2,4-Bis(4-chloro­phen­yl)-1-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one

Parthiban, P.; Ramkumar, V.; Jeong, Y.T.

doi:10.1107/S1600536810004095

2,4-Bis(4-chlorophenyl)-1-methyl-3-azabicyclo[3.3.1]nonan-9-one

P. Parthiban, V. Ramkumar and Y. T. Jeong

The title compound, C₂₁H₂₁Cl₂NO, exists in a twin-chair conformation with an equatorial orientation of the 4-chlorophenyl groups on both sides of the secondary amino group; the dihedral angle between the 4-chlorophenyl rings is 36.58 (2)°. The crystal packing is stabilized by an intermolecular N—H

O hydrogen bond and a weak Cl

Cl [3.4331 (9) Å] interaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810004095/hb5322sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810004095/hb5322Isup2.hkl Contains datablock I

CCDC reference: 769953

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.045
wR factor = 0.125
Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         26

Alert level G
PLAT793_ALERT_4_G The Model has Chirality at C1      (Verify) ....          R
PLAT793_ALERT_4_G The Model has Chirality at C2      (Verify) ....          S
PLAT793_ALERT_4_G The Model has Chirality at C6      (Verify) ....          R
PLAT793_ALERT_4_G The Model has Chirality at C7      (Verify) ....          R

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

3-Azabicyclo[3.3.1]nonanes are an important class of heterocyclic compounds due to their broad spectrum of biological activities such as antibacterial, antifungal, analgesic, antogonistic, anti-inflammatory, local anesthetic and hypotensive activity, and their presence in a wide variety of naturally occurring diterpenoid/norditerpenoid alkaloids (Parthiban et al., 2009; Hardick et al., 1996; Jeyaraman & Avila, 1981). As stereochemistry plays a vital role in biological activities, it is essential to establish the stereochemistry of the synthesized bio-active molecules. Owing to the diverse possibilities in the conformation of the 3-azabicycle such as chair-chair (Parthiban et al., 2009b & 2010), chair-boat (Smith-Verdier et al., 1983) and boat-boat (Padegimas & Kovacic, 1972), the present crystal study was undertaken to examine the stereochemistry of the synthesized 2,4-bis(4-chlorophenyl)-1-methyl-3-azabicyclo[3.3.1]nonan-9-one.

The crystallographic analysis of the title compound shows that the piperidine ring adopts a near ideal chair conformation. The total puckering amplitude Q_T is 0.587 (2)Å and the phase angle θ is 1.8 (2)° (Cremer & Pople, 1975). The smallest displacement asymmetry parameters being q2 and q3 are 0.022 (2)Å and 0.587 (2) Å, respectively (Nardelli, 1983). The deviation of ring atoms C8 and N1 from the C1/C2/C6/C7 plane by 0.677 (3)Å and -0.642 (3) Å, respectively.

The crystallographic analysis of the title compound suggests that the cyclohexane ring deviates from the ideal chair conformation. The total puckering amplitude Q_T is 0.573 (2)Å and the phase angle θ is 13.8 (2)° (Cremer & Pople, 1975). The smallest displacement asymmetry parameters being q2 and q3 are 0.134 (2)Å and 0.556 (2) Å, respectively (Nardelli, 1983). The deviation of ring atoms C4 and C8 from the C2/C3/C5/C6 plane by -0.554 (4)Å and 0.723 (2) Å, respectively.

According to the crystallogrphic analysis, the title compound, C₂₁H₂₁Cl₂N O, exists in a twin-chair conformation with an equatorial orientation of the para-chlorophenyl groups on both sides of the secondary amino group.

In the title compound, the para-chlorophenyl rings are orientated at an angle of 36.58 (2)° with respect to one another, whereas in its non-methyl analog, 2,4-bis(4-chlorophenyl)-3- azabicyclo[3.3.1]nonan-9-one, the angle is 31.33 (3)°. The crystal structure of the title compound is stabilized by an intermolecular N—H···O interaction and a weak Cl—Cl interaction [Cl···Cl = 3.43 Å]. Though similar interactions observed in the non-methyl analog, the hydrogen bond geometries such as distance and angle of N1—H1···O1 [respectively, 3.1202Å and 160.2 (18)°] are comparatively lower than the title compound (Table 1).

