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

In the title compound, C(17)H(17)BrN(2)O, the N-containing ring adopts an envelope conformation with the C atom carrying the phenyl ring displaced by -0.531 (9) Å from the plane defined by the remaining five atoms (r.m.s. deviation = 0.0099 Å). The benzene ring is almost orthogonal to the ring to which it is attached, the C(CN)-C-C(Ph)-C(Ph) torsion angle being -101.3 (7)°. The cyclo-hexene ring is disordered over two conformations in a statistical ratio. The most prominent inter-actions in the crystal are pairs of N-H⋯O hydrogen bonds between inversion-related mol-ecules. The resulting dimers are linked into a three-dimensional architecture by C-H⋯N, C-H⋯Br and C-H⋯π inter-actions.

Related literature

For background to the cardiotonic and anti-inflammatory properties of octa­hydro­quinoline-3-carbonitrile derivatives, see: Behit & Baraka (2005 ▶); Girgis et al. (2007 ▶). For a related structure, see: Asiri et al. (2012 ▶). For additional conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H17BrN2O

M = 345.24

Monoclinic,

a = 11.1959 (10) Å

b = 7.5902 (6) Å

c = 18.3886 (12) Å

β = 100.453 (8)°

V = 1536.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.68 mm−1

T = 100 K

0.40 × 0.20 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.581, T max = 1.000

9883 measured reflections

3549 independent reflections

2296 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.173

S = 1.02

3549 reflections

199 parameters

22 restraints

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029820/hb6875sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029820/hb6875Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029820/hb6875Isup3.cml

