The title compound, C
14H
13ClN
2OS, shows antibacterial and antifungal activities. In the asymmetric unit there are two independent molecules, the dihedral angles between the thiophene moiety and the 2-chlorophenyl ring being 1.1 (3)° and 6.7 (3)°. There are intra- and intermolecular N—H
O hydrogen bonds.
Supporting information
CCDC reference: 236104
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.057
- wR factor = 0.130
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT352_ALERT_3_C Short N-H Bond (0.87A) N1 - H1N ... 0.75 Ang.
PLAT352_ALERT_3_C Short N-H Bond (0.87A) N2 - H2N ... 0.74 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C14 H13 Cl N2 O S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).
Crystal data top
C14H13ClN2OS | F(000) = 1216 |
Mr = 292.78 | Dx = 1.469 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 600 reflections |
a = 9.939 (3) Å | θ = 2.0–24.5° |
b = 29.449 (8) Å | µ = 0.44 mm−1 |
c = 9.747 (3) Å | T = 293 K |
β = 111.912 (4)° | Block, yellow |
V = 2646.8 (14) Å3 | 0.60 × 0.40 × 0.35 mm |
Z = 8 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5215 independent reflections |
Radiation source: fine-focus sealed tube | 4005 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 26.4°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −11→12 |
Tmin = 0.779, Tmax = 0.862 | k = −36→36 |
19431 measured reflections | l = −12→11 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | All H-atom parameters refined |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0488P)2 + 1.7113P] where P = (Fo2 + 2Fc2)/3 |
5215 reflections | (Δ/σ)max < 0.001 |
447 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.23 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 | |
S1 | 0.66111 (9) | 0.18736 (3) | 0.86308 (10) | 0.0523 (2) | |
S2 | 1.16488 (9) | 0.05914 (3) | 0.90025 (10) | 0.0499 (2) | |
Cl1 | 1.10786 (10) | 0.33831 (3) | 0.65822 (11) | 0.0598 (3) | |
Cl2 | 1.55132 (11) | −0.10306 (3) | 0.65134 (13) | 0.0731 (3) | |
O1 | 1.0466 (2) | 0.16585 (6) | 0.7236 (3) | 0.0568 (6) | |
O2 | 1.5621 (2) | 0.06872 (7) | 0.7754 (3) | 0.0543 (6) | |
N1 | 1.0436 (3) | 0.24232 (8) | 0.6889 (3) | 0.0442 (6) | |
N2 | 1.5368 (3) | −0.00714 (9) | 0.7300 (3) | 0.0438 (6) | |
N3 | 1.3497 (4) | 0.11400 (9) | 0.8383 (4) | 0.0566 (8) | |
