
The two symmetry-independent molecules of the title compound, C13H11ClN2O3S, are linked by N—H
Os (s = sulfonyl) and N—H
Oh (h = hydroxy) hydrogen bonds to furnish a chain that propagates along the a axis of the monoclinic unit cell.


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011907/hb2325sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011907/hb2325Isup2.hkl |
CCDC reference: 643013
Computing details top
Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
2'-(5-Bromo-2-hydroxybenzylidene)benzenesulfonohydrazide top
Crystal data top
C13H11BrN2O3S | F(000) = 1424 |
Mr = 355.21 | Dx = 1.695 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8789 reflections |
a = 11.6084 (2) Å | θ = 2.3–29.8° |
b = 14.5141 (2) Å | µ = 3.11 mm−1 |
c = 17.3216 (2) Å | T = 173 K |
β = 107.416 (1)° | Block, yellow |
V = 2784.65 (7) Å3 | 0.25 × 0.21 × 0.13 mm |
Z = 8 |
Data collection top
Bruker APEXII diffractometer | 6377 independent reflections |
Radiation source: medium-focus sealed tube | 5044 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
φ and ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.568, Tmax = 0.688 | k = −18→18 |
53670 measured reflections | l = −22→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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0657P)2] where P = (Fo2 + 2Fc2)/3 |
6377 reflections | (Δ/σ)max = 0.001 |
363 parameters | Δρmax = 1.26 e Å−3 |
0 restraints | Δρmin = −1.22 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br1 | 0.56285 (3) | 0.65277 (2) | 0.814002 (18) | 0.04416 (11) | |
Br2 | 0.20668 (3) | 0.64910 (2) | −0.00042 (2) | 0.04955 (12) | |
S1 | 0.17312 (6) | 0.59244 (4) | 0.28106 (4) | 0.02619 (15) | |
S2 | 0.86013 (5) | 0.61415 (4) | 0.43572 (4) | 0.02182 (13) | |
O1 | 0.52836 (17) | 0.61489 (14) | 0.46119 (11) | 0.0341 (4) | |
H1O | 0.4569 | 0.6061 | 0.4323 | 0.051* | |
O2 | 0.28572 (19) | 0.56649 (12) | 0.27068 (12) | 0.0383 (5) | |
O3 | 0.06336 (19) | 0.54602 (12) | 0.23904 (12) | 0.0406 (5) | |
O4 | 0.74262 (18) | 0.61147 (16) | 0.15618 (12) | 0.0420 (5) | |
H4O | 0.7598 | 0.6031 | 0.2063 | 0.063* | |
O5 | 0.94116 (15) | 0.57559 (12) | 0.39612 (11) | 0.0294 (4) | |
O6 | 0.86399 (16) | 0.58565 (11) | 0.51537 (10) | 0.0277 (4) | |
N1 | 0.29682 (19) | 0.59772 (13) | 0.43076 (13) | 0.0261 (4) | |
N2 | 0.18622 (19) | 0.57766 (14) | 0.37665 (12) | 0.0276 (5) | |
H2N | 0.1256 | 0.5578 | 0.3928 | 0.033* | |
