Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615010335/sk3587sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010335/sk35871sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010335/sk35872sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010335/sk35873sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010335/sk35874sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010335/sk35875sup6.hkl |
CCDC references: 1403831; 1403830; 1403829; 1403828; 1403827
Data collection: SMART (Bruker, 2008) for (1); APEX2 (Bruker, 2008) for (2), (3), (4), (5). For all compounds, cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015). Molecular graphics: SHELXTL (Sheldrick, 2008) for (1); OLEX2 (Dolomanov et al., 2009) for (2), (3), (4), (5). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) for (1); publCIF (Westrip, 2010) for (2), (3), (4), (5).
[CuCl(C15H17N3)]·0.18H2O | Dx = 1.465 Mg m−3 |
Mr = 341.52 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 9910 reflections |
a = 29.2238 (13) Å | θ = 2.5–27.6° |
b = 8.2252 (4) Å | µ = 1.58 mm−1 |
c = 12.8789 (6) Å | T = 150 K |
V = 3095.7 (2) Å3 | Rhomboid, orange |
Z = 8 | 0.32 × 0.28 × 0.12 mm |
F(000) = 1406 |
Bruker SMART APEXII diffractometer | 10665 independent reflections |
Radiation source: fine-focus sealed tube | 8406 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 8.33 pixels mm-1 | θmax = 32.6°, θmin = 2.1° |
φ and ω scans | h = −43→42 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −12→12 |
Tmin = 0.629, Tmax = 0.837 | l = −18→18 |
37660 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.064 | w = 1/[σ2(Fo2) + (0.0212P)2 + 0.6853P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.041 |
10665 reflections | Δρmax = 0.41 e Å−3 |
608 parameters | Δρmin = −0.43 e Å−3 |
139 restraints | Absolute structure: Refined as an inversion twin. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.504 (10) |
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. Refined as a 2-component inversion twin. Twin component factor refined to 0.503:0.497. Inspection of the structure did not reveal a potential missed inversion center. The ligands were found to be disordered on both copper complex molecules. The disorder was immediately apparent in the orientation of the methylene carbons within the ligand. The model was developed whereby the pyridyl rings were modeled from the geometry of the methylene carbon relative to the pyridyl ring. Inclusion of these atoms with occupancies summed independently to unity for the two molecules, yielded ratios of 0.76:0.34 and 0.57:0.43. These disordered atoms were treated with an anisotropic model. Atoms in the minor components in the molecules were restrained to have similar atomic displacement parameters. Residual electron density was observed in a region located away from the main molecules. It was assumed to be a molecule of water from the crystallization solvent. This residual density was assumed to be solvent water of crystallization. An oxygen atom was included at this site and its occupancy refined independently, yielding an occpancy of 0.35. Hydrogen atoms on the water were included in idealized positions oriented towards nearby chlorine atoms and refined with a fixed O–H distance = 0.85 Å. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cu1 | 0.11243 (2) | 0.82677 (4) | 1.17764 (3) | 0.03331 (8) | |
Cl1 | 0.10667 (3) | 1.09481 (9) | 1.16052 (7) | 0.04425 (19) | |
N2 | 0.12430 (8) | 0.6390 (3) | 1.0519 (2) | 0.0325 (5) | |
N1 | 0.05572 (19) | 0.6797 (7) | 1.1938 (5) | 0.0323 (12) | 0.765 (4) |
C1 | 0.0256 (2) | 0.6867 (9) | 1.2700 (6) | 0.0438 (14) | 0.765 (4) |
H1A | 0.0310 | 0.7618 | 1.3248 | 0.053* | 0.765 (4) |
C2 | −0.0134 (2) | 0.5906 (12) | 1.2749 (7) | 0.061 (2) | 0.765 (4) |
H2A | −0.0349 | 0.6026 | 1.3298 | 0.073* | 0.765 (4) |
C3 | −0.0200 (2) | 0.4786 (12) | 1.1985 (8) | 0.066 (2) | 0.765 (4) |
H3A | −0.0459 | 0.4088 | 1.1999 | 0.079* | 0.765 (4) |
C4 | 0.01060 (19) | 0.4679 (8) | 1.1209 (6) | 0.0557 (15) | 0.765 (4) |
H4A | 0.0065 | 0.3895 | 1.0675 | 0.067* | 0.765 (4) |
C5 | 0.04806 (15) | 0.5709 (6) | 1.1188 (4) | 0.0391 (11) | 0.765 (4) |
C6 | 0.08007 (14) | 0.5699 (6) | 1.0274 (3) | 0.0441 (11) | 0.765 (4) |
H6A | 0.0843 | 0.4565 | 1.0034 | 0.053* | 0.765 (4) |
H6B | 0.0661 | 0.6324 | 0.9698 | 0.053* | 0.765 (4) |
C7 | 0.15281 (12) | 0.5199 (4) | 1.1136 (4) | 0.0353 (8) | 0.765 (4) |
H7A | 0.1328 | 0.4587 | 1.1618 | 0.042* | 0.765 (4) |
H7B | 0.1673 | 0.4410 | 1.0657 | 0.042* | 0.765 (4) |
C8 | 0.18899 (13) | 0.6066 (5) | 1.1739 (4) | 0.0320 (8) | 0.765 (4) |
C9 | 0.23381 (18) | 0.5495 (7) | 1.1840 (5) | 0.0448 (14) | 0.765 (4) |
H9A | 0.2429 | 0.4526 | 1.1495 | 0.054* | 0.765 (4) |
C10 | 0.2647 (2) | 0.6335 (13) | 1.2440 (8) | 0.057 (4) | 0.765 (4) |
H10A | 0.2953 | 0.5955 | 1.2512 | 0.069* | 0.765 (4) |
C11 | 0.2511 (3) | 0.7705 (14) | 1.2923 (6) | 0.0460 (19) | 0.765 (4) |
H11A | 0.2718 | 0.8321 | 1.3335 | 0.055* | 0.765 (4) |
C12 | 0.2062 (2) | 0.8185 (11) | 1.2800 (5) | 0.038 (4) | 0.765 (4) |
H12A | 0.1966 | 0.9139 | 1.3154 | 0.046* | 0.765 (4) |
N3 | 0.1756 (2) | 0.7417 (7) | 1.2227 (4) | 0.0306 (12) | 0.765 (4) |
C13 | 0.15056 (14) | 0.6874 (6) | 0.9602 (3) | 0.0379 (10) | 0.765 (4) |
H13A | 0.1514 | 0.5971 | 0.9094 | 0.045* | 0.765 (4) |
H13B | 0.1824 | 0.7138 | 0.9803 | 0.045* | 0.765 (4) |
C1A | 0.0265 (7) | 0.7338 (18) | 1.2829 (13) | 0.031 (4) | 0.235 (4) |
H1AA | 0.0297 | 0.8272 | 1.3257 | 0.037* | 0.235 (4) |
C2A | −0.0137 (6) | 0.643 (2) | 1.2862 (16) | 0.050 (7) | 0.235 (4) |
H2AA | −0.0378 | 0.6750 | 1.3312 | 0.060* | 0.235 (4) |
C3A | −0.0184 (5) | 0.507 (2) | 1.2236 (17) | 0.051 (8) | 0.235 (4) |
H3AA | −0.0459 | 0.4449 | 1.2259 | 0.061* | 0.235 (4) |
C4A | 0.0169 (5) | 0.4605 (16) | 1.1578 (12) | 0.052 (6) | 0.235 (4) |
H4AA | 0.0137 | 0.3671 | 1.1151 | 0.062* | 0.235 (4) |
C5A | 0.0571 (4) | 0.5510 (17) | 1.1545 (9) | 0.031 (4) | 0.235 (4) |
N1A | 0.0619 (5) | 0.6876 (18) | 1.2171 (11) | 0.026 (4) | 0.235 (4) |
C6A | 0.0996 (4) | 0.5042 (14) | 1.0951 (11) | 0.036 (3) | 0.235 (4) |
H6AA | 0.1203 | 0.4437 | 1.1422 | 0.043* | 0.235 (4) |
H6AB | 0.0908 | 0.4299 | 1.0381 | 0.043* | 0.235 (4) |
C7A | 0.1706 (5) | 0.6225 (17) | 1.0321 (11) | 0.039 (3) | 0.235 (4) |
H7AA | 0.1806 | 0.7052 | 0.9810 | 0.047* | 0.235 (4) |
H7AB | 0.1770 | 0.5135 | 1.0030 | 0.047* | 0.235 (4) |
C8A | 0.1961 (4) | 0.6445 (15) | 1.1315 (9) | 0.030 (3) | 0.235 (4) |
C9A | 0.2386 (4) | 0.5729 (19) | 1.1481 (12) | 0.039 (4) | 0.235 (4) |
H9AA | 0.2496 | 0.4925 | 1.1015 | 0.046* | 0.235 (4) |
C10A | 0.2650 (6) | 0.619 (3) | 1.2330 (17) | 0.043 (9) | 0.235 (4) |
H10B | 0.2940 | 0.5703 | 1.2443 | 0.052* | 0.235 (4) |
C11A | 0.2489 (9) | 0.737 (3) | 1.3012 (16) | 0.054 (11) | 0.235 (4) |
H11B | 0.2669 | 0.7685 | 1.3592 | 0.065* | 0.235 (4) |
C12A | 0.2064 (9) | 0.808 (3) | 1.2846 (13) | 0.052 (16) | 0.235 (4) |
H12B | 0.1954 | 0.8889 | 1.3313 | 0.062* | 0.235 (4) |
N3A | 0.1800 (6) | 0.7622 (18) | 1.1998 (11) | 0.023 (4) | 0.235 (4) |
C13A | 0.0977 (4) | 0.6876 (16) | 0.9475 (10) | 0.035 (3) | 0.235 (4) |
H13C | 0.0983 | 0.5985 | 0.8958 | 0.042* | 0.235 (4) |
H13D | 0.0655 | 0.7188 | 0.9616 | 0.042* | 0.235 (4) |
C14 | 0.12740 (15) | 0.8387 (5) | 0.9109 (3) | 0.0563 (10) | |
H14A | 0.1153 | 0.9204 | 0.9553 | 0.068* | 0.565 (4) |
H14B | 0.1451 | 0.9056 | 0.9555 | 0.068* | 0.435 (4) |
C15 | 0.12395 (14) | 0.8575 (6) | 0.8108 (3) | 0.0571 (11) | |
H15A | 0.1358 | 0.7771 | 0.7653 | 0.068* | 0.565 (4) |
H15B | 0.1095 | 0.9517 | 0.7833 | 0.068* | 0.565 (4) |
H15C | 0.1055 | 0.7854 | 0.7713 | 0.068* | 0.435 (4) |
H15D | 0.1399 | 0.9434 | 0.7773 | 0.068* | 0.435 (4) |
Cu2 | 0.13512 (2) | 0.25376 (4) | 0.61403 (4) | 0.03450 (8) | |
Cl2 | 0.13969 (3) | 0.34561 (11) | 0.77561 (6) | 0.04546 (19) | |
N5 | 0.13422 (8) | 0.3807 (3) | 0.4570 (2) | 0.0364 (6) | |
C20 | 0.0731 (3) | 0.1865 (11) | 0.4551 (9) | 0.0424 (19) | 0.565 (4) |
N4 | 0.0783 (3) | 0.1566 (13) | 0.5539 (9) | 0.032 (2) | 0.565 (4) |
C16 | 0.0438 (6) | 0.082 (2) | 0.5963 (14) | 0.054 (4) | 0.565 (4) |
H16A | 0.0469 | 0.0585 | 0.6682 | 0.065* | 0.565 (4) |
C17 | 0.0040 (5) | 0.032 (2) | 0.5521 (17) | 0.061 (4) | 0.565 (4) |
H17A | −0.0196 | −0.0193 | 0.5906 | 0.074* | 0.565 (4) |
C18 | 0.0004 (5) | 0.063 (3) | 0.4470 (18) | 0.070 (4) | 0.565 (4) |
H18A | −0.0259 | 0.0284 | 0.4095 | 0.084* | 0.565 (4) |
C19 | 0.0343 (4) | 0.1419 (17) | 0.3986 (10) | 0.058 (3) | 0.565 (4) |
H19A | 0.0319 | 0.1673 | 0.3268 | 0.070* | 0.565 (4) |
C20A | 0.0601 (3) | 0.2275 (13) | 0.4562 (10) | 0.039 (2) | 0.435 (4) |
N4A | 0.0719 (4) | 0.1884 (15) | 0.5577 (10) | 0.030 (3) | 0.435 (4) |
C16A | 0.0447 (5) | 0.082 (2) | 0.6147 (12) | 0.041 (5) | 0.435 (4) |
H16B | 0.0528 | 0.0555 | 0.6841 | 0.050* | 0.435 (4) |
C17A | 0.0057 (6) | 0.015 (3) | 0.5702 (17) | 0.078 (10) | 0.435 (4) |
H17B | −0.0129 | −0.0572 | 0.6092 | 0.094* | 0.435 (4) |
C18A | −0.0061 (4) | 0.054 (2) | 0.4687 (16) | 0.067 (8) | 0.435 (4) |
H18B | −0.0328 | 0.0087 | 0.4383 | 0.080* | 0.435 (4) |