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

C17H17BrN2O	F(000) = 704
Mr = 345.24	Dx = 1.492 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2464 reflections
a = 11.1959 (10) Å	θ = 2.3–27.5°
b = 7.5902 (6) Å	µ = 2.68 mm−1
c = 18.3886 (12) Å	T = 100 K
β = 100.453 (8)°	Plate, light-yellow
V = 1536.7 (2) Å3	0.40 × 0.20 × 0.02 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3549 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2296 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.052
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.6°
ω scan	h = −14→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −9→9
Tmin = 0.581, Tmax = 1.000	l = −22→23
9883 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0744P)2 + 2.0179P] where P = (Fo2 + 2Fc2)/3
3549 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.87 e Å−3
22 restraints	Δρmin = −0.44 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.06147 (5)	0.90018 (7)	0.92341 (3)	0.0586 (2)
O1	0.4933 (5)	0.4661 (6)	0.5872 (2)	0.0912 (16)
N1	0.4052 (4)	0.7076 (6)	0.5296 (2)	0.0576 (12)
H1n	0.4373	0.6809	0.4907	0.069*
N2	0.3645 (6)	0.3614 (6)	0.7319 (3)	0.0836 (18)
C1	0.3778 (6)	0.9254 (7)	0.3984 (3)	0.0579 (14)
H1A	0.3554	1.0180	0.3613	0.087*	0.50
H1B	0.3492	0.8112	0.3771	0.087*	0.50
H1C	0.4663	0.9223	0.4136	0.087*	0.50
H1D	0.4252	0.8163	0.4067	0.087*	0.50
H1E	0.4314	1.0231	0.3909	0.087*	0.50
H1F	0.3143	0.9120	0.3544	0.087*	0.50
C2	0.3211 (5)	0.9625 (7)	0.4635 (3)	0.0585 (14)
C3	0.2661 (15)	1.1429 (16)	0.4681 (7)	0.061 (4)	0.50
H3A	0.3222	1.2288	0.4516	0.073*	0.50
H3B	0.1900	1.1461	0.4311	0.073*	0.50
C4	0.2372 (13)	1.2098 (17)	0.5380 (6)	0.063 (3)	0.50
H4A	0.3078	1.2763	0.5647	0.075*	0.50
H4B	0.1679	1.2925	0.5268	0.075*	0.50
C5	0.2067 (11)	1.0704 (13)	0.5856 (8)	0.055 (4)	0.50
H5A	0.1212	1.0358	0.5676	0.066*	0.50
H5B	0.2114	1.1197	0.6359	0.066*	0.50
C3'	0.2305 (15)	1.1102 (18)	0.4484 (7)	0.061 (4)	0.50
H3C	0.2712	1.2160	0.4330	0.073*	0.50
H3D	0.1650	1.0762	0.4071	0.073*	0.50
C4'	0.1773 (13)	1.1532 (17)	0.5133 (7)	0.063 (3)	0.50
H4C	0.2227	1.2550	0.5382	0.075*	0.50
H4D	0.0930	1.1935	0.4952	0.075*	0.50
C5'	0.1727 (10)	1.0196 (15)	0.5692 (8)	0.055 (4)	0.50
H5C	0.1035	0.9404	0.5508	0.066*	0.50
H5D	0.1547	1.0790	0.6139	0.066*	0.50
C6	0.2820 (6)	0.9091 (8)	0.5917 (3)	0.075 (2)
H6	0.3575	0.9591	0.6222	0.090*	0.50
H6'	0.3437	0.9871	0.6221	0.090*	0.50
C7	0.3338 (5)	0.8612 (7)	0.5242 (3)	0.0543 (14)
C8	0.4298 (6)	0.5976 (8)	0.5872 (3)	0.0675 (18)
C9	0.3741 (6)	0.6431 (8)	0.6547 (3)	0.0667 (17)
H9	0.4373	0.7148	0.6872	0.080*
C10	0.2671 (5)	0.7576 (6)	0.6390 (2)	0.0457 (11)
H10	0.2039	0.6833	0.6079	0.055*
C11	0.3637 (5)	0.4810 (7)	0.6963 (2)	0.0522 (13)
C12	0.2137 (4)	0.7995 (6)	0.7068 (2)	0.0423 (11)
C13	0.1125 (6)	0.7135 (9)	0.7198 (3)	0.0698 (18)
H13	0.0740	0.6294	0.6850	0.084*
C14	0.0646 (5)	0.7472 (9)	0.7836 (3)	0.0704 (18)
H14	−0.0070	0.6887	0.7914	0.085*
C15	0.1213 (5)	0.8642 (6)	0.8342 (2)	0.0447 (11)
C16	0.2224 (5)	0.9533 (7)	0.8224 (3)	0.0507 (12)
H16	0.2602	1.0378	0.8573	0.061*
C17	0.2689 (5)	0.9188 (6)	0.7589 (3)	0.0476 (12)
H17	0.3401	0.9784	0.7511	0.057*

