3-(3-Chloro­phen­yl)-1-methyl-3,3a,4,9b-tetra­hydro-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile

Swaminathan, K.; Sethusankar, K.; Murugan, G.; Bakthadoss, M.

doi:10.1107/S1600536811007495

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o799

doi:10.1107/S1600536811007495

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3-(3-Chlorophenyl)-1-methyl-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile

K. Swaminathan,^a K. Sethusankar,^a ^* G. Murugan ^b and M. Bakthadoss ^b

^aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 31 January 2011; accepted 28 February 2011; online 5 March 2011)

In the title compound, C₁₈H₁₅ClN₂O₂, the five-membered isoxazole ring adopts an envelope conformation [the deviation of the N atom is 0.3154 (15) Å] and the six-membered pyran ring adopts a half-chair conformation. The mean plane through all atoms of the isoxazole ring forms dihedral angles of 47.98 (8)° with the mean plane of the chromene ring system and 75.10 (9)° with the chlorobenzene ring.

Related literature

For the synthesis of tricyclic chromenoisoxazolidines, see: Bakthadoss & Murugan (2010 ). For uses of isoxazole derivatives, see: Loh et al. (2010 ); Winn et al. (1976 ). For a related structure, see: Gunasekaran et al. (2010 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₈H₁₅ClN₂O₂
M_r = 326.77
Monoclinic, P 2₁ /c
a = 10.0141 (4) Å
b = 9.2358 (3) Å
c = 17.5945 (6) Å
β = 102.354 (2)°
V = 1589.60 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.928, T_max = 0.952
20534 measured reflections
4926 independent reflections
3390 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.151
S = 1.04
4926 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007495/rk2265sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007495/rk2265Isup2.hkl

checkCIF report

Comment top

Using Baylis-Hillman derivatives through in situ formation of nitrones followed by an intramolecular [3+2] dipolar cycloaddition reaction sequence is a novel and simple method of synthesizing tricyclic chromenoisoxozolidine frameworks. The new [3+2] cycloaddition reaction leads to a novel class of angularly substituted fused tricyclic chromenoisoxazolidines, creating two rings and three contiguous stereocenters, one of them being a tetrasubstituted carbon center. (Bakthadoss & Murugan, 2010). Benzopyran and isoxazolidine derivatives are well known for their biological activity and proven medicinal utility. For example, benzopyran derivatives possess antipsychotic and antidepressant activities (Winn et al., 1976). Isoxazolidine and isoxazole sulfonamide are found to inhibit HIV-1 infection in human CD4+ lymphocytic T cells (Loh et al., 2010).

The title compound C₁₈H₁₅N₂O₂Cl comprises a chromenoisoxazole ring system attached to a chlorobenzene ring and a carbonitrile group. The X-ray analysis confirms the molecular structure and atom connectivity as illustrated at (Fig. 1). In the isoxazole ring (N1/O2/C7/C8/C10), the deviation of atom N1 is -0.3154 (15)Å. This ring adopts an envelope conformation with puckering parameters (Cremer & Pople, 1975) q₂ = 0.5041 (15)Å and ϕ₂ = 44.23 (17)°. The dihedral angle between the chromeno ring system (O1/C1–C9) and the isoxazole ring(N1/O2/C7/C8/C10) is 47.98 (8)°. The isoxazole ring (N1/O2/C7/C8/C10) also forms a dihedral angle of 75.10 (9)° with the the chlorobenzene ring (C11–C16).

In the chromeno ring system, the dihedral angle between the pyran ring (O1/C1/C6-C9) and the benzene ring(C1-C6) is 3.50 (9)°. The deviation of atom C9 from the mean plane of the pyran ring is 0.3068 (17)Å. The pyran ring adopts half chair conformation (H-form), with puckering parameters (Cremer & Pople, 1975) q₂ = 0.3501 (17)Å, q₃ = -0.3037 (16)Å and ϕ₂ = 94.7 (2)°. The pyran ring (O1/C1/C6–C9) also forms an interplanar angle of 49.31 (8)° with the isoxazole ring (N1/O2/C7/C8/C10). The chlorobenzene ring(C11–C16) forms an interplanar angle of 51.98 (8)° with the mean plane of the fused isoxazole–pyran ring system (N1/O1/O2/C1/C6–C10). Also, the dihedral angle between the chlorobenzene ring (C11–C16) and the chromeno ring system (O1/C1–C9) is 39.95 (7)°. The title compound exhibits structural similarities with other reported related structures (Gunasekaran et al., 2010). There are no classic hydrogen bonds.

