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

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

doi:10.1107/S1600536808030985

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2041

doi:10.1107/S1600536808030985

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1-Chloroacetyl-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, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 17 September 2008; accepted 25 September 2008; online 30 September 2008)

In the molecule of the title compound, C₂₁H₂₂ClNO₂, the piperidine ring adopts a distorted boat conformation. The two phenyl rings are nearly orthogonal to each other with a dihedral angle of 87.1 (1)°. In the crystal structure, the molecules are linked into a three-dimensional network by C—H⋯O and C—H⋯π interactions.

Related literature

For general background, see: Dimmock et al. (2001 ); Perumal et al. (2001 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₁H₂₂ClNO₂
M_r = 355.85
Monoclinic, P 2₁ /n
a = 13.7005 (3) Å
b = 9.8735 (2) Å
c = 14.8960 (3) Å
β = 112.762 (1)°
V = 1858.08 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 (2) K
0.32 × 0.26 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.854, T_max = 0.958
22063 measured reflections
4674 independent reflections
3424 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.154
S = 1.01
4674 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.98	2.46	3.426 (2)	168
C8—H8B⋯O2ⁱ	0.97	2.53	3.495 (3)	172
C21—H21⋯O1ⁱⁱ	0.93	2.53	3.248 (3)	134
C11—H11⋯Cg1ⁱⁱⁱ	0.93	2.73	3.568 (2)	150
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z+1.

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, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030985/ci2675sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030985/ci2675Isup2.hkl

checkCIF report

Comment top

Piperidones are the important group of heterocyclic compounds in the field of medicinal chemistry due to their biological activities, including cytotoxic properties (Dimmock et al., 2001). They were also reported to possess analgesic, anti-inflammatory, central nervous system (CNS), local anaesthetic, anticancer and antimicrobial activities (Perumal et al., 2001).

The sum of bond angles around N1 atom (359.4°) indicates sp² hybridization. The N1—C7 [1.360 (2) Å] and C7—O2 [1.220 (2) Å] distances indicate electron delocalization. The piperidine ring adopts a distorted boat conformation, confirmed by puckering parameters q₂ = 0.612 (2) Å, q₃ = -0.122 (2) Å and ϕ ₂ = 258.0 (2)° (Cremer & Pople, 1975) and the asymmetry parameter Δ_s(C2) = Δ_s(C5) = 19.2 (2)° (Nardelli, 1983). The two phenyl rings are nearly orthogonal to each other with a dihedral angle of 87.1 (1)°. The methyl substituents are oriented equatorially [N1—C2—C3—C16 = 175.3 (2)°] and axially [N1—C2—C3—C15 = 55.1 (2)°] at C3 position.

The crystal structure is stabilized by C—H···O and C—H···π intermolecular interactions. The glide-related molecules are linked into a chain along the b axis by C6—H6···O2ⁱ and C8—H8B···O2ⁱ hydrogen bonds, and the chains are cross-linked via C21—H21···O1ⁱⁱ hydrogen bonds; symmetry codes are given in Table 1. In addition, C—H···π interactions involving the C17–C22 ring (centroid Cg1) are observed.

Related literature top

For general background, see: Dimmock et al. (2001); Perumal et al. (2001). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

A mixture of 3,3-dimethyl-cis-2,6-diphenylpiperidin-4-one (1.4 g, 5 mmol), chloro acetylchloride (0.8 ml, 5 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 to obtain a pasty mass. It was purified by crystallization from benzene–petroleum ether (95:5, 60–80°C).

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, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 20% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Dashed lines indicate hydrogen bonds. H atoms not involed in hydrogen bonding have been omitted.

