(E)-4-[(4-Fluoro-benzyl-idene)amino]-3-[1-(4-isobutyl-phen-yl)eth-yl]-1-(morpholino-meth-yl)-1H-1,2,4-triazole-5(4H)-thione methanol hemisolvate.

In the title compound, C(26)H(32)FN(5)OS·0.5CH(4)O, the methyl group of the methanol solvent mol-ecule is disordered over two sites with equal occupancies and the solvent is further disordered about a crystallographic twofold rotation axis. The organic mol-ecule exists in a trans configuration with respect to the acyclic C=N bond. An intra-molecular C-H⋯S hydrogen bond generates an S(6) ring motif. The morpholine ring adopts a chair conformation. The essentially planar 1,2,4-triazole ring [maximum deviation = 0.013 (2) Å] forms dihedral angles of 11.21 (10) and 67.53 (11)°, respectively, with the fluoro-phenyl unit and the isobutyl-substituted benzene ring. The crystal structure is stabilized by a weak inter-molecular C-H⋯π inter-action.

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 graph-set descriptions of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For closely related structures, see: Goh et al. (2010 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C26H32FN5OS·0.5CH4O

M = 497.65

Monoclinic,

a = 40.186 (3) Å

b = 4.7840 (3) Å

c = 30.073 (2) Å

β = 116.112 (2)°

V = 5191.5 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.16 mm−1

T = 100 K

0.31 × 0.16 × 0.06 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.951, T max = 0.990

24705 measured reflections

5921 independent reflections

4378 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.149

S = 1.04

5921 reflections

337 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536810015217/lh5026sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015217/lh5026Isup2.hkl

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

C26H32FN5OS·0.5CH4O	F(000) = 2120
Mr = 497.65	Dx = 1.273 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4090 reflections
a = 40.186 (3) Å	θ = 2.3–29.3°
b = 4.7840 (3) Å	µ = 0.16 mm−1
c = 30.073 (2) Å	T = 100 K
β = 116.112 (2)°	Plate, colourless
V = 5191.5 (6) Å3	0.31 × 0.16 × 0.06 mm
Z = 8

Bruker APEXII DUO CCD area-detector diffractometer	5921 independent reflections
Radiation source: fine-focus sealed tube	4378 reflections with I > 2σ(I)
graphite	Rint = 0.056
φ and ω scans	θmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −45→52
Tmin = 0.951, Tmax = 0.990	k = −6→6
24705 measured reflections	l = −39→36

