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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1169–o1170.
Published online 2010 April 24. doi:  10.1107/S1600536810014650
PMCID: PMC2979057

4-(5-Chloro-2-methyl­phen­yl)-1-[2-oxo-5-(trifluoro­meth­oxy)indolin-3-yl­idene]thio­semicarbazide

Abstract

The asymmetric unit of the title compound, C17H12ClF3N4O2S, contains two mol­ecules, which differ in their planarity and hydrogen bonding. In one mol­ecule, the 2-oxoindolin (C8/N/O A), thio­semicarbazide (N3/C/S B) and 5-chloro-2-methyl­phenyl (C7/Cl C) units are planar with r.m.s. deviations of 0.0110, 0.0173 and 0.0259 Å, respectively. The dihedral angles A/B, B/C and A/C are 1.74 (15), 40.70 (13) and 41.00 (11)°, respectively. In the other mol­ecule the deviations are 0.0455, 0.0007 and 0.0143 Å, respectively, and the dihedral angles are 5.01 (14), 4.53 (16) and 3.38 (13)°, respectively. In both mol­ecules, intra­molecular N—H(...)N and N—H(...)O hydrogen bonds form S(5) and S(6) ring motifs, respectively and C—H(...)S interactions occur. In one of the molecules, an intramolecular C—H(...)F interaction is also present. In the crystal, the mol­ecules are linked by N—H(...)O, C—H(...)F, C—H(...)O and N—H(...)S hydrogen bonding, forming a polymeric network.

Related literature

For our work on 1H-indole-2,3-dione derivatives having pharmaceutical applications, see: Pervez et al. (2007 [triangle], 2008 [triangle], 2009a [triangle], 2010a [triangle]). For the structures of 1-(5-nitro-2-oxoindolin-3-yl­idene)-4-o-tolyl­thio­semicarbazide and 4-(2-fluoro­phen­yl)-1-(2-oxoindolin-3-yl­idene)thio­semicarbazide, see: Pervez et al. (2009b [triangle], 2010b [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1169-scheme1.jpg

Experimental

Crystal data

  • C17H12ClF3N4O2S
  • M r = 428.82
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1169-efi1.jpg
  • a = 10.5808 (5) Å
  • b = 11.0262 (5) Å
  • c = 17.1743 (7) Å
  • α = 102.855 (3)°
  • β = 94.766 (3)°
  • γ = 107.814 (2)°
  • V = 1834.96 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.37 mm−1
  • T = 296 K
  • 0.24 × 0.18 × 0.16 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.924, T max = 0.945
  • 33611 measured reflections
  • 6822 independent reflections
  • 3927 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.145
  • S = 1.02
  • 6822 reflections
  • 507 parameters
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014650/bq2207sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014650/bq2207Isup2.hkl

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

Acknowledgments

HP, MSI and NS thank the Higher Education Commission (HEC), Pakistan, for financial assistance under the National Research Program for Universities (Project No. 20-873/R&D/07/452).

supplementary crystallographic information

Comment

In continuation of our work on 1H-indole-2,3-dione derivatives having pharmaceutical applications (Pervez et al., 2007, 2008, 2009a, 2010a), we report herein the synthesis and crystal structure of the title compound (I, Fig. 1).

The crystal structures of (II) i.e. 1-(5-nitro-2-oxoindolin-3-ylidene)-4-o-tolylthiosemicarbazide (Pervez et al., 2009b) and (III) i.e. 4-(2-fluorophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide (Pervez et al., 2010b) have been published previously. The title compound (I) differs from (II) due to the presence of trifluoromethoxy instead of nitro function and an additional chloro group at position-5 of the isatin scaffold and phenyl ring substituted at N4 of the thiosemicarbazone moiety, respectively. From (III), it differs due to the presence of trifluoromethoxy group at position-5 of the isatin scaffold, and methyl instead of fluoro and an additional chloro function at position-5 of the phenyl ring substituted at N4 of the thiosemicarbazone moiety.

The asymmetric unit of title compound consist of two molecules. In one molecule, the 2-oxoindolin A (C1–C8/N1/O1), thiosemicarbazide B (N2/N3/C9/S1/N4) and the 5-Chloro-2-methylphenyl C (C10–C16/Cl1) are planar with maximum r.m.s. deviations of 0.0110 Å, 0.0173 Å and 0.0259 Å, respectively. The dihedral angles between A/B, B/C and A/C are 1.74 (15)°, 40.70 (13)° and 41.00 (11)°, respectively. In the other molecule the same groups D (C18—C25/N5/O3), E (N6/N7/C26/S2/N8) and F (C27—C33/CL2) are also planar with maximum r.m.s. deviations of 0.0455 Å, 0.0007 Å and 0.0143 Å, respectively. The dihedral angles between D/E, E/F and D/F are 5.01 (14)°, 4.53 (16)° and 3.38 (13)°, respectively. These values show that the later molecule is more planar than the former. Due to intramolecular H-bondings (Table 1, Fig. 2), S(5) and S(6) (Bernstein et al., 1995) ring motifs are formed in each molecule. The molecules are stabilized in the form of polymeric network through intermolecular H-bonding of types N—H···O , C—H···F and N—H···S.

