(3aRS,9bSR)-3-(4-Chloro-phen-yl)-1-methyl-1,2,3,3a,4,9b-hexa-hydro-chromeno[4,3-b]pyrrole-3a-carbonitrile.

In the mol-ecule of the title compound, C(19)H(17)ClN(2)O, the heterocyclic six-membered ring adopts a half-chair conformation, while the pyrrolidine ring has an envelope conformation. In the crystal structure, C-Cl⋯π [Cl⋯centroid = 3.680 (2) Å] inter-actions and van der Waals forces are present.

Related literature

For general background, see: Caine (1993 ▶); Tidey (1992 ▶); Carlson (1993 ▶); Sokoloff et al. (1990 ▶); Wilner (1985 ▶); Biava et al. (2005 ▶); Fernandes et al. (2004 ▶); Borthwick et al. (2000 ▶); Jiang et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1995 ▶).

Experimental

Crystal data

C19H17ClN2O

M = 324.80

Monoclinic,

a = 8.8659 (4) Å

b = 7.6009 (3) Å

c = 24.2026 (10) Å

β = 97.701 (1)°

V = 1616.27 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 294 (2) K

0.28 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEX2 diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.935, T max = 0.953

21338 measured reflections

5199 independent reflections

3858 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.138

S = 1.03

5199 reflections

208 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062113/hk2395sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062113/hk2395Isup2.hkl

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

C19H17ClN2O	F000 = 680
Mr = 324.80	Dx = 1.335 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7082 reflections
a = 8.8659 (4) Å	θ = 1.7–25.0º
b = 7.6009 (3) Å	µ = 0.24 mm−1
c = 24.2026 (10) Å	T = 294 (2) K
β = 97.701 (1)º	Prism, colourless
V = 1616.27 (12) Å3	0.28 × 0.20 × 0.20 mm
Z = 4

Bruker APEX2 kappa diffractometer	5199 independent reflections
Radiation source: fine-focus sealed tube	3858 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 294(2) K	θmax = 31.2º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(Blessing, 1995)	h = −12→11
Tmin = 0.935, Tmax = 0.953	k = −10→11
21338 measured reflections	l = −35→35

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0639P)2 + 0.427P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
5199 reflections	Δρmax = 0.29 e Å−3
208 parameters	Δρmin = −0.29 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
Cl1	0.81942 (5)	−0.45073 (7)	0.00516 (2)	0.06969 (17)
O1	0.33531 (13)	0.11121 (15)	0.24679 (4)	0.0509 (3)
N1	0.07255 (13)	−0.04341 (16)	0.12043 (5)	0.0419 (3)
N2	0.57906 (16)	0.1425 (2)	0.13922 (7)	0.0626 (4)
C2	0.14526 (17)	−0.1758 (2)	0.08910 (6)	0.0484 (3)
H2A	0.1547	−0.1343	0.0518	0.058*
H2B	0.0876	−0.2846	0.0864	0.058*
C3	0.30137 (16)	−0.20196 (17)	0.12296 (5)	0.0388 (3)
H3	0.2894	−0.2909	0.1514	0.047*
C4	0.32937 (14)	−0.02060 (16)	0.15421 (5)	0.0336 (2)
C5	0.32588 (18)	−0.04940 (19)	0.21657 (5)	0.0434 (3)
H5A	0.2323	−0.1094	0.2219	0.052*
H5B	0.4103	−0.1245	0.2312	0.052*
C6	0.23237 (16)	0.23694 (18)	0.22598 (5)	0.0399 (3)
C7	0.20691 (19)	0.3728 (2)	0.26234 (6)	0.0511 (4)
H7	0.2563	0.3724	0.2988	0.061*
C8	0.1087 (2)	0.5073 (2)	0.24431 (8)	0.0579 (4)
H8	0.0908	0.5970	0.2688	0.069*
C9	0.0368 (2)	0.5099 (2)	0.19038 (8)	0.0577 (4)
H9	−0.0294	0.6011	0.1783	0.069*
C10	0.06331 (17)	0.3757 (2)	0.15411 (6)	0.0468 (3)
H10	0.0161	0.3795	0.1174	0.056*
C11	0.15891 (14)	0.23538 (17)	0.17135 (5)	0.0352 (3)
C12	0.19023 (14)	0.09239 (17)	0.13132 (5)	0.0335 (2)
H12	0.2081	0.1458	0.0959	0.040*
C13	0.42773 (15)	−0.26473 (16)	0.09160 (5)	0.0366 (3)
C14	0.44773 (19)	−0.2015 (2)	0.03930 (6)	0.0487 (3)
H14	0.3799	−0.1188	0.0220	0.058*
C15	0.56716 (19)	−0.2597 (2)	0.01243 (6)	0.0502 (4)
H15	0.5793	−0.2168	−0.0227	0.060*
C16	0.66710 (16)	−0.3812 (2)	0.03828 (6)	0.0443 (3)
C17	0.64861 (19)	−0.4491 (2)	0.08934 (7)	0.0525 (4)
H17	0.7159	−0.5332	0.1061	0.063*
C18	0.52856 (18)	−0.3910 (2)	0.11562 (6)	0.0469 (3)
H18	0.5153	−0.4377	0.1502	0.056*
C19	0.47093 (15)	0.06885 (18)	0.14530 (6)	0.0405 (3)
C20	−0.07204 (18)	0.0173 (3)	0.09117 (8)	0.0615 (5)
H20A	−0.1149	0.1038	0.1134	0.092*
H20B	−0.1407	−0.0804	0.0846	0.092*
H20C	−0.0560	0.0685	0.0562	0.092*

