2-Chloro-12-phenyl-6,7,8,9,10,11-hexa-hydro-cyclo-octa-[b]quinoline.

In the mol-ecule of the title compound, C(21)H(20)ClN, the quinoline group is nearly planar and is oriented at a dihedral angle of 77.21 (3)° with respect to the phenyl ring. The conformation of the cyclooctane ring is twist-boat. In the crystal structure, there are some weak π-π inter-actions [centroid-to-centroid distances of 3.7414 (11) and 3.8633 (12) Å] between the rings of the quinoline groups.

Related literature

For general background, see: Kalluraya & Sreenivasa (1998 ▶); Doube et al. (1998 ▶); Maguire et al. (1994 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H20ClN

M = 321.83

Triclinic,

a = 9.837 (2) Å

b = 9.980 (2) Å

c = 10.175 (2) Å

α = 74.600 (17)°

β = 70.575 (16)°

γ = 61.829 (15)°

V = 823.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 298 (2) K

0.5 × 0.5 × 0.25 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: numerical; shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2002 ▶) T min = 0.889, T max = 0.949

8123 measured reflections

3801 independent reflections

3493 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.126

S = 1.03

3801 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009239/hk2449sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009239/hk2449Isup2.hkl

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

C21H20Cl1N1	Z = 2
Mr = 321.83	F000 = 340
Triclinic, P1	Dx = 1.298 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.837 (2) Å	Cell parameters from 2086 reflections
b = 9.980 (2) Å	θ = 2.4–28.0º
c = 10.175 (2) Å	µ = 0.23 mm−1
α = 74.600 (17)º	T = 298 (2) K
β = 70.575 (16)º	Block, colorless
γ = 61.829 (15)º	0.5 × 0.5 × 0.25 mm
V = 823.4 (3) Å3

Stoe IPDSII diffractometer	Rint = 0.045
rotation method scans	θmax = 28.0º
Absorption correction: numericalshape of crystal determined optically [PROGRAM NAME? reference?	θmin = 2.4º
Tmin = 0.889, Tmax = 0.949	h = −12→11
8123 measured reflections	k = −13→10
3801 independent reflections	l = −13→13
3493 reflections with I > 2σ(I)

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.1883P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.046	(Δ/σ)max = 0.006
wR(F2) = 0.126	Δρmax = 0.25 e Å−3
S = 1.04	Δρmin = −0.19 e Å−3
3801 reflections	Extinction correction: none
208 parameters

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.

