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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015020101/su5226sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015020101/su5226Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015020101/su5226Isup3.cml
Supplementary material

CCDC reference: 1433130

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](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
C23H22FN5SF(000) = 880
Mr = 419.51Dx = 1.286 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.4388 (8) ÅCell parameters from 5835 reflections
b = 23.482 (3) Åθ = 2.8–27.5°
c = 14.572 (3) ŵ = 0.18 mm1
β = 100.5009 (19)°T = 297 K
V = 2166.3 (6) Å3Block, yellow
Z = 40.40 × 0.27 × 0.09 mm
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer
5094 independent reflections
Radiation source: fine-focus sealed tube3393 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 27.8°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 88
Tmin = 0.779, Tmax = 0.932k = 3030
24228 measured reflectionsl = 1918
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: mixed
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0559P)2 + 0.3794P]
where P = (Fo2 + 2Fc2)/3
5094 reflections(Δ/σ)max = 0.001
278 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
S10.39854 (8)0.40778 (2)0.98203 (4)0.06099 (17)
F10.5717 (2)0.13276 (6)1.27264 (9)0.0912 (4)
N10.3776 (2)0.17803 (6)0.86118 (10)0.0523 (4)
N20.0328 (2)0.36814 (6)1.09831 (11)0.0512 (4)
N30.0953 (2)0.42497 (6)1.09021 (10)0.0464 (3)
N40.2694 (3)0.49906 (7)1.07257 (11)0.0540 (4)
H4B0.358 (3)0.5255 (9)1.0558 (15)0.073 (7)*
N50.1315 (3)0.51498 (7)1.13047 (11)0.0564 (4)
C10.4000 (3)0.12025 (8)0.87117 (12)0.0497 (4)
C20.5378 (3)0.08101 (9)0.81951 (14)0.0598 (5)
H2A0.64130.09290.77020.072*
C30.5163 (3)0.02485 (9)0.84345 (15)0.0655 (6)
H3A0.60610.00170.80930.079*
C40.3635 (3)0.00615 (9)0.91768 (15)0.0636 (5)
H4A0.35090.03250.93130.076*
C50.2315 (3)0.04425 (8)0.97074 (14)0.0547 (5)
H5A0.13180.03181.02110.066*
C60.2489 (3)0.10201 (7)0.94809 (12)0.0457 (4)
C70.1334 (3)0.15099 (7)0.98611 (11)0.0446 (4)
C80.2146 (3)0.19687 (8)0.93150 (12)0.0474 (4)
C90.1544 (3)0.25633 (8)0.93989 (13)0.0529 (4)
H9A0.16960.27720.88480.063*
C100.0801 (3)0.28383 (8)1.01813 (13)0.0503 (4)
H10A0.06410.26401.07430.060*
C110.0232 (3)0.34278 (8)1.02010 (13)0.0498 (4)
H11A0.02700.36260.96460.060*
C120.2548 (3)0.44453 (8)1.04702 (12)0.0478 (4)
