Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618013980/sk3709sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618013980/sk37096sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618013980/sk37097sup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618013980/sk37096sup4.cml |
CCDC references: 1871197; 1871196
Data collection: COLLECT (Bruker, 2004) for (6); CrysAlis PRO (Agilent, 2014) for (7). Cell refinement: SCALEPACK (Otwinowski & Minor, 1997) for (6); CrysAlis PRO (Agilent, 2014) for (7). Data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997) for (6); CrysAlis PRO (Agilent, 2014) for (7). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (6); SIR97 (Altomare et al., 1999) for (7). For both structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
C15H17ClN4O | Z = 4 |
Mr = 304.77 | F(000) = 640 |
Triclinic, P1 | Dx = 1.347 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1010 (6) Å | Cell parameters from 37828 reflections |
b = 13.1770 (7) Å | θ = 1.0–27.5° |
c = 13.3280 (7) Å | µ = 0.26 mm−1 |
α = 70.334 (4)° | T = 130 K |
β = 89.469 (3)° | Needle, yellow |
γ = 86.582 (4)° | 0.55 × 0.08 × 0.05 mm |
V = 1502.34 (15) Å3 |
Nonius KappaCCD diffractometer | 6666 independent reflections |
Horizonally mounted graphite crystal monochromator | 4750 reflections with I > 2σ(I) |
Detector resolution: 9 pixels mm-1 | Rint = 0.086 |
CCD scans | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −11→10 |
Tmin = 0.975, Tmax = 0.987 | k = −16→17 |
23208 measured reflections | l = −17→17 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.051 | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.4874P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.128 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.29 e Å−3 |
6816 reflections | Δρmin = −0.37 e Å−3 |
390 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0086 (11) |
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 | ||
Cl1A | −0.62763 (8) | 0.91644 (5) | 0.39818 (5) | 0.04953 (19) | |
C10A | −0.3503 (2) | 0.71608 (17) | 0.30962 (16) | 0.0311 (5) | |
H10A | −0.2768 | 0.6608 | 0.3425 | 0.037* | |
C9A | −0.4239 (3) | 0.77106 (18) | 0.36903 (17) | 0.0342 (5) | |
H9A | −0.3994 | 0.7545 | 0.4422 | 0.041* | |
C8A | −0.5323 (3) | 0.84957 (17) | 0.32211 (17) | 0.0323 (5) | |
C7A | −0.5678 (2) | 0.87755 (17) | 0.21433 (17) | 0.0330 (5) | |
H7A | −0.6423 | 0.9324 | 0.1824 | 0.04* | |
C6A | −0.4924 (2) | 0.82391 (17) | 0.15490 (17) | 0.0305 (4) | |
H6A | −0.5149 | 0.8432 | 0.0811 | 0.037* | |
C5A | −0.3839 (2) | 0.74185 (16) | 0.20054 (16) | 0.0266 (4) | |
C4A | −0.3107 (2) | 0.68754 (16) | 0.13374 (16) | 0.0277 (4) | |
H4A | −0.3388 | 0.7149 | 0.0606 | 0.033* | |
C3A | −0.2090 (2) | 0.60420 (16) | 0.16019 (15) | 0.0262 (4) | |
N1A | −0.14641 (18) | 0.54451 (13) | 0.25979 (13) | 0.0266 (4) | |
C1A | −0.0518 (2) | 0.47417 (16) | 0.24102 (15) | 0.0260 (4) | |
N2A | −0.0439 (2) | 0.48136 (14) | 0.13419 (13) | 0.0276 (4) | |
C2A | −0.1419 (2) | 0.56323 (16) | 0.07823 (16) | 0.0272 (4) | |
O1A | −0.16635 (16) | 0.59341 (12) | −0.01850 (11) | 0.0326 (3) | |
N3A | 0.02685 (19) | 0.39613 (14) | 0.31594 (13) | 0.0293 (4) | |
C13A | 0.0278 (2) | 0.39656 (17) | 0.42565 (15) | 0.0309 (5) | |
H3AB | −0.0571 | 0.4423 | 0.4362 | 0.037* | |
H3AA | 0.1191 | 0.4273 | 0.4393 | 0.037* | |
C14A | 0.0194 (2) | 0.28217 (17) | 0.50321 (16) | 0.0326 (5) | |
H4AB | 0.0307 | 0.2822 | 0.577 | 0.039* | |
H4AA | −0.0784 | 0.2557 | 0.4967 | 0.039* | |
N4A | 0.1338 (2) | 0.20992 (14) | 0.48228 (13) | 0.0341 (4) | |
C12A | 0.1162 (3) | 0.20739 (17) | 0.37445 (16) | 0.0322 (5) | |
H2AA | 0.0178 | 0.1826 | 0.3664 | 0.039* | |
H2AB | 0.1914 | 0.1557 | 0.3617 | 0.039* | |
C11A | 0.1326 (2) | 0.31860 (17) | 0.29359 (16) | 0.0297 (4) | |
H1AB | 0.2339 | 0.3407 | 0.297 | 0.036* | |
H1AA | 0.1149 | 0.3171 | 0.2209 | 0.036* | |
C15A | 0.1299 (4) | 0.1018 (2) | 0.5611 (2) | 0.0558 (7) | |
H5AA | 0.0345 | 0.0726 | 0.5567 | 0.084* | |
H5AB | 0.1436 | 0.1056 | 0.6326 | 0.084* | |
H5AC | 0.2088 | 0.0548 | 0.5468 | 0.084* | |
Cl1B | −0.12179 (8) | 0.91476 (5) | −0.17042 (5) | 0.04765 (18) | |
C6B | 0.0045 (2) | 0.82602 (17) | 0.13497 (16) | 0.0299 (4) | |
H6B | −0.0193 | 0.8465 | 0.1953 | 0.036* | |
C7B | −0.0686 (2) | 0.87919 (17) | 0.03893 (17) | 0.0321 (5) | |
H7B | −0.1425 | 0.9349 | 0.0334 | 0.039* | |
C8B | −0.0315 (2) | 0.84918 (17) | −0.04867 (16) | 0.0316 (5) | |
C9B | 0.0753 (2) | 0.76841 (17) | −0.04248 (17) | 0.0326 (5) | |
H9B | 0.0996 | 0.7496 | −0.1037 | 0.039* | |
C10B | 0.1467 (2) | 0.71492 (17) | 0.05397 (16) | 0.0300 (4) | |
H10B | 0.2197 | 0.6588 | 0.0588 | 0.036* | |
C5B | 0.1121 (2) | 0.74308 (16) | 0.14469 (16) | 0.0270 (4) | |