N4 | 0.8251 (4) | 0.12740 (9) | 0.7893 (4) | 0.0585 (8) | |
C1 | 0.7182 (5) | 0.32347 (12) | 0.8415 (6) | 0.0677 (11) | |
C2 | 0.6359 (4) | 0.28646 (11) | 0.8903 (4) | 0.0487 (8) | |
C3 | 0.6990 (3) | 0.24427 (10) | 0.8533 (3) | 0.0445 (7) | |
C4 | 0.8112 (3) | 0.25097 (9) | 0.8099 (3) | 0.0377 (6) | |
C5 | 0.8415 (4) | 0.30091 (9) | 0.8068 (4) | 0.0446 (7) | |
C6 | 0.8749 (3) | 0.20948 (8) | 0.7819 (3) | 0.0362 (6) | |
C7 | 0.8014 (3) | 0.17194 (9) | 0.8061 (3) | 0.0413 (7) | |
C8 | 0.9940 (3) | 0.20348 (9) | 0.7312 (3) | 0.0382 (6) | |
C9 | 1.1534 (3) | 0.24807 (9) | 0.6335 (3) | 0.0381 (6) | |
C10 | 1.2228 (3) | 0.21268 (11) | 0.5914 (4) | 0.0466 (7) | |
C11 | 1.3300 (4) | 0.22133 (13) | 0.5378 (4) | 0.0563 (9) | |
C12 | 1.3703 (4) | 0.26535 (13) | 0.5228 (4) | 0.0594 (9) | |
C13 | 1.3025 (4) | 0.30110 (12) | 0.5615 (4) | 0.0530 (8) | |
C14 | 1.1953 (3) | 0.29241 (10) | 0.6154 (3) | 0.0421 (7) | |
C15 | 1.1742 (4) | −0.07771 (11) | 0.8552 (5) | 0.0530 (9) | |
C16 | 1.3107 (3) | −0.05949 (9) | 0.8333 (4) | 0.0405 (7) | |
C17 | 1.2976 (3) | −0.00883 (8) | 0.8446 (3) | 0.0334 (6) | |
C18 | 1.1074 (4) | −0.03857 (10) | 0.9140 (4) | 0.0479 (8) | |
C19 | 1.1858 (3) | 0.00115 (9) | 0.8843 (3) | 0.0394 (6) | |
C20 | 1.3760 (3) | 0.03065 (8) | 0.8252 (3) | 0.0338 (6) | |
C21 | 1.3120 (3) | 0.07004 (9) | 0.8493 (3) | 0.0403 (7) | |
C22 | 1.4981 (3) | 0.03288 (9) | 0.7766 (3) | 0.0374 (6) | |
C23 | 1.6385 (3) | −0.01548 (10) | 0.6646 (3) | 0.0404 (7) | |
C24 | 1.7204 (4) | 0.01843 (13) | 0.6320 (4) | 0.0554 (9) | |
C25 | 1.8171 (4) | 0.00773 (15) | 0.5665 (4) | 0.0629 (10) | |
C26 | 1.8350 (4) | −0.03602 (15) | 0.5294 (4) | 0.0636 (10) | |
C27 | 1.7542 (4) | −0.07019 (13) | 0.5583 (4) | 0.0580 (9) | |
C28 | 1.6569 (3) | −0.05991 (10) | 0.6242 (3) | 0.0462 (7) | |
H1A | 0.761 (4) | 0.3470 (15) | 0.916 (4) | 0.088 (14)* | |
H1B | 0.653 (4) | 0.3373 (14) | 0.755 (5) | 0.086 (14)* | |
H1N | 1.001 (4) | 0.2627 (11) | 0.695 (4) | 0.050 (10)* | |
H2A | 0.661 (3) | 0.2878 (10) | 0.995 (4) | 0.050 (9)* | |
H2B | 0.534 (4) | 0.2879 (10) | 0.835 (3) | 0.047 (9)* | |
H2N | 1.490 (4) | −0.0262 (11) | 0.733 (4) | 0.055 (11)* | |
H5A | 0.939 (4) | 0.3093 (11) | 0.881 (4) | 0.061 (10)* | |
H5B | 0.836 (3) | 0.3111 (10) | 0.710 (3) | 0.047 (8)* | |
H10 | 1.195 (3) | 0.1826 (11) | 0.598 (3) | 0.048 (8)* | |