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0761P)2 + 4.918P] where P = (Fo2 + 2Fc2)/3
5921 reflections	(Δ/σ)max < 0.001
337 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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	Occ. (<1)
S1	0.088287 (13)	0.32232 (11)	0.024927 (18)	0.02279 (15)
F1	−0.03130 (3)	1.5045 (3)	0.10905 (5)	0.0353 (3)
O1	0.25668 (4)	0.2919 (3)	0.07215 (6)	0.0265 (3)
N1	0.09867 (4)	0.7033 (3)	0.12673 (6)	0.0176 (3)
N2	0.12134 (4)	0.4899 (3)	0.12369 (6)	0.0161 (3)
N3	0.15083 (4)	0.1724 (3)	0.10553 (6)	0.0172 (3)
N4	0.17235 (4)	0.2366 (4)	0.15492 (6)	0.0188 (4)
N5	0.19454 (4)	0.0176 (3)	0.07277 (6)	0.0174 (3)
C1	0.05201 (5)	1.1031 (4)	0.14003 (8)	0.0219 (4)
H1A	0.0759	1.0874	0.1654	0.026*
C2	0.02764 (6)	1.2953 (5)	0.14380 (8)	0.0252 (4)
H2A	0.0347	1.4080	0.1717	0.030*
C3	−0.00756 (6)	1.3156 (4)	0.10502 (8)	0.0247 (4)
C4	−0.01956 (6)	1.1530 (4)	0.06315 (8)	0.0242 (4)
H4A	−0.0433	1.1730	0.0376	0.029*
C5	0.00502 (5)	0.9582 (5)	0.06043 (8)	0.0228 (4)
H5A	−0.0026	0.8424	0.0328	0.027*
C6	0.04086 (5)	0.9323 (4)	0.09816 (7)	0.0187 (4)
C7	0.06528 (5)	0.7189 (4)	0.09341 (7)	0.0201 (4)
H7A	0.0566	0.5971	0.0666	0.024*
C8	0.11940 (5)	0.3259 (4)	0.08433 (7)	0.0172 (4)
C9	0.15399 (5)	0.4326 (4)	0.16470 (7)	0.0170 (4)
C10	0.16652 (5)	0.5789 (4)	0.21346 (7)	0.0176 (4)
H10A	0.1552	0.7650	0.2069	0.021*
C11	0.15292 (5)	0.4252 (4)	0.24672 (7)	0.0189 (4)
C12	0.17420 (6)	0.2223 (5)	0.28014 (8)	0.0248 (4)
H12A	0.1974	0.1772	0.2824	0.030*
C13	0.16132 (7)	0.0854 (5)	0.31034 (8)	0.0299 (5)
H13A	0.1762	−0.0478	0.3328	0.036*
C14	0.12667 (6)	0.1438 (4)	0.30763 (7)	0.0244 (5)
C15	0.10542 (6)	0.3483 (5)	0.27433 (7)	0.0253 (5)
H15A	0.0822	0.3929	0.2720	0.030*
C16	0.11845 (5)	0.4869 (5)	0.24448 (7)	0.0230 (4)
H16A	0.1038	0.6235	0.2226	0.028*
C17	0.11276 (7)	−0.0019 (5)	0.34084 (8)	0.0287 (5)
H17A	0.1268	−0.1728	0.3532	0.034*
H17B	0.0871	−0.0539	0.3212	0.034*
C18	0.11550 (6)	0.1720 (5)	0.38489 (7)	0.0233 (4)
H18A	0.1010	0.3432	0.3721	0.028*
C19	0.09868 (7)	0.0110 (5)	0.41376 (9)	0.0335 (5)
H19A	0.0736	−0.0387	0.3920	0.050*
H19B	0.0990	0.1258	0.4401	0.050*
H19C	0.1129	−0.1556	0.4273	0.050*
C20	0.15534 (6)	0.2551 (6)	0.41852 (8)	0.0357 (6)
H20A	0.1647	0.3705	0.4004	0.054*
H20B	0.1703	0.0901	0.4299	0.054*
H20C	0.1561	0.3570	0.4465	0.054*
C21	0.20863 (5)	0.6187 (5)	0.23668 (8)	0.0245 (5)
H21A	0.2149	0.7449	0.2167	0.037*
H21B	0.2204	0.4415	0.2385	0.037*
H21C	0.2170	0.6945	0.2694	0.037*
C22	0.16324 (5)	−0.0479 (4)	0.08182 (7)	0.0190 (4)
H22A	0.1692	−0.2133	0.1026	0.023*
H22B	0.1426	−0.0954	0.0504	0.023*
C23	0.18987 (6)	0.2658 (4)	0.04242 (8)	0.0224 (4)
H23A	0.1892	0.4312	0.0606	0.027*
H23B	0.1666	0.2543	0.0126	0.027*
C24	0.22178 (6)	0.2869 (5)	0.02871 (8)	0.0279 (5)
H24A	0.2211	0.1285	0.0082	0.033*
H24B	0.2192	0.4559	0.0096	0.033*
C25	0.26073 (5)	0.0439 (5)	0.10014 (8)	0.0249 (5)
H25A	0.2846	0.0452	0.1290	0.030*
H25B	0.2599	−0.1176	0.0802	0.030*
C26	0.23025 (5)	0.0222 (5)	0.11653 (8)	0.0230 (4)
H26A	0.2333	−0.1472	0.1357	0.028*
H26B	0.2314	0.1807	0.1373	0.028*
O2	0.00036 (14)	0.8833 (15)	0.27352 (18)	0.091 (2)	0.50
H2OA	−0.0207	0.8835	0.2737	0.136*	0.25
H2OB	−0.0184	0.8489	0.2463	0.136*	0.25
C27A	0.0135 (4)	1.187 (3)	0.2744 (6)	0.068 (4)	0.25
H27A	−0.0076	1.3084	0.2593	0.102*	0.25
H27B	0.0281	1.2435	0.3082	0.102*	0.25
H27C	0.0282	1.1993	0.2566	0.102*	0.25
C27B	0.0229 (3)	0.616 (2)	0.2923 (4)	0.039 (2)	0.25
H27D	0.0065	0.4596	0.2860	0.059*	0.25
H27E	0.0383	0.5891	0.2757	0.059*	0.25
H27F	0.0382	0.6333	0.3272	0.059*	0.25

