r-2,c-6-Bis(4-chloro­phen­yl)-t-3-iso­propyl­piperidin-4-one

Thiruvalluvar, A.; Balamurugan, S.; Butcher, R.J.; Manimekalai, A.; Sivakumar, S.

doi:10.1107/S160053680705341X

r-2,c-6-Bis(4-chlorophenyl)-t-3-isopropylpiperidin-4-one

A. Thiruvalluvar, S. Balamurugan, R. J. Butcher, A. Manimekalai and S. Sivakumar

The piperidine ring of the title molecule, C₂₀H₂₁Cl₂NO, is in a chair form. The dihedral angle between the two benzene rings is 52.4 (1)°. The chlorophenyl and isopropyl groups have equatorial orientations. Weak C—H

O and C—H

N intramolecular interactions were found in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705341X/is2229sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680705341X/is2229Isup2.hkl Contains datablock I

CCDC reference: 667477

checkCIF report

Key indicators

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.004 Å
R factor = 0.056
wR factor = 0.159
Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.94 Ratio

Alert level C
PLAT245_ALERT_2_C U(iso) H1      Smaller than U(eq) N1      by ...       0.01 AngSq
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C6     = ...          S

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Jayabharathi et al. (2007) have reported synthesis, stereochemistry and antimicrobial evaluation of t-3-benzyl-r-2,c-6-diarylpiperidin-4-one and its derivatives. Balamurugan et al. (2007) have reported a crystal structure of t-3,t-5-dimethyl-r-2,c-6-diphenylpiperidin-4-one wherein the piperidine ring is in a chair form. The piperidine ring of the title molecule, C₂₀H₂₁Cl₂NO, is also in a chair form (Fig. 1). The dihedral angle between the two benzene rings is 52.4 (1)°. The p-chlorophenyl groups at the 2, 6 and the isopropyl group at the 3 position have equatorial orientations. Weak C31—H31···O4 and C66—H66···N1 intramolecular interactions were found in the crystal structure.

Related literature top

For a related crystal structure, see: Balamurugan et al. (2007). For applications of piperidines, see: Jayabharathi et al. (2007).

Experimental top

A mixture of ammonium acetate (0.05 mol, 3.85 g), p-chlorobenzaldehyde (0.1 mol, 14 g) and isobutyl methyl ketone (0.05 mol, 8 ml) in distilled ethanol was heated first to boiling. After cooling, the viscous liquid obtained was dissolved in ether (200 ml) and shaken with 100 ml concentrated hydrochloric acid. The precipitated hydrochloride of t-3-isopropyl-r-2,c-6-bis(p-chlorophenyl)piperidin-4-one was removed by filtration and washed first with 40 ml mixture of ethanol and ether (1:1) and then with ether to remove most of the coloured impurities. The base was liberated from an alcoholic solution by adding aqueous ammonia and then diluted with water. It was recrystallized from alcohol. The yield of the isolated product was 3.5 g.

Structure description top

For a related crystal structure, see: Balamurugan et al. (2007). For applications of piperidines, see: Jayabharathi et al. (2007).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of the title compound, with the atomic numbering and 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radius.

r-2,c-6-Bis(4-chlorophenyl)-t-3-isopropylpiperidin-4-one top

Crystal data top

C₂₀H₂₁Cl₂NO	F(000) = 760
M_r = 362.28	D_x = 1.358 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 374.5 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.3013 (7) Å	Cell parameters from 7357 reflections
b = 8.3742 (4) Å	θ = 4.5–32.6°
c = 12.3687 (5) Å	µ = 0.37 mm⁻¹
β = 98.647 (4)°	T = 200 K
V = 1771.66 (13) Å³	Triangular plate, pale yellow
Z = 4	0.49 × 0.39 × 0.15 mm