Experimental

4-(5-Chloro-2-methylphenyl)thiosemicarbazide (0.86 g, 4.0 mmol) dissolved in ethanol (10 ml) was added to a hot solution of 5-(trifluoromethoxy) indolin-2,3-dione (0.92 g, 4.0 mmol) in 50% aqueous ethanol (20 ml) containing a catalytic quantity of glacial acetic acid. The reaction mixture was then refluxed for 2 h. The orange colored amorphous solid formed during refluxing was collected by suction filtration. Thorough washing with hot aqueous ethanol afforded the title compound (I) in pure form (1.10 g, 64%), m.p. 513 K. The crystals of (I) for x-ray analysis were grown in ethyl acetate-petroleum ether (2:5) solvent system at room temperature by diffusion method.

Refinement

The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å, C–N = 0.86 Å) and refined as riding with Uiso(H) = xUeq(C, N), where x = 1.5 for methyl and 1.2 for other H-atoms.

Figures

Fig. 1.
View of (I) with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level.
Fig. 2.
The partial packing of (I) (PLATON; Spek, 2009) which shows that molecules form ring motifs and form polymeric network.

Crystal data

C17H12ClF3N4O2SZ = 4
Mr = 428.82F(000) = 872
Triclinic, P1Dx = 1.552 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5808 (5) ÅCell parameters from 6822 reflections
b = 11.0262 (5) Åθ = 2.1–25.5°
c = 17.1743 (7) ŵ = 0.37 mm1
α = 102.855 (3)°T = 296 K
β = 94.766 (3)°Prism, red
γ = 107.814 (2)°0.24 × 0.18 × 0.16 mm
V = 1834.96 (15) Å3

Data collection

Bruker Kappa APEXII CCD diffractometer6822 independent reflections
Radiation source: fine-focus sealed tube3927 reflections with I > 2σ(I)
graphiteRint = 0.049
Detector resolution: 7.80 pixels mm-1θmax = 25.5°, θmin = 2.1°
ω scansh = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −13→13
Tmin = 0.924, Tmax = 0.945l = −20→20
33611 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0588P)2 + 0.8346P] where P = (Fo2 + 2Fc2)/3
6822 reflections(Δ/σ)max < 0.001
507 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = −0.36 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
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 > σ(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.

