3-(4-Chloro­phen­yl)-7-methyl-4-(4-methyl­phen­yl)-1-oxa-2,7-diaza­spiro­[4.5]dec-2-en-10-one

Gayathri, D.; Velmurugan, D.; Ranjith Kumar, R.; Perumal, S.; Ravikumar, K.

doi:10.1107/S1600536807068717

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o398

doi:10.1107/S1600536807068717

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3-(4-Chlorophenyl)-7-methyl-4-(4-methylphenyl)-1-oxa-2,7-diazaspiro[4.5]dec-2-en-10-one

D. Gayathri,^a D. Velmurugan,^a ^* R. Ranjith Kumar,^b S. Perumal ^b and K. Ravikumar ^c

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India
^*Correspondence e-mail: d_velu@yahoo.com

(Received 10 December 2007; accepted 29 December 2007; online 9 January 2008)

In the title compound, C₂₁H₂₁ClN₂O₂, the dihydroisoxazole ring adopts an envelope conformation and the piperidinone ring is in a chair conformation. The dihedral angle between the two benzene rings is 84.2 (1)°. The crystal used was an inversion twin.

Related literature

For general background, see: Diana et al. (1985 ); Huisgen (1984 ); Lepage et al. (1992 ); Ryng et al. (1998 ); Torssell (1988 ). For puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Nardelli (1983 ).

Experimental

Crystal data

C₂₁H₂₁ClN₂O₂
M_r = 368.85
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.4585 (8) Å
b = 16.1132 (11) Å
c = 10.1038 (7) Å
V = 1865.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 (2) K
0.24 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: none
16236 measured reflections
4350 independent reflections
3771 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.111
S = 1.03
4350 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), with 1846 Friedel pairs
Flack parameter: 0.65 (6)

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068717/ci2543sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068717/ci2543Isup2.hkl

checkCIF report

Comment top

1,3-Dipolar cycloaddition of nitrile oxides to alkenes and alkynes affords isoxazoles and isoxazolines (Torssell, 1988). Apart from exhibiting important biological activities such as antiviral (Diana et al., 1985), anticonvulsant (Lepage et al., 1992) and immunostimulatory (Ryng et al., 1998), isoxazolines are valuable synthons in the synthesis of α,β-unsaturated ketones, β-hydroxy ketones and γ-amino alcohols (Huisgen, 1984). In view of the above facts, we have undertaken the X-ray crystal structure determination of the title compound.

The sum of the bond angles around N2 (331.7°) indicates the sp³-hybridization. The dihydro-isoxazole ring (C1—C3/O1/N1) adopts an envelope conformation with atom C1 deviating by 0.350 (2) Å from the plane of rest of the atoms in the ring. The piperidinone ring adopts a chair conformation. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for the dihydro-isoxazole ring are q₂ = 0.220 (2) Å, ϕ = 142.2 (4)° and Δ_s(C₁) = 1.1 (2)°, and for the piperidinone ring q₂ = 0.074 (2) Å, q₃ = 0.569 (2) Å, Q_T = 0.574 (2) Å and θ = 7.5 (2)°. The dihedral angle between the two benzene rings (C9—C14 and C16—C21) is 84.2 (1)°. The chlorine atom deviates by -0.065 (1) Å from the plane of the attached C16—C21 benzene ring, and the methyl carbon atom C15 deviates by 0.082 (2) Å from the plane of the C9—C14 benzene ring.

The crystal packing is stabilized by van der Waals forces.

Related literature top

For general background, see: Diana et al. (1985); Huisgen (1984); Lepage et al. (1992); Ryng et al. (1998); Torssell (1988). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983).

Experimental top

To a well stirred mixture of 1-methyl-3-[(E)-4-methylphenylmethylidene]tetrahydro-4(1H)-pyridinone (1 mmol) and 4-chlorobenzohydroximoyl chloride (3 mmol) in benzene (15 ml), triethylamine (3 mmol) was added dropwise over a period of 10 min and stirring was continued for 5 h at ambient temperature. The triethylamine hydrochloride was filtered off, solvent evaporated in vacuo, and the product was purified by column chromatography using petroleum ether-ethyl acetate (4:1 v/v) mixture. The compound was then recrystallized from ethanol-ethyl acetate (1:1 v/v).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound viewed down the c axis.