	x	y	z	Uiso*/Ueq
Cl1	0.59962 (5)	0.96565 (4)	0.17975 (4)	0.06276 (16)
N1	0.51106 (12)	0.54812 (13)	0.69575 (11)	0.0391 (2)
C1	0.53821 (13)	0.64045 (14)	0.57445 (12)	0.0354 (2)
C2	0.42557 (15)	0.79582 (15)	0.56208 (15)	0.0440 (3)
H2	0.3377	0.8313	0.6366	0.053*
C3	0.44417 (16)	0.89348 (15)	0.44312 (16)	0.0462 (3)
H3	0.3693	0.9949	0.4354	0.055*
C4	0.57823 (15)	0.83909 (14)	0.33177 (14)	0.0418 (3)
C5	0.69071 (14)	0.69125 (14)	0.33901 (13)	0.0392 (3)
H5	0.7787	0.659	0.2639	0.047*
C6	0.67271 (13)	0.58733 (13)	0.46148 (12)	0.0333 (2)
C7	0.78256 (13)	0.43037 (13)	0.47776 (12)	0.0339 (2)
C8	0.75403 (14)	0.33702 (14)	0.60027 (12)	0.0357 (2)
C9	0.86347 (17)	0.16885 (15)	0.62161 (14)	0.0456 (3)
H9A	0.9111	0.1313	0.531	0.055*
H9B	0.8003	0.1139	0.6796	0.055*
C10	0.99695 (16)	0.13077 (18)	0.69016 (16)	0.0542 (4)
H10A	1.0455	0.0207	0.7167	0.065*
H10B	1.0777	0.1584	0.62	0.065*
C11	0.94953 (18)	0.2078 (2)	0.81886 (16)	0.0549 (4)
H11A	0.9085	0.3178	0.7909	0.066*
H11B	1.0445	0.1765	0.8501	0.066*
C12	0.82614 (19)	0.17430 (19)	0.94328 (16)	0.0553 (4)
H12A	0.8568	0.1606	1.0289	0.066*
H12B	0.8289	0.078	0.936	0.066*
C13	0.65535 (18)	0.29655 (18)	0.95684 (14)	0.0510 (3)
H13A	0.6551	0.3948	0.9529	0.061*
H13B	0.5927	0.2748	1.0491	0.061*
C14	0.57222 (16)	0.31198 (17)	0.84728 (14)	0.0470 (3)
H14A	0.5988	0.2101	0.8307	0.056*
H14B	0.4582	0.3605	0.8855	0.056*
C15	0.61401 (13)	0.40276 (14)	0.70838 (12)	0.0370 (3)
C16	0.92569 (13)	0.37293 (13)	0.35925 (12)	0.0359 (2)
C17	0.91195 (17)	0.34403 (19)	0.23968 (14)	0.0498 (3)
H17	0.8139	0.3575	0.2335	0.06*
C18	1.0449 (2)	0.2949 (2)	0.12879 (17)	0.0655 (5)
H18	1.0355	0.2746	0.0489	0.079*
C19	1.1906 (2)	0.2758 (2)	0.13600 (18)	0.0631 (4)
H19	1.2792	0.2421	0.0617	0.076*
C20	1.20421 (17)	0.30678 (19)	0.25315 (18)	0.0564 (4)
H20	1.302	0.2955	0.2578	0.068*
C21	1.07270 (15)	0.35483 (16)	0.36480 (15)	0.0453 (3)
H21	1.083	0.3752	0.4442	0.054*

	U11	U22	U33	U12	U13	U23
Cl1	0.0600 (3)	0.0434 (2)	0.0641 (3)	−0.01716 (17)	−0.01096 (18)	0.01044 (16)
N1	0.0288 (5)	0.0426 (5)	0.0396 (5)	−0.0107 (4)	−0.0059 (4)	−0.0076 (4)
C1	0.0271 (5)	0.0369 (6)	0.0400 (6)	−0.0093 (4)	−0.0084 (4)	−0.0094 (4)
C2	0.0304 (6)	0.0392 (6)	0.0524 (7)	−0.0063 (5)	−0.0053 (5)	−0.0130 (5)
C3	0.0367 (6)	0.0334 (6)	0.0607 (8)	−0.0071 (5)	−0.0131 (6)	−0.0078 (5)
C4	0.0396 (6)	0.0357 (6)	0.0486 (7)	−0.0157 (5)	−0.0132 (5)	−0.0006 (5)
C5	0.0327 (6)	0.0376 (6)	0.0426 (6)	−0.0123 (5)	−0.0068 (5)	−0.0059 (5)
C6	0.0268 (5)	0.0346 (5)	0.0377 (5)	−0.0102 (4)	−0.0084 (4)	−0.0083 (4)
C7	0.0277 (5)	0.0358 (6)	0.0366 (5)	−0.0095 (4)	−0.0080 (4)	−0.0096 (4)
C8	0.0318 (5)	0.0346 (6)	0.0391 (6)	−0.0103 (4)	−0.0104 (4)	−0.0074 (4)
C9	0.0475 (7)	0.0333 (6)	0.0455 (7)	−0.0086 (5)	−0.0103 (5)	−0.0065 (5)
C10	0.0372 (7)	0.0478 (7)	0.0542 (8)	−0.0030 (6)	−0.0116 (6)	0.0008 (6)
C11	0.0457 (7)	0.0622 (9)	0.0552 (8)	−0.0218 (7)	−0.0207 (6)	0.0034 (7)
C12	0.0548 (8)	0.0573 (9)	0.0470 (7)	−0.0206 (7)	−0.0186 (6)	0.0057 (6)
C13	0.0531 (8)	0.0526 (8)	0.0366 (6)	−0.0188 (6)	−0.0069 (5)	−0.0013 (5)
C14	0.0372 (6)	0.0509 (7)	0.0463 (7)	−0.0197 (6)	−0.0053 (5)	−0.0001 (6)
C15	0.0301 (5)	0.0413 (6)	0.0387 (6)	−0.0142 (5)	−0.0091 (4)	−0.0050 (5)
C16	0.0308 (5)	0.0325 (5)	0.0378 (6)	−0.0083 (4)	−0.0052 (4)	−0.0085 (4)
C17	0.0420 (7)	0.0655 (9)	0.0450 (7)	−0.0231 (6)	−0.0054 (5)	−0.0178 (6)
C18	0.0635 (10)	0.0914 (13)	0.0468 (8)	−0.0362 (9)	0.0029 (7)	−0.0309 (8)
C19	0.0472 (8)	0.0739 (11)	0.0574 (9)	−0.0243 (8)	0.0123 (7)	−0.0265 (8)
C20	0.0323 (6)	0.0617 (9)	0.0695 (9)	−0.0167 (6)	−0.0022 (6)	−0.0190 (7)
C21	0.0348 (6)	0.0471 (7)	0.0513 (7)	−0.0118 (5)	−0.0087 (5)	−0.0152 (6)

