(S)-N-Benzyl-2-methyl-1,2,3,4-tetra-hydro-isoquinoline-3-carboxamide.

The structure of the title compound, C(18)H(20)N(2)O, at 173 K has hexa-gonal (P6(1)) symmetry. The N-containing six-membered ring assumes a half-chair conformation. In the crystal, inter-molecular N-H⋯O hydrogen bonding via the amide groups cross-link the mol-ecules along the a axis. The absolute configuration was confirmed by 2D NMR studies.

Related literature

The title compound is a precursor to chiral ligands involving a tetra­hydro­isoquinoline backbone. For the application of these ligands as catalysts, see: Chakka et al. (2009 ▶); Peters et al. (2010 ▶); Naicker et al. (2010a ▶). For related structures, see: Chakka et al. (2010 ▶). For a related structure with the same chiral centre and conformation of the six-membered ring, see: Naicker et al. (2010b ▶).

Experimental

Crystal data

C18H20N2O

M = 280.36

Hexagonal,

a = 10.1838 (13) Å

c = 25.965 (3) Å

V = 2332.1 (5) Å3

Z = 6

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.22 × 0.12 × 0.03 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

18777 measured reflections

1759 independent reflections

1358 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.088

S = 1.05

1759 reflections

195 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050361/hg2752sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050361/hg2752Isup2.hkl

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

C18H20N2O	Dx = 1.198 Mg m−3
Mr = 280.36	Melting point: 365 K
Hexagonal, P61	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 61	Cell parameters from 18777 reflections
a = 10.1838 (13) Å	θ = 2.3–27.2°
c = 25.965 (3) Å	µ = 0.08 mm−1
V = 2332.1 (5) Å3	T = 173 K
Z = 6	Needle, colourless
F(000) = 900	0.22 × 0.12 × 0.03 mm

Bruker Kappa DUO APEXII diffractometer	1358 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
graphite	θmax = 27.2°, θmin = 2.3°
0.5° φ scans and ω scans	h = −13→12
18777 measured reflections	k = −12→13
1759 independent reflections	l = −33→33

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0377P)2 + 0.3273P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1759 reflections	Δρmax = 0.14 e Å−3
195 parameters	Δρmin = −0.14 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (7)

Experimental. Half sphere of data collected using SAINT strategy (Bruker, 2006). Crystal to detector distance = 40 mm; combination of φ and ω scans of 0.5°, 30 s per °, 2 iterations.

