Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615010311/fn3197sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010311/fn3197Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010311/fn3197IIsup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615010311/fn3197Isup4.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615010311/fn3197IIsup5.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229615010311/fn3197sup6.pdf |
CCDC references: 1403757; 1403756
For both compounds, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008) and ORTEP-3 for Windows (Farrugia, 2012). Software used to prepare material for publication: WinGX (Farrugia, 2012) for (I); WinGX (Farrugia, 2012) and PLATON (Spek, 2009) for (II).
2C10H9ClN4S·CH4O·H2O | Z = 2 |
Mr = 555.50 | F(000) = 576 |
Triclinic, P1 | Dx = 1.528 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 7.1462 (2) Å | Cell parameters from 6106 reflections |
b = 13.1927 (5) Å | θ = 3.0–29.6° |
c = 13.6379 (5) Å | µ = 0.48 mm−1 |
α = 94.905 (3)° | T = 298 K |
β = 104.416 (3)° | Prismatic, yellow |
γ = 101.579 (3)° | 0.38 × 0.04 × 0.03 mm |
V = 1207.43 (8) Å3 |
Agilent Xcalibur Gemini Ultra diffractometer with Atlas detector | 5778 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 4091 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 10.4186 pixels mm-1 | θmax = 29.6°, θmin = 3.0° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −18→17 |
Tmin = 0.855, Tmax = 1.000 | l = −18→18 |
12034 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.034 | W = 1/[Σ2(FO2) + (0.0498P)2] where P = (FO2 + 2FC2)/3 |
wR(F2) = 0.089 | (Δ/σ)max = 0.001 |
S = 0.97 | Δρmax = 0.31 e Å−3 |
5778 reflections | Δρmin = −0.30 e Å−3 |
353 parameters |
Experimental. #__ type_ start__ end____ width___ exp.time_ 1 omega 57.00 103.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 12.8811 179.0000 - 150.0000 46 #__ type_ start__ end____ width___ exp.time_ 2 omega -50.00 39.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 12.8811 - 38.0000 0.0000 89 #__ type_ start__ end____ width___ exp.time_ 3 omega -42.00 0.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 12.8811 121.0000 - 88.0000 42 #__ type_ start__ end____ width___ exp.time_ 4 omega -43.00 43.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 12.8811 - 77.0000 - 180.0000 86 #__ type_ start__ end____ width___ exp.time_ 5 omega -63.00 39.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 12.8811 - 38.0000 - 90.0000 102 |
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. Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. Item _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.10461 (7) | 0.34104 (3) | 0.93447 (3) | 0.03228 (11) | |
S1A | 0.33413 (7) | 0.11031 (4) | 0.50264 (3) | 0.03807 (13) | |
Cl1 | 0.22944 (8) | 0.45169 (5) | 0.19129 (3) | 0.05632 (16) | |
Cl1A | 0.92970 (8) | 0.06098 (5) | 1.28161 (3) | 0.05420 (15) | |
NQ | 0.2430 (2) | 0.65246 (11) | 0.52842 (10) | 0.0310 (3) | |
