2,6-Bis(4-chloro­phen­yl)-1,3-dimethyl­piperidin-4-one O-benzyl­oxime

Park, D.H.; Ramkumar, V.; Parthiban, P.

doi:10.1107/S1600536812002152

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o525

doi:10.1107/S1600536812002152

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2,6-Bis(4-chlorophenyl)-1,3-dimethylpiperidin-4-one O-benzyloxime

Dong Ho Park,^a V. Ramkumar ^b and P. Parthiban ^a ^*

^aDepartment of Biomedicinal Chemistry, Inje University, Gimhae, Gyeongnam 621 749, Republic of Korea, and ^bDepartment of Chemistry, IIT Madras, Chennai 600 036, TamilNadu, India
^*Correspondence e-mail: parthisivam@yahoo.co.in

(Received 9 January 2012; accepted 18 January 2012; online 25 January 2012)

The piperidin-4-one ring in the title compound, C₂₆H₂₆Cl₂N₂O, exists in a chair conformation with equatorial orientations of the methyl and 4-chlorophenyl groups. The C atom bonded to the oxime group is statistically planar (bond-angle sum = 360.0°) although the C—C=N bond angles are very different [117.83 (15) and 127.59 (15)°]. The dihedral angle between the chlorophenyl rings is 54.75 (4)°. In the crystal, molecules interact via van der Waals forces.

Related literature

For the synthesis and biological activity of piperidin-4-one derivatives, see: Parthiban et al. (2008 ). For related structures see: Parthiban et al. (2009a ,b ). For ring puckering parameters, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₆H₂₆Cl₂N₂O
M_r = 453.39
Monoclinic, P 2₁ /n
a = 7.6461 (2) Å
b = 18.5051 (5) Å
c = 16.7172 (5) Å
β = 91.130 (1)°
V = 2364.89 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 298 K
0.23 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.935, T_max = 0.957
32534 measured reflections
7702 independent reflections
4010 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.152
S = 1.02
7702 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002152/hb6599sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002152/hb6599Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002152/hb6599Isup3.cml

checkCIF report

Comment top

The piperidin-4-one nucleus is an important class of pharmacophore due to its broad spectrum of biological actions ranging from antibacterial to anticancer (e.g. Parthiban et al., 2009a). On account of its biological significance, isolaton from the natural products as well as synthesis of new molecules, and their stereochemical analysis are considered as important in the field of medicinal chemistry. Hence, we synthesized the title compound by a successive double Mannich condensation and thus obtained piperidin-4-one was further condensed with O-benzylhydroxylamine to make the oxime ether derivative of the piperidone. Thus the obtained crystal of the unsymmetrical molecule was undertaken for this study to explore its stereochemistry in the solid-state, since the E/Z isomerization plays a mjor role during oximation.

The crystallographic analysis of the title compound indicated that the piperidone ring N1—C1—C2—C3—C4—C5 adopts a chair conformation with the deviation of ring atoms N1 and C3 from the best plane C1—C2—C4—C5 by -0.593 and 0.683 Å, respectively. According to Nardelli (Nardelli, 1983), the smallest displacement asymmetry parameters q₂ and q₃ are 0.067 (17) and 0.557 (18) Å, respectively. According to Cremer and Pople (Cremer & Pople, 1975), the ring puckering parameters such as total puckering amplitude Q_T and phase angle θ are 0.560 (18) Å and 6.74 (17)°. Thus, all parameters strongly support the near ideal chair conformation for the piperidone ring.

The torsion angles of C3—C2—C1—C6 and C3—C4—C5—C20 of the 4-chlorophenyl rings are 176 (3) and 178.6 (3)° and they are orientated at an angle of 54.75 (4)° with respect to one another. In the crystal, the molecules interact by van der Waals' forces.

