Crystal structure of 4-({(1E,2E)-3-[3-(4-fluoro­phen­yl)-1-isopropyl-1H-indol-2-yl]allyl­idene}amino)-1H-1,2,4-triazole-5(4H)-thione

Kulkarni, A.D.; Rahman, M.L.; Mohd. Yusoff, M.; Kwong, H.C.; Quah, C.K.

doi:10.1107/S205698901502201X

Crystal structure of 4-({(1E,2E)-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]allylidene}amino)-1H-1,2,4-triazole-5(4H)-thione

A. D. Kulkarni, M. L. Rahman, M. Mohd. Yusoff, H. C. Kwong and C. K. Quah

The asymmetric unit of the title compound comprises two independent molecules which exist in the trans conformation with respect to the methene C= C and the acyclic N=C bonds. In the crystal, molecules are linked via N—H

N hydrogen bonds, forming chains along the b-axis direction.

Keywords: crystal structure; 1,2,4-triazole-3-thione; indole; Schiff base; N—H

N hydrogen bonds; C—H

π interactions; π–π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901502201X/su5237sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S205698901502201X/su5237Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901502201X/su5237Isup3.cml Supplementary material

CCDC reference: 1437565

checkCIF report

Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.003 Å
R factor = 0.053
wR factor = 0.135
Data-to-parameter ratio = 22.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................     Please Do !
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C17A   -C22A          1.37 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.015 Check

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.66 mm
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         12 Note
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C22 H20 F N5 S
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         89 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXL2013 (Sheldrick, 2015) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

4-({(1E,2E)-3-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]allylidene}amino)-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₂₂H₂₀FN₅S	Z = 4
M_r = 405.49	F(000) = 848
Triclinic, P1	D_x = 1.315 Mg m⁻³
a = 9.9283 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5343 (5) Å	Cell parameters from 9367 reflections
c = 18.4694 (7) Å	θ = 2.3–27.8°
α = 99.8886 (13)°	µ = 0.19 mm⁻¹
β = 94.9582 (14)°	T = 297 K
γ = 98.4315 (14)°	Block, yellow
V = 2047.54 (14) Å³	0.66 × 0.60 × 0.46 mm

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	12002 independent reflections
Radiation source: fine-focus sealed tube	7987 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
φ and ω scans	θ_max = 30.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→14
T_min = 0.730, T_max = 0.830	k = −16→16
78666 measured reflections	l = −26→26

