3-(4-Chloro-phen-yl)-1-[(E)-1-(4-chloro-phen-yl)-2-(4-methyl-phenyl-sulfan-yl)ethen-yl]-4-(4-methyl-phenyl-sulfan-yl)-1H-pyrazole.

In the title compound, C(31)H(24)Cl(2)N(2)S(2), the pyrazole ring adopts planar conformation with a maximum deviation of 0.002 (2) Å. The chloro-phenyl rings are twisted out of the plane of the pyrazole ring by 75.1 (1) and 39.5 (1)°. The crystal packing is controlled by weak intermolecular C-H⋯π interactions.

Related literature

For the pharmacological and medicinal properties of pyrazole derivatives, see: Baraldi et al. (1998 ▶); Bruno et al. (1990 ▶); Cottineau et al. (2002 ▶); Londershausen (1996 ▶); Chen & Li (1998 ▶); Mishra et al. (1998 ▶); Smith et al. (2001 ▶). For sp 2 hybridization, see: Beddoes et al., 1986 ▶). For bond-length data, see: Jin et al. (2004 ▶).

Experimental

Crystal data

C31H24Cl2N2S2

M = 559.54

Monoclinic,

a = 9.7515 (2) Å

b = 10.2097 (3) Å

c = 27.6705 (6) Å

β = 96.402 (1)°

V = 2737.69 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.883, T max = 0.921

38656 measured reflections

9852 independent reflections

5773 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.160

S = 1.03

9852 reflections

336 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.33 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043293/bt5084sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043293/bt5084Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C31H24Cl2N2S2	F(000) = 1160
Mr = 559.54	Dx = 1.358 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2546 reflections
a = 9.7515 (2) Å	θ = 1.5–32.5°
b = 10.2097 (3) Å	µ = 0.41 mm−1
c = 27.6705 (6) Å	T = 293 K
β = 96.402 (1)°	Block, colourless
V = 2737.69 (11) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII diffractometer	9852 independent reflections
Radiation source: fine-focus sealed tube	5773 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω and φ scans	θmax = 32.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −14→14
Tmin = 0.883, Tmax = 0.921	k = −15→15
38656 measured reflections	l = −41→39

