0.16408 (16)	0.0588 (7)
C16	0.9464 (4)	0.2382 (5)	0.2169 (2)	0.0898 (12)
H16	1.0208	0.2924	0.2100	0.108*
C17	0.9001 (3)	0.2709 (5)	0.28208 (19)	0.0845 (11)
H17	0.9440	0.3456	0.3195	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1037 (7)	0.0772 (5)	0.0564 (4)	0.0074 (4)	0.0422 (4)	0.0022 (4)
O1	0.156 (3)	0.115 (2)	0.0785 (17)	0.082 (2)	0.0643 (18)	0.0375 (15)
N1	0.0919 (19)	0.0772 (17)	0.0608 (14)	0.0330 (15)	0.0417 (14)	0.0202 (13)
N2	0.222 (5)	0.0612 (18)	0.094 (2)	0.028 (2)	0.088 (3)	0.0162 (17)
C1	0.073 (2)	0.0755 (19)	0.0606 (17)	0.0233 (16)	0.0353 (15)	0.0164 (15)
C2	0.081 (2)	0.076 (2)	0.0669 (19)	0.0181 (17)	0.0324 (17)	0.0249 (16)
C3	0.116 (3)	0.082 (2)	0.0614 (19)	−0.009 (2)	0.031 (2)	0.0071 (17)
C4	0.140 (5)	0.105 (4)	0.083 (4)	0.046 (4)	0.074 (4)	0.058 (3)
C5	0.098 (6)	0.087 (5)	0.073 (5)	0.043 (4)	0.035 (4)	0.032 (4)
C6	0.137 (4)	0.097 (3)	0.089 (3)	0.064 (3)	0.066 (3)	0.042 (2)
C4'	0.140 (5)	0.105 (4)	0.083 (4)	0.046 (4)	0.074 (4)	0.058 (3)
C5'	0.098 (6)	0.087 (5)	0.073 (5)	0.043 (4)	0.035 (4)	0.032 (4)
C7	0.117 (3)	0.095 (3)	0.079 (2)	0.050 (2)	0.062 (2)	0.039 (2)
C8	0.082 (2)	0.0543 (15)	0.0518 (14)	0.0011 (15)	0.0290 (15)	0.0014 (12)
C9	0.138 (3)	0.085 (2)	0.074 (2)	0.054 (2)	0.061 (2)	0.0329 (19)
C10	0.112 (3)	0.090 (2)	0.069 (2)	0.051 (2)	0.049 (2)	0.0215 (18)
C11	0.112 (3)	0.0497 (15)	0.0594 (17)	0.0056 (17)	0.0401 (18)	−0.0032 (14)
C12	0.0720 (19)	0.0486 (14)	0.0511 (14)	0.0042 (13)	0.0253 (13)	0.0023 (11)
C13	0.0702 (18)	0.0533 (15)	0.0645 (17)	−0.0016 (14)	0.0308 (15)	0.0010 (13)
C14	0.083 (2)	0.0580 (17)	0.0565 (16)	−0.0004 (15)	0.0243 (16)	−0.0096 (13)
C15	0.0743 (19)	0.0574 (16)	0.0511 (15)	0.0018 (14)	0.0284 (14)	0.0009 (12)
C16	0.099 (3)	0.108 (3)	0.075 (2)	−0.038 (2)	0.049 (2)	−0.019 (2)
C17	0.093 (2)	0.103 (3)	0.0655 (19)	−0.038 (2)	0.0371 (19)	−0.0272 (19)