	U11	U22	U33	U12	U13	U23
S1	0.0194 (3)	0.0310 (3)	0.0140 (2)	0.0030 (2)	0.00371 (19)	−0.00443 (19)
F1	0.0279 (7)	0.0307 (7)	0.0483 (8)	0.0099 (5)	0.0178 (6)	−0.0043 (6)
O1	0.0207 (7)	0.0301 (8)	0.0299 (8)	−0.0040 (6)	0.0123 (6)	0.0000 (6)
N1	0.0165 (8)	0.0198 (8)	0.0174 (8)	0.0025 (6)	0.0083 (6)	−0.0002 (6)
N2	0.0150 (7)	0.0198 (8)	0.0132 (7)	0.0009 (6)	0.0059 (6)	−0.0014 (6)
N3	0.0156 (8)	0.0230 (8)	0.0142 (8)	0.0007 (6)	0.0075 (6)	−0.0014 (6)
N4	0.0177 (8)	0.0250 (9)	0.0142 (8)	−0.0004 (6)	0.0075 (6)	0.0005 (6)
N5	0.0161 (8)	0.0208 (8)	0.0159 (8)	0.0013 (6)	0.0075 (6)	0.0009 (6)
C1	0.0187 (9)	0.0219 (10)	0.0233 (10)	−0.0005 (8)	0.0075 (8)	−0.0008 (8)
C2	0.0254 (11)	0.0245 (10)	0.0260 (11)	−0.0019 (8)	0.0115 (9)	−0.0062 (8)
C3	0.0215 (10)	0.0218 (10)	0.0345 (12)	0.0057 (8)	0.0157 (9)	0.0018 (9)
C4	0.0179 (9)	0.0293 (11)	0.0231 (10)	0.0031 (8)	0.0068 (8)	0.0049 (8)
C5	0.0204 (10)	0.0277 (11)	0.0192 (10)	0.0008 (8)	0.0078 (8)	−0.0004 (8)
C6	0.0172 (9)	0.0206 (9)	0.0187 (9)	0.0018 (7)	0.0085 (8)	0.0025 (7)
C7	0.0177 (9)	0.0246 (10)	0.0176 (9)	−0.0003 (8)	0.0075 (8)	−0.0021 (8)
C8	0.0169 (9)	0.0190 (9)	0.0177 (9)	−0.0012 (7)	0.0095 (7)	−0.0011 (7)
C9	0.0149 (9)	0.0220 (9)	0.0145 (9)	−0.0005 (7)	0.0070 (7)	0.0028 (7)
C10	0.0168 (9)	0.0208 (9)	0.0139 (9)	0.0007 (7)	0.0056 (7)	−0.0001 (7)
C11	0.0218 (10)	0.0217 (9)	0.0129 (9)	−0.0031 (8)	0.0074 (7)	−0.0045 (7)
C12	0.0277 (11)	0.0263 (11)	0.0235 (10)	0.0067 (8)	0.0140 (9)	0.0010 (8)
C13	0.0408 (13)	0.0260 (11)	0.0250 (11)	0.0077 (10)	0.0165 (10)	0.0055 (9)
C14	0.0328 (11)	0.0226 (10)	0.0187 (10)	−0.0064 (8)	0.0121 (9)	−0.0048 (8)
C15	0.0216 (10)	0.0357 (12)	0.0186 (10)	−0.0042 (9)	0.0089 (8)	−0.0011 (9)
C16	0.0189 (9)	0.0312 (11)	0.0154 (9)	−0.0011 (8)	0.0044 (8)	0.0009 (8)
C17	0.0397 (13)	0.0253 (11)	0.0251 (11)	−0.0080 (9)	0.0179 (10)	−0.0020 (9)
C18	0.0251 (10)	0.0274 (11)	0.0192 (10)	−0.0006 (8)	0.0113 (8)	0.0010 (8)
C19	0.0372 (13)	0.0399 (13)	0.0294 (12)	−0.0025 (10)	0.0200 (10)	0.0032 (10)
C20	0.0314 (12)	0.0520 (16)	0.0233 (11)	−0.0063 (11)	0.0117 (10)	−0.0046 (10)
C21	0.0172 (10)	0.0330 (12)	0.0207 (10)	−0.0027 (8)	0.0059 (8)	−0.0017 (8)
C22	0.0194 (9)	0.0194 (9)	0.0195 (9)	−0.0007 (7)	0.0096 (8)	−0.0033 (7)
C23	0.0211 (10)	0.0268 (11)	0.0211 (10)	0.0020 (8)	0.0108 (8)	0.0040 (8)
C24	0.0252 (11)	0.0366 (12)	0.0249 (11)	−0.0015 (9)	0.0139 (9)	0.0040 (9)
C25	0.0179 (10)	0.0286 (11)	0.0272 (11)	0.0010 (8)	0.0092 (8)	−0.0008 (9)
C26	0.0172 (9)	0.0282 (11)	0.0222 (10)	0.0011 (8)	0.0073 (8)	0.0025 (8)
O2	0.056 (3)	0.165 (6)	0.056 (3)	−0.004 (4)	0.031 (3)	0.012 (3)
C27A	0.056 (8)	0.060 (8)	0.092 (11)	−0.010 (6)	0.037 (7)	−0.019 (7)
C27B	0.038 (5)	0.057 (7)	0.030 (5)	−0.009 (5)	0.021 (4)	0.003 (5)

