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There are two mol­ecules in the asymmetric unit of the title compound, C11H6ClF3N4O2S. The urea linkage in each mol­ecules is essentially planar due to the presence of intra­molecular N—H...O hydrogen bonds. The crystal structure is stabilized by several inter­molecular hydrogen bonds, of both the classical NH-donor type and the non-classical CH-donor type.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806025049/gh2008sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806025049/gh2008Isup2.hkl
Contains datablock I

CCDC reference: 618200

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.043
  • wR factor = 0.115
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C22
Alert level C PLAT213_ALERT_2_C Atom F6' has ADP max/min Ratio ............. 3.30 prolat PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.33 PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc. PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ? PLAT414_ALERT_2_C Short Intra D-H..H-X H4A .. H5 .. 1.98 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. F6' .. 3.24 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A .. F5 .. 2.66 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 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 8 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.

1-(4-Bromobenzoyl)-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)urea top
Crystal data top
C11H6BrF3N4O2SF(000) = 1552
Mr = 395.17Dx = 1.874 Mg m3
Monoclinic, P21/nMelting point: 511 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 11.8573 (12) ÅCell parameters from 5341 reflections
b = 13.7774 (13) Åθ = 2.3–25.2°
c = 17.3795 (17) ŵ = 3.13 mm1
β = 99.396 (2)°T = 292 K
V = 2801.1 (5) Å3Block, colorless
Z = 80.20 × 0.10 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
6391 independent reflections
Radiation source: fine-focus sealed tube3739 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.573, Tmax = 0.735k = 1717
23517 measured reflectionsl = 1922
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0612P)2]
where P = (Fo2 + 2Fc2)/3
6391 reflections(Δ/σ)max = 0.001
435 parametersΔρmax = 0.48 e Å3
18 restraintsΔρmin = 0.26 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.