In the title compound, the torsion angles of C1—C2—C8—C9 and C6—C7—C8—C16 are -178.85 (4)° and -179.35 (4)°, respectively (in the non-methyl analog of the title compound, they are -177.88 (4)° and -179.01 (4)°).

Related literature top

For the synthesis and biological activity of 3-azabicyclo[3.3.1] nonan-9-ones, see: Parthiban et al. (2009); Hardick et al. (1996); Jeyaraman & Avila (1981). For the structure of the non-methylated analog of the title compound, see: Parthiban et al. (2009a). For related structures with similar conformations, see: Parthiban et al. (2009b, 2010). For a related structure with chair–boat conformation, see: Smith-Verdier et al. (1983). For a related structure with boat–boat conformation, see: Padegimas & Kovacic (1972). For ring puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).

For related literature, see: Padegimas & Kovacic (1972).

Experimental top

The 1-methyl-2,4-bis(4-chlorophenyl)-3-azabicyclo[3.3.1]nonan-9-one was synthesized by a modified Mannich reaction in one-pot, using para-chlorobenzaldehyde (0.1 mol, 14.06 g), 2-methylcyclohexanone (0.05 mol, 5.61 g/6.07 ml) and ammonium acetate (0.075 mol, 5.78 g) in 50 ml of absolute ethanol. The mixture was gently warmed on a hot plate with stirring and continued at 303-308 K (30-35° C) till completion of the reaction. The progress was monitered by TLC. After all starting material was used up, the crude 3-azabicyclononan-9-one was separated by filtration and washed with a 1:5 ethanol-ether mixture, till the solid becomes colorless. Colourless blocks of (I) were obtained by slow evoporation from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (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) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with atoms represented with 30% probability ellipsoids.
	Fig. 2. Packing diagram for (I) showing the N—H···O and Cl···Cl interactions.

2,4-Bis(4-chlorophenyl)-1-methyl-3-azabicyclo[3.3.1]nonan-9-one top

Crystal data top

C₂₁H₂₁Cl₂NO	F(000) = 1568
M_r = 374.29	D_x = 1.312 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7359 reflections
a = 28.4515 (14) Å	θ = 2.5–27.3°
b = 7.0380 (3) Å	µ = 0.35 mm⁻¹
c = 21.2771 (12) Å	T = 298 K
β = 117.148 (4)°	Rectangular block, colourless
V = 3791.2 (3) Å³	0.58 × 0.42 × 0.18 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	4661 independent reflections
Radiation source: fine-focus sealed tube	3149 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
phi and ω scans	θ_max = 28.2°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −36→37
T_min = 0.822, T_max = 0.940	k = −8→9
24985 measured reflections	l = −28→27

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0487P)² + 3.2087P] where P = (F_o² + 2F_c²)/3
4661 reflections	(Δ/σ)_max = 0.001
231 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₁H₂₁Cl₂NO	V = 3791.2 (3) Å³
M_r = 374.29	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.4515 (14) Å	µ = 0.35 mm⁻¹
b = 7.0380 (3) Å	T = 298 K
c = 21.2771 (12) Å	0.58 × 0.42 × 0.18 mm
β = 117.148 (4)°

