Crystal structure of 2-chloro-1-(3-ethyl-2,6-di­phenyl­piperidin-1-yl)ethanone

Shreevidhyaa Suressh, V.; Revathi, B.K.; Abdul Basheer, S.; Ponnuswamy, S.; Usha, G.

doi:10.1107/S2056989015000444

organic compounds

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Volume 71| Part 2| February 2015| Page o122

doi:10.1107/S2056989015000444

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Crystal structure of 2-chloro-1-(3-ethyl-2,6-diphenylpiperidin-1-yl)ethanone

V. Shreevidhyaa Suressh,^a B. K. Revathi,^b S. Abdul Basheer,^c S. Ponnuswamy ^c and G. Usha ^b ^*

^aDepartment of Physics, Anna Adarsh College for Women, Chennai-40, Tamilnadu, India, ^bPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and ^cPG and Research Department of Chemistry, Government Arts College, Coimbatore 18, Tamilnadu, India
^*Correspondence e-mail: guqmc@yahoo.com

Edited by G. Smith, Queensland University of Technology, Australia (Received 15 November 2014; accepted 9 January 2015; online 21 January 2015)

In the racemic title compound, C₂₁H₂₄ClNO, the dihedral angle between the planes of the benzene rings is 86.52 (14)° and those between the benzene rings and the piperidine ring are 61.66 (14) and 86.39 (14)°. The piperidine ring adopts a twisted boat conformation. No directional interactions could be detected in the crystal.

Keywords: crystal structure; 2-chloro-1-(3-ethyl-2,6-diphenylpiperidin-1-yl)ethanone; biological activity; piperidine derivative.

CCDC reference: 1042840

1. Related literature

For the biological activity of piperidine derivatives, see: Nalanishi et al. (1974 ); Robinson (1973 ); Mobio et al. (1989 ); Parthiban et al. (2009 ).

2. Experimental

2.1. Crystal data

C₂₁H₂₄ClNO
M_r = 341.86
Monoclinic, P 2₁ /n
a = 8.5971 (9) Å
b = 12.9080 (13) Å
c = 17.1114 (16) Å
β = 100.501 (5)°
V = 1867.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.23 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.949, T_max = 0.953
17549 measured reflections
4639 independent reflections
2930 reflections with I > 2σ(I)
R_int = 0.027

2.3. Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.226
S = 1.01
4639 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1042840

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015000444/zs2323sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015000444/zs2323Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015000444/zs2323Isup3.cml

checkCIF report

Comment top

Piperidine derivatives have immense biological significance and show blood cholesterol lowering activity (Nalanishi et al., 1974; Parthiban et al., 2009). The piperidine moiety is the basic unit commonly found in natural alkaloids. These compounds are observed to exhibit antihistamine, anaesthetic and tranquilizer activities (Robinson, 1973). They also exhibit antifungal and antibacterial activities (Mobio et al., 1989).

In the stucture of the racemic title compound, C₂₁H₂₄ClNO (Fig. 1) the C—C bond lengths and bond angles are in the normal range and comparable with the literature values. The sum of the bond angles around the nitrogen atom N1 is 359.54 (1)° which indicates sp² hybridization. The benzene ring C4/C5/C6/C7/C8/C9 is bisectionally [59.92 (2)°] attached to the piperidine ring and the benzene ring C14/C15/C16/C17/C18/C19 is axiallly [9.27 (2)°] attached to the piperidine ring. The dihedral angle between the benzene rings is 86.52 (14)° and those between the benzene rings and the piperidine ring are 61.66 (14) and 86.39 (14)°, respectively. The symmetric bond angles [C11—C12—C20 = 107.4 (3) Å and C20—C12—C13 = 110.3 (2) Å] indicate that the ethyl group is coplanar with the piperidine ring. The piperidine ring adopts a twisted boat conformation with puckering parameters of q2 = 0.691 (3) Å, θ2 = 94.4 (2)°, q3 = -0.053 (3) Å, QT = 0.693 (3) Å and smallest asymmetry parameter D2(C3) (Nardelli, 1983) is 0.1078 (1) Å. In the crystal there are no formal hydrogen bonds or inter-ring π–π interactions present (Fig. 2).

Related literature top

For the biological activity of piperidine derivatives, see: Nalanishi et al. (1974); Robinson (1973); Mobio et al. (1989); Parthiban et al. (2009).

