Crystal structure of 4-({(1E,2E)-3-[3-(4-fluoro­phen­yl)-1-isopropyl-1H-indol-2-yl]allyl­idene}amino)-5-methyl-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/S2056989015020101

Crystal structure of 4-({(1E,2E)-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]allylidene}amino)-5-methyl-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 title compound exists in a trans conformation with respect to the methene C=C and the acyclic N=C bonds, with the 1,2,4-triazole-5(4H)-thione ring almost normal to the indole and benzene rings. In the crystal, molecules are linked by pairs of N—H

S hydrogen bonds, forming inversion dimers with an $R_{2}^{2}$ (8) ring motif.

Keywords: crystal structure; 1,2,4-triazole-5(4H)-thione; indole; Schiff base; N—H

S hydrogen bonds; C—H

π and π–π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015020101/su5226sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015020101/su5226Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015020101/su5226Isup3.cml Supplementary material

CCDC reference: 1433130

checkCIF report

Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.003 Å
R factor = 0.046
wR factor = 0.127
Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C15    --  C16     ..        7.0 su
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C15 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.320 Check

Alert level G
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         60 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
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 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)-5-methyl-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₂₃H₂₂FN₅S	F(000) = 880
M_r = 419.51	D_x = 1.286 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.4388 (8) Å	Cell parameters from 5835 reflections
b = 23.482 (3) Å	θ = 2.8–27.5°
c = 14.572 (3) Å	µ = 0.18 mm⁻¹
β = 100.5009 (19)°	T = 297 K
V = 2166.3 (6) Å³	Block, yellow
Z = 4	0.40 × 0.27 × 0.09 mm

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5094 independent reflections
Radiation source: fine-focus sealed tube	3393 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 27.8°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.779, T_max = 0.932	k = −30→30
24228 measured reflections	l = −19→18

