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

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

doi:10.1107/S1600536811036142

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2596

https://doi.org/10.1107/S1600536811036142

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4-(4-Chlorophenyl)-8-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-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 ^*

^bChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, ^aCenter 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 the title compound, C₁₇H₁₅ClN₂O, is fused with a methyl-substituted cyclohexene ring. The approximately planar nitrogen-bearing ring (r.m.s. deviation 0.019 Å) is aromatic, and the N atom shows a trigonal–planar coordination; its benzene substituent is aligned at 77.1 (1) °. The cyclohexene ring adopts a half-chair conformation. In the crystal, inversion-related molecules are linked by pairs of N—H⋯O hydrogen bonds, generating dimers.

Related literature

For a related compound, see: Asiri et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₅ClN₂O
M_r = 298.76
Monoclinic, C 2/c
a = 18.6304 (4) Å
b = 18.7399 (4) Å
c = 8.5209 (2) Å
β = 90.229 (2)°
V = 2974.89 (11) Å³
Z = 8
Cu Kα radiation
μ = 2.27 mm⁻¹
T = 100 K
0.30 × 0.03 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.550, T_max = 0.935
10387 measured reflections
3014 independent reflections
2682 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.187
S = 1.03
3014 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.91 (4)	1.84 (4)	2.744 (3)	174 (4)
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/S1600536811036142/xu5320sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036142/xu5320Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811036142/xu5320Isup3.cml

checkCIF report

Comment top

We have reported the synthesis of 2-oxo-4-phenyl-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile by using the reaction of benzaldehyde, 1-tetralone and ethyl cyanoacetate. The last reactant is incorporated into the product to form a part of the six-membered nitrogen-bearing ring, which is now endowed with an exocyclic cyanide group (Asiri et al., 2011). In the present study, the use of 2-methylcyclohexane leads to the formation of the analogous compound with a cyclohexene ring fused with the six-membered nitrogen-bearing ring (Scheme I). The planar nitrogen-bearing ring (r.m.s. deviation 0.019 Å) is aromatic, and the N atom shows trigonal planar coordination; its benzene substituent is aligned at 77.1 (1) °. The cyclohexene ring adopts a half-chair conformation (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 related compound, 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.

Structure description top

For a related compound, 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 C₁₇H₁₅ClN₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₁₇H₁₅ClN₂O	F(000) = 1248
M_r = 298.76	D_x = 1.334 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 4602 reflections
a = 18.6304 (4) Å	θ = 3.3–74.1°
b = 18.7399 (4) Å	µ = 2.27 mm⁻¹
c = 8.5209 (2) Å	T = 100 K
β = 90.229 (2)°	Prism, colorless
V = 2974.89 (11) Å³	0.30 × 0.03 × 0.03 mm
Z = 8