Related literature top

For the synthesis and biological activity of piperidin-4-one derivatives, see: Parthiban et al. (2008). For related structures see: Parthiban et al. (2009a,b). For ring puckering parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

The 2,6-bis(4-chlorophenyl)-1,3-dimethylpiperidin-4-one O-benzyloxime was synthesized by one-pot using 4-chlorobenzaldehyde (0.1 mol, 14.06 g), butan-2-one (0.05 mol, 3.61 g, 4.48 ml) and ammonium acetate (0.05 mol, 2.85 g) in a 50 ml of absolute ethanol. The mixture was gently warmed on a hot plate at 303–308 K (30–35° C) with moderate stirring till the complete consumption of the starting materials, which was monitored by TLC. At the end, the crude piperidin-4-one was separated by filtration and gently washed with 1:5 cold ethanol-ether mixture. Then the pure product was N-methylated by methyl iodide using anhydrous potasssium carbonate in dry acetone. Thus the obtained N-methylpiperidin-4-one was condensed with O-benzylhydroxylamine hydrochloride using sodium acetate trihydrate as a base in ethanol (Parthiban et al. (2008, 2009b). Colourless blocks of the title compound were obtained by slow evaporation from ethanol.

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).

Figures top

Fig. 1. Anistropic displacement representation of the title molecule with atoms represented with 30% probability ellipsoids.

2,6-Bis(4-chlorophenyl)-1,3-dimethylpiperidin-4-one O-benzyloxime top

Crystal data top

C₂₆H₂₆Cl₂N₂O	F(000) = 952
M_r = 453.39	D_x = 1.273 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6502 reflections
a = 7.6461 (2) Å	θ = 2.4–25.0°
b = 18.5051 (5) Å	µ = 0.30 mm⁻¹
c = 16.7172 (5) Å	T = 298 K
β = 91.130 (1)°	Block, colourless
V = 2364.89 (11) Å³	0.23 × 0.19 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	7702 independent reflections
Radiation source: fine-focus sealed tube	4010 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 31.4°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→11
T_min = 0.935, T_max = 0.957	k = −27→27
32534 measured reflections	l = −24→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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0637P)² + 0.3655P] where P = (F_o² + 2F_c²)/3
7702 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₆H₂₆Cl₂N₂O	V = 2364.89 (11) Å³
M_r = 453.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.6461 (2) Å	µ = 0.30 mm⁻¹
b = 18.5051 (5) Å	T = 298 K
c = 16.7172 (5) Å	0.23 × 0.19 × 0.15 mm
β = 91.130 (1)°