C4B | 0.1849 (2) | 0.69003 (16) | 0.24720 (15) | 0.0277 (4) | |
H4B | 0.1568 | 0.7177 | 0.3022 | 0.033* | |
C3B | 0.2871 (2) | 0.60666 (16) | 0.27455 (15) | 0.0267 (4) | |
N1B | 0.34860 (19) | 0.54752 (13) | 0.21348 (13) | 0.0272 (4) | |
C1B | 0.4450 (2) | 0.47685 (16) | 0.27680 (15) | 0.0266 (4) | |
N2B | 0.4536 (2) | 0.48366 (14) | 0.37867 (13) | 0.0283 (4) | |
C2B | 0.3561 (2) | 0.56510 (17) | 0.38259 (16) | 0.0283 (4) | |
O1B | 0.33332 (16) | 0.59502 (12) | 0.46016 (11) | 0.0335 (3) | |
N3B | 0.5231 (2) | 0.40068 (14) | 0.25052 (13) | 0.0298 (4) | |
C11B | 0.6296 (2) | 0.32238 (17) | 0.32145 (16) | 0.0296 (4) | |
H1BB | 0.6112 | 0.318 | 0.3961 | 0.035* | |
H1BA | 0.7306 | 0.3459 | 0.3029 | 0.035* | |
C12B | 0.6158 (3) | 0.21248 (17) | 0.31060 (16) | 0.0332 (5) | |
H2BB | 0.6915 | 0.1604 | 0.3557 | 0.04* | |
H2BA | 0.5177 | 0.1861 | 0.3353 | 0.04* | |
N4B | 0.6348 (2) | 0.21946 (14) | 0.19935 (14) | 0.0330 (4) | |
C14B | 0.5185 (2) | 0.29242 (18) | 0.13345 (17) | 0.0327 (5) | |
H4BA | 0.4213 | 0.2642 | 0.1582 | 0.039* | |
H4BB | 0.53 | 0.2955 | 0.0586 | 0.039* | |
C13B | 0.5245 (3) | 0.40405 (17) | 0.13912 (16) | 0.0320 (5) | |
H3BB | 0.6151 | 0.4366 | 0.1044 | 0.038* | |
H3BA | 0.4389 | 0.4498 | 0.1003 | 0.038* | |
C15B | 0.6314 (4) | 0.1126 (2) | 0.1890 (2) | 0.0530 (7) | |
H5BB | 0.7114 | 0.0651 | 0.2318 | 0.079* | |
H5BC | 0.6437 | 0.1189 | 0.1141 | 0.079* | |
H5BA | 0.5367 | 0.0822 | 0.2142 | 0.079* | |
H2A | 0.026 (3) | 0.451 (2) | 0.104 (2) | 0.048 (8)* | |
H2B | 0.525 (3) | 0.455 (2) | 0.425 (2) | 0.043 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.0667 (4) | 0.0423 (3) | 0.0392 (3) | 0.0138 (3) | 0.0113 (3) | −0.0164 (3) |
C10A | 0.0307 (11) | 0.0297 (11) | 0.0316 (10) | 0.0028 (9) | −0.0013 (9) | −0.0093 (9) |
C9A | 0.0397 (13) | 0.0343 (12) | 0.0284 (10) | −0.0015 (10) | 0.0023 (9) | −0.0105 (9) |
C8A | 0.0395 (12) | 0.0263 (10) | 0.0330 (11) | 0.0016 (9) | 0.0061 (9) | −0.0131 (9) |
C7A | 0.0322 (11) | 0.0286 (11) | 0.0380 (11) | 0.0040 (9) | −0.0015 (9) | −0.0118 (9) |
C6A | 0.0313 (11) | 0.0304 (11) | 0.0297 (10) | 0.0019 (9) | −0.0034 (9) | −0.0106 (9) |
C5A | 0.0248 (10) | 0.0263 (10) | 0.0292 (10) | −0.0017 (8) | 0.0002 (8) | −0.0097 (8) |
C4A | 0.0276 (11) | 0.0294 (10) | 0.0262 (10) | −0.0019 (8) | −0.0013 (8) | −0.0097 (8) |
C3A | 0.0253 (10) | 0.0283 (10) | 0.0248 (9) | −0.0023 (8) | 0.0002 (8) | −0.0084 (8) |
N1A | 0.0272 (9) | 0.0264 (8) | 0.0254 (8) | 0.0012 (7) | 0.0016 (7) | −0.0084 (7) |
C1A | 0.0264 (10) | 0.0273 (10) | 0.0245 (9) | −0.0026 (8) | 0.0033 (8) | −0.0088 (8) |
N2A | 0.0298 (9) | 0.0285 (9) | 0.0232 (8) | 0.0039 (7) | 0.0026 (7) | −0.0080 (7) |
C2A | 0.0227 (10) | 0.0296 (10) | 0.0299 (10) | −0.0012 (8) | 0.0002 (8) | −0.0110 (8) |
O1A | 0.0342 (8) | 0.0376 (8) | 0.0252 (7) | 0.0060 (7) | −0.0028 (6) | −0.0107 (6) |
N3A | 0.0322 (10) | 0.0302 (9) | 0.0235 (8) | 0.0071 (8) | 0.0004 (7) | −0.0078 (7) |
C13A | 0.0357 (12) | 0.0323 (11) | 0.0245 (10) | 0.0046 (9) | 0.0002 (8) | −0.0104 (9) |
C14A | 0.0358 (12) | 0.0362 (12) | 0.0238 (10) | −0.0001 (10) | 0.0027 (9) | −0.0079 (9) |
N4A | 0.0431 (11) | 0.0289 (9) | 0.0261 (9) | 0.0054 (8) | −0.0031 (8) | −0.0048 (7) |
C12A | 0.0379 (12) | 0.0284 (11) | 0.0296 (10) | 0.0033 (9) | −0.0018 (9) | −0.0096 (9) |
C11A | 0.0307 (11) | 0.0295 (10) | 0.0280 (10) | 0.0055 (9) | 0.0024 (8) | −0.0099 (8) |
C15A | 0.087 (2) | 0.0360 (13) | 0.0345 (13) | 0.0085 (14) | −0.0042 (13) | −0.0009 (10) |
Cl1B | 0.0605 (4) | 0.0449 (3) | 0.0359 (3) | 0.0207 (3) | −0.0181 (3) | −0.0149 (3) |
C6B | 0.0316 (11) | 0.0286 (10) | 0.0307 (10) | 0.0001 (9) | 0.0016 (9) | −0.0121 (9) |
C7B | 0.0327 (12) | 0.0283 (11) | 0.0345 (11) | 0.0040 (9) | −0.0009 (9) | −0.0103 (9) |
C8B | 0.0354 (12) | 0.0277 (10) | 0.0309 (10) | 0.0019 (9) | −0.0061 (9) | −0.0092 (9) |
C9B | 0.0360 (12) | 0.0343 (11) | 0.0288 (10) | 0.0029 (9) | −0.0021 (9) | −0.0131 (9) |
C10B | 0.0286 (11) | 0.0310 (11) | 0.0303 (10) | 0.0030 (9) | −0.0029 (8) | −0.0109 (9) |
C5B | 0.0257 (10) | 0.0259 (10) | 0.0288 (10) | −0.0029 (8) | −0.0013 (8) | −0.0082 (8) |
C4B | 0.0274 (11) | 0.0307 (11) | 0.0256 (10) | −0.0026 (9) | 0.0000 (8) | −0.0100 (8) |
C3B | 0.0273 (10) | 0.0292 (10) | 0.0243 (9) | −0.0046 (8) | −0.0002 (8) | −0.0095 (8) |
N1B | 0.0297 (9) | 0.0264 (9) | 0.0251 (8) | 0.0000 (7) | −0.0031 (7) | −0.0084 (7) |
C1B | 0.0295 (11) | 0.0261 (10) | 0.0241 (9) | −0.0026 (8) | −0.0034 (8) | −0.0080 (8) |
N2B | 0.0304 (9) | 0.0301 (9) | 0.0242 (8) | 0.0011 (8) | −0.0046 (7) | −0.0092 (7) |
C2B | 0.0265 (11) | 0.0306 (11) | 0.0272 (10) | −0.0040 (9) | −0.0007 (8) | −0.0087 (8) |
O1B | 0.0338 (8) | 0.0415 (9) | 0.0270 (7) | 0.0029 (7) | −0.0032 (6) | −0.0149 (7) |
N3B | 0.0361 (10) | 0.0293 (9) | 0.0234 (8) | 0.0050 (8) | −0.0073 (7) | −0.0089 (7) |
