1-Dichloro­acetyl-3,3-dimethyl-2,6-diphenyl­piperidin-4-one

Kavitha, T.; Ponnuswamy, S.; Jamesh, M.; Umamaheshwari, J.; Ponnuswamy, M.N.

doi:10.1107/S1600536808040051

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o10

doi:10.1107/S1600536808040051

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1-Dichloroacetyl-3,3-dimethyl-2,6-diphenylpiperidin-4-one

T. Kavitha,^a S. Ponnuswamy,^b M. Jamesh,^b J. Umamaheshwari ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, Tamil Nadu, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 14 November 2008; accepted 27 November 2008; online 3 December 2008)

In the title compound, C₂₁H₂₁Cl₂NO₂, the piperidine ring adopts a distorted boat conformation. The two phenyl rings are approximately perpendicular to each other, with a dihedral angle of 86.12 (7)°. Molecules are linked into centrosymmetric dimers by pairs of bifurcated C—H⋯O hydrogen bonds, forming R₂²(10) and R₂²(14) ring motifs, and an intramolecular C—H⋯O link also occurs.

Related literature

For general backround, see: Ponnuswamy et al. (2002 ). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring puckering and asymmetry parameters, see: Cremer & Pople (1975 ); Nardelli (1983 ). For hybridization, see: Beddoes et al. (1986 ).

Experimental

Crystal data

C₂₁H₂₁Cl₂NO₂
M_r = 390.29
Triclinic, $[P \overline 1]$
a = 9.1084 (2) Å
b = 10.8992 (3) Å
c = 10.9918 (3) Å
α = 63.879 (1)°
β = 85.343 (2)°
γ = 79.029 (1)°
V = 961.84 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 293 (2) K
0.30 × 0.26 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.902, T_max = 0.933
26977 measured reflections
7709 independent reflections
5516 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.180
S = 1.03
7709 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2	0.93	2.57	3.250 (2)	130
C2—H2⋯O2ⁱ	0.98	2.50	3.4264 (18)	158
C16—H16A⋯O2ⁱ	0.96	2.54	3.413 (2)	151
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; 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: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040051/ci2724sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040051/ci2724Isup2.hkl

checkCIF report

Comment top

The design and synthesis of conformationally anchored molecules are important due its potency and selectivity for designing drugs. The piperidin-4-ones are one such class of compounds to be investigated to understand the stereodynamics and other structural features (Ponnuswamy et al., 2002).

The sum of bond angles around atom N1 (359.6°) indicates sp² hybridization (Beddoes et al., 1986). The N1—C7 [1.3564 (16) Å] and C7—O2 [1.2149 (17) Å] distances indicate electron delocalization. The piperidine ring adopts a distorted boat conformation, with puckering parameters (Cremer & Pople, 1975) q2 = 0.638 (1) Å, q3 = -0.067 (2) Å and ϕ₂ = 253.4 (1)°, and the asymmetry parameters ΔC_s(C2)= 14.4 (1)° (Nardelli, 1983). The best plane through the piperidine ring, N1/C3/C4/C6, forms dihedral angles of 89.31 (6)° and 63.47 (7)°, respectively, with the C9—C4 and C17—C22 phenyl rings. The two phenyl rings are approximately perpendicular to each other, with a dihedral angle of 86.12 (7)°.

The crystal structure is stabilized by intermolecular C—H···O hydrogen bonds. Each atoms C2 and C16 at (x, y, z) donate one proton to bifurcated acceptor O2 at (-x, 1 - y, 1 - z), forming a centrosymmetric dimer (Fig. 2) with R₂²(10) and R₂²(14) ring motifs (Bernstein et al., 1995).

Related literature top

For general backround, see: Ponnuswamy et al. (2002). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For ring puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983). For hybridization, see: Beddoes et al. (1986).

Experimental top

A mixture of 3,3-dimethyl-cis-2,6-diphenylpiperidin-4-one (1.4 g, 5 mmol), dichloroacetylchloride (1 ml, 10 mmol) and triethylamine (2 ml, 14.4 mmol) in anhydrous benzene (20 ml) was stirred at room temperature for 7 h. The benzene solution was dried over anhydrous Na₂SO₄ and concentrated. The pasty mass obtained was purified by crystallization from benzene-petroleum ether (333–353 K) in the ratio of 95:5.

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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of the title compound, showing hydrogen-bonded (dashed lines) dimers. Atom H16A and H atoms not involved in hydrogen bonding have been omitted.