C19A | 0.0211 (4) | 0.161 (2) | 0.4117 (11) | 0.065 (5) | 0.435 (4) |
H19B | 0.0130 | 0.1873 | 0.3423 | 0.078* | 0.435 (4) |
C21 | 0.1122 (2) | 0.2640 (8) | 0.3977 (4) | 0.0438 (15) | 0.565 (4) |
H21A | 0.1345 | 0.1789 | 0.3776 | 0.053* | 0.565 (4) |
H21B | 0.1005 | 0.3149 | 0.3333 | 0.053* | 0.565 (4) |
C22 | 0.18080 (18) | 0.4193 (7) | 0.4282 (4) | 0.0374 (13) | 0.565 (4) |
H22A | 0.1895 | 0.5259 | 0.4580 | 0.045* | 0.565 (4) |
H22B | 0.1832 | 0.4269 | 0.3516 | 0.045* | 0.565 (4) |
C23 | 0.21301 (19) | 0.2886 (8) | 0.4680 (4) | 0.0319 (12) | 0.565 (4) |
C24 | 0.2554 (3) | 0.2653 (8) | 0.4216 (7) | 0.0379 (15) | 0.565 (4) |
H24A | 0.2633 | 0.3256 | 0.3613 | 0.045* | 0.565 (4) |
C25 | 0.2851 (7) | 0.159 (3) | 0.4609 (11) | 0.039 (3) | 0.565 (4) |
H25A | 0.3138 | 0.1419 | 0.4284 | 0.047* | 0.565 (4) |
C26 | 0.2734 (4) | 0.0749 (12) | 0.5499 (7) | 0.041 (2) | 0.565 (4) |
H26A | 0.2947 | 0.0035 | 0.5819 | 0.050* | 0.565 (4) |
C27 | 0.2306 (6) | 0.0954 (16) | 0.5912 (8) | 0.036 (2) | 0.565 (4) |
H27A | 0.2219 | 0.0303 | 0.6489 | 0.044* | 0.565 (4) |
N6 | 0.2000 (4) | 0.2050 (9) | 0.5533 (10) | 0.0279 (16) | 0.565 (4) |
C28 | 0.10605 (18) | 0.5414 (7) | 0.4561 (4) | 0.0360 (13) | 0.565 (4) |
H28A | 0.1060 | 0.5892 | 0.3856 | 0.043* | 0.565 (4) |
H28B | 0.0740 | 0.5196 | 0.4767 | 0.043* | 0.565 (4) |
C21A | 0.0879 (3) | 0.3661 (10) | 0.4135 (6) | 0.044 (2) | 0.435 (4) |
H21C | 0.0905 | 0.3528 | 0.3374 | 0.053* | 0.435 (4) |
H21D | 0.0713 | 0.4689 | 0.4267 | 0.053* | 0.435 (4) |
C22A | 0.1637 (2) | 0.2446 (9) | 0.3957 (5) | 0.0344 (16) | 0.435 (4) |
H22C | 0.1446 | 0.1471 | 0.3830 | 0.041* | 0.435 (4) |
H22D | 0.1738 | 0.2880 | 0.3277 | 0.041* | 0.435 (4) |
C23A | 0.2041 (2) | 0.2001 (10) | 0.4595 (6) | 0.0291 (14) | 0.435 (4) |
C24A | 0.2485 (5) | 0.1974 (11) | 0.4206 (10) | 0.041 (2) | 0.435 (4) |
H24B | 0.2544 | 0.2267 | 0.3506 | 0.050* | 0.435 (4) |
C25A | 0.2853 (9) | 0.149 (3) | 0.4885 (13) | 0.039 (4) | 0.435 (4) |
H25B | 0.3161 | 0.1487 | 0.4647 | 0.047* | 0.435 (4) |
C26A | 0.2749 (5) | 0.1057 (16) | 0.5864 (9) | 0.040 (3) | 0.435 (4) |
H26B | 0.2980 | 0.0671 | 0.6321 | 0.048* | 0.435 (4) |
C27A | 0.2297 (7) | 0.118 (2) | 0.6193 (11) | 0.035 (3) | 0.435 (4) |
H27B | 0.2231 | 0.0954 | 0.6901 | 0.042* | 0.435 (4) |
N6A | 0.1950 (5) | 0.1595 (12) | 0.5572 (14) | 0.029 (2) | 0.435 (4) |
C28A | 0.1560 (3) | 0.5289 (9) | 0.4437 (6) | 0.045 (2) | 0.435 (4) |
H28C | 0.1527 | 0.5686 | 0.3715 | 0.054* | 0.435 (4) |
H28D | 0.1889 | 0.5212 | 0.4610 | 0.054* | 0.435 (4) |
C29 | 0.12750 (17) | 0.6542 (5) | 0.5301 (4) | 0.0672 (12) | |
H29A | 0.1421 | 0.6161 | 0.5913 | 0.081* | 0.565 (4) |
H29B | 0.1138 | 0.6120 | 0.5913 | 0.081* | 0.435 (4) |
C30 | 0.12567 (18) | 0.8041 (5) | 0.5087 (4) | 0.0743 (14) | |
H30A | 0.1109 | 0.8394 | 0.4470 | 0.089* | 0.565 (4) |
H30B | 0.1391 | 0.8814 | 0.5543 | 0.089* | 0.565 (4) |
H30C | 0.1396 | 0.8439 | 0.4471 | 0.089* | 0.435 (4) |
H30D | 0.1103 | 0.8769 | 0.5542 | 0.089* | 0.435 (4) |
O1W | 0.0746 (3) | 0.1987 (10) | 0.9325 (7) | 0.062 (3) | 0.356 (9) |
H1WB | 0.0822 | 0.1736 | 0.9937 | 0.093* | 0.3558 |
H1WA | 0.0931 | 0.2414 | 0.8880 | 0.093* | 0.3558 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.02953 (14) | 0.03819 (17) | 0.03223 (16) | 0.00511 (14) | 0.00027 (17) | −0.00228 (18) |
Cl1 | 0.0450 (4) | 0.0343 (3) | 0.0534 (5) | −0.0043 (3) | −0.0062 (4) | −0.0054 (4) |
N2 | 0.0295 (11) | 0.0363 (13) | 0.0317 (12) | −0.0055 (9) | 0.0041 (10) | −0.0035 (11) |
N1 | 0.0218 (17) | 0.046 (3) | 0.029 (3) | 0.0018 (16) | 0.001 (2) | 0.0090 (18) |
C1 | 0.036 (3) | 0.052 (4) | 0.043 (3) | 0.012 (3) | 0.010 (2) | 0.002 (3) |
C2 | 0.027 (3) | 0.090 (6) | 0.065 (4) | 0.006 (3) | 0.023 (3) | 0.026 (5) |
C3 | 0.034 (3) | 0.094 (5) | 0.068 (5) | −0.025 (3) | 0.000 (3) | 0.025 (4) |
C4 | 0.038 (3) | 0.069 (3) | 0.060 (4) | −0.021 (2) | −0.005 (3) | 0.010 (3) |
C5 | 0.026 (2) | 0.051 (3) | 0.041 (3) | −0.0032 (17) | 0.000 (2) | 0.009 (3) |
C6 | 0.032 (2) | 0.060 (3) | 0.040 (2) | −0.0143 (19) | −0.0018 (17) | −0.007 (2) |
C7 | 0.0337 (17) | 0.0312 (17) | 0.0410 (19) | −0.0013 (14) | 0.0073 (18) | −0.0037 (19) |
C8 | 0.0295 (18) | 0.0336 (19) | 0.033 (2) | 0.0019 (14) | 0.005 (2) | 0.005 (2) |
C9 | 0.038 (2) | 0.043 (3) | 0.054 (4) | 0.013 (2) | 0.010 (3) | 0.010 (3) |
C10 | 0.023 (3) | 0.068 (6) | 0.081 (6) | 0.003 (3) | −0.010 (3) | 0.027 (4) |
C11 | 0.030 (3) | 0.058 (4) | 0.050 (4) | −0.006 (3) | −0.014 (2) | 0.019 (3) |
C12 | 0.031 (4) | 0.046 (5) | 0.037 (4) | 0.000 (2) | −0.012 (2) | 0.004 (3) |
N3 | 0.028 (2) | 0.034 (2) | 0.030 (3) | 0.0005 (18) | −0.0010 (19) | 0.007 (2) |
C13 | 0.0310 (19) | 0.051 (2) | 0.032 (2) | −0.0031 (18) | 0.0074 (16) | −0.0058 (18) |
C1A | 0.029 (6) | 0.036 (7) | 0.028 (6) | 0.004 (5) | 0.011 (5) | −0.002 (5) |
C2A | 0.045 (9) | 0.049 (9) | 0.055 (9) | −0.002 (6) | 0.003 (6) | 0.003 (6) |
C3A | 0.048 (10) | 0.052 (9) | 0.053 (10) | −0.004 (6) | 0.004 (6) | 0.005 (6) |
C4A | 0.052 (8) | 0.051 (7) | 0.053 (9) | −0.010 (5) | −0.008 (6) | 0.001 (6) |
C5A | 0.029 (5) | 0.032 (5) | 0.032 (6) | −0.004 (4) | −0.003 (5) | 0.011 (5) |
N1A | 0.024 (6) | 0.031 (6) | 0.022 (6) | 0.005 (4) | −0.008 (4) | 0.004 (4) |
C6A | 0.042 (5) | 0.027 (4) | 0.040 (6) | 0.000 (4) | −0.002 (4) | −0.007 (4) |
C7A | 0.037 (5) | 0.042 (5) | 0.039 (5) | 0.008 (4) | 0.006 (4) | 0.001 (5) |
C8A | 0.023 (5) | 0.032 (5) | 0.034 (6) | 0.003 (4) | −0.001 (4) | 0.001 (5) |
C9A | 0.030 (6) | 0.040 (6) | 0.046 (7) | 0.008 (5) | −0.002 (5) | 0.011 (5) |
C10A | 0.036 (11) | 0.044 (10) | 0.049 (10) | 0.012 (6) | 0.007 (6) | 0.002 (6) |
C11A | 0.050 (12) | 0.058 (13) | 0.053 (12) | −0.001 (6) | −0.004 (6) | 0.013 (6) |
C12A | 0.054 (17) | 0.049 (17) | 0.052 (17) | −0.001 (7) | 0.003 (7) | 0.004 (7) |
N3A | 0.022 (5) | 0.025 (5) | 0.022 (6) | −0.005 (4) | 0.002 (4) | 0.012 (4) |
C13A | 0.033 (5) | 0.038 (5) | 0.034 (5) | 0.005 (4) | −0.004 (4) | −0.002 (4) |
C14 | 0.075 (3) | 0.061 (2) | 0.0337 (18) | −0.016 (2) | 0.0046 (18) | −0.0005 (17) |
C15 | 0.049 (2) | 0.088 (3) | 0.0350 (18) | 0.004 (2) | −0.0065 (15) | 0.0071 (19) |
Cu2 | 0.03731 (16) | 0.03626 (16) | 0.02991 (14) | 0.00496 (16) | 0.00265 (17) | 0.00215 (16) |
Cl2 | 0.0503 (5) | 0.0516 (5) | 0.0345 (4) | −0.0022 (4) | −0.0035 (3) | −0.0068 (4) |
N5 | 0.0344 (13) | 0.0426 (15) | 0.0322 (13) | 0.0074 (11) | −0.0009 (11) | 0.0051 (11) |
C20 | 0.035 (5) | 0.042 (5) | 0.051 (4) | 0.006 (3) | −0.010 (4) | −0.011 (4) |
N4 | 0.031 (3) | 0.018 (4) | 0.049 (4) | 0.011 (3) | 0.010 (3) | −0.009 (3) |
C16 | 0.047 (8) | 0.057 (10) | 0.059 (6) | 0.006 (6) | 0.001 (5) | 0.002 (5) |
C17 | 0.020 (6) | 0.062 (8) | 0.102 (11) | −0.005 (5) | 0.002 (6) | −0.009 (8) |
C18 | 0.038 (6) | 0.091 (11) | 0.081 (7) | 0.001 (6) | −0.005 (7) | −0.032 (7) |
C19 | 0.035 (5) | 0.077 (7) | 0.062 (5) | 0.000 (5) | −0.006 (4) | −0.028 (5) |
C20A | 0.031 (5) | 0.044 (6) | 0.041 (5) | 0.015 (4) | −0.010 (4) | −0.006 (4) |
N4A | 0.029 (4) | 0.020 (5) | 0.042 (5) | 0.015 (3) | 0.002 (3) | −0.014 (3) |
C16A | 0.017 (6) | 0.044 (9) | 0.063 (9) | 0.000 (6) | 0.016 (5) | 0.000 (6) |
C17A | 0.038 (11) | 0.064 (11) | 0.13 (2) | 0.013 (8) | 0.016 (11) | 0.014 (11) |
C18A | 0.024 (6) | 0.056 (10) | 0.12 (2) | 0.002 (5) | −0.008 (9) | −0.029 (11) |
C19A | 0.029 (7) | 0.093 (10) | 0.072 (9) | 0.009 (7) | −0.008 (6) | −0.035 (8) |
C21 | 0.047 (3) | 0.052 (4) | 0.033 (3) | 0.010 (3) | −0.005 (3) | −0.009 (3) |
C22 | 0.037 (3) | 0.036 (3) | 0.039 (3) | 0.010 (2) | 0.010 (2) | 0.014 (2) |
C23 | 0.030 (3) | 0.031 (3) | 0.035 (3) | 0.005 (2) | 0.004 (2) | 0.001 (2) |
C24 | 0.034 (4) | 0.037 (3) | 0.043 (3) | 0.007 (3) | 0.010 (3) | 0.006 (3) |
C25 | 0.038 (5) | 0.037 (4) | 0.041 (6) | 0.007 (3) | 0.010 (5) | 0.003 (5) |
C26 | 0.039 (4) | 0.043 (4) | 0.043 (5) | 0.018 (3) | 0.000 (4) | 0.004 (4) |
C27 | 0.042 (4) | 0.027 (4) | 0.041 (5) | 0.009 (3) | 0.004 (4) | 0.004 (4) |
N6 | 0.027 (3) | 0.021 (4) | 0.036 (3) | 0.001 (3) | 0.001 (2) | 0.001 (4) |
C28 | 0.035 (3) | 0.039 (3) | 0.034 (3) | 0.014 (2) | 0.004 (2) | 0.005 (2) |
C21A | 0.041 (4) | 0.055 (5) | 0.036 (4) | 0.017 (4) | −0.007 (3) | 0.003 (3) |
C22A | 0.041 (4) | 0.033 (3) | 0.029 (3) | 0.009 (3) | 0.001 (3) | −0.002 (3) |
C23A | 0.031 (3) | 0.025 (3) | 0.031 (3) | 0.002 (3) | 0.003 (3) | −0.005 (3) |
C24A | 0.043 (4) | 0.036 (4) | 0.045 (4) | 0.000 (4) | 0.010 (3) | −0.006 (4) |
C25A | 0.030 (5) | 0.041 (6) | 0.046 (8) | 0.011 (4) | 0.001 (6) | 0.001 (6) |
C26A | 0.035 (4) | 0.041 (5) | 0.045 (6) | 0.007 (3) | −0.003 (4) | 0.004 (4) |
C27A | 0.032 (4) | 0.034 (5) | 0.040 (6) | 0.004 (4) | 0.001 (5) | −0.001 (4) |
N6A | 0.031 (4) | 0.020 (5) | 0.036 (4) | −0.001 (4) | −0.003 (3) | −0.003 (4) |
C28A | 0.059 (5) | 0.033 (4) | 0.044 (4) | 0.014 (4) | 0.010 (4) | 0.006 (3) |
C29 | 0.104 (3) | 0.040 (2) | 0.058 (3) | −0.010 (2) | −0.010 (2) | 0.0094 (18) |
C30 | 0.089 (3) | 0.052 (2) | 0.082 (3) | 0.022 (2) | 0.030 (3) | 0.009 (2) |
O1W | 0.056 (5) | 0.059 (5) | 0.071 (6) | −0.003 (4) | 0.007 (4) | 0.019 (4) |
Cu1—N1A | 1.937 (12) | Cu2—N6A | 2.050 (17) |
