Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520618013185/aw5014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013185/aw5014Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520618013185/aw5014sup3.pdf |
CCDC reference: 1850982
Cell refinement: SAINT v8.34A (Bruker, 2013); data reduction: SAINT v8.34A (Bruker, 2013); program(s) used to solve structure: XT (Sheldrick, 2015); program(s) used to refine structure: XL (Sheldrick, 2008); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).
C12H10ClN2O5S·C12H12N7 | Z = 2 |
Mr = 584.01 | F(000) = 604 |
Triclinic, P1 | Dx = 1.592 Mg m−3 |
a = 7.522 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.110 (5) Å | Cell parameters from 1237 reflections |
c = 20.892 (14) Å | θ = 2.8–23.4° |
α = 92.574 (16)° | µ = 0.30 mm−1 |
β = 98.836 (17)° | T = 220 K |
γ = 103.844 (16)° | Plate, clear light yellow |
V = 1218.2 (14) Å3 | 0.2 × 0.1 × 0.05 mm |
Bruker APEX-II CCD diffractometer | 3062 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.059 |
Absorption correction: multi-scan SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0630 before and 0.0500 after correction. The Ratio of minimum to maximum transmission is 0.8893. The λ/2 correction factor is 0.00150. | θmax = 27.5°, θmin = 2.0° |
Tmin = 0.663, Tmax = 0.746 | h = −9→9 |
11115 measured reflections | k = −10→10 |
5465 independent reflections | l = −26→26 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.193 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
5465 reflections | Δρmax = 0.47 e Å−3 |
367 parameters | Δρmin = −0.52 e Å−3 |
18 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | −0.04809 (13) | −0.19447 (11) | 0.23218 (5) | 0.0270 (3) | |
Cl1 | −0.03699 (17) | −0.12973 (13) | 0.08124 (5) | 0.0426 (3) | |
O3 | 0.2495 (4) | 0.4148 (3) | 0.34541 (12) | 0.0283 (6) | |
O1 | 0.3799 (4) | 0.5831 (3) | 0.27590 (13) | 0.0304 (6) | |
O4 | −0.0120 (4) | −0.1770 (3) | 0.30147 (13) | 0.0345 (7) | |
O5 | −0.2343 (4) | −0.2578 (3) | 0.19956 (15) | 0.0387 (7) | |
N1 | 0.4676 (4) | 0.6688 (4) | 0.44060 (15) | 0.0256 (7) | |
H1 | 0.3870 | 0.5965 | 0.4119 | 0.031* | |
N5 | 0.5253 (4) | 0.8569 (4) | 0.60343 (15) | 0.0237 (7) | |
N6 | 0.2575 (4) | 0.6314 (4) | 0.51236 (15) | 0.0243 (7) | |
N2 | 0.6727 (4) | 0.7027 (4) | 0.36951 (15) | 0.0308 (8) | |
H2A | 0.7800 | 0.7479 | 0.3588 | 0.037* | |
H2B | 0.5884 | 0.6300 | 0.3421 | 0.037* | |
N3 | 0.7686 (4) | 0.8551 (4) | 0.46776 (15) | 0.0271 (7) | |