H1Q | 0.2441 | 0.7071 | 0.4982 | 0.037* | |
NQA | 0.6796 (2) | −0.17090 (11) | 0.93755 (10) | 0.0335 (3) | |
H2Q | 0.6896 | −0.2230 | 0.9708 | 0.040* | |
N1 | 0.22697 (19) | 0.38947 (10) | 0.67242 (9) | 0.0263 (3) | |
N1A | 0.6305 (2) | 0.07906 (10) | 0.77966 (9) | 0.0291 (3) | |
N2 | 0.2206 (2) | 0.40149 (11) | 0.77549 (10) | 0.0280 (3) | |
H2N | 0.293 (3) | 0.4520 (15) | 0.8177 (14) | 0.038 (5)* | |
N2A | 0.5422 (2) | 0.06029 (11) | 0.67346 (10) | 0.0293 (3) | |
HN2A | 0.554 (3) | 0.0128 (15) | 0.6385 (13) | 0.034 (5)* | |
N4 | −0.0080 (2) | 0.24564 (12) | 0.74333 (11) | 0.0351 (3) | |
H4NA | −0.012 (2) | 0.2403 (14) | 0.6748 (14) | 0.032 (4)* | |
H4NB | −0.089 (3) | 0.1977 (17) | 0.7648 (16) | 0.054 (6)* | |
N4A | 0.4436 (3) | 0.21142 (13) | 0.69268 (12) | 0.0397 (4) | |
H4NC | 0.497 (3) | 0.2146 (15) | 0.7568 (16) | 0.043 (5)* | |
H4ND | 0.383 (3) | 0.2549 (18) | 0.6700 (16) | 0.057 (7)* | |
O1 | 0.1142 (3) | 0.84669 (12) | 0.47815 (11) | 0.0472 (4) | |
H1A | 0.192 (4) | 0.909 (3) | 0.485 (2) | 0.102 (11)* | |
H1B | 0.008 (4) | 0.8553 (19) | 0.4845 (18) | 0.066 (8)* | |
O2 | 0.4410 (2) | 0.58402 (11) | 0.92904 (10) | 0.0421 (3) | |
H2O | 0.555 (4) | 0.583 (2) | 0.9660 (19) | 0.076 (8)* | |
C2 | 0.2371 (2) | 0.65886 (13) | 0.62650 (12) | 0.0311 (4) | |
H2 | 0.2307 | 0.7224 | 0.6591 | 0.037* | |
C2A | 0.6117 (3) | −0.18817 (13) | 0.83499 (12) | 0.0336 (4) | |
H2A | 0.5791 | −0.2565 | 0.8019 | 0.040* | |
C3 | 0.1068 (2) | 0.32828 (12) | 0.80947 (11) | 0.0241 (3) | |
C3A | 0.4475 (2) | 0.12911 (13) | 0.63094 (11) | 0.0277 (3) | |
C3B | 0.2399 (2) | 0.57738 (13) | 0.67963 (12) | 0.0285 (4) | |
H3 | 0.2418 | 0.5870 | 0.7483 | 0.034* | |
C3D | 0.5890 (2) | −0.11091 (13) | 0.77818 (12) | 0.0309 (4) | |
H3A | 0.5370 | −0.1272 | 0.7076 | 0.037* | |
C4 | 0.2398 (2) | 0.47610 (12) | 0.63220 (11) | 0.0228 (3) | |
C4A | 0.6437 (2) | −0.00374 (12) | 0.82459 (11) | 0.0232 (3) | |
C5 | 0.2505 (2) | 0.37740 (13) | 0.46936 (11) | 0.0289 (4) | |
H5 | 0.2535 | 0.3181 | 0.5015 | 0.035* | |
C5A | 0.7782 (2) | 0.11399 (13) | 0.99288 (12) | 0.0315 (4) | |
H5A | 0.7727 | 0.1717 | 0.9585 | 0.038* | |
C6 | 0.2480 (2) | 0.37101 (14) | 0.36745 (12) | 0.0326 (4) | |
H6 | 0.2484 | 0.3083 | 0.3308 | 0.039* | |
C6A | 0.8430 (3) | 0.12866 (14) | 1.09808 (12) | 0.0362 (4) | |
H6A | 0.8809 | 0.1957 | 1.1346 | 0.043* | |
C7 | 0.2448 (2) | 0.46072 (15) | 0.32086 (12) | 0.0334 (4) | |
C7A | 0.8510 (2) | 0.04256 (15) | 1.14878 (12) | 0.0334 (4) | |
C8 | 0.2462 (2) | 0.55421 (14) | 0.37251 (12) | 0.0312 (4) | |
H8 | 0.2463 | 0.6133 | 0.3399 | 0.037* | |
C8A | 0.7984 (2) | −0.05678 (14) | 1.09764 (12) | 0.0325 (4) | |
H8A | 0.8055 | −0.1137 | 1.1330 | 0.039* | |
C9 | 0.2473 (2) | 0.55939 (13) | 0.47591 (11) | 0.0257 (3) | |
C9A | 0.7334 (2) | −0.07104 (13) | 0.99022 (11) | 0.0256 (3) | |
C10 | 0.2485 (2) | 0.47090 (12) | 0.52545 (11) | 0.0228 (3) | |
C10A | 0.7205 (2) | 0.01376 (12) | 0.93684 (11) | 0.0235 (3) | |