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0723P)2 + 0.5516P] where P = (Fo2 + 2Fc2)/3
9852 reflections	(Δ/σ)max = 0.003
336 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.08583 (6)	−0.11974 (5)	0.63584 (2)	0.05549 (15)
S2	0.25311 (5)	0.35982 (5)	0.42760 (2)	0.05549 (15)
Cl1	−0.13889 (7)	0.45353 (6)	0.68961 (2)	0.07471 (19)
Cl2	0.48797 (8)	−0.21313 (9)	0.30187 (2)	0.0905 (2)
N1	0.23543 (16)	0.02119 (14)	0.49711 (5)	0.0415 (3)
N2	0.18350 (16)	0.10815 (14)	0.52737 (5)	0.0421 (3)
C3	0.1835 (2)	0.23137 (18)	0.50948 (7)	0.0472 (4)
H3	0.1531	0.3062	0.5242	0.057*
C4	0.23608 (19)	0.22595 (18)	0.46595 (7)	0.0446 (4)
C5	0.26756 (18)	0.09181 (17)	0.45965 (6)	0.0398 (4)
C6	0.13934 (19)	0.06576 (17)	0.57196 (6)	0.0410 (4)
C7	0.1621 (2)	−0.05738 (19)	0.58678 (7)	0.0485 (4)
H7	0.2196	−0.1107	0.5707	0.058*
C8	0.2206 (2)	−0.21076 (18)	0.66790 (6)	0.0461 (4)
C9	0.3584 (2)	−0.1814 (2)	0.66695 (8)	0.0583 (5)
H9	0.3845	−0.1116	0.6484	0.070*
C10	0.4568 (3)	−0.2562 (2)	0.69371 (8)	0.0653 (6)
H10	0.5496	−0.2370	0.6924	0.078*
C11	0.4224 (3)	−0.3585 (2)	0.72236 (7)	0.0606 (5)
C12	0.2849 (3)	−0.3848 (2)	0.72369 (8)	0.0614 (6)
H12	0.2592	−0.4524	0.7433	0.074*
C13	0.1842 (2)	−0.3134 (2)	0.69661 (7)	0.0566 (5)
H13	0.0917	−0.3340	0.6976	0.068*
C14	0.07032 (18)	0.16654 (17)	0.59941 (6)	0.0389 (3)
C15	0.1380 (2)	0.2157 (2)	0.64224 (7)	0.0495 (4)
H15	0.2271	0.1877	0.6527	0.059*
C16	0.0749 (2)	0.3054 (2)	0.66948 (7)	0.0523 (5)
H16	0.1212	0.3388	0.6980	0.063*
C17	−0.0571 (2)	0.34490 (18)	0.65410 (6)	0.0459 (4)
C18	−0.1264 (2)	0.29888 (19)	0.61145 (7)	0.0478 (4)
H18	−0.2155	0.3273	0.6012	0.057*
C19	−0.06171 (19)	0.20999 (18)	0.58410 (6)	0.0443 (4)
H19	−0.1074	0.1789	0.5551	0.053*
C20	0.4342 (2)	0.38614 (17)	0.43419 (7)	0.0441 (4)
C21	0.4884 (2)	0.4601 (2)	0.39927 (7)	0.0521 (5)
H21	0.4301	0.4967	0.3740	0.063*
C22	0.6289 (2)	0.4800 (2)	0.40176 (8)	0.0549 (5)
H22	0.6639	0.5305	0.3780	0.066*
C23	0.7187 (2)	0.42680 (19)	0.43848 (8)	0.0524 (5)
C24	0.6620 (3)	0.3574 (2)	0.47388 (9)	0.0679 (6)
H24	0.7199	0.3227	0.4997	0.081*
C25	0.5222 (2)	0.3377 (2)	0.47219 (8)	0.0649 (6)
H25	0.4869	0.2914	0.4970	0.078*
C26	0.32826 (18)	0.02448 (17)	0.42028 (6)	0.0400 (4)
C27	0.2903 (2)	0.0553 (2)	0.37175 (6)	0.0510 (5)
H27	0.2310	0.1252	0.3636	0.061*
C28	0.3405 (2)	−0.0176 (2)	0.33562 (7)	0.0576 (5)
H28	0.3147	0.0028	0.3031	0.069*
C29	0.4282 (2)	−0.1200 (2)	0.34765 (7)	0.0553 (5)
C30	0.4714 (2)	−0.1501 (2)	0.39539 (8)	0.0567 (5)
H30	0.5336	−0.2178	0.4032	0.068*
C31	0.4201 (2)	−0.07719 (19)	0.43141 (7)	0.0490 (4)
H31	0.4480	−0.0969	0.4638	0.059*
C32	0.5335 (3)	−0.4378 (3)	0.75125 (10)	0.0887 (9)
H32A	0.5850	−0.4854	0.7294	0.133*
H32B	0.4918	−0.4983	0.7718	0.133*
H32C	0.5942	−0.3802	0.7709	0.133*
C33	0.8720 (2)	0.4392 (3)	0.43899 (11)	0.0728 (7)
H33A	0.9079	0.3617	0.4253	0.109*
H33B	0.9136	0.4497	0.4719	0.109*
H33C	0.8929	0.5140	0.4201	0.109*