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
O1	0.73695 (19)	0.77313 (19)	0.97396 (7)	0.0450 (5)
N1	0.9118 (2)	1.1026 (2)	0.98992 (8)	0.0385 (5)
N2	0.7085 (2)	0.8382 (2)	0.89310 (8)	0.0362 (5)
H2	0.747 (3)	0.915 (2)	0.8671 (9)	0.051 (8)*
C1	1.0391 (3)	1.2586 (3)	0.98885 (11)	0.0465 (7)
H1A	1.0402	1.3099	1.0214	0.056*
H1B	1.0241	1.3139	0.9602	0.056*
C2	1.1898 (3)	1.2671 (3)	0.98225 (10)	0.0406 (6)
C3	1.3244 (4)	1.4003 (3)	0.99539 (12)	0.0537 (8)
H3	1.3197	1.4848	1.0087	0.064*
C4	1.4632 (3)	1.4096 (3)	0.98919 (13)	0.0595 (8)
H4	1.5535	1.4999	0.9984	0.071*
C5	1.4714 (3)	1.2876 (4)	0.96964 (13)	0.0581 (8)
H5	1.5671	1.2941	0.9652	0.070*
C6	1.3402 (3)	1.1566 (3)	0.95657 (11)	0.0463 (7)
H6	1.3461	1.0725	0.9436	0.056*
C7	1.1987 (3)	1.1457 (3)	0.96216 (10)	0.0374 (6)
C8	1.0561 (3)	1.0021 (3)	0.94725 (11)	0.0378 (6)
H8A	1.0356	0.9225	0.9730	0.045*
H8B	1.0718	0.9668	0.9135	0.045*
C9	0.9188 (3)	1.0240 (3)	0.94379 (10)	0.0345 (5)
H9	0.9283	1.0859	0.9126	0.041*
C10	0.7785 (3)	0.8671 (3)	0.93857 (10)	0.0343 (5)
C11	0.5866 (3)	0.6863 (3)	0.87851 (10)	0.0393 (6)
H11A	0.5110	0.6958	0.8573	0.047*
H11B	0.5349	0.6288	0.9100	0.047*
C12	0.6459 (3)	0.6001 (3)	0.84871 (9)	0.0373 (6)
C13	0.7331 (4)	0.5489 (4)	0.87268 (12)	0.0623 (9)
H13	0.7528	0.5655	0.9085	0.075*
C14	0.7920 (4)	0.4739 (4)	0.84516 (14)	0.0685 (10)
H14	0.8523	0.4402	0.8622	0.082*
C15	0.7643 (4)	0.4478 (4)	0.79358 (13)	0.0615 (9)
H15	0.8053	0.3967	0.7747	0.074*
C16	0.6769 (4)	0.4962 (4)	0.76946 (13)	0.0680 (10)
H16	0.6565	0.4782	0.7337	0.082*
C17	0.6180 (4)	0.5713 (3)	0.79703 (12)	0.0529 (7)
H17	0.5568	0.6037	0.7798	0.063*
C18	0.7705 (3)	1.1059 (4)	0.99296 (14)	0.0573 (8)
H18A	0.6846	1.0019	0.9935	0.086*
H18B	0.7619	1.1594	0.9629	0.086*
H18C	0.7700	1.1586	1.0245	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0379 (9)	0.0402 (10)	0.0409 (10)	0.0076 (8)	−0.0062 (8)	0.0136 (8)
N1	0.0387 (12)	0.0377 (11)	0.0414 (12)	0.0208 (10)	0.0035 (9)	0.0012 (9)
N2	0.0370 (11)	0.0366 (11)	0.0349 (11)	0.0183 (9)	−0.0024 (9)	0.0071 (9)
C1	0.0571 (16)	0.0354 (14)	0.0488 (16)	0.0245 (13)	−0.0015 (13)	−0.0017 (12)
C2	0.0453 (14)	0.0287 (12)	0.0408 (14)	0.0133 (11)	−0.0010 (12)	0.0058 (11)
C3	0.065 (2)	0.0303 (14)	0.0522 (18)	0.0137 (14)	−0.0029 (14)	0.0044 (12)
C4	0.0422 (16)	0.0433 (16)	0.065 (2)	0.0006 (13)	−0.0056 (15)	0.0107 (15)
C5	0.0371 (15)	0.0565 (18)	0.067 (2)	0.0128 (14)	−0.0042 (14)	0.0108 (16)
C6	0.0365 (14)	0.0439 (15)	0.0532 (17)	0.0162 (12)	0.0031 (12)	0.0094 (13)
C7	0.0381 (13)	0.0290 (12)	0.0388 (13)	0.0121 (11)	0.0011 (11)	0.0073 (11)
C8	0.0336 (12)	0.0299 (12)	0.0459 (14)	0.0130 (11)	0.0036 (11)	−0.0001 (11)
C9	0.0349 (13)	0.0321 (12)	0.0340 (12)	0.0149 (10)	0.0029 (10)	0.0071 (10)
C10	0.0315 (12)	0.0360 (13)	0.0356 (13)	0.0170 (10)	0.0005 (10)	0.0067 (10)
C11	0.0295 (13)	0.0442 (14)	0.0403 (14)	0.0156 (11)	−0.0071 (11)	0.0036 (11)
C12	0.0300 (12)	0.0325 (13)	0.0375 (14)	0.0067 (10)	0.0004 (11)	0.0021 (11)
C13	0.073 (2)	0.097 (3)	0.0420 (17)	0.061 (2)	−0.0073 (15)	−0.0093 (16)
C14	0.069 (2)	0.089 (3)	0.067 (2)	0.054 (2)	−0.0099 (18)	−0.0217 (19)
C15	0.0525 (18)	0.0532 (18)	0.064 (2)	0.0151 (15)	0.0066 (16)	−0.0209 (16)
C16	0.085 (3)	0.0545 (19)	0.0404 (16)	0.0168 (18)	−0.0052 (17)	−0.0131 (15)
C17	0.0631 (19)	0.0404 (15)	0.0440 (16)	0.0174 (14)	−0.0140 (14)	−0.0050 (13)
C18	0.0526 (17)	0.067 (2)	0.065 (2)	0.0395 (16)	0.0052 (15)	−0.0012 (16)

