There are two molecules in the asymmetric unit of the title compound, C
11H
6ClF
3N
4O
2S. 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
CCDC reference: 618200
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (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
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
C11H6BrF3N4O2S | F(000) = 1552 |
Mr = 395.17 | Dx = 1.874 Mg m−3 |
Monoclinic, P21/n | Melting point: 511 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 11.8573 (12) Å | Cell parameters from 5341 reflections |
b = 13.7774 (13) Å | θ = 2.3–25.2° |
c = 17.3795 (17) Å | µ = 3.13 mm−1 |
β = 99.396 (2)° | T = 292 K |
V = 2801.1 (5) Å3 | Block, colorless |
Z = 8 | 0.20 × 0.10 × 0.10 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 6391 independent reflections |
Radiation source: fine-focus sealed tube | 3739 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.573, Tmax = 0.735 | k = −17→17 |
23517 measured reflections | l = −19→22 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-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 parameters | Δρmax = 0.48 e Å−3 |
18 restraints | Δρmin = −0.26 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. |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Br1 | 0.52079 (4) | 0.38284 (3) | 0.91488 (2) | 0.08200 (17) | |
S1 | 0.24318 (6) | 0.38797 (6) | 0.25467 (4) | 0.0512 (2) | |
C1 | 0.4966 (3) | 0.3862 (2) | 0.80445 (17) | 0.0508 (8) | |
C2 | 0.5875 (3) | 0.3749 (2) | 0.76520 (19) | 0.0530 (8) | |
H2 | 0.6610 | 0.3659 | 0.7925 | 0.064* | |
C3 | 0.3867 (3) | 0.3996 (3) | 0.76561 (18) | 0.0573 (9) | |
H3 | 0.3261 | 0.4068 | 0.7930 | 0.069* | |
C4 | 0.5680 (2) | 0.3772 (2) | 0.68510 (18) | 0.0486 (8) | |
H4 | 0.6291 | 0.3701 | 0.6581 | 0.058* | |
C5 | 0.3685 (2) | 0.4021 (2) | 0.68448 (17) | 0.0518 (8) | |
H5 | 0.2950 | 0.4118 | 0.6574 | 0.062* | |
C6 | 0.4584 (2) | 0.3901 (2) | 0.64382 (16) | 0.0417 (7) | |
C7 | 0.4467 (2) | 0.3918 (2) | 0.55710 (17) | 0.0413 (7) | |
C8 | 0.3045 (2) | 0.3940 (2) | 0.43557 (17) | 0.0433 (7) | |
C9 | 0.3749 (2) | 0.3811 (2) | 0.31337 (17) | 0.0418 (7) | |
C10 | 0.3181 (2) | 0.3741 (2) | 0.17853 (17) | 0.0467 (7) | |
C11 | 0.2592 (3) | 0.3727 (3) | 0.0955 (2) | 0.0649 (10) | |
F1 | 0.3240 (5) | 0.3348 (6) | 0.0502 (3) | 0.127 (5) | 0.647 (14) |
F2 | 0.1636 (5) | 0.3260 (4) | 0.0875 (2) | 0.115 (4) | 0.647 (14) |
F3 | 0.2342 (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) |
N1 | 0.4276 (2) | 0.36517 (19) | 0.19781 (15) | 0.0544 (7) | |