3-(4-Chlorophenyl)-7-methyl-4-(4-methylphenyl)-1-oxa-2,7- diazaspiro[4.5]dec-2-en-10-one top

Crystal data top

C₂₁H₂₁ClN₂O₂	F(000) = 776
M_r = 368.85	D_x = 1.313 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2169 reflections
a = 11.4585 (8) Å	θ = 2.2–25.0°
b = 16.1132 (11) Å	µ = 0.22 mm⁻¹
c = 10.1038 (7) Å	T = 293 K
V = 1865.5 (2) Å³	Block, colourless
Z = 4	0.24 × 0.23 × 0.20 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3771 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 28.0°, θ_min = 2.2°
ω scans	h = −14→14
16236 measured reflections	k = −20→20
4350 independent reflections	l = −12→13

Refinement top

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0709P)² + 0.0494P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4350 reflections	Δρ_max = 0.24 e Å⁻³
238 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Absolute structure: Flack (1983); 1846 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.65 (6)

Crystal data top

C₂₁H₂₁ClN₂O₂	V = 1865.5 (2) Å³
M_r = 368.85	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.4585 (8) Å	µ = 0.22 mm⁻¹
b = 16.1132 (11) Å	T = 293 K
c = 10.1038 (7) Å	0.24 × 0.23 × 0.20 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3771 reflections with I > 2σ(I)
16236 measured reflections	R_int = 0.022
4350 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.111	Δρ_max = 0.24 e Å⁻³
S = 1.04	Δρ_min = −0.16 e Å⁻³
4350 reflections	Absolute structure: Flack (1983); 1846 Friedel pairs
238 parameters	Absolute structure parameter: 0.65 (6)
0 restraints