Data collection top

Oxford Diffraction Gemini diffractometer	3106 independent reflections
Radiation source: fine-focus sealed tube	2262 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.087
Detector resolution: 10.5081 pixels mm^-1	θ_max = 25.0°, θ_min = 4.5°
φ and ω scans	h = −20→20
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)'	k = −9→9
T_min = 0.83, T_max = 0.95	l = −14→14
20264 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0961P)² + 0.4302P] where P = (F_o² + 2F_c²)/3
3106 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₀H₂₁Cl₂NO	V = 1771.66 (13) Å³
M_r = 362.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.3013 (7) Å	µ = 0.37 mm⁻¹
b = 8.3742 (4) Å	T = 200 K
c = 12.3687 (5) Å	0.49 × 0.39 × 0.15 mm
β = 98.647 (4)°

Data collection top

Oxford Diffraction Gemini diffractometer	3106 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)'	2262 reflections with I > 2σ(I)
T_min = 0.83, T_max = 0.95	R_int = 0.087
20264 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.68 e Å⁻³
3106 reflections	Δρ_min = −0.47 e Å⁻³
223 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl2	0.47429 (5)	1.43833 (11)	0.20225 (8)	0.0555 (3)
Cl6	−0.16197 (4)	0.82188 (9)	0.28263 (6)	0.0369 (3)
O4	0.21967 (14)	0.5598 (3)	−0.09979 (18)	0.0461 (8)
N1	0.17357 (14)	0.9389 (3)	0.07616 (18)	0.0282 (8)
C2	0.23615 (16)	0.9527 (3)	0.0085 (2)	0.0270 (8)
C3	0.27588 (17)	0.7871 (3)	0.0021 (2)	0.0295 (9)
C4	0.21346 (18)	0.6618 (3)	−0.0314 (2)	0.0335 (9)
C5	0.14275 (18)	0.6673 (3)	0.0264 (3)	0.0349 (9)
C6	0.10934 (17)	0.8363 (3)	0.0287 (2)	0.0282 (8)
C21	0.29219 (16)	1.0795 (3)	0.0581 (2)	0.0260 (8)
C22	0.32394 (17)	1.0747 (3)	0.1688 (2)	0.0308 (9)
C23	0.37782 (18)	1.1868 (4)	0.2133 (2)	0.0352 (9)
C24	0.40124 (18)	1.3055 (4)	0.1487 (3)	0.0358 (10)
C25	0.36874 (18)	1.3191 (4)	0.0393 (3)	0.0361 (10)
C26	0.31356 (18)	1.2058 (3)	−0.0041 (2)	0.0327 (9)
C31	0.34210 (17)	0.7759 (4)	−0.0675 (2)	0.0340 (9)
C32	0.42054 (19)	0.8408 (4)	−0.0111 (3)	0.0494 (11)
C33	0.3201 (2)	0.8477 (4)	−0.1822 (3)	0.0453 (11)
C61	0.04229 (17)	0.8390 (3)	0.0933 (2)	0.0278 (8)
C62	−0.02815 (18)	0.7682 (3)	0.0497 (2)	0.0312 (9)
C63	−0.09090 (18)	0.7606 (3)	0.1068 (2)	0.0305 (9)
C64	−0.08322 (17)	0.8306 (3)	0.2097 (2)	0.0280 (8)
C65	−0.01491 (18)	0.9056 (4)	0.2538 (2)	0.0344 (10)
C66	0.04783 (18)	0.9076 (4)	0.1971 (2)	0.0332 (9)
H1	0.1563 (17)	1.026 (3)	0.082 (2)	0.015 (7)*
H2	0.21283	0.98661	−0.06686	0.0323*
H3	0.29985	0.75999	0.07855	0.0354*
H5A	0.15739	0.62846	0.10227	0.0418*