Related literature top

For he synthesis of tricyclic chromenoisoxazolidines, see: Bakthadoss & Murugan (2010). For uses of isoxazole derivatives, see: Loh et al. (2010); Winn et al. (1976). For a related structure, see: Gunasekaran et al. (2010). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of the compound (E)-2-((2-formylphenoxy) methyl)-3-(3-chlorophenyl) acrylonitrile (1.0 mmol) with N-methylhydroxylamine hydrochloride (1.1 mmol), pyridine (0.24 ml, 3 mmol) and ethanol (5 ml) were placed in a round bottom flask and refluxed for 6 h. After completion of the reaction as indicated by TLC, the reaction mixture was concentrated under reduced pressure. The crude product was diluted with water (10 ml) and dilute HCl (5 ml) and extracted with ethylacetate (20 ml). The organic layer was washed with brine solution (10 ml) and concentrated. The crude product was purified by column chromatography to provide the pure desired compound, as a colourless solid.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitary radius.

3-(3-Chlorophenyl)-1-methyl-3,3a,4,9b-tetrahydro-1H- chromeno[4,3-c]isoxazole-3a-carbonitrile top

Crystal data top

C₁₈H₁₅ClN₂O₂	F(000) = 680
M_r = 326.77	D_x = 1.365 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4926 reflections
a = 10.0141 (4) Å	θ = 1.0–25.0°
b = 9.2358 (3) Å	µ = 0.25 mm⁻¹
c = 17.5945 (6) Å	T = 295 K
β = 102.354 (2)°	Block, colourless
V = 1589.60 (10) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4926 independent reflections
Radiation source: fine-focus sealed tube	3390 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 30.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
T_min = 0.928, T_max = 0.952	k = −13→12
20534 measured reflections	l = −25→25

