(E)-1-[(Diphenyl-amino)meth-yl]-4-(4-fluoro-benzyl-ideneamino)-3-[1-(4-iso-butyl-phen-yl)eth-yl]-1H-1,2,4-triazole-5(4H)-thione.

The title 1,2,4-triazole compound, C(34)H(34)FN(5)S, exists in a trans configuration with respect to the acyclic C=N bond. An intra-molecular C-H⋯S contact generates a six-membered ring, producing an S(6) ring motif. The essentially planar 1,2,4-triazole ring [maximum deviation 0.008 (1) Å] is inclined at 21.43 (5) and 83.03 (6)°, respectively, with respect to the flurophenyl unit and the isobutyl-substituted benzene ring. The diphenyl-amino unit is not planar, as indicated by the dihedral angle between two phenyl rings of 76.95 (6)°. The crystal structure is stabilized by C-H⋯π and π-π [centroid-centroid distance = 3.6169 (6) Å] inter-actions; mol-ecules are stacked along the b axis.

Related literature

For general background to and applications of 1,2,4-triazole derivatives, see: Calhoun et al. (1995 ▶); Pandeya et al. (1999 ▶, 2000 ▶); Sujith et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For a closely related structure, see: Goh et al. (2010 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C34H34FN5S

M = 563.72

Monoclinic,

a = 10.8175 (2) Å

b = 9.9579 (1) Å

c = 27.8344 (4) Å

β = 105.199 (1)°

V = 2893.43 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 100 K

0.50 × 0.36 × 0.32 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.928, T max = 0.953

58342 measured reflections

10414 independent reflections

8240 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.120

S = 1.04

10414 reflections

373 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052039/tk2593sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052039/tk2593Isup2.hkl

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

C34H34FN5S	F(000) = 1192
Mr = 563.72	Dx = 1.294 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9739 reflections
a = 10.8175 (2) Å	θ = 2.6–34.7°
b = 9.9579 (1) Å	µ = 0.15 mm−1
c = 27.8344 (4) Å	T = 100 K
β = 105.199 (1)°	Block, colourless
V = 2893.43 (7) Å3	0.50 × 0.36 × 0.32 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	10414 independent reflections
Radiation source: fine-focus sealed tube	8240 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 32.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→16
Tmin = 0.928, Tmax = 0.953	k = −15→14
58342 measured reflections	l = −42→41