H5B	0.10203	0.59509	−0.01127	0.0418*
H6	0.09033	0.87181	−0.04789	0.0339*
H22	0.30815	0.99297	0.21410	0.0370*
H23	0.39884	1.18196	0.28871	0.0423*
H25	0.38369	1.40327	−0.00471	0.0433*
H26	0.28992	1.21520	−0.07828	0.0393*
H31	0.35046	0.65928	−0.07880	0.0408*
H31B	0.43102	0.80007	0.06399	0.0741*
H32A	0.46223	0.80630	−0.05135	0.0741*
H32C	0.41862	0.95777	−0.00966	0.0741*
H33A	0.31687	0.96417	−0.17656	0.0682*
H33B	0.26943	0.80529	−0.21596	0.0682*
H33C	0.36012	0.81951	−0.22723	0.0682*
H62	−0.03336	0.72355	−0.02164	0.0375*
H63	−0.13807	0.70893	0.07638	0.0366*
H65	−0.01101	0.95583	0.32328	0.0412*
H66	0.09544	0.95627	0.22897	0.0399*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2	0.0381 (5)	0.0589 (6)	0.0684 (6)	−0.0143 (4)	0.0042 (4)	−0.0239 (4)
Cl6	0.0310 (4)	0.0479 (5)	0.0328 (4)	−0.0013 (3)	0.0084 (3)	0.0031 (3)
O4	0.0437 (14)	0.0436 (13)	0.0524 (13)	−0.0041 (11)	0.0118 (11)	−0.0164 (11)
N1	0.0255 (13)	0.0287 (14)	0.0303 (12)	−0.0016 (12)	0.0041 (10)	−0.0022 (10)
C2	0.0235 (14)	0.0358 (16)	0.0211 (12)	0.0003 (12)	0.0019 (11)	0.0041 (11)
C3	0.0286 (16)	0.0381 (16)	0.0215 (13)	0.0016 (13)	0.0030 (11)	0.0015 (11)
C4	0.0314 (17)	0.0336 (16)	0.0342 (15)	0.0032 (14)	0.0004 (13)	0.0043 (13)
C5	0.0301 (16)	0.0331 (16)	0.0412 (16)	−0.0053 (14)	0.0049 (13)	0.0011 (13)
C6	0.0261 (15)	0.0338 (16)	0.0238 (13)	−0.0027 (13)	0.0005 (11)	0.0003 (11)
C21	0.0207 (14)	0.0294 (15)	0.0281 (14)	0.0008 (12)	0.0039 (11)	−0.0003 (11)
C22	0.0313 (16)	0.0363 (16)	0.0251 (14)	0.0032 (14)	0.0049 (12)	0.0009 (12)
C23	0.0308 (16)	0.0447 (18)	0.0282 (14)	0.0069 (15)	−0.0019 (12)	−0.0066 (13)
C24	0.0271 (16)	0.0362 (17)	0.0441 (17)	−0.0032 (14)	0.0051 (13)	−0.0142 (14)
C25	0.0334 (17)	0.0314 (16)	0.0436 (17)	−0.0056 (14)	0.0060 (14)	0.0036 (13)
C26	0.0290 (16)	0.0361 (16)	0.0318 (14)	−0.0014 (13)	0.0004 (12)	0.0055 (12)
C31	0.0302 (17)	0.0389 (17)	0.0339 (15)	0.0008 (14)	0.0078 (13)	−0.0065 (13)
C32	0.0269 (17)	0.063 (2)	0.059 (2)	−0.0004 (17)	0.0086 (15)	−0.0101 (18)
C33	0.050 (2)	0.055 (2)	0.0339 (16)	−0.0043 (18)	0.0159 (15)	−0.0026 (15)
C61	0.0260 (15)	0.0298 (15)	0.0267 (13)	−0.0015 (13)	0.0007 (12)	0.0040 (11)
C62	0.0316 (17)	0.0344 (16)	0.0268 (14)	−0.0032 (14)	0.0018 (12)	−0.0041 (12)
C63	0.0255 (16)	0.0321 (16)	0.0319 (14)	−0.0034 (13)	−0.0021 (12)	−0.0031 (12)
C64	0.0271 (15)	0.0314 (15)	0.0263 (13)	−0.0007 (13)	0.0070 (12)	0.0076 (12)
C65	0.0379 (18)	0.0456 (18)	0.0190 (13)	−0.0073 (15)	0.0023 (12)	−0.0002 (12)
C66	0.0298 (16)	0.0410 (17)	0.0278 (14)	−0.0096 (14)	0.0009 (12)	−0.0012 (12)

