The principal molecule of the title compound, C22H16Cl2N4O2S2·C3H7NO, is not planar; the three benzene rings are tilted with respect to each other, with dihedral angles of 5.51 (11), 60.06 (12) and 64.33 (11)°. Intermolecular hydrogen bonding and π–π stacking help to stabilize the crystal structure.
Supporting information
CCDC reference: 295250
Key indicators
- Single-crystal X-ray study
- T = 289 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.088
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5
PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C14 .. 2.96 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
N,
N'-Bis[(4-chloroanilino)thiocarbonyl]isophthalamide
dimethylformamide solvate
top
Crystal data top
C22H16Cl2N4O2S2·C3H7NO | F(000) = 1192 |
Mr = 576.50 | Dx = 1.466 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 29 reflections |
a = 14.703 (3) Å | θ = 3.9–14.0° |
b = 8.479 (1) Å | µ = 0.45 mm−1 |
c = 21.223 (4) Å | T = 289 K |
β = 99.25 (2)° | Block, colorless |
V = 2611.4 (8) Å3 | 0.48 × 0.44 × 0.34 mm |
Z = 4 | |
Data collection top
Siemens P4 diffractometer | Rint = 0.015 |
Radiation source: normal-focus sealed tube | θmax = 26.0°, θmin = 1.4° |
Graphite monochromator | h = 0→18 |
ω scans | k = 0→10 |
5911 measured reflections | l = −26→25 |
5133 independent reflections | 3 standard reflections every 97 reflections |
3480 reflections with I > 2σ(I) | intensity decay: 6.4% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.0426P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.001 |
5133 reflections | Δρmax = 0.20 e Å−3 |
353 parameters | Δρmin = −0.22 e Å−3 |
4 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0060 (5) |
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 | |
Cl1 | 1.18465 (4) | 0.92520 (8) | 0.59524 (3) | 0.05650 (19) | |
Cl2 | −0.12768 (4) | 0.23655 (9) | 0.73115 (3) | 0.0655 (2) | |
S1 | 0.75306 (4) | 0.68526 (9) | 0.64358 (3) | 0.05198 (19) | |
S2 | 0.32065 (4) | 0.53547 (9) | 0.71124 (3) | 0.05084 (19) | |
O1 | 0.63982 (10) | 0.8399 (2) | 0.44179 (7) | 0.0629 (5) | |
O2 | 0.20390 (9) | 0.5765 (2) | 0.50030 (6) | 0.0455 (4) | |
O3 | 0.50664 (10) | 0.7138 (2) | 0.64092 (7) | 0.0530 (4) | |
N1 | 0.78318 (11) | 0.8117 (2) | 0.53348 (8) | 0.0383 (5) | |
N2 | 0.63281 (11) | 0.7476 (2) | 0.54148 (8) | 0.0368 (4) | |
