2-[2,6-Bis(2-chloro­phen­yl)piperidin-4-yl­idene]malononitrile

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

doi:10.1107/S1600536807060059

2-[2,6-Bis(2-chlorophenyl)piperidin-4-ylidene]malononitrile

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

The piperidine ring of the title molecule, C₂₀H₁₅Cl₂N₃, is in a chair form. The dihedral angle between the two chlorophenyl rings is 38.4 (1)°. The benzene rings are in equatorial orientations. The malononitrile group is planar. Intramolecular C—H

Cl and C—H

N hydrogen bonds are found in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060059/rk2063sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060059/rk2063Isup2.hkl Contains datablock I

CCDC reference: 673048

checkCIF report

Key indicators

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
R factor = 0.041
wR factor = 0.124
Data-to-parameter ratio = 26.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         35 Perc.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C14    -   C15    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C14    -   C17    ...       1.44 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

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

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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 t3-benzyl-r2,c6-diarylpiperidin-4-one and its derivatives. Manimekalai et al. (2000) have reported ¹³C– and ¹H-NMR spectral studies of some t3-carboxyethyl-r2,c6-diphenylpiperidine derivatives. Thiruvalluvar et al. (2007) have reported a crystal structure of 3-ethyl-2,6-diphenylpiperidin-4-ol wherein the piperidine ring is in chair form. The piperidine ring of the title molecule, C₂₀H₁₅Cl₂N₃, is in chair form too. The dihedral angle between the two chlorophenyl rings is 38.4 (1)°. The phenyl rings at 2 and 6 positions are in equatorial orientations. The malononitrile group at position 4 has a coplanar orientation. Weak C—H···Cl and C—H···N intramolecular hydrogen bonds are found in the crystal structure.

Related literature top

For applications of piperidines, see: Jayabharathi et al. (2007); Manimekalai et al. 2000. For a related crystal structure, see: Thiruvalluvar et al. (2007).

Experimental top

2,6-bis(O-chlorophenyl)piperidin-4-one (3 mmol, 1 g), ammonium acetate (3 mmol, 0.256 g) and basic alumina (3 mmol, 3 g) and malononitrile (3 mmol, 0.02 g) were mixed thoroughly in a mortar. The reaction mixture was placed in a beaker and irradiated using microwave in a microwave oven operating at 2450 Hz (100% power, 850 W) for 3 minutes. The reaction mixture was extracted with dichloromethane followed by water. The product was recrystallized from ethanol. The yield of the isolated product was 0.42 g (60%).

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, 1997); 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 scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are shown as small spheres of arbitrary radius.

2-[2,6-Bis(2-chlorophenyl)piperidin-4-ylidene]malononitrile top

Crystal data top

C₂₀H₁₅Cl₂N₃	F(000) = 760
M_r = 368.25	D_x = 1.356 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 452 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.1732 (10) Å	Cell parameters from 3546 reflections
b = 7.5493 (5) Å	θ = 4.7–32.8°
c = 16.3452 (12) Å	µ = 0.37 mm⁻¹
β = 105.494 (7)°	T = 200 K
V = 1804.3 (2) Å³	Plate, pale yellow
Z = 4	0.51 × 0.44 × 0.21 mm

Data collection top

Oxford Diffraction Gemini diffractometer	6044 independent reflections
Radiation source: fine–focus sealed tube	2122 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 10.5081 pixels mm^-1	θ_max = 32.8°, θ_min = 4.7°
ϕ and ω scans	h = −22→21
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −11→11
T_min = 0.829, T_max = 0.926	l = −17→24
17148 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ²(F_o²) + (0.0517P)²] where P = (F_o² + 2F_c²)/3
6044 reflections	(Δ/σ)_max < 0.002
230 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₀H₁₅Cl₂N₃	V = 1804.3 (2) Å³
M_r = 368.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.1732 (10) Å	µ = 0.37 mm⁻¹
b = 7.5493 (5) Å	T = 200 K
c = 16.3452 (12) Å	0.51 × 0.44 × 0.21 mm
β = 105.494 (7)°