Data collection top

Bruker APEXII CCD diffractometer	7702 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4010 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.957	R_int = 0.037
32534 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.02	Δρ_max = 0.28 e Å⁻³
7702 reflections	Δρ_min = −0.21 e Å⁻³
282 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	0.42343 (19)	0.32793 (8)	0.56014 (10)	0.0414 (4)
H1	0.4723	0.3293	0.5064	0.050*
C2	0.2500 (2)	0.37081 (9)	0.55816 (11)	0.0445 (4)
H2	0.2058	0.3719	0.6128	0.053*
C3	0.1169 (2)	0.33229 (9)	0.50667 (11)	0.0448 (4)
C4	0.0966 (2)	0.25380 (10)	0.52509 (13)	0.0545 (5)
H4A	0.0192	0.2315	0.4856	0.065*
H4B	0.0450	0.2481	0.5773	0.065*
C5	0.2753 (2)	0.21664 (9)	0.52438 (11)	0.0466 (4)
H5	0.3232	0.2220	0.4708	0.056*
C6	0.55190 (19)	0.36477 (8)	0.61703 (10)	0.0402 (4)
C7	0.7020 (2)	0.39609 (10)	0.58833 (11)	0.0500 (4)
H7	0.7268	0.3920	0.5343	0.060*
C8	0.8164 (2)	0.43352 (10)	0.63860 (12)	0.0537 (5)
H8	0.9169	0.4545	0.6184	0.064*
C9	0.7802 (2)	0.43934 (9)	0.71775 (11)	0.0477 (4)
C10	0.6325 (2)	0.40840 (10)	0.74877 (11)	0.0524 (4)
H10	0.6090	0.4123	0.8030	0.063*
C11	0.5195 (2)	0.37142 (10)	0.69761 (11)	0.0498 (4)
H11	0.4193	0.3505	0.7181	0.060*
C12	0.2795 (2)	0.44860 (9)	0.53218 (13)	0.0585 (5)
H12A	0.3313	0.4491	0.4803	0.088*
H12B	0.3563	0.4721	0.5701	0.088*
H12C	0.1695	0.4736	0.5297	0.088*
C13	−0.1626 (3)	0.36716 (12)	0.34792 (13)	0.0639 (5)
H13A	−0.0839	0.3650	0.3032	0.077*
H13B	−0.1769	0.4173	0.3632	0.077*
C14	−0.3364 (2)	0.33482 (9)	0.32492 (10)	0.0451 (4)
C15	−0.4831 (3)	0.37759 (12)	0.32269 (13)	0.0614 (5)
H15	−0.4736	0.4264	0.3351	0.074*
C16	−0.6439 (3)	0.34904 (18)	0.30229 (18)	0.0930 (9)
H16	−0.7421	0.3787	0.3005	0.112*
C17	−0.6596 (4)	0.2789 (2)	0.28508 (19)	0.1076 (11)
H17	−0.7687	0.2597	0.2717	0.129*
C18	−0.5152 (5)	0.23537 (15)	0.28717 (18)	0.1031 (10)
H18	−0.5264	0.1865	0.2754	0.124*
C19	−0.3534 (3)	0.26358 (12)	0.30663 (15)	0.0745 (6)
H19	−0.2554	0.2338	0.3073	0.089*
C20	0.2544 (2)	0.13702 (9)	0.54100 (11)	0.0461 (4)
C21	0.1951 (3)	0.11215 (10)	0.61296 (12)	0.0601 (5)
H21	0.1680	0.1452	0.6528	0.072*
C22	0.1750 (3)	0.03941 (10)	0.62753 (13)	0.0611 (5)
H22	0.1356	0.0234	0.6768	0.073*
C23	0.2136 (2)	−0.00899 (9)	0.56869 (12)	0.0513 (5)
C24	0.2715 (3)	0.01343 (10)	0.49649 (13)	0.0579 (5)
H24	0.2967	−0.0200	0.4568	0.069*
C25	0.2924 (2)	0.08673 (10)	0.48284 (12)	0.0538 (4)
H25	0.3328	0.1023	0.4337	0.065*
C26	0.5667 (2)	0.21413 (11)	0.58121 (14)	0.0665 (6)
H26A	0.5517	0.1649	0.5980	0.100*
H26B	0.6474	0.2380	0.6171	0.100*
H26C	0.6116	0.2150	0.5280	0.100*
N1	0.39675 (17)	0.25164 (7)	0.58210 (9)	0.0436 (3)
N2	0.03573 (17)	0.36870 (8)	0.45354 (9)	0.0483 (4)
O1	−0.09336 (16)	0.32633 (7)	0.41361 (8)	0.0594 (4)
Cl1	0.92535 (7)	0.48578 (3)	0.78064 (4)	0.07529 (19)
Cl2	0.19251 (8)	−0.10122 (3)	0.58698 (4)	0.0769 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0416 (8)	0.0420 (9)	0.0404 (10)	0.0022 (6)	−0.0017 (7)	0.0006 (7)
C2	0.0414 (8)	0.0415 (9)	0.0502 (11)	0.0025 (6)	−0.0042 (7)	0.0001 (7)
C3	0.0390 (8)	0.0437 (9)	0.0515 (11)	0.0023 (6)	−0.0046 (7)	0.0026 (8)
C4	0.0500 (9)	0.0464 (10)	0.0663 (13)	−0.0052 (7)	−0.0168 (8)	0.0068 (9)
C5	0.0552 (9)	0.0434 (9)	0.0409 (10)	−0.0009 (7)	−0.0062 (8)	0.0000 (7)
C6	0.0374 (7)	0.0412 (9)	0.0418 (10)	0.0023 (6)	−0.0009 (7)	0.0025 (7)
C7	0.0435 (8)	0.0630 (11)	0.0436 (11)	−0.0010 (7)	0.0040 (7)	0.0033 (8)
C8	0.0383 (8)	0.0656 (12)	0.0572 (13)	−0.0093 (7)	0.0001 (8)	0.0096 (9)
C9	0.0461 (8)	0.0442 (9)	0.0521 (12)	−0.0036 (7)	−0.0125 (8)	0.0054 (8)
C10	0.0549 (10)	0.0620 (11)	0.0401 (10)	−0.0060 (8)	−0.0024 (8)	0.0024 (8)
C11	0.0453 (9)	0.0592 (11)	0.0449 (11)	−0.0096 (7)	0.0027 (7)	0.0052 (8)
C12	0.0523 (10)	0.0420 (9)	0.0806 (15)	0.0003 (8)	−0.0111 (9)	0.0008 (9)
C13	0.0535 (10)	0.0740 (14)	0.0634 (14)	−0.0084 (9)	−0.0160 (9)	0.0198 (11)
C14	0.0466 (8)	0.0503 (10)	0.0382 (10)	−0.0013 (7)	−0.0065 (7)	0.0043 (8)
C15	0.0599 (11)	0.0626 (12)	0.0615 (14)	0.0067 (9)	−0.0031 (9)	−0.0003 (10)
C16	0.0477 (11)	0.123 (2)	0.108 (2)	0.0021 (13)	−0.0107 (12)	0.0303 (18)
C17	0.0874 (19)	0.133 (3)	0.101 (2)	−0.0501 (19)	−0.0415 (16)	0.033 (2)
C18	0.140 (3)	0.0683 (16)	0.100 (2)	−0.0419 (18)	−0.0212 (19)	−0.0091 (15)
C19	0.0850 (15)	0.0540 (12)	0.0843 (18)	0.0041 (11)	−0.0014 (13)	−0.0030 (11)
C20	0.0525 (9)	0.0421 (9)	0.0433 (11)	0.0008 (7)	−0.0084 (8)	−0.0030 (8)
C21	0.0899 (14)	0.0454 (10)	0.0451 (12)	0.0020 (9)	0.0042 (10)	−0.0079 (9)
C22	0.0856 (14)	0.0463 (11)	0.0517 (13)	0.0003 (9)	0.0085 (10)	0.0008 (9)
C23	0.0512 (9)	0.0381 (9)	0.0645 (13)	0.0019 (7)	−0.0047 (9)	−0.0020 (8)
C24	0.0670 (11)	0.0476 (10)	0.0590 (13)	0.0039 (8)	0.0014 (10)	−0.0141 (9)
C25	0.0634 (11)	0.0513 (11)	0.0466 (11)	0.0017 (8)	0.0005 (9)	−0.0015 (9)
C26	0.0542 (10)	0.0541 (11)	0.0904 (17)	0.0145 (8)	−0.0181 (10)	−0.0080 (11)
N1	0.0446 (7)	0.0390 (7)	0.0470 (9)	0.0029 (5)	−0.0086 (6)	−0.0018 (6)
N2	0.0398 (7)	0.0491 (8)	0.0557 (10)	−0.0008 (6)	−0.0079 (6)	0.0019 (7)
O1	0.0562 (7)	0.0554 (8)	0.0658 (9)	−0.0072 (6)	−0.0249 (6)	0.0111 (6)
Cl1	0.0766 (3)	0.0786 (4)	0.0696 (4)	−0.0275 (3)	−0.0249 (3)	0.0053 (3)
Cl2	0.0885 (4)	0.0405 (3)	0.1022 (5)	−0.0008 (2)	0.0140 (3)	−0.0008 (3)