Geometric parameters (Å, º) top

Cl2—C24	1.738 (3)	C63—C64	1.389 (3)
Cl6—C64	1.745 (3)	C64—C65	1.377 (4)
O4—C4	1.218 (3)	C65—C66	1.378 (4)
N1—C2	1.469 (4)	C2—H2	1.0000
N1—C6	1.457 (4)	C3—H3	1.0000
N1—H1	0.80 (3)	C5—H5A	0.9900
C2—C21	1.505 (4)	C5—H5B	0.9900
C2—C3	1.555 (4)	C6—H6	1.0000
C3—C4	1.518 (4)	C22—H22	0.9500
C3—C31	1.536 (4)	C23—H23	0.9500
C4—C5	1.508 (4)	C25—H25	0.9500
C5—C6	1.531 (4)	C26—H26	0.9500
C6—C61	1.505 (4)	C31—H31	1.0000
C21—C26	1.390 (4)	C32—H31B	0.9800
C21—C22	1.397 (3)	C32—H32A	0.9800
C22—C23	1.378 (4)	C32—H32C	0.9800
C23—C24	1.374 (5)	C33—H33A	0.9800
C24—C25	1.390 (5)	C33—H33B	0.9800
C25—C26	1.395 (4)	C33—H33C	0.9800
C31—C32	1.529 (4)	C62—H62	0.9500
C31—C33	1.535 (4)	C63—H63	0.9500
C61—C66	1.397 (4)	C65—H65	0.9500
C61—C62	1.389 (4)	C66—H66	0.9500
C62—C63	1.383 (4)

Cl2···C23ⁱ	3.341 (3)	H2···H26	2.3500
Cl6···C22ⁱⁱ	3.606 (3)	H2···H33A	2.4200
Cl2···H32Aⁱⁱⁱ	3.0800	H2···Cl6^vi	3.1200
Cl2···H33C^iv	3.0500	H2···C63^vi	2.9800
Cl2···H23ⁱ	2.9900	H2···C64^vi	3.0500
Cl6···H1ⁱⁱ	2.98 (2)	H3···C22	2.8700
Cl6···H5A^v	2.9300	H3···H22	2.5600
Cl6···H2^vi	3.1200	H3···H31B	2.3300
Cl6···H26^vi	3.1100	H3···C33^vii	3.0600
Cl6···H62^vii	3.0600	H3···H33C^vii	2.5600
O4···C33	3.225 (4)	H5A···Cl6ⁱⁱ	2.9300
O4···H31	2.3900	H5B···C62	2.8700
O4···H33B	2.7200	H5B···H62	2.5600
O4···H63^viii	2.7000	H6···H2	2.3700
O4···H66^ix	2.7800	H6···H62	2.5400
N1···H22	2.7100	H22···N1	2.7100
N1···H66	2.4900	H22···H3	2.5600
C21···C32	3.199 (4)	H23···Cl2^x	2.9900
C22···Cl6^v	3.606 (3)	H25···H31^xi	2.3700
C22···C32	3.564 (4)	H26···H2	2.3500
C23···Cl2^x	3.341 (3)	H26···H33A	2.5100
C26···C32	3.581 (4)	H26···Cl6^vi	3.1100
C32···C21	3.199 (4)	H31···O4	2.3900
C32···C22	3.564 (4)	H31···H25^xii	2.3700
C32···C26	3.581 (4)	H31B···H3	2.3300
C33···O4	3.225 (4)	H32A···H33C	2.5900
C2···H33A	2.8600	H32A···Cl2ⁱⁱⁱ	3.0800
C4···H33B	2.8700	H32A···C24ⁱⁱⁱ	2.9600
C5···H62	3.0500	H32A···C25ⁱⁱⁱ	3.0900
C21···H32C	2.6600	H32C···C21	2.6600
C22···H3	2.8700	H32C···C22	3.1000
C22···H32C	3.1000	H32C···C26	2.7700
C22···H1	2.97 (3)	H32C···H33A	2.5000
C24···H32Aⁱⁱⁱ	2.9600	H33A···C2	2.8600
C25···H32Aⁱⁱⁱ	3.0900	H33A···C26	2.9500
C26···H32C	2.7700	H33A···H2	2.4200
C26···H33A	2.9500	H33A···H26	2.5100
C33···H2	2.7600	H33A···H32C	2.5000
C33···H3^ix	3.0600	H33B···O4	2.7200
C62···H5B	2.8700	H33B···C4	2.8700
C62···H65ⁱⁱ	3.0700	H33C···H32A	2.5900
C62···H1^vi	3.08 (3)	H33C···Cl2^xiii	3.0500
C63···H1^vi	3.02 (3)	H33C···H3^ix	2.5600
C63···H2^vi	2.9800	H62···C5	3.0500
C64···H2^vi	3.0500	H62···H5B	2.5600
C65···H62^vii	3.0400	H62···H6	2.5400
C66···H1	2.71 (3)	H62···Cl6^ix	3.0600
H1···C22	2.97 (3)	H62···C65^ix	3.0400
H1···C66	2.71 (3)	H62···H65^ix	2.5100
H1···H66	2.3100	H63···O4^viii	2.7000
H1···Cl6^v	2.98 (2)	H65···C62^v	3.0700
H1···C62^vi	3.08 (3)	H65···H62^vii	2.5100
H1···C63^vi	3.02 (3)	H66···N1	2.4900
H2···C33	2.7600	H66···H1	2.3100
H2···H6	2.3700	H66···O4^vii	2.7800