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

Crystal data top

C₂₁H₂₂ClNO₂	F(000) = 752
M_r = 355.85	D_x = 1.272 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4674 reflections
a = 13.7005 (3) Å	θ = 2.5–28.5°
b = 9.8735 (2) Å	µ = 0.22 mm⁻¹
c = 14.8960 (3) Å	T = 293 K
β = 112.762 (1)°	Block, colourless
V = 1858.08 (7) Å³	0.32 × 0.26 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII area-detector diffractometer	4674 independent reflections
Radiation source: fine-focus sealed tube	3424 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and ϕ scans	θ_max = 28.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −18→18
T_min = 0.854, T_max = 0.958	k = −11→13
22063 measured reflections	l = −18→19

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0741P)² + 0.7704P] where P = (F_o² + 2F_c²)/3
4674 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

C₂₁H₂₂ClNO₂	V = 1858.08 (7) Å³
M_r = 355.85	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.7005 (3) Å	µ = 0.22 mm⁻¹
b = 9.8735 (2) Å	T = 293 K
c = 14.8960 (3) Å	0.32 × 0.26 × 0.20 mm
β = 112.762 (1)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	4674 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3424 reflections with I > 2σ(I)
T_min = 0.854, T_max = 0.958	R_int = 0.025
22063 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.01	Δρ_max = 0.68 e Å⁻³
4674 reflections	Δρ_min = −0.66 e Å⁻³
226 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	0.20338 (13)	0.74492 (17)	0.41291 (11)	0.0364 (3)
H2	0.2263	0.8253	0.3878	0.044*
C3	0.30126 (14)	0.6958 (2)	0.50015 (13)	0.0457 (4)
C4	0.27691 (14)	0.56295 (19)	0.53752 (13)	0.0460 (4)
C5	0.19260 (15)	0.47683 (18)	0.46543 (13)	0.0450 (4)
H5A	0.1275	0.4912	0.4755	0.054*
H5B	0.2125	0.3828	0.4808	0.054*
C6	0.16822 (13)	0.49786 (17)	0.35689 (12)	0.0374 (3)
H6	0.2216	0.4486	0.3411	0.045*
C7	0.16925 (13)	0.68513 (18)	0.24518 (12)	0.0392 (4)
C8	0.15274 (18)	0.5752 (2)	0.16986 (14)	0.0536 (5)
H8A	0.0834	0.5350	0.1537	0.064*
H8B	0.2053	0.5048	0.1972	0.064*
C9	0.10539 (13)	0.78759 (16)	0.43001 (11)	0.0372 (3)
C10	0.08432 (16)	0.75494 (19)	0.51136 (13)	0.0462 (4)
H10	0.1339	0.7062	0.5620	0.055*
C11	−0.00972 (18)	0.7942 (2)	0.51791 (15)	0.0547 (5)
H11	−0.0225	0.7717	0.5730	0.066*
C12	−0.08371 (17)	0.8654 (2)	0.44463 (16)	0.0569 (5)
H12	−0.1470	0.8906	0.4493	0.068*
C13	−0.06398 (16)	0.8999 (2)	0.36330 (15)	0.0558 (5)
H13	−0.1139	0.9490	0.3132	0.067*
C14	0.02930 (15)	0.86157 (19)	0.35629 (13)	0.0451 (4)
H14	0.0418	0.8855	0.3013	0.054*
C15	0.39135 (16)	0.6647 (3)	0.46568 (19)	0.0695 (7)
H15A	0.4103	0.7459	0.4409	0.104*
H15B	0.3681	0.5975	0.4152	0.104*
H15C	0.4517	0.6313	0.5194	0.104*
C16	0.33953 (19)	0.8035 (2)	0.58046 (15)	0.0635 (6)