N7 | 0.0527 (4) | 0.6111 (4) | 0.58343 (17) | 0.0342 (8) | |
H7A | −0.0318 | 0.5464 | 0.5536 | 0.041* | |
H7B | 0.0254 | 0.6353 | 0.6212 | 0.041* | |
O2 | 0.2262 (5) | 0.5043 (5) | 0.00237 (16) | 0.0560 (9) | |
N8 | 0.3545 (5) | 0.4663 (4) | 0.15552 (16) | 0.0306 (8) | |
H8 | 0.3727 | 0.5583 | 0.1812 | 0.037* | |
N4 | 0.8582 (4) | 1.0072 (4) | 0.56636 (16) | 0.0347 (8) | |
H4A | 0.9652 | 1.0524 | 0.5555 | 0.042* | |
H4B | 0.8354 | 1.0355 | 0.6044 | 0.042* | |
N9 | 0.0673 (5) | −0.3235 (4) | 0.2108 (2) | 0.0331 (8) | |
H9A | 0.067 (6) | −0.330 (5) | 0.166 (2) | 0.040* | |
H9B | 0.158 (6) | −0.337 (6) | 0.234 (2) | 0.040* | |
C9 | 0.4239 (5) | 0.7071 (4) | 0.49943 (18) | 0.0221 (8) | |
C13 | 0.2168 (5) | 0.3006 (4) | 0.23675 (18) | 0.0207 (8) | |
C16 | 0.2844 (5) | 0.4406 (4) | 0.28978 (18) | 0.0221 (8) | |
C1 | 0.3518 (5) | 0.8092 (5) | 0.68864 (18) | 0.0235 (8) | |
C18 | 0.1225 (5) | 0.1436 (4) | 0.25235 (18) | 0.0225 (8) | |
H18 | 0.1078 | 0.1300 | 0.2958 | 0.027* | |
C10 | 0.5547 (5) | 0.8223 (4) | 0.54300 (17) | 0.0222 (8) | |
C11 | 0.7309 (5) | 0.8963 (5) | 0.52540 (18) | 0.0254 (8) | |
C20 | 0.0483 (5) | 0.0049 (4) | 0.20667 (18) | 0.0237 (8) | |
C17 | 0.2466 (5) | 0.3200 (4) | 0.17205 (18) | 0.0233 (8) | |
C6 | 0.4470 (5) | 0.9648 (5) | 0.72208 (19) | 0.0254 (8) | |
H6 | 0.5040 | 1.0539 | 0.6991 | 0.031* | |
C14 | 0.1601 (5) | 0.1834 (5) | 0.12496 (19) | 0.0279 (9) | |
H14 | 0.1693 | 0.1966 | 0.0810 | 0.033* | |
C5 | 0.4591 (5) | 0.9904 (5) | 0.78730 (19) | 0.0284 (9) | |
H5 | 0.5267 | 1.0956 | 0.8093 | 0.034* | |
C12 | 0.6381 (5) | 0.7442 (5) | 0.42689 (18) | 0.0245 (8) | |
C8 | 0.2235 (5) | 0.6729 (5) | 0.57135 (18) | 0.0243 (8) | |
C7 | 0.3661 (5) | 0.7812 (4) | 0.61950 (17) | 0.0214 (8) | |
C21 | 0.0625 (5) | 0.0310 (5) | 0.14233 (19) | 0.0264 (8) | |
C2 | 0.2652 (5) | 0.6801 (5) | 0.72306 (19) | 0.0279 (9) | |
H2 | 0.1993 | 0.5741 | 0.7012 | 0.034* | |
C4 | 0.3717 (5) | 0.8614 (5) | 0.8215 (2) | 0.0313 (9) | |
H4 | 0.3779 | 0.8795 | 0.8666 | 0.038* | |
C3 | 0.2760 (5) | 0.7072 (5) | 0.7892 (2) | 0.0322 (9) | |
H3 | 0.2173 | 0.6195 | 0.8125 | 0.039* | |
C19 | 0.3682 (6) | 0.5853 (5) | 0.05015 (19) | 0.0307 (9) | |
C15 | 0.4424 (6) | 0.4799 (5) | 0.09744 (19) | 0.0311 (9) | |
H15A | 0.4248 | 0.3653 | 0.0764 | 0.037* | |
H15B | 0.5762 | 0.5286 | 0.1106 | 0.037* | |
C24 | 0.4107 (8) | 0.7501 (6) | 0.0430 (3) | 0.0567 (14) | |
H24 | 0.5064 | 0.8340 | 0.0687 | 0.068* | |
C22 | 0.1797 (8) | 0.6319 (9) | −0.0334 (3) | 0.0685 (16) | |
