Absolute configuration of odorine.

The title compound, known as odorine or roxburghiline {systematic name: (S)-N-[(R)-1-cinnamoylpyrrolidin-2-yl]-2-methyl-butanamide}, C(18)H(24)N(2)O(2), is a nitro-genous compound isolated from the leaves of Aglaia odorata. The absolute configuration was determined by refinement of the Flack parameter with data collected using Cu Kα radiation showing positions 2 and 2' to be S and R, respectively. The pyrrolidine ring adopts an envelope conformation. In the crystal, mol-ecules are linked into chains along [010] by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For ring conformations, see: Cremer & Pople (1975 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For background to the Aglaia plants and their biological activity, see: Brader et al. (1998 ▶); Cui et al. (1997 ▶); Engelmeier et al. (2000 ▶); Hayashi et al. (1982 ▶); Inada et al. (2001 ▶); Nugroho et al. (1999 ▶); Purushothaman et al. 1979 ▶); Saifah et al. (1993 ▶); Shiengthong et al. (1979 ▶). For related structures, see: Babidge et al. (1980 ▶); Dumontet et al. (1996 ▶); Hayashi et al. (1982 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H24N2O2

M = 300.39

Monoclinic,

a = 18.8909 (3) Å

b = 6.8398 (1) Å

c = 13.4174 (2) Å

β = 107.054 (1)°

V = 1657.43 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.63 mm−1

T = 100 K

0.57 × 0.16 × 0.13 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.718, T max = 0.924

10656 measured reflections

2625 independent reflections

2606 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.096

S = 1.16

2625 reflections

205 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 1036 Friedel pairs

Flack parameter: 0.03 (18)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034227/lh5122sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034227/lh5122Isup2.hkl

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

C18H24N2O2	F(000) = 648
Mr = 300.39	Dx = 1.204 Mg m−3
Monoclinic, C2	Melting point = 476–478 K
Hall symbol: C 2y	Cu Kα radiation, λ = 1.54178 Å
a = 18.8909 (3) Å	Cell parameters from 2625 reflections
b = 6.8398 (1) Å	θ = 6.8–67.4°
c = 13.4174 (2) Å	µ = 0.63 mm−1
β = 107.054 (1)°	T = 100 K
V = 1657.43 (4) Å3	Needle, colorless
Z = 4	0.57 × 0.16 × 0.13 mm

Bruker APEXII DUO CCD area-detector diffractometer	2625 independent reflections
Radiation source: sealed tube	2606 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 67.4°, θmin = 6.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→22
Tmin = 0.718, Tmax = 0.924	k = −7→6
10656 measured reflections	l = −16→16

