1-[3-(4-Chloro­phen­yl)isoquinolin-1-yl]-3,5-diphenyl-1H-pyrazole

Khan, F.N.; Manivel, P.; Krishnakumar, V.; Hathwar, V.R.; Ng, S.W.

doi:10.1107/S1600536809055718

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o369

https://doi.org/10.1107/S1600536809055718

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1-[3-(4-Chlorophenyl)isoquinolin-1-yl]-3,5-diphenyl-1H-pyrazole

F. Nawaz Khan,^a P. Manivel,^b V. Krishnakumar,^b Venkatesha R. Hathwar ^c and Seik Weng Ng ^d ^*

^aChemistry Division, School of Science and Humanities, VIT University, Vellore 632014, Tamil Nadu, India, ^bChemistry Division, School of Advanced Sciences, VIT University, Vellore 632014, Tamil Nadu, India, ^cSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560012, Karnataka, India, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 28 December 2009; accepted 30 December 2009; online 16 January 2010)

The title compound, C₃₀H₂₀ClN₃, is composed of a diaryl-substituted pyrazole ring connected to an aryl-substituted isoquinoline ring system with a dihedral angle of 65.1 (1)° between the pyrazole ring and the isoquinoline ring system. The 3-phenyl and 4-phenyl substitutents are twisted by 8.1 (1) and 43.0 (1)°, respectively, with respect to the pyrazole ring. The chlorophenyl ring and the isoquinoline ring system are twisted by 21.2 (1)° with respect to each other.

Related literature

For medicinal applications of hydrazine derivatives, see: Broadhurst et al. (2001 ).

Experimental

Crystal data

C₃₀H₂₀ClN₃
M_r = 457.94
Monoclinic, P 2₁ /c
a = 23.7864 (15) Å
b = 11.7101 (8) Å
c = 8.3602 (5) Å
β = 96.738 (1)°
V = 2312.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 290 K
0.20 × 0.16 × 0.04 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.963, T_max = 0.993
17230 measured reflections
4392 independent reflections
2890 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.126
S = 1.02
4392 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809055718/bt5160sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055718/bt5160Isup2.hkl

checkCIF report

Related literature top

For medicinal applications of hydrazine derivatives, see: Broadhurst et al. (2001).

Experimental top

1-[3-(4-Chlorophenyl)isoquinolin-1-yl]hydrazine (2.69 g, 10 mmol) and 1,3-diphenylpropane-1,3-dione (2.24 g, 10 mmol) were dissolved in ethanol (30 ml). The solution was heated for 12 h under a nitrogen atmosphere. The reaction was quenched with water; the compound was extracted with ethyl acetate. The ethyl acetate phase was washed with water, dried, concentrated and purified by column chromatography to yield a white powder. Crystals were were obtained upon recrystallization from dichloromethane.

Structure description top

For medicinal applications of hydrazine derivatives, see: Broadhurst et al. (2001).

Computing details top

Data collection: SMART (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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₃₀H₂₀ClN₃ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

1-[3-(4-Chlorophenyl)isoquinolin-1-yl]-3,5-diphenyl-1H-pyrazole top

Crystal data top

C₃₀H₂₀ClN₃	F(000) = 952
M_r = 457.94	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3042 reflections
a = 23.7864 (15) Å	θ = 2.4–21.9°
b = 11.7101 (8) Å	µ = 0.19 mm⁻¹
c = 8.3602 (5) Å	T = 290 K
β = 96.738 (1)°	Plate, colorless
V = 2312.6 (3) Å³	0.20 × 0.16 × 0.04 mm
Z = 4

Data collection top

Bruker SMART area-detector diffractometer	4392 independent reflections
Radiation source: fine-focus sealed tube	2890 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 25.7°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→26
T_min = 0.963, T_max = 0.993	k = −14→14
17230 measured reflections	l = −10→10