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) top
xyzUiso*/UeqOcc. (<1)
Br10.52079 (4)0.38284 (3)0.91488 (2)0.08200 (17)
S10.24318 (6)0.38797 (6)0.25467 (4)0.0512 (2)
C10.4966 (3)0.3862 (2)0.80445 (17)0.0508 (8)
C20.5875 (3)0.3749 (2)0.76520 (19)0.0530 (8)
H20.66100.36590.79250.064*
C30.3867 (3)0.3996 (3)0.76561 (18)0.0573 (9)
H30.32610.40680.79300.069*
C40.5680 (2)0.3772 (2)0.68510 (18)0.0486 (8)
H40.62910.37010.65810.058*
C50.3685 (2)0.4021 (2)0.68448 (17)0.0518 (8)
H50.29500.41180.65740.062*
C60.4584 (2)0.3901 (2)0.64382 (16)0.0417 (7)
C70.4467 (2)0.3918 (2)0.55710 (17)0.0413 (7)
C80.3045 (2)0.3940 (2)0.43557 (17)0.0433 (7)
C90.3749 (2)0.3811 (2)0.31337 (17)0.0418 (7)
C100.3181 (2)0.3741 (2)0.17853 (17)0.0467 (7)
C110.2592 (3)0.3727 (3)0.0955 (2)0.0649 (10)
F10.3240 (5)0.3348 (6)0.0502 (3)0.127 (5)0.647 (14)
F20.1636 (5)0.3260 (4)0.0875 (2)0.115 (4)0.647 (14)
F30.2342 (4)0.4579 (3)0.07029 (18)0.102 (3)0.647 (14)
F1'0.3272 (4)0.3938 (3)0.04639 (18)0.131 (10)0.353 (14)
F2'0.2233 (4)0.2828 (3)0.07632 (18)0.111 (7)0.353 (14)
F3'0.1710 (4)0.4272 (3)0.08213 (18)0.139 (10)0.353 (14)
N10.4276 (2)0.36517 (19)0.19781 (15)0.0544 (7)
N20.4611 (2)0.36946 (19)0.27711 (15)0.0523 (7)
N30.39017 (19)0.38751 (17)0.39329 (13)0.0441 (6)
H3A0.45910.38740.41810.053*
N40.33647 (18)0.39642 (18)0.51566 (12)0.0444 (6)
H4A0.28210.40120.54270.053*
O10.20389 (16)0.39720 (19)0.40587 (12)0.0603 (6)
O20.52977 (16)0.38943 (17)0.52432 (12)0.0573 (6)
Br20.78867 (3)0.35054 (3)0.06584 (2)0.07307 (16)
S21.07298 (6)0.37309 (6)0.72621 (5)0.0517 (2)
C120.8182 (3)0.3580 (2)0.17553 (18)0.0480 (8)
C130.7282 (3)0.3619 (2)0.2160 (2)0.0580 (9)
H130.65350.36030.18950.070*
C140.9298 (3)0.3587 (2)0.21458 (18)0.0548 (8)
H140.99060.35520.18700.066*
C150.7490 (2)0.3683 (2)0.29619 (19)0.0549 (9)
H150.68790.37170.32350.066*
C160.9497 (2)0.3645 (2)0.29466 (18)0.0514 (8)
H161.02460.36490.32100.062*
C170.8603 (2)0.3697 (2)0.33681 (17)0.0415 (7)
C180.8728 (2)0.3777 (2)0.42240 (18)0.0447 (7)
C191.0133 (2)0.3809 (2)0.54479 (17)0.0420 (7)
C200.9418 (2)0.3769 (2)0.66670 (17)0.0441 (7)
C210.9967 (3)0.3711 (2)0.80164 (18)0.0511 (8)
C221.0521 (4)0.3684 (3)0.8853 (2)0.0705 (11)
F41.1628 (4)0.3696 (4)0.8914 (2)0.128 (3)0.740 (10)
F51.0182 (5)0.2993 (3)0.9232 (2)0.146 (3)0.740 (10)