Data collection top

Bruker APEXII CCD diffractometer	4661 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	3149 reflections with I > 2σ(I)
T_min = 0.822, T_max = 0.940	R_int = 0.033
24985 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.36 e Å⁻³
4661 reflections	Δρ_min = −0.43 e Å⁻³
231 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell esds are taken

into account individually in the estimation of esds in distances, angles

and torsion angles; correlations between esds in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell esds is used for estimating esds 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	0.17656 (7)	0.4818 (2)	0.98420 (9)	0.0357 (4)
H1	0.2131	0.4889	0.9916	0.043*
C2	0.15724 (7)	0.6894 (2)	0.98539 (10)	0.0393 (4)
C3	0.09894 (8)	0.7068 (3)	0.97191 (11)	0.0501 (5)
H3A	0.0949	0.6354	1.0082	0.060*
H3B	0.0919	0.8391	0.9772	0.060*
C4	0.05740 (8)	0.6377 (3)	0.90001 (12)	0.0556 (5)
H4A	0.0228	0.6790	0.8929	0.067*
H4B	0.0575	0.4999	0.8993	0.067*
C5	0.06735 (8)	0.7126 (3)	0.83970 (11)	0.0559 (5)
H5A	0.0564	0.8446	0.8311	0.067*
H5B	0.0456	0.6416	0.7972	0.067*
C6	0.12516 (8)	0.6988 (3)	0.85398 (10)	0.0450 (4)
H6	0.1292	0.7694	0.8171	0.054*
C7	0.14595 (7)	0.4935 (2)	0.85650 (9)	0.0395 (4)
H7	0.1826	0.5010	0.8644	0.047*
C8	0.15846 (7)	0.7924 (2)	0.92360 (10)	0.0413 (4)
C9	0.17610 (7)	0.3620 (2)	1.04297 (9)	0.0376 (4)
C10	0.22206 (8)	0.3354 (3)	1.10561 (10)	0.0478 (5)
H10	0.2537	0.3846	1.1099	0.057*
C11	0.22168 (9)	0.2369 (3)	1.16196 (10)	0.0537 (5)
H11	0.2528	0.2196	1.2035	0.064*
C12	0.17493 (9)	0.1654 (3)	1.15562 (10)	0.0487 (5)
C13	0.12899 (8)	0.1845 (3)	1.09386 (11)	0.0504 (5)
H13	0.0976	0.1325	1.0897	0.061*
C14	0.12984 (7)	0.2817 (3)	1.03794 (10)	0.0443 (4)
H14	0.0988	0.2938	0.9960	0.053*
C15	0.19367 (9)	0.7841 (3)	1.05543 (11)	0.0562 (5)
H15A	0.2298	0.7607	1.0662	0.084*
H15B	0.1869	0.7328	1.0923	0.084*
H15C	0.1872	0.9186	1.0519	0.084*
C16	0.11369 (7)	0.3942 (3)	0.78664 (10)	0.0426 (4)
C17	0.11848 (10)	0.4523 (3)	0.72767 (12)	0.0616 (6)
H17	0.1433	0.5445	0.7324	0.074*
C18	0.08692 (11)	0.3752 (4)	0.66173 (12)	0.0692 (7)
H18	0.0898	0.4179	0.6222	0.083*
C19	0.05165 (8)	0.2361 (3)	0.65530 (10)	0.0542 (5)
C20	0.04760 (9)	0.1701 (4)	0.71289 (12)	0.0633 (6)
H20	0.0243	0.0719	0.7082	0.076*
