









Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810014650/bq2207sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810014650/bq2207Isup2.hkl |
CCDC reference: 778054
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.051
- wR factor = 0.145
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O4 -- C34 .. 12.73 su PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C34
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 -- C17 .. 5.41 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 5 PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C18 .. 2.98 Ang. PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 7
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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.
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.
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.
For our work on 1H-indole-2,3-dione derivatives having pharmaceutical applications, see: Pervez et al. (2007, 2008, 2009a, 2010a). 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, 2010b). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
C17H12ClF3N4O2S | Z = 4 |
Mr = 428.82 | F(000) = 872 |
Triclinic, P1 | Dx = 1.552 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5808 (5) Å | Cell parameters from 6822 reflections |
b = 11.0262 (5) Å | θ = 2.1–25.5° |
c = 17.1743 (7) Å | µ = 0.37 mm−1 |
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 |
Bruker Kappa APEXII CCD diffractometer | 6822 independent reflections |
Radiation source: fine-focus sealed tube | 3927 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Detector resolution: 7.80 pixels mm-1 | θmax = 25.5°, θmin = 2.1° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −13→13 |
Tmin = 0.924, Tmax = 0.945 | l = −20→20 |
33611 measured reflections |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0588P)2 + 0.8346P] where P = (Fo2 + 2Fc2)/3 |
6822 reflections | (Δ/σ)max < 0.001 |
507 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C17H12ClF3N4O2S | γ = 107.814 (2)° |
Mr = 428.82 | V = 1834.96 (15) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.5808 (5) Å | Mo Kα radiation |
b = 11.0262 (5) Å | µ = 0.37 mm−1 |
c = 17.1743 (7) Å | T = 296 K |
α = 102.855 (3)° | 0.24 × 0.18 × 0.16 mm |
β = 94.766 (3)° |
Bruker Kappa APEXII CCD diffractometer | 6822 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3927 reflections with I > 2σ(I) |
Tmin = 0.924, Tmax = 0.945 | Rint = 0.049 |
33611 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.35 e Å−3 |
6822 reflections | Δρmin = −0.36 e Å−3 |
507 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.90141 (12) | 1.08034 (18) | 0.04378 (8) | 0.1311 (7) | |
S1 | 0.73013 (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) | |
O1 | 0.3721 (2) | 0.8851 (2) | 0.46034 (14) | 0.0616 (9) | |
O2 | −0.1786 (3) | 0.7545 (3) | 0.14412 (19) | 0.0825 (11) | |
N1 | 0.1403 (2) | 0.7922 (2) | 0.42522 (16) | 0.0498 (9) | |
N2 | 0.3438 (3) | 0.9308 (2) | 0.29315 (17) | 0.0503 (9) | |
N3 | 0.4732 (2) | 0.9813 (2) | 0.32968 (17) | 0.0522 (9) | |
N4 | 0.5207 (3) | 1.0337 (3) | 0.21286 (17) | 0.0585 (10) | |
C1 | 0.2674 (3) | 0.8546 (3) | 0.4138 (2) | 0.0494 (11) | |