C11B | 0.0298 (11) | 0.0308 (11) | 0.0263 (10) | 0.0034 (9) | −0.0054 (8) | −0.0080 (8) |
C12B | 0.0409 (12) | 0.0292 (11) | 0.0274 (10) | 0.0007 (9) | −0.0011 (9) | −0.0070 (8) |
N4B | 0.0426 (11) | 0.0278 (9) | 0.0288 (9) | 0.0007 (8) | −0.0001 (8) | −0.0104 (7) |
C14B | 0.0340 (12) | 0.0384 (12) | 0.0283 (10) | −0.0010 (9) | −0.0028 (9) | −0.0145 (9) |
C13B | 0.0380 (12) | 0.0345 (11) | 0.0233 (10) | 0.0033 (9) | −0.0045 (9) | −0.0101 (8) |
C15B | 0.088 (2) | 0.0310 (13) | 0.0414 (13) | 0.0004 (13) | −0.0010 (14) | −0.0145 (11) |
Cl1A—C8A | 1.747 (2) | Cl1B—C8B | 1.747 (2) |
C10A—C9A | 1.385 (3) | C6B—C7B | 1.389 (3) |
C10A—C5A | 1.409 (3) | C6B—C5B | 1.397 (3) |
C10A—H10A | 0.95 | C6B—H6B | 0.95 |
C9A—C8A | 1.374 (3) | C7B—C8B | 1.386 (3) |
C9A—H9A | 0.95 | C7B—H7B | 0.95 |
C8A—C7A | 1.393 (3) | C8B—C9B | 1.379 (3) |
C7A—C6A | 1.381 (3) | C9B—C10B | 1.387 (3) |
C7A—H7A | 0.95 | C9B—H9B | 0.95 |
C6A—C5A | 1.398 (3) | C10B—C5B | 1.407 (3) |
C6A—H6A | 0.95 | C10B—H10B | 0.95 |
C5A—C4A | 1.453 (3) | C5B—C4B | 1.454 (3) |
C4A—C3A | 1.346 (3) | C4B—C3B | 1.349 (3) |
C4A—H4A | 0.95 | C4B—H4B | 0.95 |
C3A—N1A | 1.401 (3) | C3B—N1B | 1.396 (3) |
C3A—C2A | 1.484 (3) | C3B—C2B | 1.488 (3) |
N1A—C1A | 1.312 (3) | N1B—C1B | 1.318 (3) |
C1A—N3A | 1.342 (3) | C1B—N3B | 1.335 (3) |
C1A—N2A | 1.396 (2) | C1B—N2B | 1.394 (2) |
N2A—C2A | 1.368 (3) | N2B—C2B | 1.365 (3) |
N2A—H2A | 0.89 (3) | N2B—H2B | 0.88 (3) |
C2A—O1A | 1.233 (2) | C2B—O1B | 1.236 (2) |
N3A—C11A | 1.463 (3) | N3B—C11B | 1.462 (3) |
N3A—C13A | 1.464 (2) | N3B—C13B | 1.470 (2) |
C13A—C14A | 1.520 (3) | C11B—C12B | 1.516 (3) |
C13A—H3AB | 0.99 | C11B—H1BB | 0.99 |
C13A—H3AA | 0.99 | C11B—H1BA | 0.99 |
C14A—N4A | 1.457 (3) | C12B—N4B | 1.464 (3) |
C14A—H4AB | 0.99 | C12B—H2BB | 0.99 |
C14A—H4AA | 0.99 | C12B—H2BA | 0.99 |
N4A—C12A | 1.459 (3) | N4B—C15B | 1.463 (3) |
N4A—C15A | 1.460 (3) | N4B—C14B | 1.464 (3) |
C12A—C11A | 1.514 (3) | C14B—C13B | 1.502 (3) |
C12A—H2AA | 0.99 | C14B—H4BA | 0.99 |
C12A—H2AB | 0.99 | C14B—H4BB | 0.99 |
C11A—H1AB | 0.99 | C13B—H3BB | 0.99 |
C11A—H1AA | 0.99 | C13B—H3BA | 0.99 |
C15A—H5AA | 0.98 | C15B—H5BB | 0.98 |
C15A—H5AB | 0.98 | C15B—H5BC | 0.98 |
C15A—H5AC | 0.98 | C15B—H5BA | 0.98 |
C9A—C10A—C5A | 120.3 (2) | C7B—C6B—C5B | 121.39 (19) |
C9A—C10A—H10A | 119.9 | C7B—C6B—H6B | 119.3 |
C5A—C10A—H10A | 119.9 | C5B—C6B—H6B | 119.3 |
C8A—C9A—C10A | 120.0 (2) | C8B—C7B—C6B | 118.6 (2) |
C8A—C9A—H9A | 120 | C8B—C7B—H7B | 120.7 |
C10A—C9A—H9A | 120 | C6B—C7B—H7B | 120.7 |
C9A—C8A—C7A | 121.28 (19) | C9B—C8B—C7B | 121.73 (19) |
C9A—C8A—Cl1A | 119.76 (17) | C9B—C8B—Cl1B | 118.78 (16) |
C7A—C8A—Cl1A | 118.96 (17) | C7B—C8B—Cl1B | 119.50 (17) |
C6A—C7A—C8A | 118.6 (2) | C8B—C9B—C10B | 119.36 (19) |
C6A—C7A—H7A | 120.7 | C8B—C9B—H9B | 120.3 |
C8A—C7A—H7A | 120.7 | C10B—C9B—H9B | 120.3 |
C7A—C6A—C5A | 121.7 (2) | C9B—C10B—C5B | 120.6 (2) |
C7A—C6A—H6A | 119.2 | C9B—C10B—H10B | 119.7 |
C5A—C6A—H6A | 119.2 | C5B—C10B—H10B | 119.7 |
C6A—C5A—C10A | 118.18 (19) | C6B—C5B—C10B | 118.35 (19) |
C6A—C5A—C4A | 118.78 (18) | C6B—C5B—C4B | 119.07 (18) |
C10A—C5A—C4A | 123.03 (19) | C10B—C5B—C4B | 122.58 (19) |
C3A—C4A—C5A | 129.53 (19) | C3B—C4B—C5B | 128.60 (19) |
C3A—C4A—H4A | 115.2 | C3B—C4B—H4B | 115.7 |
C5A—C4A—H4A | 115.2 | C5B—C4B—H4B | 115.7 |
C4A—C3A—N1A | 129.83 (18) | C4B—C3B—N1B | 129.58 (18) |
C4A—C3A—C2A | 121.24 (18) | C4B—C3B—C2B | 121.69 (18) |
N1A—C3A—C2A | 108.91 (17) | N1B—C3B—C2B | 108.72 (17) |
C1A—N1A—C3A | 105.05 (16) | C1B—N1B—C3B | 105.42 (16) |
N1A—C1A—N3A | 124.97 (18) | N1B—C1B—N3B | 124.58 (18) |
N1A—C1A—N2A | 114.36 (17) | N1B—C1B—N2B | 113.87 (18) |
N3A—C1A—N2A | 120.55 (18) | N3B—C1B—N2B | 121.45 (18) |
C2A—N2A—C1A | 107.39 (17) | C2B—N2B—C1B | 107.70 (17) |
C2A—N2A—H2A | 124.4 (17) | C2B—N2B—H2B | 124.7 (17) |
C1A—N2A—H2A | 126.7 (17) | C1B—N2B—H2B | 125.4 (17) |
O1A—C2A—N2A | 126.30 (18) | O1B—C2B—N2B | 126.29 (19) |
O1A—C2A—C3A | 129.43 (19) | O1B—C2B—C3B | 129.42 (19) |
N2A—C2A—C3A | 104.28 (16) | N2B—C2B—C3B | 104.29 (17) |
C1A—N3A—C11A | 124.28 (16) | C1B—N3B—C11B | 124.19 (16) |
C1A—N3A—C13A | 119.44 (16) | C1B—N3B—C13B | 119.67 (16) |
C11A—N3A—C13A | 115.53 (16) | C11B—N3B—C13B | 115.31 (16) |
N3A—C13A—C14A | 109.99 (17) | N3B—C11B—C12B | 109.68 (17) |
N3A—C13A—H3AB | 109.7 | N3B—C11B—H1BB | 109.7 |
C14A—C13A—H3AB | 109.7 | C12B—C11B—H1BB | 109.7 |
N3A—C13A—H3AA | 109.7 | N3B—C11B—H1BA | 109.7 |
C14A—C13A—H3AA | 109.7 | C12B—C11B—H1BA | 109.7 |
H3AB—C13A—H3AA | 108.2 | H1BB—C11B—H1BA | 108.2 |
N4A—C14A—C13A | 111.11 (17) | N4B—C12B—C11B | 110.13 (17) |
N4A—C14A—H4AB | 109.4 | N4B—C12B—H2BB | 109.6 |
C13A—C14A—H4AB | 109.4 | C11B—C12B—H2BB | 109.6 |
N4A—C14A—H4AA | 109.4 | N4B—C12B—H2BA | 109.6 |