Experimental top

A mixture of t-3-methyl-r-2,c-6-diphenylpiperidine (5 mmol), chloroacetyl chloride (20 mmol) and triethylamine (20 mmol) in anhydrous benzene (20 ml) was stirred at room temperature. The precipitated ammonium salt was filtered and the resulting solution was washed with water and bicarbonate solution (4x10 ml). Finally, the benzene solution was dried over anhydrous sodium sulphate and concentrated. The pasty mass was purified by crystallization from a mixture of petroleum ether (60–80 °C) and ethyl acetate in the ratio of 95:5.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008, 2015) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing atom numbering, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing of the molecules in the unit cell.

2-Chloro-1-(3-ethyl-2,6-diphenylpiperidin-1-yl)ethanone top

Crystal data top

C₂₁H₂₄ClNO	F(000) = 728
M_r = 341.86	D_x = 1.216 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4639 reflections
a = 8.5971 (9) Å	θ = 2.0–28.3°
b = 12.9080 (13) Å	µ = 0.21 mm⁻¹
c = 17.1114 (16) Å	T = 293 K
β = 100.501 (5)°	Block, colourless
V = 1867.1 (3) Å³	0.25 × 0.23 × 0.23 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4639 independent reflections
Radiation source: fine-focus sealed tube	2930 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scan	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→11
T_min = 0.949, T_max = 0.953	k = −17→16
17549 measured reflections	l = −22→22