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0562P)² + 0.2618P] where P = (F_o² + 2F_c²)/3
4392 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₃₀H₂₀ClN₃	V = 2312.6 (3) Å³
M_r = 457.94	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 23.7864 (15) Å	µ = 0.19 mm⁻¹
b = 11.7101 (8) Å	T = 290 K
c = 8.3602 (5) Å	0.20 × 0.16 × 0.04 mm
β = 96.738 (1)°

Data collection top

Bruker SMART area-detector diffractometer	4392 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2890 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.993	R_int = 0.039
17230 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.02	Δρ_max = 0.16 e Å⁻³
4392 reflections	Δρ_min = −0.19 e Å⁻³
307 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.50745 (3)	0.63807 (9)	1.25356 (11)	0.1273 (4)
N1	0.26392 (7)	0.53740 (12)	0.79095 (19)	0.0492 (4)
N2	0.19665 (7)	0.41903 (13)	0.65629 (19)	0.0491 (4)
N3	0.14743 (7)	0.38380 (13)	0.70881 (19)	0.0528 (4)
C1	0.21697 (9)	0.53202 (15)	0.6937 (2)	0.0464 (5)
C2	0.18694 (9)	0.62628 (16)	0.6200 (2)	0.0474 (5)
C3	0.13772 (9)	0.61722 (18)	0.5098 (2)	0.0575 (6)
H3	0.1220	0.5459	0.4843	0.069*
C4	0.11301 (10)	0.7131 (2)	0.4401 (3)	0.0649 (6)
H4	0.0806	0.7067	0.3668	0.078*
C5	0.13619 (11)	0.82097 (19)	0.4784 (3)	0.0657 (6)
H5	0.1188	0.8856	0.4305	0.079*
C6	0.18349 (10)	0.83272 (17)	0.5840 (3)	0.0604 (6)
H6	0.1982	0.9051	0.6081	0.072*
C7	0.21069 (9)	0.73527 (16)	0.6579 (2)	0.0495 (5)
C8	0.26116 (9)	0.74042 (16)	0.7625 (2)	0.0545 (5)
H8	0.2775	0.8111	0.7891	0.065*
C9	0.28696 (9)	0.64306 (16)	0.8263 (2)	0.0486 (5)
C10	0.34144 (9)	0.64280 (17)	0.9322 (2)	0.0530 (5)
C11	0.36151 (10)	0.73945 (19)	1.0167 (3)	0.0661 (6)
H11	0.3401	0.8061	1.0078	0.079*
C12	0.41255 (12)	0.7383 (2)	1.1135 (3)	0.0797 (7)
H12	0.4255	0.8038	1.1691	0.096*
C13	0.44384 (10)	0.6405 (3)	1.1273 (3)	0.0770 (7)
C14	0.42564 (10)	0.5433 (2)	1.0454 (3)	0.0756 (7)
H14	0.4474	0.4772	1.0549	0.091*
C15	0.37442 (10)	0.54535 (19)	0.9486 (3)	0.0638 (6)
H15	0.3618	0.4796	0.8932	0.077*
C16	0.22447 (8)	0.33297 (15)	0.5886 (2)	0.0457 (5)
C17	0.19129 (9)	0.23868 (16)	0.5973 (2)	0.0503 (5)
H17	0.1985	0.1658	0.5606	0.060*
C18	0.14428 (8)	0.27279 (15)	0.6720 (2)	0.0469 (5)
C19	0.09634 (8)	0.20395 (16)	0.7112 (2)	0.0487 (5)
C20	0.05671 (10)	0.24761 (19)	0.8028 (3)	0.0621 (6)
H20	0.0602	0.3226	0.8393	0.075*
C21	0.01216 (10)	0.1822 (2)	0.8410 (3)	0.0750 (7)
H21	−0.0137	0.2129	0.9044	0.090*
C22	0.00553 (11)	0.0715 (2)	0.7861 (3)	0.0740 (7)
H22	−0.0248	0.0275	0.8113	0.089*
C23	0.04403 (11)	0.02741 (19)	0.6942 (3)	0.0742 (7)
H23	0.0398	−0.0470	0.6558	0.089*
C24	0.08906 (10)	0.09214 (17)	0.6579 (3)	0.0645 (6)
H24	0.1152	0.0603	0.5963	0.077*
C25	0.27834 (9)	0.34958 (15)	0.5214 (2)	0.0479 (5)
C26	0.28817 (10)	0.44330 (17)	0.4282 (3)	0.0641 (6)
H26	0.2597	0.4971	0.4039	0.077*
C27	0.33964 (12)	0.45783 (19)	0.3709 (3)	0.0758 (7)
H27	0.3457	0.5217	0.3090	0.091*
