2-Oxo-4-(thio-phen-2-yl)-1,2,5,6-tetra-hydro-benzo[h]quinoline-3-carbonitrile.

In the mol-ecule of the title compound, C(18)H(12)N(2)OS, the tetra-hydro-benzo[h]quinoline fused-ring system is buckled owing to the ethyl-ene -CH(2)CH(2)- fragment, the benzene ring and the pyridine ring being twisted by 16.0 (1)°. The 4-substituted aromatic ring is bent away from the pyridine ring by 59.5 (2)° (for the major disordered thienyl component) in order to avoid crowding the cyanide substituent. In the crystal, two mol-ecules are linked by a pair of N-H⋯O hydrogen bonds to form a centrosymmetric dimer. The thienyl ring is disordered over two sites in a 72.7 (2):27.3 ratio.

Related literature

For background to the anti­cancer properties of this class of compounds, see: Rostom et al. (2011 ▶) .

Experimental

Crystal data

C18H12N2OS

M = 304.36

Triclinic,

a = 6.9952 (3) Å

b = 9.1809 (4) Å

c = 11.1837 (5) Å

α = 93.990 (4)°

β = 95.293 (4)°

γ = 100.903 (4)°

V = 699.48 (5) Å3

Z = 2

Cu Kα radiation

μ = 2.07 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.575, T max = 0.682

5795 measured reflections

2740 independent reflections

2600 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.07

2740 reflections

216 parameters

19 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.45 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/S1600536811033915/xu5294sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033915/xu5294Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033915/xu5294Isup3.cml

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

C18H12N2OS	Z = 2
Mr = 304.36	F(000) = 316
Triclinic, P1	Dx = 1.445 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.9952 (3) Å	Cell parameters from 4426 reflections
b = 9.1809 (4) Å	θ = 4.0–74.1°
c = 11.1837 (5) Å	µ = 2.07 mm−1
α = 93.990 (4)°	T = 100 K
β = 95.293 (4)°	Prism, yellow
γ = 100.903 (4)°	0.30 × 0.25 × 0.20 mm
V = 699.48 (5) Å3