Cu1—N3 | 2.058 (5) | Cu2—N4A | 2.056 (10) |
Cu1—N1 | 2.063 (5) | Cu2—N6 | 2.090 (12) |
Cu1—N3A | 2.066 (15) | Cu2—Cl2 | 2.2178 (9) |
Cu1—Cl1 | 2.2221 (8) | Cu2—N5 | 2.276 (3) |
Cu1—N2 | 2.265 (2) | N5—C21 | 1.385 (7) |
N2—C7A | 1.385 (13) | N5—C28A | 1.385 (8) |
N2—C6A | 1.435 (12) | N5—C22 | 1.446 (6) |
N2—C6 | 1.447 (4) | N5—C21A | 1.469 (8) |
N2—C13 | 1.463 (5) | N5—C28 | 1.557 (6) |
N2—C7 | 1.512 (5) | N5—C22A | 1.619 (7) |
N2—C13A | 1.605 (13) | C20—N4 | 1.305 (10) |
N1—C1 | 1.319 (6) | C20—C19 | 1.397 (11) |
N1—C5 | 1.336 (7) | C20—C21 | 1.504 (12) |
C1—C2 | 1.390 (9) | N4—C16 | 1.301 (12) |
C1—H1A | 0.9500 | C16—C17 | 1.358 (14) |
C2—C3 | 1.361 (12) | C16—H16A | 0.9500 |
C2—H2A | 0.9500 | C17—C18 | 1.380 (19) |
C3—C4 | 1.343 (9) | C17—H17A | 0.9500 |
C3—H3A | 0.9500 | C18—C19 | 1.339 (16) |
C4—C5 | 1.385 (6) | C18—H18A | 0.9500 |
C4—H4A | 0.9500 | C19—H19A | 0.9500 |
C5—C6 | 1.503 (7) | C20A—N4A | 1.3900 |
C6—H6A | 0.9900 | C20A—C19A | 1.3900 |
C6—H6B | 0.9900 | C20A—C21A | 1.505 (14) |
C7—C8 | 1.494 (6) | N4A—C16A | 1.3900 |
C7—H7A | 0.9900 | C16A—C17A | 1.3900 |
C7—H7B | 0.9900 | C16A—H16B | 0.9500 |
C8—N3 | 1.334 (6) | C17A—C18A | 1.3900 |
C8—C9 | 1.398 (6) | C17A—H17B | 0.9500 |
C9—C10 | 1.375 (9) | C18A—C19A | 1.3900 |
C9—H9A | 0.9500 | C18A—H18B | 0.9500 |
C10—C11 | 1.347 (10) | C19A—H19B | 0.9500 |
C10—H10A | 0.9500 | C21—H21A | 0.9900 |
C11—C12 | 1.380 (6) | C21—H21B | 0.9900 |
C11—H11A | 0.9500 | C22—C23 | 1.519 (7) |
C12—N3 | 1.321 (6) | C22—H22A | 0.9900 |
C12—H12A | 0.9500 | C22—H22B | 0.9900 |
C13—C14 | 1.552 (6) | C23—N6 | 1.351 (13) |
C13—H13A | 0.9900 | C23—C24 | 1.390 (9) |
C13—H13B | 0.9900 | C24—C25 | 1.33 (2) |
C1A—C2A | 1.3900 | C24—H24A | 0.9500 |
C1A—N1A | 1.3900 | C25—C26 | 1.383 (17) |
C1A—H1AA | 0.9500 | C25—H25A | 0.9500 |
C2A—C3A | 1.3900 | C26—C27 | 1.368 (18) |
C2A—H2AA | 0.9500 | C26—H26A | 0.9500 |
C3A—C4A | 1.3900 | C27—N6 | 1.361 (18) |
C3A—H3AA | 0.9500 | C27—H27A | 0.9500 |
C4A—C5A | 1.3900 | C28—C29 | 1.470 (7) |
C4A—H4AA | 0.9500 | C28—H28A | 0.9900 |
C5A—N1A | 1.3900 | C28—H28B | 0.9900 |
C5A—C6A | 1.509 (17) | C21A—H21C | 0.9900 |
C6A—H6AA | 0.9900 | C21A—H21D | 0.9900 |
C6A—H6AB | 0.9900 | C22A—C23A | 1.486 (10) |
C7A—C8A | 1.492 (18) | C22A—H22C | 0.9900 |
C7A—H7AA | 0.9900 | C22A—H22D | 0.9900 |
C7A—H7AB | 0.9900 | C23A—N6A | 1.329 (19) |
C8A—C9A | 1.3900 | C23A—C24A | 1.389 (15) |
C8A—N3A | 1.3900 | C24A—C25A | 1.44 (3) |
C9A—C10A | 1.3900 | C24A—H24B | 0.9500 |
C9A—H9AA | 0.9500 | C25A—C26A | 1.35 (2) |
C10A—C11A | 1.3900 | C25A—H25B | 0.9500 |
C10A—H10B | 0.9500 | C26A—C27A | 1.39 (2) |
C11A—C12A | 1.3900 | C26A—H26B | 0.9500 |
C11A—H11B | 0.9500 | C27A—N6A | 1.34 (3) |
C12A—N3A | 1.3900 | C27A—H27B | 0.9500 |
C12A—H12B | 0.9500 | C28A—C29 | 1.729 (9) |
C13A—C14 | 1.588 (14) | C28A—H28C | 0.9900 |
C13A—H13C | 0.9900 | C28A—H28D | 0.9900 |
C13A—H13D | 0.9900 | C29—C30 | 1.265 (5) |
C14—C15 | 1.302 (5) | C29—H29A | 0.9500 |
C14—H14A | 0.9500 | C29—H29B | 0.9500 |
C14—H14B | 0.9500 | C30—H30A | 0.9500 |
C15—H15A | 0.9500 | C30—H30B | 0.9500 |
C15—H15B | 0.9500 | C30—H30C | 0.9500 |
C15—H15C | 0.9500 | C30—H30D | 0.9500 |
C15—H15D | 0.9500 | O1W—H1WB | 0.8450 |
Cu2—N4 | 1.999 (10) | O1W—H1WA | 0.8630 |
N3—Cu1—N1 | 119.5 (2) | N4—Cu2—N6 | 122.1 (4) |
N1A—Cu1—N3A | 122.8 (7) | N4—Cu2—Cl2 | 123.4 (3) |
N1A—Cu1—Cl1 | 123.7 (5) | N6A—Cu2—Cl2 | 114.4 (5) |
N3—Cu1—Cl1 | 115.68 (17) | N4A—Cu2—Cl2 | 118.3 (4) |
N1—Cu1—Cl1 | 122.09 (18) | N6—Cu2—Cl2 | 111.2 (4) |
N3A—Cu1—Cl1 | 109.9 (5) | N4—Cu2—N5 | 80.2 (3) |
N1A—Cu1—N2 | 84.4 (4) | N6A—Cu2—N5 | 82.3 (5) |
N3—Cu1—N2 | 80.33 (16) | N4A—Cu2—N5 | 78.2 (4) |
N1—Cu1—N2 | 78.18 (17) | N6—Cu2—N5 | 76.5 (3) |
N3A—Cu1—N2 | 77.1 (4) | Cl2—Cu2—N5 | 132.70 (8) |
Cl1—Cu1—N2 | 128.12 (7) | C21—N5—C22 | 116.6 (4) |
C7A—N2—C6A | 119.2 (8) | C28A—N5—C21A | 116.5 (5) |
C6—N2—C13 | 113.5 (3) | C21—N5—C28 | 109.8 (4) |
C6—N2—C7 | 110.6 (3) | C22—N5—C28 | 108.0 (3) |
C13—N2—C7 | 108.1 (3) | C28A—N5—C22A | 107.7 (4) |
C7A—N2—C13A | 110.2 (8) | C21A—N5—C22A | 104.3 (4) |
C6A—N2—C13A | 105.9 (7) | C21—N5—Cu2 | 100.2 (3) |
C7A—N2—Cu1 | 110.4 (6) | C28A—N5—Cu2 | 120.5 (4) |
C6A—N2—Cu1 | 99.9 (5) | C22—N5—Cu2 | 108.5 (2) |
C6—N2—Cu1 | 106.7 (2) | C21A—N5—Cu2 | 108.2 (3) |
C13—N2—Cu1 | 118.1 (2) | C28—N5—Cu2 | 113.7 (2) |
C7—N2—Cu1 | 98.7 (2) | C22A—N5—Cu2 | 96.3 (3) |
C13A—N2—Cu1 | 110.8 (5) | N4—C20—C19 | 123.6 (8) |
C1—N1—C5 | 117.2 (5) | N4—C20—C21 | 118.1 (8) |
C1—N1—Cu1 | 125.8 (5) | C19—C20—C21 | 118.2 (9) |
C5—N1—Cu1 | 117.0 (3) | C16—N4—C20 | 114.1 (8) |
N1—C1—C2 | 123.7 (7) | C16—N4—Cu2 | 132.1 (9) |
N1—C1—H1A | 118.1 | C20—N4—Cu2 | 113.6 (7) |
C2—C1—H1A | 118.1 | N4—C16—C17 | 129.1 (13) |
C3—C2—C1 | 117.9 (6) | N4—C16—H16A | 115.5 |
C3—C2—H2A | 121.0 | C17—C16—H16A | 115.5 |
C1—C2—H2A | 121.0 | C16—C17—C18 | 114.9 (12) |
C4—C3—C2 | 119.2 (6) | C16—C17—H17A | 122.5 |
C4—C3—H3A | 120.4 | C18—C17—H17A | 122.5 |
C2—C3—H3A | 120.4 | C19—C18—C17 | 119.3 (10) |
C3—C4—C5 | 120.1 (7) | C19—C18—H18A | 120.4 |
C3—C4—H4A | 120.0 | C17—C18—H18A | 120.4 |
C5—C4—H4A | 120.0 | C18—C19—C20 | 119.0 (11) |
N1—C5—C4 | 121.8 (5) | C18—C19—H19A | 120.5 |
N1—C5—C6 | 117.8 (4) | C20—C19—H19A | 120.5 |
C4—C5—C6 | 120.3 (5) | N4A—C20A—C19A | 120.0 |
N2—C6—C5 | 112.5 (4) | N4A—C20A—C21A | 112.6 (9) |
N2—C6—H6A | 109.1 | C19A—C20A—C21A | 126.4 (8) |
C5—C6—H6A | 109.1 | C20A—N4A—C16A | 120.0 |
N2—C6—H6B | 109.1 | C20A—N4A—Cu2 | 119.7 (7) |
C5—C6—H6B | 109.1 | C16A—N4A—Cu2 | 119.4 (7) |
H6A—C6—H6B | 107.8 | N4A—C16A—C17A | 120.0 |
C8—C7—N2 | 110.7 (3) | N4A—C16A—H16B | 120.0 |
C8—C7—H7A | 109.5 | C17A—C16A—H16B | 120.0 |
N2—C7—H7A | 109.5 | C18A—C17A—C16A | 120.0 |
C8—C7—H7B | 109.5 | C18A—C17A—H17B | 120.0 |
N2—C7—H7B | 109.5 | C16A—C17A—H17B | 120.0 |
H7A—C7—H7B | 108.1 | C17A—C18A—C19A | 120.0 |
N3—C8—C9 | 120.7 (4) | C17A—C18A—H18B | 120.0 |
N3—C8—C7 | 115.8 (4) | C19A—C18A—H18B | 120.0 |
C9—C8—C7 | 123.4 (4) | C18A—C19A—C20A | 120.0 |
C10—C9—C8 | 119.9 (5) | C18A—C19A—H19B | 120.0 |
C10—C9—H9A | 120.0 | C20A—C19A—H19B | 120.0 |
C8—C9—H9A | 120.0 | N5—C21—C20 | 112.1 (6) |
C11—C10—C9 | 119.1 (4) | N5—C21—H21A | 109.2 |
C11—C10—H10A | 120.5 | C20—C21—H21A | 109.2 |
C9—C10—H10A | 120.5 | N5—C21—H21B | 109.2 |
C10—C11—C12 | 117.8 (5) | C20—C21—H21B | 109.2 |
C10—C11—H11A | 121.1 | H21A—C21—H21B | 107.9 |
C12—C11—H11A | 121.1 | N5—C22—C23 | 109.9 (4) |
N3—C12—C11 | 124.8 (5) | N5—C22—H22A | 109.7 |
N3—C12—H12A | 117.6 | C23—C22—H22A | 109.7 |
C11—C12—H12A | 117.6 | N5—C22—H22B | 109.7 |
C12—N3—C8 | 117.6 (4) | C23—C22—H22B | 109.7 |
C12—N3—Cu1 | 127.0 (4) | H22A—C22—H22B | 108.2 |
C8—N3—Cu1 | 114.4 (4) | N6—C23—C24 | 122.0 (7) |
N2—C13—C14 | 108.6 (3) | N6—C23—C22 | 117.4 (6) |
N2—C13—H13A | 110.0 | C24—C23—C22 | 120.4 (5) |
C14—C13—H13A | 110.0 | C25—C24—C23 | 120.6 (10) |
N2—C13—H13B | 110.0 | C25—C24—H24A | 119.7 |
C14—C13—H13B | 110.0 | C23—C24—H24A | 119.7 |
H13A—C13—H13B | 108.3 | C24—C25—C26 | 118.9 (15) |
C2A—C1A—N1A | 120.0 | C24—C25—H25A | 120.5 |
C2A—C1A—H1AA | 120.0 | C26—C25—H25A | 120.5 |
N1A—C1A—H1AA | 120.0 | C27—C26—C25 | 119.1 (12) |
C3A—C2A—C1A | 120.0 | C27—C26—H26A | 120.4 |
C3A—C2A—H2AA | 120.0 | C25—C26—H26A | 120.4 |
C1A—C2A—H2AA | 120.0 | N6—C27—C26 | 122.9 (11) |
C4A—C3A—C2A | 120.0 | N6—C27—H27A | 118.6 |
C4A—C3A—H3AA | 120.0 | C26—C27—H27A | 118.6 |
C2A—C3A—H3AA | 120.0 | C23—N6—C27 | 116.3 (11) |
C3A—C4A—C5A | 120.0 | C23—N6—Cu2 | 117.5 (7) |
C3A—C4A—H4AA | 120.0 | C27—N6—Cu2 | 126.1 (9) |
C5A—C4A—H4AA | 120.0 | C29—C28—N5 | 107.8 (4) |
N1A—C5A—C4A | 120.0 | C29—C28—H28A | 110.1 |
N1A—C5A—C6A | 114.7 (10) | N5—C28—H28A | 110.1 |
C4A—C5A—C6A | 125.0 (10) | C29—C28—H28B | 110.1 |
C5A—N1A—C1A | 120.0 | N5—C28—H28B | 110.1 |
C5A—N1A—Cu1 | 113.7 (8) | H28A—C28—H28B | 108.5 |
C1A—N1A—Cu1 | 124.5 (8) | N5—C21A—C20A | 114.9 (6) |
N2—C6A—C5A | 114.5 (9) | N5—C21A—H21C | 108.5 |
N2—C6A—H6AA | 108.6 | C20A—C21A—H21C | 108.5 |
C5A—C6A—H6AA | 108.6 | N5—C21A—H21D | 108.5 |
N2—C6A—H6AB | 108.6 | C20A—C21A—H21D | 108.5 |
C5A—C6A—H6AB | 108.6 | H21C—C21A—H21D | 107.5 |
H6AA—C6A—H6AB | 107.6 | C23A—C22A—N5 | 108.9 (5) |
N2—C7A—C8A | 108.6 (10) | C23A—C22A—H22C | 109.9 |
N2—C7A—H7AA | 110.0 | N5—C22A—H22C | 109.9 |
C8A—C7A—H7AA | 110.0 | C23A—C22A—H22D | 109.9 |
N2—C7A—H7AB | 110.0 | N5—C22A—H22D | 109.9 |
C8A—C7A—H7AB | 110.0 | H22C—C22A—H22D | 108.3 |
H7AA—C7A—H7AB | 108.4 | N6A—C23A—C24A | 121.6 (11) |
C9A—C8A—N3A | 120.0 | N6A—C23A—C22A | 115.3 (9) |
C9A—C8A—C7A | 121.8 (10) | C24A—C23A—C22A | 123.1 (8) |
N3A—C8A—C7A | 117.2 (10) | C23A—C24A—C25A | 118.8 (13) |
C8A—C9A—C10A | 120.0 | C23A—C24A—H24B | 120.6 |
C8A—C9A—H9AA | 120.0 | C25A—C24A—H24B | 120.6 |
C10A—C9A—H9AA | 120.0 | C26A—C25A—C24A | 118.2 (19) |
C11A—C10A—C9A | 120.0 | C26A—C25A—H25B | 120.9 |
C11A—C10A—H10B | 120.0 | C24A—C25A—H25B | 120.9 |
C9A—C10A—H10B | 120.0 | C25A—C26A—C27A | 118.8 (16) |
C10A—C11A—C12A | 120.0 | C25A—C26A—H26B | 120.6 |
C10A—C11A—H11B | 120.0 | C27A—C26A—H26B | 120.6 |
C12A—C11A—H11B | 120.0 | N6A—C27A—C26A | 123.8 (14) |
C11A—C12A—N3A | 120.0 | N6A—C27A—H27B | 118.1 |