H11 | 1.376 (4) | 0.1983 (13) | 0.507 (4) | 0.080 (12)* | |
H12 | 1.437 (3) | 0.2688 (10) | 0.483 (3) | 0.046 (8)* | |
H13 | 1.327 (4) | 0.3339 (12) | 0.554 (4) | 0.069 (10)* | |
H14N | 0.897 (5) | 0.1210 (13) | 0.764 (4) | 0.081 (14)* | |
H15A | 1.195 (4) | −0.1020 (13) | 0.913 (4) | 0.069 (11)* | |
H15B | 1.109 (4) | −0.0859 (12) | 0.757 (4) | 0.069 (11)* | |
H16A | 1.402 (4) | −0.0706 (10) | 0.909 (4) | 0.053 (9)* | |
H16B | 1.311 (3) | −0.0682 (9) | 0.744 (3) | 0.039 (8)* | |
H18A | 1.006 (4) | −0.0362 (11) | 0.860 (4) | 0.057 (10)* | |
H18B | 1.128 (3) | −0.0413 (10) | 1.021 (4) | 0.052 (9)* | |
H24 | 1.704 (4) | 0.0471 (12) | 0.655 (4) | 0.059 (10)* | |
H24N | 0.767 (4) | 0.1070 (13) | 0.797 (4) | 0.071 (12)* | |
H25 | 1.870 (4) | 0.0313 (13) | 0.548 (4) | 0.080 (12)* | |
H26 | 1.895 (4) | −0.0443 (12) | 0.480 (4) | 0.069 (11)* | |
H27 | 1.763 (4) | −0.1022 (12) | 0.532 (4) | 0.067 (11)* | |
H31N | 1.416 (4) | 0.1184 (11) | 0.799 (4) | 0.055 (10)* | |
H32N | 1.283 (4) | 0.1327 (12) | 0.812 (4) | 0.065 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0458 (4) | 0.0445 (4) | 0.0761 (6) | −0.0037 (3) | 0.0335 (4) | 0.0103 (4) |
S2 | 0.0524 (5) | 0.0377 (4) | 0.0725 (6) | 0.0068 (3) | 0.0382 (4) | −0.0001 (4) |
Cl1 | 0.0659 (5) | 0.0345 (4) | 0.0922 (7) | −0.0015 (3) | 0.0448 (5) | 0.0045 (4) |
Cl2 | 0.0805 (6) | 0.0379 (4) | 0.1292 (9) | 0.0020 (4) | 0.0718 (6) | −0.0029 (5) |
O1 | 0.0633 (14) | 0.0301 (11) | 0.0933 (18) | 0.0061 (10) | 0.0478 (13) | 0.0072 (11) |
O2 | 0.0541 (13) | 0.0351 (11) | 0.0848 (17) | −0.0101 (9) | 0.0386 (12) | −0.0044 (10) |
N1 | 0.0457 (15) | 0.0294 (13) | 0.0680 (18) | 0.0048 (11) | 0.0333 (14) | 0.0071 (12) |
N2 | 0.0440 (15) | 0.0352 (13) | 0.0639 (18) | −0.0082 (11) | 0.0338 (13) | −0.0058 (12) |
N3 | 0.0633 (19) | 0.0283 (13) | 0.090 (2) | 0.0016 (13) | 0.0430 (18) | −0.0003 (13) |
N4 | 0.0614 (19) | 0.0277 (13) | 0.097 (2) | −0.0056 (13) | 0.0418 (18) | 0.0041 (14) |
C1 | 0.066 (2) | 0.0434 (19) | 0.112 (4) | 0.0076 (18) | 0.055 (3) | 0.001 (2) |
C2 | 0.0431 (19) | 0.0502 (18) | 0.057 (2) | 0.0061 (14) | 0.0233 (17) | 0.0029 (15) |
C3 | 0.0397 (16) | 0.0401 (16) | 0.0578 (19) | 0.0009 (12) | 0.0226 (15) | 0.0038 (14) |
C4 | 0.0368 (15) | 0.0334 (14) | 0.0427 (16) | 0.0004 (11) | 0.0146 (13) | 0.0035 (12) |