C21	0.07852 (9)	0.2507 (3)	0.77862 (11)	0.0571 (5)
H21	0.0754	0.2070	0.8178	0.068*
Cl1	0.17372 (3)	0.04670 (9)	1.22681 (3)	0.0770 (2)
Cl2	0.01186 (2)	0.13710 (11)	0.57245 (3)	0.0829 (2)
N1	0.14499 (6)	0.3905 (2)	0.91547 (8)	0.0379 (3)
O1	0.18212 (6)	0.94051 (19)	0.92903 (8)	0.0570 (4)
H1A	0.1580 (8)	0.278 (3)	0.9181 (11)	0.050 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0365 (9)	0.0322 (8)	0.0378 (9)	−0.0037 (7)	0.0163 (7)	−0.0053 (7)
C2	0.0433 (10)	0.0310 (8)	0.0429 (10)	−0.0022 (7)	0.0190 (8)	−0.0065 (7)
C3	0.0534 (11)	0.0426 (10)	0.0625 (13)	0.0049 (9)	0.0335 (10)	−0.0002 (9)
C4	0.0380 (10)	0.0519 (12)	0.0729 (15)	0.0024 (9)	0.0218 (10)	0.0035 (10)
C5	0.0498 (11)	0.0484 (11)	0.0540 (12)	0.0071 (9)	0.0103 (10)	0.0044 (10)
C6	0.0557 (11)	0.0341 (9)	0.0436 (10)	−0.0041 (8)	0.0212 (9)	0.0039 (8)
C7	0.0442 (10)	0.0363 (9)	0.0395 (9)	−0.0073 (7)	0.0204 (8)	−0.0038 (7)
C8	0.0413 (9)	0.0289 (8)	0.0556 (11)	0.0005 (7)	0.0239 (9)	−0.0021 (8)
C9	0.0425 (9)	0.0316 (8)	0.0358 (9)	−0.0020 (7)	0.0153 (8)	−0.0045 (7)
C10	0.0442 (10)	0.0454 (10)	0.0447 (11)	−0.0050 (8)	0.0123 (9)	−0.0015 (8)
C11	0.0578 (12)	0.0486 (11)	0.0391 (10)	−0.0002 (9)	0.0086 (9)	0.0007 (9)
C12	0.0700 (13)	0.0355 (9)	0.0435 (11)	0.0047 (9)	0.0286 (10)	0.0030 (8)
C13	0.0528 (11)	0.0438 (10)	0.0589 (12)	−0.0018 (9)	0.0292 (10)	0.0052 (9)
C14	0.0428 (10)	0.0417 (10)	0.0425 (10)	−0.0033 (8)	0.0143 (8)	0.0022 (8)
C15	0.0680 (13)	0.0418 (10)	0.0543 (12)	−0.0053 (10)	0.0240 (11)	−0.0157 (9)
C16	0.0498 (10)	0.0395 (9)	0.0400 (10)	−0.0036 (8)	0.0219 (8)	−0.0034 (8)
C17	0.0870 (16)	0.0565 (13)	0.0506 (12)	−0.0205 (12)	0.0395 (12)	−0.0065 (10)
C18	0.1041 (19)	0.0679 (15)	0.0417 (12)	−0.0056 (14)	0.0385 (13)	−0.0044 (11)
C19	0.0510 (11)	0.0640 (13)	0.0403 (11)	0.0042 (10)	0.0146 (9)	−0.0157 (10)
C20	0.0584 (13)	0.0781 (16)	0.0545 (13)	−0.0249 (12)	0.0268 (11)	−0.0228 (12)
C21	0.0655 (13)	0.0656 (13)	0.0428 (11)	−0.0235 (11)	0.0270 (10)	−0.0106 (10)
Cl1	0.1104 (5)	0.0655 (4)	0.0658 (4)	0.0146 (3)	0.0494 (4)	0.0240 (3)
Cl2	0.0677 (4)	0.1129 (6)	0.0483 (3)	0.0084 (4)	0.0094 (3)	−0.0332 (3)
N1	0.0474 (9)	0.0284 (7)	0.0358 (8)	−0.0031 (6)	0.0170 (7)	−0.0040 (6)
O1	0.0632 (9)	0.0357 (7)	0.0738 (10)	−0.0121 (6)	0.0328 (8)	−0.0032 (7)