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

xyzUiso*/Ueq
Cl10.90141 (12)1.08034 (18)0.04378 (8)0.1311 (7)
S10.73013 (8)1.08876 (10)0.33045 (6)0.0663 (4)
F1−0.2587 (4)0.5431 (3)0.0906 (2)0.1816 (18)
F2−0.2738 (3)0.6739 (3)0.02089 (18)0.1430 (16)
F3−0.0876 (4)0.6495 (4)0.05415 (19)0.167 (2)
O10.3721 (2)0.8851 (2)0.46034 (14)0.0616 (9)
O2−0.1786 (3)0.7545 (3)0.14412 (19)0.0825 (11)
N10.1403 (2)0.7922 (2)0.42522 (16)0.0498 (9)
N20.3438 (3)0.9308 (2)0.29315 (17)0.0503 (9)
N30.4732 (2)0.9813 (2)0.32968 (17)0.0522 (9)
N40.5207 (3)1.0337 (3)0.21286 (17)0.0585 (10)
C10.2674 (3)0.8546 (3)0.4138 (2)0.0494 (11)
C20.2519 (3)0.8751 (3)0.3308 (2)0.0472 (11)
C30.1102 (3)0.8184 (3)0.29786 (19)0.0455 (11)
C40.0382 (3)0.8115 (3)0.2255 (2)0.0552 (12)
C5−0.1000 (3)0.7532 (3)0.2146 (2)0.0606 (14)
C6−0.1641 (3)0.7044 (3)0.2728 (2)0.0646 (14)
C7−0.0922 (3)0.7113 (3)0.3450 (2)0.0587 (14)
C80.0459 (3)0.7697 (3)0.35726 (19)0.0457 (11)
C90.5704 (3)1.0342 (3)0.2870 (2)0.0504 (11)
C100.5856 (3)1.0824 (3)0.1519 (2)0.0552 (12)
C110.5210 (4)1.1454 (3)0.1090 (2)0.0644 (14)
C120.5790 (5)1.1884 (4)0.0471 (3)0.0876 (19)
C130.6963 (5)1.1717 (5)0.0280 (3)0.0936 (19)
C140.7571 (4)1.1069 (4)0.0704 (2)0.0796 (16)
C150.7029 (3)1.0613 (4)0.1325 (2)0.0666 (14)
C160.3887 (4)1.1624 (4)0.1257 (2)0.0859 (17)
C17−0.1989 (6)0.6580 (7)0.0794 (4)0.107 (3)
Cl20.91864 (10)0.86095 (10)0.77449 (6)0.0815 (4)
S20.40866 (10)0.58900 (11)0.67685 (6)0.0801 (4)
F40.4264 (4)0.5047 (4)0.1554 (2)0.1422 (17)
F50.4754 (3)0.7019 (3)0.2115 (2)0.1348 (14)
F60.4451 (3)0.6393 (4)0.08329 (19)0.1460 (16)
O30.0157 (2)0.3691 (2)0.47803 (14)0.0558 (8)
O40.2739 (4)0.5967 (4)0.1420 (2)0.1177 (16)
N5−0.0455 (3)0.3792 (3)0.34712 (17)0.0574 (10)
N60.2839 (2)0.5485 (2)0.45305 (15)0.0460 (9)
N70.2893 (2)0.5392 (2)0.52977 (15)0.0482 (9)
N80.5052 (2)0.6698 (3)0.54981 (16)0.0540 (9)
C180.0396 (3)0.4055 (3)0.4167 (2)0.0470 (11)
C190.1729 (3)0.4892 (3)0.40341 (18)0.0431 (10)
C200.1555 (3)0.4956 (3)0.32001 (19)0.0477 (11)
C210.2453 (3)0.5523 (3)0.2743 (2)0.0610 (12)
C220.1959 (4)0.5391 (4)0.1956 (2)0.0720 (16)
C230.0625 (5)0.4747 (4)0.1631 (2)0.0767 (16)
C24−0.0288 (4)0.4190 (4)0.2091 (2)0.0694 (12)
C250.0206 (3)0.4288 (3)0.2880 (2)0.0530 (11)
C260.4070 (3)0.6034 (3)0.58372 (18)0.0458 (10)
C270.6420 (3)0.7470 (3)0.5784 (2)0.0466 (10)
C280.7111 (3)0.8068 (3)0.5231 (2)0.0475 (11)
C290.8460 (3)0.8802 (3)0.5489 (3)0.0613 (14)
C300.9113 (3)0.8970 (3)0.6241 (3)0.0653 (14)
C310.8411 (3)0.8388 (3)0.6771 (2)0.0588 (14)
C320.7060 (3)0.7626 (3)0.6551 (2)0.0545 (11)
C330.6436 (3)0.7917 (3)0.4397 (2)0.0634 (14)
C340.3975 (7)0.6097 (6)0.1467 (3)0.104 (2)
H10.120710.769580.468710.0597*
H30.494610.980450.378920.0626*
H40.080740.844530.185660.0664*
H4A0.434790.997790.200020.0702*
H6−0.257340.666260.263410.0777*
H7−0.135350.677700.384420.0699*
H120.537051.230230.017300.1050*
H130.734711.20383−0.013260.1123*
H150.744091.017130.160950.0798*
H16A0.363211.211420.091220.1291*
H16B0.398121.209210.181290.1291*
H16C0.320681.077220.115240.1291*
H5−0.130380.336750.340110.0688*
H7A0.219240.492980.545110.0579*
H80.479950.664510.499910.0648*
H210.335510.597470.295810.0737*
H230.033140.468490.109310.0919*
H24−0.119480.376830.187700.0829*
H290.894180.919940.513080.0734*
H301.002080.947080.639310.0786*
H320.659490.722790.691430.0653*
H33A0.704360.847490.413520.0949*
H33B0.618780.701480.408920.0949*
H33C0.564480.816640.443080.0949*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0695 (8)0.2284 (17)0.0752 (8)0.0309 (9)0.0249 (6)0.0215 (9)