F61.0291 (3)0.4471 (3)0.92201 (16)0.1034 (19)0.740 (10)
F4'1.1000 (3)0.2796 (3)0.90126 (16)0.084 (5)0.260 (10)
F5'0.9817 (3)0.3756 (3)0.93477 (16)0.140 (7)0.260 (10)
F6'1.1343 (3)0.4257 (3)0.90097 (16)0.119 (8)0.260 (10)
N50.8867 (2)0.3730 (2)0.78220 (16)0.0616 (8)
N60.8536 (2)0.3763 (2)0.70278 (16)0.0615 (8)
N70.92768 (19)0.38024 (18)0.58706 (14)0.0483 (6)
H70.85880.38190.56210.058*
N80.98284 (19)0.37966 (17)0.46500 (13)0.0450 (6)
H81.03800.38020.43840.054*
O31.11400 (16)0.38297 (17)0.57549 (12)0.0562 (6)
O40.78945 (17)0.38369 (18)0.45521 (13)0.0672 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0825 (3)0.1187 (4)0.0399 (2)0.0191 (2)0.00480 (18)0.00366 (19)
S10.0315 (4)0.0801 (6)0.0414 (4)0.0030 (4)0.0037 (3)0.0006 (4)
C10.0517 (19)0.065 (2)0.0334 (16)0.0113 (15)0.0002 (14)0.0026 (14)
C20.0389 (16)0.067 (2)0.0494 (19)0.0024 (15)0.0043 (15)0.0047 (15)
C30.0419 (17)0.091 (3)0.0394 (18)0.0034 (16)0.0076 (14)0.0077 (16)
C40.0299 (15)0.066 (2)0.0482 (19)0.0023 (13)0.0018 (13)0.0001 (14)
C50.0311 (15)0.081 (2)0.0418 (17)0.0014 (15)0.0006 (13)0.0030 (15)
C60.0360 (15)0.0501 (17)0.0385 (16)0.0020 (13)0.0045 (12)0.0011 (13)
C70.0271 (14)0.0534 (18)0.0429 (17)0.0015 (12)0.0037 (12)0.0009 (13)
C80.0314 (15)0.0594 (19)0.0395 (17)0.0014 (13)0.0067 (13)0.0032 (13)
C90.0314 (14)0.0494 (17)0.0455 (18)0.0031 (13)0.0096 (13)0.0010 (13)
C100.0398 (16)0.0598 (19)0.0407 (17)0.0027 (14)0.0077 (13)0.0001 (14)
C110.064 (2)0.089 (3)0.041 (2)0.002 (2)0.0053 (18)0.002 (2)
F10.127 (7)0.202 (10)0.048 (3)0.057 (6)0.005 (3)0.029 (3)
F20.104 (5)0.171 (9)0.059 (2)0.072 (5)0.025 (2)0.021 (3)
F30.127 (6)0.102 (4)0.065 (3)0.007 (4)0.019 (3)0.028 (2)
F1'0.109 (12)0.24 (2)0.044 (5)0.071 (13)0.023 (5)0.012 (7)
F2'0.139 (13)0.090 (6)0.082 (7)0.006 (6)0.053 (8)0.020 (4)
F3'0.117 (10)0.22 (2)0.062 (5)0.105 (13)0.028 (5)0.017 (8)
N10.0416 (14)0.079 (2)0.0440 (16)0.0038 (13)0.0115 (12)0.0002 (13)
N20.0337 (13)0.0786 (19)0.0450 (16)0.0041 (12)0.0081 (12)0.0024 (13)
N30.0289 (12)0.0697 (17)0.0335 (13)0.0010 (11)0.0044 (10)0.0010 (11)
N40.0281 (12)0.0721 (17)0.0334 (13)0.0012 (11)0.0064 (10)0.0028 (11)
O10.0281 (10)0.1135 (19)0.0385 (12)0.0048 (11)0.0033 (9)0.0046 (12)
O20.0292 (11)0.0953 (17)0.0476 (13)0.0019 (11)0.0067 (10)0.0011 (11)