C11 | 0.3299 (3) | 0.62297 (16) | 0.98945 (16) | 0.0495 (5) | |
H11A | 0.2181 | 0.6419 | 0.9460 | 0.074* | |
H11B | 0.4121 | 0.6834 | 1.0358 | 0.074* | |
H11C | 0.2839 | 0.5701 | 1.0277 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0422 (3) | 0.0336 (2) | 0.0237 (2) | 0.0070 (2) | 0.01350 (18) | 0.00931 (17) |
S1A | 0.0536 (3) | 0.0383 (3) | 0.0235 (2) | 0.0225 (2) | 0.00280 (19) | 0.00596 (18) |
Cl1 | 0.0739 (4) | 0.0830 (4) | 0.0250 (2) | 0.0318 (3) | 0.0222 (2) | 0.0185 (2) |
Cl1A | 0.0616 (3) | 0.0741 (4) | 0.0207 (2) | 0.0099 (3) | 0.0053 (2) | 0.0045 (2) |
NQ | 0.0382 (8) | 0.0218 (7) | 0.0323 (7) | 0.0047 (6) | 0.0076 (6) | 0.0121 (6) |
NQA | 0.0477 (9) | 0.0225 (7) | 0.0298 (7) | 0.0093 (7) | 0.0061 (6) | 0.0110 (6) |
N1 | 0.0358 (7) | 0.0262 (7) | 0.0183 (6) | 0.0065 (6) | 0.0096 (5) | 0.0066 (5) |
N1A | 0.0404 (8) | 0.0249 (7) | 0.0208 (6) | 0.0094 (6) | 0.0039 (6) | 0.0060 (5) |
N2 | 0.0370 (8) | 0.0253 (7) | 0.0196 (6) | 0.0013 (7) | 0.0084 (6) | 0.0043 (6) |
N2A | 0.0424 (8) | 0.0255 (8) | 0.0203 (6) | 0.0130 (7) | 0.0048 (6) | 0.0035 (6) |
N4 | 0.0425 (9) | 0.0327 (9) | 0.0253 (7) | −0.0017 (7) | 0.0085 (7) | 0.0051 (7) |
N4A | 0.0571 (11) | 0.0371 (9) | 0.0272 (8) | 0.0252 (9) | 0.0044 (7) | 0.0035 (7) |
O1 | 0.0583 (10) | 0.0368 (9) | 0.0476 (8) | 0.0118 (8) | 0.0160 (7) | 0.0052 (6) |
O2 | 0.0424 (8) | 0.0463 (8) | 0.0358 (7) | 0.0088 (7) | 0.0108 (6) | −0.0015 (6) |
C2 | 0.0321 (9) | 0.0242 (8) | 0.0328 (8) | 0.0055 (7) | 0.0030 (7) | 0.0007 (7) |
C2A | 0.0452 (10) | 0.0209 (8) | 0.0318 (8) | 0.0050 (8) | 0.0076 (8) | 0.0025 (7) |
C3 | 0.0281 (8) | 0.0235 (8) | 0.0228 (7) | 0.0096 (7) | 0.0065 (6) | 0.0074 (6) |
C3A | 0.0315 (9) | 0.0264 (8) | 0.0272 (8) | 0.0076 (7) | 0.0094 (7) | 0.0081 (7) |
C3B | 0.0326 (9) | 0.0281 (9) | 0.0235 (7) | 0.0059 (7) | 0.0064 (7) | 0.0030 (7) |
C3D | 0.0404 (10) | 0.0253 (9) | 0.0240 (8) | 0.0053 (8) | 0.0052 (7) | 0.0031 (7) |
C4 | 0.0192 (7) | 0.0253 (8) | 0.0232 (7) | 0.0033 (6) | 0.0045 (6) | 0.0070 (6) |
C4A | 0.0228 (8) | 0.0245 (8) | 0.0229 (7) | 0.0058 (7) | 0.0063 (6) | 0.0048 (6) |
C5 | 0.0336 (9) | 0.0301 (9) | 0.0267 (8) | 0.0115 (7) | 0.0100 (7) | 0.0088 (7) |
C5A | 0.0397 (9) | 0.0257 (9) | 0.0286 (8) | 0.0064 (8) | 0.0086 (7) | 0.0051 (7) |
C6 | 0.0368 (9) | 0.0392 (10) | 0.0255 (8) | 0.0134 (8) | 0.0117 (7) | 0.0052 (7) |
C6A | 0.0436 (10) | 0.0321 (10) | 0.0287 (8) | 0.0048 (8) | 0.0073 (8) | −0.0013 (7) |
C7 | 0.0284 (9) | 0.0522 (12) | 0.0245 (8) | 0.0124 (8) | 0.0117 (7) | 0.0117 (8) |
C7A | 0.0305 (9) | 0.0473 (11) | 0.0217 (7) | 0.0089 (8) | 0.0058 (7) | 0.0048 (7) |
C8 | 0.0287 (9) | 0.0399 (10) | 0.0293 (8) | 0.0084 (8) | 0.0104 (7) | 0.0192 (8) |
C8A | 0.0353 (9) | 0.0391 (10) | 0.0262 (8) | 0.0119 (8) | 0.0079 (7) | 0.0143 (7) |
C9 | 0.0210 (8) | 0.0297 (9) | 0.0273 (8) | 0.0057 (7) | 0.0060 (6) | 0.0100 (7) |
C9A | 0.0264 (8) | 0.0262 (8) | 0.0262 (7) | 0.0070 (7) | 0.0087 (6) | 0.0082 (6) |
C10 | 0.0202 (7) | 0.0271 (8) | 0.0224 (7) | 0.0060 (6) | 0.0063 (6) | 0.0078 (6) |