C2 | 0.2519 (3) | 0.8751 (3) | 0.3308 (2) | 0.0472 (11) | |
C3 | 0.1102 (3) | 0.8184 (3) | 0.29786 (19) | 0.0455 (11) | |
C4 | 0.0382 (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) | |
C8 | 0.0459 (3) | 0.7697 (3) | 0.35726 (19) | 0.0457 (11) | |
C9 | 0.5704 (3) | 1.0342 (3) | 0.2870 (2) | 0.0504 (11) | |
C10 | 0.5856 (3) | 1.0824 (3) | 0.1519 (2) | 0.0552 (12) | |
C11 | 0.5210 (4) | 1.1454 (3) | 0.1090 (2) | 0.0644 (14) | |
C12 | 0.5790 (5) | 1.1884 (4) | 0.0471 (3) | 0.0876 (19) | |
C13 | 0.6963 (5) | 1.1717 (5) | 0.0280 (3) | 0.0936 (19) | |
C14 | 0.7571 (4) | 1.1069 (4) | 0.0704 (2) | 0.0796 (16) | |
C15 | 0.7029 (3) | 1.0613 (4) | 0.1325 (2) | 0.0666 (14) | |
C16 | 0.3887 (4) | 1.1624 (4) | 0.1257 (2) | 0.0859 (17) | |
C17 | −0.1989 (6) | 0.6580 (7) | 0.0794 (4) | 0.107 (3) | |
Cl2 | 0.91864 (10) | 0.86095 (10) | 0.77449 (6) | 0.0815 (4) | |
S2 | 0.40866 (10) | 0.58900 (11) | 0.67685 (6) | 0.0801 (4) | |
F4 | 0.4264 (4) | 0.5047 (4) | 0.1554 (2) | 0.1422 (17) | |
F5 | 0.4754 (3) | 0.7019 (3) | 0.2115 (2) | 0.1348 (14) | |
F6 | 0.4451 (3) | 0.6393 (4) | 0.08329 (19) | 0.1460 (16) | |
O3 | 0.0157 (2) | 0.3691 (2) | 0.47803 (14) | 0.0558 (8) | |
O4 | 0.2739 (4) | 0.5967 (4) | 0.1420 (2) | 0.1177 (16) | |
N5 | −0.0455 (3) | 0.3792 (3) | 0.34712 (17) | 0.0574 (10) | |
N6 | 0.2839 (2) | 0.5485 (2) | 0.45305 (15) | 0.0460 (9) | |
N7 | 0.2893 (2) | 0.5392 (2) | 0.52977 (15) | 0.0482 (9) | |
N8 | 0.5052 (2) | 0.6698 (3) | 0.54981 (16) | 0.0540 (9) | |
C18 | 0.0396 (3) | 0.4055 (3) | 0.4167 (2) | 0.0470 (11) | |
C19 | 0.1729 (3) | 0.4892 (3) | 0.40341 (18) | 0.0431 (10) | |
C20 | 0.1555 (3) | 0.4956 (3) | 0.32001 (19) | 0.0477 (11) | |
C21 | 0.2453 (3) | 0.5523 (3) | 0.2743 (2) | 0.0610 (12) | |
C22 | 0.1959 (4) | 0.5391 (4) | 0.1956 (2) | 0.0720 (16) | |
C23 | 0.0625 (5) | 0.4747 (4) | 0.1631 (2) | 0.0767 (16) | |
C24 | −0.0288 (4) | 0.4190 (4) | 0.2091 (2) | 0.0694 (12) | |
C25 | 0.0206 (3) | 0.4288 (3) | 0.2880 (2) | 0.0530 (11) | |
C26 | 0.4070 (3) | 0.6034 (3) | 0.58372 (18) | 0.0458 (10) | |
C27 | 0.6420 (3) | 0.7470 (3) | 0.5784 (2) | 0.0466 (10) | |
C28 | 0.7111 (3) | 0.8068 (3) | 0.5231 (2) | 0.0475 (11) | |
C29 | 0.8460 (3) | 0.8802 (3) | 0.5489 (3) | 0.0613 (14) | |
C30 | 0.9113 (3) | 0.8970 (3) | 0.6241 (3) | 0.0653 (14) | |
C31 | 0.8411 (3) | 0.8388 (3) | 0.6771 (2) | 0.0588 (14) | |
C32 | 0.7060 (3) | 0.7626 (3) | 0.6551 (2) | 0.0545 (11) | |
C33 | 0.6436 (3) | 0.7917 (3) | 0.4397 (2) | 0.0634 (14) | |
C34 | 0.3975 (7) | 0.6097 (6) | 0.1467 (3) | 0.104 (2) | |
H1 | 0.12071 | 0.76958 | 0.46871 | 0.0597* | |
H3 | 0.49461 | 0.98045 | 0.37892 | 0.0626* | |
H4 | 0.08074 | 0.84453 | 0.18566 | 0.0664* | |
H4A | 0.43479 | 0.99779 | 0.20002 | 0.0702* | |
H6 | −0.25734 | 0.66626 | 0.26341 | 0.0777* | |
H7 | −0.13535 | 0.67770 | 0.38442 | 0.0699* | |
H12 | 0.53705 | 1.23023 | 0.01730 | 0.1050* | |
H13 | 0.73471 | 1.20383 | −0.01326 | 0.1123* | |
H15 | 0.74409 | 1.01713 | 0.16095 | 0.0798* | |
H16A | 0.36321 | 1.21142 | 0.09122 | 0.1291* | |
H16B | 0.39812 | 1.20921 | 0.18129 | 0.1291* | |
H16C | 0.32068 | 1.07722 | 0.11524 | 0.1291* | |
H5 | −0.13038 | 0.33675 | 0.34011 | 0.0688* | |