N3 | 0.31539 (11) | 0.5917 (2) | 0.58846 (8) | 0.0361 (4) | |
N4 | 0.18218 (11) | 0.4852 (2) | 0.61446 (8) | 0.0405 (5) | |
N5 | 0.57773 (12) | 0.5612 (2) | 0.72202 (8) | 0.0425 (5) | |
C1 | 0.93633 (13) | 0.7912 (3) | 0.50802 (9) | 0.0349 (5) | |
H1 | 0.9108 | 0.7456 | 0.4694 | 0.042* | |
C2 | 1.03061 (13) | 0.8168 (3) | 0.52152 (10) | 0.0383 (5) | |
H2 | 1.0687 | 0.7876 | 0.4925 | 0.046* | |
C3 | 1.06661 (13) | 0.8860 (3) | 0.57855 (10) | 0.0382 (5) | |
C4 | 1.01173 (14) | 0.9305 (3) | 0.62207 (10) | 0.0449 (6) | |
H4 | 1.0376 | 0.9772 | 0.6604 | 0.054* | |
C5 | 0.91767 (14) | 0.9053 (3) | 0.60831 (10) | 0.0426 (6) | |
H5 | 0.8798 | 0.9367 | 0.6371 | 0.051* | |
C6 | 0.87999 (13) | 0.8330 (3) | 0.55145 (9) | 0.0343 (5) | |
C7 | 0.72575 (13) | 0.7518 (3) | 0.56976 (9) | 0.0350 (5) | |
C8 | 0.59422 (14) | 0.7956 (3) | 0.48162 (10) | 0.0402 (5) | |
C9 | 0.49105 (13) | 0.7917 (3) | 0.46714 (9) | 0.0323 (5) | |
C10 | 0.44824 (14) | 0.8840 (3) | 0.41691 (9) | 0.0393 (5) | |
H10 | 0.4834 | 0.9456 | 0.3937 | 0.047* | |
C11 | 0.35283 (14) | 0.8840 (3) | 0.40137 (10) | 0.0414 (5) | |
H11 | 0.3242 | 0.9440 | 0.3672 | 0.050* | |
C12 | 0.30055 (14) | 0.7954 (3) | 0.43644 (10) | 0.0391 (5) | |
H12 | 0.2367 | 0.7959 | 0.4258 | 0.047* | |
C13 | 0.34249 (13) | 0.7055 (3) | 0.48749 (9) | 0.0325 (5) | |
C14 | 0.43806 (13) | 0.7014 (3) | 0.50205 (9) | 0.0335 (5) | |
H14 | 0.4666 | 0.6382 | 0.5352 | 0.040* | |
C15 | 0.28174 (13) | 0.6173 (3) | 0.52550 (9) | 0.0350 (5) | |
C16 | 0.26808 (13) | 0.5329 (3) | 0.63630 (9) | 0.0352 (5) | |
C17 | 0.11228 (13) | 0.4279 (3) | 0.64726 (9) | 0.0339 (5) | |
C18 | 0.02238 (14) | 0.4613 (3) | 0.61952 (10) | 0.0413 (6) | |
H18 | 0.0117 | 0.5232 | 0.5829 | 0.050* | |
C19 | −0.05127 (14) | 0.4043 (3) | 0.64535 (10) | 0.0421 (6) | |
H19 | −0.1113 | 0.4276 | 0.6265 | 0.050* | |
C20 | −0.03484 (14) | 0.3126 (3) | 0.69931 (10) | 0.0402 (5) | |
C21 | 0.05404 (15) | 0.2781 (3) | 0.72745 (10) | 0.0456 (6) | |
H21 | 0.0644 | 0.2159 | 0.7640 | 0.055* | |
C22 | 0.12784 (14) | 0.3358 (3) | 0.70151 (10) | 0.0417 (6) | |
H22 | 0.1878 | 0.3127 | 0.7206 | 0.050* | |
C23 | 0.54634 (14) | 0.6952 (3) | 0.69648 (10) | 0.0445 (6) | |
H23 | 0.5546 | 0.7843 | 0.7224 | 0.053* | |
C24 | 0.57123 (19) | 0.4215 (3) | 0.68313 (12) | 0.0671 (8) | |
H24A | 0.5093 | 0.4102 | 0.6610 | 0.081* | |