C10A | 0.0245 (8) | 0.0248 (8) | 0.0228 (7) | 0.0071 (7) | 0.0070 (6) | 0.0064 (6) |
C11 | 0.0613 (13) | 0.0407 (12) | 0.0571 (12) | 0.0197 (11) | 0.0290 (11) | 0.0080 (10) |
S1—C3 | 1.7029 (14) | C2A—C3D | 1.343 (2) |
Cl1—C7 | 1.7350 (16) | C2A—H2A | 0.9300 |
N1—C4 | 1.3060 (19) | C3B—C4 | 1.434 (2) |
N1—N2 | 1.4140 (17) | C3B—H3 | 0.9300 |
N2—C3 | 1.326 (2) | C3D—C4A | 1.433 (2) |
N4—C3 | 1.334 (2) | C3D—H3A | 0.9300 |
S1A—C3A | 1.7084 (16) | C4—C10 | 1.469 (2) |
Cl1A—C7A | 1.7376 (16) | C4A—C10A | 1.473 (2) |
N1A—C4A | 1.3057 (19) | C5—C6 | 1.381 (2) |
N1A—N2A | 1.4065 (18) | C5—C10 | 1.399 (2) |
N2A—C3A | 1.3266 (19) | C5—H5 | 0.9300 |
N4A—C3A | 1.325 (2) | C5A—C6A | 1.377 (2) |
NQ—C2 | 1.345 (2) | C5A—C10A | 1.398 (2) |
NQ—C9 | 1.377 (2) | C5A—H5A | 0.9300 |
NQ—H1Q | 0.8600 | C6—C7 | 1.392 (2) |
NQA—C2A | 1.344 (2) | C6—H6 | 0.9300 |
NQA—C9A | 1.377 (2) | C6A—C7A | 1.383 (2) |
NQA—H2Q | 0.8600 | C6A—H6A | 0.9300 |
N2—H2N | 0.83 (2) | C7—C8 | 1.364 (2) |
N2A—HN2A | 0.787 (18) | C7A—C8A | 1.364 (2) |
N4—H4NA | 0.924 (18) | C8—C9 | 1.404 (2) |
N4—H4NB | 0.89 (2) | C8—H8 | 0.9300 |
N4A—H4NC | 0.86 (2) | C8A—C9A | 1.406 (2) |
N4A—H4ND | 0.82 (2) | C8A—H8A | 0.9300 |
O1—H1A | 0.88 (3) | C9—C10 | 1.398 (2) |
O1—H1B | 0.81 (3) | C9A—C10A | 1.392 (2) |
O2—C11 | 1.411 (2) | C11—H11A | 0.9600 |
O2—H2O | 0.85 (3) | C11—H11B | 0.9600 |
C2—C3B | 1.347 (2) | C11—H11C | 0.9600 |
C2—H2 | 0.9300 | ||
Cl1···S1i | 3.4988 (6) | O1···N4vi | 3.007 (2) |
Cl1···O2ii | 3.2709 (16) | O1···NQ | 2.969 (2) |
Cl1A···S1Aiii | 3.5262 (7) | O2···O2v | 3.169 (2) |
S1···NQAiv | 3.3440 (15) | O2···N2 | 2.939 (2) |
S1···O2v | 3.2207 (15) | N1···N4 | 2.683 (2) |
S1A···O1vi | 3.432 (2) | N1···N4A | 3.058 (2) |
S1A···O1vii | 3.4675 (17) | N1A···N4A | 2.597 (2) |
S1A···N2Aviii | 3.5420 (15) | N1A···N4ix | 3.208 (2) |
C2—NQ—C9 | 120.71 (14) | N1—C4—C3B | 127.21 (13) |
C2—NQ—H1Q | 119.6 | N1—C4—C10 | 117.77 (13) |
C9—NQ—H1Q | 119.6 | C3B—C4—C10 | 114.99 (14) |
C2A—NQA—C9A | 120.99 (14) | N1A—C4A—C3D | 127.94 (14) |
C2A—NQA—H2Q | 119.5 | N1A—C4A—C10A | 116.72 (13) |
C9A—NQA—H2Q | 119.5 | C3D—C4A—C10A | 115.33 (14) |
C4—N1—N2 | 114.12 (12) | C6—C5—C10 | 121.59 (15) |
C4A—N1A—N2A | 115.90 (12) | C6—C5—H5 | 119.2 |
C3—N2—N1 | 120.51 (13) | C10—C5—H5 | 119.2 |
N2—C3—S1 | 120.49 (12) | C6A—C5A—C10A | 121.09 (16) |
N4—C3—S1 | 120.94 (13) | C6A—C5A—H5A | 119.5 |
C6—C7—Cl1 | 118.57 (13) | C10A—C5A—H5A | 119.5 |
C8—C7—Cl1 | 119.02 (13) | C5—C6—C7 | 118.37 (15) |
C3A—N2A—N1A | 118.44 (13) | C5—C6—H6 | 120.8 |
N2A—C3A—S1A | 120.89 (11) | C7—C6—H6 | 120.8 |
N4A—C3A—S1A | 122.21 (12) | C5A—C6A—C7A | 119.23 (16) |
C6A—C7A—Cl1A | 119.22 (13) | C5A—C6A—H6A | 120.4 |
C8A—C7A—Cl1A | 118.81 (14) | C7A—C6A—H6A | 120.4 |
C3—N2—H2N | 117.7 (13) | C8—C7—C6 | 122.37 (14) |
N1—N2—H2N | 121.7 (13) | C8A—C7A—C6A | 121.96 (15) |
C3A—N2A—HN2A | 119.5 (13) | C7—C8—C9 | 118.64 (15) |
N1A—N2A—HN2A | 121.9 (13) | C7—C8—H8 | 120.7 |