H7A | 0.21924 | 0.49298 | 0.54511 | 0.0579* | |
H8 | 0.47995 | 0.66451 | 0.49991 | 0.0648* | |
H21 | 0.33551 | 0.59747 | 0.29581 | 0.0737* | |
H23 | 0.03314 | 0.46849 | 0.10931 | 0.0919* | |
H24 | −0.11948 | 0.37683 | 0.18770 | 0.0829* | |
H29 | 0.89418 | 0.91994 | 0.51308 | 0.0734* | |
H30 | 1.00208 | 0.94708 | 0.63931 | 0.0786* | |
H32 | 0.65949 | 0.72279 | 0.69143 | 0.0653* | |
H33A | 0.70436 | 0.84749 | 0.41352 | 0.0949* | |
H33B | 0.61878 | 0.70148 | 0.40892 | 0.0949* | |
H33C | 0.56448 | 0.81664 | 0.44308 | 0.0949* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0695 (8) | 0.2284 (17) | 0.0752 (8) | 0.0309 (9) | 0.0249 (6) | 0.0215 (9) |
S1 | 0.0366 (5) | 0.0842 (7) | 0.0749 (7) | 0.0045 (4) | 0.0044 (4) | 0.0380 (5) |
F1 | 0.236 (4) | 0.099 (2) | 0.140 (3) | −0.011 (3) | −0.058 (3) | 0.019 (2) |
F2 | 0.142 (3) | 0.175 (3) | 0.095 (2) | 0.045 (2) | −0.042 (2) | 0.035 (2) |
F3 | 0.154 (3) | 0.267 (5) | 0.086 (2) | 0.105 (3) | 0.011 (2) | 0.010 (2) |
O1 | 0.0414 (13) | 0.0727 (16) | 0.0665 (16) | 0.0138 (12) | 0.0039 (12) | 0.0189 (12) |
O2 | 0.0667 (18) | 0.093 (2) | 0.082 (2) | 0.0219 (15) | −0.0078 (16) | 0.0253 (17) |
N1 | 0.0394 (15) | 0.0537 (16) | 0.0560 (18) | 0.0107 (12) | 0.0131 (13) | 0.0189 (13) |
N2 | 0.0359 (15) | 0.0474 (15) | 0.0676 (18) | 0.0107 (12) | 0.0108 (13) | 0.0187 (14) |
N3 | 0.0374 (15) | 0.0556 (16) | 0.0633 (18) | 0.0077 (12) | 0.0101 (13) | 0.0254 (14) |
N4 | 0.0346 (14) | 0.0734 (19) | 0.0626 (19) | 0.0031 (13) | 0.0038 (14) | 0.0303 (15) |
C1 | 0.044 (2) | 0.0438 (18) | 0.061 (2) | 0.0150 (15) | 0.0143 (17) | 0.0126 (16) |
C2 | 0.0379 (18) | 0.0396 (17) | 0.064 (2) | 0.0102 (14) | 0.0147 (16) | 0.0149 (15) |
C3 | 0.0398 (18) | 0.0387 (17) | 0.056 (2) | 0.0107 (14) | 0.0100 (16) | 0.0113 (15) |
C4 | 0.052 (2) | 0.051 (2) | 0.064 (2) | 0.0149 (16) | 0.0162 (18) | 0.0184 (17) |
C5 | 0.045 (2) | 0.062 (2) | 0.071 (3) | 0.0138 (17) | −0.0010 (18) | 0.0194 (19) |
C6 | 0.0373 (19) | 0.069 (2) | 0.084 (3) | 0.0099 (17) | 0.0101 (19) | 0.024 (2) |
C7 | 0.0380 (19) | 0.064 (2) | 0.074 (3) | 0.0087 (16) | 0.0152 (18) | 0.0275 (19) |
C8 | 0.0402 (18) | 0.0387 (17) | 0.058 (2) | 0.0120 (14) | 0.0141 (16) | 0.0119 (15) |
C9 | 0.0404 (18) | 0.0454 (18) | 0.065 (2) | 0.0081 (15) | 0.0110 (16) | 0.0216 (16) |
C10 | 0.050 (2) | 0.057 (2) | 0.047 (2) | 0.0020 (16) | −0.0002 (16) | 0.0159 (17) |
C11 | 0.078 (3) | 0.057 (2) | 0.047 (2) | 0.0118 (19) | −0.0008 (19) | 0.0103 (17) |
C12 | 0.118 (4) | 0.088 (3) | 0.058 (3) | 0.030 (3) | 0.011 (3) | 0.029 (2) |
C13 | 0.108 (4) | 0.097 (3) | 0.053 (3) | −0.003 (3) | 0.015 (3) | 0.026 (2) |
C14 | 0.058 (2) | 0.099 (3) | 0.056 (3) | −0.002 (2) | 0.009 (2) | 0.009 (2) |
C15 | 0.050 (2) | 0.084 (3) | 0.058 (2) | 0.0109 (19) | 0.0067 (18) | 0.020 (2) |
C16 | 0.098 (3) | 0.104 (3) | 0.066 (3) | 0.055 (3) | −0.001 (2) | 0.018 (2) |
C17 | 0.087 (4) | 0.135 (5) | 0.085 (4) | 0.023 (4) | −0.011 (3) | 0.033 (4) |
Cl2 | 0.0671 (6) | 0.0745 (7) | 0.0856 (7) | 0.0259 (5) | −0.0283 (5) | −0.0016 (5) |
S2 | 0.0708 (7) | 0.0896 (7) | 0.0513 (6) | −0.0154 (5) | −0.0063 (5) | 0.0270 (5) |
F4 | 0.186 (3) | 0.154 (3) | 0.144 (3) | 0.096 (3) | 0.083 (2) | 0.077 (2) |