	U11	U22	U33	U12	U13	U23
Cl1	0.0478 (2)	0.0821 (3)	0.0832 (3)	0.0010 (2)	0.0237 (2)	−0.0308 (2)
O1	0.0589 (6)	0.0565 (6)	0.0342 (5)	0.0075 (5)	−0.0052 (4)	−0.0084 (4)
N1	0.0318 (5)	0.0495 (7)	0.0443 (6)	−0.0025 (5)	0.0050 (4)	−0.0124 (5)
N2	0.0406 (7)	0.0581 (8)	0.0890 (11)	−0.0015 (6)	0.0083 (7)	0.0112 (8)
C2	0.0416 (7)	0.0525 (8)	0.0515 (8)	−0.0031 (6)	0.0073 (6)	−0.0189 (7)
C3	0.0421 (7)	0.0355 (6)	0.0402 (6)	0.0001 (5)	0.0110 (5)	−0.0038 (5)
C4	0.0324 (6)	0.0360 (6)	0.0325 (5)	0.0017 (5)	0.0049 (4)	−0.0006 (4)
C5	0.0511 (8)	0.0443 (7)	0.0341 (6)	0.0052 (6)	0.0028 (5)	0.0021 (5)
C6	0.0395 (7)	0.0438 (7)	0.0371 (6)	−0.0040 (5)	0.0083 (5)	−0.0069 (5)
C7	0.0539 (9)	0.0562 (9)	0.0450 (7)	−0.0103 (7)	0.0130 (6)	−0.0184 (6)
C8	0.0607 (10)	0.0504 (8)	0.0675 (10)	−0.0045 (7)	0.0269 (8)	−0.0207 (8)
C9	0.0559 (10)	0.0471 (8)	0.0736 (11)	0.0119 (7)	0.0217 (8)	−0.0053 (7)
C10	0.0446 (7)	0.0477 (8)	0.0490 (7)	0.0076 (6)	0.0096 (6)	−0.0002 (6)
C11	0.0326 (6)	0.0383 (6)	0.0357 (6)	−0.0011 (5)	0.0088 (5)	−0.0031 (5)
C12	0.0316 (5)	0.0396 (6)	0.0294 (5)	0.0025 (5)	0.0043 (4)	−0.0021 (4)
C13	0.0407 (7)	0.0325 (6)	0.0372 (6)	0.0011 (5)	0.0073 (5)	−0.0031 (5)
C14	0.0540 (8)	0.0475 (8)	0.0468 (7)	0.0123 (7)	0.0146 (6)	0.0108 (6)
C15	0.0550 (9)	0.0543 (8)	0.0442 (7)	0.0015 (7)	0.0177 (6)	0.0032 (6)
C16	0.0371 (7)	0.0453 (7)	0.0517 (7)	−0.0033 (6)	0.0100 (6)	−0.0168 (6)
C17	0.0453 (8)	0.0535 (9)	0.0573 (9)	0.0148 (7)	0.0016 (6)	0.0003 (7)
C18	0.0507 (8)	0.0507 (8)	0.0388 (6)	0.0079 (6)	0.0043 (6)	0.0037 (6)
C19	0.0346 (6)	0.0396 (7)	0.0467 (7)	0.0047 (5)	0.0031 (5)	0.0015 (5)
C20	0.0334 (7)	0.0812 (12)	0.0671 (10)	0.0026 (7)	−0.0031 (7)	−0.0231 (9)