S1—C8	1.6699 (19)	C16—H16A	0.9300
F1—C3	1.358 (2)	C17—C18	1.527 (3)
O1—C25	1.422 (3)	C17—H17A	0.9700
O1—C24	1.436 (3)	C17—H17B	0.9700
N1—C7	1.276 (2)	C18—C20	1.523 (3)
N1—N2	1.398 (2)	C18—C19	1.523 (3)
N2—C9	1.376 (2)	C18—H18A	0.9800
N2—C8	1.393 (2)	C19—H19A	0.9600
N3—C8	1.354 (2)	C19—H19B	0.9600
N3—N4	1.385 (2)	C19—H19C	0.9600
N3—C22	1.477 (2)	C20—H20A	0.9600
N4—C9	1.304 (3)	C20—H20B	0.9600
N5—C22	1.434 (2)	C20—H20C	0.9600
N5—C23	1.458 (3)	C21—H21A	0.9600
N5—C26	1.459 (2)	C21—H21B	0.9600
C1—C2	1.384 (3)	C21—H21C	0.9600
C1—C6	1.399 (3)	C22—H22A	0.9700
C1—H1A	0.9300	C22—H22B	0.9700
C2—C3	1.385 (3)	C23—C24	1.513 (3)
C2—H2A	0.9300	C23—H23A	0.9700
C3—C4	1.374 (3)	C23—H23B	0.9700
C4—C5	1.387 (3)	C24—H24A	0.9700
C4—H4A	0.9300	C24—H24B	0.9700
C5—C6	1.392 (3)	C25—C26	1.512 (3)
C5—H5A	0.9300	C25—H25A	0.9700
C6—C7	1.466 (3)	C25—H25B	0.9700
C7—H7A	0.9300	C26—H26A	0.9700
C9—C10	1.498 (3)	C26—H26B	0.9700
C10—C11	1.524 (3)	O2—O2i	1.402 (10)
C10—C21	1.532 (3)	O2—C27B	1.522 (13)
C10—H10A	0.9800	O2—C27A	1.543 (15)
C11—C12	1.388 (3)	O2—H2OA	0.8503
C11—C16	1.389 (3)	O2—H2OB	0.8499
C12—C13	1.391 (3)	C27A—C27Ai	1.39 (3)
C12—H12A	0.9300	C27A—H27A	0.9600
C13—C14	1.387 (3)	C27A—H27B	0.9600
C13—H13A	0.9300	C27A—H27C	0.9602
C14—C15	1.392 (3)	C27B—H27D	0.9600
C14—C17	1.513 (3)	C27B—H27E	0.9602
C15—C16	1.390 (3)	C27B—H27F	0.9601
C15—H15A	0.9300
C25—O1—C24	109.65 (16)	C18—C19—H19A	109.5
C7—N1—N2	118.83 (16)	C18—C19—H19B	109.5
C9—N2—C8	108.91 (15)	H19A—C19—H19B	109.5
C9—N2—N1	118.60 (15)	C18—C19—H19C	109.5
C8—N2—N1	132.25 (15)	H19A—C19—H19C	109.5
C8—N3—N4	113.44 (15)	H19B—C19—H19C	109.5
C8—N3—C22	127.08 (16)	C18—C20—H20A	109.5
N4—N3—C22	119.48 (15)	C18—C20—H20B	109.5
C9—N4—N3	104.66 (15)	H20A—C20—H20B	109.5
C22—N5—C23	114.50 (15)	C18—C20—H20C	109.5
C22—N5—C26	115.40 (16)	H20A—C20—H20C	109.5
C23—N5—C26	110.90 (16)	H20B—C20—H20C	109.5
C2—C1—C6	120.26 (18)	C10—C21—H21A	109.5
C2—C1—H1A	119.9	C10—C21—H21B	109.5
C6—C1—H1A	119.9	H21A—C21—H21B	109.5
C1—C2—C3	118.35 (19)	C10—C21—H21C	109.5
C1—C2—H2A	120.8	H21A—C21—H21C	109.5
C3—C2—H2A	120.8	H21B—C21—H21C	109.5
F1—C3—C4	118.77 (19)	N5—C22—N3	116.51 (16)