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3014 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2682 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.025
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.3°, θ_min = 3.4°
ω scan	h = −22→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→23
T_min = 0.550, T_max = 0.935	l = −10→10
10387 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.187	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0973P)² + 6.1309P] where P = (F_o² + 2F_c²)/3
3014 reflections	(Δ/σ)_max = 0.001
194 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₇H₁₅ClN₂O	V = 2974.89 (11) Å³
M_r = 298.76	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 18.6304 (4) Å	µ = 2.27 mm⁻¹
b = 18.7399 (4) Å	T = 100 K
c = 8.5209 (2) Å	0.30 × 0.03 × 0.03 mm
β = 90.229 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3014 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2682 reflections with I > 2σ(I)
T_min = 0.550, T_max = 0.935	R_int = 0.025
10387 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.187	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.79 e Å⁻³
3014 reflections	Δρ_min = −0.40 e Å⁻³
194 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.03066 (4)	0.40727 (4)	1.04897 (10)	0.0561 (3)
O1	0.43887 (13)	0.55097 (12)	0.6145 (3)	0.0732 (8)
N1	0.43862 (13)	0.43226 (13)	0.5593 (3)	0.0513 (6)
N2	0.28356 (14)	0.58993 (14)	0.8353 (3)	0.0520 (6)
C1	0.41066 (14)	0.36551 (15)	0.5654 (4)	0.0448 (6)
C2	0.44737 (15)	0.31216 (15)	0.4544 (4)	0.0458 (6)
H2	0.4536	0.3360	0.3503	0.055*
C3	0.52222 (16)	0.29166 (17)	0.5165 (4)	0.0531 (7)
H3A	0.5514	0.3348	0.5291	0.080*
H3B	0.5455	0.2594	0.4418	0.080*
H3C	0.5175	0.2677	0.6182	0.080*
C4	0.39803 (15)	0.24814 (15)	0.4311 (3)	0.0461 (6)
H4A	0.4254	0.2088	0.3818	0.055*
H4B	0.3584	0.2615	0.3590	0.055*
C5	0.36656 (18)	0.22215 (15)	0.5866 (3)	0.0498 (7)
H5A	0.4062	0.2102	0.6598	0.060*
H5B	0.3382	0.1783	0.5679	0.060*
C6	0.31816 (16)	0.27916 (15)	0.6619 (4)	0.0480 (7)
H6A	0.2711	0.2795	0.6074	0.058*
H6B	0.3097	0.2664	0.7731	0.058*
C7	0.35036 (15)	0.35264 (14)	0.6542 (3)	0.0425 (6)
C8	0.31531 (15)	0.41183 (14)	0.7254 (3)	0.0402 (6)
C9	0.34494 (15)	0.47924 (15)	0.7151 (3)	0.0453 (6)
C10	0.41041 (17)	0.49152 (16)	0.6296 (4)	0.0532 (7)
C11	0.31115 (15)	0.54044 (16)	0.7834 (3)	0.0451 (6)
C12	0.24447 (15)	0.40529 (14)	0.8035 (3)	0.0396 (6)
C13	0.23840 (17)	0.38018 (16)	0.9559 (3)	0.0480 (7)
H13	0.2797	0.3628	1.0093	0.058*
C14	0.17279 (18)	0.38018 (16)	1.0307 (3)	0.0512 (7)
H14	0.1688	0.3630	1.1352	0.061*
C15	0.11297 (16)	0.40541 (14)	0.9520 (3)	0.0436 (6)
C16	0.11705 (16)	0.43002 (17)	0.8006 (4)	0.0504 (7)
H16	0.0753	0.4465	0.7474	0.060*
C17	0.18293 (16)	0.43036 (18)	0.7268 (3)	0.0502 (7)
H17	0.1865	0.4479	0.6225	0.060*
H1	0.481 (2)	0.439 (2)	0.508 (5)	0.078 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0605 (5)	0.0437 (4)	0.0642 (5)	−0.0013 (3)	0.0181 (4)	0.0010 (3)
O1	0.0666 (14)	0.0474 (13)	0.106 (2)	−0.0271 (11)	0.0384 (14)	−0.0337 (13)
N1	0.0412 (13)	0.0416 (13)	0.0711 (17)	−0.0104 (10)	0.0060 (12)	−0.0181 (12)
N2	0.0544 (14)	0.0540 (15)	0.0478 (13)	−0.0066 (11)	0.0023 (11)	−0.0180 (11)
C1	0.0362 (13)	0.0401 (14)	0.0580 (16)	−0.0042 (11)	−0.0058 (11)	−0.0078 (12)
C2	0.0416 (14)	0.0358 (13)	0.0599 (17)	−0.0031 (11)	0.0022 (12)	0.0042 (12)
C3	0.0464 (16)	0.0499 (17)	0.0631 (18)	−0.0040 (13)	0.0025 (13)	0.0048 (14)
C4	0.0467 (14)	0.0404 (14)	0.0510 (16)	−0.0046 (12)	0.0032 (12)	−0.0013 (12)
C5	0.0692 (19)	0.0329 (13)	0.0472 (15)	−0.0062 (12)	0.0010 (13)	0.0046 (11)
C6	0.0484 (15)	0.0383 (14)	0.0573 (16)	−0.0057 (11)	−0.0037 (12)	0.0050 (12)
C7	0.0445 (14)	0.0358 (13)	0.0472 (14)	−0.0024 (11)	−0.0113 (11)	−0.0001 (11)
C8	0.0444 (14)	0.0418 (14)	0.0342 (12)	−0.0054 (11)	−0.0083 (10)	−0.0001 (10)
C9	0.0460 (14)	0.0415 (14)	0.0484 (15)	−0.0097 (11)	0.0036 (11)	−0.0107 (11)
C10	0.0494 (15)	0.0440 (16)	0.0662 (19)	−0.0134 (12)	0.0103 (14)	−0.0193 (14)
C11	0.0469 (14)	0.0465 (15)	0.0420 (13)	−0.0132 (12)	0.0047 (11)	−0.0088 (12)
C12	0.0454 (14)	0.0373 (13)	0.0361 (12)	−0.0066 (10)	−0.0032 (10)	−0.0020 (10)
C13	0.0568 (16)	0.0489 (16)	0.0383 (14)	0.0081 (13)	−0.0004 (12)	0.0069 (12)
C14	0.0665 (18)	0.0461 (16)	0.0411 (14)	0.0045 (14)	0.0054 (13)	0.0093 (12)
C15	0.0534 (16)	0.0318 (13)	0.0457 (14)	−0.0067 (11)	0.0066 (12)	−0.0018 (10)
C16	0.0467 (15)	0.0563 (17)	0.0480 (15)	−0.0107 (13)	−0.0080 (12)	0.0046 (13)
C17	0.0463 (15)	0.0670 (19)	0.0374 (13)	−0.0133 (14)	−0.0068 (11)	0.0082 (13)