C5 | 0.0476 (19) | 0.0304 (14) | 0.061 (2) | 0.0023 (13) | 0.0262 (17) | 0.0043 (14) |
C6 | 0.0351 (15) | 0.0297 (13) | 0.0448 (16) | 0.0000 (11) | 0.0160 (12) | 0.0054 (11) |
C7 | 0.0388 (15) | 0.0342 (14) | 0.0510 (18) | −0.0038 (12) | 0.0168 (14) | 0.0057 (12) |
C8 | 0.0399 (15) | 0.0285 (13) | 0.0477 (17) | −0.0001 (11) | 0.0178 (13) | 0.0024 (12) |
C9 | 0.0360 (15) | 0.0409 (15) | 0.0393 (16) | 0.0009 (12) | 0.0161 (13) | 0.0047 (12) |
C10 | 0.0493 (18) | 0.0436 (17) | 0.0532 (19) | 0.0055 (14) | 0.0262 (15) | 0.0029 (14) |
C11 | 0.057 (2) | 0.063 (2) | 0.058 (2) | 0.0085 (17) | 0.0318 (18) | −0.0025 (17) |
C12 | 0.053 (2) | 0.075 (2) | 0.064 (2) | −0.0036 (18) | 0.0383 (19) | 0.0020 (18) |
C13 | 0.0523 (19) | 0.059 (2) | 0.054 (2) | −0.0093 (16) | 0.0270 (16) | 0.0063 (16) |
C14 | 0.0422 (16) | 0.0406 (15) | 0.0461 (17) | 0.0000 (12) | 0.0195 (14) | 0.0041 (13) |
C15 | 0.059 (2) | 0.0385 (17) | 0.072 (3) | −0.0067 (15) | 0.037 (2) | 0.0022 (17) |
C16 | 0.0451 (18) | 0.0311 (14) | 0.0506 (19) | −0.0021 (12) | 0.0240 (15) | −0.0018 (13) |
C17 | 0.0376 (15) | 0.0275 (13) | 0.0373 (15) | 0.0002 (11) | 0.0164 (12) | 0.0012 (11) |
C18 | 0.046 (2) | 0.0461 (17) | 0.060 (2) | −0.0026 (14) | 0.0295 (17) | 0.0080 (15) |
C19 | 0.0409 (16) | 0.0348 (14) | 0.0476 (17) | 0.0026 (12) | 0.0223 (14) | 0.0014 (12) |
C20 | 0.0334 (14) | 0.0313 (13) | 0.0380 (15) | −0.0017 (11) | 0.0149 (12) | −0.0015 (11) |
C21 | 0.0420 (16) | 0.0318 (14) | 0.0483 (17) | −0.0007 (11) | 0.0183 (13) | −0.0011 (12) |
C22 | 0.0380 (15) | 0.0323 (14) | 0.0436 (16) | −0.0034 (11) | 0.0173 (13) | −0.0007 (12) |
C23 | 0.0352 (15) | 0.0468 (16) | 0.0440 (17) | −0.0042 (12) | 0.0204 (13) | −0.0035 (13) |
C24 | 0.054 (2) | 0.058 (2) | 0.064 (2) | −0.0176 (16) | 0.0333 (18) | −0.0122 (17) |
C25 | 0.051 (2) | 0.085 (3) | 0.064 (2) | −0.0185 (19) | 0.0348 (18) | −0.007 (2) |
C26 | 0.047 (2) | 0.100 (3) | 0.056 (2) | 0.0013 (19) | 0.0320 (18) | −0.004 (2) |
C27 | 0.051 (2) | 0.067 (2) | 0.066 (2) | 0.0086 (17) | 0.0334 (18) | −0.0049 (18) |
C28 | 0.0396 (16) | 0.0477 (17) | 0.0563 (19) | 0.0023 (13) | 0.0237 (14) | 0.0005 (14) |
Geometric parameters (Å, º) top
S2—C19 | 1.734 (3) | N4—C7 | 1.353 (4) |
S2—C21 | 1.741 (3) | N4—H14N | 0.86 (4) |
Cl1—C14 | 1.740 (3) | N4—H24N | 0.85 (4) |