S10.0366 (5)0.0842 (7)0.0749 (7)0.0045 (4)0.0044 (4)0.0380 (5)
F10.236 (4)0.099 (2)0.140 (3)−0.011 (3)−0.058 (3)0.019 (2)
F20.142 (3)0.175 (3)0.095 (2)0.045 (2)−0.042 (2)0.035 (2)
F30.154 (3)0.267 (5)0.086 (2)0.105 (3)0.011 (2)0.010 (2)
O10.0414 (13)0.0727 (16)0.0665 (16)0.0138 (12)0.0039 (12)0.0189 (12)
O20.0667 (18)0.093 (2)0.082 (2)0.0219 (15)−0.0078 (16)0.0253 (17)
N10.0394 (15)0.0537 (16)0.0560 (18)0.0107 (12)0.0131 (13)0.0189 (13)
N20.0359 (15)0.0474 (15)0.0676 (18)0.0107 (12)0.0108 (13)0.0187 (14)
N30.0374 (15)0.0556 (16)0.0633 (18)0.0077 (12)0.0101 (13)0.0254 (14)
N40.0346 (14)0.0734 (19)0.0626 (19)0.0031 (13)0.0038 (14)0.0303 (15)
C10.044 (2)0.0438 (18)0.061 (2)0.0150 (15)0.0143 (17)0.0126 (16)
C20.0379 (18)0.0396 (17)0.064 (2)0.0102 (14)0.0147 (16)0.0149 (15)
C30.0398 (18)0.0387 (17)0.056 (2)0.0107 (14)0.0100 (16)0.0113 (15)
C40.052 (2)0.051 (2)0.064 (2)0.0149 (16)0.0162 (18)0.0184 (17)
C50.045 (2)0.062 (2)0.071 (3)0.0138 (17)−0.0010 (18)0.0194 (19)
C60.0373 (19)0.069 (2)0.084 (3)0.0099 (17)0.0101 (19)0.024 (2)
C70.0380 (19)0.064 (2)0.074 (3)0.0087 (16)0.0152 (18)0.0275 (19)
C80.0402 (18)0.0387 (17)0.058 (2)0.0120 (14)0.0141 (16)0.0119 (15)
C90.0404 (18)0.0454 (18)0.065 (2)0.0081 (15)0.0110 (16)0.0216 (16)
C100.050 (2)0.057 (2)0.047 (2)0.0020 (16)−0.0002 (16)0.0159 (17)
C110.078 (3)0.057 (2)0.047 (2)0.0118 (19)−0.0008 (19)0.0103 (17)
C120.118 (4)0.088 (3)0.058 (3)0.030 (3)0.011 (3)0.029 (2)
C130.108 (4)0.097 (3)0.053 (3)−0.003 (3)0.015 (3)0.026 (2)
C140.058 (2)0.099 (3)0.056 (3)−0.002 (2)0.009 (2)0.009 (2)
C150.050 (2)0.084 (3)0.058 (2)0.0109 (19)0.0067 (18)0.020 (2)
C160.098 (3)0.104 (3)0.066 (3)0.055 (3)−0.001 (2)0.018 (2)
C170.087 (4)0.135 (5)0.085 (4)0.023 (4)−0.011 (3)0.033 (4)
Cl20.0671 (6)0.0745 (7)0.0856 (7)0.0259 (5)−0.0283 (5)−0.0016 (5)
S20.0708 (7)0.0896 (7)0.0513 (6)−0.0154 (5)−0.0063 (5)0.0270 (5)
F40.186 (3)0.154 (3)0.144 (3)0.096 (3)0.083 (2)0.077 (2)
F50.138 (3)0.127 (2)0.110 (2)0.001 (2)0.033 (2)0.029 (2)
F60.164 (3)0.208 (3)0.106 (2)0.065 (3)0.065 (2)0.101 (2)
O30.0511 (13)0.0498 (13)0.0574 (15)0.0047 (10)0.0092 (11)0.0128 (11)
O40.094 (2)0.195 (4)0.086 (2)0.048 (3)0.019 (2)0.079 (2)
N50.0376 (15)0.0573 (17)0.0593 (19)0.0010 (13)−0.0052 (14)0.0053 (14)
N60.0423 (15)0.0445 (15)0.0426 (16)0.0062 (12)0.0007 (12)0.0082 (12)
N70.0407 (15)0.0456 (15)0.0450 (16)−0.0020 (12)0.0001 (12)0.0108 (12)
N80.0378 (15)0.0667 (18)0.0464 (16)0.0001 (13)−0.0026 (12)0.0205 (14)
C180.0428 (19)0.0360 (17)0.054 (2)0.0095 (14)0.0022 (16)0.0027 (15)
C190.0413 (18)0.0376 (16)0.0441 (19)0.0080 (14)0.0017 (14)0.0072 (14)
C200.0481 (19)0.0413 (18)0.048 (2)0.0113 (15)0.0013 (16)0.0076 (14)
C210.055 (2)0.071 (2)0.053 (2)0.0143 (18)−0.0011 (18)0.0215 (18)
C220.077 (3)0.090 (3)0.056 (2)0.030 (2)0.011 (2)0.030 (2)
C230.093 (3)0.091 (3)0.047 (2)0.036 (3)−0.007 (2)0.019 (2)
C240.066 (2)0.069 (2)0.058 (2)0.019 (2)−0.015 (2)0.0007 (19)
C250.051 (2)0.0454 (19)0.050 (2)0.0111 (16)−0.0055 (17)−0.0003 (16)
C260.0430 (18)0.0397 (17)0.0457 (19)0.0050 (14)−0.0019 (15)0.0088 (14)
C270.0359 (17)0.0374 (17)0.061 (2)0.0091 (14)−0.0010 (16)0.0095 (15)
C280.0397 (18)0.0409 (17)0.063 (2)0.0167 (14)0.0095 (16)0.0111 (15)
C290.041 (2)0.049 (2)0.092 (3)0.0141 (16)0.015 (2)0.0147 (19)
C300.0362 (19)0.051 (2)0.097 (3)0.0117 (16)0.003 (2)0.003 (2)
C310.046 (2)0.0453 (19)0.075 (3)0.0206 (17)−0.0128 (18)−0.0033 (17)
C320.047 (2)0.0478 (19)0.060 (2)0.0107 (16)−0.0034 (17)0.0084 (16)
C330.052 (2)0.072 (2)0.075 (3)0.0215 (18)0.0204 (19)0.032 (2)
C340.146 (5)0.105 (4)0.064 (3)0.029 (4)0.026 (4)0.044 (3)