C130.0300 (3)0.46845 (8)1.14103 (13)0.0507 (4)
C140.1374 (3)0.46154 (10)1.19744 (16)0.0702 (6)
H14A0.26610.44981.15780.105*
H14B0.15980.49711.22650.105*
H14C0.09510.43321.24460.105*
C150.4963 (3)0.21375 (9)0.78577 (13)0.0592 (5)
H15A0.43580.25200.79670.071*
C160.7234 (4)0.22020 (12)0.79263 (17)0.0881 (8)
H16A0.79330.24320.74180.132*
H16B0.73420.23820.85080.132*
H16C0.78880.18330.78970.132*
C170.4518 (4)0.19635 (11)0.69253 (15)0.0850 (7)
H17A0.52200.22190.64560.127*
H17B0.50240.15830.67850.127*
H17C0.30230.19760.69370.127*
C180.0509 (3)0.14878 (7)1.06333 (12)0.0446 (4)
C190.0324 (3)0.12700 (8)1.15036 (13)0.0536 (5)
H19A0.09960.11581.16110.064*
C200.2057 (3)0.12172 (9)1.22087 (14)0.0604 (5)
H20A0.19150.10751.27890.072*
C210.3980 (3)0.13781 (9)1.20369 (14)0.0602 (5)
C220.4252 (3)0.15878 (9)1.11945 (15)0.0624 (5)
H22A0.55850.16931.10940.075*
C230.2508 (3)0.16406 (8)1.04971 (13)0.0548 (5)
H23A0.26760.17830.99190.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0679 (3)0.0568 (3)0.0619 (3)0.0073 (2)0.0215 (3)0.0065 (2)
F10.0731 (8)0.1057 (11)0.0794 (9)0.0101 (7)0.0271 (7)0.0028 (8)
N10.0596 (9)0.0492 (9)0.0423 (8)0.0011 (7)0.0065 (7)0.0004 (7)
N20.0588 (9)0.0437 (8)0.0510 (9)0.0046 (7)0.0099 (7)0.0012 (7)
N30.0505 (8)0.0427 (8)0.0439 (8)0.0035 (6)0.0032 (7)0.0005 (6)
N40.0575 (9)0.0487 (9)0.0558 (10)0.0077 (8)0.0106 (8)0.0006 (7)
N50.0577 (9)0.0509 (9)0.0594 (10)0.0023 (8)0.0073 (8)0.0055 (8)
C10.0537 (10)0.0520 (11)0.0423 (10)0.0005 (8)0.0059 (8)0.0043 (8)
C20.0636 (12)0.0635 (13)0.0485 (11)0.0081 (10)0.0005 (9)0.0069 (9)
C30.0713 (13)0.0632 (13)0.0612 (13)0.0189 (11)0.0100 (11)0.0146 (10)
C40.0787 (14)0.0463 (11)0.0681 (13)0.0077 (10)0.0197 (12)0.0062 (10)
C50.0589 (11)0.0493 (11)0.0564 (11)0.0029 (9)0.0121 (9)0.0011 (9)
C60.0490 (10)0.0459 (10)0.0424 (9)0.0021 (8)0.0091 (8)0.0026 (8)
C70.0495 (10)0.0432 (9)0.0402 (9)0.0031 (8)0.0061 (8)0.0008 (7)
C80.0523 (10)0.0471 (10)0.0407 (9)0.0010 (8)0.0023 (8)0.0023 (8)
C90.0603 (11)0.0470 (10)0.0474 (10)0.0030 (8)0.0005 (9)0.0053 (8)
C100.0557 (10)0.0455 (10)0.0495 (10)0.0001 (8)0.0091 (8)0.0010 (8)
C110.0499 (10)0.0483 (10)0.0494 (11)0.0007 (8)0.0040 (8)0.0022 (8)
C120.0503 (10)0.0486 (10)0.0416 (9)0.0048 (8)0.0007 (8)0.0028 (8)
C130.0515 (10)0.0502 (11)0.0481 (10)0.0006 (8)0.0029 (8)0.0056 (8)
C140.0722 (13)0.0654 (13)0.0783 (15)0.0021 (11)0.0277 (12)0.0120 (11)
C150.0663 (12)0.0599 (12)0.0457 (11)0.0063 (10)0.0046 (9)0.0045 (9)