C13A—C14A—H4AA | 109.4 | C11B—C12B—H2BA | 109.6 |
H4AB—C14A—H4AA | 108 | H2BB—C12B—H2BA | 108.1 |
C14A—N4A—C12A | 109.86 (16) | C15B—N4B—C12B | 110.62 (18) |
C14A—N4A—C15A | 110.54 (19) | C15B—N4B—C14B | 110.20 (18) |
C12A—N4A—C15A | 111.07 (18) | C12B—N4B—C14B | 109.58 (17) |
N4A—C12A—C11A | 110.26 (17) | N4B—C14B—C13B | 111.01 (17) |
N4A—C12A—H2AA | 109.6 | N4B—C14B—H4BA | 109.4 |
C11A—C12A—H2AA | 109.6 | C13B—C14B—H4BA | 109.4 |
N4A—C12A—H2AB | 109.6 | N4B—C14B—H4BB | 109.4 |
C11A—C12A—H2AB | 109.6 | C13B—C14B—H4BB | 109.4 |
H2AA—C12A—H2AB | 108.1 | H4BA—C14B—H4BB | 108 |
N3A—C11A—C12A | 109.65 (16) | N3B—C13B—C14B | 110.67 (17) |
N3A—C11A—H1AB | 109.7 | N3B—C13B—H3BB | 109.5 |
C12A—C11A—H1AB | 109.7 | C14B—C13B—H3BB | 109.5 |
N3A—C11A—H1AA | 109.7 | N3B—C13B—H3BA | 109.5 |
C12A—C11A—H1AA | 109.7 | C14B—C13B—H3BA | 109.5 |
H1AB—C11A—H1AA | 108.2 | H3BB—C13B—H3BA | 108.1 |
N4A—C15A—H5AA | 109.5 | N4B—C15B—H5BB | 109.5 |
N4A—C15A—H5AB | 109.5 | N4B—C15B—H5BC | 109.5 |
H5AA—C15A—H5AB | 109.5 | H5BB—C15B—H5BC | 109.5 |
N4A—C15A—H5AC | 109.5 | N4B—C15B—H5BA | 109.5 |
H5AA—C15A—H5AC | 109.5 | H5BB—C15B—H5BA | 109.5 |
H5AB—C15A—H5AC | 109.5 | H5BC—C15B—H5BA | 109.5 |
C5A—C10A—C9A—C8A | 1.3 (3) | C5B—C6B—C7B—C8B | −0.7 (3) |
C10A—C9A—C8A—C7A | −1.7 (3) | C6B—C7B—C8B—C9B | 0.1 (3) |
C10A—C9A—C8A—Cl1A | 178.51 (17) | C6B—C7B—C8B—Cl1B | 179.98 (17) |
C9A—C8A—C7A—C6A | 0.6 (3) | C7B—C8B—C9B—C10B | 0.6 (3) |
Cl1A—C8A—C7A—C6A | −179.65 (17) | Cl1B—C8B—C9B—C10B | −179.33 (17) |
C8A—C7A—C6A—C5A | 1.0 (3) | C8B—C9B—C10B—C5B | −0.6 (3) |
C7A—C6A—C5A—C10A | −1.3 (3) | C7B—C6B—C5B—C10B | 0.7 (3) |
C7A—C6A—C5A—C4A | 178.97 (19) | C7B—C6B—C5B—C4B | −179.9 (2) |
C9A—C10A—C5A—C6A | 0.2 (3) | C9B—C10B—C5B—C6B | 0.0 (3) |
C9A—C10A—C5A—C4A | 179.86 (19) | C9B—C10B—C5B—C4B | −179.44 (19) |
C6A—C5A—C4A—C3A | −176.7 (2) | C6B—C5B—C4B—C3B | 177.5 (2) |
C10A—C5A—C4A—C3A | 3.6 (3) | C10B—C5B—C4B—C3B | −3.1 (3) |
C5A—C4A—C3A—N1A | 1.3 (4) | C5B—C4B—C3B—N1B | −1.4 (4) |
C5A—C4A—C3A—C2A | −177.05 (19) | C5B—C4B—C3B—C2B | 177.02 (19) |
C4A—C3A—N1A—C1A | −178.9 (2) | C4B—C3B—N1B—C1B | 178.7 (2) |
C2A—C3A—N1A—C1A | −0.3 (2) | C2B—C3B—N1B—C1B | 0.1 (2) |
C3A—N1A—C1A—N3A | −175.81 (19) | C3B—N1B—C1B—N3B | 176.51 (19) |
C3A—N1A—C1A—N2A | 0.3 (2) | C3B—N1B—C1B—N2B | 0.1 (2) |
N1A—C1A—N2A—C2A | −0.1 (2) | N1B—C1B—N2B—C2B | −0.2 (2) |
N3A—C1A—N2A—C2A | 176.17 (18) | N3B—C1B—N2B—C2B | −176.81 (19) |
C1A—N2A—C2A—O1A | −179.7 (2) | C1B—N2B—C2B—O1B | −179.8 (2) |
C1A—N2A—C2A—C3A | −0.1 (2) | C1B—N2B—C2B—C3B | 0.3 (2) |
C4A—C3A—C2A—O1A | −1.4 (3) | C4B—C3B—C2B—O1B | 1.2 (3) |
N1A—C3A—C2A—O1A | 179.9 (2) | N1B—C3B—C2B—O1B | 179.9 (2) |
C4A—C3A—C2A—N2A | 178.96 (19) | C4B—C3B—C2B—N2B | −178.95 (19) |
N1A—C3A—C2A—N2A | 0.3 (2) | N1B—C3B—C2B—N2B | −0.3 (2) |
N1A—C1A—N3A—C11A | −179.68 (19) | N1B—C1B—N3B—C11B | −179.8 (2) |
N2A—C1A—N3A—C11A | 4.5 (3) | N2B—C1B—N3B—C11B | −3.7 (3) |
N1A—C1A—N3A—C13A | −10.0 (3) | N1B—C1B—N3B—C13B | 11.1 (3) |
N2A—C1A—N3A—C13A | 174.10 (18) | N2B—C1B—N3B—C13B | −172.75 (18) |
C1A—N3A—C13A—C14A | 139.4 (2) | C1B—N3B—C11B—C12B | 139.4 (2) |
C11A—N3A—C13A—C14A | −50.1 (2) | C13B—N3B—C11B—C12B | −51.1 (2) |
N3A—C13A—C14A—N4A | 53.2 (2) | N3B—C11B—C12B—N4B | 56.3 (2) |
C13A—C14A—N4A—C12A | −60.3 (2) | C11B—C12B—N4B—C15B | 176.3 (2) |
C13A—C14A—N4A—C15A | 176.73 (19) | C11B—C12B—N4B—C14B | −62.0 (2) |
C14A—N4A—C12A—C11A | 61.8 (2) | C15B—N4B—C14B—C13B | −177.43 (19) |
C15A—N4A—C12A—C11A | −175.6 (2) | C12B—N4B—C14B—C13B | 60.6 (2) |
C1A—N3A—C11A—C12A | −138.2 (2) | C1B—N3B—C13B—C14B | −140.2 (2) |
C13A—N3A—C11A—C12A | 51.8 (2) | C11B—N3B—C13B—C14B | 49.8 (2) |
N4A—C12A—C11A—N3A | −56.2 (2) | N4B—C14B—C13B—N3B | −53.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A···O1Ai | 0.89 (3) | 1.90 (3) | 2.785 (2) | 170 (3) |
N2B—H2B···O1Bii | 0.88 (3) | 1.92 (3) | 2.791 (2) | 170 (2) |
C11A—H1AA···O1Ai | 0.99 | 2.61 | 3.470 (2) | 146 |
C11B—H1BB···O1Bii | 0.99 | 2.61 | 3.459 (2) | 144 |
C9A—H9A···N4Aiii | 0.95 | 2.75 | 3.386 (3) | 125 |
C7A—H7A···Cl1Biv | 0.95 | 2.82 | 3.721 (2) | 158 |
C9B—H9B···N4Bv | 0.95 | 2.71 | 3.329 (3) | 123 |
C11A—H1AB···N1B | 0.99 | 2.83 | 3.551 (3) | 130 |
C11A—H1AB···N3B | 0.99 | 2.80 | 3.760 (3) | 164 |
C11B—H1BA···N1Avi | 0.99 | 2.78 | 3.530 (3) | 133 |
C11B—H1BA···N3Avi | 0.99 | 2.83 | 3.793 (3) | 163 |
C10A—H10A···N1A | 0.95 | 2.42 | 3.079 (3) | 126 |
C13A—H3AB···N1A | 0.99 | 2.40 | 2.828 (3) | 105 |
C10B—H10B···N1B | 0.95 | 2.36 | 3.032 (3) | 127 |
C13B—H3BA···N1B | 0.99 | 2.40 | 2.827 (3) | 105 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) −x−1, −y+2, −z; (v) −x+1, −y+1, −z; (vi) x+1, y, z. |
C15H18ClN4O+·C17H19N2O3S2− | Z = 2 |
Mr = 669.24 | F(000) = 704 |