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.226	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.1098P)² + 0.7138P] where P = (F_o² + 2F_c²)/3
4639 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₁H₂₄ClNO	V = 1867.1 (3) Å³
M_r = 341.86	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.5971 (9) Å	µ = 0.21 mm⁻¹
b = 12.9080 (13) Å	T = 293 K
c = 17.1114 (16) Å	0.25 × 0.23 × 0.23 mm
β = 100.501 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4639 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2930 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.953	R_int = 0.027
17549 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.226	H-atom parameters constrained
S = 1.01	Δρ_max = 0.61 e Å⁻³
4639 reflections	Δρ_min = −0.43 e Å⁻³
217 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
C1	0.3154 (3)	0.4581 (2)	0.29469 (14)	0.0637 (6)
C2	0.2091 (3)	0.3683 (2)	0.30518 (16)	0.0740 (7)
H2A	0.1359	0.3886	0.3394	0.089*
H2B	0.2721	0.3109	0.3301	0.089*
C3	0.5246 (3)	0.33072 (17)	0.27780 (13)	0.0581 (5)
H3	0.4458	0.2917	0.2406	0.070*
C4	0.5527 (2)	0.27291 (17)	0.35598 (14)	0.0564 (5)
C5	0.5133 (3)	0.1687 (2)	0.35639 (18)	0.0752 (7)
H5	0.4631	0.1372	0.3097	0.090*
C6	0.5478 (4)	0.1116 (2)	0.4253 (2)	0.0952 (10)
H6	0.5224	0.0415	0.4246	0.114*
C7	0.6198 (4)	0.1576 (3)	0.4952 (2)	0.0900 (9)
H7	0.6427	0.1188	0.5417	0.108*
C8	0.6573 (3)	0.2605 (2)	0.49595 (17)	0.0792 (7)
H8	0.7048	0.2919	0.5432	0.095*
C9	0.6250 (3)	0.3181 (2)	0.42674 (15)	0.0674 (6)
H9	0.6521	0.3879	0.4277	0.081*
C10	0.6770 (3)	0.3332 (2)	0.24373 (17)	0.0767 (8)
H10A	0.7614	0.3630	0.2826	0.092*
H10B	0.7072	0.2630	0.2327	0.092*
C11	0.6550 (5)	0.3962 (3)	0.16836 (19)	0.1020 (11)
H11A	0.7526	0.3949	0.1475	0.122*
H11B	0.5733	0.3643	0.1292	0.122*
C12	0.6101 (3)	0.5072 (2)	0.18016 (13)	0.0691 (6)
H12	0.7015	0.5514	0.1772	0.083*
C13	0.5575 (2)	0.52688 (17)	0.26113 (12)	0.0546 (5)
H13	0.4833	0.5851	0.2518	0.066*
C14	0.8453 (3)	0.55368 (18)	0.33173 (15)	0.0629 (6)
H14	0.8818	0.5258	0.2883	0.075*
C15	0.9531 (3)	0.5882 (2)	0.39677 (19)	0.0804 (8)
H15	1.0609	0.5831	0.3967	0.097*
C16	0.9023 (4)	0.6296 (3)	0.46064 (19)	0.0902 (9)
H16	0.9751	0.6520	0.5044	0.108*
C17	0.7427 (4)	0.6381 (3)	0.46023 (18)	0.0871 (8)
H17	0.7072	0.6672	0.5035	0.105*
C18	0.6351 (3)	0.6036 (2)	0.39563 (15)	0.0709 (7)
H18	0.5274	0.6097	0.3960	0.085*
C19	0.6841 (2)	0.55994 (15)	0.33034 (13)	0.0525 (5)
C20	0.4780 (6)	0.5352 (5)	0.1122 (2)	0.148 (2)
H20A	0.5080	0.5091	0.0639	0.178*
H20B	0.3853	0.4964	0.1198	0.178*
C21	0.4326 (9)	0.6332 (5)	0.0984 (3)	0.208 (4)
H21A	0.3476	0.6360	0.0534	0.312*
H21B	0.5202	0.6734	0.0874	0.312*
H21C	0.3974	0.6608	0.1442	0.312*
N1	0.4638 (2)	0.43814 (14)	0.28174 (10)	0.0537 (4)
O1	0.2633 (2)	0.54571 (16)	0.29856 (14)	0.0899 (6)
Cl1	0.10294 (11)	0.32963 (9)	0.21188 (5)	0.1187 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0550 (12)	0.0729 (15)	0.0633 (13)	0.0061 (11)	0.0111 (10)	0.0058 (11)
C2	0.0547 (13)	0.0925 (19)	0.0743 (15)	−0.0028 (12)	0.0100 (11)	0.0089 (14)
C3	0.0616 (12)	0.0538 (12)	0.0591 (12)	−0.0044 (10)	0.0109 (10)	−0.0111 (10)
C4	0.0512 (11)	0.0512 (12)	0.0680 (13)	0.0020 (9)	0.0137 (9)	−0.0013 (10)
C5	0.0824 (17)	0.0577 (14)	0.0891 (19)	−0.0074 (12)	0.0251 (14)	−0.0069 (13)
C6	0.118 (3)	0.0581 (16)	0.117 (3)	−0.0017 (16)	0.043 (2)	0.0175 (17)
C7	0.094 (2)	0.084 (2)	0.094 (2)	0.0109 (16)	0.0215 (17)	0.0320 (17)
C8	0.0758 (16)	0.089 (2)	0.0697 (16)	0.0028 (14)	0.0056 (12)	0.0117 (14)
C9	0.0703 (14)	0.0587 (13)	0.0704 (15)	−0.0040 (11)	0.0055 (11)	0.0014 (11)
C10	0.0902 (18)	0.0597 (14)	0.0897 (18)	0.0065 (12)	0.0419 (15)	−0.0110 (13)
C11	0.147 (3)	0.095 (2)	0.0786 (19)	−0.004 (2)	0.060 (2)	−0.0140 (17)
C12	0.0755 (15)	0.0844 (17)	0.0496 (12)	0.0084 (13)	0.0170 (10)	0.0094 (11)
C13	0.0560 (11)	0.0566 (12)	0.0519 (11)	0.0050 (9)	0.0116 (9)	0.0064 (9)
C14	0.0605 (13)	0.0547 (13)	0.0742 (15)	0.0025 (10)	0.0145 (11)	−0.0003 (11)
C15	0.0621 (14)	0.0729 (17)	0.101 (2)	0.0006 (12)	0.0007 (13)	−0.0113 (15)
C16	0.0839 (19)	0.088 (2)	0.089 (2)	−0.0052 (16)	−0.0108 (15)	−0.0205 (16)
C17	0.094 (2)	0.093 (2)	0.0735 (17)	−0.0028 (16)	0.0130 (14)	−0.0247 (15)
C18	0.0667 (14)	0.0771 (16)	0.0700 (15)	−0.0016 (12)	0.0158 (11)	−0.0124 (13)
C19	0.0591 (12)	0.0421 (10)	0.0565 (11)	0.0014 (8)	0.0112 (9)	0.0053 (9)
C20	0.167 (4)	0.218 (6)	0.0575 (18)	0.076 (4)	0.015 (2)	0.019 (2)
C21	0.292 (8)	0.236 (7)	0.103 (3)	0.176 (7)	0.053 (4)	0.062 (4)
N1	0.0512 (9)	0.0571 (10)	0.0523 (9)	0.0013 (8)	0.0082 (7)	0.0004 (8)
O1	0.0676 (11)	0.0842 (14)	0.1236 (17)	0.0206 (10)	0.0325 (11)	0.0125 (12)
Cl1	0.1024 (6)	0.1474 (9)	0.0951 (6)	−0.0399 (6)	−0.0115 (5)	−0.0055 (5)