C28	0.38175 (11)	0.3795 (2)	0.4041 (3)	0.0734 (7)
H28	0.4167	0.3902	0.3669	0.088*
C29	0.37204 (11)	0.2852 (2)	0.4925 (3)	0.0769 (7)
H29	0.4004	0.2306	0.5139	0.092*
C30	0.32081 (9)	0.26987 (18)	0.5502 (3)	0.0646 (6)
H30	0.3148	0.2048	0.6096	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0696 (5)	0.1876 (10)	0.1191 (7)	−0.0076 (5)	−0.0121 (4)	−0.0404 (6)
N1	0.0585 (11)	0.0386 (9)	0.0517 (10)	−0.0025 (8)	0.0112 (9)	−0.0036 (7)
N2	0.0550 (11)	0.0364 (9)	0.0564 (10)	−0.0014 (8)	0.0090 (8)	−0.0034 (7)
N3	0.0581 (11)	0.0424 (10)	0.0585 (10)	−0.0037 (8)	0.0096 (9)	−0.0011 (8)
C1	0.0581 (13)	0.0349 (11)	0.0483 (11)	−0.0019 (9)	0.0153 (10)	−0.0056 (8)
C2	0.0565 (13)	0.0421 (11)	0.0463 (11)	0.0043 (10)	0.0169 (10)	−0.0021 (9)
C3	0.0660 (15)	0.0528 (13)	0.0557 (12)	0.0036 (11)	0.0153 (11)	−0.0019 (10)
C4	0.0685 (16)	0.0687 (16)	0.0585 (13)	0.0150 (13)	0.0119 (11)	0.0035 (11)
C5	0.0850 (18)	0.0551 (14)	0.0603 (14)	0.0241 (13)	0.0230 (13)	0.0083 (11)
C6	0.0831 (17)	0.0393 (12)	0.0626 (13)	0.0115 (11)	0.0248 (13)	0.0002 (10)
C7	0.0627 (14)	0.0396 (11)	0.0497 (11)	0.0039 (10)	0.0221 (10)	−0.0024 (9)
C8	0.0692 (15)	0.0357 (11)	0.0620 (13)	−0.0058 (10)	0.0225 (12)	−0.0077 (9)
C9	0.0576 (13)	0.0406 (12)	0.0509 (11)	−0.0055 (10)	0.0191 (10)	−0.0069 (9)
C10	0.0591 (14)	0.0510 (13)	0.0514 (12)	−0.0087 (10)	0.0171 (10)	−0.0048 (10)
C11	0.0729 (17)	0.0604 (14)	0.0668 (15)	−0.0103 (12)	0.0166 (13)	−0.0143 (11)
C12	0.0724 (18)	0.093 (2)	0.0762 (17)	−0.0232 (16)	0.0188 (14)	−0.0332 (14)
C13	0.0535 (15)	0.110 (2)	0.0684 (16)	−0.0136 (15)	0.0116 (12)	−0.0142 (15)
C14	0.0608 (17)	0.0819 (18)	0.0838 (17)	−0.0015 (13)	0.0074 (14)	−0.0025 (14)
C15	0.0633 (15)	0.0564 (14)	0.0724 (15)	−0.0081 (12)	0.0105 (12)	−0.0051 (11)
C16	0.0517 (12)	0.0366 (11)	0.0475 (11)	0.0026 (9)	0.0009 (9)	−0.0013 (8)
C17	0.0600 (14)	0.0337 (11)	0.0557 (12)	0.0010 (10)	0.0011 (10)	−0.0030 (9)
C18	0.0543 (13)	0.0386 (11)	0.0461 (11)	−0.0010 (9)	−0.0012 (9)	0.0008 (8)
C19	0.0505 (12)	0.0454 (12)	0.0479 (11)	−0.0014 (10)	−0.0037 (9)	0.0056 (9)
C20	0.0647 (15)	0.0594 (14)	0.0625 (14)	−0.0055 (12)	0.0082 (12)	−0.0038 (11)
C21	0.0671 (17)	0.0862 (19)	0.0739 (16)	−0.0064 (14)	0.0178 (13)	−0.0008 (14)
C22	0.0609 (16)	0.0766 (18)	0.0824 (17)	−0.0146 (14)	0.0000 (14)	0.0200 (14)
C23	0.0715 (17)	0.0490 (14)	0.1004 (19)	−0.0119 (13)	0.0028 (15)	0.0067 (13)
C24	0.0656 (15)	0.0432 (13)	0.0849 (16)	−0.0042 (11)	0.0090 (12)	−0.0001 (11)
C25	0.0546 (13)	0.0377 (11)	0.0503 (11)	0.0008 (9)	0.0019 (9)	−0.0062 (8)
C26	0.0801 (17)	0.0449 (12)	0.0722 (15)	0.0134 (11)	0.0285 (13)	0.0067 (10)
C27	0.100 (2)	0.0476 (14)	0.0877 (17)	0.0030 (14)	0.0450 (16)	0.0004 (12)
C28	0.0662 (16)	0.0680 (16)	0.0895 (18)	−0.0083 (14)	0.0239 (13)	−0.0155 (14)
C29	0.0578 (16)	0.0710 (17)	0.1009 (19)	0.0112 (13)	0.0049 (14)	0.0056 (15)
C30	0.0579 (15)	0.0520 (13)	0.0829 (16)	0.0016 (11)	0.0034 (12)	0.0113 (11)