C1—N1	1.3612 (16)	C11—H11A	0.97
C1—C6	1.4153 (16)	C11—H11B	0.97
C1—C2	1.4194 (17)	C12—C13	1.526 (2)
C2—C3	1.358 (2)	C12—H12A	0.97
C2—H2	0.93	C12—H12B	0.97
C3—C4	1.4051 (19)	C13—C14	1.527 (2)
C3—H3	0.93	C13—H13A	0.97
C4—C5	1.3644 (18)	C13—H13B	0.97
C4—Cl1	1.7405 (14)	C14—C15	1.5075 (18)
C5—C6	1.4143 (17)	C14—H14A	0.97
C5—H5	0.93	C14—H14B	0.97
C6—C7	1.4255 (16)	C15—N1	1.3217 (17)
C7—C8	1.3777 (17)	C16—C17	1.3836 (18)
C7—C16	1.4969 (16)	C16—C21	1.3890 (18)
C8—C15	1.4353 (17)	C17—C18	1.390 (2)
C8—C9	1.5096 (17)	C17—H17	0.93
C9—C10	1.534 (2)	C18—C19	1.378 (3)
C9—H9A	0.97	C18—H18	0.93
C9—H9B	0.97	C19—C20	1.370 (2)
C10—C11	1.521 (2)	C19—H19	0.93
C10—H10A	0.97	C20—C21	1.3857 (19)
C10—H10B	0.97	C20—H20	0.93
C11—C12	1.524 (2)	C21—H21	0.93
N1—C1—C6	122.66 (11)	H11A—C11—H11B	107.4
N1—C1—C2	117.98 (11)	C11—C12—C13	115.65 (13)
C6—C1—C2	119.36 (11)	C11—C12—H12A	108.4
C3—C2—C1	121.00 (12)	C13—C12—H12A	108.4
C3—C2—H2	119.5	C11—C12—H12B	108.4
C1—C2—H2	119.5	C13—C12—H12B	108.4
C2—C3—C4	119.00 (12)	H12A—C12—H12B	107.4
C2—C3—H3	120.5	C12—C13—C14	116.62 (13)
C4—C3—H3	120.5	C12—C13—H13A	108.1
C5—C4—C3	122.25 (12)	C14—C13—H13A	108.1
C5—C4—Cl1	119.37 (10)	C12—C13—H13B	108.1
C3—C4—Cl1	118.37 (10)	C14—C13—H13B	108.1
C4—C5—C6	119.61 (11)	H13A—C13—H13B	107.3
C4—C5—H5	120.2	C15—C14—C13	114.79 (11)
C6—C5—H5	120.2	C15—C14—H14A	108.6
C5—C6—C1	118.77 (11)	C13—C14—H14A	108.6
C5—C6—C7	123.61 (10)	C15—C14—H14B	108.6
C1—C6—C7	117.63 (11)	C13—C14—H14B	108.6
C8—C7—C6	119.53 (10)	H14A—C14—H14B	107.5
C8—C7—C16	122.32 (10)	N1—C15—C8	123.17 (11)
C6—C7—C16	118.15 (10)	N1—C15—C14	114.02 (11)
C7—C8—C15	118.28 (11)	C8—C15—C14	122.80 (11)
C7—C8—C9	121.86 (11)	C17—C16—C21	118.98 (11)
C15—C8—C9	119.85 (11)	C17—C16—C7	120.43 (11)
C8—C9—C10	115.07 (12)	C21—C16—C7	120.52 (11)
C8—C9—H9A	108.5	C16—C17—C18	119.87 (13)