Geometric parameters (Å, °)

Cl1—C141.719 (5)C6—C71.374 (5)
Cl2—C311.732 (3)C7—C81.381 (5)
S1—C91.656 (3)C10—C151.384 (5)
S2—C261.641 (3)C10—C111.388 (5)
F1—C171.296 (8)C11—C121.373 (6)
F2—C171.304 (7)C11—C161.510 (6)
F3—C171.311 (8)C12—C131.365 (8)
F4—C341.320 (8)C13—C141.375 (7)
F5—C341.335 (7)C14—C151.372 (5)
F6—C341.302 (7)C4—H40.9300
O1—C11.218 (4)C6—H60.9300
O2—C51.416 (5)C7—H70.9300
O2—C171.307 (8)C12—H120.9300
O3—C181.227 (4)C13—H130.9300
O4—C221.413 (6)C15—H150.9300
O4—C341.265 (9)C16—H16A0.9600
N1—C81.396 (4)C16—H16C0.9600
N1—C11.363 (4)C16—H16B0.9600
N2—N31.347 (4)C18—C191.498 (5)
N2—C21.287 (4)C19—C201.449 (4)
N3—C91.373 (4)C20—C211.374 (5)
N4—C91.335 (4)C20—C251.389 (5)
N4—C101.414 (4)C21—C221.367 (5)
N1—H10.8600C22—C231.374 (7)
N3—H30.8600C23—C241.384 (6)
N4—H4A0.8600C24—C251.380 (5)
N5—C251.397 (5)C27—C281.404 (5)
N5—C181.353 (4)C27—C321.380 (5)
N6—C191.284 (4)C28—C331.497 (5)
N6—N71.342 (3)C28—C291.385 (5)
N7—C261.374 (4)C29—C301.359 (7)
N8—C271.415 (4)C30—C311.369 (5)
N8—C261.334 (4)C31—C321.388 (5)
N5—H50.8600C21—H210.9300
N7—H7A0.8600C23—H230.9300
N8—H80.8600C24—H240.9300
C1—C21.496 (5)C29—H290.9300
C2—C31.445 (5)C30—H300.9300
C3—C81.388 (5)C32—H320.9300
C3—C41.377 (5)C33—H33A0.9600
C4—C51.383 (5)C33—H33B0.9600
C5—C61.370 (5)C33—H33C0.9600
Cl1···Cl1i3.369 (2)C21···F42.984 (5)
Cl1···Cl2ii3.3384 (17)C21···C33.599 (5)
Cl2···C25iii3.409 (3)C21···C23.452 (5)
Cl2···C4iv3.499 (3)C21···F52.930 (5)
Cl2···Cl1ii3.3384 (17)C21···C13.575 (5)
S1···N5v3.287 (3)C22···C33.600 (5)
S1···C153.325 (3)C25···Cl2iii3.409 (3)
S2···C323.245 (4)C25···C83.600 (5)
S1···H152.8700C28···C1iv3.578 (5)
S1···H30ii3.0000C29···C2iv3.494 (5)
S1···H5v2.6400C29···C1iv3.441 (5)
S2···H33Biii3.1300C30···O3iii3.406 (4)
S2···H322.5700C30···C2iv3.451 (5)
S2···H16Biv3.0100C30···C4iv3.509 (5)
F1···C63.142 (5)C30···C18iii3.459 (5)
F3···C43.030 (5)C30···C8iv3.500 (5)
F4···C212.984 (5)C30···C3iv3.211 (5)
F5···C212.930 (5)C31···C3iv3.576 (5)
F6···C12vi3.284 (6)C31···C19iii3.525 (5)
F2···H16Avii2.7800C31···C18iii3.454 (5)
F3···H42.7800C32···C19iii3.393 (5)
F4···H212.7700C32···S23.245 (4)
F5···H212.3800C33···O13.355 (4)
F6···H12vi2.4700C33···C7xi3.588 (5)
O1···C333.355 (4)C1···H32.5800
O1···N32.841 (3)C9···H152.9600
O1···N23.030 (4)C14···H24v3.0200
O1···O1iv3.043 (3)C16···H4A2.5700
O3···N63.049 (3)C18···H7A2.5800
O3···N1viii2.937 (3)C26···H322.8700
O3···N72.863 (3)C32···H16Biv3.0900
O3···O3viii2.945 (3)C33···H7xi3.1000