Geometric parameters (Å, º) top

Cl1—C15	1.743 (3)	C6—H6B	0.9900
O1—C10	1.234 (4)	C6—H6C	0.9900
N1—C10	1.333 (4)	C6—H6D	0.9900
N1—C1	1.403 (4)	C4'—C5'	1.523 (9)
N1—H1	0.8800	C4'—H4'A	0.9900
N2—C11	1.104 (4)	C4'—H4'B	0.9900
C1—C2	1.347 (4)	C5'—H5'A	0.9900
C1—C7	1.494 (4)	C5'—H5'B	0.9900
C2—C3	1.474 (4)	C7—C8	1.449 (4)
C2—C4'	1.513 (8)	C7—H7	1.0000
C2—C4	1.525 (8)	C8—C9	1.438 (4)
C3—H3A	0.9800	C8—C12	1.516 (3)
C3—H3B	0.9800	C8—H8	1.0000
C3—H3C	0.9800	C9—C11	1.452 (4)
C3—H3D	0.9800	C9—C10	1.527 (4)
C3—H3E	0.9800	C9—H9	1.0000
C3—H3F	0.9800	C12—C17	1.375 (4)
C4—C5	1.560 (9)	C12—C13	1.376 (4)
C4—H4A	0.9900	C13—C14	1.390 (4)
C4—H4B	0.9900	C13—H13	0.9500
C5—C6	1.564 (10)	C14—C15	1.378 (4)
C5—H5A	0.9900	C14—H14	0.9500
C5—H5B	0.9900	C15—C16	1.341 (5)
C6—C7	1.455 (4)	C16—C17	1.399 (4)
C6—C5'	1.502 (6)	C16—H16	0.9500
C6—H6A	0.9900	C17—H17	0.9500

C10—N1—C1	127.6 (2)	C2—C4'—H4'B	109.7
C10—N1—H1	116.2	C5'—C4'—H4'B	109.7
C1—N1—H1	116.2	H4'A—C4'—H4'B	108.2
C2—C1—N1	120.1 (3)	C6—C5'—C4'	122.8 (8)
C2—C1—C7	123.6 (3)	C6—C5'—H5'A	106.6
N1—C1—C7	116.2 (2)	C4'—C5'—H5'A	106.6
C1—C2—C3	125.4 (3)	C6—C5'—H5'B	106.6
C1—C2—C4'	125.7 (5)	C4'—C5'—H5'B	106.6
C3—C2—C4'	108.5 (5)	H5'A—C5'—H5'B	106.6
C1—C2—C4	115.1 (5)	C8—C7—C6	121.4 (3)
C3—C2—C4	119.5 (5)	C8—C7—C1	115.0 (3)
C2—C3—H3A	109.5	C6—C7—C1	114.8 (3)
C2—C3—H3B	109.5	C8—C7—H7	100.0
H3A—C3—H3B	109.5	C6—C7—H7	100.0
C2—C3—H3C	109.5	C1—C7—H7	100.0
H3A—C3—H3C	109.5	C9—C8—C7	116.9 (3)
H3B—C3—H3C	109.5	C9—C8—C12	114.2 (3)
C2—C3—H3D	109.5	C7—C8—C12	116.1 (2)
C2—C3—H3E	109.5	C9—C8—H8	102.1
H3D—C3—H3E	109.5	C7—C8—H8	102.1
C2—C3—H3F	109.5	C12—C8—H8	102.1
H3D—C3—H3F	109.5	C8—C9—C11	119.6 (3)
H3E—C3—H3F	109.5	C8—C9—C10	115.5 (3)
C2—C4—C5	115.8 (9)	C11—C9—C10	109.4 (3)
C2—C4—H4A	108.3	C8—C9—H9	103.3
C5—C4—H4A	108.3	C11—C9—H9	103.3
C2—C4—H4B	108.3	C10—C9—H9	103.3
C5—C4—H4B	108.3	O1—C10—N1	123.5 (3)
H4A—C4—H4B	107.4	O1—C10—C9	120.1 (3)
C6—C5—C4	98.4 (8)	N1—C10—C9	116.4 (3)
C6—C5—H5A	112.1	N2—C11—C9	175.5 (5)
C4—C5—H5A	112.1	C17—C12—C13	118.2 (3)
C6—C5—H5B	112.1	C17—C12—C8	120.7 (3)
C4—C5—H5B	112.1	C13—C12—C8	121.0 (3)
H5A—C5—H5B	109.7	C12—C13—C14	121.1 (3)
C7—C6—C5'	120.1 (5)	C12—C13—H13	119.4
C7—C6—C5	112.1 (5)	C14—C13—H13	119.4
C7—C6—H6A	109.2	C15—C14—C13	119.3 (3)
C5—C6—H6A	109.2	C15—C14—H14	120.3
C7—C6—H6B	109.2	C13—C14—H14	120.3
C5—C6—H6B	109.2	C16—C15—C14	120.3 (3)
H6A—C6—H6B	107.9	C16—C15—Cl1	120.0 (2)
C7—C6—H6C	107.3	C14—C15—Cl1	119.7 (2)
C5'—C6—H6C	107.3	C15—C16—C17	120.5 (3)
C7—C6—H6D	107.3	C15—C16—H16	119.8
C5'—C6—H6D	107.3	C17—C16—H16	119.8
H6C—C6—H6D	106.9	C12—C17—C16	120.4 (3)
C2—C4'—C5'	109.9 (9)	C12—C17—H17	119.8
C2—C4'—H4'A	109.7	C16—C17—H17	119.8
C5'—C4'—H4'A	109.7