	U11	U22	U33	U12	U13	U23
Br1	0.0719 (4)	0.0740 (4)	0.0378 (3)	0.0033 (3)	0.0312 (3)	−0.0034 (2)
O1	0.134 (4)	0.098 (3)	0.057 (2)	0.072 (3)	0.058 (3)	0.033 (2)
N1	0.072 (3)	0.068 (3)	0.044 (2)	0.031 (2)	0.041 (2)	0.020 (2)
N2	0.153 (6)	0.055 (3)	0.057 (3)	0.021 (3)	0.057 (3)	0.010 (2)
C1	0.076 (4)	0.061 (3)	0.043 (3)	−0.003 (3)	0.028 (3)	0.007 (2)
C2	0.066 (4)	0.068 (3)	0.050 (3)	0.016 (3)	0.035 (3)	0.022 (3)
C3	0.072 (8)	0.073 (5)	0.041 (6)	0.023 (5)	0.020 (5)	0.018 (4)
C4	0.069 (7)	0.066 (6)	0.061 (6)	0.030 (5)	0.032 (5)	0.021 (4)
C5	0.071 (6)	0.052 (6)	0.051 (6)	0.017 (5)	0.032 (5)	0.006 (5)
C3'	0.072 (8)	0.073 (5)	0.041 (6)	0.023 (5)	0.020 (5)	0.018 (4)
C4'	0.069 (7)	0.066 (6)	0.061 (6)	0.030 (5)	0.032 (5)	0.021 (4)
C5'	0.071 (6)	0.052 (6)	0.051 (6)	0.017 (5)	0.032 (5)	0.006 (5)
C6	0.090 (5)	0.090 (4)	0.062 (3)	0.047 (4)	0.058 (3)	0.040 (3)
C7	0.060 (3)	0.067 (3)	0.045 (3)	0.024 (3)	0.035 (2)	0.017 (2)
C8	0.085 (4)	0.077 (4)	0.051 (3)	0.042 (3)	0.041 (3)	0.019 (3)
C9	0.096 (5)	0.066 (3)	0.050 (3)	0.028 (3)	0.043 (3)	0.017 (3)
C10	0.064 (3)	0.044 (3)	0.034 (2)	0.004 (2)	0.023 (2)	0.000 (2)
C11	0.090 (4)	0.044 (3)	0.031 (2)	0.009 (3)	0.032 (2)	0.000 (2)
C12	0.057 (3)	0.043 (2)	0.032 (2)	−0.001 (2)	0.021 (2)	0.0019 (19)
C13	0.079 (4)	0.096 (4)	0.043 (3)	−0.039 (4)	0.034 (3)	−0.027 (3)
C14	0.070 (4)	0.100 (5)	0.049 (3)	−0.039 (3)	0.032 (3)	−0.020 (3)
C15	0.048 (3)	0.056 (3)	0.035 (2)	0.002 (2)	0.022 (2)	−0.002 (2)
C16	0.058 (3)	0.053 (3)	0.046 (3)	−0.001 (2)	0.024 (2)	−0.011 (2)
C17	0.059 (3)	0.041 (2)	0.051 (3)	−0.004 (2)	0.032 (2)	−0.003 (2)

