In the title compound, C10H6F2N4O2S, the urea group is essentially coplanar with the thiadiazole ring and nearly perpendicular to the benzene ring. The face-to-face distance of 3.2225 (15) Å and the centroid separation of 3.5862 (17) Å between parallel thiadiazole rings indicate the existence of π–π stacking between neighbouring molecules. There are two molecules in the asymmetric unit.
Supporting information
CCDC reference: 282704
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.049
- wR factor = 0.144
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 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-(2,6-Difluorobenzoyl)-3-(5–1,3,4-thiadiazol-2-yl)urea
top
Crystal data top
C10H6F2N4O2S | F(000) = 1152 |
Mr = 284.26 | Dx = 1.588 Mg m−3 |
Monoclinic, P21/c | Melting point: 472 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 20.674 (2) Å | Cell parameters from 3500 reflections |
b = 8.2442 (9) Å | θ = 2.7–24.1° |
c = 14.9541 (16) Å | µ = 0.30 mm−1 |
β = 111.106 (2)° | T = 292 K |
V = 2377.8 (4) Å3 | Block, colourless |
Z = 8 | 0.40 × 0.20 × 0.10 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4661 independent reflections |
Radiation source: fine-focus sealed tube | 3583 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 26.0°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −25→18 |
Tmin = 0.889, Tmax = 0.970 | k = −9→10 |
12506 measured reflections | l = −18→18 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0741P)2 + 0.3849P] where P = (Fo2 + 2Fc2)/3 |
4661 reflections | (Δ/σ)max < 0.001 |
343 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.25 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 | |
C1 | 0.83188 (14) | −0.2225 (3) | 0.03202 (17) | 0.0466 (6) | |
C2 | 0.88114 (15) | −0.3240 (3) | 0.02044 (18) | 0.0514 (7) | |
C3 | 0.86597 (17) | −0.4497 (4) | −0.0435 (2) | 0.0612 (8) | |
H3 | 0.9008 | −0.5166 | −0.0482 | 0.073* | |
C4 | 0.79829 (19) | −0.4742 (4) | −0.1002 (2) | 0.0686 (9) | |
H4 | 0.7869 | −0.5588 | −0.1443 | 0.082* | |
C5 | 0.74658 (18) | −0.3749 (4) | −0.0930 (2) | 0.0696 (9) | |
H5 | 0.7006 | −0.3911 | −0.1322 | 0.084* | |
C6 | 0.76435 (16) | −0.2529 (4) | −0.0273 (2) | 0.0566 (7) | |
C7 | 0.84870 (16) | −0.0937 (3) | 0.10735 (18) | 0.0525 (7) | |
C8 | 0.90268 (13) | 0.1774 (3) | 0.14393 (16) | 0.0413 (6) | |
C9 | 0.90321 (12) | 0.3165 (3) | 0.28583 (16) | 0.0401 (5) | |
C10 | 0.93300 (16) | 0.5591 (4) | 0.36962 (19) | 0.0572 (7) | |
H10 | 0.9479 | 0.6617 | 0.3943 | 0.069* | |
C11 | 0.67940 (14) | 0.2747 (3) | 0.65965 (19) | 0.0511 (7) | |
C12 | 0.67327 (16) | 0.2052 (4) | 0.7399 (2) | 0.0647 (8) | |