C3—N4—H4NA | 121.0 (12) | C9—C8—H8 | 120.7 |
C3—N4—H4NB | 119.2 (13) | C7A—C8A—C9A | 118.45 (15) |
H4NA—N4—H4NB | 119.6 (18) | C7A—C8A—H8A | 120.8 |
C3A—N4A—H4NC | 117.8 (13) | C9A—C8A—H8A | 120.8 |
C3A—N4A—H4ND | 120.2 (15) | NQ—C9—C10 | 119.73 (13) |
H4NC—N4A—H4ND | 121.8 (19) | NQ—C9—C8 | 119.39 (15) |
H1A—O1—H1B | 107 (2) | C10—C9—C8 | 120.87 (14) |
C11—O2—H2O | 110.2 (16) | NQA—C9A—C10A | 119.82 (13) |
NQ—C2—C3B | 123.00 (15) | NQA—C9A—C8A | 119.09 (14) |
NQ—C2—H2 | 118.5 | C10A—C9A—C8A | 121.08 (14) |
C3B—C2—H2 | 118.5 | C9—C10—C5 | 118.15 (13) |
C3D—C2A—NQA | 122.82 (15) | C9—C10—C4 | 120.32 (13) |
C3D—C2A—H2A | 118.6 | C5—C10—C4 | 121.49 (14) |
NQA—C2A—H2A | 118.6 | C9A—C10A—C5A | 118.17 (13) |
N2—C3—N4 | 118.56 (14) | C9A—C10A—C4A | 119.94 (13) |
N4A—C3A—N2A | 116.90 (14) | C5A—C10A—C4A | 121.88 (14) |
C2—C3B—C4 | 121.16 (14) | O2—C11—H11A | 109.5 |
C2—C3B—H3 | 119.4 | O2—C11—H11B | 109.5 |
C4—C3B—H3 | 119.4 | H11A—C11—H11B | 109.5 |
C2A—C3D—C4A | 121.05 (14) | O2—C11—H11C | 109.5 |
C2A—C3D—H3A | 119.5 | H11A—C11—H11C | 109.5 |
C4A—C3D—H3A | 119.5 | H11B—C11—H11C | 109.5 |
C4—N1—N2—C3 | 142.58 (15) | C6—C7—C8—C9 | −1.2 (2) |
N2—N1—C4—C3B | −2.7 (2) | Cl1—C7—C8—C9 | 176.44 (12) |
N2—N1—C4—C10 | 179.62 (13) | C7—C8—C9—C10 | 0.5 (2) |
C9—NQ—C2—C3B | 1.7 (2) | C7—C8—C9—NQ | −178.16 (15) |
C2—NQ—C9—C8 | 177.72 (15) | NQ—C9—C10—C4 | 1.6 (2) |
C2—NQ—C9—C10 | −1.0 (2) | C8—C9—C10—C4 | −177.00 (14) |
N1—N2—C3—S1 | 178.10 (11) | C8—C9—C10—C5 | 0.6 (2) |
N1—N2—C3—N4 | −3.0 (2) | NQ—C9—C10—C5 | 179.25 (14) |
N2A—N1A—C4A—C10A | −175.11 (13) | NQA—C2A—C3D—C4A | 2.3 (3) |
C4A—N1A—N2A—C3A | 151.25 (15) | C2A—C3D—C4A—N1A | 179.94 (18) |
N2A—N1A—C4A—C3D | 3.7 (2) | C2A—C3D—C4A—C10A | −1.3 (2) |
C9A—NQA—C2A—C3D | −1.1 (3) | N1A—C4A—C10A—C5A | −0.5 (2) |
C2A—NQA—C9A—C8A | 178.24 (17) | N1A—C4A—C10A—C9A | 178.17 (15) |
C2A—NQA—C9A—C10A | −1.0 (2) | C3D—C4A—C10A—C5A | −179.44 (14) |
N1A—N2A—C3A—S1A | −179.14 (12) | C3D—C4A—C10A—C9A | −0.8 (2) |
N1A—N2A—C3A—N4A | 0.1 (2) | C10A—C5A—C6A—C7A | 0.1 (3) |
NQ—C2—C3B—C4 | −3.1 (2) | C6A—C5A—C10A—C4A | 177.65 (16) |
C2—C3B—C4—N1 | −174.30 (16) | C6A—C5A—C10A—C9A | −1.1 (2) |
C2—C3B—C4—C10 | 3.5 (2) | C5A—C6A—C7A—Cl1A | −179.17 (14) |
N1—C4—C10—C5 | −2.3 (2) | C5A—C6A—C7A—C8A | 0.7 (3) |
N1—C4—C10—C9 | 175.19 (14) | Cl1A—C7A—C8A—C9A | 179.50 (12) |
C3B—C4—C10—C5 | 179.66 (14) | C6A—C7A—C8A—C9A | −0.3 (2) |
C3B—C4—C10—C9 | −2.8 (2) | C7A—C8A—C9A—NQA | −179.93 (15) |
C10—C5—C6—C7 | 0.5 (2) | C7A—C8A—C9A—C10A | −0.7 (2) |
C6—C5—C10—C4 | 176.50 (14) | NQA—C9A—C10A—C4A | 1.9 (2) |
C6—C5—C10—C9 | −1.1 (2) | NQA—C9A—C10A—C5A | −179.40 (14) |
C5—C6—C7—Cl1 | −176.91 (12) | C8A—C9A—C10A—C4A | −177.34 (14) |
C5—C6—C7—C8 | 0.7 (2) | C8A—C9A—C10A—C5A | 1.4 (2) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z+1; (iv) −x+1, −y, −z+2; (v) −x+1, −y+1, −z+2; (vi) −x, −y+1, −z+1; (vii) x, y−1, z; (viii) −x+1, −y, −z+1; (ix) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O2 | 0.83 (2) | 2.113 (19) | 2.939 (2) | 172 (2) |