N2 | 0.4611 (2) | 0.36946 (19) | 0.27711 (15) | 0.0523 (7) | |
N3 | 0.39017 (19) | 0.38751 (17) | 0.39329 (13) | 0.0441 (6) | |
H3A | 0.4591 | 0.3874 | 0.4181 | 0.053* | |
N4 | 0.33647 (18) | 0.39642 (18) | 0.51566 (12) | 0.0444 (6) | |
H4A | 0.2821 | 0.4012 | 0.5427 | 0.053* | |
O1 | 0.20389 (16) | 0.39720 (19) | 0.40587 (12) | 0.0603 (6) | |
O2 | 0.52977 (16) | 0.38943 (17) | 0.52432 (12) | 0.0573 (6) | |
Br2 | 0.78867 (3) | 0.35054 (3) | 0.06584 (2) | 0.07307 (16) | |
S2 | 1.07298 (6) | 0.37309 (6) | 0.72621 (5) | 0.0517 (2) | |
C12 | 0.8182 (3) | 0.3580 (2) | 0.17553 (18) | 0.0480 (8) | |
C13 | 0.7282 (3) | 0.3619 (2) | 0.2160 (2) | 0.0580 (9) | |
H13 | 0.6535 | 0.3603 | 0.1895 | 0.070* | |
C14 | 0.9298 (3) | 0.3587 (2) | 0.21458 (18) | 0.0548 (8) | |
H14 | 0.9906 | 0.3552 | 0.1870 | 0.066* | |
C15 | 0.7490 (2) | 0.3683 (2) | 0.29619 (19) | 0.0549 (9) | |
H15 | 0.6879 | 0.3717 | 0.3235 | 0.066* | |
C16 | 0.9497 (2) | 0.3645 (2) | 0.29466 (18) | 0.0514 (8) | |
H16 | 1.0246 | 0.3649 | 0.3210 | 0.062* | |
C17 | 0.8603 (2) | 0.3697 (2) | 0.33681 (17) | 0.0415 (7) | |
C18 | 0.8728 (2) | 0.3777 (2) | 0.42240 (18) | 0.0447 (7) | |
C19 | 1.0133 (2) | 0.3809 (2) | 0.54479 (17) | 0.0420 (7) | |
C20 | 0.9418 (2) | 0.3769 (2) | 0.66670 (17) | 0.0441 (7) | |
C21 | 0.9967 (3) | 0.3711 (2) | 0.80164 (18) | 0.0511 (8) | |
C22 | 1.0521 (4) | 0.3684 (3) | 0.8853 (2) | 0.0705 (11) | |
F4 | 1.1628 (4) | 0.3696 (4) | 0.8914 (2) | 0.128 (3) | 0.740 (10) |
F5 | 1.0182 (5) | 0.2993 (3) | 0.9232 (2) | 0.146 (3) | 0.740 (10) |
F6 | 1.0291 (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) |
N5 | 0.8867 (2) | 0.3730 (2) | 0.78220 (16) | 0.0616 (8) | |
N6 | 0.8536 (2) | 0.3763 (2) | 0.70278 (16) | 0.0615 (8) | |
N7 | 0.92768 (19) | 0.38024 (18) | 0.58706 (14) | 0.0483 (6) | |
H7 | 0.8588 | 0.3819 | 0.5621 | 0.058* | |
N8 | 0.98284 (19) | 0.37966 (17) | 0.46500 (13) | 0.0450 (6) | |
H8 | 1.0380 | 0.3802 | 0.4384 | 0.054* | |
O3 | 1.11400 (16) | 0.38297 (17) | 0.57549 (12) | 0.0562 (6) | |
O4 | 0.78945 (17) | 0.38369 (18) | 0.45521 (13) | 0.0672 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0825 (3) | 0.1187 (4) | 0.0399 (2) | −0.0191 (2) | −0.00480 (18) | 0.00366 (19) |
S1 | 0.0315 (4) | 0.0801 (6) | 0.0414 (4) | 0.0030 (4) | 0.0037 (3) | −0.0006 (4) |
C1 | 0.0517 (19) | 0.065 (2) | 0.0334 (16) | −0.0113 (15) | −0.0002 (14) | 0.0026 (14) |
C2 | 0.0389 (16) | 0.067 (2) | 0.0494 (19) | −0.0024 (15) | −0.0043 (15) | 0.0047 (15) |