Geometric parameters (Å, º) top

Cl1—C15	1.745 (3)	C5—H5B	0.9900
O1—C10	1.241 (4)	C6—C7	1.503 (4)
N1—C1	1.356 (4)	C6—H6A	0.9900
N1—C10	1.368 (4)	C6—H6B	0.9900
N1—H1	0.91 (4)	C7—C8	1.424 (4)
N2—C11	1.150 (4)	C8—C9	1.382 (4)
C1—C7	1.378 (4)	C8—C12	1.486 (4)
C1—C2	1.539 (4)	C9—C11	1.433 (4)
C2—C4	1.524 (4)	C9—C10	1.442 (4)
C2—C3	1.538 (4)	C12—C13	1.386 (4)
C2—H2	1.0000	C12—C17	1.399 (4)
C3—H3A	0.9800	C13—C14	1.381 (4)
C3—H3B	0.9800	C13—H13	0.9500
C3—H3C	0.9800	C14—C15	1.382 (4)
C4—C5	1.531 (4)	C14—H14	0.9500
C4—H4A	0.9900	C15—C16	1.373 (4)
C4—H4B	0.9900	C16—C17	1.381 (4)
C5—C6	1.540 (4)	C16—H16	0.9500
C5—H5A	0.9900	C17—H17	0.9500

C1—N1—C10	125.7 (3)	C5—C6—H6B	109.1
C1—N1—H1	118 (3)	H6A—C6—H6B	107.8
C10—N1—H1	116 (3)	C1—C7—C8	118.3 (2)
N1—C1—C7	119.8 (3)	C1—C7—C6	120.7 (3)
N1—C1—C2	113.8 (2)	C8—C7—C6	120.7 (3)
C7—C1—C2	126.1 (2)	C9—C8—C7	120.1 (3)
C4—C2—C1	108.8 (2)	C9—C8—C12	117.4 (2)
C4—C2—C3	113.2 (2)	C7—C8—C12	122.4 (2)
C1—C2—C3	110.8 (2)	C8—C9—C11	122.0 (3)
C4—C2—H2	108.0	C8—C9—C10	121.1 (3)
C1—C2—H2	108.0	C11—C9—C10	116.8 (2)
C3—C2—H2	108.0	O1—C10—N1	121.2 (3)
C2—C3—H3A	109.5	O1—C10—C9	124.0 (3)
C2—C3—H3B	109.5	N1—C10—C9	114.8 (2)
H3A—C3—H3B	109.5	N2—C11—C9	178.6 (3)
C2—C3—H3C	109.5	C13—C12—C17	118.8 (3)
H3A—C3—H3C	109.5	C13—C12—C8	121.6 (2)
H3B—C3—H3C	109.5	C17—C12—C8	119.4 (2)
C2—C4—C5	111.7 (2)	C14—C13—C12	120.5 (3)
C2—C4—H4A	109.3	C14—C13—H13	119.7
C5—C4—H4A	109.3	C12—C13—H13	119.7
C2—C4—H4B	109.3	C13—C14—C15	119.3 (3)
C5—C4—H4B	109.3	C13—C14—H14	120.3
H4A—C4—H4B	107.9	C15—C14—H14	120.3
C4—C5—C6	111.5 (2)	C16—C15—C14	121.6 (3)
C4—C5—H5A	109.3	C16—C15—Cl1	119.4 (2)
C6—C5—H5A	109.3	C14—C15—Cl1	119.0 (2)
C4—C5—H5B	109.3	C15—C16—C17	118.8 (3)
C6—C5—H5B	109.3	C15—C16—H16	120.6
H5A—C5—H5B	108.0	C17—C16—H16	120.6
C7—C6—C5	112.5 (2)	C16—C17—C12	120.9 (3)
C7—C6—H6A	109.1	C16—C17—H17	119.5
C5—C6—H6A	109.1	C12—C17—H17	119.5
C7—C6—H6B	109.1