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0463P)² + 1.0061P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
12002 reflections	Δρ_max = 0.32 e Å⁻³
535 parameters	Δρ_min = −0.35 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1A	0.08455 (7)	0.69136 (4)	0.16534 (3)	0.05868 (16)
F1A	−0.31446 (17)	0.78739 (11)	0.47019 (10)	0.0905 (5)
N1A	−0.10366 (15)	0.16736 (12)	0.33308 (8)	0.0362 (3)
N2A	0.09099 (16)	0.39301 (12)	0.11449 (8)	0.0380 (3)
N3A	0.12047 (15)	0.48279 (12)	0.07369 (8)	0.0365 (3)
N4A	0.18107 (18)	0.64187 (14)	0.03380 (9)	0.0465 (4)
H4AB	0.204 (2)	0.719 (2)	0.0296 (13)	0.073 (7)*
N5A	0.20935 (18)	0.55200 (14)	−0.01880 (9)	0.0480 (4)
C1A	−0.13898 (18)	0.14893 (14)	0.40148 (9)	0.0362 (4)
C2A	−0.1351 (2)	0.05110 (16)	0.43631 (10)	0.0456 (4)
H2AA	−0.1068	−0.0177	0.4130	0.055*
C3A	−0.1746 (2)	0.05986 (18)	0.50619 (11)	0.0523 (5)
H3AA	−0.1719	−0.0042	0.5304	0.063*
C4A	−0.2188 (2)	0.16190 (18)	0.54209 (11)	0.0514 (5)
H4AA	−0.2443	0.1647	0.5895	0.062*
C5A	−0.22476 (19)	0.25805 (16)	0.50808 (10)	0.0437 (4)
H5AA	−0.2552	0.3256	0.5317	0.052*
C6A	−0.18407 (17)	0.25233 (14)	0.43690 (9)	0.0347 (3)
C7A	−0.17501 (16)	0.33564 (14)	0.38866 (9)	0.0332 (3)
C8A	−0.12480 (17)	0.28220 (14)	0.32566 (9)	0.0327 (3)
C9A	−0.09289 (17)	0.34389 (14)	0.26649 (9)	0.0353 (3)
H9AA	−0.1367	0.4096	0.2654	0.042*
C10A	−0.01208 (18)	0.32505 (14)	0.21247 (9)	0.0370 (4)
H10A	0.0286	0.2569	0.2059	0.044*
C11A	0.01137 (18)	0.40985 (14)	0.16505 (9)	0.0362 (4)
H11A	−0.0310	0.4771	0.1708	0.043*
C12A	0.12757 (19)	0.60532 (15)	0.09206 (10)	0.0389 (4)
C13A	0.17236 (19)	0.45754 (16)	0.00762 (10)	0.0423 (4)
H13A	0.1800	0.3809	−0.0155	0.051*
C14A	−0.07844 (19)	0.07247 (14)	0.27346 (10)	0.0394 (4)
H14A	−0.0741	0.1071	0.2287	0.047*
C15A	0.0590 (2)	0.0347 (2)	0.28984 (13)	0.0601 (6)
H15A	0.0701	−0.0299	0.2517	0.090*
H15B	0.0631	0.0092	0.3367	0.090*
H15C	0.1309	0.1009	0.2916	0.090*
C16A	−0.1958 (2)	−0.03206 (18)	0.25663 (12)	0.0545 (5)
H16A	−0.1871	−0.0821	0.2106	0.082*
H16B	−0.2813	−0.0028	0.2531	0.082*
H16C	−0.1931	−0.0774	0.2956	0.082*
C17A	−0.21013 (17)	0.45672 (14)	0.40646 (9)	0.0349 (3)
C18A	−0.34346 (19)	0.47005 (16)	0.41822 (11)	0.0434 (4)
H18A	−0.4101	0.4025	0.4124	0.052*
C19A	−0.3798 (2)	0.58122 (18)	0.43839 (12)	0.0517 (5)
H19A	−0.4699	0.5893	0.4453	0.062*
C20A	−0.2803 (2)	0.67830 (17)	0.44782 (12)	0.0550 (5)
C21A	−0.1487 (2)	0.67053 (18)	0.43688 (15)	0.0667 (6)
H21A	−0.0829	0.7389	0.4434	0.080*
C22A	−0.1138 (2)	0.55868 (17)	0.41574 (13)	0.0550 (5)
H22A	−0.0238	0.5523	0.4077	0.066*
S1B	0.68905 (7)	0.83235 (5)	0.03129 (3)	0.06422 (17)
F1B	0.46558 (19)	0.78643 (12)	0.34049 (10)	0.0933 (5)
N1B	0.49537 (16)	1.38803 (13)	0.20432 (8)	0.0401 (3)
N2B	0.75225 (17)	1.11714 (12)	−0.00035 (8)	0.0452 (4)
N3B	0.81061 (17)	1.01944 (12)	−0.03051 (8)	0.0432 (4)
N4B	0.8607 (2)	0.85069 (15)	−0.07253 (10)	0.0563 (5)
H4BB	0.866 (3)	0.773 (2)	−0.0831 (14)	0.080 (8)*
N5B	0.9290 (2)	0.92793 (15)	−0.11091 (10)	0.0652 (5)
C1B	0.40567 (18)	1.41730 (15)	0.25539 (9)	0.0383 (4)
