(3aRS,9bSR)-3-(4-Chloro­phen­yl)-1-methyl-1,2,3,3a,4,9b-hexa­hydro­chromeno[4,3-b]pyrrole-3a-carbonitrile

Nirmala, S.; Kamala, E.T.S.; Sudha, L.; Ramesh, E.; Raghunathan, R.

doi:10.1107/S1600536807062113

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o73

https://doi.org/10.1107/S1600536807062113

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(3aRS,9bSR)-3-(4-Chlorophenyl)-1-methyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-3a-carbonitrile

S. Nirmala,^a E. Theboral Sugi Kamala,^a L. Sudha,^b ^* E. Ramesh ^c and R. Raghunathan ^c

^aDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India, ^bDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
^*Correspondence e-mail: sudhasuraj@rediffmail.com

(Received 21 November 2007; accepted 22 November 2007; online 6 December 2007)

In the molecule of the title compound, C₁₉H₁₇ClN₂O, 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] interactions 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_r = 324.80
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.138
S = 1.03
5199 reflections
208 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062113/hk2395Isup2.hkl

checkCIF report

Comment top

Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993), aggressiveness (Tidey, 1992), parkinson's disease (Carlson, 1993), psychoses, memory disorders (Sokoloff et al., 1990), anxiety and depression (Wilner, 1985). Pyrrole derivatives have good invitro against mycobacteria and candidae (Biava et al., 2005). These derivatives also possess anti-inflammatory (Fernandes et al., 2004) and antiviral (Borthwick et al., 2000) activities. It has also been shown that N-substituted pyrrole derivatives inhibit human immuno deficiency virus type-I (HIV-I) (Jiang et al., 2004). In view of its medicinal importance, the crystal structure determination of the title compound, (I), was carried out.

In the molecule of (I), (Fig. 1) the bond lengths and angles are within normal ranges (Allen et al., 1987). The sum of bond angles around atom N1 [330.9 (4)°] indicates sp³ hybridization. Rings A (C6—C11) and D (C13—C18) are, of course, planar and they are oriented at a dihedral angle of 46.7 (5)°. The heterocyclic ring B (O1/C4—C6/C11/C12) adopts a half-chair conformation with asymmetry parameters of ΔC₂(C4) = 0.028 (1) (Nardelli, 1995) and puckering parameters of q₂ = 0.778 (3) Å, q₃ = 0.054 (2) Å and φ = - 26.5 (2)° (Cremer & Pople, 1975). Atom C5 displaced by -0.645 (2) Å from the plane of the other five ring atoms. The pyrrolidine ring C (N1/C2—C4/C12) has an envelope conformation with asymmetry parameters of ΔC_s(N1) = 0.030 (1) (Nardelli, 1995) and puckering parameters of q₂ = 0.470 (1) Å and φ =175.3 (2)° (Cremer & Pople, 1975). Atom N1 displaced by -0.691 (2) Å from the plane of the other four ring atoms.

In the crystal structure, no significant intermolecular π–π interactions are observed between two chlorophenyl rings as their centroids are seperated by 4.1049 (9) Å. Weak intermolecular C—Cl···π interactions (Spek, 2003), with C16···Cg4 = 3.680 (2) Å and Cl1···Cg4 = 3.858 (8) Å [Cg4 denotes centroid of ring D] and van der Waals forces stabilize the crystal structure (Fig. 2).

Related literature top

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 top

For the preparation of the title compound, a solution of (Z)-2-((2-formyl- phenoxy)methyl)-3-(4-chlorophenyl)acrylonitrile (1 mmol) and sarcosine (1 mmol) in anhydrous methanol (10 ml) was refluxed. Completion of the reaction was evidenced by thin layer chromatography analysis. The solvent was removed in vacuum. The crude product was subjected to column chromatography on silica gel (100–200 mesh) using petroleum ether-ethylacetate (7:3) as the eluent. Compound was recrystallized from methanol.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen atoms are omited for clarity.

(3aR,9 bS)-3-(4-Chlorophenyl)-1-methyl-1,2,3,3a,4,9 b- hexahydrochromeno[4,3-b]pyrrole-3a-carbonitrile top

Crystal data top

C₁₉H₁₇ClN₂O	F(000) = 680
M_r = 324.80	D_x = 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 = 1.7–25.0°
b = 7.6009 (3) Å	µ = 0.24 mm⁻¹
c = 24.2026 (10) Å	T = 294 K
β = 97.701 (1)°	Prism, colourless
V = 1616.27 (12) Å³	0.28 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker APEX2 kappa diffractometer	5199 independent reflections
Radiation source: fine-focus sealed tube	3858 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
φ and ω scans	θ_max = 31.2°, θ_min = 1.7°
Absorption correction: multi-scan (Blessing, 1995)	h = −12→11
T_min = 0.935, T_max = 0.953	k = −10→11
21338 measured reflections	l = −35→35

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0639P)² + 0.427P] where P = (F_o² + 2F_c²)/3
5199 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.29 e Å⁻³
2 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₉H₁₇ClN₂O	V = 1616.27 (12) Å³
M_r = 324.80	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8659 (4) Å	µ = 0.24 mm⁻¹
b = 7.6009 (3) Å	T = 294 K
c = 24.2026 (10) Å	0.28 × 0.20 × 0.20 mm
β = 97.701 (1)°

Data collection top

Bruker APEX2 kappa diffractometer	5199 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	3858 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.953	R_int = 0.020
21338 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	2 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
5199 reflections	Δρ_min = −0.29 e Å⁻³
208 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇ClN₂O
M_r	324.80
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	8.8659 (4), 7.6009 (3), 24.2026 (10)
β (°)	97.701 (1)
V (Å³)	1616.27 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.28 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEX2 kappa diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.935, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	21338, 5199, 3858
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.728

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.138, 1.04
No. of reflections	5199
No. of parameters	208
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.29

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

C2—N1	1.4610 (18)	C16—Cl1	1.7423 (14)
C5—O1	1.4197 (17)	C19—N2	1.1368 (19)
C6—O1	1.3700 (18)	C20—N1	1.454 (2)
C12—N1	1.4662 (17)

C6—O1—C5	114.84 (10)	O1—C6—C7	116.14 (12)
C20—N1—C2	112.77 (11)	N1—C12—C11	115.81 (10)
C20—N1—C12	115.08 (13)	N1—C12—C4	100.84 (10)
C2—N1—C12	103.02 (10)	C17—C16—Cl1	119.66 (12)
N1—C2—C3	104.05 (11)	C15—C16—Cl1	119.18 (12)
O1—C5—C4	112.18 (11)	N2—C19—C4	177.88 (17)
O1—C6—C11	123.13 (11)

Acknowledgements

SN thanks Professor M. N. Ponnuswamy, Department of Crystallography and Biophysics, University of Madras, India, for his guidance and valuable suggestions. SN thanks SRM management, India, for their support.

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