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.8906P] where P = (Fo2 + 2Fc2)/3
10414 reflections	(Δ/σ)max < 0.001
373 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.16117 (3)	0.22751 (3)	0.589154 (11)	0.02485 (7)
F1	0.52953 (8)	0.48389 (9)	0.37293 (3)	0.03681 (19)
N1	0.17190 (9)	0.50769 (9)	0.51987 (3)	0.01794 (17)
N2	0.11972 (9)	0.49448 (9)	0.56030 (3)	0.01672 (16)
N3	0.04413 (9)	0.43808 (9)	0.62106 (3)	0.01820 (17)
N4	0.01010 (9)	0.57105 (9)	0.61131 (3)	0.01838 (17)
N5	0.05479 (9)	0.45860 (10)	0.70862 (3)	0.02075 (18)
C1	0.29376 (11)	0.54223 (11)	0.44134 (4)	0.0207 (2)
H1A	0.2273	0.6013	0.4416	0.025*
C2	0.36276 (12)	0.55679 (12)	0.40618 (4)	0.0244 (2)
H2A	0.3438	0.6255	0.3828	0.029*
C3	0.46049 (12)	0.46680 (12)	0.40667 (4)	0.0242 (2)
C4	0.49201 (11)	0.36250 (11)	0.43997 (4)	0.0227 (2)
H4A	0.5576	0.3030	0.4390	0.027*
C5	0.42230 (11)	0.34904 (11)	0.47520 (4)	0.0200 (2)
H5A	0.4415	0.2793	0.4982	0.024*
C6	0.32382 (10)	0.43867 (10)	0.47658 (4)	0.01744 (18)
C7	0.26117 (10)	0.42571 (10)	0.51707 (4)	0.01848 (19)
H7A	0.2861	0.3581	0.5407	0.022*
C8	0.11087 (10)	0.38574 (10)	0.59048 (4)	0.01786 (19)
C9	0.05599 (10)	0.60207 (10)	0.57402 (4)	0.01684 (18)
C10	0.04846 (10)	0.73715 (10)	0.55006 (4)	0.01775 (19)
H10A	0.0237	0.7246	0.5139	0.021*
C11	0.17695 (10)	0.80893 (10)	0.56429 (4)	0.01719 (18)
C12	0.24975 (11)	0.81605 (11)	0.61379 (4)	0.0201 (2)
H12A	0.2251	0.7669	0.6381	0.024*
C13	0.35875 (11)	0.89604 (11)	0.62690 (4)	0.0211 (2)
H13A	0.4056	0.9002	0.6601	0.025*
C14	0.39935 (11)	0.97024 (10)	0.59134 (4)	0.0202 (2)
C15	0.32793 (12)	0.95927 (11)	0.54167 (4)	0.0221 (2)
H15A	0.3543	1.0058	0.5171	0.026*
C16	0.21845 (11)	0.88019 (11)	0.52838 (4)	0.0204 (2)
H16A	0.1724	0.8748	0.4952	0.024*