H22 | 0.0835 | 0.6134 | −0.0694 | 0.082* | |
C23 | 0.2832 (9) | 0.7764 (8) | −0.0114 (3) | 0.0694 (16) | |
H23 | 0.2773 | 0.8815 | −0.0277 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0227 (5) | 0.0214 (5) | 0.0346 (6) | 0.0002 (4) | 0.0076 (4) | −0.0005 (4) |
Cl1 | 0.0565 (7) | 0.0351 (6) | 0.0291 (6) | 0.0049 (5) | −0.0009 (5) | −0.0095 (4) |
O3 | 0.0297 (15) | 0.0285 (14) | 0.0241 (15) | −0.0003 (11) | 0.0104 (12) | −0.0024 (11) |
O1 | 0.0309 (15) | 0.0245 (14) | 0.0298 (16) | −0.0029 (11) | 0.0022 (12) | 0.0013 (11) |
O4 | 0.0380 (16) | 0.0304 (15) | 0.0311 (16) | −0.0051 (12) | 0.0146 (13) | 0.0036 (12) |
O5 | 0.0176 (14) | 0.0318 (15) | 0.059 (2) | −0.0027 (11) | 0.0015 (14) | −0.0091 (14) |
N1 | 0.0176 (16) | 0.0298 (17) | 0.0236 (18) | −0.0059 (12) | 0.0051 (13) | −0.0017 (14) |
N5 | 0.0189 (16) | 0.0268 (16) | 0.0230 (17) | 0.0001 (12) | 0.0052 (13) | −0.0004 (13) |
N6 | 0.0178 (16) | 0.0286 (17) | 0.0241 (17) | −0.0016 (12) | 0.0088 (13) | 0.0002 (13) |
N2 | 0.0195 (16) | 0.0392 (19) | 0.0267 (19) | −0.0090 (14) | 0.0111 (14) | −0.0079 (15) |
N3 | 0.0222 (16) | 0.0319 (18) | 0.0216 (17) | −0.0036 (13) | 0.0038 (14) | −0.0024 (14) |
N7 | 0.0198 (17) | 0.047 (2) | 0.0288 (19) | −0.0072 (14) | 0.0087 (14) | −0.0056 (16) |
O2 | 0.048 (2) | 0.071 (2) | 0.042 (2) | 0.0081 (18) | −0.0029 (17) | 0.0050 (18) |
N8 | 0.041 (2) | 0.0237 (16) | 0.0292 (19) | 0.0044 (14) | 0.0188 (16) | 0.0031 (14) |
N4 | 0.0265 (18) | 0.045 (2) | 0.0237 (18) | −0.0094 (15) | 0.0090 (15) | −0.0068 (15) |
N9 | 0.031 (2) | 0.0272 (18) | 0.043 (2) | 0.0119 (15) | 0.0038 (18) | 0.0044 (17) |
C9 | 0.0169 (18) | 0.0261 (19) | 0.022 (2) | 0.0010 (14) | 0.0051 (15) | 0.0016 (15) |
C13 | 0.0158 (17) | 0.0220 (18) | 0.025 (2) | 0.0049 (14) | 0.0042 (15) | 0.0001 (15) |
C16 | 0.0173 (18) | 0.0210 (18) | 0.026 (2) | 0.0030 (14) | 0.0021 (16) | 0.0024 (15) |
C1 | 0.0182 (18) | 0.0263 (19) | 0.025 (2) | 0.0029 (14) | 0.0057 (16) | 0.0026 (16) |
C18 | 0.0195 (18) | 0.0231 (18) | 0.024 (2) | 0.0028 (14) | 0.0050 (16) | 0.0011 (15) |
C10 | 0.0220 (19) | 0.0217 (18) | 0.020 (2) | −0.0005 (14) | 0.0052 (15) | 0.0005 (15) |
C11 | 0.0215 (19) | 0.0268 (19) | 0.024 (2) | −0.0023 (15) | 0.0048 (16) | 0.0032 (16) |
C20 | 0.0202 (18) | 0.0242 (19) | 0.027 (2) | 0.0041 (14) | 0.0073 (16) | −0.0011 (15) |
C17 | 0.027 (2) | 0.0228 (19) | 0.022 (2) | 0.0094 (15) | 0.0047 (16) | 0.0055 (15) |