C2—N1	1.4610 (18)	C10—C11	1.3909 (19)
C2—C3	1.524 (2)	C10—H10	0.9300
C2—H2A	0.9700	C11—C12	1.5063 (17)
C2—H2B	0.9700	C12—N1	1.4662 (17)
C3—C13	1.5122 (18)	C12—H12	0.9800
C3—C4	1.5760 (18)	C13—C18	1.3852 (19)
C3—H3	0.9800	C13—C14	1.3873 (18)
C4—C19	1.4684 (18)	C14—C15	1.387 (2)
C4—C5	1.5296 (17)	C14—H14	0.9300
C4—C12	1.5438 (17)	C15—C16	1.372 (2)
C5—O1	1.4197 (17)	C15—H15	0.9300
C5—H5A	0.9700	C16—C17	1.369 (2)
C5—H5B	0.9700	C16—Cl1	1.7423 (14)
C6—O1	1.3700 (18)	C17—C18	1.384 (2)
C6—C11	1.3935 (18)	C17—H17	0.9300
C6—C7	1.3945 (19)	C18—H18	0.9300
C7—C8	1.376 (3)	C19—N2	1.1368 (19)
C7—H7	0.9300	C20—N1	1.454 (2)
C8—C9	1.374 (3)	C20—H20A	0.9600
C8—H8	0.9300	C20—H20B	0.9600
C9—C10	1.386 (2)	C20—H20C	0.9600
C9—H9	0.9300
C6—O1—C5	114.84 (10)	C8—C9—H9	120.2
C20—N1—C2	112.77 (11)	C10—C9—H9	120.2
C20—N1—C12	115.08 (13)	C9—C10—C11	121.50 (14)
C2—N1—C12	103.02 (10)	C11—C10—H10	119.2
N1—C2—C3	104.05 (11)	C10—C11—C6	117.81 (12)
N1—C2—H2A	110.9	C10—C11—C12	121.18 (12)
C3—C2—H2A	110.9	C6—C11—C12	120.89 (11)
N1—C2—H2B	110.9	N1—C12—C11	115.81 (10)
C3—C2—H2B	110.9	N1—C12—C4	100.84 (10)
H2A—C2—H2B	109.0	C11—C12—C4	112.20 (10)
C13—C3—C2	116.85 (11)	N1—C12—H12	109.2
C13—C3—C4	115.92 (11)	C11—C12—H12	109.2
C2—C3—C4	102.55 (11)	C4—C12—H12	109.2
C13—C3—H3	107.0	C18—C13—C14	117.95 (13)
C2—C3—H3	107.0	C18—C13—C3	119.19 (12)
C4—C3—H3	107.0	C14—C13—C3	122.86 (12)
C19—C4—C5	109.99 (11)	C15—C14—C13	121.09 (14)
C19—C4—C12	110.32 (10)	C15—C14—H14	119.5
C5—C4—C12	108.23 (10)	C13—C14—H14	119.5
C19—C4—C3	114.67 (11)	C16—C15—C14	119.20 (13)
C5—C4—C3	109.00 (10)	C16—C15—H15	120.4
C12—C4—C3	104.33 (10)	C14—C15—H15	120.4
O1—C5—C4	112.18 (11)	C17—C16—C15	121.16 (13)
O1—C5—H5A	109.2	C17—C16—Cl1	119.66 (12)
C4—C5—H5A	109.2	C15—C16—Cl1	119.18 (12)
O1—C5—H5B	109.2	C16—C17—C18	119.15 (14)
C4—C5—H5B	109.2	C16—C17—H17	120.4