Br1—C15	1.900 (4)	C3'—H3D	0.9900
O1—C8	1.225 (6)	C4'—C5'	1.451 (10)
N1—C8	1.336 (6)	C4'—H4C	0.9900
N1—C7	1.407 (6)	C4'—H4D	0.9900
N1—H1n	0.8800	C5'—C6	1.480 (9)
N2—C11	1.118 (6)	C5'—H5C	0.9900
C1—C2	1.481 (7)	C5'—H5D	0.9900
C1—H1A	0.9800	C6—C10	1.469 (7)
C1—H1B	0.9800	C6—C7	1.507 (7)
C1—H1C	0.9800	C6—H6	1.0000
C1—H1D	0.9800	C6—H6'	1.0000
C1—H1E	0.9800	C8—C9	1.527 (7)
C1—H1F	0.9800	C9—C11	1.465 (7)
C2—C7	1.342 (7)	C9—C10	1.465 (7)
C2—C3'	1.503 (9)	C9—H9	1.0000
C2—C3	1.510 (9)	C10—C12	1.511 (6)
C3—C4	1.471 (10)	C10—H10	1.0000
C3—H3A	0.9900	C12—C13	1.366 (7)
C3—H3B	0.9900	C12—C17	1.380 (7)
C4—C5	1.454 (10)	C13—C14	1.398 (7)
C4—H4A	0.9900	C13—H13	0.9500
C4—H4B	0.9900	C14—C15	1.358 (7)
C5—C6	1.479 (9)	C14—H14	0.9500
C5—H5A	0.9900	C15—C16	1.369 (7)
C5—H5B	0.9900	C16—C17	1.387 (6)
C3'—C4'	1.464 (10)	C16—H16	0.9500
C3'—H3C	0.9900	C17—H17	0.9500
C8—N1—C7	127.3 (4)	H4C—C4'—H4D	107.0
C8—N1—H1n	116.3	C4'—C5'—C6	117.4 (10)
C7—N1—H1n	116.3	C4'—C5'—H5C	107.9
C2—C1—H1A	109.5	C6—C5'—H5C	107.9
C2—C1—H1B	109.5	C4'—C5'—H5D	107.9
H1A—C1—H1B	109.5	C6—C5'—H5D	107.9
C2—C1—H1C	109.5	H5C—C5'—H5D	107.2
H1A—C1—H1C	109.5	C10—C6—C5'	115.6 (7)
H1B—C1—H1C	109.5	C10—C6—C5	124.6 (6)
C2—C1—H1D	109.5	C5'—C6—C5	22.9 (9)
H1A—C1—H1D	141.1	C10—C6—C7	113.7 (5)
H1B—C1—H1D	56.3	C5'—C6—C7	109.2 (7)
H1C—C1—H1D	56.3	C5—C6—C7	115.9 (6)
C2—C1—H1E	109.5	C10—C6—H6	98.1
H1A—C1—H1E	56.3	C5'—C6—H6	120.9
H1B—C1—H1E	141.1	C5—C6—H6	98.1
H1C—C1—H1E	56.3	C7—C6—H6	98.1
H1D—C1—H1E	109.5	C10—C6—H6'	105.9
C2—C1—H1F	109.5	C5'—C6—H6'	105.9
H1A—C1—H1F	56.3	C7—C6—H6'	105.9
H1B—C1—H1F	56.3	C2—C7—N1	120.4 (4)
H1C—C1—H1F	141.1	C2—C7—C6	123.3 (5)
H1D—C1—H1F	109.5	N1—C7—C6	116.1 (4)
H1E—C1—H1F	109.5	O1—C8—N1	123.1 (5)
C7—C2—C1	124.6 (5)	O1—C8—C9	120.4 (5)
C7—C2—C3'	123.2 (7)	N1—C8—C9	116.6 (4)
C1—C2—C3'	111.5 (6)	C11—C9—C10	117.5 (5)
C7—C2—C3	117.1 (6)	C11—C9—C8	108.5 (4)
C1—C2—C3	117.2 (6)	C10—C9—C8	114.4 (4)
C4—C3—C2	121.3 (10)	C11—C9—H9	105.0
C4—C3—H3A	107.0	C10—C9—H9	105.0
C2—C3—H3A	107.0	C8—C9—H9	105.0
C4—C3—H3B	107.0	C9—C10—C6	113.8 (5)
C2—C3—H3B	107.0	C9—C10—C12	113.2 (4)
H3A—C3—H3B	106.7	C6—C10—C12	115.4 (4)
C5—C4—C3	112.8 (13)	C9—C10—H10	104.3
C5—C4—H4A	109.0	C6—C10—H10	104.3
C3—C4—H4A	109.0	C12—C10—H10	104.3
C5—C4—H4B	109.0	N2—C11—C9	174.1 (7)
C3—C4—H4B	109.0	C13—C12—C17	118.3 (4)
H4A—C4—H4B	107.8	C13—C12—C10	120.6 (4)
C4—C5—C6	117.1 (10)	C17—C12—C10	121.1 (4)
C4—C5—H5A	108.0	C12—C13—C14	121.0 (5)