F1—C3—C2	117.96 (19)	N5—C22—H22A	108.2
C4—C3—C2	123.26 (19)	N3—C22—H22A	108.2
C3—C4—C5	117.56 (19)	N5—C22—H22B	108.2
C3—C4—H4A	121.2	N3—C22—H22B	108.2
C5—C4—H4A	121.2	H22A—C22—H22B	107.3
C4—C5—C6	121.33 (19)	N5—C23—C24	109.50 (17)
C4—C5—H5A	119.3	N5—C23—H23A	109.8
C6—C5—H5A	119.3	C24—C23—H23A	109.8
C5—C6—C1	119.22 (18)	N5—C23—H23B	109.8
C5—C6—C7	118.64 (18)	C24—C23—H23B	109.8
C1—C6—C7	122.11 (17)	H23A—C23—H23B	108.2
N1—C7—C6	118.84 (18)	O1—C24—C23	111.04 (17)
N1—C7—H7A	120.6	O1—C24—H24A	109.4
C6—C7—H7A	120.6	C23—C24—H24A	109.4
N3—C8—N2	102.32 (15)	O1—C24—H24B	109.4
N3—C8—S1	127.05 (15)	C23—C24—H24B	109.4
N2—C8—S1	130.55 (14)	H24A—C24—H24B	108.0
N4—C9—N2	110.62 (16)	O1—C25—C26	110.62 (17)
N4—C9—C10	125.22 (17)	O1—C25—H25A	109.5
N2—C9—C10	124.16 (17)	C26—C25—H25A	109.5
C9—C10—C11	110.73 (16)	O1—C25—H25B	109.5
C9—C10—C21	109.42 (16)	C26—C25—H25B	109.5
C11—C10—C21	113.83 (16)	H25A—C25—H25B	108.1
C9—C10—H10A	107.5	N5—C26—C25	108.87 (17)
C11—C10—H10A	107.5	N5—C26—H26A	109.9
C21—C10—H10A	107.5	C25—C26—H26A	109.9
C12—C11—C16	117.86 (19)	N5—C26—H26B	109.9
C12—C11—C10	121.88 (18)	C25—C26—H26B	109.9
C16—C11—C10	120.27 (18)	H26A—C26—H26B	108.3
C11—C12—C13	120.9 (2)	O2i—O2—C27B	96.8 (5)
C11—C12—H12A	119.5	O2i—O2—C27A	82.7 (6)
C13—C12—H12A	119.5	C27B—O2—C27A	129.9 (7)
C14—C13—C12	121.3 (2)	O2i—O2—H2OA	115.4
C14—C13—H13A	119.4	C27B—O2—H2OA	115.5
C12—C13—H13A	119.4	C27A—O2—H2OA	109.4
C13—C14—C15	117.8 (2)	O2i—O2—H2OB	54.0
C13—C14—C17	121.4 (2)	C27B—O2—H2OB	108.9
C15—C14—C17	120.7 (2)	C27A—O2—H2OB	110.6
C16—C15—C14	120.9 (2)	H2OA—O2—H2OB	62.8
C16—C15—H15A	119.5	C27Ai—C27A—O2	83.1 (7)
C14—C15—H15A	119.5	C27Ai—C27A—H27A	52.0
C11—C16—C15	121.21 (19)	O2—C27A—H27A	109.7
C11—C16—H16A	119.4	C27Ai—C27A—H27B	161.2
C15—C16—H16A	119.4	O2—C27A—H27B	109.1
C14—C17—C18	114.54 (18)	H27A—C27A—H27B	109.5
C14—C17—H17A	108.6	C27Ai—C27A—H27C	78.2
C18—C17—H17A	108.6	O2—C27A—H27C	109.6
C14—C17—H17B	108.6	H27A—C27A—H27C	109.5
C18—C17—H17B	108.6	H27B—C27A—H27C	109.5
H17A—C17—H17B	107.6	O2—C27B—H27D	109.8
C20—C18—C19	110.73 (18)	O2—C27B—H27E	109.7
C20—C18—C17	111.82 (18)	H27D—C27B—H27E	109.5
C19—C18—C17	109.78 (18)	O2—C27B—H27F	108.9