F5 | 0.138 (3) | 0.127 (2) | 0.110 (2) | 0.001 (2) | 0.033 (2) | 0.029 (2) |
F6 | 0.164 (3) | 0.208 (3) | 0.106 (2) | 0.065 (3) | 0.065 (2) | 0.101 (2) |
O3 | 0.0511 (13) | 0.0498 (13) | 0.0574 (15) | 0.0047 (10) | 0.0092 (11) | 0.0128 (11) |
O4 | 0.094 (2) | 0.195 (4) | 0.086 (2) | 0.048 (3) | 0.019 (2) | 0.079 (2) |
N5 | 0.0376 (15) | 0.0573 (17) | 0.0593 (19) | 0.0010 (13) | −0.0052 (14) | 0.0053 (14) |
N6 | 0.0423 (15) | 0.0445 (15) | 0.0426 (16) | 0.0062 (12) | 0.0007 (12) | 0.0082 (12) |
N7 | 0.0407 (15) | 0.0456 (15) | 0.0450 (16) | −0.0020 (12) | 0.0001 (12) | 0.0108 (12) |
N8 | 0.0378 (15) | 0.0667 (18) | 0.0464 (16) | 0.0001 (13) | −0.0026 (12) | 0.0205 (14) |
C18 | 0.0428 (19) | 0.0360 (17) | 0.054 (2) | 0.0095 (14) | 0.0022 (16) | 0.0027 (15) |
C19 | 0.0413 (18) | 0.0376 (16) | 0.0441 (19) | 0.0080 (14) | 0.0017 (14) | 0.0072 (14) |
C20 | 0.0481 (19) | 0.0413 (18) | 0.048 (2) | 0.0113 (15) | 0.0013 (16) | 0.0076 (14) |
C21 | 0.055 (2) | 0.071 (2) | 0.053 (2) | 0.0143 (18) | −0.0011 (18) | 0.0215 (18) |
C22 | 0.077 (3) | 0.090 (3) | 0.056 (2) | 0.030 (2) | 0.011 (2) | 0.030 (2) |
C23 | 0.093 (3) | 0.091 (3) | 0.047 (2) | 0.036 (3) | −0.007 (2) | 0.019 (2) |
C24 | 0.066 (2) | 0.069 (2) | 0.058 (2) | 0.019 (2) | −0.015 (2) | 0.0007 (19) |
C25 | 0.051 (2) | 0.0454 (19) | 0.050 (2) | 0.0111 (16) | −0.0055 (17) | −0.0003 (16) |
C26 | 0.0430 (18) | 0.0397 (17) | 0.0457 (19) | 0.0050 (14) | −0.0019 (15) | 0.0088 (14) |
C27 | 0.0359 (17) | 0.0374 (17) | 0.061 (2) | 0.0091 (14) | −0.0010 (16) | 0.0095 (15) |
C28 | 0.0397 (18) | 0.0409 (17) | 0.063 (2) | 0.0167 (14) | 0.0095 (16) | 0.0111 (15) |
C29 | 0.041 (2) | 0.049 (2) | 0.092 (3) | 0.0141 (16) | 0.015 (2) | 0.0147 (19) |
C30 | 0.0362 (19) | 0.051 (2) | 0.097 (3) | 0.0117 (16) | 0.003 (2) | 0.003 (2) |
C31 | 0.046 (2) | 0.0453 (19) | 0.075 (3) | 0.0206 (17) | −0.0128 (18) | −0.0033 (17) |
C32 | 0.047 (2) | 0.0478 (19) | 0.060 (2) | 0.0107 (16) | −0.0034 (17) | 0.0084 (16) |
C33 | 0.052 (2) | 0.072 (2) | 0.075 (3) | 0.0215 (18) | 0.0204 (19) | 0.032 (2) |
C34 | 0.146 (5) | 0.105 (4) | 0.064 (3) | 0.029 (4) | 0.026 (4) | 0.044 (3) |
Cl1—C14 | 1.719 (5) | C6—C7 | 1.374 (5) |
Cl2—C31 | 1.732 (3) | C7—C8 | 1.381 (5) |
S1—C9 | 1.656 (3) | C10—C15 | 1.384 (5) |
S2—C26 | 1.641 (3) | C10—C11 | 1.388 (5) |
F1—C17 | 1.296 (8) | C11—C12 | 1.373 (6) |
F2—C17 | 1.304 (7) | C11—C16 | 1.510 (6) |
F3—C17 | 1.311 (8) | C12—C13 | 1.365 (8) |
F4—C34 | 1.320 (8) | C13—C14 | 1.375 (7) |
F5—C34 | 1.335 (7) | C14—C15 | 1.372 (5) |
F6—C34 | 1.302 (7) | C4—H4 | 0.9300 |
O1—C1 | 1.218 (4) | C6—H6 | 0.9300 |
O2—C5 | 1.416 (5) | C7—H7 | 0.9300 |
O2—C17 | 1.307 (8) | C12—H12 | 0.9300 |
O3—C18 | 1.227 (4) | C13—H13 | 0.9300 |
O4—C22 | 1.413 (6) | C15—H15 | 0.9300 |
O4—C34 | 1.265 (9) | C16—H16A | 0.9600 |
N1—C8 | 1.396 (4) | C16—H16C | 0.9600 |
N1—C1 | 1.363 (4) | C16—H16B | 0.9600 |
N2—N3 | 1.347 (4) | C18—C19 | 1.498 (5) |
N2—C2 | 1.287 (4) | C19—C20 | 1.449 (4) |
N3—C9 | 1.373 (4) | C20—C21 | 1.374 (5) |
N4—C9 | 1.335 (4) | C20—C25 | 1.389 (5) |
N4—C10 | 1.414 (4) | C21—C22 | 1.367 (5) |
N1—H1 | 0.8600 | C22—C23 | 1.374 (7) |