1-Dichloroacetyl-3,3-dimethyl-2,6-diphenylpiperidin-4-one top

Crystal data top

C₂₁H₂₁Cl₂NO₂	Z = 2
M_r = 390.29	F(000) = 408
Triclinic, P1	D_x = 1.348 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1084 (2) Å	Cell parameters from 7709 reflections
b = 10.8992 (3) Å	θ = 2.1–34.0°
c = 10.9918 (3) Å	µ = 0.35 mm⁻¹
α = 63.879 (1)°	T = 293 K
β = 85.343 (2)°	Block, colourless
γ = 79.029 (1)°	0.30 × 0.26 × 0.20 mm
V = 961.84 (4) Å³

Data collection top

Bruker Kappa APEXII area-detector diffractometer	7709 independent reflections
Radiation source: fine-focus sealed tube	5516 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω and ϕ scans	θ_max = 34.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −14→14
T_min = 0.902, T_max = 0.933	k = −16→17
26977 measured reflections	l = −17→15

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0854P)² + 0.3205P] where P = (F_o² + 2F_c²)/3
7709 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.80 e Å⁻³
0 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

C₂₁H₂₁Cl₂NO₂	γ = 79.029 (1)°
M_r = 390.29	V = 961.84 (4) Å³
Triclinic, P1	Z = 2
a = 9.1084 (2) Å	Mo Kα radiation
b = 10.8992 (3) Å	µ = 0.35 mm⁻¹
c = 10.9918 (3) Å	T = 293 K
α = 63.879 (1)°	0.30 × 0.26 × 0.20 mm
β = 85.343 (2)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	7709 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	5516 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.933	R_int = 0.021
26977 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.04	Δρ_max = 0.80 e Å⁻³
7709 reflections	Δρ_min = −0.73 e Å⁻³
235 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
C2	0.16315 (15)	0.26040 (13)	0.64530 (13)	0.0320 (2)
H2	0.1059	0.3371	0.5691	0.038*
C3	0.07185 (16)	0.14160 (15)	0.69561 (15)	0.0363 (3)
C4	0.12824 (17)	0.02567 (15)	0.83179 (16)	0.0394 (3)
C5	0.22508 (18)	0.06135 (14)	0.91179 (15)	0.0392 (3)
H5A	0.3283	0.0437	0.8854	0.047*
H5B	0.2169	−0.0007	1.0070	0.047*
C6	0.18871 (15)	0.21096 (13)	0.89554 (13)	0.0315 (2)
H6	0.0976	0.2204	0.9469	0.038*
C7	0.11626 (15)	0.44855 (13)	0.71233 (13)	0.0330 (2)
C8	0.06652 (16)	0.49415 (14)	0.82515 (15)	0.0369 (3)
H8	0.1194	0.4282	0.9094	0.044*
C9	0.32045 (16)	0.23856 (15)	0.59084 (14)	0.0362 (3)
C10	0.4137 (2)	0.11132 (19)	0.62714 (19)	0.0521 (4)
H10	0.3796	0.0306	0.6872	0.062*
C11	0.5572 (2)	0.1029 (3)	0.5750 (2)	0.0641 (5)
H11	0.6186	0.0167	0.6012	0.077*
C12	0.6095 (2)	0.2197 (3)	0.4854 (2)	0.0646 (5)
H12	0.7062	0.2136	0.4516	0.078*
C13	0.5178 (3)	0.3460 (3)	0.4460 (2)	0.0683 (6)
H13	0.5521	0.4258	0.3842	0.082*
C14	0.3742 (2)	0.35549 (19)	0.49753 (19)	0.0522 (4)
H14	0.3129	0.4419	0.4690	0.063*
C15	0.0667 (2)	0.0880 (2)	0.5892 (2)	0.0554 (4)
H15A	0.0305	0.1640	0.5050	0.083*
H15B	0.0010	0.0210	0.6192	0.083*
H15C	0.1654	0.0452	0.5765	0.083*
C16	−0.09026 (17)	0.19822 (18)	0.72274 (18)	0.0458 (3)