Refinement top

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)] = 0.046	Hydrogen site location: mixed
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0559P)² + 0.3794P] where P = (F_o² + 2F_c²)/3
5094 reflections	(Δ/σ)_max = 0.001
278 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.19 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
S1	0.39854 (8)	0.40778 (2)	0.98203 (4)	0.06099 (17)
F1	0.5717 (2)	0.13276 (6)	1.27264 (9)	0.0912 (4)
N1	−0.3776 (2)	0.17803 (6)	0.86118 (10)	0.0523 (4)
N2	0.0328 (2)	0.36814 (6)	1.09831 (11)	0.0512 (4)
N3	0.0953 (2)	0.42497 (6)	1.09021 (10)	0.0464 (3)
N4	0.2694 (3)	0.49906 (7)	1.07257 (11)	0.0540 (4)
H4B	0.358 (3)	0.5255 (9)	1.0558 (15)	0.073 (7)*
N5	0.1315 (3)	0.51498 (7)	1.13047 (11)	0.0564 (4)
C1	−0.4000 (3)	0.12025 (8)	0.87117 (12)	0.0497 (4)
C2	−0.5378 (3)	0.08101 (9)	0.81951 (14)	0.0598 (5)
H2A	−0.6413	0.0929	0.7702	0.072*
C3	−0.5163 (3)	0.02485 (9)	0.84345 (15)	0.0655 (6)
H3A	−0.6061	−0.0017	0.8093	0.079*
C4	−0.3635 (3)	0.00615 (9)	0.91768 (15)	0.0636 (5)
H4A	−0.3509	−0.0325	0.9313	0.076*
C5	−0.2315 (3)	0.04425 (8)	0.97074 (14)	0.0547 (5)
H5A	−0.1318	0.0318	1.0211	0.066*
C6	−0.2489 (3)	0.10201 (7)	0.94809 (12)	0.0457 (4)
C7	−0.1334 (3)	0.15099 (7)	0.98611 (11)	0.0446 (4)
C8	−0.2146 (3)	0.19687 (8)	0.93150 (12)	0.0474 (4)
C9	−0.1544 (3)	0.25633 (8)	0.93989 (13)	0.0529 (4)
H9A	−0.1696	0.2772	0.8848	0.063*
C10	−0.0801 (3)	0.28383 (8)	1.01813 (13)	0.0503 (4)
H10A	−0.0641	0.2640	1.0743	0.060*
C11	−0.0232 (3)	0.34278 (8)	1.02010 (13)	0.0498 (4)
H11A	−0.0270	0.3626	0.9646	0.060*
C12	0.2548 (3)	0.44453 (8)	1.04702 (12)	0.0478 (4)
C13	0.0300 (3)	0.46845 (8)	1.14103 (13)	0.0507 (4)
C14	−0.1374 (3)	0.46154 (10)	1.19744 (16)	0.0702 (6)
H14A	−0.2661	0.4498	1.1578	0.105*
H14B	−0.1598	0.4971	1.2265	0.105*
H14C	−0.0951	0.4332	1.2446	0.105*
C15	−0.4963 (3)	0.21375 (9)	0.78577 (13)	0.0592 (5)
H15A	−0.4358	0.2520	0.7967	0.071*
C16	−0.7234 (4)	0.22020 (12)	0.79263 (17)	0.0881 (8)
H16A	−0.7933	0.2432	0.7418	0.132*
H16B	−0.7342	0.2382	0.8508	0.132*
H16C	−0.7888	0.1833	0.7897	0.132*
C17	−0.4518 (4)	0.19635 (11)	0.69253 (15)	0.0850 (7)
H17A	−0.5220	0.2219	0.6456	0.127*
H17B	−0.5024	0.1583	0.6785	0.127*
H17C	−0.3023	0.1976	0.6937	0.127*
C18	0.0509 (3)	0.14878 (7)	1.06333 (12)	0.0446 (4)
C19	0.0324 (3)	0.12700 (8)	1.15036 (13)	0.0536 (5)
H19A	−0.0996	0.1158	1.1611	0.064*
C20	0.2057 (3)	0.12172 (9)	1.22087 (14)	0.0604 (5)
H20A	0.1915	0.1075	1.2789	0.072*
C21	0.3980 (3)	0.13781 (9)	1.20369 (14)	0.0602 (5)
C22	0.4252 (3)	0.15878 (9)	1.11945 (15)	0.0624 (5)
H22A	0.5585	0.1693	1.1094	0.075*
C23	0.2508 (3)	0.16406 (8)	1.04971 (13)	0.0548 (5)
H23A	0.2676	0.1783	0.9919	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0679 (3)	0.0568 (3)	0.0619 (3)	−0.0073 (2)	0.0215 (3)	−0.0065 (2)
F1	0.0731 (8)	0.1057 (11)	0.0794 (9)	0.0101 (7)	−0.0271 (7)	0.0028 (8)
N1	0.0596 (9)	0.0492 (9)	0.0423 (8)	0.0011 (7)	−0.0065 (7)	0.0004 (7)
N2	0.0588 (9)	0.0437 (8)	0.0510 (9)	−0.0046 (7)	0.0099 (7)	−0.0012 (7)
N3	0.0505 (8)	0.0427 (8)	0.0439 (8)	−0.0035 (6)	0.0032 (7)	−0.0005 (6)
N4	0.0575 (9)	0.0487 (9)	0.0558 (10)	−0.0077 (8)	0.0106 (8)	−0.0006 (7)
N5	0.0577 (9)	0.0509 (9)	0.0594 (10)	−0.0023 (8)	0.0073 (8)	−0.0055 (8)
C1	0.0537 (10)	0.0520 (11)	0.0423 (10)	−0.0005 (8)	0.0059 (8)	−0.0043 (8)
C2	0.0636 (12)	0.0635 (13)	0.0485 (11)	−0.0081 (10)	0.0005 (9)	−0.0069 (9)
C3	0.0713 (13)	0.0632 (13)	0.0612 (13)	−0.0189 (11)	0.0100 (11)	−0.0146 (10)
C4	0.0787 (14)	0.0463 (11)	0.0681 (13)	−0.0077 (10)	0.0197 (12)	−0.0062 (10)
C5	0.0589 (11)	0.0493 (11)	0.0564 (11)	0.0029 (9)	0.0121 (9)	0.0011 (9)
C6	0.0490 (10)	0.0459 (10)	0.0424 (9)	0.0021 (8)	0.0091 (8)	−0.0026 (8)
C7	0.0495 (10)	0.0432 (9)	0.0402 (9)	0.0031 (8)	0.0061 (8)	−0.0008 (7)
C8	0.0523 (10)	0.0471 (10)	0.0407 (9)	0.0010 (8)	0.0023 (8)	−0.0023 (8)
C9	0.0603 (11)	0.0470 (10)	0.0474 (10)	0.0030 (8)	−0.0005 (9)	0.0053 (8)
C10	0.0557 (10)	0.0455 (10)	0.0495 (10)	0.0001 (8)	0.0091 (8)	0.0010 (8)
C11	0.0499 (10)	0.0483 (10)	0.0494 (11)	−0.0007 (8)	0.0040 (8)	0.0022 (8)
C12	0.0503 (10)	0.0486 (10)	0.0416 (9)	−0.0048 (8)	0.0007 (8)	0.0028 (8)
C13	0.0515 (10)	0.0502 (11)	0.0481 (10)	0.0006 (8)	0.0029 (8)	−0.0056 (8)
C14	0.0722 (13)	0.0654 (13)	0.0783 (15)	−0.0021 (11)	0.0277 (12)	−0.0120 (11)
C15	0.0663 (12)	0.0599 (12)	0.0457 (11)	0.0063 (10)	−0.0046 (9)	0.0045 (9)
C16	0.0896 (17)	0.0990 (19)	0.0737 (15)	0.0358 (15)	0.0092 (13)	0.0178 (14)
C17	0.1087 (19)	0.0920 (18)	0.0548 (13)	0.0203 (15)	0.0165 (13)	0.0172 (12)
C18	0.0495 (10)	0.0391 (9)	0.0436 (9)	0.0042 (7)	0.0041 (8)	−0.0019 (7)
C19	0.0544 (10)	0.0573 (11)	0.0481 (10)	0.0006 (9)	0.0064 (8)	0.0038 (9)
C20	0.0727 (13)	0.0614 (12)	0.0437 (10)	0.0064 (10)	0.0016 (9)	0.0065 (9)
C21	0.0584 (12)	0.0567 (12)	0.0572 (12)	0.0080 (9)	−0.0111 (9)	−0.0031 (10)
C22	0.0464 (10)	0.0647 (13)	0.0736 (14)	0.0022 (9)	0.0042 (10)	−0.0006 (11)
C23	0.0555 (11)	0.0580 (11)	0.0508 (11)	0.0036 (9)	0.0094 (9)	0.0054 (9)