H5A—C5—H5B	107.9	C18—C17—H17	120.4
O1—C6—C11	123.13 (11)	C17—C18—C13	121.41 (14)
O1—C6—C7	116.14 (12)	C17—C18—H18	119.3
C11—C6—C7	120.70 (14)	C13—C18—H18	119.3
C8—C7—C6	119.94 (14)	N2—C19—C4	177.88 (17)
C8—C7—H7	120.0	N1—C20—H20A	109.5
C6—C7—H7	120.0	N1—C20—H20B	109.5
C9—C8—C7	120.36 (14)	H20A—C20—H20B	109.5
C9—C8—H8	119.8	N1—C20—H20C	109.5
C7—C8—H8	119.8	H20A—C20—H20C	109.5
C8—C9—C10	119.64 (16)	H20B—C20—H20C	109.5
N1—C2—C3—C13	−153.76 (12)	C3—C4—C12—N1	31.53 (11)
N1—C2—C3—C4	−25.83 (14)	C19—C4—C12—C11	−80.99 (13)
C13—C3—C4—C19	4.02 (16)	C5—C4—C12—C11	39.40 (14)
C2—C3—C4—C19	−124.49 (12)	C3—C4—C12—C11	155.38 (10)
C13—C3—C4—C5	−119.76 (12)	C2—C3—C13—C18	−138.60 (14)
C2—C3—C4—C5	111.72 (12)	C4—C3—C13—C18	100.27 (15)
C13—C3—C4—C12	124.80 (12)	C2—C3—C13—C14	41.3 (2)
C2—C3—C4—C12	−3.72 (13)	C4—C3—C13—C14	−79.83 (17)
C19—C4—C5—O1	59.31 (15)	C18—C13—C14—C15	−1.5 (2)
C12—C4—C5—O1	−61.28 (15)	C3—C13—C14—C15	178.56 (14)
C3—C4—C5—O1	−174.18 (11)	C13—C14—C15—C16	−0.2 (3)
O1—C6—C7—C8	178.08 (14)	C14—C15—C16—C17	1.7 (2)
C11—C6—C7—C8	−0.2 (2)	C14—C15—C16—Cl1	−178.65 (13)
C6—C7—C8—C9	−0.8 (2)	C15—C16—C17—C18	−1.3 (2)
C7—C8—C9—C10	0.2 (3)	Cl1—C16—C17—C18	179.04 (12)
C8—C9—C10—C11	1.5 (3)	C16—C17—C18—C13	−0.5 (2)
C9—C10—C11—C6	−2.4 (2)	C14—C13—C18—C17	1.9 (2)
C9—C10—C11—C12	−178.46 (14)	C3—C13—C18—C17	−178.16 (14)
O1—C6—C11—C10	−176.39 (13)	C3—C2—N1—C20	172.67 (14)
C7—C6—C11—C10	1.7 (2)	C3—C2—N1—C12	47.99 (14)
O1—C6—C11—C12	−0.3 (2)	C11—C12—N1—C20	66.39 (15)
C7—C6—C11—C12	177.82 (12)	C4—C12—N1—C20	−172.28 (11)
C10—C11—C12—N1	−80.29 (16)	C11—C12—N1—C2	−170.45 (11)
C6—C11—C12—N1	103.76 (14)	C4—C12—N1—C2	−49.13 (12)
C10—C11—C12—C4	164.69 (12)	C11—C6—O1—C5	−20.14 (19)
C6—C11—C12—C4	−11.26 (17)	C7—C6—O1—C5	161.65 (13)
C19—C4—C12—N1	155.17 (10)	C4—C5—O1—C6	51.71 (16)
C5—C4—C12—N1	−84.44 (12)