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
C1	0.39999 (14)	0.21740 (10)	0.26025 (16)	0.0441 (4)
C2	0.47545 (14)	0.14014 (10)	0.28375 (16)	0.0432 (4)
H2	0.5027	0.1400	0.3757	0.052*
C3	0.57576 (15)	0.16160 (10)	0.19396 (17)	0.0451 (4)
C4	0.26874 (15)	0.20376 (11)	0.2506 (2)	0.0498 (4)
H4A	0.2523	0.1668	0.1771	0.060*
H4B	0.2414	0.1772	0.3310	0.060*
C5	0.2264 (2)	0.33753 (12)	0.3408 (2)	0.0643 (6)
H5A	0.2049	0.3109	0.4233	0.077*
H5B	0.1784	0.3866	0.3301	0.077*
C6	0.3552 (2)	0.36245 (12)	0.3452 (3)	0.0666 (6)
H6A	0.3773	0.3897	0.2633	0.080*
H6B	0.3691	0.4005	0.4179	0.080*
C7	0.42530 (17)	0.28489 (11)	0.36367 (19)	0.0516 (4)
C8	0.08128 (17)	0.26456 (16)	0.2160 (2)	0.0703 (6)
H8A	0.0523	0.2374	0.2939	0.106*
H8B	0.0692	0.2295	0.1405	0.106*
H8C	0.0404	0.3160	0.2035	0.106*
C9	0.42089 (13)	0.05732 (10)	0.25237 (16)	0.0422 (3)
C10	0.40319 (16)	0.03083 (11)	0.12336 (18)	0.0510 (4)
H10	0.4296	0.0634	0.0535	0.061*
C11	0.34703 (17)	−0.04313 (12)	0.0970 (2)	0.0567 (5)
H11	0.3365	−0.0596	0.0096	0.068*
C12	0.30606 (15)	−0.09324 (11)	0.1981 (2)	0.0535 (4)
C13	0.32650 (18)	−0.06790 (12)	0.3258 (2)	0.0590 (5)
H13	0.3018	−0.1012	0.3955	0.071*
C14	0.38319 (16)	0.00627 (11)	0.35339 (18)	0.0520 (4)
H14	0.3959	0.0217	0.4409	0.062*
C15	0.2395 (2)	−0.17151 (13)	0.1691 (3)	0.0755 (7)
H15A	0.2165	−0.1972	0.2507	0.113*
H15B	0.2882	−0.2090	0.1199	0.113*
H15C	0.1713	−0.1584	0.1180	0.113*
C16	0.69030 (15)	0.12007 (10)	0.19526 (18)	0.0453 (4)
C17	0.77102 (16)	0.13329 (12)	0.09496 (19)	0.0522 (4)
H17	0.7506	0.1654	0.0221	0.063*
C18	0.88106 (17)	0.09925 (12)	0.1024 (2)	0.0559 (4)
H18	0.9347	0.1079	0.0347	0.067*
C19	0.91083 (15)	0.05239 (11)	0.2108 (2)	0.0526 (4)
C20	0.83202 (17)	0.03571 (11)	0.30978 (19)	0.0559 (5)
H20	0.8526	0.0022	0.3810	0.067*
C21	0.72139 (17)	0.06986 (12)	0.30132 (19)	0.0527 (4)
H21	0.6671	0.0590	0.3676	0.063*
N1	0.55545 (14)	0.22078 (9)	0.11384 (15)	0.0530 (4)
N2	0.20607 (14)	0.28110 (9)	0.23159 (16)	0.0548 (4)
O1	0.44115 (11)	0.25059 (8)	0.13460 (12)	0.0552 (3)
O2	0.49219 (14)	0.27449 (9)	0.45270 (15)	0.0714 (4)
Cl1	1.05097 (4)	0.01181 (4)	0.22360 (6)	0.07411 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0457 (8)	0.0424 (8)	0.0441 (9)	0.0017 (7)	0.0011 (7)	0.0028 (6)
C2	0.0438 (8)	0.0449 (8)	0.0410 (8)	0.0035 (6)	−0.0025 (7)	0.0023 (7)
C3	0.0428 (8)	0.0451 (8)	0.0476 (9)	−0.0007 (7)	−0.0009 (7)	−0.0016 (7)
C4	0.0457 (8)	0.0503 (9)	0.0532 (10)	0.0026 (7)	−0.0022 (8)	0.0016 (8)
C5	0.0689 (13)	0.0495 (10)	0.0744 (14)	0.0179 (9)	0.0117 (11)	0.0037 (9)
C6	0.0768 (14)	0.0425 (9)	0.0805 (14)	0.0026 (9)	0.0013 (12)	−0.0085 (9)
C7	0.0498 (10)	0.0469 (9)	0.0580 (10)	−0.0047 (7)	0.0042 (9)	0.0014 (8)
C8	0.0503 (10)	0.0856 (14)	0.0751 (13)	0.0143 (10)	0.0057 (10)	0.0159 (12)
C9	0.0379 (7)	0.0420 (8)	0.0467 (9)	0.0046 (6)	0.0004 (7)	0.0029 (6)
C10	0.0549 (10)	0.0498 (9)	0.0482 (9)	0.0000 (8)	0.0031 (8)	0.0028 (7)
C11	0.0554 (10)	0.0553 (11)	0.0595 (11)	0.0033 (8)	−0.0044 (9)	−0.0067 (9)
C12	0.0407 (8)	0.0428 (9)	0.0769 (13)	0.0073 (7)	−0.0018 (9)	−0.0003 (8)
C13	0.0582 (11)	0.0477 (9)	0.0710 (13)	0.0022 (9)	0.0080 (9)	0.0151 (9)
C14	0.0563 (10)	0.0509 (9)	0.0489 (9)	0.0031 (8)	0.0013 (8)	0.0037 (8)
C15	0.0590 (12)	0.0509 (11)	0.116 (2)	−0.0032 (9)	−0.0063 (13)	−0.0041 (12)
C16	0.0425 (8)	0.0422 (8)	0.0510 (9)	−0.0008 (7)	−0.0021 (7)	−0.0060 (7)
C17	0.0485 (9)	0.0548 (10)	0.0534 (10)	0.0006 (8)	0.0014 (8)	0.0024 (8)
C18	0.0465 (9)	0.0619 (11)	0.0594 (11)	0.0015 (8)	0.0070 (9)	−0.0020 (9)
C19	0.0428 (8)	0.0517 (9)	0.0634 (11)	0.0056 (7)	−0.0035 (8)	−0.0114 (8)
C20	0.0586 (11)	0.0551 (10)	0.0541 (10)	0.0111 (8)	−0.0027 (9)	0.0004 (8)
C21	0.0505 (9)	0.0547 (10)	0.0527 (10)	0.0035 (8)	0.0059 (8)	0.0000 (8)
N1	0.0471 (8)	0.0580 (9)	0.0540 (8)	0.0063 (7)	0.0061 (7)	0.0053 (7)
N2	0.0495 (8)	0.0569 (9)	0.0580 (9)	0.0087 (7)	0.0036 (7)	0.0104 (7)
O1	0.0519 (7)	0.0619 (7)	0.0519 (6)	0.0132 (6)	0.0056 (6)	0.0146 (6)
O2	0.0826 (11)	0.0639 (9)	0.0678 (9)	−0.0015 (8)	−0.0190 (8)	−0.0105 (7)
Cl1	0.0503 (3)	0.0879 (4)	0.0841 (4)	0.0210 (2)	−0.0020 (2)	−0.0061 (3)