Data collection top

Oxford Diffraction Gemini diffractometer	6044 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2122 reflections with I > 2σ(I)
T_min = 0.829, T_max = 0.926	R_int = 0.050
17148 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	Δρ_max = 0.22 e Å⁻³
6044 reflections	Δρ_min = −0.32 e Å⁻³
230 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All s.u.'s are estimated from the variances of the (full) variance–covariance matrix. The cell s.u.'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 > 2σ(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
Cl1	0.51594 (3)	0.83403 (7)	0.09858 (4)	0.0614 (2)
Cl2	0.20649 (5)	0.40648 (8)	0.32315 (5)	0.0862 (3)
N1	0.27010 (10)	0.8856 (2)	0.19991 (11)	0.0415 (5)
N16	0.32725 (12)	0.4937 (3)	−0.09216 (11)	0.0692 (7)
N18	0.12217 (15)	0.2456 (3)	0.01170 (14)	0.0857 (9)
C2	0.33512 (11)	0.8643 (2)	0.14911 (11)	0.0391 (6)
C3	0.28114 (13)	0.8191 (2)	0.05805 (12)	0.0459 (6)
C4	0.22329 (11)	0.6593 (3)	0.05782 (12)	0.0432 (6)
C5	0.16425 (12)	0.6703 (3)	0.11789 (12)	0.0517 (7)
C6	0.22218 (11)	0.7209 (2)	0.20674 (11)	0.0416 (6)
C14	0.22543 (11)	0.5155 (3)	0.01047 (11)	0.0434 (6)
C15	0.28311 (13)	0.5028 (3)	−0.04622 (12)	0.0486 (7)
C17	0.16823 (14)	0.3631 (3)	0.01110 (13)	0.0554 (8)
C21	0.39066 (11)	1.0311 (2)	0.15015 (10)	0.0374 (6)
C22	0.47250 (12)	1.0308 (3)	0.12742 (11)	0.0429 (6)
C23	0.52285 (13)	1.1825 (3)	0.12783 (12)	0.0508 (7)
C24	0.49203 (13)	1.3408 (3)	0.15060 (13)	0.0547 (7)
C25	0.41203 (14)	1.3466 (3)	0.17392 (14)	0.0559 (7)
C26	0.36109 (12)	1.1931 (2)	0.17297 (12)	0.0476 (7)
C61	0.16153 (11)	0.7413 (3)	0.26566 (11)	0.0414 (6)
C62	0.14843 (12)	0.6070 (3)	0.31873 (12)	0.0472 (7)
C63	0.08924 (13)	0.6248 (3)	0.36937 (12)	0.0599 (8)
C64	0.04183 (13)	0.7797 (4)	0.36721 (13)	0.0651 (9)
C65	0.05376 (13)	0.9164 (3)	0.31606 (14)	0.0636 (8)
C66	0.11242 (12)	0.8965 (3)	0.26533 (13)	0.0535 (7)
H1	0.2970 (12)	0.917 (3)	0.2470 (12)	0.049 (6)*
H2	0.37742	0.76416	0.17265	0.0469*
H3A	0.24184	0.92063	0.03298	0.0550*
H3B	0.32408	0.79641	0.02306	0.0550*
H5A	0.13441	0.55450	0.12023	0.0620*
H5B	0.11581	0.76006	0.09739	0.0620*
H6	0.26803	0.62538	0.22874	0.0499*
H23	0.57886	1.17760	0.11236	0.0610*
H24	0.52616	1.44608	0.15019	0.0656*
H25	0.39118	1.45574	0.19082	0.0671*
H26	0.30499	1.19933	0.18823	0.0571*
H63	0.08152	0.53052	0.40532	0.0719*
H64	0.00043	0.79258	0.40135	0.0781*
H65	0.02166	1.02463	0.31559	0.0763*
H66	0.11943	0.99116	0.22929	0.0642*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0679 (3)	0.0520 (3)	0.0765 (4)	0.0007 (2)	0.0403 (3)	−0.0093 (3)
Cl2	0.1155 (5)	0.0572 (4)	0.1071 (5)	0.0202 (3)	0.0665 (4)	0.0268 (4)
N1	0.0461 (9)	0.0446 (10)	0.0375 (9)	−0.0067 (7)	0.0176 (8)	−0.0067 (9)
N16	0.0757 (12)	0.0742 (14)	0.0707 (12)	−0.0104 (10)	0.0422 (10)	−0.0109 (11)
N18	0.1039 (15)	0.0733 (14)	0.1018 (16)	−0.0402 (12)	0.0655 (13)	−0.0354 (13)
C2	0.0453 (10)	0.0367 (10)	0.0371 (10)	−0.0036 (8)	0.0143 (8)	−0.0019 (9)
C3	0.0547 (10)	0.0442 (11)	0.0428 (11)	−0.0087 (9)	0.0202 (9)	−0.0059 (10)
C4	0.0426 (10)	0.0504 (12)	0.0376 (10)	−0.0071 (8)	0.0123 (8)	−0.0057 (10)
C5	0.0494 (10)	0.0574 (13)	0.0557 (12)	−0.0130 (9)	0.0269 (10)	−0.0140 (11)
C6	0.0415 (9)	0.0411 (10)	0.0468 (11)	−0.0012 (8)	0.0197 (8)	−0.0005 (10)
C14	0.0467 (10)	0.0477 (12)	0.0376 (10)	−0.0066 (8)	0.0146 (8)	−0.0035 (10)
C15	0.0532 (11)	0.0473 (12)	0.0478 (11)	−0.0081 (9)	0.0179 (9)	−0.0096 (11)
C17	0.0639 (12)	0.0575 (14)	0.0542 (13)	−0.0150 (10)	0.0319 (10)	−0.0207 (12)
C21	0.0460 (10)	0.0353 (10)	0.0319 (9)	−0.0002 (8)	0.0123 (8)	0.0017 (9)
C22	0.0518 (10)	0.0400 (11)	0.0399 (10)	−0.0045 (8)	0.0176 (9)	−0.0044 (10)
C23	0.0515 (11)	0.0539 (13)	0.0493 (12)	−0.0107 (10)	0.0173 (9)	0.0012 (11)
C24	0.0613 (12)	0.0424 (12)	0.0571 (13)	−0.0134 (10)	0.0101 (10)	0.0045 (11)
C25	0.0664 (13)	0.0360 (11)	0.0638 (14)	−0.0008 (10)	0.0148 (10)	−0.0037 (11)
C26	0.0491 (10)	0.0413 (11)	0.0537 (13)	0.0024 (8)	0.0160 (9)	0.0010 (10)
C61	0.0369 (9)	0.0475 (11)	0.0411 (11)	−0.0007 (8)	0.0126 (8)	−0.0017 (10)
C62	0.0478 (10)	0.0481 (12)	0.0492 (12)	−0.0017 (9)	0.0191 (9)	0.0014 (11)
C63	0.0563 (12)	0.0814 (16)	0.0459 (12)	−0.0101 (11)	0.0202 (10)	0.0072 (13)
C64	0.0463 (12)	0.105 (2)	0.0506 (13)	0.0043 (12)	0.0242 (10)	−0.0030 (15)
C65	0.0535 (12)	0.0791 (17)	0.0619 (14)	0.0208 (11)	0.0220 (10)	−0.0030 (14)
C66	0.0526 (11)	0.0568 (13)	0.0553 (12)	0.0118 (10)	0.0215 (10)	0.0070 (12)