N3—H3 | 0.8600 | C23—C24 | 1.384 (6) |
N4—H4A | 0.8600 | C24—C25 | 1.380 (5) |
N5—C25 | 1.397 (5) | C27—C28 | 1.404 (5) |
N5—C18 | 1.353 (4) | C27—C32 | 1.380 (5) |
N6—C19 | 1.284 (4) | C28—C33 | 1.497 (5) |
N6—N7 | 1.342 (3) | C28—C29 | 1.385 (5) |
N7—C26 | 1.374 (4) | C29—C30 | 1.359 (7) |
N8—C27 | 1.415 (4) | C30—C31 | 1.369 (5) |
N8—C26 | 1.334 (4) | C31—C32 | 1.388 (5) |
N5—H5 | 0.8600 | C21—H21 | 0.9300 |
N7—H7A | 0.8600 | C23—H23 | 0.9300 |
N8—H8 | 0.8600 | C24—H24 | 0.9300 |
C1—C2 | 1.496 (5) | C29—H29 | 0.9300 |
C2—C3 | 1.445 (5) | C30—H30 | 0.9300 |
C3—C8 | 1.388 (5) | C32—H32 | 0.9300 |
C3—C4 | 1.377 (5) | C33—H33A | 0.9600 |
C4—C5 | 1.383 (5) | C33—H33B | 0.9600 |
C5—C6 | 1.370 (5) | C33—H33C | 0.9600 |
Cl1···Cl1i | 3.369 (2) | C21···F4 | 2.984 (5) |
Cl1···Cl2ii | 3.3384 (17) | C21···C3 | 3.599 (5) |
Cl2···C25iii | 3.409 (3) | C21···C2 | 3.452 (5) |
Cl2···C4iv | 3.499 (3) | C21···F5 | 2.930 (5) |
Cl2···Cl1ii | 3.3384 (17) | C21···C1 | 3.575 (5) |
S1···N5v | 3.287 (3) | C22···C3 | 3.600 (5) |
S1···C15 | 3.325 (3) | C25···Cl2iii | 3.409 (3) |
S2···C32 | 3.245 (4) | C25···C8 | 3.600 (5) |
S1···H15 | 2.8700 | C28···C1iv | 3.578 (5) |
S1···H30ii | 3.0000 | C29···C2iv | 3.494 (5) |
S1···H5v | 2.6400 | C29···C1iv | 3.441 (5) |
S2···H33Biii | 3.1300 | C30···O3iii | 3.406 (4) |
S2···H32 | 2.5700 | C30···C2iv | 3.451 (5) |
S2···H16Biv | 3.0100 | C30···C4iv | 3.509 (5) |
F1···C6 | 3.142 (5) | C30···C18iii | 3.459 (5) |
F3···C4 | 3.030 (5) | C30···C8iv | 3.500 (5) |
F4···C21 | 2.984 (5) | C30···C3iv | 3.211 (5) |
F5···C21 | 2.930 (5) | C31···C3iv | 3.576 (5) |
F6···C12vi | 3.284 (6) | C31···C19iii | 3.525 (5) |
F2···H16Avii | 2.7800 | C31···C18iii | 3.454 (5) |
F3···H4 | 2.7800 | C32···C19iii | 3.393 (5) |
F4···H21 | 2.7700 | C32···S2 | 3.245 (4) |
F5···H21 | 2.3800 | C33···O1 | 3.355 (4) |
F6···H12vi | 2.4700 | C33···C7xi | 3.588 (5) |
O1···C33 | 3.355 (4) | C1···H3 | 2.5800 |
O1···N3 | 2.841 (3) | C9···H15 | 2.9600 |
O1···N2 | 3.030 (4) | C14···H24v | 3.0200 |
O1···O1iv | 3.043 (3) | C16···H4A | 2.5700 |
O3···N6 | 3.049 (3) | C18···H7A | 2.5800 |
O3···N1viii | 2.937 (3) | C26···H32 | 2.8700 |
O3···N7 | 2.863 (3) | C32···H16Biv | 3.0900 |
O3···O3viii | 2.945 (3) | C33···H7xi | 3.1000 |
O3···C18viii | 2.976 (4) | C33···H8 | 2.3400 |
O3···C30iii | 3.406 (4) | C34···H21 | 2.7200 |
O1···H3 | 2.2100 | H1···O3viii | 2.1800 |
O1···H33C | 2.4000 | H3···H33C | 2.5700 |
O1···H3iv | 2.8400 | H3···C1 | 2.5800 |
O3···H7A | 2.2200 | H3···O1 | 2.2100 |
O3···H7viii | 2.8100 | H3···O1iv | 2.8400 |
O3···H1viii | 2.1800 | H4···F3 | 2.7800 |
N1···O3viii | 2.937 (3) | H4A···N2 | 2.0900 |
N1···C20 | 3.424 (4) | H4A···C16 | 2.5700 |
N1···C19 | 3.405 (4) | H4A···H16B | 2.5600 |
N2···N4 | 2.553 (4) | H4A···H16C | 2.3000 |
N2···O1 | 3.030 (4) | H5···S1ix | 2.6400 |
N3···O1 | 2.841 (3) | H7···C33x | 3.1000 |
N4···N2 | 2.553 (4) | H7···O3viii | 2.8100 |
N5···S1ix | 3.287 (3) | H7···H7Aviii | 2.4400 |
N6···N8 | 2.546 (3) | H7A···H7viii | 2.4400 |
N6···O3 | 3.049 (3) | H7A···O3 | 2.2200 |
N7···O3 | 2.863 (3) | H7A···C18 | 2.5800 |
N8···N6 | 2.546 (3) | H8···N6 | 2.0600 |
N2···H4A | 2.0900 | H8···H33C | 2.1300 |