H16A	−0.1334	0.2725	0.6403	0.069*
H16B	−0.0895	0.2320	0.7899	0.069*
H16C	−0.1485	0.1252	0.7549	0.069*
C17	0.31594 (16)	0.23865 (14)	0.95568 (15)	0.0377 (3)
C18	0.4438 (2)	0.2760 (2)	0.8816 (2)	0.0564 (4)
H18	0.4525	0.2854	0.7932	0.068*
C19	0.5588 (3)	0.2993 (3)	0.9398 (3)	0.0812 (8)
H19	0.6448	0.3239	0.8903	0.097*
C20	0.5464 (3)	0.2865 (3)	1.0703 (3)	0.0855 (9)
H20	0.6232	0.3041	1.1080	0.103*
C21	0.4221 (3)	0.2479 (3)	1.1444 (3)	0.0749 (7)
H21	0.4148	0.2384	1.2329	0.090*
C22	0.3049 (2)	0.22256 (19)	1.08834 (19)	0.0523 (4)
H22	0.2206	0.1952	1.1396	0.063*
Cl1	0.09918 (6)	0.66177 (5)	0.78274 (6)	0.06072 (15)
Cl2	−0.12724 (6)	0.49086 (7)	0.84645 (7)	0.07096 (18)
N1	0.16105 (12)	0.31050 (11)	0.75154 (11)	0.0301 (2)
O1	0.09414 (17)	−0.08818 (13)	0.87624 (15)	0.0596 (4)
O2	0.10590 (15)	0.53523 (11)	0.59509 (11)	0.0479 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0360 (6)	0.0327 (5)	0.0303 (5)	−0.0091 (5)	0.0005 (4)	−0.0151 (5)
C3	0.0389 (7)	0.0372 (6)	0.0392 (6)	−0.0133 (5)	0.0001 (5)	−0.0198 (5)
C4	0.0407 (7)	0.0324 (6)	0.0470 (7)	−0.0117 (5)	0.0009 (6)	−0.0170 (5)
C5	0.0463 (7)	0.0291 (6)	0.0386 (7)	−0.0096 (5)	−0.0051 (6)	−0.0094 (5)
C6	0.0327 (6)	0.0314 (5)	0.0299 (5)	−0.0085 (4)	−0.0015 (4)	−0.0113 (4)
C7	0.0356 (6)	0.0300 (5)	0.0337 (6)	−0.0068 (5)	−0.0007 (5)	−0.0134 (5)
C8	0.0397 (7)	0.0334 (6)	0.0399 (7)	−0.0043 (5)	−0.0015 (5)	−0.0186 (5)
C9	0.0390 (7)	0.0403 (6)	0.0343 (6)	−0.0114 (5)	0.0046 (5)	−0.0196 (5)
C10	0.0480 (9)	0.0468 (8)	0.0557 (9)	−0.0050 (7)	0.0120 (7)	−0.0203 (7)
C11	0.0477 (10)	0.0720 (13)	0.0679 (12)	0.0016 (9)	0.0097 (9)	−0.0323 (10)
C12	0.0434 (9)	0.0902 (16)	0.0660 (12)	−0.0188 (10)	0.0178 (8)	−0.0393 (11)
C13	0.0647 (12)	0.0741 (13)	0.0692 (13)	−0.0349 (11)	0.0304 (10)	−0.0298 (11)
C14	0.0571 (10)	0.0460 (8)	0.0521 (9)	−0.0181 (7)	0.0171 (8)	−0.0193 (7)
C15	0.0692 (12)	0.0611 (10)	0.0551 (10)	−0.0264 (9)	0.0026 (8)	−0.0368 (9)
C16	0.0356 (7)	0.0511 (8)	0.0496 (8)	−0.0138 (6)	−0.0013 (6)	−0.0183 (7)
C17	0.0371 (6)	0.0323 (6)	0.0439 (7)	−0.0035 (5)	−0.0108 (5)	−0.0158 (5)
C18	0.0418 (8)	0.0620 (11)	0.0710 (12)	−0.0179 (7)	−0.0038 (8)	−0.0296 (9)
C19	0.0471 (11)	0.0829 (16)	0.128 (2)	−0.0202 (10)	−0.0174 (12)	−0.0520 (16)
C20	0.0652 (14)	0.0734 (14)	0.136 (2)	0.0039 (11)	−0.0552 (16)	−0.0588 (16)
C21	0.0874 (16)	0.0676 (12)	0.0810 (14)	0.0157 (11)	−0.0504 (13)	−0.0454 (11)
C22	0.0588 (10)	0.0522 (9)	0.0486 (9)	0.0007 (7)	−0.0185 (7)	−0.0254 (7)
Cl1	0.0769 (3)	0.0499 (2)	0.0729 (3)	−0.0258 (2)	0.0075 (2)	−0.0378 (2)
Cl2	0.0479 (3)	0.0867 (4)	0.1055 (5)	−0.0242 (2)	0.0255 (3)	−0.0656 (4)
N1	0.0339 (5)	0.0282 (4)	0.0290 (5)	−0.0072 (4)	−0.0003 (4)	−0.0124 (4)
O1	0.0717 (9)	0.0355 (5)	0.0709 (8)	−0.0231 (6)	−0.0097 (7)	−0.0151 (6)
O2	0.0706 (8)	0.0324 (5)	0.0350 (5)	−0.0071 (5)	−0.0009 (5)	−0.0102 (4)