C6—C5—H5A	108.0	C12—C13—H13	119.5
C4—C5—H5B	108.0	C14—C13—H13	119.5
C6—C5—H5B	108.0	C15—C14—C13	119.5 (5)
H5A—C5—H5B	107.3	C15—C14—H14	120.3
C4'—C3'—C2	112.1 (9)	C13—C14—H14	120.3
C4'—C3'—H3C	109.2	C14—C15—C16	120.7 (4)
C2—C3'—H3C	109.2	C14—C15—Br1	119.4 (4)
C4'—C3'—H3D	109.2	C16—C15—Br1	119.8 (4)
C2—C3'—H3D	109.2	C15—C16—C17	119.2 (5)
H3C—C3'—H3D	107.9	C15—C16—H16	120.4
C5'—C4'—C3'	119.5 (12)	C17—C16—H16	120.4
C5'—C4'—H4C	107.4	C12—C17—C16	121.3 (5)
C3'—C4'—H4C	107.4	C12—C17—H17	119.4
C5'—C4'—H4D	107.4	C16—C17—H17	119.4
C3'—C4'—H4D	107.4
C7—C2—C3—C4	4.8 (19)	C7—N1—C8—O1	−179.9 (7)
C1—C2—C3—C4	−163.6 (12)	C7—N1—C8—C9	0.2 (10)
C3'—C2—C3—C4	117 (4)	O1—C8—C9—C11	−24.4 (9)
C2—C3—C4—C5	−30 (2)	N1—C8—C9—C11	155.5 (6)
C3—C4—C5—C6	42.1 (18)	O1—C8—C9—C10	−157.8 (7)
C7—C2—C3'—C4'	11.8 (19)	N1—C8—C9—C10	22.1 (9)
C1—C2—C3'—C4'	−177.7 (11)	C11—C9—C10—C6	−175.0 (5)
C3—C2—C3'—C4'	−67 (2)	C8—C9—C10—C6	−46.0 (8)
C2—C3'—C4'—C5'	−25 (2)	C11—C9—C10—C12	50.7 (7)
C3'—C4'—C5'—C6	43 (2)	C8—C9—C10—C12	179.7 (5)
C4'—C5'—C6—C10	−170.4 (10)	C5'—C6—C10—C9	174.9 (8)
C4'—C5'—C6—C5	71 (2)	C5—C6—C10—C9	−160.7 (9)
C4'—C5'—C6—C7	−40.8 (15)	C7—C6—C10—C9	47.5 (8)
C4—C5—C6—C10	177.9 (10)	C5'—C6—C10—C12	−51.8 (10)
C4—C5—C6—C5'	−109 (3)	C5—C6—C10—C12	−27.4 (12)
C4—C5—C6—C7	−30.9 (16)	C7—C6—C10—C12	−179.2 (5)
C1—C2—C7—N1	0.2 (10)	C9—C10—C12—C13	−101.3 (7)
C3'—C2—C7—N1	169.4 (10)	C6—C10—C12—C13	125.1 (6)
C3—C2—C7—N1	−167.4 (9)	C9—C10—C12—C17	75.4 (6)
C1—C2—C7—C6	175.6 (6)	C6—C10—C12—C17	−58.2 (7)
C3'—C2—C7—C6	−15.1 (13)	C17—C12—C13—C14	1.1 (9)
C3—C2—C7—C6	8.1 (12)	C10—C12—C13—C14	177.9 (6)
C8—N1—C7—C2	177.4 (6)	C12—C13—C14—C15	−1.6 (10)
C8—N1—C7—C6	1.7 (9)	C13—C14—C15—C16	2.0 (9)
C10—C6—C7—C2	158.9 (6)	C13—C14—C15—Br1	−176.5 (5)
C5'—C6—C7—C2	28.2 (11)	C14—C15—C16—C17	−2.0 (8)
C5—C6—C7—C2	4.5 (12)	Br1—C15—C16—C17	176.6 (4)
C10—C6—C7—N1	−25.4 (8)	C13—C12—C17—C16	−1.0 (8)
C5'—C6—C7—N1	−156.1 (7)	C10—C12—C17—C16	−177.8 (4)
C5—C6—C7—N1	−179.8 (8)	C15—C16—C17—C12	1.4 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1i	0.88	2.08	2.921 (5)	161
C1—H1A···N2ii	0.98	2.57	3.442 (8)	148
C13—H13···Br1iii	0.95	2.86	3.811 (6)	174
C1—H1B···Cg1iv	0.98	2.78	3.590 (6)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1i	0.88	2.08	2.921 (5)	161
C1—H1A⋯N2ii	0.98	2.57	3.442 (8)	148
C13—H13⋯Br1iii	0.95	2.86	3.811 (6)	174
C1—H1B⋯Cg1iv	0.98	2.78	3.590 (6)	141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .