4-[5-(4-Fluoro-phen-yl)-1-(4-phenyl-1,3-thia-zol-2-yl)-4,5-dihydro-1H-pyrazol-3-yl]-5-methyl-1-(4-methyl-phenyl)-1H-1,2,3-triazole.

In the title compound, C28H23FN6S, the pyrazole ring adopts an envelope conformation, with the methine C atom being the flap atom. With respect to this ring, the 2-thienyl, triazole and fluoro-benzene rings are approximately coplanar, coplanar and perpendicular, respectively [dihedral angles = 8.56 (17), 6.03 (19) and 73.1 (2)°, respectively] so that to a first approximation the mol-ecule has a T-shape. In the crystal, mol-ecules are consolidated into a three-dimensional architecture by C-H⋯F (involving a bifurcated F atom), C-H⋯S and C-H⋯π inter-actions.

Related literature

For the synthesis, structure and biological activity of 1-thia­zol-2-ylpyrazoline, see: Abdel-Wahab et al. (2012 ▶); Dong et al. (2011 ▶).

Experimental

Crystal data

C28H23FN6S

M = 494.58

Monoclinic,

a = 17.7373 (18) Å

b = 7.8367 (7) Å

c = 19.4159 (18) Å

β = 109.323 (11)°

V = 2546.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 295 K

0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.901, T max = 1.000

16284 measured reflections

5871 independent reflections

2694 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.232

S = 1.06

5871 reflections

328 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008179/su2580sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008179/su2580Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008179/su2580Isup3.cml

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

C28H23FN6S	F(000) = 1032
Mr = 494.58	Dx = 1.290 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2615 reflections
a = 17.7373 (18) Å	θ = 2.9–27.5°
b = 7.8367 (7) Å	µ = 0.16 mm−1
c = 19.4159 (18) Å	T = 295 K
β = 109.323 (11)°	Prism, light-brown
V = 2546.8 (4) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	5871 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2694 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −23→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→7
Tmin = 0.901, Tmax = 1.000	l = −25→25
16284 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065	H-atom parameters constrained
wR(F2) = 0.232	w = 1/[σ2(Fo2) + (0.0967P)2 + 0.2203P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
5871 reflections	Δρmax = 0.35 e Å−3
328 parameters	Δρmin = −0.38 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (12)

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	0.53552 (5)	0.20817 (11)	0.54592 (4)	0.0861 (3)
F1	0.71777 (15)	0.6920 (6)	0.2659 (2)	0.248 (2)
N1	0.61200 (15)	0.1843 (3)	0.45456 (13)	0.0749 (7)
N2	0.48605 (15)	0.3127 (4)	0.40552 (13)	0.0869 (8)
N3	0.41199 (15)	0.3365 (3)	0.41211 (14)	0.0795 (7)
N4	0.22891 (18)	0.4311 (4)	0.26442 (14)	0.1003 (9)
N5	0.15671 (17)	0.4606 (4)	0.26545 (14)	0.1023 (9)
N6	0.16075 (15)	0.4627 (3)	0.33692 (13)	0.0823 (7)
C1	0.7421 (2)	0.0649 (4)	0.52615 (17)	0.0782 (8)
C2	0.7666 (2)	0.0676 (5)	0.4651 (2)	0.0999 (11)
H2	0.7319	0.1057	0.4205	0.120*
C3	0.8434 (3)	0.0133 (6)	0.4707 (3)	0.1212 (14)
H3	0.8594	0.0144	0.4297	0.145*
C4	0.8952 (3)	−0.0417 (6)	0.5361 (3)	0.1240 (15)
H4	0.9462	−0.0786	0.5398	0.149*
C5	0.8711 (3)	−0.0418 (5)	0.5959 (2)	0.1078 (12)
H5	0.9065	−0.0773	0.6407	0.129*
C6	0.7966 (2)	0.0089 (4)	0.59155 (19)	0.0888 (9)
H6	0.7816	0.0061	0.6332	0.107*
C7	0.66171 (18)	0.1232 (4)	0.52085 (16)	0.0718 (8)
C8	0.6299 (2)	0.1261 (4)	0.57531 (16)	0.0853 (9)
H8	0.6561	0.0883	0.6226	0.102*
C9	0.54482 (19)	0.2344 (4)	0.46099 (16)	0.0738 (8)
C10	0.48409 (18)	0.3077 (4)	0.32859 (16)	0.0821 (9)
H10	0.4875	0.1889	0.3141	0.099*
C11	0.39996 (18)	0.3751 (5)	0.28987 (17)	0.0931 (10)
H11A	0.4015	0.4900	0.2718	0.112*
H11B	0.3712	0.3018	0.2494	0.112*
C12	0.36238 (19)	0.3725 (4)	0.34853 (16)	0.0772 (8)
C13	0.54996 (17)	0.4088 (4)	0.31593 (15)	0.0739 (8)
C14	0.5802 (3)	0.3588 (6)	0.2630 (2)	0.1267 (15)
H14	0.5626	0.2574	0.2379	0.152*
C15	0.6349 (4)	0.4536 (11)	0.2466 (4)	0.169 (3)
H15	0.6530	0.4188	0.2090	0.203*
C16	0.6632 (3)	0.5932 (11)	0.2821 (4)	0.153 (3)
C17	0.6367 (3)	0.6507 (7)	0.3366 (3)	0.1339 (17)
H17	0.6568	0.7507	0.3618	0.161*
C18	0.5788 (2)	0.5554 (5)	0.35322 (19)	0.0985 (11)
H18	0.5597	0.5918	0.3899	0.118*
C19	0.27929 (18)	0.4113 (4)	0.33473 (17)	0.0775 (8)
C20	0.23657 (17)	0.4322 (4)	0.38183 (16)	0.0736 (8)
C21	0.26213 (18)	0.4199 (4)	0.46230 (16)	0.0849 (9)
H21A	0.3071	0.3444	0.4793	0.127*
H21B	0.2189	0.3762	0.4766	0.127*
H21C	0.2769	0.5310	0.4832	0.127*
C22	0.08855 (17)	0.4876 (4)	0.35273 (16)	0.0770 (8)
C23	0.0206 (2)	0.4008 (5)	0.31273 (19)	0.0984 (11)
H23	0.0212	0.3283	0.2750	0.118*
C24	−0.0483 (2)	0.4236 (5)	0.3297 (2)	0.1067 (12)
H24	−0.0941	0.3647	0.3027	0.128*
C25	−0.0523 (2)	0.5298 (5)	0.3849 (2)	0.0941 (10)
C26	0.0160 (2)	0.6152 (5)	0.42197 (19)	0.0967 (10)
H26	0.0154	0.6892	0.4592	0.116*
C27	0.08582 (19)	0.5965 (4)	0.40657 (17)	0.0853 (9)
H27	0.1310	0.6581	0.4328	0.102*
C28	−0.1285 (2)	0.5489 (7)	0.4025 (2)	0.1334 (16)
H28A	−0.1597	0.4466	0.3889	0.200*
H28B	−0.1585	0.6439	0.3759	0.200*
H28C	−0.1159	0.5683	0.4539	0.200*

	U11	U22	U33	U12	U13	U23
S1	0.1046 (7)	0.0881 (7)	0.0660 (5)	0.0002 (4)	0.0289 (5)	0.0001 (4)
F1	0.0915 (17)	0.367 (6)	0.276 (4)	0.002 (2)	0.048 (2)	0.218 (4)
N1	0.0815 (16)	0.0787 (17)	0.0566 (14)	−0.0108 (13)	0.0121 (12)	0.0048 (12)
N2	0.0781 (17)	0.118 (2)	0.0608 (15)	−0.0031 (15)	0.0186 (13)	0.0145 (15)
N3	0.0771 (16)	0.0888 (19)	0.0721 (17)	−0.0051 (13)	0.0240 (14)	0.0077 (14)
N4	0.103 (2)	0.128 (3)	0.0606 (17)	0.0176 (18)	0.0145 (15)	−0.0013 (16)
N5	0.090 (2)	0.139 (3)	0.0665 (18)	0.0237 (18)	0.0114 (15)	0.0037 (17)
N6	0.0872 (18)	0.0913 (19)	0.0545 (14)	0.0063 (14)	0.0045 (13)	−0.0023 (13)
C1	0.099 (2)	0.0612 (18)	0.0675 (19)	−0.0033 (16)	0.0189 (18)	−0.0079 (15)
C2	0.110 (3)	0.103 (3)	0.080 (2)	0.010 (2)	0.023 (2)	−0.011 (2)
C3	0.124 (3)	0.138 (4)	0.109 (3)	0.015 (3)	0.049 (3)	−0.027 (3)
C4	0.107 (3)	0.113 (3)	0.145 (4)	0.024 (2)	0.032 (3)	−0.026 (3)
C5	0.116 (3)	0.088 (3)	0.103 (3)	0.014 (2)	0.014 (2)	−0.006 (2)
C6	0.093 (2)	0.080 (2)	0.085 (2)	0.0113 (18)	0.0173 (19)	0.0024 (18)
C7	0.087 (2)	0.0567 (17)	0.0628 (18)	−0.0061 (15)	0.0131 (15)	−0.0022 (14)
C8	0.110 (2)	0.085 (2)	0.0560 (17)	−0.0018 (18)	0.0210 (17)	0.0003 (16)
C9	0.0779 (19)	0.071 (2)	0.0670 (19)	−0.0120 (16)	0.0167 (16)	0.0023 (15)
C10	0.087 (2)	0.093 (2)	0.0625 (18)	−0.0042 (17)	0.0189 (16)	−0.0001 (17)
C11	0.078 (2)	0.125 (3)	0.068 (2)	−0.0075 (19)	0.0123 (16)	0.005 (2)
C12	0.086 (2)	0.080 (2)	0.0606 (18)	−0.0112 (17)	0.0175 (16)	−0.0003 (16)
C13	0.0767 (18)	0.093 (2)	0.0514 (16)	0.0136 (17)	0.0205 (14)	0.0038 (16)
C14	0.161 (4)	0.135 (4)	0.112 (3)	0.027 (3)	0.083 (3)	0.012 (3)
C15	0.143 (5)	0.243 (8)	0.164 (6)	0.060 (5)	0.107 (5)	0.070 (6)
C16	0.069 (2)	0.235 (8)	0.148 (5)	0.006 (4)	0.026 (3)	0.120 (6)
C17	0.118 (3)	0.150 (4)	0.107 (3)	−0.044 (3)	0.001 (3)	0.034 (3)
C18	0.105 (3)	0.113 (3)	0.079 (2)	−0.012 (2)	0.033 (2)	0.000 (2)
C19	0.0764 (19)	0.080 (2)	0.0680 (19)	−0.0005 (15)	0.0126 (16)	0.0001 (16)
C20	0.0786 (19)	0.0703 (19)	0.0626 (18)	−0.0070 (15)	0.0108 (16)	−0.0041 (15)
C21	0.0791 (19)	0.099 (2)	0.0642 (19)	−0.0076 (17)	0.0077 (15)	0.0022 (17)
C22	0.0748 (19)	0.078 (2)	0.0689 (19)	0.0059 (16)	0.0108 (15)	0.0019 (17)
C23	0.086 (2)	0.091 (3)	0.093 (2)	0.0097 (19)	−0.0051 (19)	−0.024 (2)
C24	0.067 (2)	0.099 (3)	0.126 (3)	0.0049 (18)	−0.006 (2)	−0.010 (2)
C25	0.078 (2)	0.104 (3)	0.088 (2)	0.0078 (19)	0.0110 (18)	0.013 (2)
C26	0.088 (2)	0.116 (3)	0.080 (2)	−0.001 (2)	0.0200 (19)	−0.010 (2)
C27	0.085 (2)	0.089 (2)	0.074 (2)	−0.0084 (17)	0.0150 (17)	−0.0117 (18)
C28	0.081 (2)	0.182 (5)	0.130 (3)	0.019 (3)	0.024 (2)	0.031 (3)

S1—C8	1.706 (3)	C11—H11A	0.9700
S1—C9	1.723 (3)	C11—H11B	0.9700
F1—C16	1.355 (6)	C12—C19	1.441 (4)
N1—C9	1.299 (4)	C13—C18	1.364 (5)
N1—C7	1.383 (4)	C13—C14	1.365 (4)
N2—C9	1.371 (4)	C14—C15	1.341 (8)
N2—N3	1.374 (3)	C14—H14	0.9300
N2—C10	1.483 (4)	C15—C16	1.301 (9)
N3—C12	1.288 (4)	C15—H15	0.9300
N4—N5	1.308 (4)	C16—C17	1.369 (8)
N4—C19	1.371 (4)	C17—C18	1.391 (5)
N5—N6	1.366 (3)	C17—H17	0.9300
N6—C20	1.360 (4)	C18—H18	0.9300
N6—C22	1.426 (4)	C19—C20	1.377 (4)
C1—C6	1.388 (4)	C20—C21	1.479 (4)
C1—C2	1.392 (4)	C21—H21A	0.9600
C1—C7	1.468 (4)	C21—H21B	0.9600
C2—C3	1.396 (5)	C21—H21C	0.9600
C2—H2	0.9300	C22—C27	1.363 (4)
C3—C4	1.368 (6)	C22—C23	1.378 (4)
C3—H3	0.9300	C23—C24	1.378 (5)
C4—C5	1.363 (6)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.378 (5)
C5—C6	1.356 (5)	C24—H24	0.9300
C5—H5	0.9300	C25—C26	1.362 (5)
C6—H6	0.9300	C25—C28	1.508 (5)
C7—C8	1.353 (4)	C26—C27	1.374 (4)
C8—H8	0.9300	C26—H26	0.9300
C10—C13	1.498 (4)	C27—H27	0.9300
C10—C11	1.526 (4)	C28—H28A	0.9600
C10—H10	0.9800	C28—H28B	0.9600
C11—C12	1.498 (4)	C28—H28C	0.9600
C8—S1—C9	88.34 (15)	C18—C13—C10	122.3 (3)
C9—N1—C7	109.7 (2)	C14—C13—C10	119.6 (4)
C9—N2—N3	119.3 (2)	C15—C14—C13	121.0 (5)
C9—N2—C10	122.5 (3)	C15—C14—H14	119.5
N3—N2—C10	113.1 (2)	C13—C14—H14	119.5
C12—N3—N2	108.2 (2)	C16—C15—C14	121.5 (6)
N5—N4—C19	108.9 (2)	C16—C15—H15	119.2
N4—N5—N6	107.2 (2)	C14—C15—H15	119.2
C20—N6—N5	111.0 (2)	C15—C16—F1	122.5 (8)
C20—N6—C22	130.8 (3)	C15—C16—C17	121.0 (5)
N5—N6—C22	118.1 (2)	F1—C16—C17	116.5 (8)
C6—C1—C2	117.7 (3)	C16—C17—C18	118.1 (5)
C6—C1—C7	121.9 (3)	C16—C17—H17	120.9
C2—C1—C7	120.4 (3)	C18—C17—H17	120.9
C1—C2—C3	120.1 (4)	C13—C18—C17	120.3 (4)
C1—C2—H2	120.0	C13—C18—H18	119.8
C3—C2—H2	120.0	C17—C18—H18	119.8
C4—C3—C2	120.4 (4)	N4—C19—C20	109.1 (3)
C4—C3—H3	119.8	N4—C19—C12	119.9 (3)
C2—C3—H3	119.8	C20—C19—C12	131.0 (3)
C5—C4—C3	119.2 (4)	N6—C20—C19	103.9 (3)
C5—C4—H4	120.4	N6—C20—C21	125.5 (3)
C3—C4—H4	120.4	C19—C20—C21	130.6 (3)
C6—C5—C4	121.3 (4)	C20—C21—H21A	109.5
C6—C5—H5	119.3	C20—C21—H21B	109.5
C4—C5—H5	119.3	H21A—C21—H21B	109.5
C5—C6—C1	121.3 (3)	C20—C21—H21C	109.5
C5—C6—H6	119.4	H21A—C21—H21C	109.5
C1—C6—H6	119.4	H21B—C21—H21C	109.5
C8—C7—N1	114.8 (3)	C27—C22—C23	119.7 (3)
C8—C7—C1	126.6 (3)	C27—C22—N6	120.9 (3)
N1—C7—C1	118.6 (3)	C23—C22—N6	119.5 (3)
C7—C8—S1	111.2 (2)	C22—C23—C24	118.7 (3)
C7—C8—H8	124.4	C22—C23—H23	120.6
S1—C8—H8	124.4	C24—C23—H23	120.6
N1—C9—N2	122.9 (3)	C25—C24—C23	122.8 (3)
N1—C9—S1	115.9 (2)	C25—C24—H24	118.6
N2—C9—S1	121.1 (2)	C23—C24—H24	118.6
N2—C10—C13	113.1 (3)	C26—C25—C24	116.3 (3)
N2—C10—C11	100.4 (2)	C26—C25—C28	122.6 (4)
C13—C10—C11	115.1 (3)	C24—C25—C28	121.1 (4)
N2—C10—H10	109.3	C25—C26—C27	122.7 (4)
C13—C10—H10	109.3	C25—C26—H26	118.6
C11—C10—H10	109.3	C27—C26—H26	118.6
C12—C11—C10	103.3 (3)	C22—C27—C26	119.8 (3)
C12—C11—H11A	111.1	C22—C27—H27	120.1
C10—C11—H11A	111.1	C26—C27—H27	120.1
C12—C11—H11B	111.1	C25—C28—H28A	109.5
C10—C11—H11B	111.1	C25—C28—H28B	109.5
H11A—C11—H11B	109.1	H28A—C28—H28B	109.5
N3—C12—C19	123.9 (3)	C25—C28—H28C	109.5
N3—C12—C11	113.4 (3)	H28A—C28—H28C	109.5
C19—C12—C11	122.7 (3)	H28B—C28—H28C	109.5
C18—C13—C14	118.0 (4)
C9—N2—N3—C12	−164.7 (3)	C11—C10—C13—C18	80.7 (4)
C10—N2—N3—C12	−9.1 (4)	N2—C10—C13—C14	149.4 (3)
C19—N4—N5—N6	1.0 (4)	C11—C10—C13—C14	−96.0 (4)
N4—N5—N6—C20	−0.7 (4)	C18—C13—C14—C15	−2.0 (6)
N4—N5—N6—C22	−178.1 (3)	C10—C13—C14—C15	174.9 (4)
C6—C1—C2—C3	0.7 (5)	C13—C14—C15—C16	2.4 (9)
C7—C1—C2—C3	179.5 (3)	C14—C15—C16—F1	−179.2 (4)
C1—C2—C3—C4	−0.5 (6)	C14—C15—C16—C17	−1.5 (10)
C2—C3—C4—C5	−0.4 (7)	C15—C16—C17—C18	0.2 (9)
C3—C4—C5—C6	1.1 (7)	F1—C16—C17—C18	178.1 (4)
C4—C5—C6—C1	−0.8 (6)	C14—C13—C18—C17	0.7 (6)
C2—C1—C6—C5	−0.1 (5)	C10—C13—C18—C17	−176.1 (3)
C7—C1—C6—C5	−178.8 (3)	C16—C17—C18—C13	0.2 (6)
C9—N1—C7—C8	1.2 (4)	N5—N4—C19—C20	−1.0 (4)
C9—N1—C7—C1	−178.0 (2)	N5—N4—C19—C12	178.2 (3)
C6—C1—C7—C8	−2.0 (5)	N3—C12—C19—N4	−173.3 (3)
C2—C1—C7—C8	179.4 (3)	C11—C12—C19—N4	8.5 (5)
C6—C1—C7—N1	177.2 (3)	N3—C12—C19—C20	5.6 (6)
C2—C1—C7—N1	−1.5 (4)	C11—C12—C19—C20	−172.6 (3)
N1—C7—C8—S1	−0.5 (4)	N5—N6—C20—C19	0.1 (4)
C1—C7—C8—S1	178.6 (2)	C22—N6—C20—C19	177.1 (3)
C9—S1—C8—C7	−0.2 (2)	N5—N6—C20—C21	−177.9 (3)
C7—N1—C9—N2	175.1 (3)	C22—N6—C20—C21	−0.9 (5)
C7—N1—C9—S1	−1.3 (3)	N4—C19—C20—N6	0.5 (4)
N3—N2—C9—N1	169.3 (3)	C12—C19—C20—N6	−178.5 (3)
C10—N2—C9—N1	16.1 (5)	N4—C19—C20—C21	178.4 (3)
N3—N2—C9—S1	−14.5 (4)	C12—C19—C20—C21	−0.7 (6)
C10—N2—C9—S1	−167.7 (2)	C20—N6—C22—C27	47.5 (5)
C8—S1—C9—N1	0.9 (2)	N5—N6—C22—C27	−135.7 (3)
C8—S1—C9—N2	−175.6 (3)	C20—N6—C22—C23	−132.9 (4)
C9—N2—C10—C13	−69.1 (4)	N5—N6—C22—C23	44.0 (4)
N3—N2—C10—C13	136.2 (3)	C27—C22—C23—C24	−1.7 (5)
C9—N2—C10—C11	167.7 (3)	N6—C22—C23—C24	178.7 (3)
N3—N2—C10—C11	13.0 (3)	C22—C23—C24—C25	0.1 (6)
N2—C10—C11—C12	−11.4 (3)	C23—C24—C25—C26	1.1 (6)
C13—C10—C11—C12	−133.1 (3)	C23—C24—C25—C28	−179.0 (3)
N2—N3—C12—C19	−177.9 (3)	C24—C25—C26—C27	−0.8 (6)
N2—N3—C12—C11	0.5 (4)	C28—C25—C26—C27	179.2 (3)
C10—C11—C12—N3	7.6 (4)	C23—C22—C27—C26	1.9 (5)
C10—C11—C12—C19	−174.0 (3)	N6—C22—C27—C26	−178.4 (3)
N2—C10—C13—C18	−33.9 (4)	C25—C26—C27—C22	−0.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···S1i	0.93	2.87	3.743 (4)	156
C24—H24···F1ii	0.93	2.55	3.476 (5)	177
C28—H28B···F1iii	0.96	2.53	3.308 (5)	138
C27—H27···Cg1i	0.93	2.75	3.518 (4)	141
C14—H14···Cg2ii	0.93	2.85	3.756 (5)	164

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C22–C27 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯S1i	0.93	2.87	3.743 (4)	156
C24—H24⋯F1ii	0.93	2.55	3.476 (5)	177
C28—H28B⋯F1iii	0.96	2.53	3.308 (5)	138
C27—H27⋯Cg1i	0.93	2.75	3.518 (4)	141
C14—H14⋯Cg2ii	0.93	2.85	3.756 (5)	164

Symmetry codes: (i) ; (ii) ; (iii) .