C2B	0.3447 (2)	1.51889 (16)	0.27086 (10)	0.0454 (4)
H2BA	0.3608	1.5806	0.2447	0.054*
C3B	0.2599 (2)	1.52490 (18)	0.32609 (11)	0.0500 (5)
H3BA	0.2178	1.5917	0.3370	0.060*
C4B	0.23559 (19)	1.43340 (18)	0.36616 (11)	0.0480 (5)
H4BA	0.1802	1.4413	0.4042	0.058*
C5B	0.29213 (18)	1.33217 (17)	0.35015 (10)	0.0424 (4)
H5BA	0.2738	1.2706	0.3763	0.051*
C6B	0.37813 (17)	1.32248 (15)	0.29381 (9)	0.0368 (4)
C7B	0.45102 (17)	1.23172 (15)	0.26345 (9)	0.0365 (4)
C8B	0.52169 (18)	1.27408 (15)	0.20931 (9)	0.0373 (4)
C9B	0.60246 (18)	1.20425 (15)	0.16399 (10)	0.0391 (4)
H9BA	0.6333	1.1443	0.1855	0.047*
C10B	0.6420 (2)	1.20839 (15)	0.09709 (10)	0.0420 (4)
H10B	0.6236	1.2692	0.0725	0.050*
C11B	0.71322 (19)	1.11722 (15)	0.06399 (10)	0.0408 (4)
H11B	0.7314	1.0574	0.0895	0.049*
C12B	0.7857 (2)	0.90104 (15)	−0.02282 (10)	0.0437 (4)
C13B	0.8952 (3)	1.02883 (18)	−0.08422 (12)	0.0575 (6)
H13B	0.9251	1.0998	−0.0998	0.069*
C14B	0.5777 (2)	1.47295 (16)	0.16779 (10)	0.0432 (4)
H14B	0.6475	1.4314	0.1454	0.052*
C15B	0.4908 (3)	1.5060 (2)	0.10514 (12)	0.0648 (6)
H15D	0.5475	1.5581	0.0805	0.097*
H15E	0.4198	1.5459	0.1248	0.097*
H15F	0.4503	1.4350	0.0705	0.097*
C16B	0.6536 (2)	1.58146 (18)	0.22234 (13)	0.0576 (5)
H16D	0.7206	1.6251	0.1983	0.086*
H16E	0.6987	1.5561	0.2636	0.086*
H16F	0.5896	1.6318	0.2396	0.086*
C17B	0.45015 (17)	1.11375 (15)	0.28393 (10)	0.0381 (4)
C18B	0.4860 (2)	1.10356 (16)	0.35652 (11)	0.0457 (4)
H18B	0.5065	1.1721	0.3929	0.055*
C19B	0.4921 (2)	0.99369 (19)	0.37605 (13)	0.0559 (5)
H19B	0.5177	0.9876	0.4247	0.067*
C20B	0.4592 (2)	0.89457 (17)	0.32175 (15)	0.0586 (6)
C21B	0.4200 (2)	0.89917 (18)	0.25037 (14)	0.0615 (6)
H21B	0.3967	0.8296	0.2149	0.074*
C22B	0.4154 (2)	1.00955 (17)	0.23120 (12)	0.0504 (5)
H22B	0.3887	1.0140	0.1824	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0947 (4)	0.0325 (2)	0.0520 (3)	0.0121 (2)	0.0265 (3)	0.0061 (2)
F1A	0.0981 (11)	0.0402 (7)	0.1313 (14)	0.0313 (7)	0.0106 (10)	−0.0051 (8)
N1A	0.0483 (8)	0.0295 (7)	0.0346 (7)	0.0111 (6)	0.0152 (6)	0.0072 (5)
N2A	0.0550 (9)	0.0260 (6)	0.0376 (7)	0.0088 (6)	0.0146 (7)	0.0121 (6)
N3A	0.0479 (8)	0.0286 (7)	0.0376 (7)	0.0096 (6)	0.0131 (6)	0.0114 (6)
N4A	0.0640 (10)	0.0333 (8)	0.0484 (9)	0.0096 (7)	0.0189 (8)	0.0175 (7)
N5A	0.0635 (10)	0.0417 (8)	0.0469 (9)	0.0156 (7)	0.0223 (8)	0.0166 (7)
C1A	0.0429 (9)	0.0326 (8)	0.0347 (8)	0.0064 (7)	0.0105 (7)	0.0074 (6)
C2A	0.0606 (12)	0.0351 (9)	0.0444 (10)	0.0101 (8)	0.0125 (9)	0.0112 (7)
C3A	0.0697 (13)	0.0430 (10)	0.0476 (11)	0.0036 (9)	0.0131 (10)	0.0193 (9)
C4A	0.0645 (13)	0.0532 (11)	0.0378 (10)	0.0021 (10)	0.0180 (9)	0.0124 (8)
C5A	0.0506 (11)	0.0411 (9)	0.0385 (9)	0.0034 (8)	0.0164 (8)	0.0028 (7)
C6A	0.0374 (8)	0.0314 (8)	0.0348 (8)	0.0031 (6)	0.0095 (7)	0.0042 (6)
C7A	0.0347 (8)	0.0297 (7)	0.0358 (8)	0.0052 (6)	0.0096 (7)	0.0048 (6)
C8A	0.0368 (8)	0.0282 (7)	0.0348 (8)	0.0066 (6)	0.0088 (7)	0.0071 (6)
C9A	0.0427 (9)	0.0286 (7)	0.0371 (9)	0.0088 (7)	0.0087 (7)	0.0082 (6)
C10A	0.0492 (10)	0.0281 (8)	0.0371 (9)	0.0092 (7)	0.0111 (7)	0.0094 (6)