Triclinic, P1 | Dx = 1.358 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 10.937 (5) Å | Cell parameters from 8081 reflections |
b = 11.384 (5) Å | θ = 2.9–28.7° |
c = 14.488 (5) Å | µ = 0.29 mm−1 |
α = 77.450 (5)° | T = 293 K |
β = 81.731 (5)° | Block, orange |
γ = 68.704 (5)° | 0.73 × 0.44 × 0.31 mm |
V = 1636.3 (12) Å3 |
Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer | 7624 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 5403 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.044 |
Detector resolution: 10.3756 pixels mm-1 | θmax = 28.7°, θmin = 2.9° |
ω scans | h = −14→14 |
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014) | k = −14→15 |
Tmin = 0.909, Tmax = 0.957 | l = −19→19 |
24554 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.0566P)2 + 1.1174P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
7624 reflections | Δρmax = 0.37 e Å−3 |
417 parameters | Δρmin = −0.32 e Å−3 |
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 | ||
S2C | 0.29532 (7) | 0.51459 (6) | 0.46823 (5) | 0.04314 (18) | |
S1C | 0.22340 (6) | 0.38262 (6) | 0.65738 (4) | 0.03392 (15) | |
Cl1B | 0.54731 (8) | −0.43244 (8) | 1.23409 (6) | 0.0626 (2) | |
O2C | 0.32983 (14) | 0.10410 (15) | 0.45841 (11) | 0.0306 (4) | |
O3C | 0.17516 (14) | 0.10814 (15) | 0.37266 (10) | 0.0292 (3) | |
N3C | 0.13688 (18) | 0.37354 (18) | 0.50475 (13) | 0.0298 (4) | |
O1B | −0.06244 (16) | −0.37089 (17) | 0.85512 (12) | 0.0379 (4) | |
N1B | 0.19650 (19) | −0.24601 (19) | 0.82770 (13) | 0.0319 (4) | |
N2B | 0.02659 (19) | −0.23471 (19) | 0.74836 (14) | 0.0305 (4) | |
O1C | 0.01463 (16) | 0.24140 (18) | 0.55524 (12) | 0.0399 (4) | |
N3B | 0.16276 (19) | −0.1108 (2) | 0.67924 (13) | 0.0343 (5) | |
C16C | 0.2289 (2) | 0.2978 (2) | 0.35296 (15) | 0.0274 (5) | |
H16C | 0.2116 | 0.3127 | 0.2868 | 0.033* | |
H16D | 0.3096 | 0.3134 | 0.3558 | 0.033* | |
N4B | 0.34313 (18) | −0.1368 (2) | 0.51527 (14) | 0.0302 (4) | |
C1B | 0.1326 (2) | −0.1966 (2) | 0.75084 (15) | 0.0296 (5) | |
N2C | 0.2883 (2) | 0.0508 (2) | 1.10927 (14) | 0.0368 (5) | |
C17C | 0.2459 (2) | 0.1593 (2) | 0.39721 (14) | 0.0242 (4) | |
C11B | 0.1148 (2) | −0.0800 (2) | 0.58467 (15) | 0.0319 (5) | |
H11A | 0.0961 | 0.0105 | 0.5598 | 0.038* | |
H11B | 0.0337 | −0.0977 | 0.5888 | 0.038* | |
C2C | 0.2158 (2) | 0.4250 (2) | 0.53479 (17) | 0.0328 (5) | |
C12B | 0.2153 (2) | −0.1577 (2) | 0.51802 (16) | 0.0322 (5) | |
H12A | 0.2278 | −0.2479 | 0.5393 | 0.039* | |
H12B | 0.1839 | −0.1322 | 0.4549 | 0.039* | |
C5B | 0.2463 (2) | −0.3939 (2) | 1.03561 (17) | 0.0354 (5) | |
C4B | 0.1471 (2) | −0.3858 (2) | 0.97460 (17) | 0.0353 (5) | |
H4B | 0.0901 | −0.43 | 1.0009 | 0.042* | |
C2B | 0.0181 (2) | −0.3169 (2) | 0.83254 (16) | 0.0313 (5) | |
C6B | 0.3553 (2) | −0.3569 (2) | 1.00237 (18) | 0.0388 (6) | |
H6B | 0.3654 | −0.3225 | 0.9386 | 0.047* | |
C7C | 0.1390 (2) | 0.1761 (3) | 0.83913 (16) | 0.0354 (5) | |
C12C | 0.1872 (2) | 0.2524 (3) | 0.87842 (17) | 0.0373 (6) | |
H12C | 0.1884 | 0.3307 | 0.8432 | 0.045* | |
C3B | 0.1280 (2) | −0.3223 (2) | 0.88513 (16) | 0.0316 (5) | |
C10C | 0.2354 (2) | 0.0939 (2) | 1.02347 (16) | 0.0350 (5) | |
C6C | 0.0996 (2) | 0.2060 (3) | 0.74394 (17) | 0.0360 (5) | |
H6C | 0.0479 | 0.1618 | 0.7333 | 0.043* | |
C4C | 0.0837 (2) | 0.2945 (2) | 0.57422 (17) | 0.0322 (5) | |
C5C | 0.1251 (2) | 0.2876 (2) | 0.66736 (16) | 0.0326 (5) | |
C14B | 0.3910 (2) | −0.1716 (2) | 0.61215 (17) | 0.0358 (6) | |
H14A | 0.4729 | −0.1558 | 0.6096 | 0.043* | |
H14B | 0.4074 | −0.262 | 0.6362 | 0.043* | |
C15C | 0.1158 (2) | 0.3904 (2) | 0.40425 (16) | 0.0328 (5) | |
H25C | 0.1067 | 0.4776 | 0.3738 | 0.039* | |
H25D | 0.0346 | 0.3769 | 0.3991 | 0.039* | |
C7B | 0.4488 (3) | −0.3704 (3) | 1.06268 (19) | 0.0419 (6) | |
H7B | 0.5224 | −0.3474 | 1.0394 | 0.05* | |
C8C | 0.1339 (2) | 0.0620 (3) | 0.89766 (17) | 0.0390 (6) | |
H8C | 0.0974 | 0.0121 | 0.8755 | 0.047* | |
C8B | 0.4316 (3) | −0.4182 (3) | 1.15751 (19) | 0.0446 (7) | |
C13C | 0.3488 (2) | 0.1232 (3) | 1.14759 (17) | 0.0377 (6) | |
H13C | 0.3427 | 0.1015 | 1.2162 | 0.045* | |
H13D | 0.3005 | 0.214 | 1.1299 | 0.045* | |
C14C | 0.3111 (3) | −0.0815 (3) | 1.15857 (18) | 0.0426 (6) | |
H14C | 0.3882 | −0.1097 | 1.1944 | 0.051* | |
H14D | 0.3294 | −0.1363 | 1.1119 | 0.051* | |
C11C | 0.2324 (2) | 0.2134 (3) | 0.96764 (16) | 0.0360 (5) | |
H11C | 0.2617 | 0.2669 | 0.992 | 0.043* | |
C15B | 0.4425 (2) | −0.2051 (3) | 0.4465 (2) | 0.0426 (6) | |
H15A | 0.522 | −0.1872 | 0.445 | 0.064* | |
H15B | 0.4094 | −0.1769 | 0.3846 | 0.064* | |
H15C | 0.4604 | −0.2957 | 0.4652 | 0.064* | |
C9C | 0.1805 (2) | 0.0214 (3) | 0.98579 (17) | 0.0383 (6) | |
H9C | 0.1759 | −0.0555 | 1.0217 | 0.046* | |
C10B | 0.2329 (3) | −0.4426 (3) | 1.13178 (18) | 0.0487 (7) | |