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0641P)² + 0.525P] where P = (F_o² + 2F_c²)/3
4926 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₁₈H₁₅ClN₂O₂	V = 1589.60 (10) Å³
M_r = 326.77	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0141 (4) Å	µ = 0.25 mm⁻¹
b = 9.2358 (3) Å	T = 295 K
c = 17.5945 (6) Å	0.30 × 0.25 × 0.20 mm
β = 102.354 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4926 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3390 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.952	R_int = 0.026
20534 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.04	Δρ_max = 0.61 e Å⁻³
4926 reflections	Δρ_min = −0.63 e Å⁻³
209 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.71130 (16)	0.55309 (17)	0.60426 (9)	0.0414 (3)
C2	0.7392 (2)	0.5485 (2)	0.53022 (11)	0.0558 (5)
H2	0.6764	0.5081	0.4890	0.067*
C3	0.8604 (2)	0.6042 (3)	0.51838 (13)	0.0661 (6)
H3	0.8786	0.6031	0.4687	0.079*
C4	0.9552 (2)	0.6618 (3)	0.57932 (14)	0.0666 (6)
H4	1.0375	0.6980	0.5710	0.080*
C5	0.92754 (19)	0.6654 (2)	0.65242 (12)	0.0527 (4)
H5	0.9924	0.7029	0.6936	0.063*
C6	0.80402 (15)	0.61383 (17)	0.66604 (9)	0.0391 (3)
C7	0.77527 (14)	0.61740 (15)	0.74613 (8)	0.0347 (3)
H7	0.8576	0.5912	0.7847	0.042*
C8	0.65603 (14)	0.51912 (15)	0.75457 (8)	0.0345 (3)
C9	0.54349 (15)	0.53043 (18)	0.68020 (9)	0.0400 (3)
H9A	0.4677	0.4683	0.6851	0.048*
H9B	0.5100	0.6292	0.6743	0.048*
C10	0.60629 (16)	0.58987 (17)	0.82461 (9)	0.0392 (3)
H10	0.5095	0.6157	0.8079	0.047*
C11	0.62489 (15)	0.49933 (17)	0.89708 (9)	0.0382 (3)
C12	0.74430 (16)	0.50552 (19)	0.95373 (10)	0.0435 (4)
H12	0.8145	0.5681	0.9483	0.052*
C13	0.75772 (19)	0.4174 (2)	1.01837 (10)	0.0503 (4)
C14	0.6564 (2)	0.3247 (2)	1.02857 (12)	0.0584 (5)
H14	0.6676	0.2664	1.0726	0.070*
C15	0.5385 (2)	0.3195 (2)	0.97269 (12)	0.0621 (5)
H15	0.4687	0.2569	0.9788	0.075*
C16	0.52159 (19)	0.4062 (2)	0.90713 (11)	0.0512 (4)
H16	0.4406	0.4020	0.8697	0.061*
C17	0.8261 (2)	0.86941 (19)	0.78734 (11)	0.0531 (4)
H17A	0.7878	0.9520	0.8080	0.080*
H17B	0.8582	0.8975	0.7418	0.080*
H17C	0.9010	0.8321	0.8257	0.080*
C18	0.69897 (16)	0.36725 (17)	0.76710 (10)	0.0405 (3)
N1	0.72137 (14)	0.75768 (14)	0.76661 (7)	0.0396 (3)
N2	0.72938 (17)	0.24949 (17)	0.77403 (11)	0.0618 (4)
O1	0.59142 (12)	0.48990 (13)	0.61273 (7)	0.0470 (3)
O2	0.68515 (14)	0.71908 (12)	0.84078 (7)	0.0481 (3)
Cl1	0.90798 (6)	0.42666 (9)	1.08998 (4)	0.0900 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0467 (8)	0.0382 (8)	0.0375 (8)	0.0095 (6)	0.0049 (6)	−0.0010 (6)
C2	0.0680 (12)	0.0572 (11)	0.0404 (9)	0.0170 (9)	0.0079 (8)	−0.0024 (8)
C3	0.0852 (14)	0.0674 (13)	0.0533 (11)	0.0204 (11)	0.0318 (11)	0.0081 (10)
C4	0.0685 (12)	0.0649 (13)	0.0749 (14)	0.0032 (10)	0.0344 (11)	0.0058 (11)
C5	0.0475 (9)	0.0522 (10)	0.0595 (11)	−0.0014 (8)	0.0142 (8)	−0.0013 (8)
C6	0.0402 (7)	0.0350 (7)	0.0406 (8)	0.0046 (6)	0.0055 (6)	0.0011 (6)
C7	0.0346 (6)	0.0300 (7)	0.0355 (7)	0.0006 (5)	−0.0015 (5)	−0.0001 (5)
C8	0.0353 (7)	0.0285 (6)	0.0369 (7)	0.0029 (5)	0.0016 (5)	−0.0002 (5)
C9	0.0341 (7)	0.0415 (8)	0.0406 (8)	0.0013 (6)	−0.0007 (6)	−0.0047 (6)
C10	0.0401 (7)	0.0358 (7)	0.0402 (8)	0.0050 (6)	0.0053 (6)	−0.0013 (6)
C11	0.0402 (7)	0.0351 (7)	0.0404 (8)	0.0004 (6)	0.0111 (6)	−0.0026 (6)
C12	0.0395 (7)	0.0456 (9)	0.0454 (8)	−0.0006 (7)	0.0091 (6)	0.0074 (7)
C13	0.0550 (10)	0.0499 (10)	0.0453 (9)	0.0078 (8)	0.0091 (7)	0.0076 (7)
C14	0.0899 (14)	0.0380 (9)	0.0523 (10)	−0.0021 (9)	0.0262 (10)	0.0051 (8)
C15	0.0824 (14)	0.0455 (10)	0.0662 (12)	−0.0269 (10)	0.0331 (11)	−0.0089 (9)
C16	0.0518 (9)	0.0503 (10)	0.0517 (10)	−0.0143 (8)	0.0119 (8)	−0.0137 (8)
C17	0.0676 (11)	0.0342 (8)	0.0540 (10)	−0.0085 (8)	0.0052 (8)	−0.0031 (7)
C18	0.0404 (7)	0.0326 (7)	0.0471 (8)	0.0010 (6)	0.0061 (6)	0.0004 (6)
N1	0.0513 (7)	0.0293 (6)	0.0360 (6)	0.0008 (5)	0.0045 (5)	0.0011 (5)
N2	0.0636 (10)	0.0364 (8)	0.0845 (12)	0.0068 (7)	0.0135 (9)	0.0031 (8)
O1	0.0452 (6)	0.0517 (7)	0.0392 (6)	−0.0014 (5)	−0.0016 (5)	−0.0116 (5)
O2	0.0751 (8)	0.0314 (6)	0.0395 (6)	−0.0028 (5)	0.0158 (5)	−0.0031 (4)
Cl1	0.0704 (4)	0.1252 (6)	0.0635 (4)	0.0115 (4)	−0.0098 (3)	0.0284 (3)