S1—C3 | 1.728 (3) | C16—C15 | 1.547 (4) |
S1—C7 | 1.743 (3) | C16—H16B | 0.91 (3) |
Cl2—C28 | 1.730 (3) | C16—H16A | 0.98 (3) |
O2—C22 | 1.235 (3) | C6—C7 | 1.393 (4) |
O1—C8 | 1.239 (3) | C6—C4 | 1.448 (4) |
N1—C8 | 1.369 (3) | C6—C8 | 1.454 (4) |
N1—C9 | 1.396 (4) | C10—C9 | 1.394 (4) |
N1—H1N | 0.75 (3) | C10—H10 | 0.94 (3) |
C20—C21 | 1.384 (4) | C9—C14 | 1.402 (4) |
C20—C17 | 1.451 (3) | C23—C24 | 1.397 (4) |
C20—C22 | 1.459 (4) | C23—C28 | 1.398 (4) |
N2—C22 | 1.369 (4) | C18—C19 | 1.493 (4) |
N2—C23 | 1.403 (4) | C18—C15 | 1.543 (5) |
N2—H2N | 0.74 (3) | C18—H18A | 0.95 (3) |
N3—C21 | 1.363 (4) | C18—H18B | 0.99 (3) |
N3—H31N | 0.88 (4) | C2—C1 | 1.541 (5) |
N3—H32N | 0.83 (4) | C2—H2A | 0.95 (3) |
C17—C19 | 1.338 (4) | C2—H2B | 0.95 (3) |
C17—C16 | 1.505 (4) | C12—H12 | 0.89 (3) |
C3—C4 | 1.347 (4) | C1—H1A | 0.98 (4) |
C3—C2 | 1.495 (4) | C1—H1B | 0.95 (4) |
C13—C14 | 1.376 (4) | C24—C25 | 1.374 (5) |
C13—C12 | 1.377 (5) | C24—H24 | 0.90 (3) |
C13—H13 | 1.01 (4) | C28—C27 | 1.379 (4) |
C11—C10 | 1.374 (4) | C15—H15A | 0.89 (4) |
C11—C12 | 1.381 (5) | C15—H15B | 0.97 (4) |
C11—H11 | 0.93 (4) | C26—C25 | 1.367 (5) |
C5—C4 | 1.504 (4) | C26—C27 | 1.380 (5) |
C5—C1 | 1.538 (4) | C26—H26 | 0.93 (4) |
C5—H5B | 0.97 (3) | C27—H27 | 0.99 (4) |
C5—H5A | 1.00 (3) | C25—H25 | 0.93 (4) |
| | | |
C19—S2—C21 | 90.81 (13) | C20—C21—S2 | 112.5 (2) |
C3—S1—C7 | 91.05 (13) | C19—C18—C15 | 100.7 (2) |
C8—N1—C9 | 129.7 (3) | C19—C18—H18A | 111.1 (19) |
C8—N1—H1N | 111 (3) | C15—C18—H18A | 112 (2) |
C9—N1—H1N | 119 (3) | C19—C18—H18B | 110.7 (18) |
C21—C20—C17 | 110.2 (2) | C15—C18—H18B | 112.6 (18) |
C21—C20—C22 | 120.5 (2) | H18A—C18—H18B | 110 (3) |
C17—C20—C22 | 129.1 (2) | N4—C7—C6 | 128.5 (3) |
C22—N2—C23 | 129.9 (3) | N4—C7—S1 | 119.1 (2) |
C22—N2—H2N | 112 (3) | C6—C7—S1 | 112.3 (2) |
C23—N2—H2N | 118 (3) | C13—C14—C9 | 122.0 (3) |
C21—N3—H31N | 116 (2) | C13—C14—Cl1 | 118.3 (2) |
C21—N3—H32N | 116 (3) | C9—C14—Cl1 | 119.7 (2) |
H31N—N3—H32N | 114 (3) | C3—C2—C1 | 101.2 (3) |
C19—C17—C20 | 114.0 (2) | C3—C2—H2A | 109.1 (18) |
C19—C17—C16 | 110.1 (2) | C1—C2—H2A | 110.2 (19) |
C20—C17—C16 | 136.0 (2) | C3—C2—H2B | 110.8 (18) |
C4—C3—C2 | 115.2 (3) | C1—C2—H2B | 111.6 (18) |
C4—C3—S1 | 112.5 (2) | H2A—C2—H2B | 113 (3) |
C2—C3—S1 | 132.3 (2) | C13—C12—C11 | 119.9 (3) |
