Bis(1,2,3,4-tetra-hydro-quinolin-6-yl)methane.

The asymmetric unit of the title compound, C(19)H(22)N(2), contains one half-mol-ecule. The 1,2,3,4-tetra-hydro-quinoline units are linked by a methyl-ene bridge, which lies on a twofold rotation axis. The non-aromatic ring adopts a flattened-boat conformation. The dihedral angle between the two symmetry-related benzene rings is 64.03 (7)°.

Related literature

For general background, see: Xiao et al. (2008a ▶,b ▶,c ▶); Xiao et al. (2007a ▶,b ▶); Xue et al. (2007 ▶). For ring conformation puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H22N2

M = 278.39

Orthorhombic,

a = 17.515 (3) Å

b = 29.660 (4) Å

c = 5.7678 (8) Å

V = 2996.2 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 292 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.979, T max = 0.986

4545 measured reflections

814 independent reflections

773 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.138

S = 1.07

814 reflections

100 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025464/hk2506sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025464/hk2506Isup2.hkl

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

C19H22N2	F000 = 1200
Mr = 278.39	Dx = 1.234 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 1297 reflections
a = 17.515 (3) Å	θ = 2.9–25.2º
b = 29.660 (4) Å	µ = 0.07 mm−1
c = 5.7678 (8) Å	T = 292 (2) K
V = 2996.2 (8) Å3	Prism, colorless
Z = 8	0.30 × 0.20 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	814 independent reflections
Radiation source: fine-focus sealed tube	773 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.073
T = 292(2) K	θmax = 26.0º
ω/2θ scans	θmin = 2.7º
Absorption correction: ψ scan(North et al., 1968)	h = −21→21
Tmin = 0.979, Tmax = 0.986	k = −36→32
4545 measured reflections	l = −7→6

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0996P)2 + 0.9957P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
814 reflections	Δρmax = 0.28 e Å−3
100 parameters	Δρmin = −0.21 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N1	0.26094 (12)	0.44383 (8)	1.0848 (5)	0.0605 (7)
H11A	0.2700	0.4566	1.2159	0.073*
C1	0.0000	0.5000	0.5624 (6)	0.0519 (9)
H1	0.0128 (16)	0.5254 (7)	0.464 (5)	0.067 (10)*
C2	0.31123 (16)	0.40914 (9)	1.0048 (7)	0.0637 (9)
H2A	0.3360	0.3951	1.1368	0.076*
H2B	0.3505	0.4224	0.9080	0.076*
C3	0.27005 (17)	0.37452 (10)	0.8715 (8)	0.0662 (9)
H3A	0.2357	0.3584	0.9740	0.079*
H3B	0.3064	0.3530	0.8094	0.079*
C4	0.22470 (16)	0.39493 (9)	0.6743 (6)	0.0579 (8)
H4A	0.2595	0.4045	0.5530	0.070*
H4B	0.1911	0.3722	0.6097	0.070*
C5	0.11375 (13)	0.44942 (7)	0.6314 (5)	0.0415 (6)
H5	0.1004	0.4345	0.4954	0.050*
C6	0.06877 (12)	0.48523 (8)	0.7038 (5)	0.0407 (6)
C7	0.09023 (12)	0.50718 (8)	0.9058 (5)	0.0434 (6)
H7	0.0615	0.5315	0.9581	0.052*
C8	0.15365 (13)	0.49360 (8)	1.0313 (5)	0.0435 (6)
H8	0.1667	0.5088	1.1667	0.052*
C9	0.19817 (12)	0.45735 (7)	0.9568 (5)	0.0384 (5)
C10	0.17797 (12)	0.43464 (7)	0.7524 (5)	0.0390 (6)