C11A	0.0440 (9)	0.0293 (8)	0.0379 (9)	0.0084 (7)	0.0091 (7)	0.0092 (6)
C12A	0.0477 (10)	0.0298 (8)	0.0430 (9)	0.0088 (7)	0.0094 (8)	0.0127 (7)
C13A	0.0536 (11)	0.0370 (9)	0.0423 (10)	0.0131 (8)	0.0180 (8)	0.0126 (7)
C14A	0.0531 (10)	0.0301 (8)	0.0365 (9)	0.0092 (7)	0.0146 (8)	0.0038 (7)
C15A	0.0558 (12)	0.0563 (12)	0.0698 (14)	0.0210 (10)	0.0184 (11)	0.0006 (10)
C16A	0.0670 (13)	0.0414 (10)	0.0508 (11)	0.0011 (9)	0.0041 (10)	0.0046 (9)
C17A	0.0406 (9)	0.0300 (8)	0.0343 (8)	0.0070 (7)	0.0084 (7)	0.0041 (6)
C18A	0.0397 (9)	0.0354 (9)	0.0527 (11)	0.0045 (7)	0.0058 (8)	0.0024 (8)
C19A	0.0455 (11)	0.0490 (11)	0.0618 (13)	0.0183 (9)	0.0090 (9)	0.0032 (9)
C20A	0.0655 (13)	0.0330 (9)	0.0664 (13)	0.0190 (9)	0.0055 (11)	0.0010 (9)
C21A	0.0585 (13)	0.0295 (9)	0.107 (2)	0.0000 (9)	0.0110 (13)	0.0033 (11)
C22A	0.0391 (10)	0.0373 (10)	0.0883 (16)	0.0051 (8)	0.0153 (10)	0.0083 (10)
S1B	0.0919 (4)	0.0371 (3)	0.0697 (4)	0.0092 (3)	0.0418 (3)	0.0115 (2)
F1B	0.1249 (13)	0.0413 (7)	0.1258 (14)	0.0180 (8)	0.0379 (11)	0.0337 (8)
N1B	0.0509 (9)	0.0360 (7)	0.0381 (8)	0.0176 (6)	0.0147 (7)	0.0067 (6)
N2B	0.0683 (10)	0.0299 (7)	0.0451 (8)	0.0209 (7)	0.0244 (8)	0.0081 (6)
N3B	0.0665 (10)	0.0301 (7)	0.0410 (8)	0.0192 (7)	0.0242 (7)	0.0100 (6)
N4B	0.0911 (14)	0.0338 (8)	0.0544 (10)	0.0246 (9)	0.0361 (9)	0.0113 (7)
N5B	0.1056 (15)	0.0434 (9)	0.0627 (11)	0.0304 (10)	0.0506 (11)	0.0185 (8)
C1B	0.0421 (9)	0.0383 (9)	0.0343 (8)	0.0118 (7)	0.0076 (7)	0.0003 (7)
C2B	0.0550 (11)	0.0393 (9)	0.0434 (10)	0.0172 (8)	0.0089 (8)	0.0027 (8)
C3B	0.0521 (11)	0.0485 (11)	0.0484 (11)	0.0216 (9)	0.0076 (9)	−0.0057 (9)
C4B	0.0422 (10)	0.0556 (11)	0.0439 (10)	0.0119 (8)	0.0127 (8)	−0.0043 (9)
C5B	0.0403 (9)	0.0449 (10)	0.0403 (9)	0.0066 (8)	0.0089 (7)	0.0012 (8)
C6B	0.0365 (9)	0.0371 (8)	0.0348 (8)	0.0073 (7)	0.0051 (7)	−0.0004 (7)
C7B	0.0396 (9)	0.0344 (8)	0.0350 (8)	0.0086 (7)	0.0070 (7)	0.0017 (7)
C8B	0.0432 (9)	0.0342 (8)	0.0370 (9)	0.0133 (7)	0.0101 (7)	0.0049 (7)
C9B	0.0471 (10)	0.0335 (8)	0.0397 (9)	0.0144 (7)	0.0114 (8)	0.0050 (7)
C10B	0.0567 (11)	0.0332 (8)	0.0405 (9)	0.0178 (8)	0.0150 (8)	0.0059 (7)
C11B	0.0548 (11)	0.0313 (8)	0.0401 (9)	0.0142 (7)	0.0143 (8)	0.0073 (7)
C12B	0.0632 (12)	0.0309 (8)	0.0409 (9)	0.0150 (8)	0.0161 (8)	0.0062 (7)
C13B	0.0915 (16)	0.0388 (10)	0.0548 (12)	0.0238 (10)	0.0413 (11)	0.0166 (9)
C14B	0.0551 (11)	0.0391 (9)	0.0408 (9)	0.0166 (8)	0.0158 (8)	0.0096 (7)
C15B	0.0834 (16)	0.0719 (15)	0.0486 (12)	0.0267 (13)	0.0121 (11)	0.0237 (11)
C16B	0.0616 (13)	0.0447 (11)	0.0674 (14)	0.0100 (9)	0.0150 (11)	0.0081 (10)
C17B	0.0349 (8)	0.0329 (8)	0.0461 (10)	0.0047 (7)	0.0108 (7)	0.0037 (7)
C18B	0.0521 (11)	0.0359 (9)	0.0477 (10)	0.0006 (8)	0.0119 (8)	0.0062 (8)
C19B	0.0648 (13)	0.0498 (11)	0.0580 (12)	0.0071 (10)	0.0150 (10)	0.0215 (10)
C20B	0.0613 (13)	0.0345 (10)	0.0853 (17)	0.0063 (9)	0.0265 (12)	0.0185 (10)
C21B	0.0618 (13)	0.0336 (10)	0.0814 (17)	−0.0006 (9)	0.0130 (12)	−0.0057 (10)
C22B	0.0521 (11)	0.0423 (10)	0.0519 (11)	0.0050 (8)	0.0039 (9)	−0.0015 (8)