Agilent SuperNova Dual diffractometer with Atlas detector	2740 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2600 reflections with I > 2σ(I)
mirror	Rint = 0.020
Detector resolution: 10.4041 pixels mm-1	θmax = 74.3°, θmin = 4.0°
ω scans	h = −7→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→10
Tmin = 0.575, Tmax = 0.682	l = −13→13
5795 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.2491P] where P = (Fo2 + 2Fc2)/3
2740 reflections	(Δ/σ)max = 0.001
216 parameters	Δρmax = 0.22 e Å−3
19 restraints	Δρmin = −0.45 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	1.02806 (12)	0.99939 (9)	0.19100 (9)	0.0171 (2)	0.727 (2)
C1	1.2328 (6)	1.0301 (6)	0.1115 (5)	0.0157 (7)	0.727 (2)
H1A	1.2578	1.1055	0.0578	0.019*	0.727 (2)
C2	1.3559 (7)	0.9300 (6)	0.1367 (5)	0.0163 (7)	0.727 (2)
H2	1.4748	0.9289	0.1022	0.020*	0.727 (2)
C3	1.2770 (14)	0.8250 (17)	0.2247 (12)	0.0299 (8)	0.727 (2)
H3	1.3373	0.7474	0.2526	0.036*	0.727 (2)
S1'	1.3139 (8)	0.8217 (10)	0.2250 (7)	0.0299 (8)	0.27
C1'	1.0531 (18)	0.9773 (13)	0.1982 (12)	0.0171 (2)	0.27
H1'	0.9394	1.0180	0.2067	0.021*	0.273 (2)
C2'	1.196 (2)	1.025 (2)	0.1248 (15)	0.0157 (7)	0.27
H2'	1.1922	1.1045	0.0750	0.019*	0.273 (2)
C3'	1.330 (2)	0.9528 (19)	0.1306 (17)	0.0163 (7)	0.27
H3'	1.4357	0.9723	0.0829	0.020*	0.273 (2)
O1	0.50080 (13)	0.56034 (11)	0.36325 (8)	0.0192 (2)
N1	0.76813 (15)	0.61659 (12)	0.50268 (10)	0.0153 (2)
H1	0.692 (2)	0.5628 (18)	0.5492 (14)	0.027 (4)*
N2	0.64560 (17)	0.68980 (14)	0.08687 (10)	0.0219 (3)
C4	1.10455 (19)	0.85666 (15)	0.25948 (11)	0.0162 (3)
C5	0.71303 (18)	0.69445 (15)	0.18506 (12)	0.0168 (3)
C6	0.67568 (18)	0.62164 (15)	0.38930 (12)	0.0159 (3)
C7	0.79651 (18)	0.70041 (15)	0.30795 (12)	0.0159 (3)
C8	0.98753 (19)	0.77471 (15)	0.34578 (12)	0.0160 (3)
C9	1.06717 (19)	0.77150 (15)	0.46658 (12)	0.0162 (3)
C10	1.26416 (19)	0.86240 (16)	0.52013 (12)	0.0198 (3)
H10A	1.2453	0.9555	0.5636	0.024*
H10B	1.3466	0.8896	0.4547	0.024*
C11	1.36693 (19)	0.77390 (16)	0.60685 (12)	0.0182 (3)
H11A	1.4051	0.6897	0.5610	0.022*
H11B	1.4876	0.8387	0.6482	0.022*
C12	1.23569 (19)	0.71478 (14)	0.69931 (12)	0.0164 (3)
C13	1.3114 (2)	0.69892 (15)	0.81603 (12)	0.0203 (3)
H13	1.4490	0.7224	0.8373	0.024*
C14	1.1894 (2)	0.64951 (16)	0.90172 (12)	0.0217 (3)
H14	1.2435	0.6397	0.9811	0.026*
C15	0.9873 (2)	0.61428 (15)	0.87154 (12)	0.0202 (3)
H15	0.9033	0.5831	0.9309	0.024*
C16	0.90914 (19)	0.62486 (15)	0.75477 (12)	0.0181 (3)
H16	0.7716	0.5983	0.7337	0.022*
C17	1.03169 (19)	0.67444 (14)	0.66757 (11)	0.0153 (3)
C18	0.95516 (18)	0.68759 (14)	0.54271 (11)	0.0153 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0179 (4)	0.0139 (4)	0.0219 (3)	0.0049 (2)	0.0047 (2)	0.0097 (2)
C1	0.0132 (19)	0.0185 (8)	0.0149 (14)	−0.0033 (14)	0.0089 (11)	0.0063 (9)
C2	0.0145 (16)	0.0178 (19)	0.0197 (9)	0.0090 (9)	0.0038 (11)	0.0044 (11)
C3	0.029 (2)	0.0331 (6)	0.0259 (4)	−0.0033 (16)	0.0123 (14)	0.0043 (4)
S1'	0.029 (2)	0.0331 (6)	0.0259 (4)	−0.0033 (16)	0.0123 (14)	0.0043 (4)
C1'	0.0179 (4)	0.0139 (4)	0.0219 (3)	0.0049 (2)	0.0047 (2)	0.0097 (2)
C2'	0.0132 (19)	0.0185 (8)	0.0149 (14)	−0.0033 (14)	0.0089 (11)	0.0063 (9)
C3'	0.0145 (16)	0.0178 (19)	0.0197 (9)	0.0090 (9)	0.0038 (11)	0.0044 (11)
O1	0.0129 (4)	0.0267 (5)	0.0170 (5)	0.0003 (4)	0.0007 (3)	0.0071 (4)
N1	0.0134 (5)	0.0190 (6)	0.0137 (5)	0.0012 (4)	0.0029 (4)	0.0054 (4)
N2	0.0192 (6)	0.0287 (7)	0.0182 (6)	0.0045 (5)	0.0013 (5)	0.0070 (5)
C4	0.0159 (6)	0.0181 (7)	0.0138 (6)	0.0011 (5)	0.0005 (5)	0.0050 (5)
C5	0.0132 (6)	0.0189 (7)	0.0192 (7)	0.0030 (5)	0.0043 (5)	0.0055 (5)
C6	0.0141 (6)	0.0182 (6)	0.0160 (6)	0.0040 (5)	0.0015 (5)	0.0033 (5)
C7	0.0148 (6)	0.0191 (7)	0.0147 (6)	0.0043 (5)	0.0026 (5)	0.0052 (5)
C8	0.0159 (6)	0.0174 (6)	0.0163 (6)	0.0049 (5)	0.0038 (5)	0.0044 (5)
C9	0.0147 (6)	0.0177 (6)	0.0158 (6)	0.0015 (5)	0.0022 (5)	0.0036 (5)
C10	0.0176 (6)	0.0222 (7)	0.0169 (6)	−0.0030 (5)	0.0010 (5)	0.0041 (5)
C11	0.0139 (6)	0.0220 (7)	0.0168 (6)	−0.0006 (5)	0.0004 (5)	0.0023 (5)
C12	0.0177 (6)	0.0149 (6)	0.0157 (6)	0.0015 (5)	0.0007 (5)	0.0009 (5)
C13	0.0190 (7)	0.0206 (7)	0.0186 (7)	−0.0007 (5)	−0.0024 (5)	0.0020 (5)
C14	0.0268 (7)	0.0212 (7)	0.0148 (6)	0.0005 (6)	−0.0030 (5)	0.0035 (5)
C15	0.0242 (7)	0.0201 (7)	0.0152 (6)	−0.0001 (5)	0.0037 (5)	0.0037 (5)
C16	0.0172 (6)	0.0191 (7)	0.0170 (6)	0.0009 (5)	0.0018 (5)	0.0028 (5)
C17	0.0175 (6)	0.0144 (6)	0.0138 (6)	0.0026 (5)	0.0015 (5)	0.0015 (5)
C18	0.0148 (6)	0.0163 (6)	0.0151 (6)	0.0036 (5)	0.0020 (5)	0.0020 (5)