Geometric parameters (Å, º) top

S1—C12	1.6785 (19)	C9—H9A	0.9300
F1—C21	1.365 (2)	C10—C11	1.431 (3)
N1—C1	1.375 (2)	C10—H10A	0.9300
N1—C8	1.398 (2)	C11—H11A	0.9300
N1—C15	1.480 (2)	C13—C14	1.479 (3)
N2—C11	1.278 (2)	C14—H14A	0.9600
N2—N3	1.405 (2)	C14—H14B	0.9600
N3—C13	1.372 (2)	C14—H14C	0.9600
N3—C12	1.377 (2)	C15—C16	1.491 (3)
N4—C12	1.332 (2)	C15—C17	1.496 (3)
N4—N5	1.383 (2)	C15—H15A	0.9800
N4—H4B	0.91 (2)	C16—H16A	0.9600
N5—C13	1.297 (2)	C16—H16B	0.9600
C1—C2	1.400 (3)	C16—H16C	0.9600
C1—C6	1.410 (2)	C17—H17A	0.9600
C2—C3	1.365 (3)	C17—H17B	0.9600
C2—H2A	0.9300	C17—H17C	0.9600
C3—C4	1.394 (3)	C18—C23	1.385 (2)
C3—H3A	0.9300	C18—C19	1.393 (2)
C4—C5	1.371 (3)	C19—C20	1.377 (3)
C4—H4A	0.9300	C19—H19A	0.9300
C5—C6	1.396 (3)	C20—C21	1.361 (3)
C5—H5A	0.9300	C20—H20A	0.9300
C6—C7	1.426 (2)	C21—C22	1.363 (3)
C7—C8	1.384 (2)	C22—C23	1.376 (3)
C7—C18	1.480 (2)	C22—H22A	0.9300
C8—C9	1.448 (3)	C23—H23A	0.9300
C9—C10	1.322 (2)