Geometric parameters (Å, º) top

S1A—C12A	1.6621 (18)	S1B—C12B	1.6618 (19)
F1A—C20A	1.356 (2)	F1B—C20B	1.359 (2)
N1A—C1A	1.382 (2)	N1B—C1B	1.386 (2)
N1A—C8A	1.399 (2)	N1B—C8B	1.394 (2)
N1A—C14A	1.479 (2)	N1B—C14B	1.473 (2)
N2A—C11A	1.283 (2)	N2B—C11B	1.281 (2)
N2A—N3A	1.3940 (18)	N2B—N3B	1.3955 (18)
N3A—C13A	1.368 (2)	N3B—C13B	1.362 (2)
N3A—C12A	1.385 (2)	N3B—C12B	1.386 (2)
N4A—C12A	1.344 (2)	N4B—C12B	1.341 (2)
N4A—N5A	1.372 (2)	N4B—N5B	1.371 (2)
N4A—H4AB	0.91 (3)	N4B—H4BB	0.90 (3)
N5A—C13A	1.287 (2)	N5B—C13B	1.287 (2)
C1A—C2A	1.395 (2)	C1B—C2B	1.394 (2)
C1A—C6A	1.411 (2)	C1B—C6B	1.409 (2)
C2A—C3A	1.373 (3)	C2B—C3B	1.377 (3)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.396 (3)	C3B—C4B	1.394 (3)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.371 (3)	C4B—C5B	1.367 (3)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.402 (2)	C5B—C6B	1.402 (2)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.417 (2)	C6B—C7B	1.423 (2)
C7A—C8A	1.388 (2)	C7B—C8B	1.385 (2)
C7A—C17A	1.478 (2)	C7B—C17B	1.473 (2)
C8A—C9A	1.436 (2)	C8B—C9B	1.437 (2)
C9A—C10A	1.342 (2)	C9B—C10B	1.335 (2)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C11A	1.429 (2)	C10B—C11B	1.432 (2)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—H11A	0.9300	C11B—H11B	0.9300
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.514 (3)	C14B—C15B	1.518 (3)
C14A—C16A	1.518 (3)	C14B—C16B	1.520 (3)
C14A—H14A	0.9800	C14B—H14B	0.9800
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C16A—H16A	0.9600	C16B—H16D	0.9600
C16A—H16B	0.9600	C16B—H16E	0.9600
C16A—H16C	0.9600	C16B—H16F	0.9600
C17A—C22A	1.379 (2)	C17B—C18B	1.386 (3)
C17A—C18A	1.386 (2)	C17B—C22B	1.389 (2)
C18A—C19A	1.381 (2)	C18B—C19B	1.384 (3)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.356 (3)	C19B—C20B	1.364 (3)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—C21A	1.353 (3)	C20B—C21B	1.354 (3)
C21A—C22A	1.385 (3)	C21B—C22B	1.385 (3)
C21A—H21A	0.9300	C21B—H21B	0.9300
C22A—H22A	0.9300	C22B—H22B	0.9300