Geometric parameters (Å, º) top

C1—N1	1.474 (2)	C13—C14	1.500 (2)
C1—C6	1.516 (2)	C13—H13A	0.9700
C1—C2	1.545 (2)	C13—H13B	0.9700
C1—H1	0.9800	C14—C19	1.359 (3)
C2—C3	1.500 (2)	C14—C15	1.373 (3)
C2—C12	1.522 (2)	C15—C16	1.375 (3)
C2—H2	0.9800	C15—H15	0.9300
C3—N2	1.268 (2)	C16—C17	1.334 (4)
C3—C4	1.493 (2)	C16—H16	0.9300
C4—C5	1.529 (2)	C17—C18	1.367 (4)
C4—H4A	0.9700	C17—H17	0.9300
C4—H4B	0.9700	C18—C19	1.376 (4)
C5—N1	1.476 (2)	C18—H18	0.9300
C5—C20	1.508 (2)	C19—H19	0.9300
C5—H5	0.9800	C20—C21	1.373 (3)
C6—C7	1.380 (2)	C20—C25	1.381 (2)
C6—C11	1.380 (3)	C21—C22	1.377 (3)
C7—C8	1.387 (3)	C21—H21	0.9300
C7—H7	0.9300	C22—C23	1.367 (3)
C8—C9	1.361 (3)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.359 (3)
C9—C10	1.377 (2)	C23—Cl2	1.7420 (18)
C9—Cl1	1.7405 (17)	C24—C25	1.385 (3)
C10—C11	1.384 (2)	C24—H24	0.9300
C10—H10	0.9300	C25—H25	0.9300
C11—H11	0.9300	C26—N1	1.473 (2)
C12—H12A	0.9600	C26—H26A	0.9600
C12—H12B	0.9600	C26—H26B	0.9600
C12—H12C	0.9600	C26—H26C	0.9600
C13—O1	1.426 (2)	N2—O1	1.4172 (17)