	U11	U22	U33	U12	U13	U23
S1	0.0571 (3)	0.0534 (3)	0.0597 (3)	0.0077 (2)	0.0230 (2)	0.0147 (2)
S2	0.0492 (3)	0.0490 (3)	0.0690 (3)	0.0058 (2)	0.0096 (2)	0.0254 (2)
Cl1	0.0911 (5)	0.0722 (4)	0.0659 (3)	0.0193 (3)	0.0308 (3)	−0.0139 (3)
Cl2	0.0853 (5)	0.1220 (6)	0.0684 (4)	−0.0011 (4)	0.0276 (3)	−0.0391 (4)
N1	0.0492 (8)	0.0357 (7)	0.0409 (7)	0.0026 (6)	0.0111 (6)	0.0010 (6)
N2	0.0519 (9)	0.0344 (7)	0.0416 (7)	0.0020 (6)	0.0125 (6)	0.0017 (6)
C3	0.0532 (11)	0.0349 (9)	0.0553 (10)	0.0047 (8)	0.0140 (8)	0.0039 (7)
C4	0.0460 (10)	0.0392 (9)	0.0498 (9)	0.0025 (8)	0.0112 (8)	0.0094 (7)
C5	0.0398 (9)	0.0391 (9)	0.0411 (8)	0.0002 (7)	0.0066 (7)	0.0051 (7)
C6	0.0451 (9)	0.0391 (9)	0.0402 (8)	0.0021 (7)	0.0107 (7)	0.0008 (7)
C7	0.0563 (11)	0.0428 (10)	0.0494 (9)	0.0078 (8)	0.0193 (8)	0.0051 (8)
C8	0.0559 (11)	0.0412 (9)	0.0433 (9)	−0.0014 (8)	0.0143 (8)	0.0009 (7)
C9	0.0607 (13)	0.0519 (12)	0.0640 (12)	−0.0077 (10)	0.0141 (10)	0.0108 (9)
C10	0.0556 (13)	0.0749 (15)	0.0660 (13)	−0.0008 (11)	0.0096 (10)	0.0038 (11)
C11	0.0736 (15)	0.0634 (14)	0.0451 (10)	0.0151 (11)	0.0085 (9)	−0.0005 (9)
C12	0.0828 (16)	0.0545 (12)	0.0484 (10)	0.0020 (11)	0.0147 (10)	0.0124 (9)
C13	0.0614 (13)	0.0586 (12)	0.0522 (11)	−0.0069 (10)	0.0174 (9)	0.0101 (9)
C14	0.0424 (9)	0.0360 (8)	0.0393 (8)	−0.0002 (7)	0.0090 (7)	0.0014 (6)
C15	0.0450 (10)	0.0531 (11)	0.0491 (10)	0.0040 (8)	−0.0004 (8)	−0.0048 (8)
C16	0.0611 (12)	0.0535 (11)	0.0415 (9)	−0.0004 (9)	0.0014 (8)	−0.0081 (8)
C17	0.0562 (11)	0.0402 (9)	0.0447 (9)	0.0030 (8)	0.0198 (8)	−0.0002 (7)
C18	0.0411 (10)	0.0457 (10)	0.0574 (10)	0.0025 (8)	0.0090 (8)	−0.0002 (8)
C19	0.0433 (10)	0.0427 (9)	0.0465 (9)	−0.0016 (8)	0.0029 (7)	−0.0048 (7)
C20	0.0502 (10)	0.0361 (9)	0.0469 (9)	0.0048 (7)	0.0091 (8)	0.0047 (7)
C21	0.0570 (12)	0.0542 (11)	0.0459 (9)	0.0034 (9)	0.0086 (8)	0.0114 (8)
C22	0.0569 (12)	0.0552 (12)	0.0549 (11)	−0.0034 (10)	0.0162 (9)	0.0050 (9)
C23	0.0513 (11)	0.0397 (10)	0.0659 (12)	−0.0011 (8)	0.0060 (9)	−0.0104 (8)
C24	0.0593 (13)	0.0685 (15)	0.0720 (14)	0.0010 (11)	−0.0097 (11)	0.0181 (12)
C25	0.0635 (14)	0.0664 (14)	0.0637 (13)	−0.0024 (11)	0.0024 (10)	0.0300 (11)
C26	0.0375 (9)	0.0437 (9)	0.0396 (8)	−0.0027 (7)	0.0075 (6)	0.0031 (7)
C27	0.0421 (10)	0.0679 (13)	0.0428 (9)	0.0010 (9)	0.0043 (7)	0.0072 (8)
C28	0.0469 (11)	0.0878 (16)	0.0382 (9)	−0.0089 (11)	0.0059 (8)	0.0003 (9)
C29	0.0462 (11)	0.0725 (14)	0.0498 (10)	−0.0123 (10)	0.0173 (8)	−0.0154 (9)
C30	0.0568 (12)	0.0572 (12)	0.0578 (11)	0.0074 (10)	0.0141 (9)	−0.0059 (9)
C31	0.0563 (11)	0.0492 (10)	0.0416 (9)	0.0053 (9)	0.0060 (8)	0.0022 (7)
C32	0.100 (2)	0.100 (2)	0.0659 (15)	0.0409 (18)	0.0087 (14)	0.0101 (14)
C33	0.0553 (13)	0.0606 (14)	0.1015 (19)	−0.0034 (11)	0.0041 (12)	−0.0168 (13)