C6 | 0.024 (2) | 0.0252 (19) | 0.027 (2) | 0.0039 (15) | 0.0097 (17) | 0.0022 (16) |
C14 | 0.033 (2) | 0.029 (2) | 0.023 (2) | 0.0106 (17) | 0.0044 (17) | 0.0050 (16) |
C5 | 0.030 (2) | 0.0241 (19) | 0.029 (2) | 0.0029 (16) | 0.0065 (18) | −0.0041 (16) |
C12 | 0.0217 (19) | 0.0254 (19) | 0.023 (2) | −0.0009 (15) | 0.0047 (16) | 0.0030 (16) |
C8 | 0.0180 (18) | 0.030 (2) | 0.025 (2) | 0.0032 (15) | 0.0084 (16) | 0.0048 (16) |
C7 | 0.0192 (18) | 0.0235 (18) | 0.0194 (19) | 0.0008 (14) | 0.0042 (15) | 0.0019 (15) |
C21 | 0.027 (2) | 0.027 (2) | 0.023 (2) | 0.0048 (15) | 0.0031 (17) | −0.0040 (16) |
C2 | 0.027 (2) | 0.029 (2) | 0.027 (2) | 0.0037 (16) | 0.0094 (17) | 0.0008 (16) |
C4 | 0.032 (2) | 0.040 (2) | 0.023 (2) | 0.0090 (18) | 0.0072 (18) | 0.0021 (18) |
C3 | 0.031 (2) | 0.031 (2) | 0.033 (2) | 0.0021 (17) | 0.0093 (18) | 0.0104 (18) |
C19 | 0.035 (2) | 0.035 (2) | 0.023 (2) | 0.0068 (18) | 0.0095 (18) | 0.0025 (17) |
C15 | 0.033 (2) | 0.038 (2) | 0.024 (2) | 0.0077 (18) | 0.0108 (18) | 0.0106 (18) |
C24 | 0.080 (3) | 0.040 (2) | 0.049 (3) | 0.010 (2) | 0.014 (2) | 0.010 (2) |
C22 | 0.060 (3) | 0.102 (4) | 0.054 (3) | 0.040 (3) | 0.005 (2) | 0.024 (3) |
C23 | 0.097 (4) | 0.072 (3) | 0.059 (3) | 0.046 (3) | 0.028 (3) | 0.031 (3) |
S1—O4 | 1.425 (3) | C13—C16 | 1.488 (5) |
S1—O5 | 1.422 (3) | C13—C18 | 1.381 (5) |
S1—N9 | 1.600 (4) | C13—C17 | 1.413 (5) |
S1—C20 | 1.749 (4) | C1—C6 | 1.388 (5) |
Cl1—C21 | 1.726 (4) | C1—C7 | 1.476 (5) |
O3—C16 | 1.246 (4) | C1—C2 | 1.387 (5) |
O1—C16 | 1.278 (4) | C18—H18 | 0.9400 |
N1—H1 | 0.8700 | C18—C20 | 1.388 (5) |
N1—C9 | 1.361 (5) | C10—C11 | 1.428 (5) |
N1—C12 | 1.361 (4) | C20—C21 | 1.386 (5) |
N5—C10 | 1.344 (5) | C17—C14 | 1.407 (5) |
N5—C7 | 1.309 (4) | C6—H6 | 0.9400 |
N6—C9 | 1.329 (4) | C6—C5 | 1.355 (5) |
N6—C8 | 1.341 (5) | C14—H14 | 0.9400 |
N2—H2A | 0.8700 | C14—C21 | 1.373 (5) |
N2—H2B | 0.8700 | C5—H5 | 0.9400 |
N2—C12 | 1.311 (5) | C5—C4 | 1.385 (5) |
N3—C11 | 1.325 (5) | C8—C7 | 1.439 (5) |
N3—C12 | 1.324 (5) | C2—H2 | 0.9400 |
N7—H7A | 0.8700 | C2—C3 | 1.377 (6) |
N7—H7B | 0.8700 | C4—H4 | 0.9400 |
N7—C8 | 1.330 (4) | C4—C3 | 1.371 (6) |
O2—C19 | 1.359 (5) | C3—H3 | 0.9400 |
O2—C22 | 1.383 (6) | C19—C15 | 1.467 (5) |
N8—H8 | 0.8700 | C19—C24 | 1.319 (6) |
N8—C17 | 1.359 (4) | C15—H15A | 0.9800 |
N8—C15 | 1.464 (5) | C15—H15B | 0.9800 |
N4—H4A | 0.8700 | C24—H24 | 0.9400 |
N4—H4B | 0.8700 | C24—C23 | 1.429 (8) |
N4—C11 | 1.313 (5) | C22—H22 | 0.9400 |
N9—H9A | 0.93 (5) | C22—C23 | 1.264 (8) |