C13 | 0.7002 (2) | 0.0549 (5) | 0.7738 (3) | 0.0921 (13) | |
H13 | 0.6937 | 0.0097 | 0.8269 | 0.111* | |
C14 | 0.7370 (2) | −0.0266 (5) | 0.7275 (4) | 0.0998 (15) | |
H14 | 0.7556 | −0.1281 | 0.7496 | 0.120* | |
C15 | 0.74652 (17) | 0.0390 (4) | 0.6501 (3) | 0.0799 (11) | |
H15 | 0.7723 | −0.0152 | 0.6197 | 0.096* | |
C16 | 0.71731 (15) | 0.1871 (4) | 0.6176 (2) | 0.0610 (8) | |
C17 | 0.64716 (14) | 0.4344 (3) | 0.62269 (19) | 0.0518 (6) | |
C18 | 0.57088 (14) | 0.5606 (3) | 0.47037 (19) | 0.0492 (6) | |
C19 | 0.56401 (13) | 0.8514 (3) | 0.46441 (18) | 0.0451 (6) | |
C20 | 0.52640 (17) | 1.0734 (4) | 0.3599 (2) | 0.0634 (8) | |
H20 | 0.5081 | 1.1471 | 0.3101 | 0.076* | |
F1 | 0.71461 (10) | −0.1550 (3) | −0.01836 (14) | 0.0888 (6) | |
F2 | 0.94770 (9) | −0.2961 (2) | 0.07601 (13) | 0.0769 (5) | |
F3 | 0.72665 (11) | 0.2510 (3) | 0.54068 (15) | 0.0903 (6) | |
F4 | 0.63749 (11) | 0.2878 (3) | 0.78515 (14) | 0.0925 (6) | |
N1 | 0.88049 (11) | 0.0393 (2) | 0.08835 (14) | 0.0435 (5) | |
H1 | 0.8877 | 0.0375 | 0.0352 | 0.052* | |
N2 | 0.88761 (11) | 0.1838 (2) | 0.22519 (13) | 0.0455 (5) | |
H2 | 0.8675 | 0.1018 | 0.2395 | 0.055* | |
N3 | 0.88834 (12) | 0.3140 (3) | 0.36311 (14) | 0.0486 (5) | |
N4 | 0.90610 (12) | 0.4588 (3) | 0.41170 (15) | 0.0530 (6) | |
N5 | 0.60231 (11) | 0.4300 (2) | 0.52963 (15) | 0.0522 (6) | |
H5A | 0.5922 | 0.3352 | 0.5045 | 0.063* | |
N6 | 0.58189 (12) | 0.7081 (2) | 0.51324 (15) | 0.0511 (6) | |
H6 | 0.6012 | 0.7118 | 0.5746 | 0.061* | |
N7 | 0.58212 (12) | 0.9889 (2) | 0.50843 (16) | 0.0524 (6) | |
N8 | 0.56013 (13) | 1.1175 (3) | 0.44605 (16) | 0.0557 (6) | |
O1 | 0.83356 (15) | −0.1091 (3) | 0.17809 (15) | 0.0884 (8) | |
O2 | 0.93377 (11) | 0.2837 (2) | 0.12068 (13) | 0.0579 (5) | |
O3 | 0.66024 (12) | 0.5562 (2) | 0.67163 (14) | 0.0745 (6) | |
O4 | 0.53709 (11) | 0.5402 (2) | 0.38662 (14) | 0.0700 (6) | |
S1 | 0.93984 (4) | 0.49229 (8) | 0.26512 (5) | 0.0506 (2) | |
S2 | 0.51749 (5) | 0.86678 (9) | 0.34356 (5) | 0.0674 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0715 (18) | 0.0338 (13) | 0.0395 (13) | −0.0082 (12) | 0.0261 (13) | −0.0016 (10) |
C2 | 0.0615 (17) | 0.0467 (16) | 0.0462 (14) | −0.0068 (13) | 0.0194 (13) | −0.0038 (12) |
C3 | 0.082 (2) | 0.0464 (16) | 0.0593 (17) | 0.0029 (15) | 0.0300 (16) | −0.0094 (14) |
C4 | 0.094 (2) | 0.0574 (19) | 0.0504 (16) | −0.0113 (17) | 0.0207 (17) | −0.0188 (14) |
C5 | 0.069 (2) | 0.076 (2) | 0.0538 (17) | −0.0106 (17) | 0.0100 (15) | −0.0123 (16) |
C6 | 0.0684 (19) | 0.0528 (17) | 0.0498 (15) | 0.0040 (14) | 0.0226 (14) | 0.0014 (13) |