Br20.0844 (3)0.0828 (3)0.0452 (2)0.0046 (2)0.00983 (18)0.00186 (17)
S20.0361 (4)0.0742 (6)0.0440 (5)0.0043 (4)0.0043 (3)0.0031 (4)
C120.0489 (18)0.0494 (18)0.0422 (17)0.0024 (14)0.0029 (14)0.0003 (13)
C130.0390 (17)0.075 (2)0.055 (2)0.0019 (15)0.0074 (16)0.0002 (17)
C140.0424 (17)0.077 (2)0.0451 (19)0.0013 (15)0.0069 (14)0.0032 (16)
C150.0301 (15)0.078 (2)0.055 (2)0.0028 (15)0.0035 (14)0.0014 (17)
C160.0315 (15)0.077 (2)0.0445 (18)0.0018 (14)0.0009 (14)0.0047 (15)
C170.0306 (14)0.0496 (18)0.0417 (17)0.0009 (12)0.0020 (12)0.0007 (13)
C180.0302 (15)0.0566 (19)0.0469 (18)0.0004 (13)0.0045 (13)0.0001 (14)
C190.0311 (14)0.0522 (18)0.0433 (17)0.0008 (13)0.0074 (13)0.0008 (13)
C200.0343 (15)0.0605 (19)0.0381 (17)0.0004 (13)0.0074 (13)0.0011 (13)
C210.0482 (19)0.058 (2)0.0469 (19)0.0030 (14)0.0073 (15)0.0038 (14)
C220.076 (3)0.088 (3)0.048 (2)0.010 (2)0.011 (2)0.005 (2)
F40.074 (3)0.246 (9)0.058 (2)0.030 (4)0.0039 (19)0.001 (3)
F50.252 (8)0.126 (5)0.048 (2)0.093 (5)0.010 (4)0.021 (3)
F60.130 (4)0.116 (3)0.059 (2)0.009 (3)0.001 (2)0.027 (2)
F4'0.116 (10)0.072 (7)0.049 (6)0.024 (6)0.028 (5)0.004 (5)
F5'0.123 (9)0.231 (18)0.087 (8)0.037 (11)0.077 (7)0.015 (10)
F6'0.147 (15)0.113 (10)0.077 (8)0.096 (10)0.039 (9)0.008 (7)
N50.0510 (17)0.091 (2)0.0449 (17)0.0026 (14)0.0153 (13)0.0050 (14)
N60.0362 (14)0.098 (2)0.0522 (18)0.0055 (14)0.0125 (13)0.0012 (15)
N70.0282 (12)0.0754 (18)0.0413 (15)0.0014 (12)0.0060 (11)0.0004 (12)
N80.0303 (12)0.0657 (16)0.0391 (14)0.0009 (11)0.0056 (10)0.0040 (11)
O30.0314 (11)0.0945 (18)0.0429 (12)0.0017 (10)0.0065 (9)0.0037 (11)
O40.0321 (11)0.118 (2)0.0520 (14)0.0037 (12)0.0074 (10)0.0015 (13)
Geometric parameters (Å, º) top
Br1—C11.894 (3)Br2—C121.884 (3)
S1—C101.721 (3)S2—C211.711 (3)
S1—C91.723 (3)S2—C201.722 (3)
C1—C21.375 (4)C12—C131.372 (4)
C1—C31.379 (4)C12—C141.385 (4)
C2—C41.374 (4)C13—C151.377 (5)
C2—H20.9300C13—H130.9300
C3—C51.392 (4)C14—C161.375 (4)
C3—H30.9300C14—H140.9300
C4—C61.390 (4)C15—C171.392 (4)
C4—H40.9300C15—H150.9300
C5—C61.382 (4)C16—C171.385 (4)
C5—H50.9300C16—H160.9300
C6—C71.491 (4)C17—C181.475 (4)
C7—O21.217 (3)C18—O41.222 (3)
C7—N41.387 (3)C18—N81.391 (3)
C8—O11.221 (3)C19—O31.226 (3)
C8—N31.350 (4)C19—N71.347 (4)
C8—N41.382 (3)C19—N81.375 (3)
C9—N21.295 (4)C20—N61.304 (4)
C9—N31.374 (3)C20—N71.368 (4)