N1—C1—C6	111.45 (13)	O1—C13—H13A	110.2
N1—C1—C2	111.98 (13)	C14—C13—H13A	110.2
C6—C1—C2	109.13 (13)	O1—C13—H13B	110.2
N1—C1—H1	108.0	C14—C13—H13B	110.2
C6—C1—H1	108.0	H13A—C13—H13B	108.5
C2—C1—H1	108.0	C19—C14—C15	118.59 (18)
C3—C2—C12	112.86 (14)	C19—C14—C13	121.68 (18)
C3—C2—C1	109.90 (13)	C15—C14—C13	119.73 (17)
C12—C2—C1	111.10 (14)	C14—C15—C16	120.8 (2)
C3—C2—H2	107.6	C14—C15—H15	119.6
C12—C2—H2	107.6	C16—C15—H15	119.6
C1—C2—H2	107.6	C17—C16—C15	120.2 (2)
N2—C3—C4	127.59 (15)	C17—C16—H16	119.9
N2—C3—C2	117.83 (15)	C15—C16—H16	119.9
C4—C3—C2	114.58 (14)	C16—C17—C18	120.0 (2)
C3—C4—C5	109.83 (14)	C16—C17—H17	120.0
C3—C4—H4A	109.7	C18—C17—H17	120.0
C5—C4—H4A	109.7	C17—C18—C19	120.3 (2)
C3—C4—H4B	109.7	C17—C18—H18	119.9
C5—C4—H4B	109.7	C19—C18—H18	119.9
H4A—C4—H4B	108.2	C14—C19—C18	120.2 (2)
N1—C5—C20	112.08 (13)	C14—C19—H19	119.9
N1—C5—C4	110.38 (14)	C18—C19—H19	119.9
C20—C5—C4	109.87 (14)	C21—C20—C25	117.94 (16)
N1—C5—H5	108.1	C21—C20—C5	121.79 (16)
C20—C5—H5	108.1	C25—C20—C5	120.27 (17)
C4—C5—H5	108.1	C20—C21—C22	121.51 (18)
C7—C6—C11	117.92 (16)	C20—C21—H21	119.2
C7—C6—C1	120.25 (16)	C22—C21—H21	119.2
C11—C6—C1	121.74 (14)	C23—C22—C21	119.12 (19)
C6—C7—C8	121.20 (17)	C23—C22—H22	120.4
C6—C7—H7	119.4	C21—C22—H22	120.4
C8—C7—H7	119.4	C24—C23—C22	121.20 (17)
C9—C8—C7	119.39 (16)	C24—C23—Cl2	119.21 (15)
C9—C8—H8	120.3	C22—C23—Cl2	119.58 (16)
C7—C8—H8	120.3	C23—C24—C25	119.08 (18)
C8—C9—C10	121.14 (16)	C23—C24—H24	120.5
C8—C9—Cl1	119.13 (13)	C25—C24—H24	120.5
C10—C9—Cl1	119.72 (15)	C20—C25—C24	121.15 (19)
C9—C10—C11	118.64 (17)	C20—C25—H25	119.4
C9—C10—H10	120.7	C24—C25—H25	119.4
C11—C10—H10	120.7	N1—C26—H26A	109.5
C6—C11—C10	121.70 (16)	N1—C26—H26B	109.5
C6—C11—H11	119.2	H26A—C26—H26B	109.5
C10—C11—H11	119.2	N1—C26—H26C	109.5
C2—C12—H12A	109.5	H26A—C26—H26C	109.5
C2—C12—H12B	109.5	H26B—C26—H26C	109.5
H12A—C12—H12B	109.5	C26—N1—C1	108.81 (13)
C2—C12—H12C	109.5	C26—N1—C5	109.30 (13)
H12A—C12—H12C	109.5	C1—N1—C5	110.24 (12)
H12B—C12—H12C	109.5	C3—N2—O1	111.28 (13)
O1—C13—C14	107.43 (15)	N2—O1—C13	108.31 (13)