C160.0896 (17)0.0990 (19)0.0737 (15)0.0358 (15)0.0092 (13)0.0178 (14)
C170.1087 (19)0.0920 (18)0.0548 (13)0.0203 (15)0.0165 (13)0.0172 (12)
C180.0495 (10)0.0391 (9)0.0436 (9)0.0042 (7)0.0041 (8)0.0019 (7)
C190.0544 (10)0.0573 (11)0.0481 (10)0.0006 (9)0.0064 (8)0.0038 (9)
C200.0727 (13)0.0614 (12)0.0437 (10)0.0064 (10)0.0016 (9)0.0065 (9)
C210.0584 (12)0.0567 (12)0.0572 (12)0.0080 (9)0.0111 (9)0.0031 (10)
C220.0464 (10)0.0647 (13)0.0736 (14)0.0022 (9)0.0042 (10)0.0006 (11)
C230.0555 (11)0.0580 (11)0.0508 (11)0.0036 (9)0.0094 (9)0.0054 (9)
Geometric parameters (Å, º) top
S1—C121.6785 (19)C9—H9A0.9300
F1—C211.365 (2)C10—C111.431 (3)
N1—C11.375 (2)C10—H10A0.9300
N1—C81.398 (2)C11—H11A0.9300
N1—C151.480 (2)C13—C141.479 (3)
N2—C111.278 (2)C14—H14A0.9600
N2—N31.405 (2)C14—H14B0.9600
N3—C131.372 (2)C14—H14C0.9600
N3—C121.377 (2)C15—C161.491 (3)
N4—C121.332 (2)C15—C171.496 (3)
N4—N51.383 (2)C15—H15A0.9800
N4—H4B0.91 (2)C16—H16A0.9600
N5—C131.297 (2)C16—H16B0.9600
C1—C21.400 (3)C16—H16C0.9600
C1—C61.410 (2)C17—H17A0.9600
C2—C31.365 (3)C17—H17B0.9600
C2—H2A0.9300C17—H17C0.9600
C3—C41.394 (3)C18—C231.385 (2)
C3—H3A0.9300C18—C191.393 (2)
C4—C51.371 (3)C19—C201.377 (3)
C4—H4A0.9300C19—H19A0.9300
C5—C61.396 (3)C20—C211.361 (3)
C5—H5A0.9300C20—H20A0.9300
C6—C71.426 (2)C21—C221.363 (3)
C7—C81.384 (2)C22—C231.376 (3)
C7—C181.480 (2)C22—H22A0.9300
C8—C91.448 (3)C23—H23A0.9300
C9—C101.322 (2)
C1—N1—C8108.31 (14)N3—C12—S1128.32 (14)
C1—N1—C15126.00 (15)N5—C13—N3110.63 (16)
C8—N1—C15125.60 (16)N5—C13—C14126.34 (17)
C11—N2—N3113.96 (15)N3—C13—C14123.02 (17)
C13—N3—C12109.04 (15)C13—C14—H14A109.5
C13—N3—N2122.74 (14)C13—C14—H14B109.5
C12—N3—N2127.16 (15)H14A—C14—H14B109.5
C12—N4—N5114.22 (16)C13—C14—H14C109.5
C12—N4—H4B126.7 (14)H14A—C14—H14C109.5
N5—N4—H4B119.1 (14)H14B—C14—H14C109.5
C13—N5—N4103.77 (15)N1—C15—C16112.83 (18)
N1—C1—C2131.40 (17)N1—C15—C17111.16 (17)
N1—C1—C6108.25 (15)C16—C15—C17116.2 (2)
C2—C1—C6120.35 (18)N1—C15—H15A105.2
C3—C2—C1118.28 (19)C16—C15—H15A105.2
C3—C2—H2A120.9C17—C15—H15A105.2
C1—C2—H2A120.9C15—C16—H16A109.5
C2—C3—C4121.82 (19)C15—C16—H16B109.5
C2—C3—H3A119.1H16A—C16—H16B109.5
C4—C3—H3A119.1C15—C16—H16C109.5
C5—C4—C3120.6 (2)H16A—C16—H16C109.5
C5—C4—H4A119.7H16B—C16—H16C109.5
C3—C4—H4A119.7C15—C17—H17A109.5
C4—C5—C6119.07 (19)C15—C17—H17B109.5
C4—C5—H5A120.5H17A—C17—H17B109.5
C6—C5—H5A120.5C15—C17—H17C109.5
C5—C6—C1119.82 (17)H17A—C17—H17C109.5
C5—C6—C7132.71 (17)H17B—C17—H17C109.5