C10—C9—H9A	108.5	C16—C17—H17	120.1
C8—C9—H9B	108.5	C18—C17—H17	120.1
C10—C9—H9B	108.5	C19—C18—C17	120.65 (15)
H9A—C9—H9B	107.5	C19—C18—H18	119.7
C11—C10—C9	116.56 (12)	C17—C18—H18	119.7
C11—C10—H10A	108.2	C20—C19—C18	119.70 (13)
C9—C10—H10A	108.2	C20—C19—H19	120.2
C11—C10—H10B	108.2	C18—C19—H19	120.1
C9—C10—H10B	108.2	C19—C20—C21	120.16 (14)
H10A—C10—H10B	107.3	C19—C20—H20	119.9
C10—C11—C12	116.04 (14)	C21—C20—H20	119.9
C10—C11—H11A	108.3	C20—C21—C16	120.63 (13)
C12—C11—H11A	108.3	C20—C21—H21	119.7
C10—C11—H11B	108.3	C16—C21—H21	119.7
C12—C11—H11B	108.3	C15—N1—C1	118.73 (10)
N1—C1—C2—C3	−178.99 (12)	C10—C11—C12—C13	−98.63 (17)
C6—C1—C2—C3	0.70 (19)	C11—C12—C13—C14	70.55 (19)
C1—C2—C3—C4	−0.6 (2)	C12—C13—C14—C15	−80.42 (17)
C2—C3—C4—C5	0.0 (2)	C7—C8—C15—N1	0.29 (18)
C2—C3—C4—Cl1	179.69 (11)	C9—C8—C15—N1	−178.45 (11)
C3—C4—C5—C6	0.7 (2)	C7—C8—C15—C14	−179.14 (11)
Cl1—C4—C5—C6	−179.07 (9)	C9—C8—C15—C14	2.13 (18)
C4—C5—C6—C1	−0.59 (18)	C13—C14—C15—N1	−96.60 (14)
C4—C5—C6—C7	178.98 (11)	C13—C14—C15—C8	82.88 (16)
N1—C1—C6—C5	179.60 (10)	C8—C7—C16—C17	103.88 (15)
C2—C1—C6—C5	−0.07 (17)	C6—C7—C16—C17	−75.90 (16)
N1—C1—C6—C7	0.00 (17)	C8—C7—C16—C21	−79.21 (16)
C2—C1—C6—C7	−179.67 (11)	C6—C7—C16—C21	101.02 (14)
C5—C6—C7—C8	−179.10 (11)	C21—C16—C17—C18	1.2 (2)
C1—C6—C7—C8	0.48 (16)	C7—C16—C17—C18	178.19 (15)
C5—C6—C7—C16	0.69 (17)	C16—C17—C18—C19	−0.6 (3)
C1—C6—C7—C16	−179.74 (10)	C17—C18—C19—C20	−0.5 (3)
C6—C7—C8—C15	−0.62 (17)	C18—C19—C20—C21	1.0 (3)
C16—C7—C8—C15	179.61 (10)	C19—C20—C21—C16	−0.3 (2)
C6—C7—C8—C9	178.09 (11)	C17—C16—C21—C20	−0.8 (2)
C16—C7—C8—C9	−1.68 (18)	C7—C16—C21—C20	−177.74 (13)
C7—C8—C9—C10	91.27 (15)	C8—C15—N1—C1	0.19 (18)
C15—C8—C9—C10	−90.04 (15)	C14—C15—N1—C1	179.66 (10)
C8—C9—C10—C11	46.24 (18)	C6—C1—N1—C15	−0.33 (18)
C9—C10—C11—C12	59.62 (18)	C2—C1—N1—C15	179.34 (11)