C10—N1—C1—C2	−177.3 (4)	C6—C7—C8—C9	173.9 (4)
C10—N1—C1—C7	0.0 (6)	C1—C7—C8—C9	−40.3 (6)
N1—C1—C2—C3	4.0 (6)	C6—C7—C8—C12	34.3 (6)
C7—C1—C2—C3	−173.1 (4)	C1—C7—C8—C12	−179.9 (3)
N1—C1—C2—C4'	176.4 (10)	C7—C8—C9—C11	172.5 (4)
C7—C1—C2—C4'	−0.6 (12)	C12—C8—C9—C11	−47.2 (5)
N1—C1—C2—C4	−175.1 (8)	C7—C8—C9—C10	38.5 (6)
C7—C1—C2—C4	7.8 (10)	C12—C8—C9—C10	178.8 (3)
C1—C2—C4—C5	−35.6 (14)	C1—N1—C10—O1	−180.0 (4)
C3—C2—C4—C5	145.3 (8)	C1—N1—C10—C9	−1.9 (6)
C4'—C2—C4—C5	112 (6)	C8—C9—C10—O1	161.0 (4)
C2—C4—C5—C6	61.4 (12)	C11—C9—C10—O1	22.5 (6)
C4—C5—C6—C7	−66.5 (8)	C8—C9—C10—N1	−17.2 (6)
C4—C5—C6—C5'	45.8 (11)	C11—C9—C10—N1	−155.6 (4)
C1—C2—C4'—C5'	13.3 (18)	C9—C8—C12—C17	102.9 (4)
C3—C2—C4'—C5'	−173.2 (10)	C7—C8—C12—C17	−116.5 (4)
C4—C2—C4'—C5'	−23 (5)	C9—C8—C12—C13	−75.2 (4)
C7—C6—C5'—C4'	−1.2 (15)	C7—C8—C12—C13	65.4 (4)
C5—C6—C5'—C4'	−83.5 (18)	C17—C12—C13—C14	−1.2 (5)
C2—C4'—C5'—C6	−12.1 (19)	C8—C12—C13—C14	176.9 (3)
C5'—C6—C7—C8	160.1 (6)	C12—C13—C14—C15	−0.8 (5)
C5—C6—C7—C8	−167.6 (5)	C13—C14—C15—C16	2.0 (5)
C5'—C6—C7—C1	14.2 (8)	C13—C14—C15—Cl1	−177.7 (2)
C5—C6—C7—C1	46.6 (7)	C14—C15—C16—C17	−1.1 (6)
C2—C1—C7—C8	−162.0 (4)	Cl1—C15—C16—C17	178.6 (3)
N1—C1—C7—C8	20.8 (5)	C13—C12—C17—C16	2.1 (6)
C2—C1—C7—C6	−14.0 (6)	C8—C12—C17—C16	−176.0 (4)
N1—C1—C7—C6	168.9 (4)	C15—C16—C17—C12	−1.0 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.07	2.923 (3)	162

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇ClN₂O
M_r	300.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.0699 (7), 7.6018 (3), 18.2247 (9)
β (°)	100.505 (6)
V (Å³)	1507.92 (13)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.24
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	0.554, 0.896
No. of measured, independent and observed [I > 2σ(I)] reflections	25955, 6143, 3143
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.273, 1.10
No. of reflections	6140
No. of parameters	199
No. of restraints	18
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.46

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	0.88	2.07	2.923 (3)	162

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We 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
Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Badahdah, K. O. & Ng, S. W. (2011). Acta Cryst. E67, o2596. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS 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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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-(4-Chloro­phen­yl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7-octa­hydro­quinoline-3-carbo­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(4-Chlorophenyl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7-octahydroquinoline-3-carbonitrile