C10—N11.293 (4)C21—N51.292 (4)
C10—C111.497 (4)C21—C221.496 (5)
C11—F31.271 (5)C22—F6'1.250 (6)
C11—F3'1.278 (6)C22—F51.261 (5)
C11—F21.290 (6)C22—F5'1.296 (6)
C11—F11.296 (7)C22—F41.300 (6)
C11—F1'1.299 (7)C22—F61.310 (5)
C11—F2'1.334 (6)C22—F4'1.358 (6)
N1—N21.372 (3)N5—N61.373 (4)
N3—H3A0.8600N7—H70.8600
N4—H4A0.8600N8—H80.8600
C10—S1—C985.26 (14)C21—S2—C2085.52 (15)
C2—C1—C3121.8 (3)C13—C12—C14120.6 (3)
C2—C1—Br1119.9 (2)C13—C12—Br2119.3 (2)
C3—C1—Br1118.3 (3)C14—C12—Br2120.0 (3)
C4—C2—C1119.0 (3)C12—C13—C15119.7 (3)
C4—C2—H2120.5C12—C13—H13120.2
C1—C2—H2120.5C15—C13—H13120.2
C1—C3—C5118.5 (3)C16—C14—C12119.3 (3)
C1—C3—H3120.7C16—C14—H14120.4
C5—C3—H3120.7C12—C14—H14120.4
C2—C4—C6120.9 (3)C13—C15—C17120.8 (3)
C2—C4—H4119.5C13—C15—H15119.6
C6—C4—H4119.5C17—C15—H15119.6
C6—C5—C3120.7 (3)C14—C16—C17121.2 (3)
C6—C5—H5119.7C14—C16—H16119.4
C3—C5—H5119.7C17—C16—H16119.4
C5—C6—C4119.1 (3)C16—C17—C15118.4 (3)
C5—C6—C7124.3 (2)C16—C17—C18125.3 (2)
C4—C6—C7116.6 (3)C15—C17—C18116.3 (3)
O2—C7—N4121.6 (3)O4—C18—N8120.7 (3)
O2—C7—C6121.6 (2)O4—C18—C17121.3 (3)
N4—C7—C6116.7 (2)N8—C18—C17118.0 (3)
O1—C8—N3122.8 (3)O3—C19—N7122.0 (3)
O1—C8—N4120.9 (3)O3—C19—N8121.1 (3)
N3—C8—N4116.3 (2)N7—C19—N8116.9 (2)
N2—C9—N3121.1 (2)N6—C20—N7120.8 (3)
N2—C9—S1115.4 (2)N6—C20—S2115.3 (2)
N3—C9—S1123.5 (2)N7—C20—S2123.9 (2)
N1—C10—C11122.6 (3)N5—C21—C22121.3 (3)
N1—C10—S1115.7 (2)N5—C21—S2115.9 (2)
C11—C10—S1121.6 (2)C22—C21—S2122.8 (3)
F3—C11—F2105.8 (5)F6'—C22—F5132.0 (4)
F3'—C11—F266.1 (4)F6'—C22—F5'111.8 (3)
F3—C11—F1106.9 (5)F5—C22—F4111.8 (5)
F3'—C11—F1132.5 (4)F5'—C22—F4134.1 (4)
F2—C11—F1109.4 (5)F5—C22—F6105.2 (5)
F3'—C11—F1'109.0 (4)F4—C22—F6103.8 (4)
F2—C11—F1'132.0 (4)F6'—C22—F4'103.9 (4)
F3—C11—F2'136.4 (4)F5'—C22—F4'103.1 (4)
F3'—C11—F2'106.4 (4)F6—C22—F4'139.5 (4)
F1'—C11—F2'104.5 (4)F6'—C22—C21113.5 (4)
F3—C11—C10111.5 (3)F5—C22—C21113.5 (4)
F3'—C11—C10114.0 (3)F5'—C22—C21114.5 (4)
F2—C11—C10111.9 (3)F4—C22—C21110.9 (4)
F1—C11—C10111.1 (4)F6—C22—C21111.0 (4)
F1'—C11—C10112.9 (3)F4'—C22—C21108.9 (3)
F2'—C11—C10109.4 (3)C21—N5—N6112.0 (3)
C10—N1—N2111.7 (2)C20—N6—N5111.3 (2)
C9—N2—N1111.8 (2)C19—N7—C20125.0 (2)
C8—N3—C9124.6 (2)C19—N7—H7117.5
C8—N3—H3A117.7C20—N7—H7117.5
C9—N3—H3A117.7C19—N8—C18127.3 (3)
C8—N4—C7127.0 (2)C19—N8—H8116.3