C1—C6—C7107.42 (15)C23—C18—C19117.50 (17)
C8—C7—C6106.79 (15)C23—C18—C7121.29 (16)
C8—C7—C18129.11 (16)C19—C18—C7121.02 (16)
C6—C7—C18123.81 (15)C20—C19—C18121.35 (18)
C7—C8—N1109.23 (15)C20—C19—H19A119.3
C7—C8—C9129.40 (16)C18—C19—H19A119.3
N1—C8—C9121.36 (16)C21—C20—C19118.57 (18)
C10—C9—C8126.37 (17)C21—C20—H20A120.7
C10—C9—H9A116.8C19—C20—H20A120.7
C8—C9—H9A116.8C20—C21—C22122.43 (18)
C9—C10—C11122.75 (17)C20—C21—F1119.42 (19)
C9—C10—H10A118.6C22—C21—F1118.15 (19)
C11—C10—H10A118.6C21—C22—C23118.45 (19)
N2—C11—C10119.87 (17)C21—C22—H22A120.8
N2—C11—H11A120.1C23—C22—H22A120.8
C10—C11—H11A120.1C22—C23—C18121.70 (18)
N4—C12—N3102.30 (15)C22—C23—H23A119.2
N4—C12—S1129.35 (14)C18—C23—H23A119.2
C11—N2—N3—C13135.05 (17)N3—N2—C11—C10176.73 (15)
C11—N2—N3—C1258.1 (2)C9—C10—C11—N2174.77 (18)
C12—N4—N5—C130.3 (2)N5—N4—C12—N31.0 (2)
C8—N1—C1—C2179.70 (19)N5—N4—C12—S1177.04 (13)
C15—N1—C1—C23.0 (3)C13—N3—C12—N41.95 (18)
C8—N1—C1—C60.5 (2)N2—N3—C12—N4170.26 (15)
C15—N1—C1—C6176.20 (16)C13—N3—C12—S1176.15 (14)
N1—C1—C2—C3176.7 (2)N2—N3—C12—S17.8 (2)
C6—C1—C2—C32.4 (3)N4—N5—C13—N31.6 (2)
C1—C2—C3—C40.6 (3)N4—N5—C13—C14179.73 (18)
C2—C3—C4—C51.4 (3)C12—N3—C13—N52.3 (2)
C3—C4—C5—C61.5 (3)N2—N3—C13—N5171.27 (15)
C4—C5—C6—C10.4 (3)C12—N3—C13—C14178.93 (17)
C4—C5—C6—C7177.33 (19)N2—N3—C13—C1410.0 (3)
N1—C1—C6—C5176.99 (16)C1—N1—C15—C1669.7 (3)
C2—C1—C6—C52.3 (3)C8—N1—C15—C16114.2 (2)
N1—C1—C6—C70.7 (2)C1—N1—C15—C1762.8 (3)
C2—C1—C6—C7179.99 (17)C8—N1—C15—C17113.3 (2)
C5—C6—C7—C8176.61 (19)C8—C7—C18—C2358.3 (3)
C1—C6—C7—C80.63 (19)C6—C7—C18—C23114.7 (2)
C5—C6—C7—C182.3 (3)C8—C7—C18—C19126.8 (2)
C1—C6—C7—C18174.99 (15)C6—C7—C18—C1960.2 (2)
C6—C7—C8—N10.35 (19)C23—C18—C19—C201.1 (3)
C18—C7—C8—N1174.31 (16)C7—C18—C19—C20176.15 (17)
C6—C7—C8—C9179.80 (18)C18—C19—C20—C210.6 (3)
C18—C7—C8—C96.2 (3)C19—C20—C21—C220.1 (3)
C1—N1—C8—C70.1 (2)C19—C20—C21—F1179.84 (17)
C15—N1—C8—C7176.62 (17)C20—C21—C22—C230.4 (3)
C1—N1—C8—C9179.43 (17)F1—C21—C22—C23179.90 (18)
C15—N1—C8—C93.9 (3)C21—C22—C23—C180.1 (3)
C7—C8—C9—C1031.3 (3)C19—C18—C23—C220.8 (3)
N1—C8—C9—C10148.07 (19)C7—C18—C23—C22175.87 (17)
C8—C9—C10—C11179.64 (17)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C18–C23 ring.
D—H···AD—HH···AD···AD—H···A
N4—H4B···S1i0.91 (2)2.35 (2)3.257 (2)177.1 (15)
C4—H4A···Cg1ii0.932.933.724 (2)144
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y, z+2.
 

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