O3···C18viii2.976 (4)C33···H82.3400
O3···C30iii3.406 (4)C34···H212.7200
O1···H32.2100H1···O3viii2.1800
O1···H33C2.4000H3···H33C2.5700
O1···H3iv2.8400H3···C12.5800
O3···H7A2.2200H3···O12.2100
O3···H7viii2.8100H3···O1iv2.8400
O3···H1viii2.1800H4···F32.7800
N1···O3viii2.937 (3)H4A···N22.0900
N1···C203.424 (4)H4A···C162.5700
N1···C193.405 (4)H4A···H16B2.5600
N2···N42.553 (4)H4A···H16C2.3000
N2···O13.030 (4)H5···S1ix2.6400
N3···O12.841 (3)H7···C33x3.1000
N4···N22.553 (4)H7···O3viii2.8100
N5···S1ix3.287 (3)H7···H7Aviii2.4400
N6···N82.546 (3)H7A···H7viii2.4400
N6···O33.049 (3)H7A···O32.2200
N7···O32.863 (3)H7A···C182.5800
N8···N62.546 (3)H8···N62.0600
N2···H4A2.0900H8···H33C2.1300
N4···H16B2.7600H8···C332.3400
N4···H16C2.8100H8···H33B2.2500
N6···H212.9300H12···H16A2.3000
N6···H82.0600H12···F6vi2.4700
N8···H33B2.8300H15···S12.8700
N8···H33C2.7000H15···C92.9600
C1···C213.575 (5)H16A···H122.3000
C1···C29iv3.441 (5)H16A···F2vii2.7800
C1···C28iv3.578 (5)H16B···N42.7600
C2···C213.452 (5)H16B···H4A2.5600
C2···C30iv3.451 (5)H16B···S2iv3.0100
C2···C29iv3.494 (5)H16B···C32iv3.0900
C3···C223.600 (5)H16B···H32iv2.3400
C3···C213.599 (5)H16C···N42.8100
C3···C31iv3.576 (5)H16C···H4A2.3000
C3···C30iv3.211 (5)H21···F42.7700
C4···F33.030 (5)H21···F52.3800
C4···C30iv3.509 (5)H21···N62.9300
C4···Cl2iv3.499 (3)H21···C342.7200
C6···F13.142 (5)H24···C14ix3.0200
C7···C33x3.588 (5)H29···H33A2.3300
C8···C30iv3.500 (5)H29···H29ii2.5400
C8···C203.507 (5)H30···S1ii3.0000
C8···C253.600 (5)H32···S22.5700
C12···F6vi3.284 (6)H32···C262.8700
C15···S13.325 (3)H32···H16Biv2.3400
C18···C31iii3.454 (5)H33A···H292.3300
C18···C30iii3.459 (5)H33B···N82.8300
C18···O3viii2.976 (4)H33B···H82.2500
C18···C18viii3.471 (5)H33B···S2iii3.1300
C19···C31iii3.525 (5)H33C···O12.4000
C19···C32iii3.393 (5)H33C···N82.7000
C19···N13.405 (4)H33C···H32.5700
C20···C83.507 (5)H33C···H82.1300
C20···N13.424 (4)
C5—O2—C17117.6 (4)C11—C12—H12119.00
C22—O4—C34120.9 (4)C14—C13—H13120.00
C1—N1—C8111.3 (3)C12—C13—H13120.00
N3—N2—C2119.8 (3)C10—C15—H15121.00
N2—N3—C9118.9 (3)C14—C15—H15121.00
C9—N4—C10130.8 (3)C11—C16—H16A110.00
C1—N1—H1124.00H16A—C16—H16C109.00
C8—N1—H1124.00H16B—C16—H16C109.00
N2—N3—H3121.00H16A—C16—H16B110.00
C9—N3—H3121.00C11—C16—H16B109.00
C9—N4—H4A115.00C11—C16—H16C109.00
C10—N4—H4A115.00O3—C18—N5128.5 (3)
C18—N5—C25112.1 (3)O3—C18—C19126.3 (3)
N7—N6—C19119.3 (2)N5—C18—C19105.2 (3)
N6—N7—C26119.9 (2)N6—C19—C18129.8 (3)
C26—N8—C27133.7 (3)N6—C19—C20123.7 (3)
