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

The six-membered N-heterocyclic ring of title compound, C(17)H(17)ClN(2)O, is fused with a methyl-substituted cyclo-hexene ring. The nitro-gen-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 cyclo-hexene ring adopts a half-chair conformation. In the crystal, two mol-ecules are linked about a center of inversion by pairs of N-H⋯O hydrogen bonds, generating dimers. An ethyl-ene 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 = 300.78

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.273

S = 1.10

6140 reflections

199 parameters

18 restraints

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.46 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/S1600536811036154/xu5321sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036154/xu5321Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036154/xu5321Isup3.cml

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

C17H17ClN2O	F(000) = 632
Mr = 300.78	Dx = 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

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

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(Fo2) + (0.1311P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
6140 reflections	Δρmax = 0.68 e Å−3
199 parameters	Δρmin = −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)

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) .