H10B | 0.1612 | −0.4683 | 1.1554 | 0.058* | |
C18C | 0.1960 (3) | −0.0974 (3) | 1.22528 (19) | 0.0463 (7) | |
H18C | 0.179 | −0.0457 | 1.2731 | 0.069* | |
H18D | 0.2164 | −0.1857 | 1.2548 | 0.069* | |
H18E | 0.1194 | −0.0708 | 1.1902 | 0.069* | |
C13B | 0.2889 (2) | −0.0925 (3) | 0.67735 (17) | 0.0370 (6) | |
H13A | 0.3188 | −0.1174 | 0.7409 | 0.044* | |
H13B | 0.2777 | −0.0026 | 0.6557 | 0.044* | |
C19C | 0.4921 (3) | 0.0965 (3) | 1.1121 (2) | 0.0490 (7) | |
H19C | 0.5416 | 0.0078 | 1.1332 | 0.073* | |
H19D | 0.5265 | 0.1491 | 1.1367 | 0.073* | |
H19E | 0.4989 | 0.1156 | 1.0441 | 0.073* | |
C9B | 0.3240 (3) | −0.4536 (3) | 1.19321 (19) | 0.0524 (8) | |
H9B | 0.3126 | −0.4844 | 1.2576 | 0.063* | |
H2N | −0.031 (3) | −0.205 (3) | 0.7090 (19) | 0.040 (8)* | |
H4N | 0.333 (3) | −0.051 (3) | 0.492 (2) | 0.058 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S2C | 0.0626 (4) | 0.0354 (3) | 0.0389 (3) | −0.0260 (3) | −0.0131 (3) | 0.0002 (3) |
S1C | 0.0356 (3) | 0.0386 (3) | 0.0308 (3) | −0.0146 (3) | −0.0094 (2) | −0.0053 (2) |
Cl1B | 0.0755 (5) | 0.0677 (5) | 0.0603 (5) | −0.0405 (4) | −0.0416 (4) | 0.0083 (4) |
O2C | 0.0271 (8) | 0.0326 (8) | 0.0335 (8) | −0.0153 (7) | −0.0096 (7) | 0.0047 (7) |
O3C | 0.0294 (8) | 0.0356 (9) | 0.0272 (8) | −0.0184 (7) | −0.0060 (6) | 0.0002 (7) |
N3C | 0.0278 (9) | 0.0326 (10) | 0.0284 (10) | −0.0071 (8) | −0.0067 (8) | −0.0070 (8) |
O1B | 0.0400 (9) | 0.0473 (10) | 0.0350 (9) | −0.0302 (8) | −0.0097 (7) | 0.0063 (8) |
N1B | 0.0326 (10) | 0.0408 (11) | 0.0281 (10) | −0.0226 (9) | −0.0060 (8) | 0.0018 (8) |
N2B | 0.0289 (10) | 0.0390 (11) | 0.0275 (10) | −0.0201 (9) | −0.0075 (8) | 0.0042 (8) |
O1C | 0.0303 (9) | 0.0609 (12) | 0.0367 (9) | −0.0226 (8) | −0.0015 (7) | −0.0138 (8) |
N3B | 0.0317 (10) | 0.0507 (12) | 0.0271 (10) | −0.0278 (9) | −0.0062 (8) | 0.0061 (9) |
C16C | 0.0305 (11) | 0.0299 (11) | 0.0251 (11) | −0.0149 (9) | −0.0044 (9) | −0.0023 (9) |
N4B | 0.0253 (9) | 0.0320 (11) | 0.0348 (11) | −0.0154 (8) | −0.0038 (8) | 0.0021 (8) |
C1B | 0.0297 (11) | 0.0364 (12) | 0.0268 (11) | −0.0182 (10) | −0.0041 (9) | −0.0008 (9) |
N2C | 0.0369 (11) | 0.0487 (12) | 0.0291 (10) | −0.0216 (10) | −0.0011 (8) | −0.0044 (9) |
C17C | 0.0223 (10) | 0.0305 (11) | 0.0210 (10) | −0.0126 (9) | 0.0005 (8) | −0.0020 (8) |
C11B | 0.0251 (11) | 0.0441 (13) | 0.0286 (11) | −0.0199 (10) | −0.0053 (9) | 0.0053 (10) |
C2C | 0.0345 (12) | 0.0263 (11) | 0.0357 (12) | −0.0040 (9) | −0.0115 (10) | −0.0071 (9) |
C12B | 0.0340 (12) | 0.0360 (12) | 0.0327 (12) | −0.0231 (10) | −0.0085 (10) | 0.0049 (10) |
C5B | 0.0433 (14) | 0.0344 (13) | 0.0338 (12) | −0.0221 (11) | −0.0149 (11) | 0.0060 (10) |
C4B | 0.0401 (13) | 0.0413 (13) | 0.0322 (12) | −0.0266 (11) | −0.0099 (10) | 0.0046 (10) |
C2B | 0.0327 (12) | 0.0366 (13) | 0.0288 (11) | −0.0189 (10) | −0.0042 (9) | −0.0006 (10) |
C6B | 0.0423 (14) | 0.0443 (14) | 0.0349 (13) | −0.0230 (12) | −0.0110 (11) | 0.0023 (11) |
C7C | 0.0312 (12) | 0.0494 (15) | 0.0293 (12) | −0.0182 (11) | 0.0010 (10) | −0.0089 (11) |
C12C | 0.0398 (13) | 0.0450 (14) | 0.0292 (12) | −0.0198 (11) | −0.0002 (10) | −0.0038 (11) |
C3B | 0.0331 (12) | 0.0374 (13) | 0.0306 (12) | −0.0215 (10) | −0.0046 (10) | −0.0013 (10) |
C10C | 0.0294 (12) | 0.0486 (15) | 0.0293 (12) | −0.0179 (11) | 0.0032 (9) | −0.0076 (11) |
C6C | 0.0292 (12) | 0.0514 (15) | 0.0328 (12) | −0.0185 (11) | 0.0000 (10) | −0.0117 (11) |
C4C | 0.0234 (11) | 0.0395 (13) | 0.0334 (12) | −0.0076 (9) | −0.0023 (9) | −0.0112 (10) |
C5C | 0.0262 (11) | 0.0417 (13) | 0.0309 (12) | −0.0104 (10) | −0.0051 (9) | −0.0088 (10) |
C14B | 0.0291 (12) | 0.0383 (13) | 0.0412 (14) | −0.0193 (10) | −0.0120 (10) | 0.0099 (11) |
C15C | 0.0337 (12) | 0.0333 (12) | 0.0302 (12) | −0.0079 (10) | −0.0119 (10) | −0.0036 (10) |
C7B | 0.0405 (14) | 0.0448 (15) | 0.0468 (15) | −0.0224 (12) | −0.0125 (12) | −0.0019 (12) |
C8C | 0.0374 (13) | 0.0539 (16) | 0.0348 (13) | −0.0257 (12) | 0.0022 (10) | −0.0124 (12) |
C8B | 0.0569 (16) | 0.0405 (14) | 0.0458 (15) | −0.0260 (13) | −0.0271 (13) | 0.0043 (12) |
C13C | 0.0409 (14) | 0.0503 (15) | 0.0269 (12) | −0.0211 (12) | −0.0042 (10) | −0.0062 (11) |
C14C | 0.0450 (15) | 0.0489 (16) | 0.0346 (13) | −0.0187 (12) | −0.0054 (11) | −0.0026 (12) |
C11C | 0.0386 (13) | 0.0473 (15) | 0.0294 (12) | −0.0222 (11) | −0.0005 (10) | −0.0100 (11) |
C15B | 0.0360 (13) | 0.0395 (14) | 0.0520 (16) | −0.0145 (11) | 0.0036 (12) | −0.0096 (12) |
C9C | 0.0394 (13) | 0.0486 (15) | 0.0322 (12) | −0.0239 (12) | 0.0017 (10) | −0.0053 (11) |
C10B | 0.0687 (19) | 0.0581 (17) | 0.0359 (14) | −0.0472 (15) | −0.0210 (13) | 0.0131 (12) |
C18C | 0.0551 (17) | 0.0534 (17) | 0.0382 (14) | −0.0308 (14) | −0.0010 (12) | −0.0046 (12) |