N3 | 0.69483 (19) | 0.60071 (13) | 0.29775 (12) | 0.0243 (4) | |
N4 | 0.72265 (18) | 0.58623 (13) | 0.38068 (12) | 0.0250 (4) | |
H4N | 0.6695 | 0.5633 | 0.4026 | 0.030* | |
C1 | 0.5312 (2) | 0.62262 (16) | 0.54021 (16) | 0.0267 (5) | |
C2 | 0.6427 (3) | 0.63321 (18) | 0.59825 (18) | 0.0318 (6) | |
H2 | 0.7138 | 0.6341 | 0.5819 | 0.038* | |
C3 | 0.6519 (3) | 0.64242 (16) | 0.67872 (18) | 0.0322 (6) | |
H3 | 0.7286 | 0.6500 | 0.7178 | 0.039* | |
C4 | 0.5477 (3) | 0.64055 (16) | 0.70223 (17) | 0.0297 (6) | |
C5 | 0.4357 (2) | 0.62875 (17) | 0.64609 (16) | 0.0293 (6) | |
H5 | 0.3654 | 0.6267 | 0.6634 | 0.035* | |
C6 | 0.4254 (2) | 0.61980 (16) | 0.56420 (16) | 0.0255 (5) | |
C7 | 0.3064 (2) | 0.60483 (16) | 0.50610 (15) | 0.0268 (5) | |
H7 | 0.2369 | 0.6004 | 0.5241 | 0.032* | |
C8 | 0.1519 (2) | 0.71070 (16) | 0.25983 (14) | 0.0233 (5) | |
C9 | 0.0423 (3) | 0.74171 (19) | 0.20901 (16) | 0.0368 (6) | |
H9 | −0.0216 | 0.6998 | 0.1859 | 0.044* | |
C10 | 0.0284 (3) | 0.8352 (2) | 0.1928 (2) | 0.0485 (8) | |
H10 | −0.0459 | 0.8576 | 0.1579 | 0.058* | |
C11 | 0.1207 (3) | 0.89599 (19) | 0.22662 (18) | 0.0380 (7) | |
H11 | 0.1098 | 0.9600 | 0.2151 | 0.046* | |
C12 | 0.2282 (3) | 0.86437 (17) | 0.27677 (19) | 0.0365 (7) | |
H12 | 0.2915 | 0.9065 | 0.3004 | 0.044* | |
C13 | 0.2449 (2) | 0.77090 (17) | 0.29320 (17) | 0.0327 (6) | |
H13 | 0.3199 | 0.7487 | 0.3272 | 0.039* | |
C14 | 0.6204 (2) | 0.61589 (18) | 0.12340 (16) | 0.0291 (5) | |
C15 | 0.5746 (3) | 0.6236 (2) | 0.04012 (18) | 0.0397 (7) | |
H15 | 0.6282 | 0.6227 | 0.0081 | 0.048* | |
C16 | 0.4518 (3) | 0.63254 (19) | 0.00296 (18) | 0.0385 (7) | |
H16 | 0.4210 | 0.6382 | −0.0542 | 0.046* | |
C17 | 0.3741 (2) | 0.63311 (17) | 0.05044 (17) | 0.0316 (6) | |
C18 | 0.4175 (2) | 0.62199 (18) | 0.13270 (17) | 0.0318 (6) | |
H18 | 0.3628 | 0.6201 | 0.1640 | 0.038* | |
C19 | 0.5413 (2) | 0.61339 (16) | 0.17095 (15) | 0.0258 (5) | |
C20 | 0.5825 (2) | 0.60264 (16) | 0.25810 (15) | 0.0268 (5) | |
H20 | 0.5245 | 0.5969 | 0.2866 | 0.032* | |
C21 | 0.8752 (2) | 0.73471 (15) | 0.43386 (14) | 0.0226 (5) | |
C22 | 0.9108 (2) | 0.77385 (17) | 0.37144 (15) | 0.0278 (5) | |
H22 | 0.9278 | 0.7363 | 0.3313 | 0.033* | |
C23 | 0.9211 (3) | 0.86883 (18) | 0.36902 (18) | 0.0342 (6) | |
H23 | 0.9447 | 0.8970 | 0.3266 | 0.041* | |
C24 | 0.8972 (2) | 0.92242 (19) | 0.42767 (18) | 0.0361 (6) | |
H24 | 0.9041 | 0.9875 | 0.4251 | 0.043* | |