C17	0.51678 (11)	1.05862 (11)	0.60507 (4)	0.0229 (2)
H17A	0.5272	1.0919	0.6386	0.028*
H17B	0.5030	1.1355	0.5829	0.028*
C18	0.64135 (11)	0.98818 (10)	0.60244 (4)	0.0200 (2)
H18A	0.6264	0.9450	0.5698	0.024*
C19	0.74893 (12)	1.09067 (12)	0.60727 (5)	0.0260 (2)
H19A	0.8259	1.0454	0.6054	0.039*
H19B	0.7634	1.1361	0.6387	0.039*
H19C	0.7251	1.1549	0.5807	0.039*
C20	0.68007 (12)	0.87972 (12)	0.64228 (4)	0.0241 (2)
H20A	0.7545	0.8334	0.6382	0.036*
H20B	0.6109	0.8170	0.6390	0.036*
H20C	0.6991	0.9205	0.6746	0.036*
C21	−0.05414 (11)	0.82343 (11)	0.56409 (5)	0.0238 (2)
H21A	−0.1359	0.7798	0.5531	0.036*
H21B	−0.0580	0.9097	0.5484	0.036*
H21C	−0.0328	0.8348	0.5996	0.036*
C22	0.02287 (12)	0.37238 (11)	0.66559 (4)	0.0217 (2)
H22A	−0.0663	0.3461	0.6590	0.026*
H22B	0.0746	0.2916	0.6726	0.026*
C23	−0.04449 (10)	0.50037 (10)	0.73041 (4)	0.01839 (19)
C24	−0.15516 (11)	0.56251 (12)	0.70258 (4)	0.0222 (2)
H24A	−0.1661	0.5789	0.6688	0.027*
C25	−0.24961 (11)	0.60002 (12)	0.72568 (4)	0.0240 (2)
H25A	−0.3246	0.6400	0.7070	0.029*
C26	−0.23290 (11)	0.57828 (11)	0.77618 (4)	0.0218 (2)
H26A	−0.2961	0.6044	0.7914	0.026*
C27	−0.12167 (11)	0.51754 (11)	0.80400 (4)	0.0218 (2)
H27A	−0.1100	0.5035	0.8379	0.026*
C28	−0.02782 (11)	0.47779 (11)	0.78124 (4)	0.0209 (2)
H28A	0.0462	0.4361	0.7998	0.025*
C29	0.17503 (10)	0.52279 (11)	0.72258 (4)	0.0194 (2)
C30	0.18674 (11)	0.64932 (11)	0.74534 (4)	0.0215 (2)
H30A	0.1152	0.6899	0.7516	0.026*
C31	0.30399 (12)	0.71451 (12)	0.75856 (5)	0.0258 (2)
H31A	0.3105	0.7984	0.7737	0.031*
C32	0.41226 (12)	0.65524 (13)	0.74936 (5)	0.0277 (2)
H32A	0.4910	0.6988	0.7583	0.033*
C33	0.40086 (12)	0.53055 (13)	0.72666 (5)	0.0267 (2)
H33A	0.4729	0.4904	0.7206	0.032*
C34	0.28381 (11)	0.46417 (12)	0.71282 (4)	0.0235 (2)
H34A	0.2777	0.3811	0.6971	0.028*