H24B | 0.5874 | 0.3310 | 0.7098 | 0.081* | |
H24C | 0.6127 | 0.4301 | 0.6527 | 0.081* | |
C25 | 0.63067 (19) | 0.5539 (4) | 0.78586 (11) | 0.0760 (9) | |
H25A | 0.6929 | 0.5236 | 0.7834 | 0.091* | |
H25B | 0.6036 | 0.4777 | 0.8107 | 0.091* | |
H25C | 0.6306 | 0.6556 | 0.8057 | 0.091* | |
H1N | 0.7585 (13) | 0.830 (2) | 0.4949 (5) | 0.041 (6)* | |
H2N | 0.5962 (11) | 0.728 (2) | 0.5678 (7) | 0.033 (6)* | |
H3N | 0.3669 (9) | 0.635 (2) | 0.6034 (9) | 0.039 (6)* | |
H4N | 0.1639 (13) | 0.505 (3) | 0.5751 (5) | 0.046 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0247 (3) | 0.0714 (5) | 0.0698 (4) | −0.0062 (3) | −0.0034 (3) | 0.0021 (3) |
Cl2 | 0.0470 (4) | 0.0959 (6) | 0.0566 (4) | −0.0220 (4) | 0.0173 (3) | 0.0107 (4) |
S1 | 0.0294 (3) | 0.0834 (5) | 0.0417 (3) | −0.0018 (3) | 0.0014 (2) | 0.0162 (3) |
S2 | 0.0358 (3) | 0.0801 (5) | 0.0345 (3) | −0.0085 (3) | −0.0007 (2) | 0.0047 (3) |
O1 | 0.0328 (8) | 0.1187 (17) | 0.0371 (9) | −0.0163 (10) | 0.0051 (7) | 0.0181 (10) |
O2 | 0.0279 (7) | 0.0728 (12) | 0.0340 (8) | −0.0125 (8) | 0.0000 (6) | 0.0014 (8) |
O3 | 0.0390 (9) | 0.0791 (13) | 0.0381 (8) | −0.0038 (9) | −0.0022 (7) | 0.0074 (9) |
N1 | 0.0218 (9) | 0.0599 (13) | 0.0323 (10) | −0.0049 (9) | 0.0021 (7) | 0.0031 (10) |
N2 | 0.0204 (8) | 0.0573 (13) | 0.0330 (9) | −0.0048 (8) | 0.0057 (7) | 0.0034 (9) |
N3 | 0.0219 (9) | 0.0515 (12) | 0.0342 (9) | −0.0055 (9) | 0.0024 (7) | 0.0015 (9) |
N4 | 0.0300 (9) | 0.0604 (13) | 0.0302 (10) | −0.0092 (9) | 0.0019 (8) | 0.0067 (10) |
N5 | 0.0370 (10) | 0.0571 (14) | 0.0335 (9) | −0.0016 (10) | 0.0058 (8) | −0.0009 (10) |
C1 | 0.0280 (10) | 0.0418 (14) | 0.0343 (11) | −0.0032 (10) | 0.0028 (9) | −0.0015 (10) |
C2 | 0.0289 (10) | 0.0450 (14) | 0.0422 (12) | −0.0001 (10) | 0.0093 (9) | 0.0020 (11) |
C3 | 0.0227 (10) | 0.0441 (14) | 0.0459 (12) | −0.0016 (10) | −0.0003 (9) | 0.0075 (11) |
C4 | 0.0375 (12) | 0.0569 (16) | 0.0374 (12) | −0.0085 (12) | −0.0026 (10) | −0.0049 (11) |
C5 | 0.0333 (11) | 0.0575 (16) | 0.0380 (12) | −0.0065 (11) | 0.0085 (9) | −0.0081 (11) |
C6 | 0.0246 (10) | 0.0420 (14) | 0.0360 (11) | −0.0023 (10) | 0.0042 (9) | 0.0019 (10) |
C7 | 0.0263 (10) | 0.0414 (13) | 0.0370 (11) | −0.0013 (10) | 0.0044 (9) | −0.0033 (10) |
C8 | 0.0312 (11) | 0.0564 (16) | 0.0326 (11) | −0.0071 (11) | 0.0032 (9) | 0.0003 (11) |