C8—N4—H4A116.5C18—N8—H8116.3
C7—N4—H4A116.5
C3—C1—C2—C40.0 (5)C14—C12—C13—C151.2 (5)
Br1—C1—C2—C4179.8 (2)Br2—C12—C13—C15179.4 (2)
C2—C1—C3—C50.2 (5)C13—C12—C14—C160.8 (5)
Br1—C1—C3—C5180.0 (2)Br2—C12—C14—C16179.8 (2)
C1—C2—C4—C60.4 (5)C12—C13—C15—C170.7 (5)
C1—C3—C5—C60.8 (5)C12—C14—C16—C170.0 (5)
C3—C5—C6—C41.1 (5)C14—C16—C17—C150.4 (5)
C3—C5—C6—C7179.9 (3)C14—C16—C17—C18179.0 (3)
C2—C4—C6—C50.9 (5)C13—C15—C17—C160.1 (5)
C2—C4—C6—C7179.8 (3)C13—C15—C17—C18179.4 (3)
C5—C6—C7—O2173.5 (3)C16—C17—C18—O4178.7 (3)
C4—C6—C7—O25.4 (4)C15—C17—C18—O40.8 (4)
C5—C6—C7—N46.4 (4)C16—C17—C18—N80.3 (4)
C4—C6—C7—N4174.7 (3)C15—C17—C18—N8179.8 (3)
C10—S1—C9—N20.2 (2)C21—S2—C20—N60.2 (3)
C10—S1—C9—N3179.6 (3)C21—S2—C20—N7179.9 (3)
C9—S1—C10—N10.3 (2)C20—S2—C21—N50.1 (3)
C9—S1—C10—C11179.6 (3)C20—S2—C21—C22179.3 (3)
N1—C10—C11—F3100.8 (5)N5—C21—C22—F6'135.0 (4)
S1—C10—C11—F379.1 (5)S2—C21—C22—F6'44.3 (5)
N1—C10—C11—F3'146.4 (4)N5—C21—C22—F554.9 (6)
S1—C10—C11—F3'33.4 (5)S2—C21—C22—F5125.7 (4)
N1—C10—C11—F2140.9 (5)N5—C21—C22—F5'5.0 (5)
S1—C10—C11—F239.2 (6)S2—C21—C22—F5'174.4 (3)
N1—C10—C11—F118.3 (7)N5—C21—C22—F4178.2 (4)
S1—C10—C11—F1161.8 (5)S2—C21—C22—F41.2 (5)
N1—C10—C11—F1'21.4 (5)N5—C21—C22—F663.3 (5)
S1—C10—C11—F1'158.5 (3)S2—C21—C22—F6116.0 (4)
N1—C10—C11—F2'94.6 (5)N5—C21—C22—F4'109.8 (4)
S1—C10—C11—F2'85.6 (4)S2—C21—C22—F4'70.9 (4)
C11—C10—N1—N2179.5 (3)C22—C21—N5—N6179.4 (3)
S1—C10—N1—N20.4 (3)S2—C21—N5—N60.0 (4)
N3—C9—N2—N1179.8 (2)N7—C20—N6—N5179.9 (3)
S1—C9—N2—N10.1 (3)S2—C20—N6—N50.2 (4)
C10—N1—N2—C90.2 (4)C21—N5—N6—C200.2 (4)
O1—C8—N3—C91.9 (5)O3—C19—N7—C203.3 (5)
N4—C8—N3—C9177.8 (3)N8—C19—N7—C20176.9 (3)
N2—C9—N3—C8176.0 (3)N6—C20—N7—C19179.9 (3)
S1—C9—N3—C84.2 (4)S2—C20—N7—C190.0 (4)
O1—C8—N4—C7178.9 (3)O3—C19—N8—C18179.8 (3)
N3—C8—N4—C70.8 (4)N7—C19—N8—C180.1 (4)
O2—C7—N4—C83.5 (5)O4—C18—N8—C195.2 (5)
C6—C7—N4—C8176.6 (3)C17—C18—N8—C19175.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8···O1i0.862.152.977 (3)162
C16—H16···O1i0.932.423.334 (3)167
N7—H7···O40.861.902.591 (3)136
C5—H5···O3ii0.932.413.301 (3)161
N4—H4A···O3ii0.862.182.995 (3)159
N3—H3A···O20.861.902.588 (3)136
N3—H3A···F5iii0.862.662.990 (5)104
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x1/2, y+1/2, z1/2.
 

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