Geometric parameters (Å, º) top

C1—O1	1.371 (2)	C10—O2	1.4257 (19)
C1—C6	1.388 (2)	C10—C11	1.503 (2)
C1—C2	1.390 (2)	C10—H10	0.9800
C2—C3	1.375 (3)	C11—C12	1.384 (2)
C2—H2	0.9300	C11—C16	1.385 (2)
C3—C4	1.378 (3)	C12—C13	1.381 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.373 (3)	C13—C14	1.369 (3)
C4—H4	0.9300	C13—Cl1	1.7459 (19)
C5—C6	1.393 (2)	C14—C15	1.366 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.498 (2)	C15—C16	1.385 (3)
C7—N1	1.4775 (19)	C15—H15	0.9300
C7—C8	1.532 (2)	C16—H16	0.9300
C7—H7	0.9800	C17—N1	1.461 (2)
C8—C18	1.470 (2)	C17—H17A	0.9600
C8—C9	1.537 (2)	C17—H17B	0.9600
C8—C10	1.567 (2)	C17—H17C	0.9600
C9—O1	1.423 (2)	C18—N2	1.129 (2)
C9—H9A	0.9700	N1—O2	1.4711 (17)
C9—H9B	0.9700

O1—C1—C6	122.77 (14)	O2—C10—C11	109.49 (12)
O1—C1—C2	116.42 (15)	O2—C10—C8	104.48 (12)
C6—C1—C2	120.75 (17)	C11—C10—C8	115.63 (12)
C3—C2—C1	119.44 (19)	O2—C10—H10	109.0
C3—C2—H2	120.3	C11—C10—H10	109.0
C1—C2—H2	120.3	C8—C10—H10	109.0
C2—C3—C4	120.68 (19)	C12—C11—C16	119.17 (16)
C2—C3—H3	119.7	C12—C11—C10	121.27 (14)
C4—C3—H3	119.7	C16—C11—C10	119.56 (15)
C5—C4—C3	119.7 (2)	C13—C12—C11	119.03 (16)
C5—C4—H4	120.2	C13—C12—H12	120.5
C3—C4—H4	120.2	C11—C12—H12	120.5
C4—C5—C6	121.15 (19)	C14—C13—C12	122.17 (17)
C4—C5—H5	119.4	C14—C13—Cl1	118.99 (15)
C6—C5—H5	119.4	C12—C13—Cl1	118.84 (14)
C1—C6—C5	118.25 (16)	C15—C14—C13	118.59 (17)
C1—C6—C7	120.97 (14)	C15—C14—H14	120.7
C5—C6—C7	120.71 (15)	C13—C14—H14	120.7
N1—C7—C6	113.74 (12)	C14—C15—C16	120.76 (17)
N1—C7—C8	99.38 (11)	C14—C15—H15	119.6
C6—C7—C8	112.88 (12)	C16—C15—H15	119.6
N1—C7—H7	110.1	C15—C16—C11	120.27 (17)
C6—C7—H7	110.1	C15—C16—H16	119.9
C8—C7—H7	110.1	C11—C16—H16	119.9
C18—C8—C7	111.76 (12)	N1—C17—H17A	109.5
C18—C8—C9	109.29 (12)	N1—C17—H17B	109.5
C7—C8—C9	108.78 (12)	H17A—C17—H17B	109.5
C18—C8—C10	114.32 (13)	N1—C17—H17C	109.5
C7—C8—C10	102.39 (11)	H17A—C17—H17C	109.5
C9—C8—C10	110.04 (12)	H17B—C17—H17C	109.5
O1—C9—C8	112.07 (12)	N2—C18—C8	177.46 (19)
O1—C9—H9A	109.2	C17—N1—O2	104.46 (12)
C8—C9—H9A	109.2	C17—N1—C7	113.60 (13)
O1—C9—H9B	109.2	O2—N1—C7	100.14 (10)
C8—C9—H9B	109.2	C1—O1—C9	115.99 (12)
H9A—C9—H9B	107.9	C10—O2—N1	104.90 (11)

