4-(4-Chloro-phen-yl)-8-methyl-2-oxo-1,2,5,6,7,8-hexa-hydro-quinoline-3-carbonitrile.

The six-membered N-heterocyclic ring of the title compound, C(17)H(15)ClN(2)O, is fused with a methyl-substituted cyclo-hexene ring. The approximately planar nitro-gen-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 cyclo-hexene ring adopts a half-chair conformation. In the crystal, inversion-related mol-ecules 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 = 298.76

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.187

S = 1.03

3014 reflections

194 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.79 e Å−3

Δρmin = −0.40 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036142/xu5320sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036142/xu5320Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036142/xu5320Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H15ClN2O	F(000) = 1248
Mr = 298.76	Dx = 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

Agilent SuperNova Dual diffractometer with Atlas detector	3014 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2682 reflections with I > 2σ(I)
Mirror	Rint = 0.025
Detector resolution: 10.4041 pixels mm-1	θmax = 74.3°, θmin = 3.4°
ω scan	h = −22→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→23
Tmin = 0.550, Tmax = 0.935	l = −10→10
10387 measured reflections

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(Fo2) + (0.0973P)2 + 6.1309P] where P = (Fo2 + 2Fc2)/3
3014 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) .