C7 | 0.0776 (19) | 0.0429 (15) | 0.0443 (13) | −0.0075 (13) | 0.0308 (13) | −0.0055 (12) |
C8 | 0.0543 (15) | 0.0382 (14) | 0.0357 (12) | 0.0009 (11) | 0.0214 (11) | −0.0011 (10) |
C9 | 0.0487 (14) | 0.0383 (13) | 0.0347 (12) | 0.0025 (11) | 0.0168 (10) | 0.0001 (10) |
C10 | 0.085 (2) | 0.0472 (16) | 0.0470 (15) | −0.0115 (14) | 0.0327 (15) | −0.0121 (12) |
C11 | 0.0509 (15) | 0.0402 (15) | 0.0524 (15) | −0.0062 (12) | 0.0066 (12) | −0.0052 (12) |
C12 | 0.0619 (19) | 0.063 (2) | 0.0619 (18) | −0.0021 (15) | 0.0131 (15) | 0.0046 (15) |
C13 | 0.092 (3) | 0.072 (3) | 0.087 (3) | −0.005 (2) | 0.002 (2) | 0.034 (2) |
C14 | 0.082 (3) | 0.053 (2) | 0.123 (4) | 0.0135 (19) | −0.013 (3) | 0.011 (2) |
C15 | 0.061 (2) | 0.060 (2) | 0.093 (3) | 0.0113 (16) | −0.0033 (18) | −0.021 (2) |
C16 | 0.0573 (17) | 0.0516 (18) | 0.0637 (18) | −0.0014 (14) | 0.0091 (14) | −0.0106 (14) |
C17 | 0.0589 (16) | 0.0399 (15) | 0.0512 (15) | −0.0034 (12) | 0.0132 (13) | −0.0043 (12) |
C18 | 0.0553 (16) | 0.0313 (13) | 0.0533 (15) | −0.0057 (11) | 0.0101 (13) | −0.0066 (11) |
C19 | 0.0489 (14) | 0.0340 (13) | 0.0494 (14) | −0.0043 (11) | 0.0139 (12) | −0.0060 (11) |
C20 | 0.085 (2) | 0.0431 (16) | 0.0557 (17) | −0.0026 (15) | 0.0176 (15) | 0.0034 (13) |
F1 | 0.0775 (12) | 0.0979 (15) | 0.0890 (13) | 0.0221 (11) | 0.0276 (11) | −0.0114 (11) |
F2 | 0.0627 (11) | 0.0802 (13) | 0.0818 (12) | −0.0063 (9) | 0.0188 (9) | −0.0207 (10) |
F3 | 0.0954 (15) | 0.1004 (16) | 0.0842 (13) | 0.0078 (12) | 0.0433 (12) | −0.0087 (12) |
F4 | 0.0998 (15) | 0.1077 (17) | 0.0772 (12) | 0.0059 (12) | 0.0408 (12) | 0.0082 (12) |
N1 | 0.0660 (13) | 0.0364 (11) | 0.0363 (10) | −0.0034 (10) | 0.0285 (10) | −0.0027 (8) |
N2 | 0.0669 (14) | 0.0379 (11) | 0.0401 (11) | −0.0076 (10) | 0.0295 (10) | −0.0038 (9) |
N3 | 0.0721 (15) | 0.0431 (12) | 0.0380 (10) | −0.0022 (10) | 0.0287 (10) | −0.0025 (9) |
N4 | 0.0760 (16) | 0.0491 (13) | 0.0400 (11) | −0.0048 (11) | 0.0284 (11) | −0.0070 (10) |
N5 | 0.0635 (14) | 0.0277 (11) | 0.0540 (13) | −0.0044 (10) | 0.0075 (11) | −0.0066 (9) |
N6 | 0.0658 (14) | 0.0308 (11) | 0.0462 (12) | −0.0006 (10) | 0.0074 (10) | −0.0050 (9) |
N7 | 0.0604 (14) | 0.0325 (12) | 0.0546 (13) | −0.0048 (10) | 0.0090 (11) | −0.0069 (10) |
N8 | 0.0718 (15) | 0.0292 (11) | 0.0608 (14) | −0.0073 (10) | 0.0175 (12) | −0.0013 (10) |
O1 | 0.164 (2) | 0.0638 (14) | 0.0720 (14) | −0.0489 (15) | 0.0839 (16) | −0.0257 (11) |
O2 | 0.0887 (14) | 0.0451 (11) | 0.0541 (11) | −0.0137 (10) | 0.0431 (10) | −0.0056 (9) |
O3 | 0.1020 (17) | 0.0400 (11) | 0.0576 (12) | 0.0021 (11) | −0.0002 (11) | −0.0128 (10) |