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.2381P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max = 0.001
2625 reflections	Δρmax = 0.21 e Å−3
205 parameters	Δρmin = −0.27 e Å−3
1 restraint	Absolute structure: Flack (1983), 1036 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (18)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.68617 (5)	0.99471 (16)	0.55658 (7)	0.0243 (2)
O2	0.97777 (6)	0.88734 (17)	0.73395 (8)	0.0315 (3)
N1	0.79446 (6)	0.99195 (19)	0.51776 (8)	0.0218 (2)
H1N2	0.8859 (10)	0.691 (3)	0.5433 (14)	0.030 (5)*
N2	0.90244 (6)	0.78710 (19)	0.57796 (9)	0.0217 (3)
C1	0.87323 (8)	0.9894 (3)	0.92951 (11)	0.0299 (3)
H1A	0.9038	1.0059	0.8870	0.036*
C2	0.90374 (8)	0.9818 (3)	1.03621 (11)	0.0348 (4)
H2A	0.9548	0.9923	1.0651	0.042*
C3	0.85882 (8)	0.9585 (3)	1.10083 (11)	0.0325 (4)
H3A	0.8797	0.9538	1.1728	0.039*
C4	0.78306 (9)	0.9425 (3)	1.05783 (11)	0.0337 (4)
H4A	0.7528	0.9273	1.1008	0.040*
C5	0.75221 (8)	0.9490 (2)	0.95025 (11)	0.0285 (3)
H5A	0.7012	0.9376	0.9217	0.034*
C6	0.79653 (7)	0.9725 (2)	0.88465 (10)	0.0233 (3)
C7	0.76210 (7)	0.9768 (2)	0.77145 (10)	0.0236 (3)
H7A	0.7107	0.9679	0.7481	0.028*
C8	0.79691 (7)	0.9920 (2)	0.69898 (9)	0.0219 (3)
H8A	0.8483	1.0019	0.7190	0.026*
C9	0.75502 (7)	0.9936 (2)	0.58677 (9)	0.0207 (3)
C10	0.75678 (7)	0.9890 (2)	0.40514 (9)	0.0233 (3)
H10A	0.7308	1.1109	0.3826	0.028*
H10B	0.7217	0.8819	0.3871	0.028*
C11	0.81922 (8)	0.9613 (2)	0.35579 (10)	0.0275 (3)
H11A	0.8097	1.0348	0.2914	0.033*
H11B	0.8253	0.8243	0.3414	0.033*
C12	0.88773 (8)	1.0396 (2)	0.43814 (11)	0.0276 (3)
H12A	0.9325	0.9808	0.4303	0.033*
H12B	0.8912	1.1805	0.4329	0.033*
C13	0.87590 (7)	0.9813 (2)	0.54206 (10)	0.0222 (3)
H13A	0.8990	1.0781	0.5956	0.027*
C14	0.95055 (7)	0.7544 (2)	0.67329 (11)	0.0237 (3)
C15	0.97075 (8)	0.5412 (2)	0.69919 (11)	0.0293 (3)
H15A	0.9332	0.4576	0.6527	0.035*
C16	1.04558 (10)	0.5039 (3)	0.67983 (16)	0.0512 (5)
H16A	1.0413	0.5272	0.6077	0.077*