Geometric parameters (Å, º) top

C1—O1	1.456 (2)	C9—C10	1.386 (2)
C1—C4	1.523 (2)	C10—C11	1.380 (3)
C1—C2	1.534 (2)	C10—H10	0.93
C1—C7	1.536 (2)	C11—C12	1.384 (3)
C2—C3	1.505 (2)	C11—H11	0.93
C2—C9	1.507 (2)	C12—C13	1.374 (3)
C2—H2	0.98	C12—C15	1.503 (3)
C3—N1	1.272 (2)	C13—C14	1.389 (3)
C3—C16	1.473 (2)	C13—H13	0.93
C4—N2	1.451 (2)	C14—H14	0.93
C4—H4A	0.97	C15—H15A	0.96
C4—H4B	0.97	C15—H15B	0.96
C5—N2	1.448 (3)	C15—H15C	0.96
C5—C6	1.530 (3)	C16—C17	1.388 (3)
C5—H5A	0.97	C16—C21	1.389 (3)
C5—H5B	0.97	C17—C18	1.377 (3)
C6—C7	1.497 (3)	C17—H17	0.93
C6—H6A	0.97	C18—C19	1.373 (3)
C6—H6B	0.97	C18—H18	0.93
C7—O2	1.194 (2)	C19—C20	1.374 (3)
C8—N2	1.463 (3)	C19—Cl1	1.7386 (17)
C8—H8A	0.96	C20—C21	1.385 (3)
C8—H8B	0.96	C20—H20	0.93
C8—H8C	0.96	C21—H21	0.93
C9—C14	1.380 (2)	N1—O1	1.411 (2)

O1—C1—C4	108.48 (14)	C11—C10—C9	121.03 (17)
O1—C1—C2	104.50 (13)	C11—C10—H10	119.5
C4—C1—C2	116.71 (14)	C9—C10—H10	119.5
O1—C1—C7	105.78 (13)	C10—C11—C12	121.29 (19)
C4—C1—C7	109.40 (14)	C10—C11—H11	119.4
C2—C1—C7	111.27 (14)	C12—C11—H11	119.4
C3—C2—C9	113.17 (14)	C13—C12—C11	117.52 (17)
C3—C2—C1	98.68 (13)	C13—C12—C15	121.3 (2)
C9—C2—C1	116.88 (13)	C11—C12—C15	121.2 (2)
C3—C2—H2	109.2	C12—C13—C14	121.60 (18)
C9—C2—H2	109.2	C12—C13—H13	119.2
C1—C2—H2	109.2	C14—C13—H13	119.2
N1—C3—C16	120.60 (16)	C9—C14—C13	120.73 (17)
N1—C3—C2	114.59 (15)	C9—C14—H14	119.6
C16—C3—C2	124.81 (14)	C13—C14—H14	119.6
N2—C4—C1	111.92 (15)	C12—C15—H15A	109.5
N2—C4—H4A	109.2	C12—C15—H15B	109.5
C1—C4—H4A	109.2	H15A—C15—H15B	109.5
N2—C4—H4B	109.2	C12—C15—H15C	109.5
C1—C4—H4B	109.2	H15A—C15—H15C	109.5
H4A—C4—H4B	107.9	H15B—C15—H15C	109.5
N2—C5—C6	110.03 (17)	C17—C16—C21	118.79 (16)
N2—C5—H5A	109.7	C17—C16—C3	121.15 (16)
C6—C5—H5A	109.7	C21—C16—C3	119.99 (16)
N2—C5—H5B	109.7	C18—C17—C16	120.60 (18)
C6—C5—H5B	109.7	C18—C17—H17	119.7
H5A—C5—H5B	108.2	C16—C17—H17	119.7
C7—C6—C5	107.56 (16)	C19—C18—C17	119.33 (18)
C7—C6—H6A	110.2	C19—C18—H18	120.3
C5—C6—H6A	110.2	C17—C18—H18	120.3
C7—C6—H6B	110.2	C18—C19—C20	121.66 (16)
C5—C6—H6B	110.2	C18—C19—Cl1	119.72 (15)
H6A—C6—H6B	108.5	C20—C19—Cl1	118.62 (15)
O2—C7—C6	123.75 (19)	C19—C20—C21	118.62 (17)
O2—C7—C1	122.32 (16)	C19—C20—H20	120.7
C6—C7—C1	113.88 (17)	C21—C20—H20	120.7
N2—C8—H8A	109.5	C20—C21—C16	120.92 (17)
N2—C8—H8B	109.5	C20—C21—H21	119.5
H8A—C8—H8B	109.5	C16—C21—H21	119.5
N2—C8—H8C	109.5	C3—N1—O1	109.30 (14)
H8A—C8—H8C	109.5	C5—N2—C4	111.01 (15)
H8B—C8—H8C	109.5	C5—N2—C8	110.72 (16)
C14—C9—C10	117.78 (16)	C4—N2—C8	109.97 (16)
C14—C9—C2	120.12 (15)	N1—O1—C1	107.77 (12)
C10—C9—C2	122.07 (15)