C3 | 0.0419 (17) | 0.091 (3) | 0.0394 (18) | −0.0034 (16) | 0.0076 (14) | −0.0077 (16) |
C4 | 0.0299 (15) | 0.066 (2) | 0.0482 (19) | −0.0023 (13) | 0.0018 (13) | −0.0001 (14) |
C5 | 0.0311 (15) | 0.081 (2) | 0.0418 (17) | 0.0014 (15) | 0.0006 (13) | −0.0030 (15) |
C6 | 0.0360 (15) | 0.0501 (17) | 0.0385 (16) | −0.0020 (13) | 0.0045 (12) | 0.0011 (13) |
C7 | 0.0271 (14) | 0.0534 (18) | 0.0429 (17) | 0.0015 (12) | 0.0037 (12) | −0.0009 (13) |
C8 | 0.0314 (15) | 0.0594 (19) | 0.0395 (17) | 0.0014 (13) | 0.0067 (13) | 0.0032 (13) |
C9 | 0.0314 (14) | 0.0494 (17) | 0.0455 (18) | −0.0031 (13) | 0.0096 (13) | 0.0010 (13) |
C10 | 0.0398 (16) | 0.0598 (19) | 0.0407 (17) | −0.0027 (14) | 0.0077 (13) | −0.0001 (14) |
C11 | 0.064 (2) | 0.089 (3) | 0.041 (2) | −0.002 (2) | 0.0053 (18) | 0.002 (2) |
F1 | 0.127 (7) | 0.202 (10) | 0.048 (3) | 0.057 (6) | 0.005 (3) | −0.029 (3) |
F2 | 0.104 (5) | 0.171 (9) | 0.059 (2) | −0.072 (5) | −0.025 (2) | 0.021 (3) |
F3 | 0.127 (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) |
N1 | 0.0416 (14) | 0.079 (2) | 0.0440 (16) | 0.0038 (13) | 0.0115 (12) | −0.0002 (13) |
N2 | 0.0337 (13) | 0.0786 (19) | 0.0450 (16) | 0.0041 (12) | 0.0081 (12) | 0.0024 (13) |
N3 | 0.0289 (12) | 0.0697 (17) | 0.0335 (13) | −0.0010 (11) | 0.0044 (10) | 0.0010 (11) |
N4 | 0.0281 (12) | 0.0721 (17) | 0.0334 (13) | 0.0012 (11) | 0.0064 (10) | 0.0028 (11) |
O1 | 0.0281 (10) | 0.1135 (19) | 0.0385 (12) | 0.0048 (11) | 0.0033 (9) | 0.0046 (12) |
O2 | 0.0292 (11) | 0.0953 (17) | 0.0476 (13) | 0.0019 (11) | 0.0067 (10) | −0.0011 (11) |
Br2 | 0.0844 (3) | 0.0828 (3) | 0.0452 (2) | −0.0046 (2) | −0.00983 (18) | −0.00186 (17) |
S2 | 0.0361 (4) | 0.0742 (6) | 0.0440 (5) | −0.0043 (4) | 0.0043 (3) | 0.0031 (4) |
C12 | 0.0489 (18) | 0.0494 (18) | 0.0422 (17) | −0.0024 (14) | −0.0029 (14) | −0.0003 (13) |
C13 | 0.0390 (17) | 0.075 (2) | 0.055 (2) | −0.0019 (15) | −0.0074 (16) | −0.0002 (17) |
C14 | 0.0424 (17) | 0.077 (2) | 0.0451 (19) | 0.0013 (15) | 0.0069 (14) | −0.0032 (16) |
C15 | 0.0301 (15) | 0.078 (2) | 0.055 (2) | 0.0028 (15) | 0.0035 (14) | −0.0014 (17) |
C16 | 0.0315 (15) | 0.077 (2) | 0.0445 (18) | 0.0018 (14) | 0.0009 (14) | −0.0047 (15) |
C17 | 0.0306 (14) | 0.0496 (18) | 0.0417 (17) | −0.0009 (12) | −0.0020 (12) | 0.0007 (13) |
C18 | 0.0302 (15) | 0.0566 (19) | 0.0469 (18) | 0.0004 (13) | 0.0045 (13) | −0.0001 (14) |
C19 | 0.0311 (14) | 0.0522 (18) | 0.0433 (17) | −0.0008 (13) | 0.0074 (13) | 0.0008 (13) |
C20 | 0.0343 (15) | 0.0605 (19) | 0.0381 (17) | 0.0004 (13) | 0.0074 (13) | −0.0011 (13) |