Geometric parameters (Å, º) top

C1—O1	1.223 (3)	C11—H11A	0.9700
C1—N1	1.358 (3)	C11—H11B	0.9700
C1—C2	1.507 (4)	C12—C20	1.514 (4)
C2—Cl1	1.760 (3)	C12—C13	1.554 (3)
C2—H2A	0.9700	C12—H12	0.9800
C2—H2B	0.9700	C13—N1	1.480 (3)
C3—N1	1.488 (3)	C13—C19	1.516 (3)
C3—C4	1.512 (3)	C13—H13	0.9800
C3—C10	1.528 (3)	C14—C19	1.384 (3)
C3—H3	0.9800	C14—C15	1.386 (4)
C4—C9	1.385 (3)	C14—H14	0.9300
C4—C5	1.387 (3)	C15—C16	1.358 (4)
C5—C6	1.376 (4)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.376 (4)
C6—C7	1.378 (5)	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.380 (4)
C7—C8	1.366 (4)	C17—H17	0.9300
C7—H7	0.9300	C18—C19	1.384 (3)
C8—C9	1.383 (4)	C18—H18	0.9300
C8—H8	0.9300	C20—C21	1.332 (7)
C9—H9	0.9300	C20—H20A	0.9700
C10—C11	1.507 (4)	C20—H20B	0.9700
C10—H10A	0.9700	C21—H21A	0.9600
C10—H10B	0.9700	C21—H21B	0.9600
C11—C12	1.508 (4)	C21—H21C	0.9600

O1—C1—N1	123.3 (2)	C11—C12—C20	107.4 (3)
O1—C1—C2	117.9 (2)	C11—C12—C13	113.4 (2)
N1—C1—C2	118.8 (2)	C20—C12—C13	110.3 (2)
C1—C2—Cl1	109.59 (18)	C11—C12—H12	108.6
C1—C2—H2A	109.8	C20—C12—H12	108.6
Cl1—C2—H2A	109.8	C13—C12—H12	108.6
C1—C2—H2B	109.8	N1—C13—C19	112.11 (16)
Cl1—C2—H2B	109.8	N1—C13—C12	110.22 (19)
H2A—C2—H2B	108.2	C19—C13—C12	117.27 (19)
N1—C3—C4	114.88 (17)	N1—C13—H13	105.4
N1—C3—C10	109.32 (18)	C19—C13—H13	105.4
C4—C3—C10	109.7 (2)	C12—C13—H13	105.4
N1—C3—H3	107.5	C19—C14—C15	121.1 (2)
C4—C3—H3	107.5	C19—C14—H14	119.5
C10—C3—H3	107.5	C15—C14—H14	119.5
C9—C4—C5	118.4 (2)	C16—C15—C14	120.5 (3)
C9—C4—C3	122.6 (2)	C16—C15—H15	119.8
C5—C4—C3	118.9 (2)	C14—C15—H15	119.8
C6—C5—C4	120.6 (3)	C15—C16—C17	119.6 (3)
C6—C5—H5	119.7	C15—C16—H16	120.2
C4—C5—H5	119.7	C17—C16—H16	120.2
C5—C6—C7	120.4 (3)	C16—C17—C18	120.0 (3)
C5—C6—H6	119.8	C16—C17—H17	120.0
C7—C6—H6	119.8	C18—C17—H17	120.0
C6—C7—C8	119.7 (3)	C17—C18—C19	121.3 (2)
C6—C7—H7	120.2	C17—C18—H18	119.3
C8—C7—H7	120.2	C19—C18—H18	119.3
C9—C8—C7	120.3 (3)	C14—C19—C18	117.5 (2)
C9—C8—H8	119.8	C14—C19—C13	124.8 (2)
C7—C8—H8	119.8	C18—C19—C13	117.66 (19)
C8—C9—C4	120.7 (2)	C21—C20—C12	121.1 (5)
C8—C9—H9	119.7	C21—C20—H20A	107.0
C4—C9—H9	119.7	C12—C20—H20A	107.0
C11—C10—C3	110.8 (3)	C21—C20—H20B	107.0
C11—C10—H10A	109.5	C12—C20—H20B	107.0
C3—C10—H10A	109.5	H20A—C20—H20B	106.8
C11—C10—H10B	109.5	C20—C21—H21A	109.5
C3—C10—H10B	109.5	C20—C21—H21B	109.5
H10A—C10—H10B	108.1	H21A—C21—H21B	109.5
C12—C11—C10	113.2 (2)	C20—C21—H21C	109.5
C12—C11—H11A	108.9	H21A—C21—H21C	109.5
C10—C11—H11A	108.9	H21B—C21—H21C	109.5
C12—C11—H11B	108.9	C1—N1—C13	117.42 (18)
C10—C11—H11B	108.9	C1—N1—C3	122.16 (18)
H11A—C11—H11B	107.8	C13—N1—C3	119.97 (16)