	U11	U22	U33	U12	U13	U23
S1	0.03825 (17)	0.01658 (12)	0.02449 (14)	0.00605 (11)	0.01669 (12)	0.00197 (9)
F1	0.0399 (5)	0.0505 (5)	0.0279 (4)	0.0028 (4)	0.0231 (3)	−0.0001 (3)
N1	0.0216 (4)	0.0189 (4)	0.0153 (4)	0.0013 (3)	0.0085 (3)	−0.0008 (3)
N2	0.0204 (4)	0.0164 (4)	0.0151 (4)	0.0031 (3)	0.0079 (3)	0.0002 (3)
N3	0.0224 (4)	0.0173 (4)	0.0167 (4)	0.0026 (3)	0.0083 (3)	0.0001 (3)
N4	0.0202 (4)	0.0174 (4)	0.0183 (4)	0.0030 (3)	0.0063 (3)	−0.0005 (3)
N5	0.0199 (4)	0.0249 (4)	0.0198 (4)	−0.0003 (3)	0.0093 (3)	−0.0036 (3)
C1	0.0223 (5)	0.0227 (5)	0.0179 (5)	0.0033 (4)	0.0067 (4)	0.0004 (4)
C2	0.0275 (6)	0.0289 (5)	0.0177 (5)	0.0015 (5)	0.0075 (4)	0.0018 (4)
C3	0.0256 (5)	0.0318 (6)	0.0185 (5)	−0.0022 (5)	0.0117 (4)	−0.0060 (4)
C4	0.0221 (5)	0.0228 (5)	0.0253 (5)	0.0008 (4)	0.0097 (4)	−0.0072 (4)
C5	0.0210 (5)	0.0177 (4)	0.0222 (5)	0.0008 (4)	0.0073 (4)	−0.0030 (4)
C6	0.0181 (5)	0.0181 (4)	0.0167 (4)	−0.0001 (4)	0.0057 (4)	−0.0028 (3)
C7	0.0193 (5)	0.0192 (4)	0.0180 (5)	0.0005 (4)	0.0067 (4)	−0.0001 (3)
C8	0.0216 (5)	0.0174 (4)	0.0157 (4)	0.0016 (4)	0.0069 (4)	−0.0007 (3)
C9	0.0169 (4)	0.0173 (4)	0.0164 (4)	0.0024 (4)	0.0044 (4)	−0.0022 (3)
C10	0.0200 (5)	0.0168 (4)	0.0165 (4)	0.0041 (4)	0.0048 (4)	0.0006 (3)
C11	0.0196 (5)	0.0155 (4)	0.0176 (4)	0.0043 (4)	0.0067 (4)	0.0005 (3)
C12	0.0222 (5)	0.0230 (5)	0.0166 (5)	0.0018 (4)	0.0078 (4)	0.0003 (4)
C13	0.0223 (5)	0.0248 (5)	0.0167 (5)	0.0009 (4)	0.0061 (4)	−0.0021 (4)
C14	0.0217 (5)	0.0168 (4)	0.0230 (5)	0.0024 (4)	0.0076 (4)	−0.0005 (4)
C15	0.0268 (5)	0.0195 (4)	0.0209 (5)	0.0020 (4)	0.0082 (4)	0.0046 (4)
C16	0.0248 (5)	0.0196 (4)	0.0165 (4)	0.0032 (4)	0.0050 (4)	0.0032 (3)
C17	0.0244 (5)	0.0181 (4)	0.0267 (5)	−0.0001 (4)	0.0072 (4)	−0.0016 (4)
C18	0.0246 (5)	0.0188 (4)	0.0180 (5)	0.0005 (4)	0.0078 (4)	0.0000 (4)
C19	0.0278 (6)	0.0225 (5)	0.0312 (6)	−0.0012 (4)	0.0139 (5)	0.0010 (4)
C20	0.0252 (5)	0.0221 (5)	0.0234 (5)	−0.0010 (4)	0.0036 (4)	0.0024 (4)
C21	0.0211 (5)	0.0207 (5)	0.0294 (6)	0.0055 (4)	0.0064 (4)	−0.0008 (4)
C22	0.0275 (5)	0.0204 (5)	0.0198 (5)	−0.0007 (4)	0.0111 (4)	−0.0004 (4)
C23	0.0191 (5)	0.0188 (4)	0.0193 (5)	−0.0005 (4)	0.0086 (4)	−0.0014 (3)
C24	0.0248 (5)	0.0246 (5)	0.0185 (5)	0.0014 (4)	0.0078 (4)	0.0024 (4)
C25	0.0224 (5)	0.0253 (5)	0.0249 (5)	0.0038 (4)	0.0074 (4)	0.0034 (4)
C26	0.0211 (5)	0.0224 (5)	0.0247 (5)	0.0006 (4)	0.0113 (4)	−0.0011 (4)
C27	0.0239 (5)	0.0247 (5)	0.0183 (5)	0.0007 (4)	0.0083 (4)	0.0001 (4)
C28	0.0201 (5)	0.0248 (5)	0.0182 (5)	0.0025 (4)	0.0058 (4)	0.0007 (4)
C29	0.0195 (5)	0.0218 (5)	0.0184 (5)	0.0018 (4)	0.0077 (4)	0.0024 (4)
C30	0.0213 (5)	0.0212 (5)	0.0234 (5)	0.0015 (4)	0.0086 (4)	0.0018 (4)
C31	0.0264 (6)	0.0245 (5)	0.0272 (6)	−0.0026 (4)	0.0079 (5)	0.0012 (4)
C32	0.0205 (5)	0.0358 (6)	0.0272 (6)	−0.0036 (5)	0.0069 (4)	0.0043 (5)
C33	0.0209 (5)	0.0369 (6)	0.0247 (5)	0.0046 (5)	0.0104 (4)	0.0050 (5)
C34	0.0235 (5)	0.0268 (5)	0.0223 (5)	0.0035 (4)	0.0100 (4)	0.0008 (4)