Geometric parameters (Å, º) top

C2—N1	1.4886 (17)	C11—C12	1.367 (3)
C2—C9	1.525 (2)	C11—H11	0.93
C2—C3	1.5424 (19)	C12—C13	1.369 (3)
C2—H2	0.98	C12—H12	0.93
C3—C4	1.521 (2)	C13—C14	1.387 (3)
C3—C15	1.528 (2)	C13—H13	0.93
C3—C16	1.547 (2)	C14—H14	0.93
C4—O1	1.2096 (18)	C15—H15A	0.96
C4—C5	1.503 (2)	C15—H15B	0.96
C5—C6	1.5324 (19)	C15—H15C	0.96
C5—H5A	0.97	C16—H16A	0.96
C5—H5B	0.97	C16—H16B	0.96
C6—N1	1.4814 (16)	C16—H16C	0.96
C6—C17	1.5179 (18)	C17—C18	1.385 (3)
C6—H6	0.98	C17—C22	1.387 (2)
C7—O2	1.2149 (17)	C18—C19	1.387 (3)
C7—N1	1.3564 (16)	C18—H18	0.93
C7—C8	1.535 (2)	C19—C20	1.375 (4)
C8—Cl1	1.7544 (15)	C19—H19	0.93
C8—Cl2	1.7664 (16)	C20—C21	1.361 (4)
C8—H8	0.98	C20—H20	0.93
C9—C14	1.386 (2)	C21—C22	1.401 (3)
C9—C10	1.387 (2)	C21—H21	0.93
C10—C11	1.388 (3)	C22—H22	0.93
C10—H10	0.93

N1—C2—C9	111.62 (11)	C10—C11—H11	119.6
N1—C2—C3	108.79 (10)	C11—C12—C13	119.27 (18)
C9—C2—C3	119.05 (12)	C11—C12—H12	120.4
N1—C2—H2	105.4	C13—C12—H12	120.4
C9—C2—H2	105.4	C12—C13—C14	120.42 (19)
C3—C2—H2	105.4	C12—C13—H13	119.8
C4—C3—C15	112.03 (13)	C14—C13—H13	119.8
C4—C3—C2	111.80 (11)	C9—C14—C13	121.16 (18)
C15—C3—C2	111.26 (13)	C9—C14—H14	119.4
C4—C3—C16	104.84 (12)	C13—C14—H14	119.4
C15—C3—C16	108.17 (14)	C3—C15—H15A	109.5
C2—C3—C16	108.41 (12)	C3—C15—H15B	109.5
O1—C4—C5	121.20 (14)	H15A—C15—H15B	109.5
O1—C4—C3	122.41 (14)	C3—C15—H15C	109.5
C5—C4—C3	116.35 (11)	H15A—C15—H15C	109.5
C4—C5—C6	115.68 (12)	H15B—C15—H15C	109.5
C4—C5—H5A	108.4	C3—C16—H16A	109.5
C6—C5—H5A	108.4	C3—C16—H16B	109.5
C4—C5—H5B	108.4	H16A—C16—H16B	109.5
C6—C5—H5B	108.4	C3—C16—H16C	109.5
H5A—C5—H5B	107.4	H16A—C16—H16C	109.5
N1—C6—C17	112.02 (11)	H16B—C16—H16C	109.5
N1—C6—C5	110.99 (11)	C18—C17—C22	119.73 (16)
C17—C6—C5	108.73 (11)	C18—C17—C6	121.13 (14)
N1—C6—H6	108.3	C22—C17—C6	119.12 (15)
C17—C6—H6	108.3	C17—C18—C19	119.8 (2)
C5—C6—H6	108.3	C17—C18—H18	120.1
O2—C7—N1	124.28 (13)	C19—C18—H18	120.1
O2—C7—C8	119.02 (12)	C20—C19—C18	120.5 (3)
N1—C7—C8	116.59 (11)	C20—C19—H19	119.8
C7—C8—Cl1	111.99 (10)	C18—C19—H19	119.8
C7—C8—Cl2	106.14 (10)	C21—C20—C19	120.06 (19)
Cl1—C8—Cl2	109.75 (8)	C21—C20—H20	120.0
C7—C8—H8	109.6	C19—C20—H20	120.0
Cl1—C8—H8	109.6	C20—C21—C22	120.6 (2)
Cl2—C8—H8	109.6	C20—C21—H21	119.7
C14—C9—C10	117.55 (15)	C22—C21—H21	119.7
C14—C9—C2	117.21 (14)	C17—C22—C21	119.4 (2)
C10—C9—C2	125.24 (13)	C17—C22—H22	120.3
C9—C10—C11	120.81 (18)	C21—C22—H22	120.3
C9—C10—H10	119.6	C7—N1—C6	122.10 (11)
C11—C10—H10	119.6	C7—N1—C2	116.79 (10)
C12—C11—C10	120.7 (2)	C6—N1—C2	120.69 (10)
C12—C11—H11	119.6