O1—C1—C2—C3	−177.20 (17)	C7—C8—C10—C11	−114.23 (14)
C6—C1—C2—C3	0.3 (3)	C9—C8—C10—C11	130.25 (14)
C1—C2—C3—C4	1.3 (3)	O2—C10—C11—C12	−28.6 (2)
C2—C3—C4—C5	−0.9 (3)	C8—C10—C11—C12	89.10 (18)
C3—C4—C5—C6	−1.0 (3)	O2—C10—C11—C16	152.35 (14)
O1—C1—C6—C5	175.18 (15)	C8—C10—C11—C16	−89.99 (18)
C2—C1—C6—C5	−2.2 (2)	C16—C11—C12—C13	0.7 (2)
O1—C1—C6—C7	−1.9 (2)	C10—C11—C12—C13	−178.38 (15)
C2—C1—C6—C7	−179.23 (15)	C11—C12—C13—C14	−0.4 (3)
C4—C5—C6—C1	2.5 (3)	C11—C12—C13—Cl1	−179.51 (13)
C4—C5—C6—C7	179.59 (17)	C12—C13—C14—C15	0.1 (3)
C1—C6—C7—N1	−98.81 (17)	Cl1—C13—C14—C15	179.19 (15)
C5—C6—C7—N1	84.21 (18)	C13—C14—C15—C16	−0.1 (3)
C1—C6—C7—C8	13.4 (2)	C14—C15—C16—C11	0.4 (3)
C5—C6—C7—C8	−163.53 (14)	C12—C11—C16—C15	−0.7 (3)
N1—C7—C8—C18	−158.11 (12)	C10—C11—C16—C15	178.42 (16)
C6—C7—C8—C18	81.06 (15)	C6—C7—N1—C17	−77.41 (16)
N1—C7—C8—C9	81.13 (13)	C8—C7—N1—C17	162.38 (12)
C6—C7—C8—C9	−39.70 (16)	C6—C7—N1—O2	171.80 (12)
N1—C7—C8—C10	−35.30 (13)	C8—C7—N1—O2	51.59 (12)
C6—C7—C8—C10	−156.14 (12)	C6—C1—O1—C9	20.4 (2)
C18—C8—C9—O1	−63.51 (17)	C2—C1—O1—C9	−162.18 (15)
C7—C8—C9—O1	58.76 (16)	C8—C9—O1—C1	−49.34 (18)
C10—C8—C9—O1	170.19 (12)	C11—C10—O2—N1	150.44 (12)
C18—C8—C10—O2	127.25 (13)	C8—C10—O2—N1	26.01 (14)
C7—C8—C10—O2	6.19 (14)	C17—N1—O2—C10	−167.72 (13)
C9—C8—C10—O2	−109.34 (13)	C7—N1—O2—C10	−49.94 (13)
C18—C8—C10—C11	6.83 (18)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅ClN₂O₂
M_r	326.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.0141 (4), 9.2358 (3), 17.5945 (6)
β (°)	102.354 (2)
V (Å³)	1589.60 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.928, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	20534, 4926, 3390
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.718

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.151, 1.04
No. of reflections	4926
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.63

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

KSN and KS thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray data collection.

References

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