Geometric parameters (Å, º) top

Cl1—C22	1.741 (2)	C25—C26	1.391 (3)
Cl2—C62	1.743 (2)	C61—C66	1.388 (3)
N1—C2	1.458 (2)	C61—C62	1.383 (3)
N1—C6	1.460 (2)	C62—C63	1.381 (3)
N16—C15	1.134 (3)	C63—C64	1.368 (4)
N18—C17	1.131 (3)	C64—C65	1.370 (3)
N1—H1	0.81 (2)	C65—C66	1.377 (3)
C2—C21	1.513 (2)	C2—H2	1.0000
C2—C3	1.533 (3)	C3—H3A	0.9900
C3—C4	1.491 (3)	C3—H3B	0.9900
C4—C14	1.339 (3)	C5—H5A	0.9900
C4—C5	1.498 (3)	C5—H5B	0.9900
C5—C6	1.532 (3)	C6—H6	1.0000
C6—C61	1.507 (2)	C23—H23	0.9500
C14—C17	1.443 (3)	C24—H24	0.9500
C14—C15	1.438 (3)	C25—H25	0.9500
C21—C22	1.388 (3)	C26—H26	0.9500
C21—C26	1.388 (2)	C63—H63	0.9500
C22—C23	1.376 (3)	C64—H64	0.9500
C23—C24	1.371 (3)	C65—H65	0.9500
C24—C25	1.367 (3)	C66—H66	0.9500