C13B | 0.0356 (13) | 0.0527 (15) | 0.0318 (12) | −0.0318 (12) | −0.0087 (10) | 0.0069 (11) |
C19C | 0.0394 (14) | 0.0641 (19) | 0.0490 (16) | −0.0259 (13) | −0.0047 (12) | −0.0063 (14) |
C9B | 0.080 (2) | 0.0572 (18) | 0.0363 (14) | −0.0471 (16) | −0.0266 (14) | 0.0152 (13) |
S2C—C2C | 1.643 (3) | C7C—C8C | 1.404 (4) |
S1C—C2C | 1.742 (2) | C7C—C12C | 1.411 (3) |
S1C—C5C | 1.755 (3) | C7C—C6C | 1.436 (3) |
Cl1B—C8B | 1.743 (3) | C12C—C11C | 1.374 (3) |
O2C—C17C | 1.263 (2) | C12C—H12C | 0.93 |
O3C—C17C | 1.250 (2) | C10C—C9C | 1.412 (3) |
N3C—C2C | 1.366 (3) | C10C—C11C | 1.415 (4) |
N3C—C4C | 1.407 (3) | C6C—C5C | 1.350 (3) |
N3C—C15C | 1.467 (3) | C6C—H6C | 0.93 |
O1B—C2B | 1.219 (3) | C4C—C5C | 1.462 (3) |
N1B—C1B | 1.308 (3) | C14B—C13B | 1.512 (4) |
N1B—C3B | 1.409 (3) | C14B—H14A | 0.97 |
N2B—C2B | 1.380 (3) | C14B—H14B | 0.97 |
N2B—C1B | 1.385 (3) | C15C—H25C | 0.97 |
N2B—H2N | 0.84 (3) | C15C—H25D | 0.97 |
O1C—C4C | 1.215 (3) | C7B—C8B | 1.376 (4) |
N3B—C1B | 1.355 (3) | C7B—H7B | 0.93 |
N3B—C11B | 1.463 (3) | C8C—C9C | 1.365 (3) |
N3B—C13B | 1.464 (3) | C8C—H8C | 0.93 |
C16C—C17C | 1.520 (3) | C8B—C9B | 1.376 (4) |
C16C—C15C | 1.524 (3) | C13C—C19C | 1.518 (4) |
C16C—H16C | 0.97 | C13C—H13C | 0.97 |
C16C—H16D | 0.97 | C13C—H13D | 0.97 |
N4B—C15B | 1.480 (3) | C14C—C18C | 1.514 (4) |
N4B—C14B | 1.490 (3) | C14C—H14C | 0.97 |
N4B—C12B | 1.495 (3) | C14C—H14D | 0.97 |
N4B—H4N | 0.93 (3) | C11C—H11C | 0.93 |
N2C—C10C | 1.362 (3) | C15B—H15A | 0.96 |
N2C—C13C | 1.459 (3) | C15B—H15B | 0.96 |
N2C—C14C | 1.467 (3) | C15B—H15C | 0.96 |
C11B—C12B | 1.510 (3) | C9C—H9C | 0.93 |
C11B—H11A | 0.97 | C10B—C9B | 1.384 (4) |
C11B—H11B | 0.97 | C10B—H10B | 0.93 |
C12B—H12A | 0.97 | C18C—H18C | 0.96 |
C12B—H12B | 0.97 | C18C—H18D | 0.96 |
C5B—C10B | 1.391 (3) | C18C—H18E | 0.96 |
C5B—C6B | 1.394 (3) | C13B—H13A | 0.97 |
C5B—C4B | 1.460 (3) | C13B—H13B | 0.97 |
C4B—C3B | 1.344 (3) | C19C—H19C | 0.96 |
C4B—H4B | 0.93 | C19C—H19D | 0.96 |
C2B—C3B | 1.489 (3) | C19C—H19E | 0.96 |
C6B—C7B | 1.385 (3) | C9B—H9B | 0.93 |
C6B—H6B | 0.93 | ||
C2C—S1C—C5C | 92.64 (11) | O1C—C4C—C5C | 127.5 (2) |
C2C—N3C—C4C | 116.79 (19) | N3C—C4C—C5C | 110.1 (2) |
C2C—N3C—C15C | 122.3 (2) | C6C—C5C—C4C | 121.3 (2) |
C4C—N3C—C15C | 120.71 (19) | C6C—C5C—S1C | 128.32 (18) |
C1B—N1B—C3B | 104.95 (18) | C4C—C5C—S1C | 109.90 (17) |
C2B—N2B—C1B | 107.25 (18) | N4B—C14B—C13B | 109.61 (19) |
C2B—N2B—H2N | 123.9 (19) | N4B—C14B—H14A | 109.7 |
C1B—N2B—H2N | 128.0 (19) | C13B—C14B—H14A | 109.7 |
C1B—N3B—C11B | 123.36 (18) | N4B—C14B—H14B | 109.7 |
C1B—N3B—C13B | 118.36 (18) | C13B—C14B—H14B | 109.7 |
C11B—N3B—C13B | 112.26 (17) | H14A—C14B—H14B | 108.2 |
C17C—C16C—C15C | 111.23 (18) | N3C—C15C—C16C | 112.02 (18) |
C17C—C16C—H16C | 109.4 | N3C—C15C—H25C | 109.2 |
C15C—C16C—H16C | 109.4 | C16C—C15C—H25C | 109.2 |
C17C—C16C—H16D | 109.4 | N3C—C15C—H25D | 109.2 |
C15C—C16C—H16D | 109.4 | C16C—C15C—H25D | 109.2 |
H16C—C16C—H16D | 108 | H25C—C15C—H25D | 107.9 |
C15B—N4B—C14B | 112.21 (19) | C8B—C7B—C6B | 119.1 (2) |
C15B—N4B—C12B | 111.77 (19) | C8B—C7B—H7B | 120.4 |
C14B—N4B—C12B | 110.53 (17) | C6B—C7B—H7B | 120.4 |
C15B—N4B—H4N | 103.5 (19) | C9C—C8C—C7C | 122.5 (2) |
C14B—N4B—H4N | 107.8 (19) | C9C—C8C—H8C | 118.7 |
C12B—N4B—H4N | 110.7 (19) | C7C—C8C—H8C | 118.7 |
N1B—C1B—N3B | 123.6 (2) | C9B—C8B—C7B | 121.3 (2) |
N1B—C1B—N2B | 115.14 (19) | C9B—C8B—Cl1B | 119.3 (2) |
N3B—C1B—N2B | 121.19 (19) | C7B—C8B—Cl1B | 119.3 (2) |
C10C—N2C—C13C | 121.9 (2) | N2C—C13C—C19C | 112.4 (2) |
C10C—N2C—C14C | 121.1 (2) | N2C—C13C—H13C | 109.1 |
C13C—N2C—C14C | 115.8 (2) | C19C—C13C—H13C | 109.1 |
O3C—C17C—O2C | 124.1 (2) | N2C—C13C—H13D | 109.1 |
O3C—C17C—C16C | 118.59 (18) | C19C—C13C—H13D | 109.1 |
O2C—C17C—C16C | 117.27 (18) | H13C—C13C—H13D | 107.8 |
N3B—C11B—C12B | 110.99 (19) | N2C—C14C—C18C | 113.4 (2) |
N3B—C11B—H11A | 109.4 | N2C—C14C—H14C | 108.9 |
C12B—C11B—H11A | 109.4 | C18C—C14C—H14C | 108.9 |
N3B—C11B—H11B | 109.4 | N2C—C14C—H14D | 108.9 |
C12B—C11B—H11B | 109.4 | C18C—C14C—H14D | 108.9 |
H11A—C11B—H11B | 108 | H14C—C14C—H14D | 107.7 |
N3C—C2C—S2C | 126.71 (18) | C12C—C11C—C10C | 121.7 (2) |
N3C—C2C—S1C | 110.51 (17) | C12C—C11C—H11C | 119.2 |
S2C—C2C—S1C | 122.77 (14) | C10C—C11C—H11C | 119.2 |
N4B—C12B—C11B | 109.88 (19) | N4B—C15B—H15A | 109.5 |
N4B—C12B—H12A | 109.7 | N4B—C15B—H15B | 109.5 |
C11B—C12B—H12A | 109.7 | H15A—C15B—H15B | 109.5 |
N4B—C12B—H12B | 109.7 | N4B—C15B—H15C | 109.5 |
C11B—C12B—H12B | 109.7 | H15A—C15B—H15C | 109.5 |
H12A—C12B—H12B | 108.2 | H15B—C15B—H15C | 109.5 |
C10B—C5B—C6B | 117.8 (2) | C8C—C9C—C10C | 121.2 (2) |
C10B—C5B—C4B | 118.7 (2) | C8C—C9C—H9C | 119.4 |
C6B—C5B—C4B | 123.4 (2) | C10C—C9C—H9C | 119.4 |