C11A—C12A—H12B | 120.0 | C26A—C27A—H27B | 118.1 |
N3A—C12A—H12B | 120.0 | C23A—N6A—C27A | 118.6 (14) |
C12A—N3A—C8A | 120.0 | C23A—N6A—Cu2 | 114.4 (10) |
C12A—N3A—Cu1 | 124.6 (9) | C27A—N6A—Cu2 | 122.1 (13) |
C8A—N3A—Cu1 | 114.6 (9) | N5—C28A—C29 | 103.0 (5) |
C14—C13A—N2 | 100.2 (7) | N5—C28A—H28C | 111.2 |
C14—C13A—H13C | 111.7 | C29—C28A—H28C | 111.2 |
N2—C13A—H13C | 111.7 | N5—C28A—H28D | 111.2 |
C14—C13A—H13D | 111.7 | C29—C28A—H28D | 111.2 |
N2—C13A—H13D | 111.7 | H28C—C28A—H28D | 109.1 |
H13C—C13A—H13D | 109.5 | C30—C29—C28 | 117.1 (5) |
C15—C14—C13 | 122.3 (4) | C30—C29—C28A | 117.4 (5) |
C15—C14—C13A | 110.1 (6) | C30—C29—H29A | 121.4 |
C15—C14—H14A | 118.9 | C28—C29—H29A | 121.4 |
C13—C14—H14A | 118.9 | C30—C29—H29B | 121.3 |
C15—C14—H14B | 124.9 | C28A—C29—H29B | 121.3 |
C13A—C14—H14B | 124.9 | C29—C30—H30A | 120.0 |
C14—C15—H15A | 120.0 | C29—C30—H30B | 120.0 |
C14—C15—H15B | 120.0 | H30A—C30—H30B | 120.0 |
H15A—C15—H15B | 120.0 | C29—C30—H30C | 120.0 |
C14—C15—H15C | 120.0 | C29—C30—H30D | 120.0 |
C14—C15—H15D | 120.0 | H30C—C30—H30D | 120.0 |
H15C—C15—H15D | 120.0 | H1WB—O1W—H1WA | 123.6 |
N6A—Cu2—N4A | 122.8 (5) | ||
C5—N1—C1—C2 | −1.3 (8) | C19—C20—N4—C16 | −0.4 (15) |
Cu1—N1—C1—C2 | 176.5 (5) | C21—C20—N4—C16 | −176.5 (10) |
N1—C1—C2—C3 | 2.6 (9) | C19—C20—N4—Cu2 | −174.8 (8) |
C1—C2—C3—C4 | −1.5 (10) | C21—C20—N4—Cu2 | 9.1 (11) |
C2—C3—C4—C5 | −0.6 (10) | C20—N4—C16—C17 | −0.2 (17) |
C1—N1—C5—C4 | −0.9 (9) | Cu2—N4—C16—C17 | 172.8 (11) |
Cu1—N1—C5—C4 | −178.9 (5) | N4—C16—C17—C18 | 1.7 (18) |
C1—N1—C5—C6 | 175.5 (5) | C16—C17—C18—C19 | −2.5 (19) |
Cu1—N1—C5—C6 | −2.5 (7) | C17—C18—C19—C20 | 2.1 (19) |
C3—C4—C5—N1 | 1.9 (10) | N4—C20—C19—C18 | −0.5 (17) |
C3—C4—C5—C6 | −174.4 (6) | C21—C20—C19—C18 | 175.6 (12) |
C13—N2—C6—C5 | −161.6 (4) | C19A—C20A—N4A—C16A | 0.0 |
C7—N2—C6—C5 | 76.6 (4) | C21A—C20A—N4A—C16A | 169.3 (10) |
Cu1—N2—C6—C5 | −29.7 (4) | C19A—C20A—N4A—Cu2 | 169.0 (8) |
N1—C5—C6—N2 | 23.6 (7) | C21A—C20A—N4A—Cu2 | −21.7 (10) |
C4—C5—C6—N2 | −159.9 (5) | C20A—N4A—C16A—C17A | 0.0 |
C6—N2—C7—C8 | −157.5 (3) | Cu2—N4A—C16A—C17A | −169.0 (8) |
C13—N2—C7—C8 | 77.6 (4) | N4A—C16A—C17A—C18A | 0.0 |
Cu1—N2—C7—C8 | −45.9 (3) | C16A—C17A—C18A—C19A | 0.0 |
N2—C7—C8—N3 | 43.8 (6) | C17A—C18A—C19A—C20A | 0.0 |
N2—C7—C8—C9 | −138.9 (5) | N4A—C20A—C19A—C18A | 0.0 |
N3—C8—C9—C10 | −0.6 (10) | C21A—C20A—C19A—C18A | −167.7 (12) |
C7—C8—C9—C10 | −177.7 (6) | C22—N5—C21—C20 | 157.8 (5) |
C8—C9—C10—C11 | 0.0 (11) | C28—N5—C21—C20 | −79.0 (6) |
C9—C10—C11—C12 | 0.8 (11) | Cu2—N5—C21—C20 | 40.9 (5) |
C10—C11—C12—N3 | −1.3 (12) | N4—C20—C21—N5 | −38.7 (10) |
C11—C12—N3—C8 | 0.8 (10) | C19—C20—C21—N5 | 144.9 (7) |
C11—C12—N3—Cu1 | −167.2 (6) | C21—N5—C22—C23 | −78.4 (6) |
C9—C8—N3—C12 | 0.2 (9) | C28—N5—C22—C23 | 157.5 (4) |
C7—C8—N3—C12 | 177.5 (6) | Cu2—N5—C22—C23 | 33.8 (5) |
C9—C8—N3—Cu1 | 169.7 (4) | N5—C22—C23—N6 | −27.1 (9) |
C7—C8—N3—Cu1 | −12.9 (6) | N5—C22—C23—C24 | 157.2 (6) |
C6—N2—C13—C14 | 70.4 (4) | N6—C23—C24—C25 | −0.5 (15) |
C7—N2—C13—C14 | −166.4 (3) | C22—C23—C24—C25 | 175.0 (11) |
Cu1—N2—C13—C14 | −55.6 (4) | C23—C24—C25—C26 | −1 (2) |
N1A—C1A—C2A—C3A | 0.0 | C24—C25—C26—C27 | 4 (2) |
C1A—C2A—C3A—C4A | 0.0 | C25—C26—C27—N6 | −5.2 (19) |
C2A—C3A—C4A—C5A | 0.0 | C24—C23—N6—C27 | −0.5 (14) |
C3A—C4A—C5A—N1A | 0.0 | C22—C23—N6—C27 | −176.2 (9) |
C3A—C4A—C5A—C6A | 173.4 (14) | C24—C23—N6—Cu2 | 180.0 (6) |
C4A—C5A—N1A—C1A | 0.0 | C22—C23—N6—Cu2 | 4.3 (10) |
C6A—C5A—N1A—C1A | −174.0 (12) | C26—C27—N6—C23 | 3.4 (17) |
C4A—C5A—N1A—Cu1 | −165.3 (12) | C26—C27—N6—Cu2 | −177.2 (8) |
C6A—C5A—N1A—Cu1 | 20.6 (12) | C21—N5—C28—C29 | 173.0 (4) |
C2A—C1A—N1A—C5A | 0.0 | C22—N5—C28—C29 | −58.9 (5) |
C2A—C1A—N1A—Cu1 | 163.7 (13) | Cu2—N5—C28—C29 | 61.6 (4) |
C7A—N2—C6A—C5A | 155.2 (10) | C28A—N5—C21A—C20A | −162.0 (7) |
C13A—N2—C6A—C5A | −80.1 (11) | C22A—N5—C21A—C20A | 79.3 (8) |
Cu1—N2—C6A—C5A | 35.1 (10) | Cu2—N5—C21A—C20A | −22.4 (8) |
N1A—C5A—C6A—N2 | −41.2 (13) | N4A—C20A—C21A—N5 | 29.3 (9) |
C4A—C5A—C6A—N2 | 145.2 (11) | C19A—C20A—C21A—N5 | −162.2 (7) |
C6A—N2—C7A—C8A | −80.0 (12) | C28A—N5—C22A—C23A | 78.6 (7) |
C13A—N2—C7A—C8A | 157.4 (9) | C21A—N5—C22A—C23A | −156.9 (6) |
Cu1—N2—C7A—C8A | 34.7 (11) | Cu2—N5—C22A—C23A | −46.3 (5) |
N2—C7A—C8A—C9A | 153.1 (10) | N5—C22A—C23A—N6A | 51.5 (9) |
N2—C7A—C8A—N3A | −38.3 (14) | N5—C22A—C23A—C24A | −129.7 (7) |
N3A—C8A—C9A—C10A | 0.0 | N6A—C23A—C24A—C25A | −0.1 (18) |
C7A—C8A—C9A—C10A | 168.3 (15) | C22A—C23A—C24A—C25A | −178.8 (15) |
C8A—C9A—C10A—C11A | 0.0 | C23A—C24A—C25A—C26A | 1 (3) |
C9A—C10A—C11A—C12A | 0.0 | C24A—C25A—C26A—C27A | −4 (3) |
C10A—C11A—C12A—N3A | 0.0 | C25A—C26A—C27A—N6A | 5 (2) |
C11A—C12A—N3A—C8A | 0.0 | C24A—C23A—N6A—C27A | 1.2 (16) |
C11A—C12A—N3A—Cu1 | 169.2 (12) | C22A—C23A—N6A—C27A | 180.0 (11) |
C9A—C8A—N3A—C12A | 0.0 | C24A—C23A—N6A—Cu2 | 157.1 (7) |
C7A—C8A—N3A—C12A | −168.8 (15) | C22A—C23A—N6A—Cu2 | −24.1 (10) |
C9A—C8A—N3A—Cu1 | −170.2 (11) | C26A—C27A—N6A—C23A | −4 (2) |
C7A—C8A—N3A—Cu1 | 20.9 (14) | C26A—C27A—N6A—Cu2 | −157.8 (11) |
C7A—N2—C13A—C14 | −51.5 (10) | C21A—N5—C28A—C29 | 73.4 (6) |
C6A—N2—C13A—C14 | 178.3 (7) | C22A—N5—C28A—C29 | −169.9 (4) |
Cu1—N2—C13A—C14 | 70.9 (7) | Cu2—N5—C28A—C29 | −61.0 (5) |
N2—C13—C14—C15 | −140.7 (4) | N5—C28—C29—C30 | 147.2 (5) |
N2—C13A—C14—C15 | 154.8 (5) | N5—C28A—C29—C30 | −151.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WB···Cl1i | 0.85 | 2.35 | 3.199 (8) | 177 |
O1W—H1WA···Cl2 | 0.86 | 2.16 | 3.027 (8) | 179 |
Symmetry code: (i) x, y−1, z. |
[Cu(C15H17N3)]ClO4·C2H3N | F(000) = 912 |
Mr = 443.37 | Dx = 1.527 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2961 (5) Å | Cell parameters from 9978 reflections |
b = 10.7435 (6) Å | θ = 2.2–29.8° |
c = 17.5025 (9) Å | µ = 1.30 mm−1 |
β = 94.932 (3)° | T = 150 K |
V = 1928.89 (17) Å3 | Rhomboid, grey |
Z = 4 | 0.51 × 0.28 × 0.17 mm |
Bruker SMART APEXII diffractometer | 5517 independent reflections |
Radiation source: fine-focus sealed tube | 4802 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 8.33 pixels mm-1 | θmax = 29.8°, θmin = 2.0° |
φ and ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −15→15 |
Tmin = 0.554, Tmax = 0.807 | l = −24→24 |
27703 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0419P)2 + 1.3152P] where P = (Fo2 + 2Fc2)/3 |
5517 reflections | (Δ/σ)max = 0.001 |
245 parameters | Δρmax = 0.60 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.40952 (2) | 0.28116 (2) | 0.18876 (2) | 0.02180 (7) | |
N1 | 0.35487 (14) | 0.35540 (13) | 0.08578 (8) | 0.0232 (3) | |
N2 | 0.35542 (12) | 0.47632 (12) | 0.22597 (7) | 0.0188 (2) | |
N3 | 0.25255 (13) | 0.24543 (13) | 0.24709 (8) | 0.0213 (3) | |
C1 | 0.38255 (19) | 0.30569 (17) | 0.01841 (10) | 0.0298 (4) | |
H1 | 0.4233 | 0.2263 | 0.0184 | 0.036* | |
C2 | 0.3539 (2) | 0.3658 (2) | −0.05060 (11) | 0.0362 (4) | |
H2 | 0.3731 | 0.3279 | −0.0973 | 0.043* | |
C3 | 0.2969 (2) | 0.4822 (2) | −0.05060 (11) | 0.0389 (5) | |
H3 | 0.2760 | 0.5253 | −0.0974 | 0.047* | |
C4 | 0.27066 (19) | 0.53545 (18) | 0.01861 (11) | 0.0319 (4) | |
H4 | 0.2332 | 0.6162 | 0.0199 | 0.038* | |
C5 | 0.29974 (15) | 0.46931 (15) | 0.08566 (9) | 0.0219 (3) | |
C6 | 0.26267 (15) | 0.51606 (15) | 0.16191 (9) | 0.0225 (3) | |
H6A | 0.2589 | 0.6081 | 0.1607 | 0.027* | |
H6B | 0.1747 | 0.4848 | 0.1706 | 0.027* | |
C7 | 0.29044 (16) | 0.45596 (16) | 0.29639 (9) | 0.0237 (3) | |
H7A | 0.2332 | 0.5277 | 0.3051 | 0.028* | |
H7B | 0.3567 | 0.4498 | 0.3407 | 0.028* | |
C8 | 0.21024 (16) | 0.33811 (16) | 0.29040 (9) | 0.0231 (3) | |
C9 | 0.10020 (18) | 0.32522 (19) | 0.33018 (11) | 0.0323 (4) | |
H9 | 0.0706 | 0.3927 | 0.3592 | 0.039* | |
C10 | 0.0339 (2) | 0.2129 (2) | 0.32709 (13) | 0.0392 (5) | |
H10 | −0.0409 | 0.2020 | 0.3546 | 0.047* | |
C11 | 0.07809 (19) | 0.11698 (19) | 0.28341 (12) | 0.0344 (4) | |
H11 | 0.0345 | 0.0390 | 0.2806 | 0.041* | |
C12 | 0.18699 (17) | 0.13676 (16) | 0.24387 (10) | 0.0259 (3) | |
H12 | 0.2166 | 0.0713 | 0.2133 | 0.031* | |
C13 | 0.46963 (15) | 0.56005 (14) | 0.23791 (9) | 0.0207 (3) | |
H13A | 0.5189 | 0.5569 | 0.1918 | 0.025* | |
H13B | 0.5276 | 0.5286 | 0.2817 | 0.025* | |
C14 | 0.43571 (17) | 0.69412 (16) | 0.25335 (11) | 0.0268 (3) | |
H14 | 0.4363 | 0.7525 | 0.2126 | 0.032* | |
C15 | 0.40412 (19) | 0.73514 (19) | 0.32348 (14) | 0.0381 (5) | |
H15A | 0.3898 | 0.6703 | 0.3620 | 0.046* | |
H15B | 0.3410 | 0.8047 | 0.3232 | 0.046* | |
Cl1 | 0.31067 (4) | 0.91688 (4) | 0.06230 (2) | 0.03084 (10) | |
O1 | 0.20483 (18) | 0.8654 (2) | 0.10057 (11) | 0.0607 (5) | |
O2 | 0.2754 (2) | 0.9252 (3) | −0.01744 (10) | 0.0768 (7) | |
O3 | 0.33879 (19) | 1.03794 (16) | 0.09251 (11) | 0.0543 (4) | |
O4 | 0.4244 (2) | 0.8414 (2) | 0.07888 (14) | 0.0776 (7) | |
N4 | −0.0428 (3) | 0.1619 (3) | 0.63275 (19) | 0.0916 (11) | |
C16 | −0.0056 (3) | 0.2326 (2) | 0.59215 (16) | 0.0504 (6) | |
C17 | 0.0424 (3) | 0.3246 (4) | 0.54240 (18) | 0.0686 (9) | |
H17A | 0.0759 | 0.3960 | 0.5728 | 0.103* | |
H17B | −0.0286 | 0.3519 | 0.5053 | 0.103* | |