S1—C8	1.6705 (11)	C17—C18	1.5378 (16)
F1—C3	1.3552 (13)	C17—H17A	0.9700
N1—C7	1.2824 (14)	C17—H17B	0.9700
N1—N2	1.3910 (12)	C18—C20	1.5257 (15)
N2—C9	1.3809 (13)	C18—C19	1.5271 (16)
N2—C8	1.3892 (13)	C18—H18A	0.9800
N3—C8	1.3562 (13)	C19—H19A	0.9600
N3—N4	1.3821 (12)	C19—H19B	0.9600
N3—C22	1.4720 (14)	C19—H19C	0.9600
N4—C9	1.2999 (14)	C20—H20A	0.9600
N5—C29	1.4095 (15)	C20—H20B	0.9600
N5—C23	1.4267 (14)	C20—H20C	0.9600
N5—C22	1.4401 (14)	C21—H21A	0.9600
C1—C2	1.3854 (16)	C21—H21B	0.9600
C1—C6	1.4014 (15)	C21—H21C	0.9600
C1—H1A	0.9300	C22—H22A	0.9700
C2—C3	1.3832 (17)	C22—H22B	0.9700
C2—H2A	0.9300	C23—C24	1.3891 (16)
C3—C4	1.3742 (17)	C23—C28	1.3968 (15)
C4—C5	1.3914 (16)	C24—C25	1.3932 (16)
C4—H4A	0.9300	C24—H24A	0.9300
C5—C6	1.3980 (15)	C25—C26	1.3863 (16)
C5—H5A	0.9300	C25—H25A	0.9300
C6—C7	1.4650 (15)	C26—C27	1.3874 (16)
C7—H7A	0.9300	C26—H26A	0.9300
C9—C10	1.4940 (14)	C27—C28	1.3879 (15)
C10—C11	1.5202 (15)	C27—H27A	0.9300
C10—C21	1.5330 (15)	C28—H28A	0.9300
C10—H10A	0.9800	C29—C30	1.4010 (16)
C11—C16	1.3926 (15)	C29—C34	1.4025 (15)
C11—C12	1.3983 (15)	C30—C31	1.3859 (17)
C12—C13	1.3900 (16)	C30—H30A	0.9300
C12—H12A	0.9300	C31—C32	1.3939 (18)
C13—C14	1.3953 (16)	C31—H31A	0.9300
C13—H13A	0.9300	C32—C33	1.3839 (19)
C14—C15	1.4000 (16)	C32—H32A	0.9300
C14—C17	1.5098 (16)	C33—C34	1.3902 (17)
C15—C16	1.3891 (16)	C33—H33A	0.9300
C15—H15A	0.9300	C34—H34A	0.9300
C16—H16A	0.9300
C7—N1—N2	117.44 (9)	H17A—C17—H17B	107.6
C9—N2—C8	108.60 (9)	C20—C18—C19	110.58 (10)
C9—N2—N1	119.22 (8)	C20—C18—C17	111.43 (9)
C8—N2—N1	132.06 (8)	C19—C18—C17	110.37 (9)
C8—N3—N4	113.78 (9)	C20—C18—H18A	108.1
C8—N3—C22	125.73 (9)	C19—C18—H18A	108.1
N4—N3—C22	119.91 (8)	C17—C18—H18A	108.1
C9—N4—N3	104.27 (8)	C18—C19—H19A	109.5
C29—N5—C23	119.58 (9)	C18—C19—H19B	109.5
C29—N5—C22	120.16 (9)	H19A—C19—H19B	109.5
C23—N5—C22	118.96 (9)	C18—C19—H19C	109.5
C2—C1—C6	120.16 (10)	H19A—C19—H19C	109.5
C2—C1—H1A	119.9	H19B—C19—H19C	109.5
C6—C1—H1A	119.9	C18—C20—H20A	109.5
C3—C2—C1	118.50 (11)	C18—C20—H20B	109.5
C3—C2—H2A	120.7	H20A—C20—H20B	109.5
C1—C2—H2A	120.7	C18—C20—H20C	109.5
F1—C3—C4	118.56 (11)	H20A—C20—H20C	109.5
F1—C3—C2	118.06 (11)	H20B—C20—H20C	109.5
C4—C3—C2	123.37 (11)	C10—C21—H21A	109.5