O4 | 0.0885 (15) | 0.0389 (11) | 0.0572 (12) | −0.0026 (10) | −0.0045 (11) | −0.0090 (9) |
S1 | 0.0710 (5) | 0.0446 (4) | 0.0449 (4) | −0.0122 (3) | 0.0312 (3) | −0.0055 (3) |
S2 | 0.0955 (6) | 0.0443 (4) | 0.0468 (4) | −0.0042 (4) | 0.0068 (4) | −0.0071 (3) |
Geometric parameters (Å, º) top
C1—C2 | 1.376 (4) | C12—F4 | 1.352 (4) |
C1—C6 | 1.381 (4) | C12—C13 | 1.378 (5) |
C1—C7 | 1.495 (3) | C13—C14 | 1.375 (6) |
C2—F2 | 1.347 (3) | C13—H13 | 0.9300 |
C2—C3 | 1.367 (4) | C14—C15 | 1.355 (6) |
C3—C4 | 1.365 (4) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—C16 | 1.371 (4) |
C4—C5 | 1.381 (5) | C15—H15 | 0.9300 |
C4—H4 | 0.9300 | C16—F3 | 1.340 (4) |
C5—C6 | 1.362 (4) | C17—O3 | 1.214 (3) |
C5—H5 | 0.9300 | C17—N5 | 1.367 (3) |
C6—F1 | 1.351 (3) | C18—O4 | 1.206 (3) |
C7—O1 | 1.213 (3) | C18—N6 | 1.355 (3) |
C7—N1 | 1.360 (3) | C18—N5 | 1.397 (3) |
C8—O2 | 1.209 (3) | C19—N6 | 1.368 (3) |
C8—N2 | 1.360 (3) | C19—N7 | 1.297 (3) |
C8—N1 | 1.387 (3) | C19—S2 | 1.719 (3) |
C9—N2 | 1.383 (3) | C20—N8 | 1.277 (3) |
C9—N3 | 1.298 (3) | C20—S2 | 1.722 (3) |
C9—S1 | 1.714 (2) | C20—H20 | 0.9300 |
C10—N4 | 1.281 (3) | N1—H1 | 0.8600 |
C10—S1 | 1.710 (3) | N2—H2 | 0.8600 |
C10—H10 | 0.9300 | N3—N4 | 1.376 (3) |
C11—C16 | 1.374 (4) | N5—H5A | 0.8600 |
C11—C12 | 1.377 (4) | N6—H6 | 0.8600 |
C11—C17 | 1.489 (4) | N7—N8 | 1.377 (3) |
| | | |
C2—C1—C6 | 115.6 (2) | C15—C14—C13 | 120.8 (4) |
C2—C1—C7 | 123.0 (3) | C15—C14—H14 | 119.6 |
C6—C1—C7 | 121.3 (3) | C13—C14—H14 | 119.6 |
F2—C2—C3 | 119.1 (3) | C14—C15—C16 | 118.5 (4) |
F2—C2—C1 | 117.2 (2) | C14—C15—H15 | 120.7 |
C3—C2—C1 | 123.7 (3) | C16—C15—H15 | 120.7 |
C4—C3—C2 | 118.2 (3) | F3—C16—C15 | 118.2 (3) |
C4—C3—H3 | 120.9 | F3—C16—C11 | 117.9 (3) |
C2—C3—H3 | 120.9 | C15—C16—C11 | 123.8 (3) |
C3—C4—C5 | 120.9 (3) | O3—C17—N5 | 123.9 (3) |
C3—C4—H4 | 119.6 | O3—C17—C11 | 122.3 (2) |
C5—C4—H4 | 119.6 | N5—C17—C11 | 113.8 (2) |
C6—C5—C4 | 118.6 (3) | O4—C18—N6 | 123.5 (2) |
C6—C5—H5 | 120.7 | O4—C18—N5 | 120.9 (2) |
C4—C5—H5 | 120.7 | N6—C18—N5 | 115.5 (2) |
F1—C6—C5 | 119.7 (3) | N7—C19—N6 | 120.7 (2) |
F1—C6—C1 | 117.3 (3) | N7—C19—S2 | 114.77 (19) |
C5—C6—C1 | 123.0 (3) | N6—C19—S2 | 124.51 (18) |
O1—C7—N1 | 124.2 (2) | N8—C20—S2 | 114.6 (2) |
O1—C7—C1 | 121.3 (2) | N8—C20—H20 | 122.7 |
N1—C7—C1 | 114.5 (2) | S2—C20—H20 | 122.7 |
O2—C8—N2 | 123.0 (2) | C7—N1—C8 | 128.1 (2) |
O2—C8—N1 | 121.2 (2) | C7—N1—H1 | 115.9 |
N2—C8—N1 | 115.8 (2) | C8—N1—H1 | 115.9 |
N3—C9—N2 | 119.8 (2) | C8—N2—C9 | 122.8 (2) |
N3—C9—S1 | 115.84 (18) | C8—N2—H2 | 118.6 |
N2—C9—S1 | 124.34 (17) | C9—N2—H2 | 118.6 |
N4—C10—S1 | 115.7 (2) | C9—N3—N4 | 110.6 (2) |