C25—N5—H5124.00C18—C19—C20106.5 (3)
C18—N5—H5124.00C19—C20—C25106.9 (3)
C26—N7—H7A120.00C19—C20—C21131.6 (3)
N6—N7—H7A120.00C21—C20—C25121.6 (3)
C27—N8—H8113.00C20—C21—C22116.9 (3)
C26—N8—H8113.00O4—C22—C21123.7 (4)
O1—C1—C2127.0 (3)C21—C22—C23122.3 (4)
N1—C1—C2105.4 (3)O4—C22—C23113.8 (3)
O1—C1—N1127.6 (3)C22—C23—C24121.0 (3)
N2—C2—C1128.5 (3)C23—C24—C25117.1 (4)
N2—C2—C3124.6 (3)N5—C25—C24129.9 (3)
C1—C2—C3106.9 (3)N5—C25—C20109.1 (3)
C2—C3—C4132.3 (3)C20—C25—C24121.0 (3)
C4—C3—C8121.1 (3)S2—C26—N8129.8 (3)
C2—C3—C8106.6 (3)S2—C26—N7118.1 (2)
C3—C4—C5117.1 (3)N7—C26—N8112.1 (3)
C4—C5—C6122.1 (3)C28—C27—C32121.1 (3)
O2—C5—C6118.8 (3)N8—C27—C28115.8 (3)
O2—C5—C4118.8 (3)N8—C27—C32123.1 (3)
C5—C6—C7120.7 (3)C27—C28—C33122.1 (3)
C6—C7—C8118.1 (3)C29—C28—C33121.0 (3)
N1—C8—C3109.9 (3)C27—C28—C29116.9 (3)
C3—C8—C7120.9 (3)C28—C29—C30123.1 (4)
N1—C8—C7129.3 (3)C29—C30—C31118.8 (3)
N3—C9—N4113.4 (3)C30—C31—C32121.3 (3)
S1—C9—N4128.0 (3)Cl2—C31—C32118.2 (3)
S1—C9—N3118.7 (2)Cl2—C31—C30120.5 (3)
N4—C10—C15121.9 (3)C27—C32—C31118.8 (3)
C11—C10—C15121.6 (3)F6—C34—O4111.7 (5)
N4—C10—C11116.4 (3)F4—C34—F5101.4 (5)
C10—C11—C12117.5 (4)F4—C34—F6107.2 (5)
C10—C11—C16122.6 (3)F4—C34—O4114.5 (6)
C12—C11—C16119.8 (4)F5—C34—F6107.1 (5)
C11—C12—C13122.1 (5)F5—C34—O4114.1 (5)
C12—C13—C14119.3 (5)C20—C21—H21122.00
Cl1—C14—C15119.8 (3)C22—C21—H21121.00
C13—C14—C15120.9 (4)C22—C23—H23119.00
Cl1—C14—C13119.3 (3)C24—C23—H23120.00
C10—C15—C14118.6 (4)C23—C24—H24121.00
F2—C17—O2109.5 (6)C25—C24—H24122.00
F3—C17—O2113.4 (6)C28—C29—H29118.00
F2—C17—F3108.2 (5)C30—C29—H29118.00
F1—C17—F3104.7 (6)C29—C30—H30121.00
F1—C17—O2112.9 (5)C31—C30—H30121.00
F1—C17—F2107.9 (5)C27—C32—H32121.00
C3—C4—H4121.00C31—C32—H32121.00
C5—C4—H4121.00C28—C33—H33A109.00
C5—C6—H6120.00C28—C33—H33B110.00
C7—C6—H6120.00C28—C33—H33C110.00
C6—C7—H7121.00H33A—C33—H33B109.00
C8—C7—H7121.00H33A—C33—H33C109.00
C13—C12—H12119.00H33B—C33—H33C109.00
C17—O2—C5—C487.7 (5)C4—C5—C6—C7−0.3 (5)
C17—O2—C5—C6−97.9 (5)O2—C5—C6—C7−174.6 (3)
C5—O2—C17—F159.2 (7)C5—C6—C7—C80.5 (5)
C5—O2—C17—F2179.4 (4)C6—C7—C8—N1178.0 (3)
C5—O2—C17—F3−59.7 (7)C6—C7—C8—C3−0.8 (5)
C22—O4—C34—F444.9 (6)C15—C10—C11—C12−1.1 (5)
C34—O4—C22—C2133.5 (7)N4—C10—C11—C160.2 (5)
C34—O4—C22—C23−150.4 (5)C11—C10—C15—C141.5 (5)
C22—O4—C34—F5−71.3 (7)C15—C10—C11—C16176.3 (3)
C22—O4—C34—F6167.1 (4)N4—C10—C15—C14177.4 (3)
C8—N1—C1—O1−177.9 (3)N4—C10—C11—C12−177.2 (3)
C8—N1—C1—C20.7 (3)C10—C11—C12—C13−0.5 (6)