C3B—C4B—C5B | 128.1 (2) | C9B—C10B—C5B | 121.5 (2) |
C3B—C4B—H4B | 116 | C9B—C10B—H10B | 119.2 |
C5B—C4B—H4B | 116 | C5B—C10B—H10B | 119.2 |
O1B—C2B—N2B | 125.9 (2) | C14C—C18C—H18C | 109.5 |
O1B—C2B—C3B | 130.0 (2) | C14C—C18C—H18D | 109.5 |
N2B—C2B—C3B | 104.05 (18) | H18C—C18C—H18D | 109.5 |
C7B—C6B—C5B | 121.2 (2) | C14C—C18C—H18E | 109.5 |
C7B—C6B—H6B | 119.4 | H18C—C18C—H18E | 109.5 |
C5B—C6B—H6B | 119.4 | H18D—C18C—H18E | 109.5 |
C8C—C7C—C12C | 116.5 (2) | N3B—C13B—C14B | 110.7 (2) |
C8C—C7C—C6C | 119.2 (2) | N3B—C13B—H13A | 109.5 |
C12C—C7C—C6C | 124.4 (2) | C14B—C13B—H13A | 109.5 |
C11C—C12C—C7C | 121.4 (2) | N3B—C13B—H13B | 109.5 |
C11C—C12C—H12C | 119.3 | C14B—C13B—H13B | 109.5 |
C7C—C12C—H12C | 119.3 | H13A—C13B—H13B | 108.1 |
C4B—C3B—N1B | 128.9 (2) | C13C—C19C—H19C | 109.5 |
C4B—C3B—C2B | 122.4 (2) | C13C—C19C—H19D | 109.5 |
N1B—C3B—C2B | 108.56 (19) | H19C—C19C—H19D | 109.5 |
N2C—C10C—C9C | 121.5 (2) | C13C—C19C—H19E | 109.5 |
N2C—C10C—C11C | 122.0 (2) | H19C—C19C—H19E | 109.5 |
C9C—C10C—C11C | 116.5 (2) | H19D—C19C—H19E | 109.5 |
C5C—C6C—C7C | 130.9 (2) | C8B—C9B—C10B | 118.9 (2) |
C5C—C6C—H6C | 114.5 | C8B—C9B—H9B | 120.5 |
C7C—C6C—H6C | 114.5 | C10B—C9B—H9B | 120.5 |
O1C—C4C—N3C | 122.4 (2) | ||
C3B—N1B—C1B—N3B | 176.1 (2) | C12C—C7C—C6C—C5C | 17.1 (4) |
C3B—N1B—C1B—N2B | −1.7 (3) | C2C—N3C—C4C—O1C | −178.3 (2) |
C11B—N3B—C1B—N1B | 164.1 (2) | C15C—N3C—C4C—O1C | −3.0 (3) |
C13B—N3B—C1B—N1B | 13.6 (4) | C2C—N3C—C4C—C5C | 1.2 (3) |
C11B—N3B—C1B—N2B | −18.2 (4) | C15C—N3C—C4C—C5C | 176.57 (19) |
C13B—N3B—C1B—N2B | −168.8 (2) | C7C—C6C—C5C—C4C | 174.6 (2) |
C2B—N2B—C1B—N1B | 0.7 (3) | C7C—C6C—C5C—S1C | 2.8 (4) |
C2B—N2B—C1B—N3B | −177.2 (2) | O1C—C4C—C5C—C6C | 7.3 (4) |
C15C—C16C—C17C—O3C | 83.4 (2) | N3C—C4C—C5C—C6C | −172.2 (2) |
C15C—C16C—C17C—O2C | −95.2 (2) | O1C—C4C—C5C—S1C | −179.6 (2) |
C1B—N3B—C11B—C12B | −96.0 (3) | N3C—C4C—C5C—S1C | 0.9 (2) |
C13B—N3B—C11B—C12B | 56.2 (3) | C2C—S1C—C5C—C6C | 170.4 (2) |
C4C—N3C—C2C—S2C | 177.02 (17) | C2C—S1C—C5C—C4C | −2.07 (18) |
C15C—N3C—C2C—S2C | 1.8 (3) | C15B—N4B—C14B—C13B | 176.34 (19) |
C4C—N3C—C2C—S1C | −2.8 (2) | C12B—N4B—C14B—C13B | −58.2 (2) |
C15C—N3C—C2C—S1C | −178.06 (16) | C2C—N3C—C15C—C16C | 80.6 (3) |
C5C—S1C—C2C—N3C | 2.75 (18) | C4C—N3C—C15C—C16C | −94.5 (2) |
C5C—S1C—C2C—S2C | −177.08 (16) | C17C—C16C—C15C—N3C | 59.7 (2) |
C15B—N4B—C12B—C11B | −176.65 (19) | C5B—C6B—C7B—C8B | −1.7 (4) |
C14B—N4B—C12B—C11B | 57.6 (2) | C12C—C7C—C8C—C9C | −4.1 (4) |
N3B—C11B—C12B—N4B | −55.9 (2) | C6C—C7C—C8C—C9C | 174.1 (2) |
C10B—C5B—C4B—C3B | 167.1 (3) | C6B—C7B—C8B—C9B | 0.5 (4) |
C6B—C5B—C4B—C3B | −13.8 (4) | C6B—C7B—C8B—Cl1B | −178.7 (2) |
C1B—N2B—C2B—O1B | −179.0 (2) | C10C—N2C—C13C—C19C | −85.3 (3) |
C1B—N2B—C2B—C3B | 0.6 (3) | C14C—N2C—C13C—C19C | 82.8 (3) |
C10B—C5B—C6B—C7B | 1.3 (4) | C10C—N2C—C14C—C18C | −91.0 (3) |
C4B—C5B—C6B—C7B | −177.9 (2) | C13C—N2C—C14C—C18C | 100.8 (3) |
C8C—C7C—C12C—C11C | 3.0 (4) | C7C—C12C—C11C—C10C | 1.4 (4) |
C6C—C7C—C12C—C11C | −175.1 (2) | N2C—C10C—C11C—C12C | 175.5 (2) |
C5B—C4B—C3B—N1B | −1.1 (5) | C9C—C10C—C11C—C12C | −4.7 (4) |
C5B—C4B—C3B—C2B | −176.9 (2) | C7C—C8C—C9C—C10C | 0.8 (4) |
C1B—N1B—C3B—C4B | −174.3 (3) | N2C—C10C—C9C—C8C | −176.5 (2) |
C1B—N1B—C3B—C2B | 2.0 (3) | C11C—C10C—C9C—C8C | 3.6 (4) |
O1B—C2B—C3B—C4B | −5.4 (4) | C6B—C5B—C10B—C9B | 0.4 (4) |
N2B—C2B—C3B—C4B | 174.9 (2) | C4B—C5B—C10B—C9B | 179.6 (3) |
O1B—C2B—C3B—N1B | 178.0 (3) | C1B—N3B—C13B—C14B | 97.0 (3) |
N2B—C2B—C3B—N1B | −1.6 (3) | C11B—N3B—C13B—C14B | −56.7 (3) |
C13C—N2C—C10C—C9C | 178.2 (2) | N4B—C14B—C13B—N3B | 57.1 (2) |
C14C—N2C—C10C—C9C | 10.7 (3) | C7B—C8B—C9B—C10B | 1.1 (5) |
C13C—N2C—C10C—C11C | −2.0 (4) | Cl1B—C8B—C9B—C10B | −179.7 (2) |
C14C—N2C—C10C—C11C | −169.4 (2) | C5B—C10B—C9B—C8B | −1.5 (5) |
C8C—C7C—C6C—C5C | −160.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2B—H2N···O3Ci | 0.84 (3) | 1.95 (3) | 2.779 (3) | 169 (3) |
N4B—H4N···O2C | 0.93 (3) | 1.71 (3) | 2.642 (3) | 173 (3) |
N4B—H4N···O3C | 0.93 (3) | 2.55 (3) | 3.207 (3) | 128 (2) |
C16C—H16C···O1Bi | 0.97 | 2.63 | 3.533 (3) | 155 |
C11B—H11A···O1C | 0.97 | 2.44 | 3.364 (3) | 160 |
C11B—H11B···O3Ci | 0.97 | 2.31 | 3.261 (3) | 166 |
C12B—H12A···S2Cii | 0.97 | 2.91 | 3.718 (3) | 142 |
C14B—H14A···O2Ciii | 0.97 | 2.46 | 3.380 (3) | 159 |
C13C—H13D···O1Biv | 0.97 | 2.58 | 3.366 (3) | 139 |
C15B—H15C···S2Ciii | 0.96 | 3.02 | 3.735 (3) | 132 |
C18C—H18C···O3Cv | 0.96 | 2.49 | 3.425 (3) | 166 |
C9B—H9B···S2Cvi | 0.93 | 3.03 | 3.899 (3) | 156 |
C6B—H6B···N1B | 0.93 | 2.41 | 3.049 (3) | 125 |
C13B—H13A···N1B | 0.97 | 2.38 | 2.796 (3) | 105 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, y−1, z; (iii) −x+1, −y, −z+1; (iv) −x, −y, −z+2; (v) x, y, z+1; (vi) x, y−1, z+1. |