H16A	0.3542	0.8862	0.5541	0.095*
H16B	0.4028	0.7724	0.6321	0.095*
H16C	0.2856	0.8194	0.6054	0.095*
C17	0.06144 (13)	0.43346 (18)	0.30018 (12)	0.0402 (4)
C18	−0.03188 (15)	0.4922 (2)	0.29576 (15)	0.0514 (5)
H18	−0.0308	0.5772	0.3230	0.062*
C19	−0.12687 (16)	0.4244 (3)	0.25075 (18)	0.0653 (6)
H19	−0.1896	0.4643	0.2477	0.078*
C20	−0.12916 (18)	0.2988 (3)	0.21055 (17)	0.0672 (6)
H20	−0.1932	0.2534	0.1810	0.081*
C21	−0.0373 (2)	0.2404 (2)	0.21401 (17)	0.0645 (6)
H21	−0.0389	0.1556	0.1862	0.077*
C22	0.05803 (17)	0.3072 (2)	0.25877 (14)	0.0517 (5)
H22	0.1203	0.2669	0.2611	0.062*
Cl1	0.16240 (6)	0.63835 (7)	0.06314 (4)	0.0778 (2)
N1	0.17457 (10)	0.64277 (14)	0.33383 (9)	0.0350 (3)
O1	0.32116 (13)	0.52655 (16)	0.62105 (10)	0.0706 (5)
O2	0.17704 (12)	0.80385 (14)	0.22634 (10)	0.0518 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0408 (8)	0.0334 (8)	0.0325 (8)	−0.0040 (6)	0.0113 (6)	0.0006 (6)
C3	0.0407 (8)	0.0456 (10)	0.0409 (9)	−0.0039 (7)	0.0049 (7)	0.0007 (7)
C4	0.0477 (9)	0.0416 (10)	0.0396 (9)	0.0071 (8)	0.0070 (7)	0.0041 (7)
C5	0.0533 (10)	0.0358 (9)	0.0399 (9)	−0.0014 (7)	0.0114 (8)	0.0063 (7)
C6	0.0398 (8)	0.0331 (8)	0.0384 (8)	−0.0020 (6)	0.0143 (7)	0.0000 (6)
C7	0.0394 (8)	0.0433 (10)	0.0375 (8)	−0.0005 (7)	0.0177 (7)	0.0022 (7)
C8	0.0761 (13)	0.0507 (11)	0.0404 (9)	0.0006 (10)	0.0295 (9)	0.0007 (8)
C9	0.0452 (8)	0.0321 (8)	0.0328 (8)	−0.0034 (7)	0.0136 (6)	−0.0017 (6)
C10	0.0599 (10)	0.0423 (10)	0.0382 (9)	−0.0002 (8)	0.0210 (8)	0.0036 (7)
C11	0.0692 (12)	0.0547 (12)	0.0506 (11)	−0.0083 (10)	0.0346 (10)	−0.0026 (9)
C12	0.0509 (10)	0.0616 (13)	0.0633 (13)	−0.0042 (9)	0.0278 (10)	−0.0119 (10)
C13	0.0501 (10)	0.0628 (13)	0.0487 (11)	0.0097 (9)	0.0127 (8)	−0.0009 (9)
C14	0.0521 (10)	0.0471 (10)	0.0356 (8)	0.0046 (8)	0.0164 (7)	0.0025 (7)
C15	0.0394 (10)	0.0911 (18)	0.0705 (15)	0.0000 (10)	0.0129 (10)	0.0047 (13)
C16	0.0668 (13)	0.0553 (12)	0.0468 (11)	−0.0150 (10)	−0.0016 (9)	−0.0027 (9)
C17	0.0453 (9)	0.0390 (9)	0.0351 (8)	−0.0074 (7)	0.0144 (7)	0.0031 (7)
C18	0.0458 (9)	0.0456 (10)	0.0566 (11)	−0.0039 (8)	0.0129 (8)	0.0041 (9)
C19	0.0424 (10)	0.0691 (15)	0.0728 (15)	−0.0048 (10)	0.0096 (10)	0.0161 (12)
C20	0.0586 (12)	0.0710 (15)	0.0568 (12)	−0.0287 (11)	0.0057 (10)	0.0037 (11)
C21	0.0760 (15)	0.0581 (13)	0.0567 (12)	−0.0258 (11)	0.0225 (11)	−0.0140 (10)
C22	0.0605 (11)	0.0497 (11)	0.0489 (10)	−0.0143 (9)	0.0256 (9)	−0.0101 (8)
Cl1	0.1234 (6)	0.0747 (4)	0.0530 (3)	−0.0077 (4)	0.0534 (4)	−0.0031 (3)
N1	0.0387 (7)	0.0337 (7)	0.0327 (7)	−0.0025 (5)	0.0139 (5)	0.0002 (5)
O1	0.0861 (11)	0.0565 (9)	0.0427 (8)	0.0064 (8)	−0.0041 (7)	0.0112 (7)
O2	0.0714 (9)	0.0441 (7)	0.0471 (7)	−0.0043 (6)	0.0308 (7)	0.0057 (6)