C1A—N1A—C8A	107.86 (13)	C1B—N1B—C8B	107.49 (14)
C1A—N1A—C14A	124.51 (13)	C1B—N1B—C14B	125.46 (14)
C8A—N1A—C14A	126.36 (13)	C8B—N1B—C14B	124.92 (14)
C11A—N2A—N3A	117.96 (13)	C11B—N2B—N3B	116.57 (14)
C13A—N3A—C12A	108.07 (14)	C13B—N3B—C12B	108.25 (14)
C13A—N3A—N2A	119.78 (13)	C13B—N3B—N2B	120.17 (14)
C12A—N3A—N2A	131.35 (14)	C12B—N3B—N2B	131.03 (15)
C12A—N4A—N5A	114.68 (15)	C12B—N4B—N5B	114.71 (15)
C12A—N4A—H4AB	124.6 (16)	C12B—N4B—H4BB	125.5 (17)
N5A—N4A—H4AB	120.5 (16)	N5B—N4B—H4BB	119.8 (17)
C13A—N5A—N4A	103.21 (14)	C13B—N5B—N4B	103.27 (15)
N1A—C1A—C2A	131.02 (15)	N1B—C1B—C2B	130.38 (17)
N1A—C1A—C6A	108.27 (14)	N1B—C1B—C6B	108.73 (14)
C2A—C1A—C6A	120.71 (15)	C2B—C1B—C6B	120.88 (16)
C3A—C2A—C1A	117.77 (17)	C3B—C2B—C1B	117.91 (18)
C3A—C2A—H2AA	121.1	C3B—C2B—H2BA	121.0
C1A—C2A—H2AA	121.1	C1B—C2B—H2BA	121.0
C2A—C3A—C4A	122.14 (18)	C2B—C3B—C4B	121.70 (17)
C2A—C3A—H3AA	118.9	C2B—C3B—H3BA	119.1
C4A—C3A—H3AA	118.9	C4B—C3B—H3BA	119.1
C5A—C4A—C3A	120.66 (17)	C5B—C4B—C3B	120.80 (17)
C5A—C4A—H4AA	119.7	C5B—C4B—H4BA	119.6
C3A—C4A—H4AA	119.7	C3B—C4B—H4BA	119.6
C4A—C5A—C6A	118.62 (17)	C4B—C5B—C6B	119.06 (18)
C4A—C5A—H5AA	120.7	C4B—C5B—H5BA	120.5
C6A—C5A—H5AA	120.7	C6B—C5B—H5BA	120.5
C5A—C6A—C1A	120.09 (15)	C5B—C6B—C1B	119.59 (15)
C5A—C6A—C7A	132.27 (15)	C5B—C6B—C7B	133.36 (17)
C1A—C6A—C7A	107.63 (14)	C1B—C6B—C7B	107.05 (14)
C8A—C7A—C6A	106.91 (14)	C8B—C7B—C6B	107.00 (15)
C8A—C7A—C17A	128.82 (14)	C8B—C7B—C17B	125.95 (15)
C6A—C7A—C17A	124.25 (14)	C6B—C7B—C17B	127.04 (15)
C7A—C8A—N1A	109.33 (13)	C7B—C8B—N1B	109.70 (14)
C7A—C8A—C9A	122.57 (14)	C7B—C8B—C9B	122.96 (15)
N1A—C8A—C9A	127.96 (14)	N1B—C8B—C9B	127.25 (15)
C10A—C9A—C8A	132.44 (15)	C10B—C9B—C8B	132.70 (16)
C10A—C9A—H9AA	113.8	C10B—C9B—H9BA	113.7
C8A—C9A—H9AA	113.8	C8B—C9B—H9BA	113.7
C9A—C10A—C11A	119.92 (15)	C9B—C10B—C11B	118.64 (16)
C9A—C10A—H10A	120.0	C9B—C10B—H10B	120.7
C11A—C10A—H10A	120.0	C11B—C10B—H10B	120.7
N2A—C11A—C10A	119.84 (15)	N2B—C11B—C10B	120.80 (16)
N2A—C11A—H11A	120.1	N2B—C11B—H11B	119.6
C10A—C11A—H11A	120.1	C10B—C11B—H11B	119.6
N4A—C12A—N3A	101.82 (14)	N4B—C12B—N3B	101.69 (15)
N4A—C12A—S1A	126.62 (13)	N4B—C12B—S1B	126.76 (14)
N3A—C12A—S1A	131.56 (13)	N3B—C12B—S1B	131.55 (13)
N5A—C13A—N3A	112.20 (16)	N5B—C13B—N3B	112.06 (17)
N5A—C13A—H13A	123.9	N5B—C13B—H13B	124.0
N3A—C13A—H13A	123.9	N3B—C13B—H13B	124.0
N1A—C14A—C15A	111.43 (16)	N1B—C14B—C15B	110.91 (17)
N1A—C14A—C16A	111.89 (15)	N1B—C14B—C16B	112.39 (15)
C15A—C14A—C16A	112.67 (16)	C15B—C14B—C16B	112.68 (17)
N1A—C14A—H14A	106.8	N1B—C14B—H14B	106.8
C15A—C14A—H14A	106.8	C15B—C14B—H14B	106.8
C16A—C14A—H14A	106.8	C16B—C14B—H14B	106.8
C14A—C15A—H15A	109.5	C14B—C15B—H15D	109.5
C14A—C15A—H15B	109.5	C14B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C14A—C15A—H15C	109.5	C14B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C14A—C16A—H16A	109.5	C14B—C16B—H16D	109.5
C14A—C16A—H16B	109.5	C14B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C14A—C16A—H16C	109.5	C14B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
C22A—C17A—C18A	117.71 (16)	C18B—C17B—C22B	117.97 (17)
C22A—C17A—C7A	122.67 (15)	C18B—C17B—C7B	120.80 (15)
C18A—C17A—C7A	119.54 (15)	C22B—C17B—C7B	121.23 (17)
C19A—C18A—C17A	121.63 (17)	C19B—C18B—C17B	121.48 (18)
C19A—C18A—H18A	119.2	C19B—C18B—H18B	119.3
C17A—C18A—H18A	119.2	C17B—C18B—H18B	119.3
C20A—C19A—C18A	118.09 (18)	C20B—C19B—C18B	118.0 (2)
C20A—C19A—H19A	121.0	C20B—C19B—H19B	121.0
C18A—C19A—H19A	121.0	C18B—C19B—H19B	121.0
C21A—C20A—C19A	122.76 (18)	C21B—C20B—F1B	118.8 (2)
C21A—C20A—F1A	118.94 (19)	C21B—C20B—C19B	122.98 (19)
C19A—C20A—F1A	118.30 (19)	F1B—C20B—C19B	118.3 (2)
C20A—C21A—C22A	118.65 (19)	C20B—C21B—C22B	118.66 (19)
C20A—C21A—H21A	120.7	C20B—C21B—H21B	120.7
C22A—C21A—H21A	120.7	C22B—C21B—H21B	120.7
C17A—C22A—C21A	121.14 (18)	C21B—C22B—C17B	120.9 (2)
C17A—C22A—H22A	119.4	C21B—C22B—H22B	119.6
C21A—C22A—H22A	119.4	C17B—C22B—H22B	119.6