N4···H16B | 2.7600 | H8···C33 | 2.3400 |
N4···H16C | 2.8100 | H8···H33B | 2.2500 |
N6···H21 | 2.9300 | H12···H16A | 2.3000 |
N6···H8 | 2.0600 | H12···F6vi | 2.4700 |
N8···H33B | 2.8300 | H15···S1 | 2.8700 |
N8···H33C | 2.7000 | H15···C9 | 2.9600 |
C1···C21 | 3.575 (5) | H16A···H12 | 2.3000 |
C1···C29iv | 3.441 (5) | H16A···F2vii | 2.7800 |
C1···C28iv | 3.578 (5) | H16B···N4 | 2.7600 |
C2···C21 | 3.452 (5) | H16B···H4A | 2.5600 |
C2···C30iv | 3.451 (5) | H16B···S2iv | 3.0100 |
C2···C29iv | 3.494 (5) | H16B···C32iv | 3.0900 |
C3···C22 | 3.600 (5) | H16B···H32iv | 2.3400 |
C3···C21 | 3.599 (5) | H16C···N4 | 2.8100 |
C3···C31iv | 3.576 (5) | H16C···H4A | 2.3000 |
C3···C30iv | 3.211 (5) | H21···F4 | 2.7700 |
C4···F3 | 3.030 (5) | H21···F5 | 2.3800 |
C4···C30iv | 3.509 (5) | H21···N6 | 2.9300 |
C4···Cl2iv | 3.499 (3) | H21···C34 | 2.7200 |
C6···F1 | 3.142 (5) | H24···C14ix | 3.0200 |
C7···C33x | 3.588 (5) | H29···H33A | 2.3300 |
C8···C30iv | 3.500 (5) | H29···H29ii | 2.5400 |
C8···C20 | 3.507 (5) | H30···S1ii | 3.0000 |
C8···C25 | 3.600 (5) | H32···S2 | 2.5700 |
C12···F6vi | 3.284 (6) | H32···C26 | 2.8700 |
C15···S1 | 3.325 (3) | H32···H16Biv | 2.3400 |
C18···C31iii | 3.454 (5) | H33A···H29 | 2.3300 |
C18···C30iii | 3.459 (5) | H33B···N8 | 2.8300 |
C18···O3viii | 2.976 (4) | H33B···H8 | 2.2500 |
C18···C18viii | 3.471 (5) | H33B···S2iii | 3.1300 |
C19···C31iii | 3.525 (5) | H33C···O1 | 2.4000 |
C19···C32iii | 3.393 (5) | H33C···N8 | 2.7000 |
C19···N1 | 3.405 (4) | H33C···H3 | 2.5700 |
C20···C8 | 3.507 (5) | H33C···H8 | 2.1300 |
C20···N1 | 3.424 (4) | ||
C5—O2—C17 | 117.6 (4) | C11—C12—H12 | 119.00 |
C22—O4—C34 | 120.9 (4) | C14—C13—H13 | 120.00 |
C1—N1—C8 | 111.3 (3) | C12—C13—H13 | 120.00 |
N3—N2—C2 | 119.8 (3) | C10—C15—H15 | 121.00 |
N2—N3—C9 | 118.9 (3) | C14—C15—H15 | 121.00 |
C9—N4—C10 | 130.8 (3) | C11—C16—H16A | 110.00 |
C1—N1—H1 | 124.00 | H16A—C16—H16C | 109.00 |
C8—N1—H1 | 124.00 | H16B—C16—H16C | 109.00 |
N2—N3—H3 | 121.00 | H16A—C16—H16B | 110.00 |
C9—N3—H3 | 121.00 | C11—C16—H16B | 109.00 |
C9—N4—H4A | 115.00 | C11—C16—H16C | 109.00 |
C10—N4—H4A | 115.00 | O3—C18—N5 | 128.5 (3) |
C18—N5—C25 | 112.1 (3) | O3—C18—C19 | 126.3 (3) |
N7—N6—C19 | 119.3 (2) | N5—C18—C19 | 105.2 (3) |
N6—N7—C26 | 119.9 (2) | N6—C19—C18 | 129.8 (3) |
C26—N8—C27 | 133.7 (3) | N6—C19—C20 | 123.7 (3) |
C25—N5—H5 | 124.00 | C18—C19—C20 | 106.5 (3) |
C18—N5—H5 | 124.00 | C19—C20—C25 | 106.9 (3) |
C26—N7—H7A | 120.00 | C19—C20—C21 | 131.6 (3) |
N6—N7—H7A | 120.00 | C21—C20—C25 | 121.6 (3) |
C27—N8—H8 | 113.00 | C20—C21—C22 | 116.9 (3) |
C26—N8—H8 | 113.00 | O4—C22—C21 | 123.7 (4) |
O1—C1—C2 | 127.0 (3) | C21—C22—C23 | 122.3 (4) |
N1—C1—C2 | 105.4 (3) | O4—C22—C23 | 113.8 (3) |
O1—C1—N1 | 127.6 (3) | C22—C23—C24 | 121.0 (3) |
N2—C2—C1 | 128.5 (3) | C23—C24—C25 | 117.1 (4) |
N2—C2—C3 | 124.6 (3) | N5—C25—C24 | 129.9 (3) |
C1—C2—C3 | 106.9 (3) | N5—C25—C20 | 109.1 (3) |
C2—C3—C4 | 132.3 (3) | C20—C25—C24 | 121.0 (3) |
C4—C3—C8 | 121.1 (3) | S2—C26—N8 | 129.8 (3) |
C2—C3—C8 | 106.6 (3) | S2—C26—N7 | 118.1 (2) |
C3—C4—C5 | 117.1 (3) | N7—C26—N8 | 112.1 (3) |
C4—C5—C6 | 122.1 (3) | C28—C27—C32 | 121.1 (3) |
O2—C5—C6 | 118.8 (3) | N8—C27—C28 | 115.8 (3) |