H17C | 0.1126 | 0.2887 | 0.5151 | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.02294 (11) | 0.01788 (10) | 0.02509 (11) | 0.00372 (7) | 0.00491 (7) | 0.00274 (7) |
N1 | 0.0275 (7) | 0.0196 (6) | 0.0229 (6) | 0.0009 (5) | 0.0047 (5) | 0.0007 (5) |
N2 | 0.0188 (6) | 0.0170 (6) | 0.0208 (6) | −0.0014 (5) | 0.0023 (5) | −0.0006 (5) |
N3 | 0.0221 (6) | 0.0178 (6) | 0.0240 (6) | −0.0014 (5) | 0.0026 (5) | 0.0004 (5) |
C1 | 0.0373 (9) | 0.0259 (8) | 0.0271 (8) | −0.0005 (7) | 0.0086 (7) | −0.0019 (7) |
C2 | 0.0465 (11) | 0.0391 (11) | 0.0238 (8) | −0.0055 (9) | 0.0079 (7) | −0.0012 (7) |
C3 | 0.0502 (12) | 0.0410 (11) | 0.0249 (8) | −0.0032 (9) | 0.0008 (8) | 0.0098 (8) |
C4 | 0.0382 (10) | 0.0258 (8) | 0.0310 (9) | 0.0011 (7) | −0.0019 (7) | 0.0074 (7) |
C5 | 0.0219 (7) | 0.0183 (7) | 0.0250 (7) | −0.0019 (6) | −0.0004 (6) | 0.0009 (6) |
C6 | 0.0206 (7) | 0.0194 (7) | 0.0271 (7) | 0.0031 (6) | −0.0006 (6) | −0.0017 (6) |
C7 | 0.0270 (8) | 0.0206 (7) | 0.0243 (7) | −0.0041 (6) | 0.0076 (6) | −0.0039 (6) |
C8 | 0.0233 (7) | 0.0220 (7) | 0.0245 (7) | −0.0032 (6) | 0.0041 (6) | −0.0006 (6) |
C9 | 0.0303 (9) | 0.0315 (9) | 0.0370 (9) | −0.0049 (7) | 0.0135 (7) | −0.0066 (8) |
C10 | 0.0344 (10) | 0.0383 (11) | 0.0476 (11) | −0.0123 (8) | 0.0191 (9) | −0.0034 (9) |
C11 | 0.0325 (9) | 0.0291 (9) | 0.0424 (10) | −0.0114 (7) | 0.0072 (8) | 0.0000 (8) |
C12 | 0.0271 (8) | 0.0201 (7) | 0.0302 (8) | −0.0034 (6) | 0.0021 (6) | −0.0010 (6) |
C13 | 0.0198 (7) | 0.0181 (7) | 0.0244 (7) | −0.0018 (5) | 0.0017 (5) | −0.0004 (6) |
C14 | 0.0230 (8) | 0.0183 (7) | 0.0384 (9) | −0.0031 (6) | −0.0011 (7) | −0.0008 (6) |
C15 | 0.0277 (9) | 0.0296 (9) | 0.0590 (13) | −0.0084 (7) | 0.0158 (9) | −0.0159 (9) |
Cl1 | 0.0350 (2) | 0.0286 (2) | 0.0300 (2) | −0.00178 (17) | 0.00879 (16) | −0.00400 (16) |
O1 | 0.0505 (10) | 0.0695 (13) | 0.0646 (11) | −0.0199 (9) | 0.0189 (9) | 0.0112 (10) |
O2 | 0.0803 (14) | 0.124 (2) | 0.0261 (8) | −0.0273 (14) | 0.0027 (8) | −0.0102 (10) |
O3 | 0.0721 (12) | 0.0338 (8) | 0.0570 (10) | −0.0100 (8) | 0.0053 (9) | −0.0107 (7) |
O4 | 0.0690 (13) | 0.0750 (15) | 0.0933 (16) | 0.0398 (12) | 0.0332 (12) | 0.0171 (13) |
N4 | 0.107 (2) | 0.0626 (17) | 0.096 (2) | −0.0386 (16) | −0.0445 (18) | 0.0344 (16) |
C16 | 0.0511 (14) | 0.0400 (12) | 0.0558 (14) | −0.0056 (10) | −0.0210 (11) | 0.0050 (11) |
C17 | 0.0456 (14) | 0.098 (2) | 0.0607 (16) | −0.0108 (15) | −0.0048 (12) | 0.0264 (17) |
Cu1—N1 | 2.0067 (14) | C8—C9 | 1.387 (2) |
Cu1—C15i | 2.0107 (19) | C9—C10 | 1.385 (3) |
Cu1—N3 | 2.0211 (14) | C9—H9 | 0.9500 |
Cu1—C14i | 2.0403 (17) | C10—C11 | 1.384 (3) |
Cu1—N2 | 2.2788 (13) | C10—H10 | 0.9500 |
N1—C1 | 1.347 (2) | C11—C12 | 1.384 (2) |
N1—C5 | 1.349 (2) | C11—H11 | 0.9500 |
N2—C7 | 1.468 (2) | C12—H12 | 0.9500 |
N2—C6 | 1.472 (2) | C13—C14 | 1.512 (2) |
N2—C13 | 1.4810 (19) | C13—H13A | 0.9900 |
N3—C8 | 1.346 (2) | C13—H13B | 0.9900 |
N3—C12 | 1.347 (2) | C14—C15 | 1.369 (3) |
C1—C2 | 1.379 (3) | C14—Cu1ii | 2.0403 (17) |
C1—H1 | 0.9500 | C14—H14 | 0.9500 |
C2—C3 | 1.381 (3) | C15—Cu1ii | 2.0106 (19) |
C2—H2 | 0.9500 | C15—H15A | 0.9900 |
C3—C4 | 1.387 (3) | C15—H15B | 0.9900 |
C3—H3 | 0.9500 | Cl1—O2 | 1.4144 (18) |
C4—C5 | 1.382 (2) | Cl1—O3 | 1.4242 (17) |
C4—H4 | 0.9500 | Cl1—O4 | 1.434 (2) |
C5—C6 | 1.505 (2) | Cl1—O1 | 1.4379 (17) |
C6—H6A | 0.9900 | N4—C16 | 1.129 (4) |
C6—H6B | 0.9900 | C16—C17 | 1.433 (4) |
C7—C8 | 1.510 (2) | C17—H17A | 0.9800 |
C7—H7A | 0.9900 | C17—H17B | 0.9800 |
C7—H7B | 0.9900 | C17—H17C | 0.9800 |
N1—Cu1—C15i | 101.45 (8) | H7A—C7—H7B | 108.1 |
N1—Cu1—N3 | 110.76 (6) | N3—C8—C9 | 121.78 (16) |
C15i—Cu1—N3 | 144.98 (7) | N3—C8—C7 | 117.24 (14) |
N1—Cu1—C14i | 140.80 (7) | C9—C8—C7 | 120.94 (15) |
C15i—Cu1—C14i | 39.50 (8) | C10—C9—C8 | 119.25 (18) |
N3—Cu1—C14i | 106.64 (7) | C10—C9—H9 | 120.4 |
N1—Cu1—N2 | 80.47 (5) | C8—C9—H9 | 120.4 |
C15i—Cu1—N2 | 121.04 (7) | C11—C10—C9 | 119.09 (17) |
N3—Cu1—N2 | 78.74 (5) | C11—C10—H10 | 120.5 |
C14i—Cu1—N2 | 118.65 (6) | C9—C10—H10 | 120.5 |
C1—N1—C5 | 118.62 (15) | C10—C11—C12 | 118.76 (17) |
C1—N1—Cu1 | 124.37 (12) | C10—C11—H11 | 120.6 |
C5—N1—Cu1 | 116.58 (11) | C12—C11—H11 | 120.6 |
C7—N2—C6 | 111.72 (13) | N3—C12—C11 | 122.46 (16) |
C7—N2—C13 | 112.68 (12) | N3—C12—H12 | 118.8 |
C6—N2—C13 | 112.73 (12) | C11—C12—H12 | 118.8 |
C7—N2—Cu1 | 104.06 (9) | N2—C13—C14 | 114.27 (13) |
C6—N2—Cu1 | 101.98 (9) | N2—C13—H13A | 108.7 |
C13—N2—Cu1 | 112.86 (9) | C14—C13—H13A | 108.7 |
C8—N3—C12 | 118.63 (14) | N2—C13—H13B | 108.7 |
C8—N3—Cu1 | 117.09 (11) | C14—C13—H13B | 108.7 |
C12—N3—Cu1 | 124.26 (12) | H13A—C13—H13B | 107.6 |
N1—C1—C2 | 122.37 (18) | C15—C14—C13 | 122.90 (17) |
N1—C1—H1 | 118.8 | C15—C14—Cu1ii | 69.08 (11) |
C2—C1—H1 | 118.8 | C13—C14—Cu1ii | 110.06 (11) |
C1—C2—C3 | 118.89 (18) | C15—C14—H14 | 118.5 |
C1—C2—H2 | 120.6 | C13—C14—H14 | 118.5 |
C3—C2—H2 | 120.6 | Cu1ii—C14—H14 | 90.8 |
C2—C3—C4 | 119.20 (17) | C14—C15—Cu1ii | 71.41 (11) |
C2—C3—H3 | 120.4 | C14—C15—H15A | 116.5 |
C4—C3—H3 | 120.4 | Cu1ii—C15—H15A | 116.5 |
C5—C4—C3 | 119.03 (18) | C14—C15—H15B | 116.5 |
C5—C4—H4 | 120.5 | Cu1ii—C15—H15B | 116.5 |
C3—C4—H4 | 120.5 | H15A—C15—H15B | 113.5 |
N1—C5—C4 | 121.87 (16) | O2—Cl1—O3 | 109.59 (14) |
N1—C5—C6 | 116.11 (14) | O2—Cl1—O4 | 111.79 (15) |
C4—C5—C6 | 121.87 (15) | O3—Cl1—O4 | 107.77 (15) |
N2—C6—C5 | 112.40 (13) | O2—Cl1—O1 | 110.09 (13) |
N2—C6—H6A | 109.1 | O3—Cl1—O1 | 108.44 (12) |
C5—C6—H6A | 109.1 | O4—Cl1—O1 | 109.08 (13) |
N2—C6—H6B | 109.1 | N4—C16—C17 | 178.4 (3) |
C5—C6—H6B | 109.1 | C16—C17—H17A | 109.5 |
H6A—C6—H6B | 107.9 | C16—C17—H17B | 109.5 |
N2—C7—C8 | 110.63 (13) | H17A—C17—H17B | 109.5 |
N2—C7—H7A | 109.5 | C16—C17—H17C | 109.5 |
C8—C7—H7A | 109.5 | H17A—C17—H17C | 109.5 |
N2—C7—H7B | 109.5 | H17B—C17—H17C | 109.5 |
C8—C7—H7B | 109.5 | ||
C5—N1—C1—C2 | −1.5 (3) | C12—N3—C8—C9 | −1.3 (2) |
Cu1—N1—C1—C2 | −173.66 (15) | Cu1—N3—C8—C9 | 177.28 (14) |
N1—C1—C2—C3 | 1.2 (3) | C12—N3—C8—C7 | 176.54 (15) |
C1—C2—C3—C4 | 0.3 (3) | Cu1—N3—C8—C7 | −4.89 (19) |
C2—C3—C4—C5 | −1.4 (3) | N2—C7—C8—N3 | 30.6 (2) |
C1—N1—C5—C4 | 0.3 (2) | N2—C7—C8—C9 | −151.58 (17) |
Cu1—N1—C5—C4 | 173.09 (14) | N3—C8—C9—C10 | 1.8 (3) |
C1—N1—C5—C6 | 175.93 (15) | C7—C8—C9—C10 | −175.95 (19) |
Cu1—N1—C5—C6 | −11.28 (18) | C8—C9—C10—C11 | −0.9 (3) |
C3—C4—C5—N1 | 1.1 (3) | C9—C10—C11—C12 | −0.3 (3) |
C3—C4—C5—C6 | −174.26 (17) | C8—N3—C12—C11 | −0.1 (3) |
C7—N2—C6—C5 | −147.18 (13) | Cu1—N3—C12—C11 | −178.52 (14) |
C13—N2—C6—C5 | 84.73 (16) | C10—C11—C12—N3 | 0.9 (3) |
Cu1—N2—C6—C5 | −36.57 (14) | C7—N2—C13—C14 | −69.43 (18) |
N1—C5—C6—N2 | 35.3 (2) | C6—N2—C13—C14 | 58.16 (18) |
C4—C5—C6—N2 | −149.04 (16) | Cu1—N2—C13—C14 | 173.05 (11) |
C6—N2—C7—C8 | 72.93 (17) | N2—C13—C14—C15 | 78.8 (2) |
C13—N2—C7—C8 | −158.95 (13) | N2—C13—C14—Cu1ii | 156.32 (11) |
Cu1—N2—C7—C8 | −36.35 (15) | C13—C14—C15—Cu1ii | 100.95 (16) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2. |
[CuCl2(C15H17N3)]·CH2Cl2 | F(000) = 932 |
Mr = 458.68 | Dx = 1.546 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3756 (3) Å | Cell parameters from 9541 reflections |
b = 11.0380 (4) Å | θ = 2.5–31.8° |
c = 21.6954 (9) Å | µ = 1.65 mm−1 |
β = 100.749 (1)° | T = 150 K |
V = 1970.54 (13) Å3 | Rhomboid, blue |
Z = 4 | 0.31 × 0.07 × 0.06 mm |
Bruker SMART APEXII diffractometer | 6852 independent reflections |
Radiation source: fine-focus sealed tube | 5778 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 8.33 pixels mm-1 | θmax = 32.7°, θmin = 1.9° |
φ and ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −16→16 |
Tmin = 0.870, Tmax = 0.906 | l = −32→32 |
24724 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0331P)2 + 1.6661P] where P = (Fo2 + 2Fc2)/3 |
6852 reflections | (Δ/σ)max = 0.001 |
217 parameters | Δρmax = 1.33 e Å−3 |
0 restraints | Δρmin = −1.01 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.34016 (2) | 0.33733 (2) | 0.15325 (2) | 0.02093 (5) | |
Cl1 | 0.27627 (6) | 0.51397 (4) | 0.10199 (2) | 0.03532 (10) | |
Cl2 | 0.50436 (5) | 0.40163 (3) | 0.26031 (2) | 0.02295 (8) | |
N1 | 0.13632 (16) | 0.31992 (12) | 0.18776 (7) | 0.0229 (3) | |
N2 | 0.35799 (16) | 0.15602 (12) | 0.17680 (6) | 0.0193 (2) | |
N3 | 0.53041 (17) | 0.29320 (13) | 0.11324 (6) | 0.0226 (3) | |
C1 | 0.00884 (19) | 0.39636 (15) | 0.17976 (8) | 0.0249 (3) | |
H1 | 0.0042 | 0.4603 | 0.1501 | 0.030* | |
C2 | −0.1150 (2) | 0.38486 (16) | 0.21316 (9) | 0.0273 (3) | |
H2 | −0.2041 | 0.4396 | 0.2065 | 0.033* | |
C3 | −0.1075 (2) | 0.29200 (16) | 0.25673 (9) | 0.0278 (3) | |
H3 | −0.1891 | 0.2846 | 0.2816 | 0.033* | |
C4 | 0.0202 (2) | 0.21010 (16) | 0.26365 (8) | 0.0250 (3) | |
H4 | 0.0254 | 0.1442 | 0.2921 | 0.030* | |
C5 | 0.14009 (19) | 0.22653 (14) | 0.22813 (8) | 0.0217 (3) | |
C6 | 0.28549 (19) | 0.14372 (14) | 0.23395 (7) | 0.0214 (3) | |
H6A | 0.3667 | 0.1657 | 0.2716 | 0.026* | |
H6B | 0.2517 | 0.0588 | 0.2386 | 0.026* | |
C7 | 0.53397 (18) | 0.12954 (14) | 0.18688 (7) | 0.0208 (3) | |
H7A | 0.5518 | 0.0409 | 0.1862 | 0.025* | |
H7B | 0.5883 | 0.1611 | 0.2282 | 0.025* | |
C8 | 0.60363 (19) | 0.18920 (14) | 0.13543 (7) | 0.0208 (3) | |