Geometric parameters (Å, º) top

C2—N1	1.483 (2)	C11—C12	1.363 (3)
C2—C9	1.520 (2)	C11—H11	0.93
C2—C3	1.541 (2)	C12—C13	1.382 (3)
C2—H2	0.98	C12—H12	0.93
C3—C4	1.512 (3)	C13—C14	1.375 (3)
C3—C16	1.534 (3)	C13—H13	0.93
C3—C15	1.540 (3)	C14—H14	0.93
C4—O1	1.209 (2)	C15—H15A	0.96
C4—C5	1.500 (3)	C15—H15B	0.96
C5—C6	1.533 (2)	C15—H15C	0.96
C5—H5A	0.97	C16—H16A	0.96
C5—H5B	0.97	C16—H16B	0.96
C6—N1	1.482 (2)	C16—H16C	0.96
C6—C17	1.517 (2)	C17—C18	1.382 (3)
C6—H6	0.98	C17—C22	1.384 (3)
C7—O2	1.220 (2)	C18—C19	1.384 (3)
C7—N1	1.360 (2)	C18—H18	0.93
C7—C8	1.514 (3)	C19—C20	1.372 (4)
C8—Cl1	1.7595 (19)	C19—H19	0.93
C8—H8A	0.97	C20—C21	1.367 (4)
C8—H8B	0.97	C20—H20	0.93
C9—C10	1.388 (2)	C21—C22	1.382 (3)
C9—C14	1.393 (2)	C21—H21	0.93
C10—C11	1.385 (3)	C22—H22	0.93
C10—H10	0.93

N1—C2—C9	109.92 (12)	C10—C11—H11	119.6
N1—C2—C3	109.45 (14)	C11—C12—C13	119.48 (19)
C9—C2—C3	118.87 (14)	C11—C12—H12	120.3
N1—C2—H2	105.9	C13—C12—H12	120.3
C9—C2—H2	105.9	C14—C13—C12	120.11 (19)
C3—C2—H2	105.9	C14—C13—H13	119.9
C4—C3—C16	111.85 (16)	C12—C13—H13	119.9
C4—C3—C15	105.63 (18)	C13—C14—C9	121.22 (18)
C16—C3—C15	108.79 (18)	C13—C14—H14	119.4
C4—C3—C2	109.86 (14)	C9—C14—H14	119.4
C16—C3—C2	111.27 (16)	C3—C15—H15A	109.5
C15—C3—C2	109.26 (16)	C3—C15—H15B	109.5
O1—C4—C5	120.59 (18)	H15A—C15—H15B	109.5
O1—C4—C3	122.87 (17)	C3—C15—H15C	109.5
C5—C4—C3	116.54 (15)	H15A—C15—H15C	109.5
C4—C5—C6	118.12 (15)	H15B—C15—H15C	109.5
C4—C5—H5A	107.8	C3—C16—H16A	109.5
C6—C5—H5A	107.8	C3—C16—H16B	109.5
C4—C5—H5B	107.8	H16A—C16—H16B	109.5
C6—C5—H5B	107.8	C3—C16—H16C	109.5
H5A—C5—H5B	107.1	H16A—C16—H16C	109.5
N1—C6—C17	113.96 (13)	H16B—C16—H16C	109.5
N1—C6—C5	111.52 (14)	C18—C17—C22	119.07 (17)
C17—C6—C5	107.46 (13)	C18—C17—C6	121.70 (16)
N1—C6—H6	107.9	C22—C17—C6	119.00 (16)
C17—C6—H6	107.9	C17—C18—C19	119.9 (2)
C5—C6—H6	107.9	C17—C18—H18	120.0
O2—C7—N1	122.85 (16)	C19—C18—H18	120.0
O2—C7—C8	121.32 (16)	C20—C19—C18	120.4 (2)
N1—C7—C8	115.83 (15)	C20—C19—H19	119.8
C7—C8—Cl1	111.96 (14)	C18—C19—H19	119.8
C7—C8—H8A	109.2	C21—C20—C19	120.0 (2)
Cl1—C8—H8A	109.2	C21—C20—H20	120.0
C7—C8—H8B	109.2	C19—C20—H20	120.0
Cl1—C8—H8B	109.2	C20—C21—C22	120.1 (2)
H8A—C8—H8B	107.9	C20—C21—H21	120.0
C10—C9—C14	117.72 (16)	C22—C21—H21	120.0
C10—C9—C2	125.29 (15)	C21—C22—C17	120.5 (2)
C14—C9—C2	116.96 (15)	C21—C22—H22	119.8
C11—C10—C9	120.67 (18)	C17—C22—H22	119.8
C11—C10—H10	119.7	C7—N1—C6	122.42 (14)
C9—C10—H10	119.7	C7—N1—C2	117.37 (13)
C12—C11—C10	120.80 (18)	C6—N1—C2	119.59 (13)
C12—C11—H11	119.6