S1—C7	1.7398 (19)	C16—H16	0.9300
S1—C8	1.766 (2)	C17—C18	1.376 (3)
S2—C4	1.7496 (18)	C18—C19	1.378 (3)
S2—C20	1.776 (2)	C18—H18	0.9300
Cl1—C17	1.7340 (18)	C19—H19	0.9300
Cl2—C29	1.736 (2)	C20—C25	1.373 (3)
N1—C5	1.328 (2)	C20—C21	1.377 (3)
N1—N2	1.3565 (19)	C21—C22	1.379 (3)
N2—C3	1.352 (2)	C21—H21	0.9300
N2—C6	1.419 (2)	C22—C23	1.376 (3)
C3—C4	1.362 (3)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.374 (3)
C4—C5	1.418 (3)	C23—C33	1.500 (3)
C5—C26	1.467 (2)	C24—C25	1.373 (3)
C6—C7	1.333 (3)	C24—H24	0.9300
C6—C14	1.484 (2)	C25—H25	0.9300
C7—H7	0.9300	C26—C31	1.383 (3)
C8—C9	1.380 (3)	C26—C27	1.389 (2)
C8—C13	1.385 (3)	C27—C28	1.379 (3)
C9—C10	1.377 (3)	C27—H27	0.9300
C9—H9	0.9300	C28—C29	1.369 (3)
C10—C11	1.376 (3)	C28—H28	0.9300
C10—H10	0.9300	C29—C30	1.375 (3)
C11—C12	1.372 (4)	C30—C31	1.381 (3)
C11—C32	1.508 (3)	C30—H30	0.9300
C12—C13	1.376 (3)	C31—H31	0.9300
C12—H12	0.9300	C32—H32A	0.9600
C13—H13	0.9300	C32—H32B	0.9600
C14—C19	1.383 (3)	C32—H32C	0.9600
C14—C15	1.385 (2)	C33—H33A	0.9600
C15—C16	1.374 (3)	C33—H33B	0.9600
C15—H15	0.9300	C33—H33C	0.9600
C16—C17	1.371 (3)
C7—S1—C8	103.04 (9)	C19—C18—H18	120.5
C4—S2—C20	102.51 (9)	C18—C19—C14	120.68 (17)
C5—N1—N2	105.26 (13)	C18—C19—H19	119.7
C3—N2—N1	111.58 (14)	C14—C19—H19	119.7
C3—N2—C6	127.92 (15)	C25—C20—C21	118.63 (19)
N1—N2—C6	120.49 (14)	C25—C20—S2	123.61 (16)
N2—C3—C4	107.54 (16)	C21—C20—S2	117.76 (14)
N2—C3—H3	126.2	C20—C21—C22	120.14 (18)
C4—C3—H3	126.2	C20—C21—H21	119.9
C3—C4—C5	104.82 (15)	C22—C21—H21	119.9
C3—C4—S2	125.11 (15)	C23—C22—C21	121.67 (19)
C5—C4—S2	130.04 (14)	C23—C22—H22	119.2
N1—C5—C4	110.80 (15)	C21—C22—H22	119.2
N1—C5—C26	118.34 (15)	C24—C23—C22	117.2 (2)
C4—C5—C26	130.85 (15)	C24—C23—C33	121.1 (2)
C7—C6—N2	119.92 (16)	C22—C23—C33	121.7 (2)
C7—C6—C14	124.46 (16)	C25—C24—C23	121.9 (2)