Geometric parameters (Å, º) top

Cl1—C13	1.740 (3)	C14—H14	0.9300
N1—C1	1.304 (2)	C15—H15	0.9300
N1—C9	1.371 (2)	C16—C17	1.364 (2)
N2—N3	1.362 (2)	C16—C25	1.471 (3)
N2—C16	1.364 (2)	C17—C18	1.401 (3)
N2—C1	1.431 (2)	C17—H17	0.9300
N3—C18	1.336 (2)	C18—C19	1.465 (3)
C1—C2	1.416 (3)	C19—C20	1.380 (3)
C2—C3	1.406 (3)	C19—C24	1.387 (3)
C2—C7	1.416 (3)	C20—C21	1.375 (3)
C3—C4	1.366 (3)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.378 (3)
C4—C5	1.400 (3)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.364 (3)
C5—C6	1.353 (3)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.375 (3)
C6—C7	1.417 (3)	C23—H23	0.9300
C6—H6	0.9300	C24—H24	0.9300
C7—C8	1.401 (3)	C25—C30	1.376 (3)
C8—C9	1.373 (3)	C25—C26	1.382 (3)
C8—H8	0.9300	C26—C27	1.377 (3)
C9—C10	1.481 (3)	C26—H26	0.9300
C10—C15	1.382 (3)	C27—C28	1.363 (3)
C10—C11	1.389 (3)	C27—H27	0.9300
C11—C12	1.378 (3)	C28—C29	1.363 (3)
C11—H11	0.9300	C28—H28	0.9300
C12—C13	1.364 (3)	C29—C30	1.374 (3)
C12—H12	0.9300	C29—H29	0.9300
C13—C14	1.372 (3)	C30—H30	0.9300
C14—C15	1.381 (3)