C11A—N2A—N3A—C13A	−162.30 (17)	C11B—N2B—N3B—C13B	−157.5 (2)
C11A—N2A—N3A—C12A	29.3 (3)	C11B—N2B—N3B—C12B	32.0 (3)
C12A—N4A—N5A—C13A	0.0 (2)	C12B—N4B—N5B—C13B	0.0 (3)
C8A—N1A—C1A—C2A	−178.94 (19)	C8B—N1B—C1B—C2B	−177.88 (19)
C14A—N1A—C1A—C2A	13.3 (3)	C14B—N1B—C1B—C2B	18.1 (3)
C8A—N1A—C1A—C6A	0.66 (19)	C8B—N1B—C1B—C6B	1.4 (2)
C14A—N1A—C1A—C6A	−167.09 (15)	C14B—N1B—C1B—C6B	−162.60 (16)
N1A—C1A—C2A—C3A	178.64 (19)	N1B—C1B—C2B—C3B	−179.10 (19)
C6A—C1A—C2A—C3A	−0.9 (3)	C6B—C1B—C2B—C3B	1.7 (3)
C1A—C2A—C3A—C4A	0.6 (3)	C1B—C2B—C3B—C4B	0.5 (3)
C2A—C3A—C4A—C5A	0.3 (3)	C2B—C3B—C4B—C5B	−2.1 (3)
C3A—C4A—C5A—C6A	−0.8 (3)	C3B—C4B—C5B—C6B	1.5 (3)
C4A—C5A—C6A—C1A	0.4 (3)	C4B—C5B—C6B—C1B	0.6 (3)
C4A—C5A—C6A—C7A	−178.17 (19)	C4B—C5B—C6B—C7B	−179.50 (19)
N1A—C1A—C6A—C5A	−179.20 (16)	N1B—C1B—C6B—C5B	178.37 (16)
C2A—C1A—C6A—C5A	0.4 (3)	C2B—C1B—C6B—C5B	−2.3 (3)
N1A—C1A—C6A—C7A	−0.31 (19)	N1B—C1B—C6B—C7B	−1.53 (19)
C2A—C1A—C6A—C7A	179.35 (17)	C2B—C1B—C6B—C7B	177.81 (17)
C5A—C6A—C7A—C8A	178.54 (19)	C5B—C6B—C7B—C8B	−178.80 (19)
C1A—C6A—C7A—C8A	−0.17 (19)	C1B—C6B—C7B—C8B	1.08 (19)
C5A—C6A—C7A—C17A	0.2 (3)	C5B—C6B—C7B—C17B	2.4 (3)
C1A—C6A—C7A—C17A	−178.53 (15)	C1B—C6B—C7B—C17B	−177.68 (17)
C6A—C7A—C8A—N1A	0.59 (19)	C6B—C7B—C8B—N1B	−0.3 (2)
C17A—C7A—C8A—N1A	178.84 (16)	C17B—C7B—C8B—N1B	178.53 (16)
C6A—C7A—C8A—C9A	−175.47 (16)	C6B—C7B—C8B—C9B	−177.13 (16)
C17A—C7A—C8A—C9A	2.8 (3)	C17B—C7B—C8B—C9B	1.7 (3)
C1A—N1A—C8A—C7A	−0.78 (19)	C1B—N1B—C8B—C7B	−0.7 (2)
C14A—N1A—C8A—C7A	166.68 (16)	C14B—N1B—C8B—C7B	163.39 (16)
C1A—N1A—C8A—C9A	175.00 (17)	C1B—N1B—C8B—C9B	176.01 (17)
C14A—N1A—C8A—C9A	−17.5 (3)	C14B—N1B—C8B—C9B	−19.9 (3)
C7A—C8A—C9A—C10A	158.93 (19)	C7B—C8B—C9B—C10B	155.7 (2)
N1A—C8A—C9A—C10A	−16.4 (3)	N1B—C8B—C9B—C10B	−20.6 (3)
C8A—C9A—C10A—C11A	−173.41 (18)	C8B—C9B—C10B—C11B	−174.33 (19)
N3A—N2A—C11A—C10A	−174.54 (15)	N3B—N2B—C11B—C10B	−174.83 (17)
C9A—C10A—C11A—N2A	178.49 (17)	C9B—C10B—C11B—N2B	179.52 (19)
N5A—N4A—C12A—N3A	−0.8 (2)	N5B—N4B—C12B—N3B	−0.6 (2)
N5A—N4A—C12A—S1A	178.96 (15)	N5B—N4B—C12B—S1B	178.81 (17)
C13A—N3A—C12A—N4A	1.21 (19)	C13B—N3B—C12B—N4B	1.0 (2)
N2A—N3A—C12A—N4A	170.61 (17)	N2B—N3B—C12B—N4B	172.32 (19)
C13A—N3A—C12A—S1A	−178.51 (16)	C13B—N3B—C12B—S1B	−178.40 (19)