N1—C1—C2—C3	−52.12 (19)	C15—C16—C17—C18	−0.5 (5)
C6—C1—C2—C3	−176.00 (14)	C16—C17—C18—C19	−0.3 (5)
N1—C1—C2—C12	−177.75 (15)	C15—C14—C19—C18	−0.6 (3)
C6—C1—C2—C12	58.36 (19)	C13—C14—C19—C18	178.8 (2)
C12—C2—C3—N2	−5.6 (2)	C17—C18—C19—C14	0.8 (4)
C1—C2—C3—N2	−130.26 (16)	N1—C5—C20—C21	58.7 (2)
C12—C2—C3—C4	174.34 (16)	C4—C5—C20—C21	−64.4 (2)
C1—C2—C3—C4	49.7 (2)	N1—C5—C20—C25	−122.32 (17)
N2—C3—C4—C5	127.31 (19)	C4—C5—C20—C25	114.57 (19)
C2—C3—C4—C5	−52.7 (2)	C25—C20—C21—C22	0.4 (3)
C3—C4—C5—N1	57.3 (2)	C5—C20—C21—C22	179.46 (18)
C3—C4—C5—C20	−178.63 (15)	C20—C21—C22—C23	−0.5 (3)
N1—C1—C6—C7	121.89 (17)	C21—C22—C23—C24	0.1 (3)
C2—C1—C6—C7	−113.91 (17)	C21—C22—C23—Cl2	178.84 (16)
N1—C1—C6—C11	−61.4 (2)	C22—C23—C24—C25	0.4 (3)
C2—C1—C6—C11	62.8 (2)	Cl2—C23—C24—C25	−178.37 (15)
C11—C6—C7—C8	−0.4 (3)	C21—C20—C25—C24	0.0 (3)
C1—C6—C7—C8	176.39 (16)	C5—C20—C25—C24	−178.99 (16)
C6—C7—C8—C9	0.1 (3)	C23—C24—C25—C20	−0.5 (3)
C7—C8—C9—C10	0.3 (3)	C6—C1—N1—C26	−58.49 (18)
C7—C8—C9—Cl1	179.50 (14)	C2—C1—N1—C26	178.93 (15)
C8—C9—C10—C11	−0.5 (3)	C6—C1—N1—C5	−178.34 (13)
Cl1—C9—C10—C11	−179.66 (14)	C2—C1—N1—C5	59.08 (18)
C7—C6—C11—C10	0.2 (3)	C20—C5—N1—C26	56.2 (2)
C1—C6—C11—C10	−176.52 (16)	C4—C5—N1—C26	179.07 (15)
C9—C10—C11—C6	0.2 (3)	C20—C5—N1—C1	175.80 (14)
O1—C13—C14—C19	−55.0 (3)	C4—C5—N1—C1	−61.38 (18)
O1—C13—C14—C15	124.4 (2)	C4—C3—N2—O1	4.0 (3)
C19—C14—C15—C16	−0.1 (3)	C2—C3—N2—O1	−176.00 (14)
C13—C14—C15—C16	−179.6 (2)	C3—N2—O1—C13	−172.17 (17)
C14—C15—C16—C17	0.6 (4)	C14—C13—O1—N2	−160.21 (15)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₆Cl₂N₂O
M_r	453.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.6461 (2), 18.5051 (5), 16.7172 (5)
β (°)	91.130 (1)
V (Å³)	2364.89 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.23 × 0.19 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.935, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	32534, 7702, 4010
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.732

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.152, 1.02
No. of reflections	7702
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.21

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

Acknowledgements

This research was supported by the BK21.

References

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