O2—C5—C4 | 118.8 (3) | N8—C27—C32 | 123.1 (3) |
C5—C6—C7 | 120.7 (3) | C27—C28—C33 | 122.1 (3) |
C6—C7—C8 | 118.1 (3) | C29—C28—C33 | 121.0 (3) |
N1—C8—C3 | 109.9 (3) | C27—C28—C29 | 116.9 (3) |
C3—C8—C7 | 120.9 (3) | C28—C29—C30 | 123.1 (4) |
N1—C8—C7 | 129.3 (3) | C29—C30—C31 | 118.8 (3) |
N3—C9—N4 | 113.4 (3) | C30—C31—C32 | 121.3 (3) |
S1—C9—N4 | 128.0 (3) | Cl2—C31—C32 | 118.2 (3) |
S1—C9—N3 | 118.7 (2) | Cl2—C31—C30 | 120.5 (3) |
N4—C10—C15 | 121.9 (3) | C27—C32—C31 | 118.8 (3) |
C11—C10—C15 | 121.6 (3) | F6—C34—O4 | 111.7 (5) |
N4—C10—C11 | 116.4 (3) | F4—C34—F5 | 101.4 (5) |
C10—C11—C12 | 117.5 (4) | F4—C34—F6 | 107.2 (5) |
C10—C11—C16 | 122.6 (3) | F4—C34—O4 | 114.5 (6) |
C12—C11—C16 | 119.8 (4) | F5—C34—F6 | 107.1 (5) |
C11—C12—C13 | 122.1 (5) | F5—C34—O4 | 114.1 (5) |
C12—C13—C14 | 119.3 (5) | C20—C21—H21 | 122.00 |
Cl1—C14—C15 | 119.8 (3) | C22—C21—H21 | 121.00 |
C13—C14—C15 | 120.9 (4) | C22—C23—H23 | 119.00 |
Cl1—C14—C13 | 119.3 (3) | C24—C23—H23 | 120.00 |
C10—C15—C14 | 118.6 (4) | C23—C24—H24 | 121.00 |
F2—C17—O2 | 109.5 (6) | C25—C24—H24 | 122.00 |
F3—C17—O2 | 113.4 (6) | C28—C29—H29 | 118.00 |
F2—C17—F3 | 108.2 (5) | C30—C29—H29 | 118.00 |
F1—C17—F3 | 104.7 (6) | C29—C30—H30 | 121.00 |
F1—C17—O2 | 112.9 (5) | C31—C30—H30 | 121.00 |
F1—C17—F2 | 107.9 (5) | C27—C32—H32 | 121.00 |
C3—C4—H4 | 121.00 | C31—C32—H32 | 121.00 |
C5—C4—H4 | 121.00 | C28—C33—H33A | 109.00 |
C5—C6—H6 | 120.00 | C28—C33—H33B | 110.00 |
C7—C6—H6 | 120.00 | C28—C33—H33C | 110.00 |
C6—C7—H7 | 121.00 | H33A—C33—H33B | 109.00 |
C8—C7—H7 | 121.00 | H33A—C33—H33C | 109.00 |
C13—C12—H12 | 119.00 | H33B—C33—H33C | 109.00 |
C17—O2—C5—C4 | 87.7 (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—F1 | 59.2 (7) | C5—C6—C7—C8 | 0.5 (5) |
C5—O2—C17—F2 | 179.4 (4) | C6—C7—C8—N1 | 178.0 (3) |
C5—O2—C17—F3 | −59.7 (7) | C6—C7—C8—C3 | −0.8 (5) |
C22—O4—C34—F4 | 44.9 (6) | C15—C10—C11—C12 | −1.1 (5) |
C34—O4—C22—C21 | 33.5 (7) | N4—C10—C11—C16 | 0.2 (5) |
C34—O4—C22—C23 | −150.4 (5) | C11—C10—C15—C14 | 1.5 (5) |
C22—O4—C34—F5 | −71.3 (7) | C15—C10—C11—C16 | 176.3 (3) |
C22—O4—C34—F6 | 167.1 (4) | N4—C10—C15—C14 | 177.4 (3) |
C8—N1—C1—O1 | −177.9 (3) | N4—C10—C11—C12 | −177.2 (3) |
C8—N1—C1—C2 | 0.7 (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—C14 | 1.7 (7) |
N3—N2—C2—C3 | 179.6 (3) | C12—C13—C14—Cl1 | 177.5 (4) |
N3—N2—C2—C1 | −1.0 (5) | C12—C13—C14—C15 | −1.3 (7) |
C2—N2—N3—C9 | 176.7 (3) | Cl1—C14—C15—C10 | −179.1 (3) |
N2—N3—C9—N4 | 2.9 (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—N3 | 177.6 (3) | O3—C18—C19—C20 | 174.5 (3) |
C9—N4—C10—C11 | −139.6 (4) | N5—C18—C19—N6 | 173.9 (3) |
C10—N4—C9—S1 | −2.8 (6) | N5—C18—C19—C20 | −5.0 (4) |
C9—N4—C10—C15 | 44.3 (6) | N6—C19—C20—C21 | 5.1 (6) |
C25—N5—C18—O3 | −175.1 (3) | N6—C19—C20—C25 | −175.2 (3) |
C25—N5—C18—C19 | 4.4 (4) | C18—C19—C20—C21 | −176.0 (3) |
C18—N5—C25—C20 | −2.2 (4) | C18—C19—C20—C25 | 3.7 (4) |
C18—N5—C25—C24 | 177.6 (4) | C19—C20—C21—C22 | 179.2 (4) |
C19—N6—N7—C26 | −179.3 (3) | C25—C20—C21—C22 | −0.5 (5) |
N7—N6—C19—C20 | 178.4 (3) | C19—C20—C25—N5 | −1.2 (4) |
N7—N6—C19—C18 | −0.3 (5) | C19—C20—C25—C24 | 179.0 (3) |