N2A—N3A—C12A—S1A	−9.1 (3)	N2B—N3B—C12B—S1B	−7.1 (3)
N4A—N5A—C13A—N3A	0.8 (2)	N4B—N5B—C13B—N3B	0.7 (3)
C12A—N3A—C13A—N5A	−1.4 (2)	C12B—N3B—C13B—N5B	−1.1 (3)
N2A—N3A—C13A—N5A	−172.20 (16)	N2B—N3B—C13B—N5B	−173.56 (19)
C1A—N1A—C14A—C15A	−75.0 (2)	C1B—N1B—C14B—C15B	−78.5 (2)
C8A—N1A—C14A—C15A	119.51 (19)	C8B—N1B—C14B—C15B	120.25 (19)
C1A—N1A—C14A—C16A	52.1 (2)	C1B—N1B—C14B—C16B	48.7 (2)
C8A—N1A—C14A—C16A	−113.34 (19)	C8B—N1B—C14B—C16B	−112.61 (19)
C8A—C7A—C17A—C22A	−64.4 (3)	C8B—C7B—C17B—C18B	125.1 (2)
C6A—C7A—C17A—C22A	113.6 (2)	C6B—C7B—C17B—C18B	−56.4 (3)
C8A—C7A—C17A—C18A	119.0 (2)	C8B—C7B—C17B—C22B	−54.0 (3)
C6A—C7A—C17A—C18A	−63.0 (2)	C6B—C7B—C17B—C22B	124.5 (2)
C22A—C17A—C18A—C19A	0.2 (3)	C22B—C17B—C18B—C19B	2.2 (3)
C7A—C17A—C18A—C19A	176.91 (17)	C7B—C17B—C18B—C19B	−176.87 (18)
C17A—C18A—C19A—C20A	−1.1 (3)	C17B—C18B—C19B—C20B	−1.1 (3)
C18A—C19A—C20A—C21A	1.4 (4)	C18B—C19B—C20B—C21B	−0.7 (3)
C18A—C19A—C20A—F1A	−177.68 (19)	C18B—C19B—C20B—F1B	179.67 (19)
C19A—C20A—C21A—C22A	−0.5 (4)	F1B—C20B—C21B—C22B	−179.12 (19)
F1A—C20A—C21A—C22A	178.5 (2)	C19B—C20B—C21B—C22B	1.2 (3)
C18A—C17A—C22A—C21A	0.7 (3)	C20B—C21B—C22B—C17B	0.0 (3)
C7A—C17A—C22A—C21A	−176.0 (2)	C18B—C17B—C22B—C21B	−1.6 (3)
C20A—C21A—C22A—C17A	−0.5 (4)	C7B—C17B—C22B—C21B	177.44 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of ring N3A–N5A/C12A/C13A, Cg2 is the centroid of ring C17B–C22B, and Cg3 is the centroid of ring C1A–C6A.

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H4AB···N2Bⁱ	0.90 (2)	2.05 (2)	2.944 (2)	170 (2)
N4B—H4BB···N2Aⁱⁱ	0.89 (2)	2.02 (2)	2.906 (2)	170 (3)
C15B—H15E···Cg1ⁱⁱⁱ	0.96	2.91	3.521 (3)	123
C16A—H16B···Cg2^iv	0.96	2.87	3.716 (2)	148
C21A—H21A···Cg3^v	0.93	2.90	3.668 (2)	140

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z; (iii) x, y+1, z; (iv) x−1, y−1, z; (v) −x, −y+1, −z+1.

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Crystal structure of 4-({(1E,2E)-3-[3-(4-fluoro­phen­yl)-1-isopropyl-1H-indol-2-yl]allyl­idene}amino)-1H-1,2,4-triazole-5(4H)-thione

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Crystal structure of 4-({(1E,2E)-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]allylidene}amino)-1H-1,2,4-triazole-5(4H)-thione