C9 | 0.0255 (10) | 0.0431 (13) | 0.0279 (10) | −0.0022 (10) | 0.0025 (8) | −0.0033 (10) |
C10 | 0.0375 (12) | 0.0475 (14) | 0.0334 (11) | −0.0041 (11) | 0.0075 (9) | 0.0016 (11) |
C11 | 0.0389 (12) | 0.0488 (15) | 0.0355 (11) | 0.0049 (11) | 0.0028 (10) | 0.0069 (11) |
C12 | 0.0266 (10) | 0.0524 (15) | 0.0367 (11) | 0.0036 (10) | 0.0003 (9) | 0.0007 (11) |
C13 | 0.0256 (10) | 0.0410 (13) | 0.0304 (10) | −0.0019 (10) | 0.0030 (8) | −0.0037 (10) |
C14 | 0.0295 (10) | 0.0434 (14) | 0.0266 (10) | −0.0004 (10) | 0.0012 (8) | 0.0015 (10) |
C15 | 0.0264 (10) | 0.0437 (14) | 0.0342 (11) | 0.0009 (10) | 0.0029 (9) | −0.0027 (10) |
C16 | 0.0274 (10) | 0.0405 (13) | 0.0374 (11) | 0.0007 (10) | 0.0038 (9) | −0.0009 (10) |
C17 | 0.0294 (10) | 0.0419 (13) | 0.0305 (10) | −0.0037 (10) | 0.0052 (8) | −0.0018 (10) |
C18 | 0.0358 (12) | 0.0497 (15) | 0.0368 (12) | −0.0025 (11) | 0.0008 (9) | 0.0104 (11) |
C19 | 0.0283 (11) | 0.0544 (16) | 0.0428 (12) | −0.0003 (11) | 0.0037 (9) | 0.0021 (11) |
C20 | 0.0338 (11) | 0.0488 (15) | 0.0397 (12) | −0.0085 (11) | 0.0105 (9) | −0.0034 (11) |
C21 | 0.0460 (13) | 0.0543 (16) | 0.0354 (11) | −0.0063 (12) | 0.0036 (10) | 0.0124 (11) |
C22 | 0.0331 (11) | 0.0510 (15) | 0.0391 (12) | −0.0024 (11) | −0.0002 (9) | 0.0073 (11) |
C23 | 0.0330 (12) | 0.0635 (18) | 0.0376 (12) | −0.0042 (12) | 0.0077 (10) | −0.0096 (12) |
C24 | 0.086 (2) | 0.0552 (18) | 0.0652 (17) | −0.0051 (16) | 0.0265 (15) | −0.0024 (15) |
C25 | 0.0751 (19) | 0.100 (2) | 0.0452 (15) | −0.0072 (19) | −0.0136 (13) | 0.0158 (16) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.746 (2) | C5—H5 | 0.9300 |
Cl2—C20 | 1.741 (2) | C8—C9 | 1.499 (3) |
S1—C7 | 1.653 (2) | C9—C14 | 1.388 (3) |
S2—C16 | 1.653 (2) | C9—C10 | 1.389 (3) |
O1—C8 | 1.220 (2) | C10—C11 | 1.389 (3) |
O2—C15 | 1.232 (2) | C10—H10 | 0.9300 |
O3—C23 | 1.239 (2) | C11—C12 | 1.376 (3) |
N1—C7 | 1.331 (3) | C11—H11 | 0.9300 |
N1—C6 | 1.425 (2) | C12—C13 | 1.386 (3) |
N1—H1N | 0.855 (9) | C12—H12 | 0.9300 |
N2—C8 | 1.368 (3) | C13—C14 | 1.390 (3) |
N2—C7 | 1.402 (2) | C13—C15 | 1.496 (3) |
N2—H2N | 0.853 (9) | C14—H14 | 0.9300 |
N3—C15 | 1.366 (2) | C17—C22 | 1.379 (3) |
N3—C16 | 1.411 (3) | C17—C18 | 1.387 (3) |
N3—H3N | 0.854 (9) | C18—C19 | 1.377 (3) |
N4—C16 | 1.336 (2) | C18—H18 | 0.9300 |
N4—C17 | 1.417 (2) | C19—C20 | 1.373 (3) |