C25 | 0.8633 (3) | 0.88367 (18) | 0.49029 (18) | 0.0357 (6) | |
H25 | 0.8487 | 0.9216 | 0.5311 | 0.043* | |
C26 | 0.8508 (2) | 0.78858 (17) | 0.49321 (16) | 0.0293 (5) | |
H26 | 0.8259 | 0.7609 | 0.5353 | 0.035* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.03720 (19) | 0.0647 (2) | 0.02948 (17) | −0.00338 (13) | 0.00838 (13) | −0.00174 (13) |
Br2 | 0.02653 (18) | 0.0681 (2) | 0.0454 (2) | −0.00696 (13) | −0.00249 (14) | 0.01995 (15) |
S1 | 0.0311 (4) | 0.0229 (3) | 0.0279 (3) | −0.0025 (2) | 0.0140 (3) | −0.0019 (2) |
S2 | 0.0193 (3) | 0.0242 (3) | 0.0216 (3) | 0.0012 (2) | 0.0055 (2) | 0.0004 (2) |
O1 | 0.0241 (10) | 0.0494 (11) | 0.0308 (10) | 0.0009 (9) | 0.0113 (8) | 0.0018 (9) |
O2 | 0.0462 (13) | 0.0308 (9) | 0.0494 (12) | 0.0089 (8) | 0.0319 (10) | 0.0056 (8) |
O3 | 0.0501 (13) | 0.0357 (10) | 0.0358 (11) | −0.0185 (9) | 0.0128 (10) | −0.0106 (8) |
O4 | 0.0268 (11) | 0.0701 (14) | 0.0298 (11) | 0.0016 (10) | 0.0093 (9) | 0.0052 (10) |
O5 | 0.0219 (9) | 0.0324 (9) | 0.0352 (10) | 0.0031 (7) | 0.0104 (8) | −0.0044 (7) |
O6 | 0.0299 (10) | 0.0302 (9) | 0.0217 (9) | 0.0000 (7) | 0.0056 (7) | 0.0042 (7) |
N1 | 0.0218 (11) | 0.0245 (10) | 0.0322 (12) | 0.0010 (8) | 0.0081 (9) | 0.0064 (8) |
N2 | 0.0228 (11) | 0.0336 (11) | 0.0284 (11) | −0.0026 (9) | 0.0104 (9) | 0.0067 (9) |
N3 | 0.0242 (11) | 0.0283 (10) | 0.0195 (10) | −0.0021 (8) | 0.0052 (8) | 0.0001 (8) |
N4 | 0.0218 (11) | 0.0317 (10) | 0.0212 (10) | −0.0054 (8) | 0.0059 (8) | 0.0017 (8) |
C1 | 0.0270 (14) | 0.0231 (11) | 0.0325 (14) | 0.0018 (10) | 0.0127 (11) | 0.0037 (10) |
C2 | 0.0236 (13) | 0.0340 (13) | 0.0401 (16) | 0.0013 (11) | 0.0130 (12) | 0.0052 (11) |
C3 | 0.0255 (14) | 0.0317 (13) | 0.0358 (15) | 0.0001 (10) | 0.0039 (12) | 0.0040 (11) |
C4 | 0.0318 (15) | 0.0272 (12) | 0.0299 (14) | 0.0015 (10) | 0.0091 (12) | 0.0029 (10) |
C5 | 0.0256 (14) | 0.0329 (13) | 0.0321 (14) | 0.0017 (10) | 0.0126 (11) | 0.0019 (11) |
C6 | 0.0252 (13) | 0.0200 (11) | 0.0325 (14) | 0.0020 (9) | 0.0103 (11) | 0.0052 (9) |
C7 | 0.0262 (14) | 0.0241 (12) | 0.0329 (14) | 0.0009 (10) | 0.0130 (11) | 0.0048 (10) |
C8 | 0.0250 (13) | 0.0270 (11) | 0.0192 (11) | 0.0015 (9) | 0.0084 (10) | 0.0002 (9) |
C9 | 0.0333 (16) | 0.0446 (16) | 0.0264 (14) | −0.0018 (12) | −0.0003 (12) | 0.0030 (11) |
C10 | 0.0424 (19) | 0.0530 (19) | 0.0410 (18) | 0.0149 (15) | −0.0012 (15) | 0.0170 (14) |