O1—C1—C2—Cl1	91.4 (3)	C15—C16—C17—C18	0.8 (5)
N1—C1—C2—Cl1	−88.9 (2)	C16—C17—C18—C19	0.0 (5)
N1—C3—C4—C9	−43.6 (3)	C15—C14—C19—C18	1.1 (3)
C10—C3—C4—C9	80.1 (3)	C15—C14—C19—C13	178.3 (2)
N1—C3—C4—C5	140.4 (2)	C17—C18—C19—C14	−1.0 (4)
C10—C3—C4—C5	−96.0 (2)	C17—C18—C19—C13	−178.3 (3)
C9—C4—C5—C6	−1.0 (4)	N1—C13—C19—C14	115.1 (2)
C3—C4—C5—C6	175.2 (2)	C12—C13—C19—C14	−13.9 (3)
C4—C5—C6—C7	1.1 (5)	N1—C13—C19—C18	−67.7 (3)
C5—C6—C7—C8	−0.2 (5)	C12—C13—C19—C18	163.3 (2)
C6—C7—C8—C9	−0.7 (5)	C11—C12—C20—C21	−167.8 (5)
C7—C8—C9—C4	0.7 (4)	C13—C12—C20—C21	68.1 (6)
C5—C4—C9—C8	0.1 (4)	O1—C1—N1—C13	−8.1 (3)
C3—C4—C9—C8	−175.9 (2)	C2—C1—N1—C13	172.09 (19)
N1—C3—C10—C11	−49.6 (3)	O1—C1—N1—C3	179.6 (2)
C4—C3—C10—C11	−176.4 (2)	C2—C1—N1—C3	−0.2 (3)
C3—C10—C11—C12	60.0 (4)	C19—C13—N1—C1	104.6 (2)
C10—C11—C12—C20	−135.7 (3)	C12—C13—N1—C1	−122.8 (2)
C10—C11—C12—C13	−13.6 (4)	C19—C13—N1—C3	−83.0 (2)
C11—C12—C13—N1	−38.1 (3)	C12—C13—N1—C3	49.6 (2)
C20—C12—C13—N1	82.3 (3)	C4—C3—N1—C1	−69.3 (3)
C11—C12—C13—C19	91.8 (3)	C10—C3—N1—C1	166.8 (2)
C20—C12—C13—C19	−147.8 (3)	C4—C3—N1—C13	118.6 (2)
C19—C14—C15—C16	−0.3 (4)	C10—C3—N1—C13	−5.2 (3)
C14—C15—C16—C17	−0.7 (5)

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄ClNO
M_r	341.86
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.5971 (9), 12.9080 (13), 17.1114 (16)
β (°)	100.501 (5)
V (Å³)	1867.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.25 × 0.23 × 0.23

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.949, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	17549, 4639, 2930
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.226, 1.01
No. of reflections	4639
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.43

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008, 2015) and PLATON (Spek, 2009).

Acknowledgements

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection facilities.

References

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