H16B	1.0603	0.3708	0.6971	0.077*
H16C	1.0821	0.5903	0.7225	0.077*
C17	0.97552 (9)	0.4934 (3)	0.81232 (12)	0.0356 (4)
H17A	0.9971	0.3644	0.8290	0.043*
H17B	1.0085	0.5865	0.8576	0.043*
C18	0.90143 (10)	0.4977 (3)	0.83531 (12)	0.0406 (4)
H18A	0.9089	0.4729	0.9081	0.061*
H18B	0.8696	0.3990	0.7948	0.061*
H18C	0.8790	0.6238	0.8176	0.061*

	U11	U22	U33	U12	U13	U23
O1	0.0229 (5)	0.0260 (6)	0.0230 (4)	0.0040 (4)	0.0051 (3)	0.0031 (4)
O2	0.0301 (5)	0.0298 (6)	0.0277 (5)	−0.0005 (4)	−0.0025 (4)	−0.0062 (5)
N1	0.0222 (5)	0.0231 (6)	0.0193 (5)	0.0013 (5)	0.0045 (4)	0.0013 (5)
N2	0.0225 (5)	0.0209 (7)	0.0202 (6)	−0.0006 (5)	0.0039 (4)	−0.0046 (5)
C1	0.0277 (7)	0.0399 (9)	0.0226 (6)	0.0012 (7)	0.0080 (5)	0.0015 (7)
C2	0.0269 (7)	0.0507 (10)	0.0245 (7)	0.0036 (7)	0.0038 (5)	−0.0006 (8)
C3	0.0384 (8)	0.0390 (10)	0.0180 (6)	0.0045 (7)	0.0050 (5)	0.0014 (6)
C4	0.0379 (8)	0.0409 (11)	0.0253 (7)	0.0019 (7)	0.0137 (6)	0.0029 (6)
C5	0.0263 (7)	0.0324 (9)	0.0264 (7)	0.0017 (6)	0.0074 (5)	0.0016 (6)
C6	0.0268 (6)	0.0209 (8)	0.0217 (6)	0.0049 (6)	0.0063 (5)	0.0022 (6)
C7	0.0234 (6)	0.0214 (7)	0.0246 (7)	0.0038 (6)	0.0048 (5)	0.0019 (6)
C8	0.0228 (6)	0.0194 (7)	0.0215 (6)	0.0031 (6)	0.0032 (5)	0.0014 (6)
C9	0.0239 (6)	0.0153 (7)	0.0221 (6)	0.0031 (6)	0.0053 (5)	0.0014 (6)
C10	0.0275 (6)	0.0218 (7)	0.0187 (6)	0.0032 (6)	0.0037 (5)	0.0011 (6)
C11	0.0354 (7)	0.0280 (8)	0.0201 (6)	0.0028 (6)	0.0098 (5)	0.0017 (6)
C12	0.0304 (7)	0.0277 (8)	0.0276 (7)	−0.0002 (6)	0.0132 (5)	0.0028 (6)
C13	0.0219 (6)	0.0214 (7)	0.0234 (6)	−0.0015 (5)	0.0070 (5)	−0.0018 (6)
C14	0.0174 (6)	0.0291 (9)	0.0244 (7)	0.0013 (5)	0.0058 (5)	−0.0013 (6)
C15	0.0278 (7)	0.0293 (9)	0.0290 (7)	0.0059 (6)	0.0058 (6)	−0.0003 (6)
C16	0.0451 (9)	0.0479 (13)	0.0675 (12)	0.0202 (9)	0.0274 (9)	0.0085 (10)
C17	0.0397 (8)	0.0319 (9)	0.0304 (7)	0.0055 (7)	0.0027 (6)	0.0066 (7)
C18	0.0535 (9)	0.0358 (10)	0.0347 (8)	0.0013 (8)	0.0163 (7)	0.0039 (8)