C2—N1—C6	113.6 (2)	C2—C3—H3	106.00
C6—N1—H1	108 (2)	C4—C3—H3	106.00
C2—N1—H1	107 (2)	C31—C3—H3	106.00
N1—C2—C21	107.9 (2)	C4—C5—H5A	109.00
N1—C2—C3	109.2 (2)	C4—C5—H5B	109.00
C3—C2—C21	112.8 (2)	C6—C5—H5A	109.00
C2—C3—C31	117.1 (2)	C6—C5—H5B	109.00
C2—C3—C4	109.2 (2)	H5A—C5—H5B	108.00
C4—C3—C31	111.4 (2)	N1—C6—H6	109.00
C3—C4—C5	116.4 (2)	C5—C6—H6	109.00
O4—C4—C3	122.7 (3)	C61—C6—H6	109.00
O4—C4—C5	120.9 (3)	C21—C22—H22	120.00
C4—C5—C6	111.9 (2)	C23—C22—H22	119.00
N1—C6—C5	106.6 (2)	C22—C23—H23	120.00
N1—C6—C61	112.3 (2)	C24—C23—H23	120.00
C5—C6—C61	110.3 (2)	C24—C25—H25	121.00
C2—C21—C22	120.9 (2)	C26—C25—H25	121.00
C22—C21—C26	117.8 (2)	C21—C26—H26	119.00
C2—C21—C26	121.3 (2)	C25—C26—H26	119.00
C21—C22—C23	121.0 (2)	C3—C31—H31	106.00
C22—C23—C24	120.1 (3)	C32—C31—H31	106.00
C23—C24—C25	120.9 (3)	C33—C31—H31	106.00
Cl2—C24—C23	120.2 (3)	C31—C32—H31B	109.00
Cl2—C24—C25	118.9 (3)	C31—C32—H32A	110.00
C24—C25—C26	118.2 (3)	C31—C32—H32C	109.00
C21—C26—C25	121.9 (3)	H31B—C32—H32A	109.00
C3—C31—C33	113.1 (2)	H31B—C32—H32C	109.00
C32—C31—C33	111.2 (3)	H32A—C32—H32C	109.00
C3—C31—C32	114.1 (2)	C31—C33—H33A	109.00
C62—C61—C66	117.9 (3)	C31—C33—H33B	109.00
C6—C61—C62	119.3 (2)	C31—C33—H33C	109.00
C6—C61—C66	122.9 (3)	H33A—C33—H33B	110.00
C61—C62—C63	122.1 (2)	H33A—C33—H33C	109.00
C62—C63—C64	118.3 (3)	H33B—C33—H33C	110.00
Cl6—C64—C65	120.3 (2)	C61—C62—H62	119.00
Cl6—C64—C63	118.8 (2)	C63—C62—H62	119.00
C63—C64—C65	120.9 (3)	C62—C63—H63	121.00
C64—C65—C66	119.9 (2)	C64—C63—H63	121.00
C61—C66—C65	120.8 (3)	C64—C65—H65	120.00
N1—C2—H2	109.00	C66—C65—H65	120.00
C3—C2—H2	109.00	C61—C66—H66	120.00
C21—C2—H2	109.00	C65—C66—H66	120.00