C20—C18—H18A	108.1	H27D—C27B—H27F	109.5
C19—C18—H18A	108.1	H27E—C27B—H27F	109.4
C17—C18—H18A	108.1
C7—N1—N2—C9	−165.16 (18)	N2—C9—C10—C21	−143.00 (19)
C7—N1—N2—C8	21.2 (3)	C9—C10—C11—C12	92.1 (2)
C8—N3—N4—C9	0.2 (2)	C21—C10—C11—C12	−31.6 (3)
C22—N3—N4—C9	−179.21 (16)	C9—C10—C11—C16	−88.2 (2)
C6—C1—C2—C3	−0.8 (3)	C21—C10—C11—C16	148.00 (19)
C1—C2—C3—F1	179.92 (19)	C16—C11—C12—C13	0.1 (3)
C1—C2—C3—C4	0.5 (3)	C10—C11—C12—C13	179.68 (19)
F1—C3—C4—C5	−178.78 (19)	C11—C12—C13—C14	0.9 (3)
C2—C3—C4—C5	0.7 (3)	C12—C13—C14—C15	−1.3 (3)
C3—C4—C5—C6	−1.5 (3)	C12—C13—C14—C17	−179.2 (2)
C4—C5—C6—C1	1.2 (3)	C13—C14—C15—C16	0.6 (3)
C4—C5—C6—C7	178.98 (19)	C17—C14—C15—C16	178.64 (19)
C2—C1—C6—C5	0.0 (3)	C12—C11—C16—C15	−0.7 (3)
C2—C1—C6—C7	−177.7 (2)	C10—C11—C16—C15	179.70 (18)
N2—N1—C7—C6	176.41 (16)	C14—C15—C16—C11	0.3 (3)
C5—C6—C7—N1	176.71 (19)	C13—C14—C17—C18	101.5 (2)
C1—C6—C7—N1	−5.5 (3)	C15—C14—C17—C18	−76.4 (3)
N4—N3—C8—N2	−1.5 (2)	C14—C17—C18—C20	−60.0 (3)
C22—N3—C8—N2	177.79 (17)	C14—C17—C18—C19	176.70 (19)
N4—N3—C8—S1	175.59 (14)	C23—N5—C22—N3	−57.1 (2)
C22—N3—C8—S1	−5.1 (3)	C26—N5—C22—N3	73.4 (2)
C9—N2—C8—N3	2.3 (2)	C8—N3—C22—N5	109.5 (2)
N1—N2—C8—N3	176.42 (18)	N4—N3—C22—N5	−71.3 (2)
C9—N2—C8—S1	−174.70 (16)	C22—N5—C23—C24	−171.03 (17)
N1—N2—C8—S1	−0.6 (3)	C26—N5—C23—C24	56.2 (2)
N3—N4—C9—N2	1.3 (2)	C25—O1—C24—C23	59.4 (2)
N3—N4—C9—C10	−178.07 (17)	N5—C23—C24—O1	−56.9 (2)
C8—N2—C9—N4	−2.4 (2)	C24—O1—C25—C26	−60.8 (2)
N1—N2—C9—N4	−177.45 (16)	C22—N5—C26—C25	170.28 (17)
C8—N2—C9—C10	177.03 (17)	C23—N5—C26—C25	−57.4 (2)
N1—N2—C9—C10	2.0 (3)	O1—C25—C26—N5	59.8 (2)
N4—C9—C10—C11	−89.9 (2)	O2i—O2—C27A—C27Ai	41.1 (11)
N2—C9—C10—C11	90.7 (2)	C27B—O2—C27A—C27Ai	133.9 (10)
N4—C9—C10—C21	36.3 (3)

Cg1 is the centroid of the 1,2,4-triazole ring (N2/C8/N3/N4/C9).

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···S1	0.93	2.51	3.221 (2)	133
C22—H22A···Cg1ii	0.97	2.64	3.492 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the 1,2,4-triazole ring (N2/C8/N3/N4/C9).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯S1	0.93	2.51	3.221 (2)	133
C22—H22A⋯Cg1i	0.97	2.64	3.492 (2)	146

Symmetry code: (i) .