C10—N1—C1—C7	−3.1 (5)	C7—C8—C9—C10	1.6 (4)
C10—N1—C1—C2	171.0 (3)	C12—C8—C9—C10	−174.6 (3)
N1—C1—C2—C4	−161.8 (3)	C1—N1—C10—O1	−178.3 (3)
C7—C1—C2—C4	11.8 (4)	C1—N1—C10—C9	−0.6 (5)
N1—C1—C2—C3	73.2 (3)	C8—C9—C10—O1	178.9 (3)
C7—C1—C2—C3	−113.2 (3)	C11—C9—C10—O1	1.0 (5)
C1—C2—C4—C5	−45.4 (3)	C8—C9—C10—N1	1.3 (4)
C3—C2—C4—C5	78.3 (3)	C11—C9—C10—N1	−176.6 (3)
C2—C4—C5—C6	63.7 (3)	C9—C8—C12—C13	−102.5 (3)
C4—C5—C6—C7	−43.5 (3)	C7—C8—C12—C13	81.5 (3)
N1—C1—C7—C8	5.8 (4)	C9—C8—C12—C17	72.3 (3)
C2—C1—C7—C8	−167.5 (3)	C7—C8—C12—C17	−103.8 (3)
N1—C1—C7—C6	179.6 (3)	C17—C12—C13—C14	−0.2 (4)
C2—C1—C7—C6	6.3 (4)	C8—C12—C13—C14	174.5 (3)
C5—C6—C7—C1	9.8 (4)	C12—C13—C14—C15	0.1 (5)
C5—C6—C7—C8	−176.5 (2)	C13—C14—C15—C16	0.5 (4)
C1—C7—C8—C9	−5.1 (4)	C13—C14—C15—Cl1	−178.4 (2)
C6—C7—C8—C9	−178.9 (3)	C14—C15—C16—C17	−1.0 (4)
C1—C7—C8—C12	170.9 (2)	Cl1—C15—C16—C17	178.0 (2)
C6—C7—C8—C12	−2.9 (4)	C15—C16—C17—C12	0.8 (5)
C7—C8—C9—C11	179.3 (3)	C13—C12—C17—C16	−0.2 (4)
C12—C8—C9—C11	3.1 (4)	C8—C12—C17—C16	−175.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.91 (4)	1.84 (4)	2.744 (3)	174 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅ClN₂O
M_r	298.76
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	18.6304 (4), 18.7399 (4), 8.5209 (2)
β (°)	90.229 (2)
V (Å³)	2974.89 (11)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.27
Crystal size (mm)	0.30 × 0.03 × 0.03

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.550, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	10387, 3014, 2682
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.187, 1.03
No. of reflections	3014
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.40

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	0.91 (4)	1.84 (4)	2.744 (3)	174 (4)

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, England. Google Scholar
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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2596

https://doi.org/10.1107/S1600536811036142

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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-1,2,5,6,7,8-hexa­hydro­quinoline-3-carbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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