	U11	U22	U33	U12	U13	U23
N1	0.0578 (13)	0.0610 (13)	0.0628 (17)	0.0115 (10)	−0.0273 (12)	−0.0153 (13)
C1	0.0451 (19)	0.068 (2)	0.042 (2)	0.0156 (17)	0.000	0.000
C2	0.0537 (15)	0.0635 (16)	0.074 (2)	0.0170 (11)	−0.0201 (16)	0.0025 (16)
C3	0.0623 (16)	0.0582 (15)	0.078 (2)	0.0198 (12)	−0.0097 (17)	−0.0042 (16)
C4	0.0622 (16)	0.0558 (14)	0.0558 (18)	0.0202 (12)	−0.0111 (15)	−0.0126 (14)
C5	0.0420 (12)	0.0442 (11)	0.0384 (13)	0.0016 (9)	−0.0014 (11)	−0.0069 (10)
C6	0.0324 (10)	0.0460 (10)	0.0437 (13)	0.0024 (8)	0.0016 (10)	0.0000 (11)
C7	0.0383 (11)	0.0416 (11)	0.0504 (15)	0.0045 (9)	0.0061 (10)	−0.0052 (11)
C8	0.0440 (12)	0.0432 (11)	0.0433 (14)	−0.0040 (9)	−0.0018 (11)	−0.0113 (11)
C9	0.0345 (11)	0.0392 (10)	0.0416 (13)	−0.0032 (8)	−0.0034 (10)	0.0013 (10)
C10	0.0398 (11)	0.0375 (10)	0.0398 (12)	0.0008 (8)	−0.0007 (10)	−0.0036 (11)

N1—C2	1.431 (3)	C4—H4B	0.9700
N1—H11A	0.8600	C5—C6	1.387 (3)
C1—C6	1.519 (3)	C5—C10	1.394 (3)
C1—C6i	1.519 (3)	C5—H5	0.9300
C1—H1	0.97 (2)	C7—C6	1.386 (4)
C2—C3	1.472 (4)	C7—H7	0.9300
C2—H2A	0.9700	C8—C7	1.386 (3)
C2—H2B	0.9700	C8—H8	0.9300
C3—H3A	0.9700	C9—N1	1.384 (3)
C3—H3B	0.9700	C9—C8	1.396 (3)
C4—C3	1.514 (4)	C9—C10	1.403 (4)
C4—H4A	0.9700	C10—C4	1.503 (3)
C9—N1—C2	121.7 (3)	C10—C4—H4B	109.2
C9—N1—H11A	119.2	C3—C4—H4B	109.2
C2—N1—H11A	119.2	H4A—C4—H4B	107.9
C6—C1—C6i	115.1 (3)	C6—C5—C10	123.3 (2)
C6—C1—H1	110.8 (18)	C6—C5—H5	118.4
C6i—C1—H1	105.9 (19)	C10—C5—H5	118.4
N1—C2—C3	111.6 (2)	C7—C6—C5	117.3 (2)
N1—C2—H2A	109.3	C7—C6—C1	122.0 (2)
C3—C2—H2A	109.3	C5—C6—C1	120.6 (2)
N1—C2—H2B	109.3	C8—C7—C6	121.3 (2)
C3—C2—H2B	109.3	C8—C7—H7	119.3
H2A—C2—H2B	108.0	C6—C7—H7	119.3
C2—C3—C4	111.8 (2)	C7—C8—C9	120.7 (2)
C2—C3—H3A	109.3	C7—C8—H8	119.6
C4—C3—H3A	109.3	C9—C8—H8	119.6
C2—C3—H3B	109.3	N1—C9—C8	120.2 (2)
C4—C3—H3B	109.3	N1—C9—C10	120.6 (2)
H3A—C3—H3B	107.9	C8—C9—C10	119.2 (2)
C10—C4—C3	112.0 (2)	C5—C10—C9	118.2 (2)
C10—C4—H4A	109.2	C5—C10—C4	122.4 (2)
C3—C4—H4A	109.2	C9—C10—C4	119.4 (2)
C9—N1—C2—C3	−33.5 (4)	C9—C8—C7—C6	0.3 (4)
C6i—C1—C6—C7	−39.05 (19)	C8—C9—N1—C2	−175.1 (2)
C6i—C1—C6—C5	142.3 (3)	C10—C9—N1—C2	5.6 (4)
N1—C2—C3—C4	54.2 (4)	N1—C9—C8—C7	−179.4 (2)
C10—C4—C3—C2	−48.1 (4)	C10—C9—C8—C7	0.0 (4)
C10—C5—C6—C7	0.6 (4)	N1—C9—C10—C5	179.4 (2)
C10—C5—C6—C1	179.3 (2)	C8—C9—C10—C5	0.0 (3)
C6—C5—C10—C9	−0.3 (4)	N1—C9—C10—C4	0.7 (4)
C6—C5—C10—C4	178.3 (2)	C8—C9—C10—C4	−178.6 (2)
C8—C7—C6—C5	−0.6 (4)	C5—C10—C4—C3	−157.7 (2)
C8—C7—C6—C1	−179.2 (2)	C9—C10—C4—C3	20.9 (4)