Cl1···C3	3.447 (2)	C65···C63^xi	3.586 (3)
Cl1···C25ⁱ	3.586 (2)	C66···C15^x	3.537 (3)
Cl1···N16ⁱⁱ	3.454 (2)	C15···H3B	2.4900
Cl1···C23ⁱⁱⁱ	3.591 (2)	C17···H5A	2.4500
Cl1···H2	2.7400	C22···H3B	3.0100
Cl1···H3B	2.8600	C24···H2^viii	3.0900
Cl1···H24^iv	3.0400	C26···H1	2.72 (2)
Cl2···H6	2.6000	C62···H65^vi	2.9700
N16···C24ⁱⁱⁱ	3.375 (3)	C63···H3A^x	3.0500
N16···Cl1ⁱⁱ	3.454 (2)	C66···H1	2.899 (19)
N1···H66	2.5800	C66···H5B	2.9500
N1···H26	2.4500	H1···C26	2.72 (2)
N16···H23ⁱⁱⁱ	2.9200	H1···C66	2.899 (19)
N16···H24ⁱⁱⁱ	2.6800	H1···H26	2.3500
N16···H1^v	2.633 (19)	H1···N16^x	2.633 (19)
N18···H5A	2.9100	H2···Cl1	2.7400
N18···H64^vi	2.6500	H2···H6	2.3500
N18···H63^vii	2.6800	H2···H25^iv	2.3500
C3···Cl1	3.447 (2)	H2···C24ⁱ	3.0900
C4···C63^v	3.596 (3)	H3A···C63^v	3.0500
C4···C64^v	3.594 (3)	H3B···Cl1	2.8600
C14···C25^iv	3.569 (3)	H3B···C15	2.4900
C14···C64^v	3.486 (3)	H3B···C22	3.0100
C14···C65^v	3.567 (3)	H5A···N18	2.9100
C15···C66^v	3.537 (3)	H5A···C17	2.4500
C21···C24ⁱ	3.570 (3)	H5B···C66	2.9500
C22···C25ⁱ	3.537 (3)	H6···Cl2	2.6000
C23···Cl1ⁱⁱⁱ	3.591 (2)	H6···H2	2.3500
C24···N16ⁱⁱⁱ	3.375 (3)	H6···H25^iv	2.4800
C24···C21^viii	3.570 (3)	H23···N16ⁱⁱⁱ	2.9200
C25···Cl1^viii	3.586 (2)	H24···Cl1^ix	3.0400
C25···C14^ix	3.569 (3)	H24···N16ⁱⁱⁱ	2.6800
C25···C22^viii	3.537 (3)	H25···H2^ix	2.3500
C62···C65^vi	3.567 (3)	H25···H6^ix	2.4800
C63···C4^x	3.596 (3)	H26···N1	2.4500
C63···C65^vi	3.586 (3)	H26···H1	2.3500
C64···C4^x	3.594 (3)	H63···N18^xii	2.6800
C64···C14^x	3.486 (3)	H64···N18^xi	2.6500
C65···C14^x	3.567 (3)	H65···C62^xi	2.9700
C65···C62^xi	3.567 (3)	H66···N1	2.5800

C2—N1—C6	112.10 (14)	C63—C64—C65	120.34 (19)
C6—N1—H1	108.3 (15)	C64—C65—C66	119.8 (2)
C2—N1—H1	109.3 (13)	C61—C66—C65	121.5 (2)
N1—C2—C21	111.19 (13)	N1—C2—H2	109.00
N1—C2—C3	108.06 (15)	C3—C2—H2	109.00
C3—C2—C21	110.34 (14)	C21—C2—H2	109.00
C2—C3—C4	110.11 (15)	C2—C3—H3A	110.00
C3—C4—C5	114.09 (18)	C2—C3—H3B	110.00
C5—C4—C14	122.35 (19)	C4—C3—H3A	110.00
C3—C4—C14	123.53 (17)	C4—C3—H3B	110.00
C4—C5—C6	110.07 (15)	H3A—C3—H3B	108.00
N1—C6—C61	111.32 (15)	C4—C5—H5A	110.00
C5—C6—C61	109.74 (14)	C4—C5—H5B	110.00
N1—C6—C5	108.14 (15)	C6—C5—H5A	110.00
C15—C14—C17	114.98 (19)	C6—C5—H5B	110.00
C4—C14—C15	122.66 (19)	H5A—C5—H5B	108.00
C4—C14—C17	122.34 (17)	N1—C6—H6	109.00
N16—C15—C14	178.7 (2)	C5—C6—H6	109.00
N18—C17—C14	178.8 (2)	C61—C6—H6	109.00
C2—C21—C26	121.17 (15)	C22—C23—H23	120.00
C2—C21—C22	122.08 (16)	C24—C23—H23	120.00
C22—C21—C26	116.75 (16)	C23—C24—H24	120.00
Cl1—C22—C23	117.51 (15)	C25—C24—H24	120.00
Cl1—C22—C21	120.30 (16)	C24—C25—H25	120.00
C21—C22—C23	122.19 (19)	C26—C25—H25	120.00
C22—C23—C24	119.86 (19)	C21—C26—H26	119.00
C23—C24—C25	119.8 (2)	C25—C26—H26	119.00
C24—C25—C26	120.2 (2)	C62—C63—H63	120.00
C21—C26—C25	121.25 (18)	C64—C63—H63	120.00
C62—C61—C66	117.03 (17)	C63—C64—H64	120.00
C6—C61—C62	122.72 (18)	C65—C64—H64	120.00
C6—C61—C66	120.18 (17)	C64—C65—H65	120.00
C61—C62—C63	122.0 (2)	C66—C65—H65	120.00
Cl2—C62—C61	120.46 (15)	C61—C66—H66	119.00
Cl2—C62—C63	117.52 (17)	C65—C66—H66	119.00
C62—C63—C64	119.3 (2)