C21 | 0.0482 (19) | 0.058 (2) | 0.0469 (19) | −0.0030 (14) | 0.0073 (15) | 0.0038 (14) |
C22 | 0.076 (3) | 0.088 (3) | 0.048 (2) | −0.010 (2) | 0.011 (2) | −0.005 (2) |
F4 | 0.074 (3) | 0.246 (9) | 0.058 (2) | 0.030 (4) | −0.0039 (19) | −0.001 (3) |
F5 | 0.252 (8) | 0.126 (5) | 0.048 (2) | −0.093 (5) | −0.010 (4) | 0.021 (3) |
F6 | 0.130 (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) |
N5 | 0.0510 (17) | 0.091 (2) | 0.0449 (17) | 0.0026 (14) | 0.0153 (13) | 0.0050 (14) |
N6 | 0.0362 (14) | 0.098 (2) | 0.0522 (18) | 0.0055 (14) | 0.0125 (13) | 0.0012 (15) |
N7 | 0.0282 (12) | 0.0754 (18) | 0.0413 (15) | 0.0014 (12) | 0.0060 (11) | 0.0004 (12) |
N8 | 0.0303 (12) | 0.0657 (16) | 0.0391 (14) | 0.0009 (11) | 0.0056 (10) | −0.0040 (11) |
O3 | 0.0314 (11) | 0.0945 (18) | 0.0429 (12) | −0.0017 (10) | 0.0065 (9) | −0.0037 (11) |
O4 | 0.0321 (11) | 0.118 (2) | 0.0520 (14) | 0.0037 (12) | 0.0074 (10) | −0.0015 (13) |
Geometric parameters (Å, º) top
Br1—C1 | 1.894 (3) | Br2—C12 | 1.884 (3) |
S1—C10 | 1.721 (3) | S2—C21 | 1.711 (3) |
S1—C9 | 1.723 (3) | S2—C20 | 1.722 (3) |
C1—C2 | 1.375 (4) | C12—C13 | 1.372 (4) |
C1—C3 | 1.379 (4) | C12—C14 | 1.385 (4) |
C2—C4 | 1.374 (4) | C13—C15 | 1.377 (5) |
C2—H2 | 0.9300 | C13—H13 | 0.9300 |
C3—C5 | 1.392 (4) | C14—C16 | 1.375 (4) |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C4—C6 | 1.390 (4) | C15—C17 | 1.392 (4) |
C4—H4 | 0.9300 | C15—H15 | 0.9300 |
C5—C6 | 1.382 (4) | C16—C17 | 1.385 (4) |
C5—H5 | 0.9300 | C16—H16 | 0.9300 |
C6—C7 | 1.491 (4) | C17—C18 | 1.475 (4) |
C7—O2 | 1.217 (3) | C18—O4 | 1.222 (3) |
C7—N4 | 1.387 (3) | C18—N8 | 1.391 (3) |
C8—O1 | 1.221 (3) | C19—O3 | 1.226 (3) |
C8—N3 | 1.350 (4) | C19—N7 | 1.347 (4) |
C8—N4 | 1.382 (3) | C19—N8 | 1.375 (3) |
C9—N2 | 1.295 (4) | C20—N6 | 1.304 (4) |
C9—N3 | 1.374 (3) | C20—N7 | 1.368 (4) |
C10—N1 | 1.293 (4) | C21—N5 | 1.292 (4) |
C10—C11 | 1.497 (4) | C21—C22 | 1.496 (5) |
C11—F3 | 1.271 (5) | C22—F6' | 1.250 (6) |
C11—F3' | 1.278 (6) | C22—F5 | 1.261 (5) |
C11—F2 | 1.290 (6) | C22—F5' | 1.296 (6) |
C11—F1 | 1.296 (7) | C22—F4 | 1.300 (6) |
C11—F1' | 1.299 (7) | C22—F6 | 1.310 (5) |
C11—F2' | 1.334 (6) | C22—F4' | 1.358 (6) |
N1—N2 | 1.372 (3) | N5—N6 | 1.373 (4) |
N3—H3A | 0.8600 | N7—H7 | 0.8600 |
N4—H4A | 0.8600 | N8—H8 | 0.8600 |
| | | |
C10—S1—C9 | 85.26 (14) | C21—S2—C20 | 85.52 (15) |
C2—C1—C3 | 121.8 (3) | C13—C12—C14 | 120.6 (3) |
C2—C1—Br1 | 119.9 (2) | C13—C12—Br2 | 119.3 (2) |
C3—C1—Br1 | 118.3 (3) | C14—C12—Br2 | 120.0 (3) |