C9 | 0.7351 (2) | 0.14239 (16) | 0.11285 (8) | 0.0266 (3) | |
H9 | 0.7844 | 0.0685 | 0.1288 | 0.032* | |
C10 | 0.7932 (2) | 0.20586 (19) | 0.06633 (9) | 0.0318 (4) | |
H10 | 0.8834 | 0.1759 | 0.0501 | 0.038* | |
C11 | 0.7187 (2) | 0.31286 (19) | 0.04380 (9) | 0.0333 (4) | |
H11 | 0.7573 | 0.3576 | 0.0121 | 0.040* | |
C12 | 0.5870 (2) | 0.35377 (17) | 0.06808 (8) | 0.0282 (3) | |
H12 | 0.5350 | 0.4269 | 0.0523 | 0.034* | |
C13 | 0.2659 (2) | 0.08322 (16) | 0.12335 (8) | 0.0258 (3) | |
H13A | 0.1485 | 0.1005 | 0.1196 | 0.031* | |
H13B | 0.2988 | 0.1101 | 0.0840 | 0.031* | |
C14 | 0.2916 (2) | −0.05088 (16) | 0.12997 (9) | 0.0301 (4) | |
H14 | 0.2551 | −0.0912 | 0.1635 | 0.036* | |
C15 | 0.3623 (3) | −0.1158 (2) | 0.09167 (11) | 0.0415 (5) | |
H15A | 0.3999 | −0.0777 | 0.0578 | 0.050* | |
H15B | 0.3756 | −0.2007 | 0.0979 | 0.050* | |
C16 | 0.9240 (3) | 0.7454 (2) | 0.09385 (11) | 0.0477 (6) | |
H16A | 0.9714 | 0.7801 | 0.1353 | 0.057* | |
H16B | 1.0071 | 0.6926 | 0.0807 | 0.057* | |
Cl3 | 0.75172 (11) | 0.65644 (7) | 0.10123 (4) | 0.0697 (2) | |
Cl4 | 0.87639 (10) | 0.86418 (8) | 0.03914 (3) | 0.06430 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.02180 (9) | 0.01790 (9) | 0.02352 (10) | 0.00296 (7) | 0.00535 (7) | 0.00421 (7) |
Cl1 | 0.0427 (2) | 0.0279 (2) | 0.0370 (2) | 0.01079 (18) | 0.01161 (19) | 0.01457 (17) |
Cl2 | 0.02182 (16) | 0.02201 (17) | 0.02533 (17) | 0.00270 (13) | 0.00520 (13) | −0.00099 (13) |
N1 | 0.0195 (6) | 0.0201 (6) | 0.0284 (7) | 0.0008 (5) | 0.0030 (5) | 0.0001 (5) |
N2 | 0.0189 (5) | 0.0184 (6) | 0.0205 (6) | 0.0009 (5) | 0.0032 (4) | 0.0009 (4) |
N3 | 0.0247 (6) | 0.0220 (6) | 0.0214 (6) | 0.0007 (5) | 0.0051 (5) | 0.0021 (5) |
C1 | 0.0216 (7) | 0.0213 (7) | 0.0302 (8) | 0.0029 (6) | 0.0002 (6) | −0.0019 (6) |
C2 | 0.0193 (7) | 0.0255 (8) | 0.0357 (9) | 0.0022 (6) | 0.0013 (6) | −0.0085 (7) |
C3 | 0.0215 (7) | 0.0281 (8) | 0.0346 (9) | −0.0041 (6) | 0.0076 (6) | −0.0096 (7) |
C4 | 0.0228 (7) | 0.0235 (7) | 0.0297 (8) | −0.0038 (6) | 0.0079 (6) | −0.0037 (6) |
C5 | 0.0193 (6) | 0.0193 (7) | 0.0264 (7) | −0.0006 (5) | 0.0038 (5) | −0.0016 (6) |
C6 | 0.0211 (7) | 0.0197 (7) | 0.0241 (7) | 0.0011 (5) | 0.0059 (5) | 0.0032 (5) |
C7 | 0.0198 (6) | 0.0197 (6) | 0.0228 (7) | 0.0018 (5) | 0.0039 (5) | 0.0015 (5) |
C8 | 0.0212 (7) | 0.0214 (7) | 0.0196 (6) | 0.0001 (5) | 0.0037 (5) | −0.0007 (5) |
C9 | 0.0263 (8) | 0.0284 (8) | 0.0259 (8) | 0.0032 (6) | 0.0072 (6) | −0.0024 (6) |
C10 | 0.0308 (8) | 0.0404 (10) | 0.0270 (8) | 0.0016 (8) | 0.0125 (7) | −0.0034 (7) |
C11 | 0.0372 (9) | 0.0408 (10) | 0.0243 (8) | −0.0019 (8) | 0.0124 (7) | 0.0037 (7) |
C12 | 0.0326 (8) | 0.0285 (8) | 0.0243 (8) | 0.0002 (7) | 0.0074 (6) | 0.0056 (6) |
C13 | 0.0244 (7) | 0.0257 (8) | 0.0251 (7) | −0.0005 (6) | −0.0011 (6) | −0.0024 (6) |
C14 | 0.0346 (9) | 0.0240 (8) | 0.0305 (8) | −0.0040 (7) | 0.0030 (7) | −0.0035 (6) |
C15 | 0.0517 (12) | 0.0328 (10) | 0.0382 (10) | 0.0028 (9) | 0.0036 (9) | −0.0102 (8) |
C16 | 0.0525 (13) | 0.0514 (14) | 0.0369 (11) | 0.0166 (11) | 0.0023 (10) | 0.0000 (10) |
Cl3 | 0.0745 (5) | 0.0508 (4) | 0.0827 (5) | −0.0011 (3) | 0.0116 (4) | −0.0083 (3) |
Cl4 | 0.0738 (4) | 0.0800 (5) | 0.0380 (3) | 0.0240 (4) | 0.0074 (3) | 0.0170 (3) |
Cu1—N1 | 1.9972 (14) | C7—C8 | 1.504 (2) |
Cu1—N3 | 2.0114 (14) | C7—H7A | 0.9900 |
Cu1—N2 | 2.0640 (13) | C7—H7B | 0.9900 |
Cu1—Cl1 | 2.2590 (5) | C8—C9 | 1.386 (2) |
Cu1—Cl2 | 2.5688 (4) | C9—C10 | 1.389 (3) |
N1—C1 | 1.346 (2) | C9—H9 | 0.9500 |
N1—C5 | 1.349 (2) | C10—C11 | 1.382 (3) |
N2—C7 | 1.478 (2) | C10—H10 | 0.9500 |
N2—C6 | 1.485 (2) | C11—C12 | 1.384 (3) |
N2—C13 | 1.500 (2) | C11—H11 | 0.9500 |
N3—C12 | 1.343 (2) | C12—H12 | 0.9500 |
N3—C8 | 1.347 (2) | C13—C14 | 1.499 (2) |
C1—C2 | 1.378 (2) | C13—H13A | 0.9900 |
C1—H1 | 0.9500 | C13—H13B | 0.9900 |
C2—C3 | 1.388 (3) | C14—C15 | 1.318 (3) |
C2—H2 | 0.9500 | C14—H14 | 0.9500 |
C3—C4 | 1.387 (2) | C15—H15A | 0.9500 |
C3—H3 | 0.9500 | C15—H15B | 0.9500 |
C4—C5 | 1.387 (2) | C16—Cl4 | 1.763 (2) |
C4—H4 | 0.9500 | C16—Cl3 | 1.777 (3) |
C5—C6 | 1.509 (2) | C16—H16A | 0.9900 |
C6—H6A | 0.9900 | C16—H16B | 0.9900 |
C6—H6B | 0.9900 | ||
N1—Cu1—N3 | 160.02 (6) | C5—C6—H6B | 109.9 |
N1—Cu1—N2 | 80.87 (5) | H6A—C6—H6B | 108.3 |
N3—Cu1—N2 | 81.11 (5) | N2—C7—C8 | 108.52 (12) |
N1—Cu1—Cl1 | 97.30 (4) | N2—C7—H7A | 110.0 |
N3—Cu1—Cl1 | 97.50 (4) | C8—C7—H7A | 110.0 |
N2—Cu1—Cl1 | 163.41 (4) | N2—C7—H7B | 110.0 |
N1—Cu1—Cl2 | 92.21 (4) | C8—C7—H7B | 110.0 |
N3—Cu1—Cl2 | 97.09 (4) | H7A—C7—H7B | 108.4 |
N2—Cu1—Cl2 | 92.42 (4) | N3—C8—C9 | 122.01 (15) |
Cl1—Cu1—Cl2 | 104.146 (18) | N3—C8—C7 | 115.11 (13) |
C1—N1—C5 | 118.97 (15) | C9—C8—C7 | 122.88 (15) |
C1—N1—Cu1 | 127.17 (12) | C8—C9—C10 | 118.54 (17) |
C5—N1—Cu1 | 113.50 (10) | C8—C9—H9 | 120.7 |
C7—N2—C6 | 114.21 (12) | C10—C9—H9 | 120.7 |
C7—N2—C13 | 111.28 (12) | C11—C10—C9 | 119.48 (17) |
C6—N2—C13 | 111.42 (12) | C11—C10—H10 | 120.3 |
C7—N2—Cu1 | 104.62 (9) | C9—C10—H10 | 120.3 |
C6—N2—Cu1 | 105.86 (9) | C10—C11—C12 | 118.92 (17) |
C13—N2—Cu1 | 108.96 (10) | C10—C11—H11 | 120.5 |
C12—N3—C8 | 119.05 (15) | C12—C11—H11 | 120.5 |
C12—N3—Cu1 | 127.58 (12) | N3—C12—C11 | 122.00 (17) |
C8—N3—Cu1 | 113.36 (11) | N3—C12—H12 | 119.0 |
N1—C1—C2 | 122.10 (16) | C11—C12—H12 | 119.0 |
N1—C1—H1 | 118.9 | C14—C13—N2 | 114.27 (14) |
C2—C1—H1 | 118.9 | C14—C13—H13A | 108.7 |
C1—C2—C3 | 118.89 (16) | N2—C13—H13A | 108.7 |
C1—C2—H2 | 120.6 | C14—C13—H13B | 108.7 |
C3—C2—H2 | 120.6 | N2—C13—H13B | 108.7 |
C4—C3—C2 | 119.44 (16) | H13A—C13—H13B | 107.6 |
C4—C3—H3 | 120.3 | C15—C14—C13 | 123.34 (19) |
C2—C3—H3 | 120.3 | C15—C14—H14 | 118.3 |
C3—C4—C5 | 118.56 (16) | C13—C14—H14 | 118.3 |
C3—C4—H4 | 120.7 | C14—C15—H15A | 120.0 |
C5—C4—H4 | 120.7 | C14—C15—H15B | 120.0 |
N1—C5—C4 | 121.93 (15) | H15A—C15—H15B | 120.0 |
N1—C5—C6 | 115.97 (14) | Cl4—C16—Cl3 | 112.71 (13) |
C4—C5—C6 | 122.07 (15) | Cl4—C16—H16A | 109.1 |
N2—C6—C5 | 108.91 (12) | Cl3—C16—H16A | 109.1 |
N2—C6—H6A | 109.9 | Cl4—C16—H16B | 109.1 |
C5—C6—H6A | 109.9 | Cl3—C16—H16B | 109.1 |
N2—C6—H6B | 109.9 | H16A—C16—H16B | 107.8 |
C5—N1—C1—C2 | 2.4 (2) | Cu1—N2—C7—C8 | −43.26 (13) |
Cu1—N1—C1—C2 | −170.21 (13) | C12—N3—C8—C9 | −0.4 (2) |
N1—C1—C2—C3 | 0.4 (3) | Cu1—N3—C8—C9 | 178.74 (13) |
C1—C2—C3—C4 | −2.8 (2) | C12—N3—C8—C7 | 178.67 (15) |
C2—C3—C4—C5 | 2.3 (2) | Cu1—N3—C8—C7 | −2.23 (17) |
C1—N1—C5—C4 | −2.9 (2) | N2—C7—C8—N3 | 31.65 (18) |
Cu1—N1—C5—C4 | 170.69 (12) | N2—C7—C8—C9 | −149.33 (15) |
C1—N1—C5—C6 | 179.16 (14) | N3—C8—C9—C10 | 0.6 (3) |
Cu1—N1—C5—C6 | −7.25 (18) | C7—C8—C9—C10 | −178.36 (16) |
C3—C4—C5—N1 | 0.5 (2) | C8—C9—C10—C11 | −0.2 (3) |
C3—C4—C5—C6 | 178.35 (15) | C9—C10—C11—C12 | −0.3 (3) |
C7—N2—C6—C5 | 152.60 (13) | C8—N3—C12—C11 | −0.2 (3) |
C13—N2—C6—C5 | −80.27 (15) | Cu1—N3—C12—C11 | −179.20 (14) |
Cu1—N2—C6—C5 | 38.05 (14) | C10—C11—C12—N3 | 0.6 (3) |
N1—C5—C6—N2 | −21.73 (19) | C7—N2—C13—C14 | 55.61 (19) |
C4—C5—C6—N2 | 160.33 (14) | C6—N2—C13—C14 | −73.10 (18) |
C6—N2—C7—C8 | −158.54 (13) | Cu1—N2—C13—C14 | 170.46 (12) |
C13—N2—C7—C8 | 74.25 (16) | N2—C13—C14—C15 | −115.3 (2) |
[CuCl(C15H17N3)]ClO4 | F(000) = 892 |
Mr = 437.76 | Dx = 1.696 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4260 (12) Å | Cell parameters from 4302 reflections |
b = 14.832 (2) Å | θ = 2.7–30.1° |
c = 14.007 (2) Å | µ = 1.61 mm−1 |
β = 101.677 (2)° | T = 150 K |
V = 1714.3 (4) Å3 | Rhomboid, blue |
Z = 4 | 0.25 × 0.20 × 0.06 mm |
Bruker SMART APEXII diffractometer | 5553 independent reflections |
Radiation source: fine-focus sealed tube | 4766 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
Detector resolution: 8.33 pixels mm-1 | θmax = 32.6°, θmin = 2.8° |
φ and ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −21→21 |
Tmin = 0.620, Tmax = 0.881 | l = −21→21 |
10763 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.051P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.098 | (Δ/σ)max = 0.002 |
S = 0.98 | Δρmax = 0.93 e Å−3 |
5553 reflections | Δρmin = −0.64 e Å−3 |
226 parameters | Absolute structure: Flack x determined using 1902 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
2 restraints | Absolute structure parameter: −0.005 (8) |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.66284 (4) | 0.72310 (3) | 0.72527 (3) | 0.02040 (12) | |
Cl1 | 0.76060 (14) | 0.58664 (7) | 0.76668 (9) | 0.0313 (2) | |
N1 | 0.4650 (4) | 0.7138 (2) | 0.7820 (3) | 0.0226 (7) | |
N2 | 0.5842 (4) | 0.8531 (2) | 0.6986 (2) | 0.0186 (6) | |
N3 | 0.8353 (4) | 0.7649 (2) | 0.6587 (2) | 0.0216 (7) | |
C1 | 0.3905 (6) | 0.6378 (3) | 0.7988 (3) | 0.0290 (9) | |
H1 | 0.4400 | 0.5815 | 0.7908 | 0.035* | |
C2 | 0.2443 (6) | 0.6391 (4) | 0.8275 (4) | 0.0332 (10) | |
H2 | 0.1925 | 0.5842 | 0.8381 | 0.040* | |
C3 | 0.1725 (6) | 0.7206 (3) | 0.8411 (3) | 0.0315 (10) | |
H3 | 0.0716 | 0.7224 | 0.8615 | 0.038* | |
C4 | 0.2505 (5) | 0.8002 (3) | 0.8244 (3) | 0.0278 (9) | |
H4 | 0.2042 | 0.8572 | 0.8330 | 0.033* | |
C5 | 0.3970 (5) | 0.7939 (3) | 0.7948 (3) | 0.0228 (8) | |
C6 | 0.4969 (5) | 0.8748 (3) | 0.7773 (3) | 0.0223 (8) | |
H6A | 0.4253 | 0.9275 | 0.7584 | 0.027* | |
H6B | 0.5755 | 0.8901 | 0.8378 | 0.027* | |
C7 | 0.7305 (5) | 0.9084 (3) | 0.6999 (3) | 0.0229 (8) | |
H7A | 0.7859 | 0.9209 | 0.7679 | 0.027* | |
H7B | 0.7006 | 0.9665 | 0.6664 | 0.027* | |
C8 | 0.8414 (5) | 0.8552 (3) | 0.6475 (3) | 0.0225 (8) | |
C9 | 0.9431 (6) | 0.8942 (4) | 0.5936 (4) | 0.0326 (10) | |
H9 | 0.9477 | 0.9579 | 0.5878 | 0.039* | |
C10 | 1.0386 (6) | 0.8394 (4) | 0.5482 (4) | 0.0377 (12) | |
H10 | 1.1074 | 0.8650 | 0.5094 | 0.045* | |
C11 | 1.0321 (6) | 0.7478 (4) | 0.5600 (4) | 0.0355 (11) | |
H11 | 1.0970 | 0.7091 | 0.5297 | 0.043* | |
C12 | 0.9305 (5) | 0.7127 (3) | 0.6163 (3) | 0.0289 (9) | |
H12 | 0.9280 | 0.6492 | 0.6252 | 0.035* | |
C13 | 0.4719 (5) | 0.8569 (3) | 0.6009 (3) | 0.0227 (8) | |
H13A | 0.5310 | 0.8357 | 0.5508 | 0.027* | |
H13B | 0.3810 | 0.8146 | 0.6011 | 0.027* | |
C14 | 0.4033 (6) | 0.9487 (3) | 0.5723 (3) | 0.0273 (9) | |
H14 | 0.3364 | 0.9763 | 0.6110 | 0.033* | |
C15 | 0.4322 (7) | 0.9929 (4) | 0.4953 (3) | 0.0401 (12) | |
H15A | 0.4988 | 0.9666 | 0.4557 | 0.048* | |
H15B | 0.3864 | 1.0509 | 0.4798 | 0.048* | |
Cl2 | 0.41399 (12) | 0.63022 (7) | 0.47752 (8) | 0.0252 (2) | |
O1 | 0.4560 (8) | 0.5597 (4) | 0.4223 (3) | 0.0767 (18) | |
O2 | 0.3144 (10) | 0.6004 (6) | 0.5373 (8) | 0.171 (5) | |
O3 | 0.5608 (8) | 0.6629 (4) | 0.5360 (5) | 0.107 (3) | |
O4 | 0.3369 (4) | 0.7032 (2) | 0.4174 (3) | 0.0319 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0192 (2) | 0.0176 (2) | 0.0244 (2) | 0.0038 (2) | 0.00465 (16) | 0.0018 (2) |
Cl1 | 0.0371 (6) | 0.0222 (5) | 0.0361 (6) | 0.0127 (4) | 0.0108 (5) | 0.0074 (4) |
N1 | 0.0176 (16) | 0.0248 (18) | 0.0248 (17) | 0.0012 (13) | 0.0028 (13) | −0.0010 (14) |
N2 | 0.0159 (14) | 0.0196 (16) | 0.0192 (15) | 0.0014 (12) | 0.0007 (12) | −0.0001 (13) |
N3 | 0.0173 (16) | 0.0254 (18) | 0.0209 (17) | 0.0017 (13) | 0.0012 (13) | 0.0017 (13) |
C1 | 0.029 (2) | 0.025 (2) | 0.034 (2) | −0.0020 (17) | 0.0077 (18) | 0.0004 (18) |
C2 | 0.028 (2) | 0.036 (3) | 0.037 (3) | −0.0057 (19) | 0.011 (2) | 0.000 (2) |
C3 | 0.023 (2) | 0.046 (3) | 0.026 (2) | 0.0020 (19) | 0.0073 (17) | −0.002 (2) |
C4 | 0.0214 (19) | 0.036 (2) | 0.025 (2) | 0.0091 (17) | 0.0026 (16) | −0.0045 (17) |
C5 | 0.023 (2) | 0.0229 (19) | 0.0209 (19) | 0.0036 (15) | 0.0006 (15) | −0.0011 (15) |
C6 | 0.026 (2) | 0.020 (2) | 0.0199 (18) | 0.0064 (16) | 0.0022 (15) | −0.0036 (15) |
C7 | 0.0191 (18) | 0.0215 (19) | 0.0253 (19) | −0.0009 (15) | −0.0020 (15) | 0.0014 (15) |
C8 | 0.0165 (17) | 0.029 (2) | 0.0195 (18) | −0.0016 (15) | −0.0019 (14) | 0.0020 (16) |
C9 | 0.026 (2) | 0.036 (3) | 0.034 (2) | −0.0020 (18) | 0.0013 (18) | 0.0131 (19) |
C10 | 0.020 (2) | 0.064 (4) | 0.028 (2) | −0.003 (2) | 0.0036 (17) | 0.008 (2) |
C11 | 0.026 (2) | 0.051 (3) | 0.029 (2) | 0.003 (2) | 0.0044 (18) | 0.000 (2) |
C12 | 0.021 (2) | 0.036 (2) | 0.029 (2) | 0.0034 (17) | 0.0042 (17) | −0.0029 (18) |
C13 | 0.0229 (19) | 0.0215 (19) | 0.0212 (18) | 0.0027 (15) | −0.0013 (15) | −0.0028 (15) |
C14 | 0.030 (2) | 0.024 (2) | 0.024 (2) | 0.0081 (17) | −0.0038 (17) | −0.0019 (16) |
C15 | 0.060 (4) | 0.032 (3) | 0.023 (2) | 0.003 (2) | −0.003 (2) | 0.005 (2) |
Cl2 | 0.0280 (5) | 0.0224 (4) | 0.0248 (4) | 0.0025 (4) | 0.0041 (4) | 0.0011 (3) |
O1 | 0.113 (4) | 0.061 (3) | 0.044 (3) | 0.041 (3) | −0.011 (3) | −0.021 (2) |
O2 | 0.140 (6) | 0.137 (6) | 0.290 (11) | 0.107 (6) | 0.169 (8) | 0.169 (7) |
O3 | 0.107 (5) | 0.050 (3) | 0.122 (5) | 0.016 (3) | −0.080 (4) | −0.016 (3) |
O4 | 0.0277 (16) | 0.0264 (16) | 0.0375 (18) | 0.0013 (13) | −0.0033 (14) | 0.0073 (14) |
Cu1—N3 | 1.979 (4) | C7—C8 | 1.520 (6) |
Cu1—N1 | 1.991 (4) | C7—H7A | 0.9900 |
Cu1—N2 | 2.048 (3) | C7—H7B | 0.9900 |
Cu1—Cl1 | 2.2176 (11) | C8—C9 | 1.379 (6) |
N1—C1 | 1.333 (6) | C9—C10 | 1.386 (8) |
N1—C5 | 1.346 (5) | C9—H9 | 0.9500 |
N2—C6 | 1.480 (5) | C10—C11 | 1.371 (9) |
N2—C7 | 1.478 (5) | C10—H10 | 0.9500 |
N2—C13 | 1.498 (5) | C11—C12 | 1.379 (7) |
N3—C12 | 1.338 (6) | C11—H11 | 0.9500 |
N3—C8 | 1.350 (6) | C12—H12 | 0.9500 |
C1—C2 | 1.372 (7) | C13—C14 | 1.502 (6) |
C1—H1 | 0.9500 | C13—H13A | 0.9900 |
C2—C3 | 1.382 (7) | C13—H13B | 0.9900 |
C2—H2 | 0.9500 | C14—C15 | 1.326 (7) |
C3—C4 | 1.393 (7) | C14—H14 | 0.9500 |
C3—H3 | 0.9500 | C15—H15A | 0.9500 |
C4—C5 | 1.382 (6) | C15—H15B | 0.9500 |
C4—H4 | 0.9500 | Cl2—O2 | 1.372 (6) |
C5—C6 | 1.515 (6) | Cl2—O1 | 1.388 (5) |
C6—H6A | 0.9900 | Cl2—O3 | 1.423 (5) |
C6—H6B | 0.9900 | Cl2—O4 | 1.443 (3) |
N3—Cu1—N1 | 164.53 (15) | N2—C7—C8 | 107.4 (3) |
N3—Cu1—N2 | 81.96 (14) | N2—C7—H7A | 110.2 |
N1—Cu1—N2 | 82.65 (14) | C8—C7—H7A | 110.2 |
N3—Cu1—Cl1 | 98.06 (11) | N2—C7—H7B | 110.2 |
N1—Cu1—Cl1 | 97.42 (11) | C8—C7—H7B | 110.2 |
N2—Cu1—Cl1 | 174.94 (10) | H7A—C7—H7B | 108.5 |
C1—N1—C5 | 119.6 (4) | N3—C8—C9 | 121.5 (4) |
C1—N1—Cu1 | 126.2 (3) | N3—C8—C7 | 114.7 (4) |
C5—N1—Cu1 | 113.9 (3) | C9—C8—C7 | 123.8 (4) |
C6—N2—C7 | 114.1 (3) | C8—C9—C10 | 119.2 (5) |
C6—N2—C13 | 110.8 (3) | C8—C9—H9 | 120.4 |
C7—N2—C13 | 111.2 (3) | C10—C9—H9 | 120.4 |
C6—N2—Cu1 | 105.1 (2) | C11—C10—C9 | 119.0 (5) |
C7—N2—Cu1 | 106.3 (2) | C11—C10—H10 | 120.5 |
C13—N2—Cu1 | 108.9 (2) | C9—C10—H10 | 120.5 |
C12—N3—C8 | 118.9 (4) | C10—C11—C12 | 119.2 (5) |
C12—N3—Cu1 | 126.2 (3) | C10—C11—H11 | 120.4 |
C8—N3—Cu1 | 114.5 (3) | C12—C11—H11 | 120.4 |
N1—C1—C2 | 121.5 (4) | N3—C12—C11 | 122.2 (5) |
N1—C1—H1 | 119.2 | N3—C12—H12 | 118.9 |
C2—C1—H1 | 119.2 | C11—C12—H12 | 118.9 |
C1—C2—C3 | 119.8 (5) | C14—C13—N2 | 114.5 (3) |
C1—C2—H2 | 120.1 | C14—C13—H13A | 108.6 |
C3—C2—H2 | 120.1 | N2—C13—H13A | 108.6 |
C2—C3—C4 | 118.9 (4) | C14—C13—H13B | 108.6 |
C2—C3—H3 | 120.6 | N2—C13—H13B | 108.6 |
C4—C3—H3 | 120.6 | H13A—C13—H13B | 107.6 |
C5—C4—C3 | 118.3 (4) | C15—C14—C13 | 122.8 (5) |
C5—C4—H4 | 120.9 | C15—C14—H14 | 118.6 |
C3—C4—H4 | 120.9 | C13—C14—H14 | 118.6 |
N1—C5—C4 | 122.0 (4) | C14—C15—H15A | 120.0 |
N1—C5—C6 | 114.4 (4) | C14—C15—H15B | 120.0 |
C4—C5—C6 | 123.6 (4) | H15A—C15—H15B | 120.0 |
N2—C6—C5 | 108.9 (3) | O2—Cl2—O1 | 110.6 (5) |
N2—C6—H6A | 109.9 | O2—Cl2—O3 | 109.1 (7) |
C5—C6—H6A | 109.9 | O1—Cl2—O3 | 106.7 (4) |
N2—C6—H6B | 109.9 | O2—Cl2—O4 | 109.8 (3) |
C5—C6—H6B | 109.9 | O1—Cl2—O4 | 112.1 (3) |
H6A—C6—H6B | 108.3 | O3—Cl2—O4 | 108.5 (3) |
C5—N1—C1—C2 | 1.1 (7) | Cu1—N2—C7—C8 | 40.9 (3) |
Cu1—N1—C1—C2 | −172.3 (4) | C12—N3—C8—C9 | 0.0 (6) |
N1—C1—C2—C3 | −1.1 (8) | Cu1—N3—C8—C9 | −173.1 (3) |
C1—C2—C3—C4 | 0.5 (7) | C12—N3—C8—C7 | −179.1 (4) |
C2—C3—C4—C5 | 0.0 (7) | Cu1—N3—C8—C7 | 7.9 (4) |
C1—N1—C5—C4 | −0.6 (6) | N2—C7—C8—N3 | −33.3 (4) |
Cu1—N1—C5—C4 | 173.6 (3) | N2—C7—C8—C9 | 147.6 (4) |
C1—N1—C5—C6 | 177.6 (4) | N3—C8—C9—C10 | 1.4 (6) |
Cu1—N1—C5—C6 | −8.2 (4) | C7—C8—C9—C10 | −179.6 (4) |
C3—C4—C5—N1 | 0.1 (6) | C8—C9—C10—C11 | −1.6 (7) |
C3—C4—C5—C6 | −178.0 (4) | C9—C10—C11—C12 | 0.3 (7) |
C7—N2—C6—C5 | −157.0 (3) | C8—N3—C12—C11 | −1.3 (6) |
C13—N2—C6—C5 | 76.5 (4) | Cu1—N3—C12—C11 | 170.8 (3) |
Cu1—N2—C6—C5 | −40.9 (3) | C10—C11—C12—N3 | 1.2 (7) |
N1—C5—C6—N2 | 34.0 (5) | C6—N2—C13—C14 | 64.3 (5) |
C4—C5—C6—N2 | −147.9 (4) | C7—N2—C13—C14 | −63.7 (5) |
C6—N2—C7—C8 | 156.3 (3) | Cu1—N2—C13—C14 | 179.4 (3) |
C13—N2—C7—C8 | −77.5 (4) | N2—C13—C14—C15 | 117.2 (5) |
[Cu2Cl2(C15H17N3)2](C24H20B)2 | F(000) = 1372 |
Mr = 1315.05 | Dx = 1.318 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3914 (2) Å | Cell parameters from 9988 reflections |
b = 12.2672 (3) Å | θ = 2.6–26.7° |
c = 26.0083 (6) Å | µ = 0.77 mm−1 |
β = 91.485 (1)° | T = 150 K |
V = 3314.25 (13) Å3 | Rhomboid, blue |
Z = 2 | 0.52 × 0.22 × 0.21 mm |
Bruker SMART APEXII diffractometer | 7079 independent reflections |
Radiation source: fine-focus sealed tube | 6006 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.8°, θmin = 1.6° |
φ and ω scans | h = −13→13 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −15→15 |
Tmin = 0.691, Tmax = 0.853 | l = −32→32 |
42327 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.048P)2 + 1.3734P] where P = (Fo2 + 2Fc2)/3 |
7079 reflections | (Δ/σ)max = 0.001 |
425 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
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. Disorder in the terminal ethylinic group was observed. C14 and C15 were modeled over two sites, rotated by approximately 180°. The two sites were refined with occupancies summed to unity yielding a 0.738:0.262 ratio. All atoms were refined with anisotropic displacement parameters and the pairs of atoms restrained to have similar displacement parameters. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cu1 | 0.58967 (2) | 0.96826 (2) | 0.05495 (2) | 0.02885 (8) | |
Cl1 | 0.34988 (4) | 0.93929 (4) | 0.01632 (2) | 0.03497 (11) | |
N1 | 0.65150 (13) | 0.82020 (13) | 0.03516 (5) | 0.0312 (3) | |
N2 | 0.56575 (14) | 0.89354 (13) | 0.12426 (5) | 0.0299 (3) | |
N3 | 0.53381 (13) | 1.09774 (13) | 0.09560 (5) | 0.0302 (3) | |
C1 | 0.72573 (17) | 0.79565 (17) | −0.00488 (7) | 0.0371 (4) | |
H1 | 0.7425 | 0.8506 | −0.0295 | 0.045* | |