N4—H4N | 0.853 (9) | C19—H19 | 0.9300 |
N5—C23 | 1.310 (3) | C20—C21 | 1.378 (3) |
N5—C24 | 1.438 (3) | C21—C22 | 1.383 (3) |
N5—C25 | 1.451 (3) | C21—H21 | 0.9300 |
C1—C6 | 1.381 (3) | C22—H22 | 0.9300 |
C1—C2 | 1.387 (3) | C23—H23 | 0.9300 |
C1—H1 | 0.9300 | C24—H24A | 0.9600 |
C2—C3 | 1.372 (3) | C24—H24B | 0.9600 |
C2—H2 | 0.9300 | C24—H24C | 0.9600 |
C3—C4 | 1.373 (3) | C25—H25A | 0.9600 |
C4—C5 | 1.383 (3) | C25—H25B | 0.9600 |
C4—H4 | 0.9300 | C25—H25C | 0.9600 |
C5—C6 | 1.387 (3) | | |
| | | |
C7—N1—C6 | 126.36 (17) | C11—C12—C13 | 120.41 (19) |
C7—N1—H1N | 114.3 (14) | C11—C12—H12 | 119.8 |
C6—N1—H1N | 119.1 (14) | C13—C12—H12 | 119.8 |
C8—N2—C7 | 128.35 (18) | C12—C13—C14 | 119.62 (19) |
C8—N2—H2N | 117.1 (13) | C12—C13—C15 | 117.86 (17) |
C7—N2—H2N | 113.5 (13) | C14—C13—C15 | 122.51 (18) |
C15—N3—C16 | 128.13 (17) | C9—C14—C13 | 120.13 (19) |
C15—N3—H3N | 117.1 (14) | C9—C14—H14 | 119.9 |
C16—N3—H3N | 113.2 (13) | C13—C14—H14 | 119.9 |
C16—N4—C17 | 130.79 (17) | O2—C15—N3 | 123.04 (19) |
C16—N4—H4N | 114.3 (14) | O2—C15—C13 | 119.96 (18) |
C17—N4—H4N | 114.3 (14) | N3—C15—C13 | 116.95 (17) |
C23—N5—C24 | 119.37 (19) | N4—C16—N3 | 113.90 (17) |
C23—N5—C25 | 121.6 (2) | N4—C16—S2 | 127.41 (16) |
C24—N5—C25 | 118.5 (2) | N3—C16—S2 | 118.65 (14) |
C6—C1—C2 | 120.58 (19) | C22—C17—C18 | 119.26 (19) |
C6—C1—H1 | 119.7 | C22—C17—N4 | 124.63 (18) |
C2—C1—H1 | 119.7 | C18—C17—N4 | 116.00 (18) |
C3—C2—C1 | 118.70 (19) | C19—C18—C17 | 121.1 (2) |
C3—C2—H2 | 120.7 | C19—C18—H18 | 119.5 |
C1—C2—H2 | 120.7 | C17—C18—H18 | 119.5 |
C2—C3—C4 | 121.70 (18) | C20—C19—C18 | 119.1 (2) |
C2—C3—Cl1 | 119.34 (17) | C20—C19—H19 | 120.4 |
C4—C3—Cl1 | 118.91 (17) | C18—C19—H19 | 120.4 |
C3—C4—C5 | 119.4 (2) | C19—C20—C21 | 120.6 (2) |
C3—C4—H4 | 120.3 | C19—C20—Cl2 | 119.31 (16) |
C5—C4—H4 | 120.3 | C21—C20—Cl2 | 120.09 (17) |
C4—C5—C6 | 119.9 (2) | C20—C21—C22 | 120.2 (2) |
C4—C5—H5 | 120.1 | C20—C21—H21 | 119.9 |
C6—C5—H5 | 120.1 | C22—C21—H21 | 119.9 |
C1—C6—C5 | 119.71 (18) | C17—C22—C21 | 119.8 (2) |
C1—C6—N1 | 117.99 (18) | C17—C22—H22 | 120.1 |
C5—C6—N1 | 122.09 (18) | C21—C22—H22 | 120.1 |
N1—C7—N2 | 115.30 (18) | O3—C23—N5 | 125.8 (2) |
N1—C7—S1 | 126.75 (15) | O3—C23—H23 | 117.1 |
N2—C7—S1 | 117.94 (15) | N5—C23—H23 | 117.1 |
O1—C8—N2 | 122.91 (18) | N5—C24—H24A | 109.5 |