O1—C1—C2—C3	20.69 (15)	C10—C11—C12—C15	176.79 (18)
C4—C1—C2—C3	140.47 (15)	C11—C12—C13—C14	1.8 (3)
C7—C1—C2—C3	−93.02 (15)	C15—C12—C13—C14	−176.97 (18)
O1—C1—C2—C9	−100.88 (16)	C10—C9—C14—C13	−1.8 (3)
C4—C1—C2—C9	18.9 (2)	C2—C9—C14—C13	176.12 (16)
C7—C1—C2—C9	145.41 (15)	C12—C13—C14—C9	0.1 (3)
C9—C2—C3—N1	110.31 (17)	N1—C3—C16—C17	−11.9 (3)
C1—C2—C3—N1	−13.93 (19)	C2—C3—C16—C17	168.66 (16)
C9—C2—C3—C16	−70.2 (2)	N1—C3—C16—C21	164.90 (17)
C1—C2—C3—C16	165.53 (15)	C2—C3—C16—C21	−14.5 (3)
O1—C1—C4—N2	−63.77 (19)	C21—C16—C17—C18	−1.9 (3)
C2—C1—C4—N2	178.61 (15)	C3—C16—C17—C18	174.95 (17)
C7—C1—C4—N2	51.2 (2)	C16—C17—C18—C19	−0.5 (3)
N2—C5—C6—C7	−60.1 (2)	C17—C18—C19—C20	2.7 (3)
C5—C6—C7—O2	−123.4 (2)	C17—C18—C19—Cl1	−178.00 (15)
C5—C6—C7—C1	54.2 (2)	C18—C19—C20—C21	−2.4 (3)
O1—C1—C7—O2	−115.9 (2)	Cl1—C19—C20—C21	178.29 (14)
C4—C1—C7—O2	127.43 (19)	C19—C20—C21—C16	−0.1 (3)
C2—C1—C7—O2	−3.0 (2)	C17—C16—C21—C20	2.2 (3)
O1—C1—C7—C6	66.42 (19)	C3—C16—C21—C20	−174.70 (17)
C4—C1—C7—C6	−50.2 (2)	C16—C3—N1—O1	−178.78 (14)
C2—C1—C7—C6	179.33 (16)	C2—C3—N1—O1	0.7 (2)
C3—C2—C9—C14	141.75 (16)	C6—C5—N2—C4	64.4 (2)
C1—C2—C9—C14	−104.61 (18)	C6—C5—N2—C8	−173.13 (17)
C3—C2—C9—C10	−40.4 (2)	C1—C4—N2—C5	−60.1 (2)
C1—C2—C9—C10	73.2 (2)	C1—C4—N2—C8	177.08 (16)
C14—C9—C10—C11	1.6 (3)	C3—N1—O1—C1	14.11 (18)
C2—C9—C10—C11	−176.26 (16)	C4—C1—O1—N1	−147.46 (14)
C9—C10—C11—C12	0.3 (3)	C2—C1—O1—N1	−22.29 (16)
C10—C11—C12—C13	−2.0 (3)	C7—C1—O1—N1	95.25 (15)

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁ClN₂O₂
M_r	368.85
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	11.4585 (8), 16.1132 (11), 10.1038 (7)
V (Å³)	1865.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.24 × 0.23 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16236, 4350, 3771
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.111, 1.04
No. of reflections	4350
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.16
Absolute structure	Flack (1983); 1846 Friedel pairs
Absolute structure parameter	0.65 (6)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Acknowledgements

DG thanks the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship. The University Grants Commission (UGC–SAP) and the Department of Science and Technology (DST–FIST), Government of India, are acknowledged by DV for providing facilities to the department.

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