Geometric parameters (Å, º) top

C1—N1	1.469 (2)	C10—C11	1.389 (3)
C1—C9	1.513 (2)	C10—H10	0.9300
C1—C2	1.565 (2)	C11—C12	1.370 (3)
C1—H1	0.9800	C11—H11	0.9300
C2—C8	1.516 (3)	C12—C13	1.373 (3)
C2—C15	1.527 (3)	C12—Cl1	1.744 (2)
C2—C3	1.554 (3)	C13—C14	1.382 (3)
C3—C4	1.524 (3)	C13—H13	0.9300
C3—H3A	0.9700	C14—H14	0.9300
C3—H3B	0.9700	C15—H15A	0.9600
C4—C5	1.529 (3)	C15—H15B	0.9600
C4—H4A	0.9700	C15—H15C	0.9600
C4—H4B	0.9700	C16—C21	1.377 (3)
C5—C6	1.533 (3)	C16—C17	1.384 (3)
C5—H5A	0.9700	C17—C18	1.386 (3)
C5—H5B	0.9700	C17—H17	0.9300
C6—C8	1.498 (3)	C18—C19	1.363 (3)
C6—C7	1.553 (3)	C18—H18	0.9300
C6—H6	0.9800	C19—C20	1.364 (3)
C7—N1	1.460 (2)	C19—Cl2	1.747 (2)
C7—C16	1.515 (2)	C20—C21	1.389 (3)
C7—H7	0.9800	C20—H20	0.9300
C8—O1	1.217 (2)	C21—H21	0.9300
C9—C10	1.389 (3)	N1—H1A	0.87 (2)
C9—C14	1.391 (3)

N1—C1—C9	110.30 (13)	C10—C9—C14	117.55 (17)
N1—C1—C2	111.38 (14)	C10—C9—C1	120.56 (16)
C9—C1—C2	111.78 (14)	C14—C9—C1	121.83 (16)
N1—C1—H1	107.7	C11—C10—C9	121.37 (18)
C9—C1—H1	107.7	C11—C10—H10	119.3
C2—C1—H1	107.7	C9—C10—H10	119.3
C8—C2—C15	111.32 (15)	C12—C11—C10	119.18 (18)
C8—C2—C3	104.31 (15)	C12—C11—H11	120.4
C15—C2—C3	109.74 (16)	C10—C11—H11	120.4
C8—C2—C1	106.57 (14)	C11—C12—C13	121.07 (18)
C15—C2—C1	109.68 (15)	C11—C12—Cl1	119.56 (16)
C3—C2—C1	115.08 (14)	C13—C12—Cl1	119.36 (16)
C4—C3—C2	115.70 (16)	C12—C13—C14	119.27 (19)
C4—C3—H3A	108.4	C12—C13—H13	120.4
C2—C3—H3A	108.4	C14—C13—H13	120.4
C4—C3—H3B	108.4	C13—C14—C9	121.50 (18)
C2—C3—H3B	108.4	C13—C14—H14	119.3
H3A—C3—H3B	107.4	C9—C14—H14	119.3
C3—C4—C5	112.12 (17)	C2—C15—H15A	109.5
C3—C4—H4A	109.2	C2—C15—H15B	109.5
C5—C4—H4A	109.2	H15A—C15—H15B	109.5
C3—C4—H4B	109.2	C2—C15—H15C	109.5
C5—C4—H4B	109.2	H15A—C15—H15C	109.5
H4A—C4—H4B	107.9	H15B—C15—H15C	109.5
C4—C5—C6	113.87 (16)	C21—C16—C17	118.09 (18)
C4—C5—H5A	108.8	C21—C16—C7	122.73 (17)
C6—C5—H5A	108.8	C17—C16—C7	119.16 (17)
C4—C5—H5B	108.8	C16—C17—C18	121.1 (2)
C6—C5—H5B	108.8	C16—C17—H17	119.5
H5A—C5—H5B	107.7	C18—C17—H17	119.5
C8—C6—C5	107.78 (16)	C19—C18—C17	119.4 (2)
C8—C6—C7	108.41 (15)	C19—C18—H18	120.3
C5—C6—C7	115.04 (15)	C17—C18—H18	120.3
C8—C6—H6	108.5	C18—C19—C20	120.96 (19)
C5—C6—H6	108.5	C18—C19—Cl2	119.73 (18)
C7—C6—H6	108.5	C20—C19—Cl2	119.29 (18)
N1—C7—C16	111.94 (14)	C19—C20—C21	119.4 (2)
N1—C7—C6	109.61 (15)	C19—C20—H20	120.3
C16—C7—C6	110.16 (15)	C21—C20—H20	120.3
N1—C7—H7	108.3	C16—C21—C20	121.0 (2)
C16—C7—H7	108.3	C16—C21—H21	119.5
C6—C7—H7	108.3	C20—C21—H21	119.5
O1—C8—C6	122.90 (18)	C7—N1—C1	113.28 (13)
O1—C8—C2	123.91 (18)	C7—N1—H1A	109.6 (13)
C6—C8—C2	113.12 (14)	C1—N1—H1A	106.6 (14)