C1—N1—C9	118.01 (16)	C14—C15—H15	119.2
N3—N2—C16	112.77 (15)	C10—C15—H15	119.2
N3—N2—C1	119.41 (15)	C17—C16—N2	105.32 (17)
C16—N2—C1	127.30 (17)	C17—C16—C25	131.50 (18)
C18—N3—N2	104.34 (15)	N2—C16—C25	123.17 (16)
N1—C1—C2	125.82 (17)	C16—C17—C18	106.85 (17)
N1—C1—N2	115.07 (16)	C16—C17—H17	126.6
C2—C1—N2	119.07 (18)	C18—C17—H17	126.6
C3—C2—C1	124.39 (18)	N3—C18—C17	110.72 (17)
C3—C2—C7	119.60 (18)	N3—C18—C19	120.53 (18)
C1—C2—C7	115.95 (19)	C17—C18—C19	128.74 (18)
C4—C3—C2	120.1 (2)	C20—C19—C24	117.39 (19)
C4—C3—H3	120.0	C20—C19—C18	121.37 (19)
C2—C3—H3	120.0	C24—C19—C18	121.24 (19)
C3—C4—C5	120.4 (2)	C21—C20—C19	121.2 (2)
C3—C4—H4	119.8	C21—C20—H20	119.4
C5—C4—H4	119.8	C19—C20—H20	119.4
C6—C5—C4	121.0 (2)	C20—C21—C22	120.5 (2)
C6—C5—H5	119.5	C20—C21—H21	119.7
C4—C5—H5	119.5	C22—C21—H21	119.7
C5—C6—C7	120.3 (2)	C23—C22—C21	119.1 (2)
C5—C6—H6	119.8	C23—C22—H22	120.5
C7—C6—H6	119.8	C21—C22—H22	120.5
C8—C7—C2	117.93 (17)	C22—C23—C24	120.5 (2)
C8—C7—C6	123.46 (19)	C22—C23—H23	119.8
C2—C7—C6	118.6 (2)	C24—C23—H23	119.8
C9—C8—C7	121.21 (18)	C23—C24—C19	121.4 (2)
C9—C8—H8	119.4	C23—C24—H24	119.3
C7—C8—H8	119.4	C19—C24—H24	119.3
C8—C9—N1	121.08 (19)	C30—C25—C26	117.9 (2)
C8—C9—C10	123.64 (18)	C30—C25—C16	119.88 (18)
N1—C9—C10	115.25 (17)	C26—C25—C16	122.21 (18)
C15—C10—C11	117.7 (2)	C27—C26—C25	120.7 (2)
C15—C10—C9	120.50 (19)	C27—C26—H26	119.6
C11—C10—C9	121.8 (2)	C25—C26—H26	119.6
C12—C11—C10	121.2 (2)	C28—C27—C26	120.6 (2)
C12—C11—H11	119.4	C28—C27—H27	119.7
C10—C11—H11	119.4	C26—C27—H27	119.7
C13—C12—C11	119.5 (2)	C29—C28—C27	119.2 (2)
C13—C12—H12	120.3	C29—C28—H28	120.4
C11—C12—H12	120.3	C27—C28—H28	120.4
C12—C13—C14	121.2 (2)	C28—C29—C30	120.6 (2)
C12—C13—Cl1	119.5 (2)	C28—C29—H29	119.7
C14—C13—Cl1	119.4 (2)	C30—C29—H29	119.7
C13—C14—C15	118.9 (2)	C29—C30—C25	120.9 (2)
C13—C14—H14	120.5	C29—C30—H30	119.6
C15—C14—H14	120.5	C25—C30—H30	119.6
C14—C15—C10	121.6 (2)