N2—C6—C14	115.62 (14)	C25—C24—H24	119.1
C6—C7—S1	120.93 (15)	C23—C24—H24	119.1
C6—C7—H7	119.5	C20—C25—C24	120.4 (2)
S1—C7—H7	119.5	C20—C25—H25	119.8
C9—C8—C13	119.17 (19)	C24—C25—H25	119.8
C9—C8—S1	123.22 (15)	C31—C26—C27	118.79 (17)
C13—C8—S1	117.56 (16)	C31—C26—C5	119.41 (15)
C10—C9—C8	119.4 (2)	C27—C26—C5	121.71 (17)
C10—C9—H9	120.3	C28—C27—C26	120.04 (19)
C8—C9—H9	120.3	C28—C27—H27	120.0
C11—C10—C9	122.1 (2)	C26—C27—H27	120.0
C11—C10—H10	119.0	C29—C28—C27	119.92 (18)
C9—C10—H10	119.0	C29—C28—H28	120.0
C12—C11—C10	117.8 (2)	C27—C28—H28	120.0
C12—C11—C32	121.8 (2)	C28—C29—C30	121.33 (19)
C10—C11—C32	120.4 (2)	C28—C29—Cl2	119.50 (16)
C11—C12—C13	121.5 (2)	C30—C29—Cl2	119.16 (18)
C11—C12—H12	119.3	C29—C30—C31	118.5 (2)
C13—C12—H12	119.3	C29—C30—H30	120.8
C12—C13—C8	120.0 (2)	C31—C30—H30	120.8
C12—C13—H13	120.0	C30—C31—C26	121.40 (18)
C8—C13—H13	120.0	C30—C31—H31	119.3
C19—C14—C15	118.97 (16)	C26—C31—H31	119.3
C19—C14—C6	121.71 (15)	C11—C32—H32A	109.5
C15—C14—C6	119.30 (16)	C11—C32—H32B	109.5
C16—C15—C14	120.76 (18)	H32A—C32—H32B	109.5
C16—C15—H15	119.6	C11—C32—H32C	109.5
C14—C15—H15	119.6	H32A—C32—H32C	109.5
C17—C16—C15	119.21 (17)	H32B—C32—H32C	109.5
C17—C16—H16	120.4	C23—C33—H33A	109.5
C15—C16—H16	120.4	C23—C33—H33B	109.5
C16—C17—C18	121.34 (17)	H33A—C33—H33B	109.5
C16—C17—Cl1	119.20 (15)	C23—C33—H33C	109.5
C18—C17—Cl1	119.46 (16)	H33A—C33—H33C	109.5
C17—C18—C19	119.02 (18)	H33B—C33—H33C	109.5
C17—C18—H18	120.5
C5—N1—N2—C3	−0.3 (2)	C19—C14—C15—C16	0.6 (3)
C5—N1—N2—C6	−179.36 (16)	C6—C14—C15—C16	−177.49 (18)
N1—N2—C3—C4	0.4 (2)	C14—C15—C16—C17	0.8 (3)
C6—N2—C3—C4	179.37 (18)	C15—C16—C17—C18	−1.5 (3)
N2—C3—C4—C5	−0.3 (2)	C15—C16—C17—Cl1	177.69 (16)
N2—C3—C4—S2	178.16 (14)	C16—C17—C18—C19	0.8 (3)
C20—S2—C4—C3	108.01 (18)	Cl1—C17—C18—C19	−178.36 (15)
C20—S2—C4—C5	−73.92 (19)	C17—C18—C19—C14	0.6 (3)