N9—H9B | 0.80 (4) | C23—H23 | 0.9400 |
C9—C10 | 1.370 (5) | ||
O4—S1—N9 | 105.9 (2) | N8—C17—C13 | 121.2 (3) |
O4—S1—C20 | 106.70 (17) | N8—C17—C14 | 120.8 (3) |
O5—S1—O4 | 118.97 (18) | C14—C17—C13 | 118.0 (3) |
O5—S1—N9 | 107.02 (19) | C1—C6—H6 | 119.4 |
O5—S1—C20 | 110.05 (18) | C5—C6—C1 | 121.2 (3) |
N9—S1—C20 | 107.70 (18) | C5—C6—H6 | 119.4 |
C9—N1—H1 | 120.2 | C17—C14—H14 | 119.6 |
C9—N1—C12 | 119.7 (3) | C21—C14—C17 | 120.9 (4) |
C12—N1—H1 | 120.2 | C21—C14—H14 | 119.6 |
C7—N5—C10 | 118.5 (3) | C6—C5—H5 | 120.0 |
C9—N6—C8 | 116.2 (3) | C6—C5—C4 | 119.9 (4) |
H2A—N2—H2B | 120.0 | C4—C5—H5 | 120.0 |
C12—N2—H2A | 120.0 | N2—C12—N1 | 117.1 (3) |
C12—N2—H2B | 120.0 | N2—C12—N3 | 118.9 (3) |
C12—N3—C11 | 118.1 (3) | N3—C12—N1 | 124.0 (3) |
H7A—N7—H7B | 120.0 | N6—C8—C7 | 121.2 (3) |
C8—N7—H7A | 120.0 | N7—C8—N6 | 117.4 (3) |
C8—N7—H7B | 120.0 | N7—C8—C7 | 121.4 (3) |
C19—O2—C22 | 105.3 (4) | N5—C7—C1 | 115.5 (3) |
C17—N8—H8 | 117.7 | N5—C7—C8 | 119.7 (3) |
C17—N8—C15 | 124.6 (3) | C8—C7—C1 | 124.8 (3) |
C15—N8—H8 | 117.7 | C20—C21—Cl1 | 121.0 (3) |
H4A—N4—H4B | 120.0 | C14—C21—Cl1 | 117.5 (3) |
C11—N4—H4A | 120.0 | C14—C21—C20 | 121.5 (3) |
C11—N4—H4B | 120.0 | C1—C2—H2 | 120.0 |
S1—N9—H9A | 112 (3) | C3—C2—C1 | 119.9 (4) |
S1—N9—H9B | 122 (3) | C3—C2—H2 | 120.0 |
H9A—N9—H9B | 118 (4) | C5—C4—H4 | 120.1 |
N1—C9—C10 | 118.2 (3) | C3—C4—C5 | 119.8 (4) |
N6—C9—N1 | 119.0 (3) | C3—C4—H4 | 120.1 |
N6—C9—C10 | 122.8 (3) | C2—C3—H3 | 119.8 |
C18—C13—C16 | 117.7 (3) | C4—C3—C2 | 120.5 (4) |
C18—C13—C17 | 118.9 (3) | C4—C3—H3 | 119.8 |
C17—C13—C16 | 123.4 (3) | O2—C19—C15 | 117.3 (4) |
O3—C16—O1 | 122.8 (3) | C24—C19—O2 | 109.5 (4) |
O3—C16—C13 | 119.7 (3) | C24—C19—C15 | 133.2 (4) |
O1—C16—C13 | 117.5 (3) | N8—C15—C19 | 113.3 (3) |
C6—C1—C7 | 118.5 (3) | N8—C15—H15A | 108.9 |
C2—C1—C6 | 118.7 (4) | N8—C15—H15B | 108.9 |
C2—C1—C7 | 122.4 (3) | C19—C15—H15A | 108.9 |
C13—C18—H18 | 118.5 | C19—C15—H15B | 108.9 |
C13—C18—C20 | 122.9 (3) | H15A—C15—H15B | 107.7 |
C20—C18—H18 | 118.5 | C19—C24—H24 | 126.6 |
N5—C10—C9 | 121.2 (3) | C19—C24—C23 | 106.7 (5) |
N5—C10—C11 | 119.5 (3) | C23—C24—H24 | 126.6 |
C9—C10—C11 | 119.1 (3) | O2—C22—H22 | 124.4 |
N3—C11—C10 | 120.9 (3) | C23—C22—O2 | 111.3 (5) |
N4—C11—N3 | 119.0 (3) | C23—C22—H22 | 124.4 |
N4—C11—C10 | 120.2 (3) | C24—C23—H23 | 126.5 |
C18—C20—S1 | 119.6 (3) | C22—C23—C24 | 107.1 (5) |
C21—C20—S1 | 123.0 (3) | C22—C23—H23 | 126.5 |
C21—C20—C18 | 117.3 (3) |