S1—C4	1.7085 (14)	C6—C7	1.4378 (18)
S1—C1	1.743 (3)	C7—C8	1.3930 (18)
C1—C2	1.398 (6)	C8—C9	1.4175 (18)
C1—H1A	0.9500	C9—C18	1.3850 (18)
C2—C3	1.495 (15)	C9—C10	1.5156 (18)
C2—H2	0.9500	C10—C11	1.5230 (19)
C3—C4	1.377 (10)	C10—H10A	0.9900
C3—H3	0.9500	C10—H10B	0.9900
S1'—C4	1.631 (6)	C11—C12	1.5071 (17)
S1'—C3'	1.651 (19)	C11—H11A	0.9900
C1'—C2'	1.377 (18)	C11—H11B	0.9900
C1'—C4	1.427 (11)	C12—C13	1.3904 (18)
C1'—H1'	0.9500	C12—C17	1.4099 (18)
C2'—C3'	1.25 (2)	C13—C14	1.385 (2)
C2'—H2'	0.9500	C13—H13	0.9500
C3'—H3'	0.9500	C14—C15	1.393 (2)
O1—C6	1.2447 (16)	C14—H14	0.9500
N1—C18	1.3659 (17)	C15—C16	1.3856 (19)
N1—C6	1.3771 (16)	C15—H15	0.9500
N1—H1	0.885 (9)	C16—C17	1.4005 (18)
N2—C5	1.1491 (18)	C16—H16	0.9500
C4—C8	1.4770 (17)	C17—C18	1.4701 (17)
C5—C7	1.4361 (18)
C4—S1—C1	92.12 (19)	C7—C8—C4	119.51 (12)
C2—C1—S1	111.6 (4)	C9—C8—C4	120.73 (12)
C2—C1—H1A	124.2	C18—C9—C8	118.65 (12)
S1—C1—H1A	124.2	C18—C9—C10	117.54 (12)
C1—C2—C3	111.6 (6)	C8—C9—C10	123.70 (12)
C1—C2—H2	124.2	C9—C10—C11	110.44 (11)
C3—C2—H2	124.2	C9—C10—H10A	109.6
C4—C3—C2	110.3 (10)	C11—C10—H10A	109.6
C4—C3—H3	124.9	C9—C10—H10B	109.6
C2—C3—H3	124.9	C11—C10—H10B	109.6
C4—S1'—C3'	90.2 (6)	H10A—C10—H10B	108.1
C2'—C1'—C4	108.7 (11)	C12—C11—C10	111.07 (11)
C2'—C1'—H1'	125.6	C12—C11—H11A	109.4
C4—C1'—H1'	125.6	C10—C11—H11A	109.4
C3'—C2'—C1'	112.7 (15)	C12—C11—H11B	109.4
C3'—C2'—H2'	123.6	C10—C11—H11B	109.4
C1'—C2'—H2'	123.6	H11A—C11—H11B	108.0
C2'—C3'—S1'	116.8 (14)	C13—C12—C17	118.92 (12)
C2'—C3'—H3'	121.6	C13—C12—C11	121.40 (12)
S1'—C3'—H3'	121.6	C17—C12—C11	119.69 (11)
C18—N1—C6	125.02 (11)	C14—C13—C12	121.08 (13)
C18—N1—H1	122.2 (12)	C14—C13—H13	119.5
C6—N1—H1	112.8 (12)	C12—C13—H13	119.5
C3—C4—C1'	110.3 (8)	C13—C14—C15	120.03 (13)
C3—C4—C8	124.6 (6)	C13—C14—H14	120.0
C1'—C4—C8	125.0 (5)	C15—C14—H14	120.0
C1'—C4—S1'	111.5 (6)	C16—C15—C14	119.84 (12)
C8—C4—S1'	123.5 (3)	C16—C15—H15	120.1
C3—C4—S1	114.4 (6)	C14—C15—H15	120.1
C8—C4—S1	120.97 (10)	C15—C16—C17	120.41 (12)
S1'—C4—S1	115.5 (3)	C15—C16—H16	119.8
N2—C5—C7	179.74 (15)	C17—C16—H16	119.8
O1—C6—N1	120.39 (11)	C16—C17—C12	119.65 (12)