N1—C2—C3—C4	−55.28 (15)	C11—C12—C13—C14	0.8 (4)
C9—C2—C3—C4	74.08 (15)	C10—C9—C14—C13	−2.2 (3)
N1—C2—C3—C15	178.63 (13)	C2—C9—C14—C13	177.88 (18)
C9—C2—C3—C15	−52.01 (18)	C12—C13—C14—C9	0.7 (3)
N1—C2—C3—C16	59.80 (14)	N1—C6—C17—C18	−39.86 (19)
C9—C2—C3—C16	−170.84 (12)	C5—C6—C17—C18	83.18 (17)
C15—C3—C4—O1	−38.8 (2)	N1—C6—C17—C22	141.83 (14)
C2—C3—C4—O1	−164.51 (16)	C5—C6—C17—C22	−95.13 (16)
C16—C3—C4—O1	78.24 (19)	C22—C17—C18—C19	−1.1 (3)
C15—C3—C4—C5	143.33 (15)	C6—C17—C18—C19	−179.38 (18)
C2—C3—C4—C5	17.66 (18)	C17—C18—C19—C20	−0.4 (4)
C16—C3—C4—C5	−99.59 (15)	C18—C19—C20—C21	1.3 (4)
O1—C4—C5—C6	−144.98 (16)	C19—C20—C21—C22	−0.7 (4)
C3—C4—C5—C6	32.88 (19)	C18—C17—C22—C21	1.6 (3)
C4—C5—C6—N1	−43.61 (17)	C6—C17—C22—C21	179.98 (15)
C4—C5—C6—C17	−167.26 (13)	C20—C21—C22—C17	−0.7 (3)
O2—C7—C8—Cl1	−33.06 (17)	O2—C7—N1—C6	172.74 (13)
N1—C7—C8—Cl1	150.79 (10)	C8—C7—N1—C6	−11.34 (18)
O2—C7—C8—Cl2	86.69 (15)	O2—C7—N1—C2	−14.7 (2)
N1—C7—C8—Cl2	−89.46 (13)	C8—C7—N1—C2	161.25 (11)
N1—C2—C9—C14	−78.53 (17)	C17—C6—N1—C7	−63.04 (16)
C3—C2—C9—C14	153.41 (15)	C5—C6—N1—C7	175.21 (12)
N1—C2—C9—C10	101.51 (17)	C17—C6—N1—C2	124.65 (13)
C3—C2—C9—C10	−26.6 (2)	C5—C6—N1—C2	2.90 (16)
C14—C9—C10—C11	2.2 (3)	C9—C2—N1—C7	99.87 (13)
C2—C9—C10—C11	−177.88 (17)	C3—C2—N1—C7	−126.77 (12)
C9—C10—C11—C12	−0.7 (3)	C9—C2—N1—C6	−87.43 (14)
C10—C11—C12—C13	−0.8 (4)	C3—C2—N1—C6	45.93 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2	0.93	2.57	3.250 (2)	130
C2—H2···O2ⁱ	0.98	2.50	3.4264 (18)	158
C16—H16A···O2ⁱ	0.96	2.54	3.413 (2)	151

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁Cl₂NO₂
M_r	390.29
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.1084 (2), 10.8992 (3), 10.9918 (3)
α, β, γ (°)	63.879 (1), 85.343 (2), 79.029 (1)
V (Å³)	961.84 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.30 × 0.26 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.902, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	26977, 7709, 5516
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.786

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.180, 1.04
No. of reflections	7709
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.73

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2	0.93	2.57	3.250 (2)	130
C2—H2···O2ⁱ	0.98	2.50	3.4264 (18)	158
C16—H16A···O2ⁱ	0.96	2.54	3.413 (2)	151

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

TK thanks Dr Babu Varghese, SAIF, IIT–Madras, Chennai, India, for his help with the data collection. SP thanks the UGC, India, for financial support.

References

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