C11 | 0.0474 (19) | 0.0297 (13) | 0.0406 (16) | 0.0118 (12) | 0.0189 (14) | 0.0124 (12) |
C12 | 0.0406 (17) | 0.0252 (12) | 0.0421 (17) | −0.0030 (11) | 0.0098 (14) | 0.0033 (11) |
C13 | 0.0269 (14) | 0.0281 (13) | 0.0378 (15) | 0.0020 (10) | 0.0017 (11) | 0.0038 (11) |
C14 | 0.0247 (14) | 0.0323 (13) | 0.0297 (14) | −0.0019 (10) | 0.0070 (11) | 0.0015 (11) |
C15 | 0.0330 (17) | 0.0581 (18) | 0.0292 (15) | −0.0024 (14) | 0.0111 (13) | 0.0021 (13) |
C16 | 0.0381 (17) | 0.0491 (16) | 0.0249 (14) | −0.0079 (13) | 0.0039 (12) | 0.0057 (12) |
C17 | 0.0242 (14) | 0.0329 (13) | 0.0325 (15) | −0.0065 (10) | 0.0007 (11) | 0.0070 (11) |
C18 | 0.0266 (14) | 0.0374 (14) | 0.0309 (14) | −0.0036 (11) | 0.0078 (11) | 0.0056 (11) |
C19 | 0.0264 (13) | 0.0253 (11) | 0.0251 (13) | −0.0024 (10) | 0.0068 (10) | 0.0014 (9) |
C20 | 0.0233 (13) | 0.0307 (13) | 0.0271 (13) | −0.0022 (10) | 0.0085 (10) | 0.0009 (10) |
C21 | 0.0183 (12) | 0.0242 (11) | 0.0240 (12) | −0.0005 (9) | 0.0042 (9) | 0.0011 (9) |
C22 | 0.0254 (13) | 0.0323 (13) | 0.0245 (13) | −0.0007 (10) | 0.0057 (10) | 0.0017 (10) |
C23 | 0.0302 (15) | 0.0352 (14) | 0.0336 (15) | −0.0045 (11) | 0.0039 (12) | 0.0104 (11) |
C24 | 0.0305 (15) | 0.0277 (13) | 0.0452 (17) | −0.0046 (11) | 0.0039 (12) | 0.0013 (12) |
C25 | 0.0351 (16) | 0.0292 (13) | 0.0422 (16) | −0.0022 (11) | 0.0108 (13) | −0.0088 (12) |
C26 | 0.0288 (14) | 0.0309 (13) | 0.0299 (13) | 0.0003 (10) | 0.0111 (11) | 0.0009 (10) |
Geometric parameters (Å, º) top
Br1—C4 | 1.899 (3) | C8—C9 | 1.387 (4) |
Br2—C17 | 1.893 (3) | C9—C10 | 1.385 (4) |
S1—O2 | 1.4225 (19) | C9—H9 | 0.9500 |
S1—O3 | 1.432 (2) | C10—C11 | 1.377 (5) |
S1—N2 | 1.631 (2) | C10—H10 | 0.9500 |
S1—C8 | 1.757 (2) | C11—C12 | 1.369 (4) |
S2—O6 | 1.4281 (17) | C11—H11 | 0.9500 |
S2—O5 | 1.4335 (17) | C12—C13 | 1.388 (3) |
S2—N4 | 1.646 (2) | C12—H12 | 0.9500 |
S2—C21 | 1.760 (2) | C13—H13 | 0.9500 |
O1—C1 | 1.364 (3) | C14—C15 | 1.385 (4) |
O1—H1O | 0.8400 | C14—C19 | 1.406 (3) |
O4—C14 | 1.362 (3) | C15—C16 | 1.383 (4) |
O4—H4O | 0.8400 | C15—H15 | 0.9500 |
N1—C7 | 1.280 (3) | C16—C17 | 1.391 (4) |
N1—N2 | 1.375 (3) | C16—H16 | 0.9500 |
N2—H2N | 0.8800 | C17—C18 | 1.371 (4) |
N3—C20 | 1.279 (3) | C18—C19 | 1.396 (4) |
N3—N4 | 1.391 (3) | C18—H18 | 0.9500 |
N4—H4N | 0.8800 | C19—C20 | 1.449 (4) |
C1—C2 | 1.389 (4) | C20—H20 | 0.9500 |
C1—C6 | 1.410 (3) | C21—C26 | 1.386 (3) |
C2—C3 | 1.372 (4) | C21—C22 | 1.389 (3) |