C14—C13—C12 | 119.4 (3) | C13—C12—H12 | 124 (2) |
C14—C13—H13 | 117 (2) | C11—C12—H12 | 117 (2) |
C12—C13—H13 | 124 (2) | O2—C22—N2 | 121.5 (3) |
C10—C11—C12 | 120.8 (3) | O2—C22—C20 | 122.4 (2) |
C10—C11—H11 | 122 (2) | N2—C22—C20 | 116.1 (2) |
C12—C11—H11 | 117 (2) | C3—C4—C6 | 114.0 (2) |
C4—C5—C1 | 103.7 (3) | C3—C4—C5 | 110.2 (2) |
C4—C5—H5B | 112.5 (18) | C6—C4—C5 | 135.8 (3) |
C1—C5—H5B | 108.7 (18) | C5—C1—C2 | 108.7 (3) |
C4—C5—H5A | 112.0 (19) | C5—C1—H1A | 108 (2) |
C1—C5—H5A | 111.6 (19) | C2—C1—H1A | 114 (2) |
H5B—C5—H5A | 108 (3) | C5—C1—H1B | 109 (3) |
C7—N4—H14N | 117 (3) | C2—C1—H1B | 108 (3) |
C7—N4—H24N | 121 (3) | H1A—C1—H1B | 109 (3) |
H14N—N4—H24N | 122 (4) | C25—C24—C23 | 120.6 (3) |
C17—C16—C15 | 103.2 (2) | C25—C24—H24 | 123 (2) |
C17—C16—H16B | 112.3 (18) | C23—C24—H24 | 116 (2) |
C15—C16—H16B | 110.5 (18) | C27—C28—C23 | 121.6 (3) |
C17—C16—H16A | 110.8 (18) | C27—C28—Cl2 | 118.7 (3) |
C15—C16—H16A | 112.8 (18) | C23—C28—Cl2 | 119.6 (2) |
H16B—C16—H16A | 107 (3) | C18—C15—C16 | 108.3 (3) |
C7—C6—C4 | 110.1 (2) | C18—C15—H15A | 113 (2) |
C7—C6—C8 | 120.4 (2) | C16—C15—H15A | 111 (2) |
C4—C6—C8 | 129.4 (2) | C18—C15—H15B | 110 (2) |
O1—C8—N1 | 121.5 (3) | C16—C15—H15B | 104 (2) |
O1—C8—C6 | 123.0 (2) | H15A—C15—H15B | 110 (3) |
N1—C8—C6 | 115.6 (2) | C25—C26—C27 | 119.3 (3) |
C11—C10—C9 | 120.8 (3) | C25—C26—H26 | 124 (2) |
C11—C10—H10 | 119.6 (19) | C27—C26—H26 | 117 (2) |
C9—C10—H10 | 119.5 (19) | C28—C27—C26 | 119.8 (3) |
C10—C9—N1 | 124.6 (3) | C28—C27—H27 | 118 (2) |
C10—C9—C14 | 117.2 (3) | C26—C27—H27 | 122 (2) |
N1—C9—C14 | 118.3 (3) | C17—C19—C18 | 115.7 (2) |
C24—C23—C28 | 117.2 (3) | C17—C19—S2 | 112.5 (2) |
C24—C23—N2 | 123.9 (3) | C18—C19—S2 | 131.7 (2) |
C28—C23—N2 | 118.9 (3) | C26—C25—C24 | 121.4 (4) |
N3—C21—C20 | 128.7 (3) | C26—C25—H25 | 121 (2) |
N3—C21—S2 | 118.9 (2) | C24—C25—H25 | 117 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H24N···O2i | 0.86 (4) | 2.27 (4) | 3.094 (5) | 162 (4) |
N3—H32N···O1 | 0.83 (4) | 2.39 (4) | 3.186 (5) | 162 (3) |
N4—H14N···O1 | 0.86 (5) | 2.13 (5) | 2.755 (5) | 129 (4) |
N3—H31N···O2 | 0.88 (4) | 2.14 (4) | 2.752 (5) | 126 (3) |
C10—H10···O1 | 0.94 (3) | 2.29 (4) | 2.883 (5) | 120 (2) |
C24—H24···O2 | 0.90 (4) | 2.24 (4) | 2.875 (5) | 127 (3) |
Symmetry code: (i) x−1, y, z. |