N2—N1—C5—C4	0.10 (19)	C15—C14—C19—C18	−1.3 (3)
N2—N1—C5—C26	179.47 (15)	C6—C14—C19—C18	176.76 (17)
C3—C4—C5—N1	0.1 (2)	C4—S2—C20—C25	−18.3 (2)
S2—C4—C5—N1	−178.23 (15)	C4—S2—C20—C21	162.26 (16)
C3—C4—C5—C26	−179.13 (18)	C25—C20—C21—C22	2.6 (3)
S2—C4—C5—C26	2.5 (3)	S2—C20—C21—C22	−177.86 (16)
C3—N2—C6—C7	−171.8 (2)	C20—C21—C22—C23	0.4 (3)
N1—N2—C6—C7	7.1 (3)	C21—C22—C23—C24	−2.7 (3)
C3—N2—C6—C14	7.6 (3)	C21—C22—C23—C33	174.9 (2)
N1—N2—C6—C14	−173.51 (15)	C22—C23—C24—C25	2.0 (4)
N2—C6—C7—S1	−169.62 (14)	C33—C23—C24—C25	−175.6 (2)
C14—C6—C7—S1	11.0 (3)	C21—C20—C25—C24	−3.2 (4)
C8—S1—C7—C6	−138.30 (17)	S2—C20—C25—C24	177.26 (19)
C7—S1—C8—C9	27.9 (2)	C23—C24—C25—C20	0.9 (4)
C7—S1—C8—C13	−154.47 (16)	N1—C5—C26—C31	−37.2 (2)
C13—C8—C9—C10	1.3 (3)	C4—C5—C26—C31	142.1 (2)
S1—C8—C9—C10	178.90 (17)	N1—C5—C26—C27	139.28 (18)
C8—C9—C10—C11	−1.3 (4)	C4—C5—C26—C27	−41.5 (3)
C9—C10—C11—C12	0.0 (3)	C31—C26—C27—C28	2.1 (3)
C9—C10—C11—C32	−179.8 (2)	C5—C26—C27—C28	−174.36 (18)
C10—C11—C12—C13	1.3 (3)	C26—C27—C28—C29	−0.3 (3)
C32—C11—C12—C13	−178.9 (2)	C27—C28—C29—C30	−2.0 (3)
C11—C12—C13—C8	−1.3 (3)	C27—C28—C29—Cl2	178.72 (16)
C9—C8—C13—C12	−0.1 (3)	C28—C29—C30—C31	2.3 (3)
S1—C8—C13—C12	−177.79 (17)	Cl2—C29—C30—C31	−178.35 (16)
C7—C6—C14—C19	−108.0 (2)	C29—C30—C31—C26	−0.5 (3)
N2—C6—C14—C19	72.6 (2)	C27—C26—C31—C30	−1.7 (3)
C7—C6—C14—C15	70.0 (3)	C5—C26—C31—C30	174.82 (18)
N2—C6—C14—C15	−109.32 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33C···Cg3i	0.96	2.90	3.851 (3)	171
C9—H9···Cg5ii	0.93	3.03	3.839 (2)	147

Table 1

C—H⋯π interactions (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C33—H33C⋯Cg3i	0.96	2.90	3.851 (3)	171
C9—H9⋯Cg5ii	0.93	3.03	3.839 (2)	147

Symmetry codes: (i) ; (ii) . Cg3 and Cg5 are the centroids of the C14–C19 and C26–C31 rings, respectively.