C2—H2 | 0.9500 | C22—C23 | 1.385 (3) |
C3—C4 | 1.387 (4) | C22—H22 | 0.9500 |
C3—H3 | 0.9500 | C23—C24 | 1.372 (4) |
C4—C5 | 1.381 (4) | C23—H23 | 0.9500 |
C5—C6 | 1.393 (4) | C24—C25 | 1.379 (4) |
C5—H5 | 0.9500 | C24—H24 | 0.9500 |
C6—C7 | 1.461 (4) | C25—C26 | 1.390 (4) |
C7—H7 | 0.9500 | C25—H25 | 0.9500 |
C8—C13 | 1.375 (3) | C26—H26 | 0.9500 |
O2—S1—O3 | 121.49 (12) | C11—C10—H10 | 119.6 |
O2—S1—N2 | 106.47 (12) | C9—C10—H10 | 119.6 |
O3—S1—N2 | 104.62 (11) | C12—C11—C10 | 120.1 (3) |
O2—S1—C8 | 108.00 (11) | C12—C11—H11 | 120.0 |
O3—S1—C8 | 107.77 (12) | C10—C11—H11 | 120.0 |
N2—S1—C8 | 107.79 (11) | C11—C12—C13 | 120.2 (3) |
O6—S2—O5 | 120.92 (11) | C11—C12—H12 | 119.9 |
O6—S2—N4 | 103.47 (11) | C13—C12—H12 | 119.9 |
O5—S2—N4 | 106.74 (11) | C8—C13—C12 | 119.4 (3) |
O6—S2—C21 | 109.34 (11) | C8—C13—H13 | 120.3 |
O5—S2—C21 | 107.24 (11) | C12—C13—H13 | 120.3 |
N4—S2—C21 | 108.58 (11) | O4—C14—C15 | 117.7 (2) |
C1—O1—H1O | 109.5 | O4—C14—C19 | 122.4 (2) |
C14—O4—H4O | 109.5 | C15—C14—C19 | 119.9 (3) |
C7—N1—N2 | 119.4 (2) | C16—C15—C14 | 120.9 (3) |
N1—N2—S1 | 116.65 (16) | C16—C15—H15 | 119.6 |
N1—N2—H2N | 121.7 | C14—C15—H15 | 119.6 |
S1—N2—H2N | 121.7 | C15—C16—C17 | 119.1 (3) |
C20—N3—N4 | 116.2 (2) | C15—C16—H16 | 120.5 |
N3—N4—S2 | 116.50 (15) | C17—C16—H16 | 120.5 |
N3—N4—H4N | 121.7 | C18—C17—C16 | 120.8 (3) |
S2—N4—H4N | 121.7 | C18—C17—Br2 | 120.3 (2) |
O1—C1—C2 | 118.2 (2) | C16—C17—Br2 | 118.9 (2) |
O1—C1—C6 | 122.1 (2) | C17—C18—C19 | 120.6 (2) |
C2—C1—C6 | 119.7 (2) | C17—C18—H18 | 119.7 |
C3—C2—C1 | 121.2 (3) | C19—C18—H18 | 119.7 |
C3—C2—H2 | 119.4 | C18—C19—C14 | 118.7 (2) |
C1—C2—H2 | 119.4 | C18—C19—C20 | 118.4 (2) |
C2—C3—C4 | 119.1 (3) | C14—C19—C20 | 122.9 (2) |
C2—C3—H3 | 120.4 | N3—C20—C19 | 121.8 (2) |
C4—C3—H3 | 120.4 | N3—C20—H20 | 119.1 |
C5—C4—C3 | 121.0 (3) | C19—C20—H20 | 119.1 |
C5—C4—Br1 | 120.7 (2) | C26—C21—C22 | 121.4 (2) |
C3—C4—Br1 | 118.3 (2) | C26—C21—S2 | 120.25 (18) |
C4—C5—C6 | 120.3 (2) | C22—C21—S2 | 118.37 (18) |
C4—C5—H5 | 119.9 | C23—C22—C21 | 118.6 (2) |
C6—C5—H5 | 119.9 | C23—C22—H22 | 120.7 |
C5—C6—C1 | 118.7 (2) | C21—C22—H22 | 120.7 |
C5—C6—C7 | 119.4 (2) | C24—C23—C22 | 120.2 (2) |
C1—C6—C7 | 121.9 (2) | C24—C23—H23 | 119.9 |
N1—C7—C6 | 119.4 (2) | C22—C23—H23 | 119.9 |
N1—C7—H7 | 120.3 | C23—C24—C25 | 121.3 (3) |
C6—C7—H7 | 120.3 | C23—C24—H24 | 119.4 |
C13—C8—C9 | 121.1 (2) | C25—C24—H24 | 119.4 |