C6—N1—C2—C3	−65.3 (3)	N1—C6—C61—C62	169.8 (2)
C6—N1—C2—C21	171.8 (2)	N1—C6—C61—C66	−11.4 (4)
C2—N1—C6—C5	65.5 (3)	C5—C6—C61—C62	−71.5 (3)
C2—N1—C6—C61	−173.6 (2)	C5—C6—C61—C66	107.4 (3)
N1—C2—C3—C4	51.0 (3)	C2—C21—C22—C23	177.2 (3)
N1—C2—C3—C31	178.7 (2)	C26—C21—C22—C23	−3.4 (4)
C21—C2—C3—C4	171.0 (2)	C2—C21—C26—C25	−176.3 (3)
C21—C2—C3—C31	−61.3 (3)	C22—C21—C26—C25	4.2 (4)
N1—C2—C21—C22	51.9 (3)	C21—C22—C23—C24	−0.1 (5)
N1—C2—C21—C26	−127.5 (3)	C22—C23—C24—Cl2	−175.4 (2)
C3—C2—C21—C22	−68.8 (3)	C22—C23—C24—C25	2.9 (5)
C3—C2—C21—C26	111.8 (3)	Cl2—C24—C25—C26	176.2 (2)
C2—C3—C4—O4	135.7 (3)	C23—C24—C25—C26	−2.1 (5)
C2—C3—C4—C5	−45.4 (3)	C24—C25—C26—C21	−1.6 (5)
C31—C3—C4—O4	4.8 (4)	C6—C61—C62—C63	177.2 (2)
C31—C3—C4—C5	−176.3 (2)	C66—C61—C62—C63	−1.7 (4)
C2—C3—C31—C32	78.8 (3)	C6—C61—C66—C65	−179.2 (3)
C2—C3—C31—C33	−49.6 (3)	C62—C61—C66—C65	−0.4 (4)
C4—C3—C31—C32	−154.5 (3)	C61—C62—C63—C64	1.9 (4)
C4—C3—C31—C33	77.1 (3)	C62—C63—C64—Cl6	180.0 (2)
O4—C4—C5—C6	−133.0 (3)	C62—C63—C64—C65	0.0 (4)
C3—C4—C5—C6	48.2 (3)	Cl6—C64—C65—C66	178.0 (2)
C4—C5—C6—N1	−54.1 (3)	C63—C64—C65—C66	−2.0 (4)
C4—C5—C6—C61	−176.3 (2)	C64—C65—C66—C61	2.2 (5)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2; (iii) −x+1, −y+2, −z; (iv) x, −y+5/2, z+1/2; (v) −x, y+1/2, −z+1/2; (vi) −x, −y+2, −z; (vii) x, −y+3/2, z+1/2; (viii) −x, −y+1, −z; (ix) x, −y+3/2, z−1/2; (x) −x+1, y−1/2, −z+1/2; (xi) x, y+1, z; (xii) x, y−1, z; (xiii) x, −y+5/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C31—H31···O4	1.00	2.39	2.769 (4)	102
C66—H66···N1	0.95	2.49	2.832 (4)	101

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁Cl₂NO
M_r	362.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	17.3013 (7), 8.3742 (4), 12.3687 (5)
β (°)	98.647 (4)
V (Å³)	1771.66 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.49 × 0.39 × 0.15

Data collection
Diffractometer	Oxford Diffraction Gemini
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)'
T_min, T_max	0.83, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections	20264, 3106, 2262
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.159, 1.05
No. of reflections	3106
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.47

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).