N2A—HN2A···S1Aviii | 0.786 (19) | 2.781 (19) | 3.5420 (15) | 163.7 (19) |
N4—H4NA···N1 | 0.924 (18) | 2.341 (17) | 2.683 (2) | 101.5 (13) |
N4—H4NA···O1vi | 0.924 (18) | 2.167 (18) | 3.007 (2) | 150.6 (15) |
N4—H4NB···N1Ax | 0.89 (2) | 2.35 (2) | 3.208 (2) | 163.4 (19) |
N4A—H4NC···N1A | 0.86 (2) | 2.20 (2) | 2.597 (2) | 108.1 (16) |
N4A—H4ND···N1 | 0.82 (2) | 2.28 (2) | 3.058 (2) | 158 (2) |
NQ—H1Q···O1 | 0.86 | 2.23 | 2.969 (2) | 144 |
NQA—H2Q···S1iv | 0.86 | 2.56 | 3.3440 (15) | 151 |
O1—H1A···S1Axi | 0.88 (4) | 2.61 (4) | 3.4675 (17) | 165 (3) |
O1—H1B···S1Avi | 0.81 (3) | 2.62 (3) | 3.432 (2) | 177 (2) |
O2—H2O···S1v | 0.85 (3) | 2.43 (3) | 3.2207 (15) | 155 (2) |
C3B—H3···O2 | 0.93 | 2.53 | 3.333 (2) | 145 |
Symmetry codes: (iv) −x+1, −y, −z+2; (v) −x+1, −y+1, −z+2; (vi) −x, −y+1, −z+1; (viii) −x+1, −y, −z+1; (x) x−1, y, z; (xi) x, y+1, z. |
C10H10ClN4S+·Cl− | F(000) = 592 |
Mr = 289.18 | Dx = 1.578 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 2277 reflections |
a = 9.4517 (6) Å | θ = 2.2–29.4° |
b = 7.8839 (5) Å | µ = 0.69 mm−1 |
c = 16.5172 (10) Å | T = 293 K |
β = 98.477 (5)° | Prismatic, colourless |
V = 1217.36 (14) Å3 | 0.22 × 0.17 × 0.12 mm |
Z = 4 |
Agilent Xcalibur Gemini Ultra diffractometer with Atlas detector | 2973 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1904 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 10.4186 pixels mm-1 | θmax = 29.5°, θmin = 2.2° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2014) | k = −7→10 |
Tmin = 0.944, Tmax = 1.000 | l = −20→21 |
8726 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0319P)2 + 0.0815P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.103 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.36 e Å−3 |
2973 reflections | Δρmin = −0.35 e Å−3 |
170 parameters |
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. Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. Item _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. |
x | y | z | Uiso*/Ueq | ||
Cl11 | 0.06195 (7) | 0.44805 (9) | 0.23521 (4) | 0.0364 (2) | |
Cl1 | −0.35755 (8) | 0.66636 (11) | 0.55457 (5) | 0.0552 (3) | |
S1 | 0.54665 (8) | 0.86733 (9) | 0.25829 (4) | 0.0422 (2) | |
N1 | 0.2161 (2) | 0.7087 (3) | 0.35553 (12) | 0.0282 (5) | |
N2 | 0.3499 (2) | 0.7240 (3) | 0.33059 (12) | 0.0308 (5) | |
C3A | 0.3840 (3) | 0.8615 (3) | 0.28812 (13) | 0.0280 (6) | |
C3 | 0.3053 (3) | 0.8407 (3) | 0.48349 (15) | 0.0353 (6) | |
H3 | 0.3946 | 0.8571 | 0.4676 | 0.042* | |
NQ | 0.1543 (2) | 0.8739 (3) | 0.58381 (12) | 0.0390 (6) | |
HNQ | 0.1423 | 0.9115 | 0.6312 | 0.047* | |
C6 | −0.1821 (3) | 0.6324 (3) | 0.44035 (15) | 0.0347 (6) | |
H6 | −0.2585 | 0.5783 | 0.4088 | 0.042* | |
N4 | 0.2910 (3) | 0.9868 (3) | 0.27668 (15) | 0.0410 (6) | |
C9 | 0.0426 (3) | 0.7936 (3) | 0.53616 (14) | 0.0312 (6) | |
C7 | −0.1961 (3) | 0.6932 (3) | 0.51826 (15) | 0.0347 (6) | |
C10 | 0.0610 (3) | 0.7345 (3) | 0.45785 (13) | 0.0259 (6) | |