C16—N2—N3—C18	−0.4 (2)	Cl1—C13—C14—C15	178.42 (18)
C1—N2—N3—C18	−172.66 (16)	C13—C14—C15—C10	0.3 (3)
C9—N1—C1—C2	−0.1 (3)	C11—C10—C15—C14	0.0 (3)
C9—N1—C1—N2	177.32 (15)	C9—C10—C15—C14	179.37 (19)
N3—N2—C1—N1	113.25 (19)	N3—N2—C16—C17	0.5 (2)
C16—N2—C1—N1	−57.8 (2)	C1—N2—C16—C17	172.00 (18)
N3—N2—C1—C2	−69.1 (2)	N3—N2—C16—C25	179.40 (17)
C16—N2—C1—C2	119.8 (2)	C1—N2—C16—C25	−9.0 (3)
N1—C1—C2—C3	176.97 (18)	N2—C16—C17—C18	−0.3 (2)
N2—C1—C2—C3	−0.4 (3)	C25—C16—C17—C18	−179.16 (19)
N1—C1—C2—C7	−0.3 (3)	N2—N3—C18—C17	0.1 (2)
N2—C1—C2—C7	−177.68 (16)	N2—N3—C18—C19	179.74 (16)
C1—C2—C3—C4	−177.35 (18)	C16—C17—C18—N3	0.1 (2)
C7—C2—C3—C4	−0.1 (3)	C16—C17—C18—C19	−179.44 (18)
C2—C3—C4—C5	−0.4 (3)	N3—C18—C19—C20	−7.5 (3)
C3—C4—C5—C6	0.4 (3)	C17—C18—C19—C20	172.01 (19)
C4—C5—C6—C7	0.2 (3)	N3—C18—C19—C24	172.62 (18)
C3—C2—C7—C8	−177.10 (17)	C17—C18—C19—C24	−7.9 (3)
C1—C2—C7—C8	0.4 (3)	C24—C19—C20—C21	0.7 (3)
C3—C2—C7—C6	0.6 (3)	C18—C19—C20—C21	−179.2 (2)
C1—C2—C7—C6	178.07 (17)	C19—C20—C21—C22	−1.1 (3)
C5—C6—C7—C8	176.95 (19)	C20—C21—C22—C23	0.5 (4)
C5—C6—C7—C2	−0.6 (3)	C21—C22—C23—C24	0.5 (4)
C2—C7—C8—C9	0.1 (3)	C22—C23—C24—C19	−0.9 (4)
C6—C7—C8—C9	−177.53 (18)	C20—C19—C24—C23	0.3 (3)
C7—C8—C9—N1	−0.5 (3)	C18—C19—C24—C23	−179.8 (2)
C7—C8—C9—C10	177.49 (17)	C17—C16—C25—C30	−43.5 (3)
C1—N1—C9—C8	0.6 (3)	N2—C16—C25—C30	137.8 (2)
C1—N1—C9—C10	−177.64 (16)	C17—C16—C25—C26	136.1 (2)
C8—C9—C10—C15	−158.10 (19)	N2—C16—C25—C26	−42.5 (3)
N1—C9—C10—C15	20.0 (3)	C30—C25—C26—C27	−2.2 (3)
C8—C9—C10—C11	21.3 (3)	C16—C25—C26—C27	178.2 (2)
N1—C9—C10—C11	−160.58 (18)	C25—C26—C27—C28	0.5 (4)
C15—C10—C11—C12	0.0 (3)	C26—C27—C28—C29	1.2 (4)
C9—C10—C11—C12	−179.4 (2)	C27—C28—C29—C30	−1.2 (4)
C10—C11—C12—C13	−0.3 (4)	C28—C29—C30—C25	−0.5 (4)
C11—C12—C13—C14	0.6 (4)	C26—C25—C30—C29	2.2 (3)
C11—C12—C13—Cl1	−178.40 (18)	C16—C25—C30—C29	−178.2 (2)
C12—C13—C14—C15	−0.5 (4)

Experimental details

Crystal data
Chemical formula	C₃₀H₂₀ClN₃
M_r	457.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	290
a, b, c (Å)	23.7864 (15), 11.7101 (8), 8.3602 (5)
β (°)	96.738 (1)
V (Å³)	2312.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.20 × 0.16 × 0.04

Data collection
Diffractometer	Bruker SMART area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.963, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	17230, 4392, 2890
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.126, 1.02
No. of reflections	4392
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.19

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the Department of Science and Technology, India, for use of the diffraction facility at IISc under the IRHPA–DST program. FNK thanks the DST for Fast Track Proposal funding. We thank VIT University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Broadhurst, M. J., Johnson, W. H. & Walter, D. S. (2001). US Patent No. 6235787. Google Scholar
Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar