Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616012870/sk3634sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616012870/sk3634Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616012870/sk3634IIsup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616012870/sk3634Isup4.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616012870/sk3634IIsup5.cml |
CCDC references: 1498397; 1498396
For both compounds, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT-Plus (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).
C19H18ClN3O2 | Z = 4 |
Mr = 355.81 | F(000) = 744 |
Triclinic, P1 | Dx = 1.347 Mg m−3 |
a = 10.1018 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.6099 (5) Å | Cell parameters from 8317 reflections |
c = 18.8129 (11) Å | θ = 1.1–28.2° |
α = 100.292 (3)° | µ = 0.24 mm−1 |
β = 91.881 (3)° | T = 295 K |
γ = 116.873 (2)° | Block, colourless |
V = 1754.78 (15) Å3 | 0.30 × 0.20 × 0.20 mm |
Bruker APEXII area-detector diffractometer | 7205 independent reflections |
Radiation source: fine-focus sealed tube | 5041 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 26.6°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −12→12 |
Tmin = 0.788, Tmax = 0.954 | k = −13→13 |
32307 measured reflections | l = −23→23 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0535P)2 + 0.8541P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
7205 reflections | Δρmax = 0.58 e Å−3 |
461 parameters | Δρmin = −0.63 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 | ||
C11 | 0.0605 (2) | 0.4111 (2) | 0.35897 (11) | 0.0430 (5) | |
O11 | −0.02706 (17) | 0.35666 (18) | 0.40064 (9) | 0.0587 (4) | |
N11 | 0.19775 (19) | 0.41816 (17) | 0.36076 (9) | 0.0393 (4) | |
H11 | 0.255 (3) | 0.453 (2) | 0.3284 (12) | 0.047* | |
C12 | 0.0218 (3) | 0.4743 (2) | 0.30052 (14) | 0.0545 (6) | |
H12A | −0.0071 | 0.5466 | 0.3224 | 0.065* | |
H12B | 0.1085 | 0.5208 | 0.2760 | 0.065* | |
N111 | 0.2896 (2) | 0.27333 (18) | 0.50227 (8) | 0.0426 (4) | |
N112 | 0.33015 (19) | 0.20766 (17) | 0.44120 (8) | 0.0403 (4) | |
C113 | 0.2960 (2) | 0.2495 (2) | 0.37988 (10) | 0.0370 (4) | |
O113 | 0.30568 (19) | 0.19812 (16) | 0.31741 (7) | 0.0511 (4) | |
C114 | 0.2477 (2) | 0.35432 (19) | 0.40692 (10) | 0.0366 (4) | |
C115 | 0.2510 (2) | 0.3693 (2) | 0.48018 (11) | 0.0415 (5) | |
C116 | 0.3858 (3) | 0.3110 (3) | 0.57066 (11) | 0.0549 (6) | |
H11A | 0.4836 | 0.3865 | 0.5682 | 0.082* | |
H11B | 0.3933 | 0.2273 | 0.5784 | 0.082* | |
H11C | 0.3435 | 0.3439 | 0.6103 | 0.082* | |
C117 | 0.2218 (3) | 0.4710 (3) | 0.53415 (13) | 0.0609 (6) | |
H11D | 0.3150 | 0.5477 | 0.5600 | 0.091* | |
H11E | 0.1611 | 0.4202 | 0.5680 | 0.091* | |
H11F | 0.1703 | 0.5110 | 0.5094 | 0.091* | |
C121 | −0.1055 (2) | 0.3547 (2) | 0.24629 (12) | 0.0478 (5) | |
C122 | −0.2525 (3) | 0.3030 (3) | 0.26009 (13) | 0.0568 (6) | |
H122 | −0.2746 | 0.3487 | 0.3015 | 0.068* | |
C123 | −0.3667 (3) | 0.1853 (3) | 0.21375 (13) | 0.0623 (7) | |
H123 | −0.4650 | 0.1514 | 0.2238 | 0.075* | |
C124 | −0.3343 (3) | 0.1186 (3) | 0.15289 (13) | 0.0574 (6) | |
Cl14 | −0.47626 (10) | −0.03248 (9) | 0.09513 (4) | 0.0943 (3) | |
C125 | −0.1915 (3) | 0.1699 (3) | 0.13668 (13) | 0.0636 (7) | |
H125 | −0.1710 | 0.1255 | 0.0943 | 0.076* | |
C126 | −0.0771 (3) | 0.2878 (3) | 0.18325 (14) | 0.0594 (6) | |
H126 | 0.0204 | 0.3226 | 0.1720 | 0.071* | |
C131 | 0.3196 (2) | 0.0688 (2) | 0.43913 (11) | 0.0399 (4) | |
C132 | 0.2258 (3) | −0.0209 (2) | 0.48042 (12) | 0.0517 (5) | |
H132 | 0.1688 | 0.0088 | 0.5101 | 0.062* | |
C133 | 0.2177 (3) | −0.1559 (3) | 0.47704 (15) | 0.0657 (7) | |
H133 | 0.1571 | −0.2162 | 0.5057 | 0.079* | |
C134 | 0.2982 (3) | −0.2006 (3) | 0.43200 (16) | 0.0695 (7) | |
H134 | 0.2911 | −0.2918 | 0.4294 | 0.083* | |
C135 | 0.3892 (3) | −0.1120 (3) | 0.39061 (15) | 0.0683 (7) | |
H135 | 0.4426 | −0.1439 | 0.3594 | 0.082* | |
C136 | 0.4026 (3) | 0.0239 (3) | 0.39467 (13) | 0.0542 (6) | |
H136 | 0.4673 | 0.0851 | 0.3676 | 0.065* | |
C21 | 0.1899 (2) | 0.1687 (2) | 0.12171 (13) | 0.0476 (5) | |
O21 | 0.1859 (2) | 0.19074 (18) | 0.06084 (9) | 0.0670 (5) | |
N21 | 0.2985 (2) | 0.26017 (18) | 0.17678 (10) | 0.0444 (4) | |
H21 | 0.299 (3) | 0.242 (3) | 0.2182 (13) | 0.053* | |
C22 | 0.0736 (3) | 0.0327 (2) | 0.14195 (15) | 0.0583 (6) | |
H22A | 0.0615 | 0.0549 | 0.1929 | 0.070* | |
H22B | −0.0218 | 0.0004 | 0.1131 | 0.070* | |
N211 | 0.6348 (2) | 0.54849 (19) | 0.14139 (10) | 0.0515 (5) | |
N212 | 0.59086 (19) | 0.62246 (18) | 0.19668 (9) | 0.0443 (4) | |
C213 | 0.4620 (2) | 0.5246 (2) | 0.21926 (10) | 0.0391 (4) | |
O213 | 0.40726 (17) | 0.55872 (16) | 0.27238 (8) | 0.0527 (4) | |
C214 | 0.4214 (2) | 0.3899 (2) | 0.17045 (10) | 0.0391 (4) | |
C215 | 0.5246 (2) | 0.4090 (2) | 0.12366 (11) | 0.0458 (5) | |
C216 | 0.7181 (4) | 0.6308 (3) | 0.08971 (15) | 0.0876 (11) | |
H21A | 0.6540 | 0.6531 | 0.0613 | 0.131* | |
H21B | 0.7538 | 0.5746 | 0.0580 | 0.131* | |
H21C | 0.8016 | 0.7190 | 0.1156 | 0.131* | |
C217 | 0.5321 (3) | 0.3049 (3) | 0.06221 (14) | 0.0651 (7) | |
H21D | 0.6330 | 0.3190 | 0.0628 | 0.098* | |
H21E | 0.5010 | 0.3200 | 0.0171 | 0.098* | |
H21F | 0.4671 | 0.2079 | 0.0668 | 0.098* | |
C221 | 0.1166 (2) | −0.0881 (2) | 0.12951 (12) | 0.0450 (5) | |
C222 | 0.0882 (2) | −0.1749 (2) | 0.06067 (12) | 0.0485 (5) | |
H222 | 0.0452 | −0.1566 | 0.0219 | 0.058* | |
C223 | 0.1228 (2) | −0.2881 (2) | 0.04885 (12) | 0.0492 (5) | |
H223 | 0.1042 | −0.3452 | 0.0023 | 0.059* | |
C224 | 0.1847 (3) | −0.3156 (2) | 0.10616 (12) | 0.0468 (5) | |
Cl24 | 0.22648 (8) | −0.45950 (7) | 0.09162 (4) | 0.0675 (2) | |
C225 | 0.2144 (3) | −0.2317 (3) | 0.17520 (12) | 0.0540 (6) | |
H225 | 0.2562 | −0.2515 | 0.2138 | 0.065* | |
C226 | 0.1811 (3) | −0.1174 (2) | 0.18619 (12) | 0.0523 (6) | |
H226 | 0.2024 | −0.0591 | 0.2326 | 0.063* | |
C231 | 0.7044 (2) | 0.7494 (2) | 0.24460 (11) | 0.0444 (5) | |
C232 | 0.8319 (3) | 0.7503 (3) | 0.27219 (13) | 0.0601 (6) | |
H232 | 0.8475 | 0.6699 | 0.2587 | 0.072* | |
C233 | 0.9370 (3) | 0.8729 (4) | 0.32045 (15) | 0.0794 (9) | |
H233 | 1.0248 | 0.8756 | 0.3392 | 0.095* | |
C234 | 0.9129 (3) | 0.9896 (3) | 0.34061 (15) | 0.0795 (10) | |
H234 | 0.9834 | 1.0708 | 0.3739 | 0.095* | |
C235 | 0.7866 (4) | 0.9887 (3) | 0.31254 (16) | 0.0749 (8) | |
H235 | 0.7714 | 1.0693 | 0.3264 | 0.090* | |
C236 | 0.6803 (3) | 0.8674 (2) | 0.26328 (13) | 0.0583 (6) | |
H236 | 0.5942 | 0.8663 | 0.2433 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0410 (11) | 0.0343 (10) | 0.0495 (12) | 0.0144 (9) | 0.0053 (9) | 0.0084 (9) |
O11 | 0.0444 (9) | 0.0690 (10) | 0.0657 (10) | 0.0240 (8) | 0.0183 (8) | 0.0263 (8) |
N11 | 0.0394 (9) | 0.0358 (9) | 0.0434 (9) | 0.0155 (7) | 0.0108 (7) | 0.0151 (7) |
C12 | 0.0465 (13) | 0.0462 (12) | 0.0732 (16) | 0.0207 (11) | 0.0031 (11) | 0.0221 (11) |
N111 | 0.0517 (10) | 0.0448 (9) | 0.0316 (8) | 0.0232 (8) | 0.0060 (7) | 0.0067 (7) |
N112 | 0.0505 (10) | 0.0397 (9) | 0.0339 (8) | 0.0230 (8) | 0.0086 (7) | 0.0096 (7) |
C113 | 0.0387 (10) | 0.0339 (10) | 0.0354 (10) | 0.0130 (8) | 0.0076 (8) | 0.0104 (8) |
O113 | 0.0757 (11) | 0.0528 (9) | 0.0352 (8) | 0.0376 (8) | 0.0142 (7) | 0.0118 (6) |
C114 | 0.0363 (10) | 0.0320 (9) | 0.0371 (10) | 0.0119 (8) | 0.0060 (8) | 0.0078 (8) |
C115 | 0.0443 (11) | 0.0365 (10) | 0.0384 (11) | 0.0152 (9) | 0.0066 (9) | 0.0050 (8) |
C116 | 0.0614 (14) | 0.0546 (13) | 0.0390 (11) | 0.0204 (12) | −0.0035 (10) | 0.0077 (10) |
C117 | 0.0813 (18) | 0.0579 (14) | 0.0473 (13) | 0.0388 (14) | 0.0115 (12) | 0.0020 (11) |
C121 | 0.0488 (12) | 0.0500 (12) | 0.0521 (13) | 0.0263 (11) | 0.0080 (10) | 0.0195 (10) |
C122 | 0.0519 (14) | 0.0696 (15) | 0.0480 (13) | 0.0304 (12) | 0.0094 (11) | 0.0044 (11) |
C123 | 0.0472 (13) | 0.0791 (17) | 0.0519 (14) | 0.0234 (13) | 0.0087 (11) | 0.0099 (12) |
C124 | 0.0618 (15) | 0.0602 (14) | 0.0460 (13) | 0.0248 (12) | 0.0046 (11) | 0.0124 (11) |
Cl14 | 0.1013 (6) | 0.0752 (5) | 0.0688 (5) | 0.0169 (4) | −0.0090 (4) | −0.0033 (4) |
C125 | 0.0801 (18) | 0.0754 (17) | 0.0455 (13) | 0.0448 (15) | 0.0169 (13) | 0.0119 (12) |
C126 | 0.0518 (14) | 0.0755 (17) | 0.0633 (15) | 0.0341 (13) | 0.0235 (12) | 0.0294 (13) |
C131 | 0.0437 (11) | 0.0366 (10) | 0.0385 (10) | 0.0176 (9) | 0.0006 (8) | 0.0096 (8) |
C132 | 0.0524 (13) | 0.0483 (12) | 0.0517 (13) | 0.0192 (11) | 0.0081 (10) | 0.0161 (10) |
C133 | 0.0688 (17) | 0.0428 (13) | 0.0724 (17) | 0.0116 (12) | 0.0027 (13) | 0.0229 (12) |
C134 | 0.089 (2) | 0.0420 (13) | 0.0759 (18) | 0.0314 (14) | −0.0039 (15) | 0.0108 (13) |
C135 | 0.091 (2) | 0.0697 (17) | 0.0638 (16) | 0.0554 (16) | 0.0091 (14) | 0.0109 (13) |
C136 | 0.0644 (15) | 0.0563 (13) | 0.0541 (13) | 0.0356 (12) | 0.0143 (11) | 0.0192 (11) |
C21 | 0.0433 (12) | 0.0365 (11) | 0.0562 (14) | 0.0136 (9) | 0.0022 (10) | 0.0088 (10) |
O21 | 0.0644 (11) | 0.0591 (10) | 0.0564 (10) | 0.0123 (9) | −0.0152 (8) | 0.0126 (8) |
N21 | 0.0484 (10) | 0.0349 (9) | 0.0395 (9) | 0.0092 (8) | 0.0036 (8) | 0.0117 (7) |
C22 | 0.0435 (12) | 0.0376 (11) | 0.0855 (17) | 0.0127 (10) | 0.0146 (12) | 0.0092 (11) |
N211 | 0.0470 (10) | 0.0460 (10) | 0.0429 (10) | 0.0079 (8) | 0.0151 (8) | 0.0025 (8) |
N212 | 0.0386 (9) | 0.0396 (9) | 0.0375 (9) | 0.0049 (7) | 0.0092 (7) | 0.0033 (7) |
C213 | 0.0380 (11) | 0.0379 (10) | 0.0354 (10) | 0.0116 (9) | 0.0054 (8) | 0.0104 (8) |
O213 | 0.0491 (9) | 0.0472 (8) | 0.0456 (8) | 0.0094 (7) | 0.0168 (7) | 0.0055 (7) |
C214 | 0.0398 (11) | 0.0362 (10) | 0.0361 (10) | 0.0127 (9) | 0.0027 (8) | 0.0104 (8) |
C215 | 0.0469 (12) | 0.0441 (11) | 0.0394 (11) | 0.0168 (10) | 0.0038 (9) | 0.0050 (9) |
C216 | 0.086 (2) | 0.0715 (18) | 0.0609 (16) | −0.0004 (16) | 0.0385 (15) | 0.0074 (14) |
C217 | 0.0706 (17) | 0.0587 (15) | 0.0564 (15) | 0.0265 (13) | 0.0134 (12) | −0.0007 (12) |
C221 | 0.0347 (10) | 0.0320 (10) | 0.0564 (13) | 0.0050 (8) | 0.0115 (9) | 0.0096 (9) |
C222 | 0.0465 (12) | 0.0457 (12) | 0.0472 (12) | 0.0155 (10) | 0.0029 (9) | 0.0131 (10) |
C223 | 0.0520 (13) | 0.0463 (12) | 0.0408 (11) | 0.0178 (10) | 0.0053 (10) | 0.0037 (9) |
C224 | 0.0511 (13) | 0.0412 (11) | 0.0464 (12) | 0.0192 (10) | 0.0087 (10) | 0.0115 (9) |
Cl24 | 0.0870 (5) | 0.0629 (4) | 0.0687 (4) | 0.0460 (4) | 0.0189 (3) | 0.0202 (3) |
C225 | 0.0606 (14) | 0.0558 (14) | 0.0426 (12) | 0.0232 (12) | 0.0056 (10) | 0.0148 (10) |
C226 | 0.0554 (13) | 0.0452 (12) | 0.0440 (12) | 0.0151 (11) | 0.0084 (10) | 0.0034 (9) |
C231 | 0.0395 (11) | 0.0389 (11) | 0.0371 (10) | 0.0030 (9) | 0.0103 (9) | 0.0079 (8) |
C232 | 0.0476 (14) | 0.0649 (15) | 0.0559 (14) | 0.0200 (12) | 0.0045 (11) | 0.0023 (12) |
C233 | 0.0410 (14) | 0.100 (2) | 0.0605 (16) | 0.0094 (15) | 0.0014 (12) | −0.0040 (16) |
C234 | 0.0570 (17) | 0.0640 (18) | 0.0588 (16) | −0.0143 (14) | 0.0115 (13) | −0.0083 (13) |
C235 | 0.087 (2) | 0.0383 (13) | 0.0740 (18) | 0.0097 (14) | 0.0189 (16) | 0.0042 (12) |
C236 | 0.0616 (15) | 0.0444 (13) | 0.0578 (14) | 0.0148 (11) | 0.0101 (11) | 0.0122 (11) |
C11—O11 | 1.215 (2) | C21—O21 | 1.212 (3) |
C11—N11 | 1.353 (3) | C21—N21 | 1.350 (3) |
C11—C12 | 1.511 (3) | C21—C22 | 1.517 (3) |
N11—C114 | 1.399 (3) | N21—C214 | 1.405 (2) |
N11—H11 | 0.87 (2) | N21—H21 | 0.83 (2) |
C12—C121 | 1.510 (3) | C22—C221 | 1.512 (3) |
C12—H12A | 0.9700 | C22—H22A | 0.9700 |
C12—H12B | 0.9700 | C22—H22B | 0.9700 |
N111—C115 | 1.364 (3) | N211—C215 | 1.360 (3) |
N111—N112 | 1.406 (2) | N211—N212 | 1.396 (2) |
N111—C116 | 1.463 (3) | N211—C216 | 1.452 (3) |
N112—C113 | 1.394 (2) | N212—C213 | 1.387 (2) |
N112—C131 | 1.422 (3) | N212—C231 | 1.430 (2) |
C113—O113 | 1.231 (2) | C213—O213 | 1.235 (2) |
C113—C114 | 1.428 (3) | C213—C214 | 1.425 (3) |
C114—C115 | 1.356 (3) | C214—C215 | 1.355 (3) |
C115—C117 | 1.483 (3) | C215—C217 | 1.479 (3) |
C116—H11A | 0.9600 | C216—H21A | 0.9600 |
C116—H11B | 0.9600 | C216—H21B | 0.9600 |
C116—H11C | 0.9600 | C216—H21C | 0.9600 |
C117—H11D | 0.9600 | C217—H21D | 0.9600 |
C117—H11E | 0.9600 | C217—H21E | 0.9600 |
C117—H11F | 0.9600 | C217—H21F | 0.9600 |
C121—C126 | 1.378 (3) | C221—C226 | 1.383 (3) |
C121—C122 | 1.383 (3) | C221—C222 | 1.385 (3) |
C122—C123 | 1.376 (3) | C222—C223 | 1.380 (3) |
C122—H122 | 0.9300 | C222—H222 | 0.9300 |
C123—C124 | 1.365 (3) | C223—C224 | 1.368 (3) |
C123—H123 | 0.9300 | C223—H223 | 0.9300 |
C124—C125 | 1.360 (4) | C224—C225 | 1.374 (3) |
C124—Cl14 | 1.733 (3) | C224—Cl24 | 1.740 (2) |
C125—C126 | 1.380 (4) | C225—C226 | 1.382 (3) |
C125—H125 | 0.9300 | C225—H225 | 0.9300 |
C126—H126 | 0.9300 | C226—H226 | 0.9300 |
C131—C136 | 1.376 (3) | C231—C232 | 1.368 (3) |
C131—C132 | 1.380 (3) | C231—C236 | 1.369 (3) |
C132—C133 | 1.387 (3) | C232—C233 | 1.382 (4) |
C132—H132 | 0.9300 | C232—H232 | 0.9300 |
C133—C134 | 1.361 (4) | C233—C234 | 1.359 (5) |
C133—H133 | 0.9300 | C233—H233 | 0.9300 |
C134—C135 | 1.365 (4) | C234—C235 | 1.361 (5) |
C134—H134 | 0.9300 | C234—H234 | 0.9300 |
C135—C136 | 1.373 (3) | C235—C236 | 1.388 (4) |
C135—H135 | 0.9300 | C235—H235 | 0.9300 |
C136—H136 | 0.9300 | C236—H236 | 0.9300 |
O11—C11—N11 | 122.9 (2) | O21—C21—N21 | 123.5 (2) |
O11—C11—C12 | 121.8 (2) | O21—C21—C22 | 122.3 (2) |
N11—C11—C12 | 115.31 (18) | N21—C21—C22 | 114.1 (2) |
C11—N11—C114 | 123.23 (17) | C21—N21—C214 | 124.54 (18) |
C11—N11—H11 | 120.1 (15) | C21—N21—H21 | 121.6 (16) |
C114—N11—H11 | 116.2 (15) | C214—N21—H21 | 113.9 (16) |
C121—C12—C11 | 109.27 (17) | C221—C22—C21 | 112.18 (18) |
C121—C12—H12A | 109.8 | C221—C22—H22A | 109.2 |
C11—C12—H12A | 109.8 | C21—C22—H22A | 109.2 |
C121—C12—H12B | 109.8 | C221—C22—H22B | 109.2 |
C11—C12—H12B | 109.8 | C21—C22—H22B | 109.2 |
H12A—C12—H12B | 108.3 | H22A—C22—H22B | 107.9 |
C115—N111—N112 | 106.81 (15) | C215—N211—N212 | 107.21 (16) |
C115—N111—C116 | 121.99 (17) | C215—N211—C216 | 125.02 (19) |
N112—N111—C116 | 114.89 (18) | N212—N211—C216 | 116.1 (2) |
C113—N112—N111 | 108.88 (16) | C213—N212—N211 | 109.36 (15) |
C113—N112—C131 | 123.24 (16) | C213—N212—C231 | 123.33 (16) |
N111—N112—C131 | 118.59 (15) | N211—N212—C231 | 118.30 (16) |
O113—C113—N112 | 123.48 (18) | O213—C213—N212 | 122.90 (18) |
O113—C113—C114 | 131.26 (18) | O213—C213—C214 | 132.45 (18) |
N112—C113—C114 | 105.24 (16) | N212—C213—C214 | 104.62 (17) |
C115—C114—N11 | 129.18 (19) | C215—C214—N21 | 128.16 (19) |
C115—C114—C113 | 108.43 (18) | C215—C214—C213 | 109.06 (17) |
N11—C114—C113 | 122.26 (17) | N21—C214—C213 | 122.61 (18) |
C114—C115—N111 | 110.00 (17) | C214—C215—N211 | 109.27 (18) |
C114—C115—C117 | 129.6 (2) | C214—C215—C217 | 130.3 (2) |
N111—C115—C117 | 120.36 (19) | N211—C215—C217 | 120.4 (2) |
N111—C116—H11A | 109.5 | N211—C216—H21A | 109.5 |
N111—C116—H11B | 109.5 | N211—C216—H21B | 109.5 |
H11A—C116—H11B | 109.5 | H21A—C216—H21B | 109.5 |
N111—C116—H11C | 109.5 | N211—C216—H21C | 109.5 |
H11A—C116—H11C | 109.5 | H21A—C216—H21C | 109.5 |
H11B—C116—H11C | 109.5 | H21B—C216—H21C | 109.5 |
C115—C117—H11D | 109.5 | C215—C217—H21D | 109.5 |
C115—C117—H11E | 109.5 | C215—C217—H21E | 109.5 |
H11D—C117—H11E | 109.5 | H21D—C217—H21E | 109.5 |
C115—C117—H11F | 109.5 | C215—C217—H21F | 109.5 |
H11D—C117—H11F | 109.5 | H21D—C217—H21F | 109.5 |
H11E—C117—H11F | 109.5 | H21E—C217—H21F | 109.5 |
C126—C121—C122 | 118.0 (2) | C226—C221—C222 | 118.4 (2) |
C126—C121—C12 | 120.4 (2) | C226—C221—C22 | 121.4 (2) |
C122—C121—C12 | 121.5 (2) | C222—C221—C22 | 120.2 (2) |
C123—C122—C121 | 121.3 (2) | C223—C222—C221 | 120.9 (2) |
C123—C122—H122 | 119.4 | C223—C222—H222 | 119.5 |
C121—C122—H122 | 119.4 | C221—C222—H222 | 119.5 |
C124—C123—C122 | 119.3 (2) | C224—C223—C222 | 119.4 (2) |
C124—C123—H123 | 120.3 | C224—C223—H223 | 120.3 |
C122—C123—H123 | 120.3 | C222—C223—H223 | 120.3 |
C125—C124—C123 | 120.7 (2) | C223—C224—C225 | 121.3 (2) |
C125—C124—Cl14 | 119.4 (2) | C223—C224—Cl24 | 119.50 (17) |
C123—C124—Cl14 | 119.9 (2) | C225—C224—Cl24 | 119.24 (18) |
C124—C125—C126 | 119.9 (2) | C224—C225—C226 | 118.8 (2) |
C124—C125—H125 | 120.1 | C224—C225—H225 | 120.6 |
C126—C125—H125 | 120.1 | C226—C225—H225 | 120.6 |
C121—C126—C125 | 120.8 (2) | C225—C226—C221 | 121.3 (2) |
C121—C126—H126 | 119.6 | C225—C226—H226 | 119.4 |
C125—C126—H126 | 119.6 | C221—C226—H226 | 119.4 |
C136—C131—C132 | 120.3 (2) | C232—C231—C236 | 121.3 (2) |
C136—C131—N112 | 119.24 (18) | C232—C231—N212 | 120.3 (2) |
C132—C131—N112 | 120.46 (19) | C236—C231—N212 | 118.4 (2) |
C131—C132—C133 | 119.1 (2) | C231—C232—C233 | 118.8 (3) |
C131—C132—H132 | 120.5 | C231—C232—H232 | 120.6 |
C133—C132—H132 | 120.5 | C233—C232—H232 | 120.6 |
C134—C133—C132 | 120.3 (2) | C234—C233—C232 | 120.4 (3) |
C134—C133—H133 | 119.9 | C234—C233—H233 | 119.8 |
C132—C133—H133 | 119.9 | C232—C233—H233 | 119.8 |
C133—C134—C135 | 120.3 (2) | C233—C234—C235 | 120.6 (2) |
C133—C134—H134 | 119.9 | C233—C234—H234 | 119.7 |
C135—C134—H134 | 119.9 | C235—C234—H234 | 119.7 |
C134—C135—C136 | 120.5 (3) | C234—C235—C236 | 120.0 (3) |
C134—C135—H135 | 119.7 | C234—C235—H235 | 120.0 |
C136—C135—H135 | 119.7 | C236—C235—H235 | 120.0 |
C135—C136—C131 | 119.5 (2) | C231—C236—C235 | 118.8 (3) |
C135—C136—H136 | 120.2 | C231—C236—H236 | 120.6 |
C131—C136—H136 | 120.2 | C235—C236—H236 | 120.6 |
O11—C11—N11—C114 | 4.9 (3) | O21—C21—N21—C214 | −1.4 (4) |
C12—C11—N11—C114 | −174.36 (18) | C22—C21—N21—C214 | 177.29 (19) |
O11—C11—C12—C121 | −65.0 (3) | O21—C21—C22—C221 | 89.4 (3) |
N11—C11—C12—C121 | 114.3 (2) | N21—C21—C22—C221 | −89.3 (3) |
C115—N111—N112—C113 | −8.2 (2) | C215—N211—N212—C213 | 7.2 (2) |
C116—N111—N112—C113 | −146.82 (17) | C216—N211—N212—C213 | 152.4 (2) |
C115—N111—N112—C131 | −155.98 (17) | C215—N211—N212—C231 | 155.52 (19) |
C116—N111—N112—C131 | 65.4 (2) | C216—N211—N212—C231 | −59.3 (3) |
N111—N112—C113—O113 | −172.76 (18) | N211—N212—C213—O213 | 172.7 (2) |
C131—N112—C113—O113 | −26.8 (3) | C231—N212—C213—O213 | 26.3 (3) |
N111—N112—C113—C114 | 5.8 (2) | N211—N212—C213—C214 | −5.5 (2) |
C131—N112—C113—C114 | 151.75 (18) | C231—N212—C213—C214 | −151.9 (2) |
C11—N11—C114—C115 | −53.2 (3) | C21—N21—C214—C215 | −56.2 (3) |
C11—N11—C114—C113 | 122.2 (2) | C21—N21—C214—C213 | 129.1 (2) |
O113—C113—C114—C115 | 177.1 (2) | O213—C213—C214—C215 | −176.1 (2) |
N112—C113—C114—C115 | −1.3 (2) | N212—C213—C214—C215 | 1.8 (2) |
O113—C113—C114—N11 | 0.9 (3) | O213—C213—C214—N21 | −0.5 (4) |
N112—C113—C114—N11 | −177.47 (16) | N212—C213—C214—N21 | 177.38 (18) |
N11—C114—C115—N111 | 171.97 (18) | N21—C214—C215—N211 | −172.6 (2) |
C113—C114—C115—N111 | −3.9 (2) | C213—C214—C215—N211 | 2.6 (3) |
N11—C114—C115—C117 | −8.9 (4) | N21—C214—C215—C217 | 6.2 (4) |
C113—C114—C115—C117 | 175.3 (2) | C213—C214—C215—C217 | −178.5 (2) |
N112—N111—C115—C114 | 7.4 (2) | N212—N211—C215—C214 | −6.0 (2) |
C116—N111—C115—C114 | 142.4 (2) | C216—N211—C215—C214 | −147.2 (3) |
N112—N111—C115—C117 | −171.84 (19) | N212—N211—C215—C217 | 175.0 (2) |
C116—N111—C115—C117 | −36.8 (3) | C216—N211—C215—C217 | 33.8 (4) |
C11—C12—C121—C126 | −95.2 (3) | C21—C22—C221—C226 | 99.2 (3) |
C11—C12—C121—C122 | 80.8 (3) | C21—C22—C221—C222 | −82.5 (3) |
C126—C121—C122—C123 | 2.2 (4) | C226—C221—C222—C223 | 0.2 (3) |
C12—C121—C122—C123 | −173.9 (2) | C22—C221—C222—C223 | −178.14 (19) |
C121—C122—C123—C124 | −0.2 (4) | C221—C222—C223—C224 | 0.6 (3) |
C122—C123—C124—C125 | −1.9 (4) | C222—C223—C224—C225 | −0.6 (3) |
C122—C123—C124—Cl14 | 178.4 (2) | C222—C223—C224—Cl24 | 179.27 (17) |
C123—C124—C125—C126 | 2.0 (4) | C223—C224—C225—C226 | −0.2 (3) |
Cl14—C124—C125—C126 | −178.3 (2) | Cl24—C224—C225—C226 | 179.87 (17) |
C122—C121—C126—C125 | −2.1 (4) | C224—C225—C226—C221 | 1.1 (3) |
C12—C121—C126—C125 | 174.0 (2) | C222—C221—C226—C225 | −1.1 (3) |
C124—C125—C126—C121 | 0.0 (4) | C22—C221—C226—C225 | 177.2 (2) |
C113—N112—C131—C136 | 58.8 (3) | C213—N212—C231—C232 | 99.7 (3) |
N111—N112—C131—C136 | −158.29 (19) | N211—N212—C231—C232 | −43.9 (3) |
C113—N112—C131—C132 | −120.3 (2) | C213—N212—C231—C236 | −78.7 (3) |
N111—N112—C131—C132 | 22.6 (3) | N211—N212—C231—C236 | 137.7 (2) |
C136—C131—C132—C133 | 0.7 (3) | C236—C231—C232—C233 | 0.7 (3) |
N112—C131—C132—C133 | 179.8 (2) | N212—C231—C232—C233 | −177.7 (2) |
C131—C132—C133—C134 | −1.8 (4) | C231—C232—C233—C234 | 0.7 (4) |
C132—C133—C134—C135 | 1.0 (4) | C232—C233—C234—C235 | −1.3 (4) |
C133—C134—C135—C136 | 1.0 (4) | C233—C234—C235—C236 | 0.5 (4) |
C134—C135—C136—C131 | −2.1 (4) | C232—C231—C236—C235 | −1.5 (3) |
C132—C131—C136—C135 | 1.2 (3) | N212—C231—C236—C235 | 176.9 (2) |
N112—C131—C136—C135 | −177.9 (2) | C234—C235—C236—C231 | 0.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O213 | 0.87 (3) | 1.93 (2) | 2.781 (2) | 169 (2) |
N21—H21···O113 | 0.84 (2) | 2.01 (2) | 2.845 (2) | 178 (4) |
C133—H133···O11i | 0.93 | 2.52 | 3.446 (3) | 171 |
Symmetry code: (i) −x, −y, −z+1. |
C19H18ClN3O2 | F(000) = 1488 |
Mr = 355.81 | Dx = 1.336 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 23.023 (3) Å | Cell parameters from 6192 reflections |
b = 8.2976 (10) Å | θ = 2.1–32.2° |
c = 21.602 (3) Å | µ = 0.23 mm−1 |
β = 120.957 (14)° | T = 295 K |
V = 3538.9 (9) Å3 | Block, colourless |
Z = 8 | 0.40 × 0.30 × 0.20 mm |
Bruker APEXII area-detector diffractometer | 4079 independent reflections |
Radiation source: fine-focus sealed tube | 3038 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 27.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −29→29 |
Tmin = 0.767, Tmax = 0.954 | k = −8→10 |
33715 measured reflections | l = −28→28 |
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) + (0.0639P)2 + 3.3163P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.149 | (Δ/σ)max = 0.007 |
S = 1.03 | Δρmax = 0.30 e Å−3 |
4079 reflections | Δρmin = −0.41 e Å−3 |
319 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
64 restraints | Extinction coefficient: 0.0042 (5) |
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 | Occ. (<1) | |
C11 | 0.5797 (2) | 0.6114 (5) | 0.3652 (2) | 0.0430 (10) | 0.6020 (18) |
O11 | 0.6397 (10) | 0.563 (3) | 0.404 (2) | 0.093 (3) | 0.6020 (18) |
N11 | 0.5674 (5) | 0.7661 (13) | 0.3420 (9) | 0.0447 (8) | 0.6020 (18) |
H11 | 0.532 (3) | 0.811 (7) | 0.332 (3) | 0.054* | 0.6020 (18) |
C12 | 0.51822 (15) | 0.5266 (4) | 0.3591 (2) | 0.0521 (7) | 0.6020 (18) |
H12A | 0.4917 | 0.6049 | 0.3675 | 0.063* | 0.6020 (18) |
H12B | 0.4902 | 0.4862 | 0.3103 | 0.063* | 0.6020 (18) |
N111 | 0.7060 (7) | 1.016 (3) | 0.3680 (6) | 0.0452 (7) | 0.6020 (18) |
N112 | 0.6676 (5) | 1.0041 (18) | 0.2923 (6) | 0.0418 (9) | 0.6020 (18) |
C113 | 0.6138 (4) | 0.8990 (11) | 0.2722 (5) | 0.0327 (15) | 0.6020 (18) |
O113 | 0.5739 (5) | 0.8552 (12) | 0.2095 (5) | 0.0432 (15) | 0.6020 (18) |
C114 | 0.6156 (6) | 0.8630 (13) | 0.3379 (5) | 0.0365 (13) | 0.6020 (18) |
C115 | 0.6693 (13) | 0.939 (5) | 0.3931 (5) | 0.0435 (6) | 0.6020 (18) |
C116 | 0.734 (2) | 1.177 (4) | 0.3956 (12) | 0.0678 (8) | 0.6020 (18) |
H11A | 0.7651 | 1.1711 | 0.4467 | 0.102* | 0.6020 (18) |
H11B | 0.6974 | 1.2492 | 0.3863 | 0.102* | 0.6020 (18) |
H11C | 0.7566 | 1.2161 | 0.3720 | 0.102* | 0.6020 (18) |
C117 | 0.6917 (11) | 0.943 (3) | 0.4710 (5) | 0.0647 (10) | 0.6020 (18) |
H11D | 0.6630 | 0.8747 | 0.4797 | 0.097* | 0.6020 (18) |
H11E | 0.6889 | 1.0517 | 0.4848 | 0.097* | 0.6020 (18) |
H11F | 0.7377 | 0.9062 | 0.4990 | 0.097* | 0.6020 (18) |
C121 | 0.5354 (3) | 0.3900 (4) | 0.41070 (17) | 0.0420 (10) | 0.6020 (18) |
C122 | 0.5669 (4) | 0.4185 (6) | 0.4834 (2) | 0.0549 (11) | 0.6020 (18) |
C123 | 0.5817 (8) | 0.2935 (9) | 0.5341 (3) | 0.0690 (13) | 0.6020 (18) |
H123 | 0.6027 | 0.3151 | 0.5832 | 0.083* | 0.6020 (18) |
C124 | 0.5641 (15) | 0.1393 (9) | 0.5081 (4) | 0.0723 (14) | 0.6020 (18) |
H124 | 0.5723 | 0.0553 | 0.5401 | 0.087* | 0.6020 (18) |
C125 | 0.5348 (10) | 0.1072 (6) | 0.4367 (4) | 0.0722 (13) | 0.6020 (18) |
H125 | 0.5256 | 0.0011 | 0.4205 | 0.087* | 0.6020 (18) |
C126 | 0.5187 (4) | 0.2301 (5) | 0.3883 (3) | 0.0604 (11) | 0.6020 (18) |
H126 | 0.4961 | 0.2066 | 0.3392 | 0.073* | 0.6020 (18) |
C131 | 0.7008 (5) | 1.034 (3) | 0.2530 (7) | 0.0450 (5) | 0.6020 (18) |
C132 | 0.7707 (5) | 1.0201 (12) | 0.2868 (6) | 0.0567 (18) | 0.6020 (18) |
H132 | 0.7963 | 0.9930 | 0.3355 | 0.068* | 0.6020 (18) |
C133 | 0.8017 (6) | 1.047 (2) | 0.2473 (9) | 0.077 (3) | 0.6020 (18) |
H133 | 0.8481 | 1.0310 | 0.2688 | 0.092* | 0.6020 (18) |
C134 | 0.7653 (8) | 1.0974 (18) | 0.1777 (8) | 0.076 (2) | 0.6020 (18) |
H134 | 0.7866 | 1.1159 | 0.1516 | 0.091* | 0.6020 (18) |
C135 | 0.6974 (9) | 1.120 (4) | 0.1464 (7) | 0.075 (3) | 0.6020 (18) |
H135 | 0.6730 | 1.1608 | 0.0997 | 0.091* | 0.6020 (18) |
C136 | 0.6634 (8) | 1.084 (4) | 0.1829 (8) | 0.0616 (14) | 0.6020 (18) |
H136 | 0.6166 | 1.0947 | 0.1601 | 0.074* | 0.6020 (18) |
Cl12 | 0.59006 (6) | 0.6106 (2) | 0.51896 (6) | 0.0847 (4) | 0.6020 (18) |
C21 | 0.5859 (3) | 0.6482 (9) | 0.3872 (4) | 0.0430 (10) | 0.3980 (18) |
O21 | 0.6348 (15) | 0.564 (4) | 0.395 (4) | 0.093 (3) | 0.3980 (18) |
N21 | 0.5662 (7) | 0.779 (2) | 0.3433 (13) | 0.0447 (8) | 0.3980 (18) |
H21 | 0.520 (4) | 0.793 (11) | 0.317 (4) | 0.054* | 0.3980 (18) |
C22 | 0.5300 (2) | 0.5857 (6) | 0.3992 (3) | 0.0521 (7) | 0.3980 (18) |
H22A | 0.5240 | 0.6613 | 0.4297 | 0.063* | 0.3980 (18) |
H22B | 0.4878 | 0.5817 | 0.3531 | 0.063* | 0.3980 (18) |
N211 | 0.7063 (11) | 1.023 (4) | 0.3698 (9) | 0.0452 (7) | 0.3980 (18) |
N212 | 0.6664 (8) | 1.018 (3) | 0.2941 (8) | 0.0418 (9) | 0.3980 (18) |
C213 | 0.6083 (7) | 0.928 (2) | 0.2732 (7) | 0.0327 (15) | 0.3980 (18) |
O213 | 0.5674 (8) | 0.887 (2) | 0.2103 (8) | 0.0432 (15) | 0.3980 (18) |
C214 | 0.6123 (10) | 0.884 (2) | 0.3393 (8) | 0.0365 (13) | 0.3980 (18) |
C215 | 0.6706 (19) | 0.943 (7) | 0.3952 (8) | 0.0435 (6) | 0.3980 (18) |
C216 | 0.736 (3) | 1.181 (6) | 0.3999 (18) | 0.0678 (8) | 0.3980 (18) |
H21A | 0.7561 | 1.2248 | 0.3745 | 0.102* | 0.3980 (18) |
H21B | 0.7694 | 1.1699 | 0.4501 | 0.102* | 0.3980 (18) |
H21C | 0.7006 | 1.2526 | 0.3949 | 0.102* | 0.3980 (18) |
C217 | 0.6953 (16) | 0.939 (5) | 0.4738 (8) | 0.0647 (10) | 0.3980 (18) |
H21D | 0.6740 | 1.0236 | 0.4853 | 0.097* | 0.3980 (18) |
H21E | 0.7435 | 0.9541 | 0.5007 | 0.097* | 0.3980 (18) |
H21F | 0.6844 | 0.8367 | 0.4861 | 0.097* | 0.3980 (18) |
C221 | 0.5440 (5) | 0.4227 (7) | 0.4331 (4) | 0.0420 (10) | 0.3980 (18) |
C222 | 0.5713 (7) | 0.4054 (11) | 0.5057 (4) | 0.0549 (11) | 0.3980 (18) |
H222 | 0.5848 | 0.4970 | 0.5346 | 0.066* | 0.3980 (18) |
C223 | 0.5797 (14) | 0.2525 (14) | 0.5387 (5) | 0.0690 (13) | 0.3980 (18) |
H223 | 0.5995 | 0.2424 | 0.5884 | 0.083* | 0.3980 (18) |
C224 | 0.558 (2) | 0.1199 (13) | 0.4944 (7) | 0.0723 (14) | 0.3980 (18) |
H224 | 0.5629 | 0.0180 | 0.5146 | 0.087* | 0.3980 (18) |
C225 | 0.5279 (16) | 0.1345 (10) | 0.4219 (7) | 0.0722 (13) | 0.3980 (18) |
H225 | 0.5089 | 0.0448 | 0.3923 | 0.087* | 0.3980 (18) |
C226 | 0.5260 (8) | 0.2811 (9) | 0.3921 (4) | 0.0604 (11) | 0.3980 (18) |
C231 | 0.6996 (7) | 1.036 (5) | 0.2540 (10) | 0.0450 (5) | 0.3980 (18) |
C232 | 0.7656 (8) | 0.982 (2) | 0.2826 (10) | 0.0567 (18) | 0.3980 (18) |
H232 | 0.7876 | 0.9274 | 0.3265 | 0.068* | 0.3980 (18) |
C233 | 0.7983 (10) | 1.010 (4) | 0.2448 (14) | 0.077 (3) | 0.3980 (18) |
H233 | 0.8447 | 0.9931 | 0.2671 | 0.092* | 0.3980 (18) |
C234 | 0.7630 (13) | 1.062 (3) | 0.1754 (13) | 0.076 (2) | 0.3980 (18) |
H234 | 0.7846 | 1.0769 | 0.1494 | 0.091* | 0.3980 (18) |
C235 | 0.6956 (13) | 1.093 (6) | 0.1443 (11) | 0.075 (3) | 0.3980 (18) |
H235 | 0.6702 | 1.1153 | 0.0951 | 0.091* | 0.3980 (18) |
C236 | 0.6638 (11) | 1.093 (7) | 0.1849 (12) | 0.0616 (14) | 0.3980 (18) |
H236 | 0.6197 | 1.1306 | 0.1654 | 0.074* | 0.3980 (18) |
Cl26 | 0.4895 (2) | 0.2868 (4) | 0.2999 (2) | 0.1328 (11) | 0.3980 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0348 (12) | 0.049 (2) | 0.050 (3) | −0.0007 (12) | 0.0253 (18) | 0.0039 (16) |
O11 | 0.043 (2) | 0.0891 (13) | 0.151 (9) | 0.0239 (15) | 0.053 (5) | 0.066 (2) |
N11 | 0.0298 (7) | 0.0521 (17) | 0.0548 (10) | 0.0040 (8) | 0.0236 (7) | 0.0137 (14) |
C12 | 0.0339 (12) | 0.060 (2) | 0.0599 (19) | −0.0029 (12) | 0.0222 (15) | 0.0149 (14) |
N111 | 0.0397 (7) | 0.0557 (18) | 0.0398 (9) | −0.0131 (8) | 0.0201 (7) | −0.0099 (8) |
N112 | 0.0371 (7) | 0.051 (2) | 0.0396 (9) | −0.0126 (10) | 0.0211 (6) | −0.0059 (10) |
C113 | 0.0284 (15) | 0.029 (4) | 0.0435 (9) | 0.003 (2) | 0.0202 (9) | −0.0015 (16) |
O113 | 0.0343 (18) | 0.052 (4) | 0.0404 (7) | −0.007 (2) | 0.0170 (9) | −0.0066 (18) |
C114 | 0.0312 (12) | 0.038 (3) | 0.0442 (9) | 0.0035 (18) | 0.0222 (8) | 0.0033 (13) |
C115 | 0.0362 (11) | 0.0553 (19) | 0.0418 (10) | 0.0001 (8) | 0.0221 (10) | −0.0007 (12) |
C116 | 0.066 (2) | 0.070 (2) | 0.067 (3) | −0.0303 (13) | 0.033 (3) | −0.0273 (16) |
C117 | 0.050 (2) | 0.1021 (19) | 0.0416 (12) | −0.003 (2) | 0.0234 (13) | −0.0033 (14) |
C121 | 0.0298 (16) | 0.051 (2) | 0.042 (2) | −0.0077 (15) | 0.017 (2) | 0.0010 (18) |
C122 | 0.0437 (16) | 0.0665 (17) | 0.054 (3) | −0.0084 (13) | 0.025 (3) | 0.004 (2) |
C123 | 0.0453 (15) | 0.098 (4) | 0.0595 (15) | −0.005 (4) | 0.0238 (14) | 0.0260 (19) |
C124 | 0.051 (5) | 0.068 (2) | 0.086 (3) | 0.000 (3) | 0.027 (6) | 0.029 (2) |
C125 | 0.069 (4) | 0.047 (2) | 0.092 (4) | 0.009 (4) | 0.036 (5) | 0.014 (2) |
C126 | 0.053 (2) | 0.066 (3) | 0.0685 (16) | −0.011 (3) | 0.0349 (15) | 0.004 (2) |
C131 | 0.0470 (9) | 0.0461 (11) | 0.0512 (10) | −0.0155 (8) | 0.0320 (8) | −0.0093 (8) |
C132 | 0.0483 (17) | 0.055 (5) | 0.0749 (18) | −0.014 (3) | 0.0372 (15) | −0.005 (3) |
C133 | 0.0643 (18) | 0.082 (9) | 0.111 (2) | −0.022 (3) | 0.0634 (19) | −0.019 (4) |
C134 | 0.105 (2) | 0.066 (7) | 0.102 (2) | −0.050 (4) | 0.086 (2) | −0.041 (3) |
C135 | 0.101 (2) | 0.087 (9) | 0.0580 (14) | −0.037 (3) | 0.0546 (15) | −0.018 (3) |
C136 | 0.0594 (12) | 0.083 (4) | 0.0477 (12) | −0.0184 (13) | 0.0316 (10) | −0.0078 (18) |
Cl12 | 0.0808 (7) | 0.0924 (8) | 0.0814 (7) | −0.0292 (6) | 0.0420 (6) | −0.0263 (6) |
C21 | 0.0348 (12) | 0.049 (2) | 0.050 (3) | −0.0007 (12) | 0.0253 (18) | 0.0039 (16) |
O21 | 0.043 (2) | 0.0891 (13) | 0.151 (9) | 0.0239 (15) | 0.053 (5) | 0.066 (2) |
N21 | 0.0298 (7) | 0.0521 (17) | 0.0548 (10) | 0.0040 (8) | 0.0236 (7) | 0.0137 (14) |
C22 | 0.0339 (12) | 0.060 (2) | 0.0599 (19) | −0.0029 (12) | 0.0222 (15) | 0.0149 (14) |
N211 | 0.0397 (7) | 0.0557 (18) | 0.0398 (9) | −0.0131 (8) | 0.0201 (7) | −0.0099 (8) |
N212 | 0.0371 (7) | 0.051 (2) | 0.0396 (9) | −0.0126 (10) | 0.0211 (6) | −0.0059 (10) |
C213 | 0.0284 (15) | 0.029 (4) | 0.0435 (9) | 0.003 (2) | 0.0202 (9) | −0.0015 (16) |
O213 | 0.0343 (18) | 0.052 (4) | 0.0404 (7) | −0.007 (2) | 0.0170 (9) | −0.0066 (18) |
C214 | 0.0312 (12) | 0.038 (3) | 0.0442 (9) | 0.0035 (18) | 0.0222 (8) | 0.0033 (13) |
C215 | 0.0362 (11) | 0.0553 (19) | 0.0418 (10) | 0.0001 (8) | 0.0221 (10) | −0.0007 (12) |
C216 | 0.066 (2) | 0.070 (2) | 0.067 (3) | −0.0303 (13) | 0.033 (3) | −0.0273 (16) |
C217 | 0.050 (2) | 0.1021 (19) | 0.0416 (12) | −0.003 (2) | 0.0234 (13) | −0.0033 (14) |
C221 | 0.0298 (16) | 0.051 (2) | 0.042 (2) | −0.0077 (15) | 0.017 (2) | 0.0010 (18) |
C222 | 0.0437 (16) | 0.0665 (17) | 0.054 (3) | −0.0084 (13) | 0.025 (3) | 0.004 (2) |
C223 | 0.0453 (15) | 0.098 (4) | 0.0595 (15) | −0.005 (4) | 0.0238 (14) | 0.0260 (19) |
C224 | 0.051 (5) | 0.068 (2) | 0.086 (3) | 0.000 (3) | 0.027 (6) | 0.029 (2) |
C225 | 0.069 (4) | 0.047 (2) | 0.092 (4) | 0.009 (4) | 0.036 (5) | 0.014 (2) |
C226 | 0.053 (2) | 0.066 (3) | 0.0685 (16) | −0.011 (3) | 0.0349 (15) | 0.004 (2) |
C231 | 0.0470 (9) | 0.0461 (11) | 0.0512 (10) | −0.0155 (8) | 0.0320 (8) | −0.0093 (8) |
C232 | 0.0483 (17) | 0.055 (5) | 0.0749 (18) | −0.014 (3) | 0.0372 (15) | −0.005 (3) |
C233 | 0.0643 (18) | 0.082 (9) | 0.111 (2) | −0.022 (3) | 0.0634 (19) | −0.019 (4) |
C234 | 0.105 (2) | 0.066 (7) | 0.102 (2) | −0.050 (4) | 0.086 (2) | −0.041 (3) |
C235 | 0.101 (2) | 0.087 (9) | 0.0580 (14) | −0.037 (3) | 0.0546 (15) | −0.018 (3) |
C236 | 0.0594 (12) | 0.083 (4) | 0.0477 (12) | −0.0184 (13) | 0.0316 (10) | −0.0078 (18) |
Cl26 | 0.150 (2) | 0.183 (3) | 0.0636 (11) | −0.0293 (19) | 0.0536 (13) | 0.0027 (13) |
C11—O11 | 1.257 (15) | C21—O21 | 1.258 (16) |
C11—N11 | 1.353 (5) | C21—N21 | 1.355 (5) |
C11—C12 | 1.524 (3) | C21—C22 | 1.528 (4) |
N11—C114 | 1.410 (3) | N21—C214 | 1.410 (3) |
N11—H11 | 0.82 (7) | N21—H21 | 0.91 (8) |
C12—C121 | 1.493 (3) | C22—C221 | 1.492 (4) |
C12—H12A | 0.9700 | C22—H22A | 0.9700 |
C12—H12B | 0.9700 | C22—H22B | 0.9700 |
N111—C115 | 1.373 (3) | N211—C215 | 1.373 (4) |
N111—N112 | 1.407 (3) | N211—N212 | 1.406 (4) |
N111—C116 | 1.467 (3) | N211—C216 | 1.467 (4) |
N112—C113 | 1.389 (3) | N212—C213 | 1.389 (4) |
N112—C131 | 1.427 (3) | N212—C231 | 1.427 (4) |
C113—O113 | 1.237 (3) | C213—O213 | 1.237 (3) |
C113—C114 | 1.430 (3) | C213—C214 | 1.430 (4) |
C114—C115 | 1.353 (5) | C214—C215 | 1.353 (5) |
C115—C117 | 1.487 (4) | C215—C217 | 1.487 (4) |
C116—H11A | 0.9600 | C216—H21A | 0.9600 |
C116—H11B | 0.9600 | C216—H21B | 0.9600 |
C116—H11C | 0.9600 | C216—H21C | 0.9600 |
C117—H11D | 0.9600 | C217—H21D | 0.9600 |
C117—H11E | 0.9600 | C217—H21E | 0.9600 |
C117—H11F | 0.9600 | C217—H21F | 0.9600 |
C121—C122 | 1.370 (4) | C221—C222 | 1.365 (5) |
C121—C126 | 1.397 (4) | C221—C226 | 1.399 (5) |
C122—C123 | 1.417 (4) | C222—C223 | 1.418 (5) |
C122—Cl12 | 1.730 (5) | C222—H222 | 0.9300 |
C123—C124 | 1.372 (5) | C223—C224 | 1.372 (5) |
C123—H123 | 0.9300 | C223—H223 | 0.9300 |
C124—C125 | 1.354 (5) | C224—C225 | 1.355 (5) |
C124—H124 | 0.9300 | C224—H224 | 0.9300 |
C125—C126 | 1.368 (5) | C225—C226 | 1.366 (5) |
C125—H125 | 0.9300 | C225—H225 | 0.9300 |
C126—H126 | 0.9300 | C226—Cl26 | 1.719 (7) |
C131—C136 | 1.366 (4) | C231—C236 | 1.366 (4) |
C131—C132 | 1.388 (5) | C231—C232 | 1.388 (6) |
C132—C133 | 1.385 (4) | C232—C233 | 1.386 (5) |
C132—H132 | 0.9300 | C232—H232 | 0.9300 |
C133—C134 | 1.356 (5) | C233—C234 | 1.357 (5) |
C133—H133 | 0.9300 | C233—H233 | 0.9300 |
C134—C135 | 1.360 (5) | C234—C235 | 1.360 (5) |
C134—H134 | 0.9300 | C234—H234 | 0.9300 |
C135—C136 | 1.401 (7) | C235—C236 | 1.402 (8) |
C135—H135 | 0.9300 | C235—H235 | 0.9300 |
C136—H136 | 0.9300 | C236—H236 | 0.9300 |
O11—C11—N11 | 119.8 (9) | O21—C21—N21 | 119.6 (12) |
O11—C11—C12 | 124.4 (4) | O21—C21—C22 | 124.0 (6) |
N11—C11—C12 | 113.4 (3) | N21—C21—C22 | 112.5 (4) |
C11—N11—C114 | 122.9 (5) | C21—N21—C214 | 123.1 (6) |
C11—N11—H11 | 121 (4) | C21—N21—H21 | 114 (6) |
C114—N11—H11 | 116 (4) | C214—N21—H21 | 123 (6) |
C121—C12—C11 | 114.1 (3) | C221—C22—C21 | 113.8 (4) |
C121—C12—H12A | 108.7 | C221—C22—H22A | 108.8 |
C11—C12—H12A | 108.7 | C21—C22—H22A | 108.8 |
C121—C12—H12B | 108.7 | C221—C22—H22B | 108.8 |
C11—C12—H12B | 108.7 | C21—C22—H22B | 108.8 |
H12A—C12—H12B | 107.6 | H22A—C22—H22B | 107.7 |
C115—N111—N112 | 106.2 (2) | C215—N211—N212 | 106.5 (4) |
C115—N111—C116 | 119.4 (4) | C215—N211—C216 | 119.3 (6) |
N112—N111—C116 | 114.8 (4) | N212—N211—C216 | 114.7 (6) |
C113—N112—N111 | 109.5 (3) | C213—N212—N211 | 109.7 (3) |
C113—N112—C131 | 126.0 (4) | C213—N212—C231 | 125.9 (6) |
N111—N112—C131 | 118.1 (4) | N211—N212—C231 | 118.0 (6) |
O113—C113—N112 | 124.5 (3) | O213—C213—N212 | 124.4 (5) |
O113—C113—C114 | 130.7 (3) | O213—C213—C214 | 130.4 (5) |
N112—C113—C114 | 104.8 (2) | N212—C213—C214 | 104.9 (3) |
C115—C114—N11 | 127.0 (4) | C215—C214—N21 | 126.9 (6) |
C115—C114—C113 | 108.9 (2) | C215—C214—C213 | 108.9 (3) |
N11—C114—C113 | 124.1 (3) | N21—C214—C213 | 123.8 (5) |
C114—C115—N111 | 109.8 (4) | C214—C215—N211 | 109.9 (3) |
C114—C115—C117 | 129.5 (3) | C214—C215—C217 | 129.3 (6) |
N111—C115—C117 | 120.7 (4) | N211—C215—C217 | 120.7 (5) |
N111—C116—H11A | 109.5 | N211—C216—H21A | 109.5 |
N111—C116—H11B | 109.5 | N211—C216—H21B | 109.5 |
H11A—C116—H11B | 109.5 | H21A—C216—H21B | 109.5 |
N111—C116—H11C | 109.5 | N211—C216—H21C | 109.5 |
H11A—C116—H11C | 109.5 | H21A—C216—H21C | 109.5 |
H11B—C116—H11C | 109.5 | H21B—C216—H21C | 109.5 |
C115—C117—H11D | 109.5 | C215—C217—H21D | 109.5 |
C115—C117—H11E | 109.5 | C215—C217—H21E | 109.5 |
H11D—C117—H11E | 109.5 | H21D—C217—H21E | 109.5 |
C115—C117—H11F | 109.5 | C215—C217—H21F | 109.5 |
H11D—C117—H11F | 109.5 | H21D—C217—H21F | 109.5 |
H11E—C117—H11F | 109.5 | H21E—C217—H21F | 109.5 |
C122—C121—C126 | 116.8 (3) | C222—C221—C226 | 116.8 (4) |
C122—C121—C12 | 120.3 (3) | C222—C221—C22 | 121.0 (5) |
C126—C121—C12 | 122.9 (3) | C226—C221—C22 | 122.1 (5) |
C121—C122—C123 | 122.3 (3) | C221—C222—C223 | 122.3 (5) |
C121—C122—Cl12 | 121.9 (3) | C221—C222—H222 | 118.9 |
C123—C122—Cl12 | 115.7 (3) | C223—C222—H222 | 118.9 |
C124—C123—C122 | 117.6 (3) | C224—C223—C222 | 117.5 (5) |
C124—C123—H123 | 121.2 | C224—C223—H223 | 121.3 |
C122—C123—H123 | 121.2 | C222—C223—H223 | 121.3 |
C125—C124—C123 | 121.3 (4) | C225—C224—C223 | 121.3 (5) |
C125—C124—H124 | 119.4 | C225—C224—H224 | 119.3 |
C123—C124—H124 | 119.4 | C223—C224—H224 | 119.3 |
C124—C125—C126 | 120.2 (4) | C224—C225—C226 | 119.9 (6) |
C124—C125—H125 | 119.9 | C224—C225—H225 | 120.0 |
C126—C125—H125 | 119.9 | C226—C225—H225 | 120.0 |
C125—C126—C121 | 121.7 (4) | C225—C226—C221 | 121.5 (5) |
C125—C126—H126 | 119.2 | C225—C226—Cl26 | 116.6 (6) |
C121—C126—H126 | 119.2 | C221—C226—Cl26 | 121.3 (5) |
C136—C131—C132 | 120.6 (4) | C236—C231—C232 | 120.4 (6) |
C136—C131—N112 | 119.1 (4) | C236—C231—N212 | 119.3 (5) |
C132—C131—N112 | 120.2 (3) | C232—C231—N212 | 120.1 (5) |
C133—C132—C131 | 119.2 (4) | C233—C232—C231 | 119.0 (6) |
C133—C132—H132 | 120.4 | C233—C232—H232 | 120.5 |
C131—C132—H132 | 120.4 | C231—C232—H232 | 120.5 |
C134—C133—C132 | 120.8 (4) | C234—C233—C232 | 120.5 (5) |
C134—C133—H133 | 119.6 | C234—C233—H233 | 119.8 |
C132—C133—H133 | 119.6 | C232—C233—H233 | 119.8 |
C133—C134—C135 | 119.4 (3) | C233—C234—C235 | 119.3 (5) |
C133—C134—H134 | 120.3 | C233—C234—H234 | 120.4 |
C135—C134—H134 | 120.3 | C235—C234—H234 | 120.4 |
C134—C135—C136 | 121.6 (4) | C234—C235—C236 | 121.3 (6) |
C134—C135—H135 | 119.2 | C234—C235—H235 | 119.3 |
C136—C135—H135 | 119.2 | C236—C235—H235 | 119.3 |
C131—C136—C135 | 118.2 (5) | C231—C236—C235 | 118.0 (7) |
C131—C136—H136 | 120.9 | C231—C236—H236 | 121.0 |
C135—C136—H136 | 120.9 | C235—C236—H236 | 121.0 |
O11—C11—N11—C114 | 21 (3) | O21—C21—N21—C214 | −39 (4) |
C12—C11—N11—C114 | −175.3 (8) | C22—C21—N21—C214 | 162.3 (13) |
O11—C11—C12—C121 | 8 (3) | O21—C21—C22—C221 | 9 (4) |
N11—C11—C12—C121 | −154.8 (9) | N21—C21—C22—C221 | 167.1 (14) |
C115—N111—N112—C113 | −9 (2) | C215—N211—N212—C213 | −3 (3) |
C116—N111—N112—C113 | −144 (2) | C216—N211—N212—C213 | −137 (3) |
C115—N111—N112—C131 | −163 (2) | C215—N211—N212—C231 | −157 (3) |
C116—N111—N112—C131 | 62.8 (19) | C216—N211—N212—C231 | 69 (3) |
N111—N112—C113—O113 | −174.6 (13) | N211—N212—C213—O213 | −171 (2) |
C131—N112—C113—O113 | −23.6 (15) | C231—N212—C213—O213 | −20 (3) |
N111—N112—C113—C114 | 7.2 (13) | N211—N212—C213—C214 | 3 (2) |
C131—N112—C113—C114 | 158.2 (11) | C231—N212—C213—C214 | 153.7 (18) |
C11—N11—C114—C115 | −79 (3) | C21—N21—C214—C215 | −44 (5) |
C11—N11—C114—C113 | 102.8 (15) | C21—N21—C214—C213 | 128 (2) |
O113—C113—C114—C115 | 180 (2) | O213—C213—C214—C215 | 172 (4) |
N112—C113—C114—C115 | −2 (2) | N212—C213—C214—C215 | −1 (4) |
O113—C113—C114—N11 | −1 (2) | O213—C213—C214—N21 | −1 (3) |
N112—C113—C114—N11 | 176.6 (11) | N212—C213—C214—N21 | −173.9 (18) |
N11—C114—C115—N111 | 177.5 (16) | N21—C214—C215—N211 | 172 (3) |
C113—C114—C115—N111 | −4 (3) | C213—C214—C215—N211 | −1 (5) |
N11—C114—C115—C117 | −1 (6) | N21—C214—C215—C217 | −12 (9) |
C113—C114—C115—C117 | 178 (4) | C213—C214—C215—C217 | 175 (6) |
N112—N111—C115—C114 | 8 (3) | N212—N211—C215—C214 | 2 (5) |
C116—N111—C115—C114 | 140 (3) | C216—N211—C215—C214 | 134 (5) |
N112—N111—C115—C117 | −174 (3) | N212—N211—C215—C217 | −174 (5) |
C116—N111—C115—C117 | −42 (3) | C216—N211—C215—C217 | −42 (5) |
C11—C12—C121—C122 | 67.3 (7) | C21—C22—C221—C222 | 96.8 (11) |
C11—C12—C121—C126 | −115.0 (6) | C21—C22—C221—C226 | −87.3 (11) |
C126—C121—C122—C123 | −0.4 (14) | C226—C221—C222—C223 | −2 (2) |
C12—C121—C122—C123 | 177.3 (10) | C22—C221—C222—C223 | 174.4 (17) |
C126—C121—C122—Cl12 | −179.5 (6) | C221—C222—C223—C224 | −2 (4) |
C12—C121—C122—Cl12 | −1.7 (10) | C222—C223—C224—C225 | −1 (6) |
C121—C122—C123—C124 | 1 (3) | C223—C224—C225—C226 | 7 (7) |
Cl12—C122—C123—C124 | 179.9 (19) | C224—C225—C226—C221 | −11 (5) |
C122—C123—C124—C125 | 1 (4) | C224—C225—C226—Cl26 | 178 (3) |
C123—C124—C125—C126 | −4 (4) | C222—C221—C226—C225 | 8 (3) |
C124—C125—C126—C121 | 4 (3) | C22—C221—C226—C225 | −168.2 (19) |
C122—C121—C126—C125 | −1.9 (15) | C222—C221—C226—Cl26 | 178.6 (11) |
C12—C121—C126—C125 | −179.6 (12) | C22—C221—C226—Cl26 | 2.6 (17) |
C113—N112—C131—C136 | 56 (3) | C213—N212—C231—C236 | 56 (4) |
N111—N112—C131—C136 | −155 (2) | N211—N212—C231—C236 | −155 (4) |
C113—N112—C131—C132 | −127.2 (19) | C213—N212—C231—C232 | −118 (3) |
N111—N112—C131—C132 | 22 (2) | N211—N212—C231—C232 | 31 (3) |
C136—C131—C132—C133 | −4 (3) | C236—C231—C232—C233 | 10 (5) |
N112—C131—C132—C133 | 179.1 (13) | N212—C231—C232—C233 | −176 (2) |
C131—C132—C133—C134 | 4 (2) | C231—C232—C233—C234 | −12 (4) |
C132—C133—C134—C135 | 0 (3) | C232—C233—C234—C235 | 3 (5) |
C133—C134—C135—C136 | −4 (4) | C233—C234—C235—C236 | 9 (6) |
C132—C131—C136—C135 | 1 (4) | C232—C231—C236—C235 | 1 (7) |
N112—C131—C136—C135 | 177 (2) | N212—C231—C236—C235 | −173 (4) |
C134—C135—C136—C131 | 4 (5) | C234—C235—C236—C231 | −10 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O113i | 0.82 (7) | 2.15 (8) | 2.94 (2) | 162 (6) |
N11—H11···O213i | 0.82 (7) | 2.08 (8) | 2.88 (2) | 168 (6) |
N21—H21···O113i | 0.92 (10) | 2.00 (10) | 2.91 (2) | 161 (7) |
N21—H21···O213i | 0.92 (10) | 1.95 (10) | 2.82 (3) | 158 (7) |
C134—H134···O11ii | 0.93 | 2.57 | 3.46 (4) | 159 |
C234—H234···O21ii | 0.93 | 2.49 | 3.40 (7) | 164 |
C225—H225···O213iii | 0.93 | 2.39 | 3.28 (2) | 160 |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1, y−1, −z+1/2. |
Parameter | (I) | (II) | (III) | |||
x = 1 | x = 2 | x = 1 | x = 2 | x = 1 | x = 2 | |
Cx13—Cx14—Nx1—Cx1 | ||||||
122.2 (2) | 129.1 (2) | 102.8 (15) | 128 (2) | 121.0 (2) | 136.5 (3) | |
Cx14—Nx1—Nx1—Cx2 | ||||||
-174.36 (18) | 177.29 (19) | -175.3 (8) | 162.3 (13) | -170.6 (2) | 172.7 (2) | |
Nx1—Cx1—Cx2—Cx21 | ||||||
114.3 (2) | -89.3 (3) | -154.8 (9) | 167.12 (14) | 122.2 (2) | -88.9 (3) | |
Cx1—Cx2—Cx21—Cx22 | ||||||
80.8 (3) | -82.5 (3) | 67.3 (7) | 96.8 (11) | -84.8 (3) | -84.7 (3) | |
Nx11—Nx12—Cx31—Cx32 | ||||||
22.6 (3) | -43.9 (3) | 22 (2) | 31 (3) | 26.7 (3) | -34.7 (3) |
For compounds (I) and (III), the indices x (1 or 2) refer to the two independent molecules in the selected asymmetric units; for compound (II), these indices refer to the major and minor disorder components (cf. Figs. 1 and 2) |
D—H···A | D—H | H···A | D···A | D—H···A | ||
(I) | N11—H11···O213 | 0.87 (3) | 1.93 (2) | 2.781 (2) | 169 (2) | |
N21—H21···O113 | 0.84 (2) | 2.01 (2) | 2.845 (2) | 178 (4) | ||
C133—H133···O11i | 0.93 | 2.52 | 3.446 (3) | 171 | ||
(II) | N11—H11···O113ii | 0.82 (7) | 2.15 (8) | 2.94 (2) | 162 (6) | |
N11—H11···O213ii | 0.82 (7) | 2.08 (8) | 2.88 (2) | 168 (6) | ||
N21—H21···O113ii | 0.92 (10) | 2.00 (10) | 2.91 (2) | 161 (7) | ||
N21—H21···O213ii | 0.92 (10) | 1.95 (10) | 2.82 (3) | 158 (7) | ||
C134—H134···O11iii | 0.93 | 2.57 | 3.46 (4) | 159 | ||
C234—H234···O21iii | 0.93 | 2.49 | 3.40 (7) | 164 | ||
C225—H225···O213iv | 0.93 | 2.39 | 3.28 (2) | 160 |
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, y, -z+1/2; (iii) -x+3/2, y+1/2, -z+1/2; (iv) -x+1, y-1, -z+1/2. |
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