N4—C10—H10 | 122.1 | C10—N4—N3 | 112.4 (2) |
S1—C10—H10 | 122.1 | C17—N5—C18 | 128.0 (2) |
C16—C11—C12 | 115.3 (3) | C17—N5—H5A | 116.0 |
C16—C11—C17 | 123.2 (3) | C18—N5—H5A | 116.0 |
C12—C11—C17 | 121.5 (3) | C18—N6—C19 | 123.7 (2) |
F4—C12—C11 | 117.7 (3) | C18—N6—H6 | 118.1 |
F4—C12—C13 | 119.3 (3) | C19—N6—H6 | 118.1 |
C11—C12—C13 | 122.9 (3) | C19—N7—N8 | 111.4 (2) |
C14—C13—C12 | 118.5 (4) | C20—N8—N7 | 113.1 (2) |
C14—C13—H13 | 120.7 | C10—S1—C9 | 85.40 (13) |
C12—C13—H13 | 120.7 | C19—S2—C20 | 86.15 (13) |
| | | |
C6—C1—C2—F2 | 178.9 (2) | C12—C11—C17—O3 | 57.2 (4) |
C7—C1—C2—F2 | −4.7 (4) | C16—C11—C17—N5 | 57.5 (4) |
C6—C1—C2—C3 | −1.3 (4) | C12—C11—C17—N5 | −122.9 (3) |
C7—C1—C2—C3 | 175.2 (3) | O1—C7—N1—C8 | 1.5 (5) |
F2—C2—C3—C4 | −179.0 (3) | C1—C7—N1—C8 | −179.7 (2) |
C1—C2—C3—C4 | 1.2 (4) | O2—C8—N1—C7 | 176.0 (3) |
C2—C3—C4—C5 | −0.2 (5) | N2—C8—N1—C7 | −3.6 (4) |
C3—C4—C5—C6 | −0.7 (5) | O2—C8—N2—C9 | 3.6 (4) |
C4—C5—C6—F1 | −179.5 (3) | N1—C8—N2—C9 | −176.8 (2) |
C4—C5—C6—C1 | 0.7 (5) | N3—C9—N2—C8 | −179.0 (2) |
C2—C1—C6—F1 | −179.6 (2) | S1—C9—N2—C8 | 2.8 (3) |
C7—C1—C6—F1 | 3.9 (4) | N2—C9—N3—N4 | −178.2 (2) |
C2—C1—C6—C5 | 0.3 (4) | S1—C9—N3—N4 | 0.1 (3) |
C7—C1—C6—C5 | −176.2 (3) | S1—C10—N4—N3 | 0.5 (3) |
C2—C1—C7—O1 | −106.0 (4) | C9—N3—N4—C10 | −0.4 (3) |
C6—C1—C7—O1 | 70.2 (4) | O3—C17—N5—C18 | 8.9 (5) |
C2—C1—C7—N1 | 75.1 (3) | C11—C17—N5—C18 | −170.9 (3) |
C6—C1—C7—N1 | −108.7 (3) | O4—C18—N5—C17 | 173.2 (3) |
C16—C11—C12—F4 | 178.9 (3) | N6—C18—N5—C17 | −6.0 (4) |
C17—C11—C12—F4 | −0.8 (4) | O4—C18—N6—C19 | −9.1 (4) |
C16—C11—C12—C13 | −2.9 (4) | N5—C18—N6—C19 | 170.2 (2) |
C17—C11—C12—C13 | 177.5 (3) | N7—C19—N6—C18 | −173.0 (3) |
F4—C12—C13—C14 | −179.4 (3) | S2—C19—N6—C18 | 6.7 (4) |
C11—C12—C13—C14 | 2.4 (5) | N6—C19—N7—N8 | 178.9 (2) |
C12—C13—C14—C15 | −0.1 (6) | S2—C19—N7—N8 | −1.0 (3) |
C13—C14—C15—C16 | −1.4 (6) | S2—C20—N8—N7 | −0.4 (4) |
C14—C15—C16—F3 | −179.7 (3) | C19—N7—N8—C20 | 0.9 (4) |
C14—C15—C16—C11 | 0.8 (5) | N4—C10—S1—C9 | −0.3 (3) |
C12—C11—C16—F3 | −178.2 (2) | N3—C9—S1—C10 | 0.1 (2) |
C17—C11—C16—F3 | 1.4 (4) | N2—C9—S1—C10 | 178.4 (2) |
C12—C11—C16—C15 | 1.3 (4) | N7—C19—S2—C20 | 0.6 (2) |
C17—C11—C16—C15 | −179.1 (3) | N6—C19—S2—C20 | −179.2 (3) |
C16—C11—C17—O3 | −122.3 (3) | N8—C20—S2—C19 | −0.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6···O3 | 0.86 | 1.99 | 2.653 (3) | 133 |
N2—H2···O1 | 0.86 | 1.97 | 2.648 (3) | 134 |
N5—H5A···N8i | 0.86 | 2.00 | 2.860 (3) | 175 |
N1—H1···N4ii | 0.86 | 2.02 | 2.875 (3) | 178 |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z−1/2. |