C4—C2—C1 | 119.0 (3) | C12—C13—C15 | 119.7 (3) |
C4—C2—H2 | 120.5 | C12—C13—H13 | 120.2 |
C1—C2—H2 | 120.5 | C15—C13—H13 | 120.2 |
C1—C3—C5 | 118.5 (3) | C16—C14—C12 | 119.3 (3) |
C1—C3—H3 | 120.7 | C16—C14—H14 | 120.4 |
C5—C3—H3 | 120.7 | C12—C14—H14 | 120.4 |
C2—C4—C6 | 120.9 (3) | C13—C15—C17 | 120.8 (3) |
C2—C4—H4 | 119.5 | C13—C15—H15 | 119.6 |
C6—C4—H4 | 119.5 | C17—C15—H15 | 119.6 |
C6—C5—C3 | 120.7 (3) | C14—C16—C17 | 121.2 (3) |
C6—C5—H5 | 119.7 | C14—C16—H16 | 119.4 |
C3—C5—H5 | 119.7 | C17—C16—H16 | 119.4 |
C5—C6—C4 | 119.1 (3) | C16—C17—C15 | 118.4 (3) |
C5—C6—C7 | 124.3 (2) | C16—C17—C18 | 125.3 (2) |
C4—C6—C7 | 116.6 (3) | C15—C17—C18 | 116.3 (3) |
O2—C7—N4 | 121.6 (3) | O4—C18—N8 | 120.7 (3) |
O2—C7—C6 | 121.6 (2) | O4—C18—C17 | 121.3 (3) |
N4—C7—C6 | 116.7 (2) | N8—C18—C17 | 118.0 (3) |
O1—C8—N3 | 122.8 (3) | O3—C19—N7 | 122.0 (3) |
O1—C8—N4 | 120.9 (3) | O3—C19—N8 | 121.1 (3) |
N3—C8—N4 | 116.3 (2) | N7—C19—N8 | 116.9 (2) |
N2—C9—N3 | 121.1 (2) | N6—C20—N7 | 120.8 (3) |
N2—C9—S1 | 115.4 (2) | N6—C20—S2 | 115.3 (2) |
N3—C9—S1 | 123.5 (2) | N7—C20—S2 | 123.9 (2) |
N1—C10—C11 | 122.6 (3) | N5—C21—C22 | 121.3 (3) |
N1—C10—S1 | 115.7 (2) | N5—C21—S2 | 115.9 (2) |
C11—C10—S1 | 121.6 (2) | C22—C21—S2 | 122.8 (3) |
F3—C11—F2 | 105.8 (5) | F6'—C22—F5 | 132.0 (4) |
F3'—C11—F2 | 66.1 (4) | F6'—C22—F5' | 111.8 (3) |
F3—C11—F1 | 106.9 (5) | F5—C22—F4 | 111.8 (5) |
F3'—C11—F1 | 132.5 (4) | F5'—C22—F4 | 134.1 (4) |
F2—C11—F1 | 109.4 (5) | F5—C22—F6 | 105.2 (5) |
F3'—C11—F1' | 109.0 (4) | F4—C22—F6 | 103.8 (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—C21 | 113.5 (4) |
F3—C11—C10 | 111.5 (3) | F5—C22—C21 | 113.5 (4) |
F3'—C11—C10 | 114.0 (3) | F5'—C22—C21 | 114.5 (4) |
F2—C11—C10 | 111.9 (3) | F4—C22—C21 | 110.9 (4) |
F1—C11—C10 | 111.1 (4) | F6—C22—C21 | 111.0 (4) |
F1'—C11—C10 | 112.9 (3) | F4'—C22—C21 | 108.9 (3) |
F2'—C11—C10 | 109.4 (3) | C21—N5—N6 | 112.0 (3) |
C10—N1—N2 | 111.7 (2) | C20—N6—N5 | 111.3 (2) |
C9—N2—N1 | 111.8 (2) | C19—N7—C20 | 125.0 (2) |
C8—N3—C9 | 124.6 (2) | C19—N7—H7 | 117.5 |
C8—N3—H3A | 117.7 | C20—N7—H7 | 117.5 |
C9—N3—H3A | 117.7 | C19—N8—C18 | 127.3 (3) |
C8—N4—C7 | 127.0 (2) | C19—N8—H8 | 116.3 |
C8—N4—H4A | 116.5 | C18—N8—H8 | 116.3 |
C7—N4—H4A | 116.5 | | |
| | | |
C3—C1—C2—C4 | 0.0 (5) | C14—C12—C13—C15 | 1.2 (5) |
Br1—C1—C2—C4 | 179.8 (2) | Br2—C12—C13—C15 | −179.4 (2) |
C2—C1—C3—C5 | −0.2 (5) | C13—C12—C14—C16 | −0.8 (5) |
Br1—C1—C3—C5 | −180.0 (2) | Br2—C12—C14—C16 | 179.8 (2) |