C3—C4—C5	117.63 (10)	C10—C21—H21B	109.5
C3—C4—H4A	121.2	H21A—C21—H21B	109.5
C5—C4—H4A	121.2	C10—C21—H21C	109.5
C4—C5—C6	121.03 (10)	H21A—C21—H21C	109.5
C4—C5—H5A	119.5	H21B—C21—H21C	109.5
C6—C5—H5A	119.5	N5—C22—N3	112.27 (9)
C5—C6—C1	119.29 (10)	N5—C22—H22A	109.1
C5—C6—C7	118.32 (10)	N3—C22—H22A	109.1
C1—C6—C7	122.27 (10)	N5—C22—H22B	109.1
N1—C7—C6	119.89 (10)	N3—C22—H22B	109.1
N1—C7—H7A	120.1	H22A—C22—H22B	107.9
C6—C7—H7A	120.1	C24—C23—C28	120.00 (10)
N3—C8—N2	102.26 (8)	C24—C23—N5	121.85 (10)
N3—C8—S1	127.33 (8)	C28—C23—N5	118.16 (10)
N2—C8—S1	130.34 (8)	C23—C24—C25	119.42 (10)
N4—C9—N2	111.06 (9)	C23—C24—H24A	120.3
N4—C9—C10	125.65 (9)	C25—C24—H24A	120.3
N2—C9—C10	123.22 (9)	C26—C25—C24	120.64 (11)
C9—C10—C11	111.58 (8)	C26—C25—H25A	119.7
C9—C10—C21	110.44 (9)	C24—C25—H25A	119.7
C11—C10—C21	110.10 (9)	C25—C26—C27	119.83 (11)
C9—C10—H10A	108.2	C25—C26—H26A	120.1
C11—C10—H10A	108.2	C27—C26—H26A	120.1
C21—C10—H10A	108.2	C26—C27—C28	120.04 (10)
C16—C11—C12	118.50 (10)	C26—C27—H27A	120.0
C16—C11—C10	119.83 (9)	C28—C27—H27A	120.0
C12—C11—C10	121.39 (9)	C27—C28—C23	120.06 (10)
C13—C12—C11	120.51 (10)	C27—C28—H28A	120.0
C13—C12—H12A	119.7	C23—C28—H28A	120.0
C11—C12—H12A	119.7	C30—C29—C34	118.75 (10)
C12—C13—C14	121.35 (10)	C30—C29—N5	120.00 (10)
C12—C13—H13A	119.3	C34—C29—N5	121.22 (10)
C14—C13—H13A	119.3	C31—C30—C29	120.61 (11)
C13—C14—C15	117.67 (10)	C31—C30—H30A	119.7
C13—C14—C17	121.98 (10)	C29—C30—H30A	119.7
C15—C14—C17	120.35 (10)	C30—C31—C32	120.49 (11)
C16—C15—C14	121.23 (10)	C30—C31—H31A	119.8
C16—C15—H15A	119.4	C32—C31—H31A	119.8
C14—C15—H15A	119.4	C33—C32—C31	119.02 (11)
C15—C16—C11	120.69 (10)	C33—C32—H32A	120.5
C15—C16—H16A	119.7	C31—C32—H32A	120.5
C11—C16—H16A	119.7	C32—C33—C34	121.25 (11)
C14—C17—C18	114.31 (9)	C32—C33—H33A	119.4
C14—C17—H17A	108.7	C34—C33—H33A	119.4
C18—C17—H17A	108.7	C33—C34—C29	119.86 (11)
C14—C17—H17B	108.7	C33—C34—H34A	120.1
C18—C17—H17B	108.7	C29—C34—H34A	120.1
C7—N1—N2—C9	159.24 (10)	C11—C12—C13—C14	−0.57 (17)
C7—N1—N2—C8	−25.33 (16)	C12—C13—C14—C15	−1.30 (16)
C8—N3—N4—C9	0.16 (12)	C12—C13—C14—C17	179.39 (10)
C22—N3—N4—C9	171.99 (10)	C13—C14—C15—C16	1.72 (16)
C6—C1—C2—C3	0.36 (17)	C17—C14—C15—C16	−178.96 (10)
C1—C2—C3—F1	−178.37 (10)	C14—C15—C16—C11	−0.26 (17)