C1—N1—C8	108.31 (14)	N3—C12—S1	128.32 (14)
C1—N1—C15	126.00 (15)	N5—C13—N3	110.63 (16)
C8—N1—C15	125.60 (16)	N5—C13—C14	126.34 (17)
C11—N2—N3	113.96 (15)	N3—C13—C14	123.02 (17)
C13—N3—C12	109.04 (15)	C13—C14—H14A	109.5
C13—N3—N2	122.74 (14)	C13—C14—H14B	109.5
C12—N3—N2	127.16 (15)	H14A—C14—H14B	109.5
C12—N4—N5	114.22 (16)	C13—C14—H14C	109.5
C12—N4—H4B	126.7 (14)	H14A—C14—H14C	109.5
N5—N4—H4B	119.1 (14)	H14B—C14—H14C	109.5
C13—N5—N4	103.77 (15)	N1—C15—C16	112.83 (18)
N1—C1—C2	131.40 (17)	N1—C15—C17	111.16 (17)
N1—C1—C6	108.25 (15)	C16—C15—C17	116.2 (2)
C2—C1—C6	120.35 (18)	N1—C15—H15A	105.2
C3—C2—C1	118.28 (19)	C16—C15—H15A	105.2
C3—C2—H2A	120.9	C17—C15—H15A	105.2
C1—C2—H2A	120.9	C15—C16—H16A	109.5
C2—C3—C4	121.82 (19)	C15—C16—H16B	109.5
C2—C3—H3A	119.1	H16A—C16—H16B	109.5
C4—C3—H3A	119.1	C15—C16—H16C	109.5
C5—C4—C3	120.6 (2)	H16A—C16—H16C	109.5
C5—C4—H4A	119.7	H16B—C16—H16C	109.5
C3—C4—H4A	119.7	C15—C17—H17A	109.5
C4—C5—C6	119.07 (19)	C15—C17—H17B	109.5
C4—C5—H5A	120.5	H17A—C17—H17B	109.5
C6—C5—H5A	120.5	C15—C17—H17C	109.5
C5—C6—C1	119.82 (17)	H17A—C17—H17C	109.5
C5—C6—C7	132.71 (17)	H17B—C17—H17C	109.5
C1—C6—C7	107.42 (15)	C23—C18—C19	117.50 (17)
C8—C7—C6	106.79 (15)	C23—C18—C7	121.29 (16)
C8—C7—C18	129.11 (16)	C19—C18—C7	121.02 (16)
C6—C7—C18	123.81 (15)	C20—C19—C18	121.35 (18)
C7—C8—N1	109.23 (15)	C20—C19—H19A	119.3
C7—C8—C9	129.40 (16)	C18—C19—H19A	119.3
N1—C8—C9	121.36 (16)	C21—C20—C19	118.57 (18)
C10—C9—C8	126.37 (17)	C21—C20—H20A	120.7
C10—C9—H9A	116.8	C19—C20—H20A	120.7
C8—C9—H9A	116.8	C20—C21—C22	122.43 (18)
C9—C10—C11	122.75 (17)	C20—C21—F1	119.42 (19)
C9—C10—H10A	118.6	C22—C21—F1	118.15 (19)
C11—C10—H10A	118.6	C21—C22—C23	118.45 (19)
N2—C11—C10	119.87 (17)	C21—C22—H22A	120.8
N2—C11—H11A	120.1	C23—C22—H22A	120.8
C10—C11—H11A	120.1	C22—C23—C18	121.70 (18)
N4—C12—N3	102.30 (15)	C22—C23—H23A	119.2
N4—C12—S1	129.35 (14)	C18—C23—H23A	119.2