C1—C2—C4—C6 | −0.4 (5) | C12—C13—C15—C17 | −0.7 (5) |
C1—C3—C5—C6 | 0.8 (5) | C12—C14—C16—C17 | 0.0 (5) |
C3—C5—C6—C4 | −1.1 (5) | C14—C16—C17—C15 | 0.4 (5) |
C3—C5—C6—C7 | −179.9 (3) | C14—C16—C17—C18 | −179.0 (3) |
C2—C4—C6—C5 | 0.9 (5) | C13—C15—C17—C16 | −0.1 (5) |
C2—C4—C6—C7 | 179.8 (3) | C13—C15—C17—C18 | 179.4 (3) |
C5—C6—C7—O2 | 173.5 (3) | C16—C17—C18—O4 | 178.7 (3) |
C4—C6—C7—O2 | −5.4 (4) | C15—C17—C18—O4 | −0.8 (4) |
C5—C6—C7—N4 | −6.4 (4) | C16—C17—C18—N8 | −0.3 (4) |
C4—C6—C7—N4 | 174.7 (3) | C15—C17—C18—N8 | −179.8 (3) |
C10—S1—C9—N2 | −0.2 (2) | C21—S2—C20—N6 | −0.2 (3) |
C10—S1—C9—N3 | 179.6 (3) | C21—S2—C20—N7 | 179.9 (3) |
C9—S1—C10—N1 | 0.3 (2) | C20—S2—C21—N5 | 0.1 (3) |
C9—S1—C10—C11 | −179.6 (3) | C20—S2—C21—C22 | −179.3 (3) |
N1—C10—C11—F3 | −100.8 (5) | N5—C21—C22—F6' | −135.0 (4) |
S1—C10—C11—F3 | 79.1 (5) | S2—C21—C22—F6' | 44.3 (5) |
N1—C10—C11—F3' | −146.4 (4) | N5—C21—C22—F5 | 54.9 (6) |
S1—C10—C11—F3' | 33.4 (5) | S2—C21—C22—F5 | −125.7 (4) |
N1—C10—C11—F2 | 140.9 (5) | N5—C21—C22—F5' | −5.0 (5) |
S1—C10—C11—F2 | −39.2 (6) | S2—C21—C22—F5' | 174.4 (3) |
N1—C10—C11—F1 | 18.3 (7) | N5—C21—C22—F4 | −178.2 (4) |
S1—C10—C11—F1 | −161.8 (5) | S2—C21—C22—F4 | 1.2 (5) |
N1—C10—C11—F1' | −21.4 (5) | N5—C21—C22—F6 | −63.3 (5) |
S1—C10—C11—F1' | 158.5 (3) | S2—C21—C22—F6 | 116.0 (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—N2 | 179.5 (3) | C22—C21—N5—N6 | 179.4 (3) |
S1—C10—N1—N2 | −0.4 (3) | S2—C21—N5—N6 | 0.0 (4) |
N3—C9—N2—N1 | −179.8 (2) | N7—C20—N6—N5 | −179.9 (3) |
S1—C9—N2—N1 | 0.1 (3) | S2—C20—N6—N5 | 0.2 (4) |
C10—N1—N2—C9 | 0.2 (4) | C21—N5—N6—C20 | −0.2 (4) |
O1—C8—N3—C9 | −1.9 (5) | O3—C19—N7—C20 | −3.3 (5) |
N4—C8—N3—C9 | 177.8 (3) | N8—C19—N7—C20 | 176.9 (3) |
N2—C9—N3—C8 | −176.0 (3) | N6—C20—N7—C19 | −179.9 (3) |
S1—C9—N3—C8 | 4.2 (4) | S2—C20—N7—C19 | 0.0 (4) |
O1—C8—N4—C7 | 178.9 (3) | O3—C19—N8—C18 | −179.8 (3) |
N3—C8—N4—C7 | −0.8 (4) | N7—C19—N8—C18 | −0.1 (4) |
O2—C7—N4—C8 | 3.5 (5) | O4—C18—N8—C19 | 5.2 (5) |
C6—C7—N4—C8 | −176.6 (3) | C17—C18—N8—C19 | −175.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N8—H8···O1i | 0.86 | 2.15 | 2.977 (3) | 162 |
C16—H16···O1i | 0.93 | 2.42 | 3.334 (3) | 167 |
N7—H7···O4 | 0.86 | 1.90 | 2.591 (3) | 136 |
C5—H5···O3ii | 0.93 | 2.41 | 3.301 (3) | 161 |
N4—H4A···O3ii | 0.86 | 2.18 | 2.995 (3) | 159 |
N3—H3A···O2 | 0.86 | 1.90 | 2.588 (3) | 136 |
N3—H3A···F5iii | 0.86 | 2.66 | 2.990 (5) | 104 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x−1/2, −y+1/2, z−1/2. |