O1—C10	1.239 (3)	C8—H8A	0.9900
N1—C18	1.458 (3)	C8—H8B	0.9900
N1—C9	1.462 (3)	C9—C10	1.527 (3)
N1—C1	1.465 (3)	C9—H9	1.0000
N2—C10	1.334 (3)	C11—C12	1.504 (4)
N2—C11	1.469 (3)	C11—H11A	0.9900
N2—H2	0.957 (10)	C11—H11B	0.9900
C1—C2	1.503 (4)	C12—C17	1.373 (4)
C1—H1A	0.9900	C12—C13	1.383 (4)
C1—H1B	0.9900	C13—C14	1.383 (4)
C2—C7	1.386 (4)	C13—H13	0.9500
C2—C3	1.406 (4)	C14—C15	1.367 (5)
C3—C4	1.378 (4)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.365 (5)
C4—C5	1.382 (5)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.385 (5)
C5—C6	1.377 (4)	C16—H16	0.9500
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.396 (4)	C18—H18A	0.9800
C6—H6	0.9500	C18—H18B	0.9800
C7—C8	1.508 (4)	C18—H18C	0.9800
C8—C9	1.524 (3)
C18—N1—C9	112.1 (2)	C8—C9—C10	107.39 (19)
C18—N1—C1	109.0 (2)	N1—C9—H9	109.5
C9—N1—C1	108.61 (19)	C8—C9—H9	109.5
C10—N2—C11	122.5 (2)	C10—C9—H9	109.5
C10—N2—H2	119.4 (18)	O1—C10—N2	123.2 (2)
C11—N2—H2	117.6 (18)	O1—C10—C9	121.5 (2)
N1—C1—C2	112.9 (2)	N2—C10—C9	115.3 (2)
N1—C1—H1A	109.0	N2—C11—C12	111.9 (2)
C2—C1—H1A	109.0	N2—C11—H11A	109.2
N1—C1—H1B	109.0	C12—C11—H11A	109.2
C2—C1—H1B	109.0	N2—C11—H11B	109.2
H1A—C1—H1B	107.8	C12—C11—H11B	109.2
C7—C2—C3	119.0 (3)	H11A—C11—H11B	107.9
C7—C2—C1	120.8 (2)	C17—C12—C13	117.6 (3)
C3—C2—C1	120.2 (3)	C17—C12—C11	121.8 (3)
C4—C3—C2	120.6 (3)	C13—C12—C11	120.6 (2)
C4—C3—H3	119.7	C12—C13—C14	120.9 (3)
C2—C3—H3	119.7	C12—C13—H13	119.5
C3—C4—C5	120.1 (3)	C14—C13—H13	119.5
C3—C4—H4	119.9	C15—C14—C13	120.6 (3)
C5—C4—H4	119.9	C15—C14—H14	119.7
C6—C5—C4	119.7 (3)	C13—C14—H14	119.7
C6—C5—H5	120.2	C16—C15—C14	119.2 (3)
C4—C5—H5	120.2	C16—C15—H15	120.4
C5—C6—C7	121.0 (3)	C14—C15—H15	120.4
C5—C6—H6	119.5	C15—C16—C17	120.2 (3)
C7—C6—H6	119.5	C15—C16—H16	119.9
C2—C7—C6	119.6 (2)	C17—C16—H16	119.9
C2—C7—C8	120.0 (2)	C12—C17—C16	121.5 (3)
C6—C7—C8	120.4 (2)	C12—C17—H17	119.3
C7—C8—C9	112.5 (2)	C16—C17—H17	119.3
C7—C8—H8A	109.1	N1—C18—H18A	109.5
C9—C8—H8A	109.1	N1—C18—H18B	109.5
C7—C8—H8B	109.1	H18A—C18—H18B	109.5
C9—C8—H8B	109.1	N1—C18—H18C	109.5
H8A—C8—H8B	107.8	H18A—C18—H18C	109.5
N1—C9—C8	109.34 (19)	H18B—C18—H18C	109.5
N1—C9—C10	111.7 (2)
C18—N1—C1—C2	−176.3 (2)	C1—N1—C9—C10	−172.63 (19)
C9—N1—C1—C2	−53.9 (3)	C7—C8—C9—N1	−48.2 (3)
N1—C1—C2—C7	20.3 (4)	C7—C8—C9—C10	−169.6 (2)
N1—C1—C2—C3	−161.2 (2)	C11—N2—C10—O1	−7.5 (4)
C7—C2—C3—C4	−1.0 (4)	C11—N2—C10—C9	170.4 (2)
C1—C2—C3—C4	−179.6 (3)	N1—C9—C10—O1	−53.7 (3)
C2—C3—C4—C5	0.4 (5)	C8—C9—C10—O1	66.2 (3)
C3—C4—C5—C6	−0.2 (5)	N1—C9—C10—N2	128.3 (2)
C4—C5—C6—C7	0.8 (4)	C8—C9—C10—N2	−111.8 (2)
C3—C2—C7—C6	1.6 (4)	C10—N2—C11—C12	−94.2 (3)
C1—C2—C7—C6	−179.9 (2)	N2—C11—C12—C17	−109.0 (3)
C3—C2—C7—C8	−179.4 (2)	N2—C11—C12—C13	70.0 (3)
C1—C2—C7—C8	−0.8 (4)	C17—C12—C13—C14	1.2 (5)
C5—C6—C7—C2	−1.5 (4)	C11—C12—C13—C14	−177.9 (3)
C5—C6—C7—C8	179.4 (3)	C12—C13—C14—C15	−0.4 (6)
C2—C7—C8—C9	14.7 (3)	C13—C14—C15—C16	−0.3 (5)
C6—C7—C8—C9	−166.2 (2)	C14—C15—C16—C17	0.3 (5)
C18—N1—C9—C8	−170.9 (2)	C13—C12—C17—C16	−1.1 (4)
C1—N1—C9—C8	68.7 (2)	C11—C12—C17—C16	177.9 (3)
C18—N1—C9—C10	−52.2 (3)	C15—C16—C17—C12	0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.96 (2)	1.92 (2)	2.852 (3)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.96 (2)	1.92 (2)	2.852 (3)	165 (3)

Symmetry code: (i) .