C13—C8—S1 | 119.30 (19) | C24—C25—C26 | 119.4 (2) |
C9—C8—S1 | 119.6 (2) | C24—C25—H25 | 120.3 |
C10—C9—C8 | 118.4 (3) | C26—C25—H25 | 120.3 |
C10—C9—H9 | 120.8 | C21—C26—C25 | 119.1 (2) |
C8—C9—H9 | 120.8 | C21—C26—H26 | 120.5 |
C11—C10—C9 | 120.9 (3) | C25—C26—H26 | 120.5 |
C7—N1—N2—S1 | 166.54 (18) | C10—C11—C12—C13 | 0.5 (5) |
O2—S1—N2—N1 | 36.3 (2) | C9—C8—C13—C12 | 1.0 (4) |
O3—S1—N2—N1 | 166.13 (17) | S1—C8—C13—C12 | −179.8 (2) |
C8—S1—N2—N1 | −79.35 (19) | C11—C12—C13—C8 | −1.2 (4) |
C20—N3—N4—S2 | −162.14 (17) | O4—C14—C15—C16 | −177.1 (3) |
O6—S2—N4—N3 | −175.90 (16) | C19—C14—C15—C16 | 2.6 (4) |
O5—S2—N4—N3 | −47.31 (19) | C14—C15—C16—C17 | −0.5 (4) |
C21—S2—N4—N3 | 68.01 (19) | C15—C16—C17—C18 | −2.1 (4) |
O1—C1—C2—C3 | 179.3 (2) | C15—C16—C17—Br2 | 178.1 (2) |
C6—C1—C2—C3 | −1.0 (4) | C16—C17—C18—C19 | 2.5 (4) |
C1—C2—C3—C4 | 0.4 (4) | Br2—C17—C18—C19 | −177.74 (18) |
C2—C3—C4—C5 | 0.6 (4) | C17—C18—C19—C14 | −0.3 (4) |
C2—C3—C4—Br1 | 179.67 (19) | C17—C18—C19—C20 | 179.4 (2) |
C3—C4—C5—C6 | −0.9 (4) | O4—C14—C19—C18 | 177.5 (2) |
Br1—C4—C5—C6 | −179.97 (17) | C15—C14—C19—C18 | −2.2 (4) |
C4—C5—C6—C1 | 0.3 (4) | O4—C14—C19—C20 | −2.3 (4) |
C4—C5—C6—C7 | 178.3 (2) | C15—C14—C19—C20 | 178.1 (2) |
O1—C1—C6—C5 | −179.6 (2) | N4—N3—C20—C19 | −177.4 (2) |
C2—C1—C6—C5 | 0.7 (3) | C18—C19—C20—N3 | −175.1 (2) |
O1—C1—C6—C7 | 2.4 (4) | C14—C19—C20—N3 | 4.6 (4) |
C2—C1—C6—C7 | −177.3 (2) | O6—S2—C21—C26 | −20.1 (2) |
N2—N1—C7—C6 | 175.8 (2) | O5—S2—C21—C26 | −152.9 (2) |
C5—C6—C7—N1 | 179.2 (2) | N4—S2—C21—C26 | 92.1 (2) |
C1—C6—C7—N1 | −2.9 (3) | O6—S2—C21—C22 | 160.42 (19) |
O2—S1—C8—C13 | −47.0 (2) | O5—S2—C21—C22 | 27.7 (2) |
O3—S1—C8—C13 | −179.9 (2) | N4—S2—C21—C22 | −87.3 (2) |
N2—S1—C8—C13 | 67.7 (2) | C26—C21—C22—C23 | −0.4 (4) |
O2—S1—C8—C9 | 132.2 (2) | S2—C21—C22—C23 | 179.0 (2) |
O3—S1—C8—C9 | −0.7 (2) | C21—C22—C23—C24 | 0.5 (4) |
N2—S1—C8—C9 | −113.1 (2) | C22—C23—C24—C25 | 0.4 (4) |
C13—C8—C9—C10 | −0.3 (4) | C23—C24—C25—C26 | −1.3 (4) |
S1—C8—C9—C10 | −179.5 (2) | C22—C21—C26—C25 | −0.5 (4) |
C8—C9—C10—C11 | −0.3 (5) | S2—C21—C26—C25 | −179.9 (2) |
C9—C10—C11—C12 | 0.2 (5) | C24—C25—C26—C21 | 1.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···N1 | 0.84 | 1.86 | 2.592 (3) | 146 |
O4—H4o···N3 | 0.84 | 1.95 | 2.676 (3) | 144 |
N2—H2n···O5i | 0.88 | 2.17 | 2.963 (3) | 149 |
N4—H4n···O1 | 0.88 | 2.30 | 3.015 (3) | 139 |
Symmetry code: (i) x−1, y, z. |