O1—C9	1.2437 (16)	C10—C11	1.5243 (18)
O2—C14	1.2280 (19)	C10—H10A	0.9700
N1—C9	1.3480 (17)	C10—H10B	0.9700
N1—C10	1.4695 (15)	C11—C12	1.531 (2)
N1—C13	1.4780 (16)	C11—H11A	0.9700
N2—C14	1.3529 (17)	C11—H11B	0.9700
N2—C13	1.451 (2)	C12—C13	1.5284 (18)
N2—H1N2	0.81 (2)	C12—H12A	0.9700
C1—C2	1.3787 (19)	C12—H12B	0.9700
C1—C6	1.401 (2)	C13—H13A	0.9800
C1—H1A	0.9300	C14—C15	1.522 (2)
C2—C3	1.389 (2)	C15—C17	1.529 (2)
C2—H2A	0.9300	C15—C16	1.532 (2)
C3—C4	1.382 (2)	C15—H15A	0.9800
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.3898 (19)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C5—C6	1.3907 (19)	C17—C18	1.519 (2)
C5—H5A	0.9300	C17—H17A	0.9700
C6—C7	1.4667 (17)	C17—H17B	0.9700
C7—C8	1.3282 (18)	C18—H18A	0.9600
C7—H7A	0.9300	C18—H18B	0.9600
C8—C9	1.4813 (17)	C18—H18C	0.9600
C8—H8A	0.9300
C9—N1—C10	120.52 (10)	C10—C11—H11B	111.0
C9—N1—C13	126.73 (10)	C12—C11—H11B	111.0
C10—N1—C13	112.65 (10)	H11A—C11—H11B	109.0
C14—N2—C13	122.40 (12)	C13—C12—C11	104.37 (11)
C14—N2—H1N2	116.5 (13)	C13—C12—H12A	110.9
C13—N2—H1N2	120.9 (13)	C11—C12—H12A	110.9
C2—C1—C6	120.50 (13)	C13—C12—H12B	110.9
C2—C1—H1A	119.7	C11—C12—H12B	110.9
C6—C1—H1A	119.7	H12A—C12—H12B	108.9
C1—C2—C3	120.45 (13)	N2—C13—N1	110.75 (11)
C1—C2—H2A	119.8	N2—C13—C12	114.38 (12)
C3—C2—H2A	119.8	N1—C13—C12	101.95 (10)
C4—C3—C2	119.75 (13)	N2—C13—H13A	109.8
C4—C3—H3A	120.1	N1—C13—H13A	109.8
C2—C3—H3A	120.1	C12—C13—H13A	109.8
C3—C4—C5	119.91 (14)	O2—C14—N2	122.61 (14)
C3—C4—H4A	120.0	O2—C14—C15	122.00 (12)
C5—C4—H4A	120.0	N2—C14—C15	115.36 (12)
C4—C5—C6	120.94 (13)	C14—C15—C17	111.68 (13)
C4—C5—H5A	119.5	C14—C15—C16	107.63 (14)
C6—C5—H5A	119.5	C17—C15—C16	110.13 (13)
C5—C6—C1	118.44 (12)	C14—C15—H15A	109.1
C5—C6—C7	119.43 (12)	C17—C15—H15A	109.1
C1—C6—C7	122.13 (12)	C16—C15—H15A	109.1
C8—C7—C6	126.53 (12)	C15—C16—H16A	109.5
C8—C7—H7A	116.7	C15—C16—H16B	109.5
C6—C7—H7A	116.7	H16A—C16—H16B	109.5
C7—C8—C9	120.87 (11)	C15—C16—H16C	109.5
C7—C8—H8A	119.6	H16A—C16—H16C	109.5
C9—C8—H8A	119.6	H16B—C16—H16C	109.5
O1—C9—N1	120.81 (11)	C18—C17—C15	114.07 (12)
O1—C9—C8	121.80 (11)	C18—C17—H17A	108.7
N1—C9—C8	117.39 (11)	C15—C17—H17A	108.7
N1—C10—C11	104.19 (10)	C18—C17—H17B	108.7
N1—C10—H10A	110.9	C15—C17—H17B	108.7
C11—C10—H10A	110.9	H17A—C17—H17B	107.6
N1—C10—H10B	110.9	C17—C18—H18A	109.5
C11—C10—H10B	110.9	C17—C18—H18B	109.5
H10A—C10—H10B	108.9	H18A—C18—H18B	109.5
C10—C11—C12	103.95 (11)	C17—C18—H18C	109.5
C10—C11—H11A	111.0	H18A—C18—H18C	109.5
C12—C11—H11A	111.0	H18B—C18—H18C	109.5
C6—C1—C2—C3	−0.4 (3)	N1—C10—C11—C12	−24.24 (15)
C1—C2—C3—C4	0.2 (3)	C10—C11—C12—C13	35.81 (15)
C2—C3—C4—C5	0.2 (3)	C14—N2—C13—N1	−119.95 (13)
C3—C4—C5—C6	−0.3 (3)	C14—N2—C13—C12	125.55 (13)
C4—C5—C6—C1	0.0 (2)	C9—N1—C13—N2	72.51 (17)
C4—C5—C6—C7	179.40 (15)	C10—N1—C13—N2	−103.96 (13)
C2—C1—C6—C5	0.4 (3)	C9—N1—C13—C12	−165.39 (14)
C2—C1—C6—C7	−179.02 (17)	C10—N1—C13—C12	18.14 (16)
C5—C6—C7—C8	−177.81 (15)	C11—C12—C13—N2	86.96 (14)
C1—C6—C7—C8	1.6 (3)	C11—C12—C13—N1	−32.61 (14)
C6—C7—C8—C9	179.71 (14)	C13—N2—C14—O2	−3.6 (2)
C10—N1—C9—O1	−0.7 (2)	C13—N2—C14—C15	178.31 (11)
C13—N1—C9—O1	−176.95 (14)	O2—C14—C15—C17	41.89 (18)
C10—N1—C9—C8	178.64 (13)	N2—C14—C15—C17	−139.99 (13)
C13—N1—C9—C8	2.4 (2)	O2—C14—C15—C16	−79.11 (18)
C7—C8—C9—O1	5.1 (2)	N2—C14—C15—C16	99.01 (15)
C7—C8—C9—N1	−174.23 (14)	C14—C15—C17—C18	68.78 (18)
C9—N1—C10—C11	−172.93 (12)	C16—C15—C17—C18	−171.68 (16)
C13—N1—C10—C11	3.78 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1i	0.81 (2)	2.09 (2)	2.8789 (16)	163 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.81 (2)	2.09 (2)	2.8789 (16)	163 (2)

Symmetry code: (i) .