C4 | 0.1966 (3) | 0.7605 (3) | 0.43074 (13) | 0.0265 (6) | |
C5 | −0.0563 (3) | 0.6527 (3) | 0.41095 (14) | 0.0308 (6) | |
H5 | −0.0474 | 0.6120 | 0.3591 | 0.037* | |
C8 | −0.0864 (3) | 0.7721 (3) | 0.56650 (15) | 0.0348 (6) | |
H8 | −0.0972 | 0.8108 | 0.6184 | 0.042* | |
C2 | 0.2798 (3) | 0.8949 (4) | 0.55868 (16) | 0.0428 (7) | |
H2 | 0.3530 | 0.9481 | 0.5933 | 0.051* | |
H2N | 0.397 (3) | 0.629 (4) | 0.3240 (16) | 0.047 (9)* | |
H4B | 0.325 (4) | 1.088 (4) | 0.255 (2) | 0.075 (11)* | |
H4A | 0.208 (3) | 0.978 (4) | 0.2832 (16) | 0.049 (10)* | |
H1N | 0.147 (3) | 0.645 (4) | 0.3213 (18) | 0.062 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl11 | 0.0404 (4) | 0.0407 (4) | 0.0296 (3) | −0.0076 (3) | 0.0102 (3) | −0.0041 (3) |
Cl1 | 0.0404 (5) | 0.0683 (6) | 0.0637 (5) | 0.0075 (4) | 0.0306 (4) | 0.0161 (4) |
S1 | 0.0382 (4) | 0.0337 (4) | 0.0610 (5) | −0.0023 (3) | 0.0286 (3) | −0.0005 (3) |
N1 | 0.0260 (12) | 0.0336 (13) | 0.0272 (11) | −0.0045 (10) | 0.0108 (9) | −0.0026 (10) |
N2 | 0.0290 (13) | 0.0282 (13) | 0.0389 (12) | 0.0036 (11) | 0.0173 (9) | 0.0035 (10) |
C3A | 0.0322 (15) | 0.0299 (15) | 0.0235 (12) | −0.0035 (12) | 0.0089 (10) | −0.0073 (11) |
C3 | 0.0278 (15) | 0.0426 (17) | 0.0359 (15) | −0.0005 (12) | 0.0058 (11) | −0.0047 (12) |
NQ | 0.0438 (15) | 0.0462 (15) | 0.0274 (11) | 0.0046 (12) | 0.0063 (10) | −0.0098 (10) |
C6 | 0.0311 (15) | 0.0403 (17) | 0.0336 (14) | −0.0037 (13) | 0.0077 (11) | 0.0032 (12) |
N4 | 0.0322 (16) | 0.0369 (16) | 0.0578 (16) | 0.0028 (13) | 0.0193 (12) | 0.0078 (12) |
C9 | 0.0363 (16) | 0.0313 (15) | 0.0266 (13) | 0.0059 (12) | 0.0070 (11) | 0.0017 (11) |
C7 | 0.0329 (16) | 0.0358 (16) | 0.0390 (15) | 0.0096 (13) | 0.0176 (12) | 0.0148 (12) |
C10 | 0.0289 (14) | 0.0253 (14) | 0.0248 (12) | 0.0043 (11) | 0.0086 (10) | 0.0045 (10) |
C4 | 0.0288 (15) | 0.0231 (14) | 0.0284 (13) | 0.0050 (11) | 0.0070 (10) | 0.0028 (11) |
C5 | 0.0337 (15) | 0.0349 (16) | 0.0252 (13) | −0.0012 (12) | 0.0088 (11) | 0.0021 (11) |
C8 | 0.0424 (18) | 0.0354 (16) | 0.0297 (13) | 0.0096 (13) | 0.0153 (12) | 0.0028 (12) |
C2 | 0.0366 (17) | 0.0517 (19) | 0.0385 (16) | −0.0007 (15) | 0.0004 (12) | −0.0073 (14) |
Cl1—C7 | 1.733 (3) | C6—C5 | 1.358 (3) |
S1—C3A | 1.683 (2) | C6—C7 | 1.398 (3) |
N1—C4 | 1.346 (3) | C6—H6 | 0.9300 |
N1—N2 | 1.392 (3) | N4—H4B | 0.95 (3) |
N1—H1N | 0.94 (3) | N4—H4A | 0.81 (3) |
N2—C3A | 1.356 (3) | C9—C8 | 1.395 (3) |
N2—H2N | 0.88 (3) | C9—C10 | 1.409 (3) |
C3A—N4 | 1.317 (3) | C7—C8 | 1.362 (4) |
C3—C2 | 1.368 (4) | C10—C5 | 1.411 (3) |
C3—C4 | 1.396 (3) | C10—C4 | 1.434 (3) |
C3—H3 | 0.9300 | C5—H5 | 0.9300 |
NQ—C2 | 1.324 (3) | C8—H8 | 0.9300 |
NQ—C9 | 1.375 (3) | C2—H2 | 0.9300 |
NQ—HNQ | 0.8600 | ||
Cl1···C3i | 3.510 (3) | Cl11···HNQ | 2.2700 |
Cl1···S1ii | 3.6210 (11) | Cl11···H8ix | 3.1400 |
Cl11···S1iii | 3.7398 (10) | Cl11···H5x | 2.7500 |
Cl1···N1iv | 3.486 (2) | S1···N2xi | 3.383 (2) |
Cl11···NQv | 3.103 (2) | S1···N4iii | 3.457 (3) |