C1—C2—C3—C4	0.72 (18)	+C12—C11—C16—C15	−1.62 (16)
F1—C3—C4—C5	178.21 (10)	C10—C11—C16—C15	172.38 (10)
C2—C3—C4—C5	−0.87 (18)	C13—C14—C17—C18	91.25 (13)
C3—C4—C5—C6	−0.04 (16)	C15—C14—C17—C18	−88.04 (13)
C4—C5—C6—C1	1.07 (16)	C14—C17—C18—C20	−67.35 (12)
C4—C5—C6—C7	−175.07 (10)	C14—C17—C18—C19	169.38 (10)
C2—C1—C6—C5	−1.22 (16)	C29—N5—C22—N3	−51.66 (14)
C2—C1—C6—C7	174.75 (11)	C23—N5—C22—N3	115.30 (11)
N2—N1—C7—C6	−177.20 (9)	C8—N3—C22—N5	129.58 (11)
C5—C6—C7—N1	178.88 (10)	N4—N3—C22—N5	−41.19 (14)
C1—C6—C7—N1	2.87 (16)	C29—N5—C23—C24	113.07 (12)
N4—N3—C8—N2	0.73 (12)	C22—N5—C23—C24	−53.97 (15)
C22—N3—C8—N2	−170.53 (10)	C29—N5—C23—C28	−66.63 (14)
N4—N3—C8—S1	−176.59 (8)	C22—N5—C23—C28	126.33 (11)
C22—N3—C8—S1	12.14 (16)	C28—C23—C24—C25	−0.94 (17)
C9—N2—C8—N3	−1.31 (11)	N5—C23—C24—C25	179.36 (10)
N1—N2—C8—N3	−177.11 (10)	C23—C24—C25—C26	1.27 (18)
C9—N2—C8—S1	175.90 (9)	C24—C25—C26—C27	−0.57 (18)
N1—N2—C8—S1	0.10 (18)	C25—C26—C27—C28	−0.47 (17)
N3—N4—C9—N2	−1.03 (12)	C26—C27—C28—C23	0.79 (17)
N3—N4—C9—C10	−178.02 (10)	C24—C23—C28—C27	−0.08 (17)
C8—N2—C9—N4	1.55 (12)	N5—C23—C28—C27	179.62 (10)
N1—N2—C9—N4	177.97 (9)	C23—N5—C29—C30	−18.94 (15)
C8—N2—C9—C10	178.62 (10)	C22—N5—C29—C30	147.93 (11)
N1—N2—C9—C10	−4.95 (15)	C23—N5—C29—C34	162.97 (10)
N4—C9—C10—C11	105.64 (12)	C22—N5—C29—C34	−30.15 (15)
N2—C9—C10—C11	−70.99 (13)	C34—C29—C30—C31	−0.87 (17)
N4—C9—C10—C21	−17.17 (15)	N5—C29—C30—C31	−178.99 (10)
N2—C9—C10—C21	166.20 (10)	C29—C30—C31—C32	0.09 (18)
C9—C10—C11—C16	138.70 (10)	C30—C31—C32—C33	0.22 (18)
C21—C10—C11—C16	−98.30 (11)	C31—C32—C33—C34	0.25 (18)
C9—C10—C11—C12	−47.47 (13)	C32—C33—C34—C29	−1.04 (18)
C21—C10—C11—C12	75.53 (12)	C30—C29—C34—C33	1.33 (17)
C16—C11—C12—C13	2.04 (16)	N5—C29—C34—C33	179.43 (10)
C10—C11—C12—C13	−171.87 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···S1	0.93	2.51	3.1983 (11)	131
C4—H4A···Cg1i	0.93	2.65	3.5688 (13)	169
C20—H20C···Cg2ii	0.96	2.99	3.9291 (12)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯S1	0.93	2.51	3.1983 (11)	131
C4—H4A⋯Cg1i	0.93	2.65	3.5688 (13)	169
C20—H20C⋯Cg2ii	0.96	2.99	3.9291 (12)	166

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the C11–C16 and C29–C34 benzene rings, respectively.