C6—N1—C2—C3	64.46 (17)	C5—C6—C61—C66	−80.5 (2)
C6—N1—C2—C21	−174.30 (14)	C2—C21—C22—Cl1	−1.4 (2)
C2—N1—C6—C5	−64.40 (18)	C2—C21—C22—C23	179.60 (16)
C2—N1—C6—C61	174.98 (14)	C26—C21—C22—Cl1	179.49 (13)
N1—C2—C3—C4	−55.69 (18)	C26—C21—C22—C23	0.5 (3)
C21—C2—C3—C4	−177.45 (15)	C2—C21—C26—C25	−179.97 (17)
N1—C2—C21—C22	161.78 (16)	C22—C21—C26—C25	−0.8 (3)
N1—C2—C21—C26	−19.1 (2)	Cl1—C22—C23—C24	−179.57 (15)
C3—C2—C21—C22	−78.3 (2)	C21—C22—C23—C24	−0.5 (3)
C3—C2—C21—C26	100.77 (19)	C22—C23—C24—C25	0.9 (3)
C2—C3—C4—C5	51.7 (2)	C23—C24—C25—C26	−1.3 (3)
C2—C3—C4—C14	−126.22 (19)	C24—C25—C26—C21	1.2 (3)
C3—C4—C5—C6	−51.6 (2)	C6—C61—C62—Cl2	2.7 (3)
C14—C4—C5—C6	126.36 (19)	C6—C61—C62—C63	−176.83 (18)
C3—C4—C14—C15	−1.1 (3)	C66—C61—C62—Cl2	179.61 (15)
C3—C4—C14—C17	−179.60 (18)	C66—C61—C62—C63	0.1 (3)
C5—C4—C14—C15	−178.89 (18)	C6—C61—C66—C65	177.46 (18)
C5—C4—C14—C17	2.6 (3)	C62—C61—C66—C65	0.5 (3)
C4—C5—C6—N1	55.4 (2)	Cl2—C62—C63—C64	−179.49 (16)
C4—C5—C6—C61	176.97 (17)	C61—C62—C63—C64	0.1 (3)
N1—C6—C61—C62	−144.01 (18)	C62—C63—C64—C65	−0.7 (3)
N1—C6—C61—C66	39.2 (2)	C63—C64—C65—C66	1.3 (3)
C5—C6—C61—C62	96.3 (2)	C64—C65—C66—C61	−1.2 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1	1.00	2.74	3.0777 (18)	100.00
C6—H6···Cl2	1.00	2.60	3.0909 (18)	110.00
C26—H26···N1	0.95	2.45	2.795 (2)	102.00

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅Cl₂N₃
M_r	368.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	15.1732 (10), 7.5493 (5), 16.3452 (12)
β (°)	105.494 (7)
V (Å³)	1804.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.51 × 0.44 × 0.21

Data collection
Diffractometer	Oxford Diffraction Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.829, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	17148, 6044, 2122
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.762

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.124, 0.89
No. of reflections	6044
No. of parameters	230
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.32

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