C11—N2—N3—C13	135.05 (17)	N3—N2—C11—C10	176.73 (15)
C11—N2—N3—C12	−58.1 (2)	C9—C10—C11—N2	174.77 (18)
C12—N4—N5—C13	0.3 (2)	N5—N4—C12—N3	1.0 (2)
C8—N1—C1—C2	−179.70 (19)	N5—N4—C12—S1	−177.04 (13)
C15—N1—C1—C2	−3.0 (3)	C13—N3—C12—N4	−1.95 (18)
C8—N1—C1—C6	−0.5 (2)	N2—N3—C12—N4	−170.26 (15)
C15—N1—C1—C6	176.20 (16)	C13—N3—C12—S1	176.15 (14)
N1—C1—C2—C3	176.7 (2)	N2—N3—C12—S1	7.8 (2)
C6—C1—C2—C3	−2.4 (3)	N4—N5—C13—N3	−1.6 (2)
C1—C2—C3—C4	0.6 (3)	N4—N5—C13—C14	179.73 (18)
C2—C3—C4—C5	1.4 (3)	C12—N3—C13—N5	2.3 (2)
C3—C4—C5—C6	−1.5 (3)	N2—N3—C13—N5	171.27 (15)
C4—C5—C6—C1	−0.4 (3)	C12—N3—C13—C14	−178.93 (17)
C4—C5—C6—C7	−177.33 (19)	N2—N3—C13—C14	−10.0 (3)
N1—C1—C6—C5	−176.99 (16)	C1—N1—C15—C16	69.7 (3)
C2—C1—C6—C5	2.3 (3)	C8—N1—C15—C16	−114.2 (2)
N1—C1—C6—C7	0.7 (2)	C1—N1—C15—C17	−62.8 (3)
C2—C1—C6—C7	−179.99 (17)	C8—N1—C15—C17	113.3 (2)
C5—C6—C7—C8	176.61 (19)	C8—C7—C18—C23	−58.3 (3)
C1—C6—C7—C8	−0.63 (19)	C6—C7—C18—C23	114.7 (2)
C5—C6—C7—C18	2.3 (3)	C8—C7—C18—C19	126.8 (2)
C1—C6—C7—C18	−174.99 (15)	C6—C7—C18—C19	−60.2 (2)
C6—C7—C8—N1	0.35 (19)	C23—C18—C19—C20	1.1 (3)
C18—C7—C8—N1	174.31 (16)	C7—C18—C19—C20	176.15 (17)
C6—C7—C8—C9	179.80 (18)	C18—C19—C20—C21	−0.6 (3)
C18—C7—C8—C9	−6.2 (3)	C19—C20—C21—C22	−0.1 (3)
C1—N1—C8—C7	0.1 (2)	C19—C20—C21—F1	−179.84 (17)
C15—N1—C8—C7	−176.62 (17)	C20—C21—C22—C23	0.4 (3)
C1—N1—C8—C9	−179.43 (17)	F1—C21—C22—C23	−179.90 (18)
C15—N1—C8—C9	3.9 (3)	C21—C22—C23—C18	0.1 (3)
C7—C8—C9—C10	−31.3 (3)	C19—C18—C23—C22	−0.8 (3)
N1—C8—C9—C10	148.07 (19)	C7—C18—C23—C22	−175.87 (17)
C8—C9—C10—C11	179.64 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C18–C23 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···S1ⁱ	0.91 (2)	2.35 (2)	3.257 (2)	177.1 (15)
C4—H4A···Cg1ⁱⁱ	0.93	2.93	3.724 (2)	144

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

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

Supporting information

Key indicators

checkCIF/PLATON results

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