Cl11···N4vi | 3.327 (3) | S1···Cl11xi | 3.7398 (10) |
Cl11···N1 | 3.073 (2) | S1···H4Biii | 2.54 (3) |
Cl11···N1vi | 3.399 (2) | S1···H2Nxi | 2.57 (3) |
Cl1···H3vii | 2.9700 | S1···H2xii | 2.8900 |
Cl1···H2Niv | 3.13 (3) | N1···N4 | 2.698 (3) |
Cl11···H1N | 2.18 (3) | N4···C4 | 3.335 (3) |
Cl11···H4Avi | 2.54 (3) | N1···H4A | 2.43 (3) |
Cl11···H8 | 2.9600 | N1···H5 | 2.6100 |
Cl11···H5viii | 3.0700 | N2···H3 | 2.4700 |
C4—N1—N2 | 120.0 (2) | NQ—C9—C8 | 119.2 (2) |
C4—N1—H1N | 122.3 (18) | NQ—C9—C10 | 119.3 (2) |
N2—N1—H1N | 116.9 (18) | C8—C9—C10 | 121.5 (2) |
C3A—N2—N1 | 121.2 (2) | C8—C7—C6 | 121.9 (2) |
C3A—N2—H2N | 116.7 (18) | C8—C7—Cl1 | 119.1 (2) |
N1—N2—H2N | 117.3 (18) | C6—C7—Cl1 | 119.0 (2) |
N4—C3A—N2 | 118.0 (2) | C9—C10—C5 | 117.5 (2) |
N4—C3A—S1 | 123.8 (2) | C9—C10—C4 | 118.4 (2) |
N2—C3A—S1 | 118.1 (2) | C5—C10—C4 | 124.1 (2) |
C2—C3—C4 | 119.8 (3) | N1—C4—C3 | 121.7 (2) |
C2—C3—H3 | 120.1 | N1—C4—C10 | 119.7 (2) |
C4—C3—H3 | 120.1 | C3—C4—C10 | 118.6 (2) |
C2—NQ—C9 | 121.7 (2) | C6—C5—C10 | 121.0 (2) |
C2—NQ—HNQ | 119.1 | C6—C5—H5 | 119.5 |
C9—NQ—HNQ | 119.1 | C10—C5—H5 | 119.5 |
C5—C6—C7 | 119.7 (2) | C7—C8—C9 | 118.4 (2) |
C5—C6—H6 | 120.1 | C7—C8—H8 | 120.8 |
C7—C6—H6 | 120.1 | C9—C8—H8 | 120.8 |
C3A—N4—H4B | 115 (2) | NQ—C2—C3 | 122.1 (3) |
C3A—N4—H4A | 124 (2) | NQ—C2—H2 | 118.9 |
H4B—N4—H4A | 121 (3) | C3—C2—H2 | 118.9 |
C4—N1—N2—C3A | −93.9 (3) | C3—C4—C10—C9 | 1.0 (3) |
N2—N1—C4—C3 | 4.4 (4) | C10—C5—C6—C7 | 0.0 (4) |
N2—N1—C4—C10 | −176.1 (2) | C6—C5—C10—C4 | −179.9 (2) |
C9—NQ—C2—C3 | 1.1 (4) | C6—C5—C10—C9 | 0.2 (3) |
C2—NQ—C9—C8 | 178.7 (3) | C5—C6—C7—Cl1 | 179.89 (19) |
C2—NQ—C9—C10 | −1.1 (4) | C5—C6—C7—C8 | −0.4 (4) |
N1—N2—C3A—S1 | −178.46 (17) | Cl1—C7—C8—C9 | −179.62 (19) |
N1—N2—C3A—N4 | 5.3 (3) | C6—C7—C8—C9 | 0.7 (4) |
NQ—C2—C3—C4 | 0.1 (4) | C7—C8—C9—NQ | 179.6 (2) |
C2—C3—C4—N1 | 178.5 (2) | C7—C8—C9—C10 | −0.5 (4) |
C2—C3—C4—C10 | −1.1 (4) | NQ—C9—C10—C4 | 0.1 (3) |
N1—C4—C10—C5 | 1.6 (4) | NQ—C9—C10—C5 | 180.0 (2) |
N1—C4—C10—C9 | −178.5 (2) | C8—C9—C10—C4 | −179.8 (2) |
C3—C4—C10—C5 | −178.9 (2) | C8—C9—C10—C5 | 0.1 (4) |
Symmetry codes: (i) x−1, y, z; (ii) x−1, −y+3/2, z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) −x, −y+1, −z+1; (v) x, −y+3/2, z−1/2; (vi) −x, y−1/2, −z+1/2; (vii) x+1, y, z; (viii) −x, −y+1, −z; (ix) −x, y+1/2, −z−1/2; (x) x, −y−1/2, z−3/2; (xi) −x+1, y+1/2, −z+1/2; (xii) −x−1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
NQ—HNQ···Cl11xiii | 0.86 | 2.27 | 3.103 (2) | 164 |
N1—H1N···Cl11 | 0.94 (3) | 2.18 (3) | 3.073 (2) | 158 (3) |
N2—H2N···S1iii | 0.89 (3) | 2.57 (3) | 3.383 (2) | 153 (2) |
N4—H4A···N1 | 0.81 (3) | 2.43 (3) | 2.698 (3) | 100 (2) |
N4—H4A···Cl11xiv | 0.81 (3) | 2.54 (3) | 3.327 (3) | 166 (2) |
N4—H4B···S1xi | 0.95 (3) | 2.54 (3) | 3.457 (3) | 163 (3) |
C5—H5···Cl11 | 0.93 | 2.75 | 3.638 (3) | 161 |
Symmetry codes: (iii) −x+1, y−1/2, −z+1/2; (xi) −x+1, y+1/2, −z+1/2; (xiii) x, −y+3/2, z+1/2; (xiv) −x, y+1/2, −z+1/2. |