O1—C6—C7	124.73 (12)	C16—C17—C18	122.26 (12)
N1—C6—C7	114.88 (11)	C12—C17—C18	118.08 (11)
C8—C7—C5	121.69 (11)	N1—C18—C9	119.93 (12)
C8—C7—C6	121.52 (12)	N1—C18—C17	118.58 (11)
C5—C7—C6	116.76 (11)	C9—C18—C17	121.49 (12)
C7—C8—C9	119.75 (12)
C4—S1—C1—C2	0.8 (4)	S1—C4—C8—C7	59.63 (16)
S1—C1—C2—C3	0.0 (8)	C3—C4—C8—C9	61.7 (7)
C1—C2—C3—C4	−1.1 (11)	C1'—C4—C8—C9	−119.9 (7)
C4—C1'—C2'—C3'	0(2)	S1'—C4—C8—C9	58.6 (4)
C1'—C2'—C3'—S1'	−2(2)	S1—C4—C8—C9	−120.06 (13)
C4—S1'—C3'—C2'	2.4 (17)	C7—C8—C9—C18	3.23 (19)
C2—C3—C4—C1'	1.5 (11)	C4—C8—C9—C18	−177.08 (12)
C2—C3—C4—C8	−179.9 (5)	C7—C8—C9—C10	−172.91 (12)
C2—C3—C4—S1'	−113 (20)	C4—C8—C9—C10	6.8 (2)
C2—C3—C4—S1	1.7 (10)	C18—C9—C10—C11	40.78 (16)
C2'—C1'—C4—C3	−0.9 (14)	C8—C9—C10—C11	−143.04 (13)
C2'—C1'—C4—C8	−179.6 (9)	C9—C10—C11—C12	−52.44 (15)
C2'—C1'—C4—S1'	1.8 (13)	C10—C11—C12—C13	−147.28 (13)
C2'—C1'—C4—S1	−177 (9)	C10—C11—C12—C17	32.72 (17)
C3'—S1'—C4—C3	64 (19)	C17—C12—C13—C14	−2.3 (2)
C3'—S1'—C4—C1'	−2.3 (10)	C11—C12—C13—C14	177.69 (13)
C3'—S1'—C4—C8	179.1 (7)	C12—C13—C14—C15	0.2 (2)
C3'—S1'—C4—S1	−2.2 (8)	C13—C14—C15—C16	1.8 (2)
C1—S1—C4—C3	−1.5 (6)	C14—C15—C16—C17	−1.6 (2)
C1—S1—C4—C1'	2(8)	C15—C16—C17—C12	−0.5 (2)
C1—S1—C4—C8	−180.0 (2)	C15—C16—C17—C18	−179.92 (12)
C1—S1—C4—S1'	1.3 (4)	C13—C12—C17—C16	2.4 (2)
C18—N1—C6—O1	−175.77 (12)	C11—C12—C17—C16	−177.59 (12)
C18—N1—C6—C7	4.57 (19)	C13—C12—C17—C18	−178.11 (12)
O1—C6—C7—C8	175.70 (13)	C11—C12—C17—C18	1.90 (18)
N1—C6—C7—C8	−4.65 (19)	C6—N1—C18—C9	−0.6 (2)
O1—C6—C7—C5	−6.4 (2)	C6—N1—C18—C17	178.47 (11)
N1—C6—C7—C5	173.28 (11)	C8—C9—C18—N1	−3.49 (19)
C5—C7—C8—C9	−176.88 (12)	C10—C9—C18—N1	172.89 (12)
C6—C7—C8—C9	0.9 (2)	C8—C9—C18—C17	177.49 (11)
C5—C7—C8—C4	3.42 (19)	C10—C9—C18—C17	−6.14 (19)
C6—C7—C8—C4	−178.75 (12)	C16—C17—C18—N1	−16.20 (19)
C3—C4—C8—C7	−118.6 (7)	C12—C17—C18—N1	164.33 (12)
C1'—C4—C8—C7	59.8 (7)	C16—C17—C18—C9	162.84 (13)
S1'—C4—C8—C7	−121.7 (4)	C12—C17—C18—C9	−16.63 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.89 (1)	1.97 (1)	2.851 (1)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.89 (1)	1.97 (1)	2.851 (1)	173 (2)

Symmetry code: (i) .