C1—N1—C8—C3−0.2 (4)C16—C11—C12—C13−178.0 (4)
C1—N1—C8—C7−179.1 (3)C11—C12—C13—C141.7 (7)
N3—N2—C2—C3179.6 (3)C12—C13—C14—Cl1177.5 (4)
N3—N2—C2—C1−1.0 (5)C12—C13—C14—C15−1.3 (7)
C2—N2—N3—C9176.7 (3)Cl1—C14—C15—C10−179.1 (3)
N2—N3—C9—N42.9 (4)C13—C14—C15—C10−0.3 (6)
N2—N3—C9—S1−176.7 (2)O3—C18—C19—N6−6.6 (6)
C10—N4—C9—N3177.6 (3)O3—C18—C19—C20174.5 (3)
C9—N4—C10—C11−139.6 (4)N5—C18—C19—N6173.9 (3)
C10—N4—C9—S1−2.8 (6)N5—C18—C19—C20−5.0 (4)
C9—N4—C10—C1544.3 (6)N6—C19—C20—C215.1 (6)
C25—N5—C18—O3−175.1 (3)N6—C19—C20—C25−175.2 (3)
C25—N5—C18—C194.4 (4)C18—C19—C20—C21−176.0 (3)
C18—N5—C25—C20−2.2 (4)C18—C19—C20—C253.7 (4)
C18—N5—C25—C24177.6 (4)C19—C20—C21—C22179.2 (4)
C19—N6—N7—C26−179.3 (3)C25—C20—C21—C22−0.5 (5)
N7—N6—C19—C20178.4 (3)C19—C20—C25—N5−1.2 (4)
N7—N6—C19—C18−0.3 (5)C19—C20—C25—C24179.0 (3)
N6—N7—C26—N8−0.1 (4)C21—C20—C25—N5178.6 (3)
N6—N7—C26—S2−180.0 (2)C21—C20—C25—C24−1.2 (5)
C27—N8—C26—S21.5 (6)C20—C21—C22—O4177.0 (4)
C27—N8—C26—N7−178.3 (3)C20—C21—C22—C231.2 (6)
C26—N8—C27—C28−176.9 (3)O4—C22—C23—C24−176.6 (4)
C26—N8—C27—C323.9 (6)C21—C22—C23—C24−0.4 (7)
O1—C1—C2—N2−1.8 (6)C22—C23—C24—C25−1.3 (6)
O1—C1—C2—C3177.7 (3)C23—C24—C25—N5−177.7 (4)
N1—C1—C2—N2179.6 (3)C23—C24—C25—C202.0 (6)
N1—C1—C2—C3−1.0 (3)N8—C27—C28—C29−178.4 (3)
C1—C2—C3—C4178.2 (4)N8—C27—C28—C331.0 (5)
C1—C2—C3—C80.9 (4)C32—C27—C28—C290.8 (5)
N2—C2—C3—C8−179.6 (3)C32—C27—C28—C33−179.8 (3)
N2—C2—C3—C4−2.3 (6)N8—C27—C32—C31179.1 (3)
C2—C3—C8—N1−0.5 (4)C28—C27—C32—C31−0.1 (5)
C2—C3—C4—C5−177.6 (3)C27—C28—C29—C30−0.8 (5)
C8—C3—C4—C5−0.5 (5)C33—C28—C29—C30179.8 (3)
C4—C3—C8—C70.9 (5)C28—C29—C30—C310.1 (6)
C2—C3—C8—C7178.6 (3)C29—C30—C31—Cl2−178.3 (3)
C4—C3—C8—N1−178.2 (3)C29—C30—C31—C320.7 (5)
C3—C4—C5—O2174.5 (3)Cl2—C31—C32—C27178.3 (3)
C3—C4—C5—C60.3 (5)C30—C31—C32—C27−0.6 (5)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O3viii0.86002.18002.937 (3)147.00
N3—H3···O10.86002.21002.841 (3)131.00
N4—H4A···N20.86002.09002.553 (4)113.00
N5—H5···S1ix0.86002.64003.287 (3)133.00
N7—H7A···O30.86002.22002.863 (3)132.00
N8—H8···N60.86002.06002.546 (3)115.00
C12—H12···F6vi0.93002.47003.284 (6)147.00
C15—H15···S10.93002.87003.325 (3)111.00
C21—H21···F50.93002.38002.930 (5)118.00
C32—H32···S20.93002.57003.245 (4)130.00
C33—H33C···O10.96002.40003.355 (4)176.00

Symmetry codes: (viii) −x, −y+1, −z+1; (ix) x−1, y−1, z; (vi) −x+1, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2207).

References

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