O1—C8—C9 | 121.05 (18) | N5—C24—H24B | 109.5 |
N2—C8—C9 | 116.04 (18) | H24A—C24—H24B | 109.5 |
C14—C9—C10 | 119.75 (18) | N5—C24—H24C | 109.5 |
C14—C9—C8 | 122.64 (18) | H24A—C24—H24C | 109.5 |
C10—C9—C8 | 117.61 (18) | H24B—C24—H24C | 109.5 |
C11—C10—C9 | 119.9 (2) | N5—C25—H25A | 109.5 |
C11—C10—H10 | 120.1 | N5—C25—H25B | 109.5 |
C9—C10—H10 | 120.1 | H25A—C25—H25B | 109.5 |
C12—C11—C10 | 120.2 (2) | N5—C25—H25C | 109.5 |
C12—C11—H11 | 119.9 | H25A—C25—H25C | 109.5 |
C10—C11—H11 | 119.9 | H25B—C25—H25C | 109.5 |
| | | |
C6—C1—C2—C3 | −0.7 (3) | C10—C9—C14—C13 | −1.1 (3) |
C1—C2—C3—C4 | −0.2 (3) | C8—C9—C14—C13 | 178.3 (2) |
C1—C2—C3—Cl1 | −177.86 (17) | C12—C13—C14—C9 | 2.4 (3) |
C2—C3—C4—C5 | 0.0 (4) | C15—C13—C14—C9 | −176.82 (19) |
Cl1—C3—C4—C5 | 177.66 (18) | C16—N3—C15—O2 | −7.1 (4) |
C3—C4—C5—C6 | 1.1 (4) | C16—N3—C15—C13 | 170.1 (2) |
C2—C1—C6—C5 | 1.8 (3) | C12—C13—C15—O2 | 26.8 (3) |
C2—C1—C6—N1 | 176.7 (2) | C14—C13—C15—O2 | −154.0 (2) |
C4—C5—C6—C1 | −2.0 (3) | C12—C13—C15—N3 | −150.6 (2) |
C4—C5—C6—N1 | −176.7 (2) | C14—C13—C15—N3 | 28.7 (3) |
C7—N1—C6—C1 | 136.3 (2) | C17—N4—C16—N3 | −176.3 (2) |
C7—N1—C6—C5 | −48.9 (3) | C17—N4—C16—S2 | 1.4 (4) |
C6—N1—C7—N2 | 178.2 (2) | C15—N3—C16—N4 | 6.1 (3) |
C6—N1—C7—S1 | −1.2 (3) | C15—N3—C16—S2 | −171.77 (18) |
C8—N2—C7—N1 | 0.6 (3) | C16—N4—C17—C22 | −35.0 (4) |
C8—N2—C7—S1 | 180.00 (19) | C16—N4—C17—C18 | 148.8 (2) |
C7—N2—C8—O1 | 5.9 (4) | C22—C17—C18—C19 | 0.1 (3) |
C7—N2—C8—C9 | −174.0 (2) | N4—C17—C18—C19 | 176.5 (2) |
O1—C8—C9—C14 | 160.4 (2) | C17—C18—C19—C20 | −0.2 (4) |
N2—C8—C9—C14 | −19.8 (3) | C18—C19—C20—C21 | 0.2 (4) |
O1—C8—C9—C10 | −20.2 (3) | C18—C19—C20—Cl2 | −178.57 (18) |
N2—C8—C9—C10 | 159.7 (2) | C19—C20—C21—C22 | 0.0 (4) |
C14—C9—C10—C11 | −0.8 (3) | Cl2—C20—C21—C22 | 178.72 (18) |
C8—C9—C10—C11 | 179.7 (2) | C18—C17—C22—C21 | 0.1 (3) |
C9—C10—C11—C12 | 1.4 (3) | N4—C17—C22—C21 | −176.0 (2) |
C10—C11—C12—C13 | 0.0 (3) | C20—C21—C22—C17 | −0.1 (4) |
C11—C12—C13—C14 | −1.9 (3) | C24—N5—C23—O3 | 3.4 (3) |
C11—C12—C13—C15 | 177.4 (2) | C25—N5—C23—O3 | 174.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.86 (1) | 1.92 (2) | 2.640 (2) | 141 (2) |
N2—H2N···O3 | 0.85 (1) | 2.19 (1) | 3.039 (2) | 171 (2) |
N3—H3N···O3 | 0.85 (1) | 2.19 (1) | 3.035 (2) | 172 (2) |
N4—H4N···O2 | 0.85 (1) | 1.88 (1) | 2.612 (2) | 143 (2) |