N1—C2—C3—C4	−60.29 (18)	C12—C13—C14—C9	0.2 (3)
C9—C2—C3—C4	67.1 (2)	C10—C9—C14—C13	−0.6 (3)
N1—C2—C3—C16	175.29 (15)	C2—C9—C14—C13	177.27 (17)
C9—C2—C3—C16	−57.3 (2)	N1—C6—C17—C18	−50.6 (2)
N1—C2—C3—C15	55.1 (2)	C5—C6—C17—C18	73.5 (2)
C9—C2—C3—C15	−177.45 (17)	N1—C6—C17—C22	134.95 (16)
C16—C3—C4—O1	−28.9 (3)	C5—C6—C17—C22	−100.95 (19)
C15—C3—C4—O1	89.3 (2)	C22—C17—C18—C19	0.3 (3)
C2—C3—C4—O1	−153.0 (2)	C6—C17—C18—C19	−174.15 (18)
C16—C3—C4—C5	150.31 (18)	C17—C18—C19—C20	0.2 (3)
C15—C3—C4—C5	−91.50 (19)	C18—C19—C20—C21	−0.6 (4)
C2—C3—C4—C5	26.2 (2)	C19—C20—C21—C22	0.6 (4)
O1—C4—C5—C6	−157.96 (19)	C20—C21—C22—C17	−0.2 (3)
C3—C4—C5—C6	22.8 (2)	C18—C17—C22—C21	−0.3 (3)
C4—C5—C6—N1	−37.4 (2)	C6—C17—C22—C21	174.29 (18)
C4—C5—C6—C17	−162.92 (16)	O2—C7—N1—C6	−178.13 (16)
O2—C7—C8—Cl1	7.0 (2)	C8—C7—N1—C6	1.9 (2)
N1—C7—C8—Cl1	−173.12 (13)	O2—C7—N1—C2	−7.2 (2)
N1—C2—C9—C10	109.58 (18)	C8—C7—N1—C2	172.90 (15)
C3—C2—C9—C10	−17.6 (2)	C17—C6—N1—C7	−66.5 (2)
N1—C2—C9—C14	−68.14 (18)	C5—C6—N1—C7	171.59 (15)
C3—C2—C9—C14	164.68 (16)	C17—C6—N1—C2	122.72 (15)
C14—C9—C10—C11	0.5 (3)	C5—C6—N1—C2	0.8 (2)
C2—C9—C10—C11	−177.24 (17)	C9—C2—N1—C7	104.00 (16)
C9—C10—C11—C12	0.2 (3)	C3—C2—N1—C7	−123.72 (15)
C10—C11—C12—C13	−0.6 (3)	C9—C2—N1—C6	−84.78 (17)
C11—C12—C13—C14	0.5 (3)	C3—C2—N1—C6	47.50 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.98	2.46	3.426 (2)	168
C8—H8B···O2ⁱ	0.97	2.53	3.495 (3)	172
C21—H21···O1ⁱⁱ	0.93	2.53	3.248 (3)	134
C11—H11···Cg1ⁱⁱⁱ	0.93	2.73	3.568 (2)	150

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂ClNO₂
M_r	355.85
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.7005 (3), 9.8735 (2), 14.8960 (3)
β (°)	112.762 (1)
V (Å³)	1858.08 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.32 × 0.26 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.854, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	22063, 4674, 3424
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.154, 1.01
No. of reflections	4674
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.66

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.98	2.46	3.426 (2)	168
C8—H8B···O2ⁱ	0.97	2.53	3.495 (3)	172
C21—H21···O1ⁱⁱ	0.93	2.53	3.248 (3)	134
C11—H11···Cg1ⁱⁱⁱ	0.93	2.73	3.568 (2)	150

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −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 UGC, India, for financial support.

References

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