N1—C1—C2—C8	−54.97 (18)	C2—C1—C9—C14	79.6 (2)
C9—C1—C2—C8	−178.85 (14)	C14—C9—C10—C11	−1.7 (3)
N1—C1—C2—C15	−175.58 (15)	C1—C9—C10—C11	175.53 (17)
C9—C1—C2—C15	60.54 (19)	C9—C10—C11—C12	−0.3 (3)
N1—C1—C2—C3	60.1 (2)	C10—C11—C12—C13	2.1 (3)
C9—C1—C2—C3	−63.8 (2)	C10—C11—C12—Cl1	−178.40 (15)
C8—C2—C3—C4	54.2 (2)	C11—C12—C13—C14	−1.7 (3)
C15—C2—C3—C4	173.54 (17)	Cl1—C12—C13—C14	178.79 (15)
C1—C2—C3—C4	−62.2 (2)	C12—C13—C14—C9	−0.5 (3)
C2—C3—C4—C5	−46.7 (2)	C10—C9—C14—C13	2.1 (3)
C3—C4—C5—C6	44.8 (2)	C1—C9—C14—C13	−175.09 (17)
C4—C5—C6—C8	−52.9 (2)	N1—C7—C16—C21	13.9 (3)
C4—C5—C6—C7	68.2 (2)	C6—C7—C16—C21	−108.3 (2)
C8—C6—C7—N1	57.08 (19)	N1—C7—C16—C17	−167.77 (18)
C5—C6—C7—N1	−63.6 (2)	C6—C7—C16—C17	70.0 (2)
C8—C6—C7—C16	−179.33 (15)	C21—C16—C17—C18	3.2 (4)
C5—C6—C7—C16	60.0 (2)	C7—C16—C17—C18	−175.2 (2)
C5—C6—C8—O1	−111.7 (2)	C16—C17—C18—C19	−1.9 (4)
C7—C6—C8—O1	123.23 (19)	C17—C18—C19—C20	−1.0 (4)
C5—C6—C8—C2	65.39 (19)	C17—C18—C19—Cl2	−179.72 (19)
C7—C6—C8—C2	−59.72 (19)	C18—C19—C20—C21	2.4 (4)
C15—C2—C8—O1	−5.7 (3)	Cl2—C19—C20—C21	−178.89 (18)
C3—C2—C8—O1	112.63 (19)	C17—C16—C21—C20	−1.8 (3)
C1—C2—C8—O1	−125.20 (18)	C7—C16—C21—C20	176.5 (2)
C15—C2—C8—C6	177.33 (16)	C19—C20—C21—C16	−0.9 (4)
C3—C2—C8—C6	−64.39 (18)	C16—C7—N1—C1	179.17 (14)
C1—C2—C8—C6	57.77 (19)	C6—C7—N1—C1	−58.29 (19)
N1—C1—C9—C10	137.96 (17)	C9—C1—N1—C7	−176.97 (14)
C2—C1—C9—C10	−97.55 (19)	C2—C1—N1—C7	58.32 (19)
N1—C1—C9—C14	−44.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.87 (2)	2.45 (2)	3.309 (2)	170.2 (18)

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁Cl₂NO
M_r	374.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	28.4515 (14), 7.0380 (3), 21.2771 (12)
β (°)	117.148 (4)
V (Å³)	3791.2 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.58 × 0.42 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.822, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	24985, 4661, 3149
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.125, 1.02
No. of reflections	4661
No. of parameters	231
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.43

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).