N6—N7—C26—N8 | −0.1 (4) | C21—C20—C25—N5 | 178.6 (3) |
N6—N7—C26—S2 | −180.0 (2) | C21—C20—C25—C24 | −1.2 (5) |
C27—N8—C26—S2 | 1.5 (6) | C20—C21—C22—O4 | 177.0 (4) |
C27—N8—C26—N7 | −178.3 (3) | C20—C21—C22—C23 | 1.2 (6) |
C26—N8—C27—C28 | −176.9 (3) | O4—C22—C23—C24 | −176.6 (4) |
C26—N8—C27—C32 | 3.9 (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—C3 | 177.7 (3) | C23—C24—C25—N5 | −177.7 (4) |
N1—C1—C2—N2 | 179.6 (3) | C23—C24—C25—C20 | 2.0 (6) |
N1—C1—C2—C3 | −1.0 (3) | N8—C27—C28—C29 | −178.4 (3) |
C1—C2—C3—C4 | 178.2 (4) | N8—C27—C28—C33 | 1.0 (5) |
C1—C2—C3—C8 | 0.9 (4) | C32—C27—C28—C29 | 0.8 (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—C31 | 179.1 (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—C30 | 179.8 (3) |
C4—C3—C8—C7 | 0.9 (5) | C28—C29—C30—C31 | 0.1 (6) |
C2—C3—C8—C7 | 178.6 (3) | C29—C30—C31—Cl2 | −178.3 (3) |
C4—C3—C8—N1 | −178.2 (3) | C29—C30—C31—C32 | 0.7 (5) |
C3—C4—C5—O2 | 174.5 (3) | Cl2—C31—C32—C27 | 178.3 (3) |
C3—C4—C5—C6 | 0.3 (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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3viii | 0.8600 | 2.1800 | 2.937 (3) | 147.00 |
N3—H3···O1 | 0.8600 | 2.2100 | 2.841 (3) | 131.00 |
N4—H4A···N2 | 0.8600 | 2.0900 | 2.553 (4) | 113.00 |
N5—H5···S1ix | 0.8600 | 2.6400 | 3.287 (3) | 133.00 |
N7—H7A···O3 | 0.8600 | 2.2200 | 2.863 (3) | 132.00 |
N8—H8···N6 | 0.8600 | 2.0600 | 2.546 (3) | 115.00 |
C12—H12···F6vi | 0.9300 | 2.4700 | 3.284 (6) | 147.00 |
C15—H15···S1 | 0.9300 | 2.8700 | 3.325 (3) | 111.00 |
C21—H21···F5 | 0.9300 | 2.3800 | 2.930 (5) | 118.00 |
C32—H32···S2 | 0.9300 | 2.5700 | 3.245 (4) | 130.00 |
C33—H33C···O1 | 0.9600 | 2.4000 | 3.355 (4) | 176.00 |
Symmetry codes: (vi) −x+1, −y+2, −z; (viii) −x, −y+1, −z+1; (ix) x−1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C17H12ClF3N4O2S |
Mr | 428.82 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 10.5808 (5), 11.0262 (5), 17.1743 (7) |
α, β, γ (°) | 102.855 (3), 94.766 (3), 107.814 (2) |
V (Å3) | 1834.96 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.37 |
Crystal size (mm) | 0.24 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.924, 0.945 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33611, 6822, 3927 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.145, 1.02 |
No. of reflections | 6822 |
No. of parameters | 507 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.36 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.8600 | 2.1800 | 2.937 (3) | 147.00 |
N3—H3···O1 | 0.8600 | 2.2100 | 2.841 (3) | 131.00 |
N4—H4A···N2 | 0.8600 | 2.0900 | 2.553 (4) | 113.00 |
N5—H5···S1ii | 0.8600 | 2.6400 | 3.287 (3) | 133.00 |
N7—H7A···O3 | 0.8600 | 2.2200 | 2.863 (3) | 132.00 |
N8—H8···N6 | 0.8600 | 2.0600 | 2.546 (3) | 115.00 |
C12—H12···F6iii | 0.9300 | 2.4700 | 3.284 (6) | 147.00 |
C15—H15···S1 | 0.9300 | 2.8700 | 3.325 (3) | 111.00 |
C21—H21···F5 | 0.9300 | 2.3800 | 2.930 (5) | 118.00 |
C32—H32···S2 | 0.9300 | 2.5700 | 3.245 (4) | 130.00 |
C33—H33C···O1 | 0.9600 | 2.4000 | 3.355 (4) | 176.00 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y−1, z; (iii) −x+1, −y+2, −z. |
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.