C2 | 0.77808 (19) | 0.69374 (19) | −0.01133 (8) | 0.0440 (5) | |
H2 | 0.8295 | 0.6785 | −0.0401 | 0.053* | |
C3 | 0.7549 (2) | 0.61374 (19) | 0.02473 (8) | 0.0458 (5) | |
H3 | 0.7909 | 0.5430 | 0.0212 | 0.055* | |
C4 | 0.67835 (19) | 0.63819 (17) | 0.06611 (8) | 0.0414 (4) | |
H4 | 0.6608 | 0.5844 | 0.0913 | 0.050* | |
C5 | 0.62796 (17) | 0.74222 (16) | 0.07010 (7) | 0.0333 (4) | |
C6 | 0.54168 (19) | 0.77695 (16) | 0.11276 (7) | 0.0370 (4) | |
H6A | 0.4504 | 0.7662 | 0.1021 | 0.044* | |
H6B | 0.5598 | 0.7324 | 0.1438 | 0.044* | |
C7 | 0.45336 (17) | 0.94942 (16) | 0.14641 (7) | 0.0331 (4) | |
H7A | 0.4484 | 0.9330 | 0.1836 | 0.040* | |
H7B | 0.3727 | 0.9246 | 0.1290 | 0.040* | |
C8 | 0.47144 (16) | 1.06948 (16) | 0.13837 (6) | 0.0305 (4) | |
C9 | 0.42605 (17) | 1.14717 (17) | 0.17211 (7) | 0.0359 (4) | |
H9 | 0.3807 | 1.1258 | 0.2017 | 0.043* | |
C10 | 0.44771 (19) | 1.25541 (18) | 0.16205 (7) | 0.0413 (5) | |
H10 | 0.4179 | 1.3099 | 0.1848 | 0.050* | |
C11 | 0.5132 (2) | 1.28447 (17) | 0.11852 (8) | 0.0433 (5) | |
H11 | 0.5298 | 1.3590 | 0.1112 | 0.052* | |
C12 | 0.55404 (18) | 1.20365 (16) | 0.08596 (7) | 0.0372 (4) | |
H12 | 0.5979 | 1.2236 | 0.0558 | 0.045* | |
C13 | 0.68103 (18) | 0.90759 (19) | 0.16005 (7) | 0.0419 (5) | |
H13A | 0.6879 | 0.8437 | 0.1832 | 0.050* | 0.738 (10) |
H13B | 0.6687 | 0.9732 | 0.1815 | 0.050* | 0.738 (10) |
H13C | 0.6990 | 0.9865 | 0.1635 | 0.050* | 0.262 (10) |
H13D | 0.6581 | 0.8803 | 0.1944 | 0.050* | 0.262 (10) |
C14 | 0.8046 (3) | 0.9192 (4) | 0.13113 (12) | 0.0387 (10) | 0.738 (10) |
H14 | 0.8149 | 0.9815 | 0.1099 | 0.046* | 0.738 (10) |
C15 | 0.8975 (4) | 0.8485 (5) | 0.13370 (18) | 0.0578 (12) | 0.738 (10) |
H15A | 0.8898 | 0.7854 | 0.1546 | 0.069* | 0.738 (10) |
H15B | 0.9732 | 0.8598 | 0.1147 | 0.069* | 0.738 (10) |
C14A | 0.8025 (8) | 0.8517 (11) | 0.1445 (3) | 0.038 (3) | 0.262 (10) |
H14A | 0.8108 | 0.7746 | 0.1442 | 0.046* | 0.262 (10) |
C15A | 0.8925 (14) | 0.9139 (16) | 0.1319 (5) | 0.067 (4) | 0.262 (10) |
H15C | 0.8809 | 0.9906 | 0.1327 | 0.080* | 0.262 (10) |
H15D | 0.9722 | 0.8840 | 0.1216 | 0.080* | 0.262 (10) |
B1 | 0.04320 (18) | 0.40952 (16) | 0.16838 (7) | 0.0262 (4) | |
C16 | 0.13424 (15) | 0.37492 (14) | 0.21864 (6) | 0.0262 (3) | |
C17 | 0.11036 (19) | 0.27900 (15) | 0.24593 (7) | 0.0350 (4) | |
H17 | 0.0385 | 0.2356 | 0.2356 | 0.042* | |
C18 | 0.1870 (2) | 0.24432 (17) | 0.28740 (7) | 0.0463 (5) | |
H18 | 0.1678 | 0.1779 | 0.3044 | 0.056* | |
C19 | 0.2912 (2) | 0.3065 (2) | 0.30394 (7) | 0.0507 (6) | |
H19 | 0.3458 | 0.2821 | 0.3315 | 0.061* | |
C20 | 0.31481 (18) | 0.4043 (2) | 0.27997 (7) | 0.0450 (5) | |
H20 | 0.3839 | 0.4492 | 0.2918 | 0.054* | |
C21 | 0.23715 (17) | 0.43764 (16) | 0.23815 (6) | 0.0326 (4) | |
H21 | 0.2549 | 0.5056 | 0.2223 | 0.039* | |
C22 | 0.01424 (15) | 0.30275 (15) | 0.13123 (6) | 0.0277 (4) | |
C23 | 0.08903 (17) | 0.20775 (15) | 0.13197 (7) | 0.0329 (4) | |
H23 | 0.1565 | 0.2017 | 0.1572 | 0.039* | |
C24 | 0.0696 (2) | 0.12159 (17) | 0.09762 (7) | 0.0409 (4) | |
H24 | 0.1226 | 0.0586 | 0.0999 | 0.049* | |
C25 | −0.0272 (2) | 0.12823 (18) | 0.06021 (7) | 0.0431 (5) | |
H25 | −0.0414 | 0.0701 | 0.0366 | 0.052* | |
C26 | −0.10279 (18) | 0.22065 (18) | 0.05772 (7) | 0.0394 (5) | |
H26 | −0.1694 | 0.2262 | 0.0321 | 0.047* | |
C27 | −0.08229 (17) | 0.30590 (17) | 0.09238 (6) | 0.0334 (4) | |
H27 | −0.1357 | 0.3686 | 0.0897 | 0.040* | |
C28 | −0.08922 (16) | 0.46261 (14) | 0.19156 (6) | 0.0278 (4) | |
C29 | −0.20598 (17) | 0.40643 (17) | 0.19516 (7) | 0.0352 (4) | |
H29 | −0.2118 | 0.3341 | 0.1823 | 0.042* | |
C30 | −0.31405 (19) | 0.45312 (19) | 0.21704 (8) | 0.0444 (5) | |
H30 | −0.3915 | 0.4123 | 0.2189 | 0.053* | |
C31 | −0.3093 (2) | 0.55789 (19) | 0.23598 (8) | 0.0472 (5) | |
H31 | −0.3833 | 0.5900 | 0.2504 | 0.057* | |
C32 | −0.1952 (2) | 0.61582 (17) | 0.23374 (8) | 0.0436 (5) | |
H32 | −0.1903 | 0.6879 | 0.2470 | 0.052* | |
C33 | −0.08759 (19) | 0.56819 (16) | 0.21206 (7) | 0.0348 (4) | |
H33 | −0.0100 | 0.6090 | 0.2112 | 0.042* | |
C34 | 0.11517 (16) | 0.49713 (15) | 0.13066 (6) | 0.0280 (3) | |
C35 | 0.05047 (19) | 0.58030 (17) | 0.10391 (7) | 0.0373 (4) | |
H35 | −0.0386 | 0.5908 | 0.1097 | 0.045* | |
C36 | 0.1107 (2) | 0.64867 (18) | 0.06903 (8) | 0.0460 (5) | |
H36 | 0.0626 | 0.7039 | 0.0516 | 0.055* | |
C37 | 0.2401 (2) | 0.63630 (17) | 0.05979 (7) | 0.0425 (5) | |
H37 | 0.2821 | 0.6835 | 0.0366 | 0.051* | |
C38 | 0.30705 (19) | 0.55453 (17) | 0.08469 (7) | 0.0394 (4) | |
H38 | 0.3960 | 0.5446 | 0.0785 | 0.047* | |
C39 | 0.24534 (18) | 0.48612 (16) | 0.11897 (7) | 0.0334 (4) | |
H39 | 0.2937 | 0.4294 | 0.1352 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.03074 (12) | 0.03593 (14) | 0.02021 (11) | −0.00552 (9) | 0.00718 (8) | −0.00348 (8) |
Cl1 | 0.0353 (2) | 0.0452 (3) | 0.0245 (2) | −0.00992 (19) | 0.00390 (16) | −0.00040 (17) |
N1 | 0.0281 (7) | 0.0408 (9) | 0.0249 (7) | −0.0026 (6) | 0.0038 (5) | −0.0060 (6) |
N2 | 0.0321 (7) | 0.0373 (9) | 0.0207 (6) | 0.0006 (6) | 0.0049 (5) | −0.0027 (6) |
N3 | 0.0290 (7) | 0.0365 (9) | 0.0251 (7) | −0.0038 (6) | 0.0034 (5) | −0.0035 (6) |
C1 | 0.0338 (9) | 0.0502 (12) | 0.0277 (8) | −0.0009 (8) | 0.0068 (7) | −0.0072 (8) |
C2 | 0.0393 (10) | 0.0574 (14) | 0.0359 (10) | 0.0034 (10) | 0.0083 (8) | −0.0122 (9) |
C3 | 0.0426 (11) | 0.0461 (12) | 0.0487 (12) | 0.0066 (9) | 0.0023 (9) | −0.0132 (10) |
C4 | 0.0421 (10) | 0.0402 (11) | 0.0420 (10) | 0.0008 (9) | 0.0026 (8) | −0.0031 (9) |
C5 | 0.0309 (9) | 0.0393 (11) | 0.0299 (9) | −0.0020 (8) | 0.0020 (7) | −0.0054 (8) |
C6 | 0.0423 (10) | 0.0375 (11) | 0.0318 (9) | −0.0024 (8) | 0.0106 (8) | 0.0012 (8) |
C7 | 0.0342 (9) | 0.0431 (11) | 0.0224 (8) | 0.0011 (8) | 0.0099 (7) | −0.0001 (7) |
C8 | 0.0291 (8) | 0.0414 (10) | 0.0209 (7) | 0.0012 (7) | −0.0003 (6) | −0.0017 (7) |
C9 | 0.0349 (9) | 0.0478 (12) | 0.0251 (8) | 0.0086 (8) | 0.0022 (7) | −0.0027 (8) |
C10 | 0.0402 (10) | 0.0463 (12) | 0.0374 (10) | 0.0105 (9) | −0.0008 (8) | −0.0105 (9) |
C11 | 0.0460 (11) | 0.0346 (11) | 0.0492 (11) | −0.0002 (9) | 0.0012 (9) | −0.0047 (9) |
C12 | 0.0368 (9) | 0.0404 (11) | 0.0346 (9) | −0.0060 (8) | 0.0054 (7) | −0.0021 (8) |
C13 | 0.0401 (10) | 0.0563 (13) | 0.0289 (9) | 0.0066 (9) | −0.0048 (8) | −0.0070 (9) |
C14 | 0.0368 (19) | 0.043 (2) | 0.0360 (14) | −0.0077 (14) | −0.0060 (11) | 0.0073 (14) |
C15 | 0.039 (2) | 0.063 (3) | 0.072 (2) | 0.002 (2) | −0.0006 (16) | −0.012 (2) |
C14A | 0.037 (5) | 0.044 (7) | 0.033 (4) | 0.005 (4) | −0.003 (3) | 0.001 (4) |
C15A | 0.043 (7) | 0.072 (10) | 0.085 (8) | 0.005 (7) | 0.002 (5) | 0.007 (8) |
B1 | 0.0282 (9) | 0.0284 (10) | 0.0222 (8) | −0.0008 (8) | 0.0023 (7) | 0.0014 (7) |
C16 | 0.0285 (8) | 0.0280 (9) | 0.0221 (7) | 0.0032 (7) | 0.0048 (6) | −0.0009 (6) |
C17 | 0.0504 (11) | 0.0290 (10) | 0.0260 (8) | 0.0003 (8) | 0.0073 (7) | −0.0001 (7) |
C18 | 0.0760 (15) | 0.0366 (11) | 0.0270 (9) | 0.0242 (11) | 0.0126 (9) | 0.0059 (8) |
C19 | 0.0504 (12) | 0.0747 (17) | 0.0267 (9) | 0.0310 (12) | −0.0003 (8) | 0.0015 (10) |
C20 | 0.0305 (9) | 0.0762 (16) | 0.0282 (9) | 0.0044 (10) | 0.0000 (7) | −0.0080 (10) |
C21 | 0.0322 (9) | 0.0410 (10) | 0.0247 (8) | −0.0013 (8) | 0.0042 (7) | −0.0015 (7) |
C22 | 0.0271 (8) | 0.0341 (10) | 0.0223 (7) | −0.0049 (7) | 0.0056 (6) | −0.0001 (7) |
C23 | 0.0344 (9) | 0.0364 (10) | 0.0279 (8) | −0.0013 (8) | 0.0034 (7) | −0.0033 (7) |
C24 | 0.0497 (11) | 0.0360 (11) | 0.0375 (10) | −0.0006 (9) | 0.0111 (8) | −0.0062 (8) |
C25 | 0.0528 (12) | 0.0467 (12) | 0.0304 (9) | −0.0147 (10) | 0.0105 (8) | −0.0116 (8) |
C26 | 0.0381 (10) | 0.0567 (13) | 0.0236 (8) | −0.0133 (9) | 0.0018 (7) | −0.0037 (8) |
C27 | 0.0320 (9) | 0.0420 (11) | 0.0262 (8) | −0.0024 (8) | 0.0038 (7) | −0.0001 (8) |
C28 | 0.0316 (8) | 0.0311 (9) | 0.0208 (7) | 0.0036 (7) | 0.0013 (6) | 0.0033 (7) |
C29 | 0.0335 (9) | 0.0404 (11) | 0.0319 (9) | −0.0011 (8) | 0.0046 (7) | −0.0025 (8) |
C30 | 0.0311 (10) | 0.0620 (14) | 0.0404 (11) | 0.0027 (9) | 0.0042 (8) | −0.0041 (10) |
C31 | 0.0430 (11) | 0.0592 (14) | 0.0398 (11) | 0.0219 (10) | 0.0061 (9) | −0.0003 (10) |
C32 | 0.0596 (13) | 0.0363 (11) | 0.0349 (10) | 0.0142 (10) | 0.0048 (9) | −0.0003 (8) |
C33 | 0.0420 (10) | 0.0328 (10) | 0.0298 (9) | 0.0015 (8) | 0.0029 (7) | 0.0010 (7) |
C34 | 0.0329 (9) | 0.0300 (9) | 0.0209 (7) | −0.0029 (7) | −0.0003 (6) | 0.0002 (7) |
C35 | 0.0388 (10) | 0.0434 (11) | 0.0299 (9) | 0.0016 (9) | 0.0030 (7) | 0.0079 (8) |
C36 | 0.0589 (13) | 0.0457 (12) | 0.0336 (10) | 0.0047 (10) | 0.0030 (9) | 0.0161 (9) |
C37 | 0.0534 (12) | 0.0430 (12) | 0.0312 (9) | −0.0118 (9) | 0.0047 (8) | 0.0100 (8) |
C38 | 0.0358 (10) | 0.0511 (12) | 0.0315 (9) | −0.0092 (9) | 0.0053 (7) | 0.0041 (8) |
C39 | 0.0352 (9) | 0.0361 (10) | 0.0289 (8) | −0.0008 (8) | 0.0039 (7) | 0.0053 (7) |
Cu1—N1 | 1.9984 (16) | B1—C34 | 1.648 (2) |
Cu1—N3 | 2.0024 (15) | B1—C16 | 1.649 (2) |
Cu1—N2 | 2.0431 (14) | B1—C28 | 1.650 (2) |
Cu1—Cl1i | 2.2754 (5) | B1—C22 | 1.650 (3) |
Cu1—Cl1 | 2.6861 (5) | C16—C17 | 1.400 (2) |
Cl1—Cu1i | 2.2754 (5) | C16—C21 | 1.402 (2) |
N1—C1 | 1.346 (2) | C17—C18 | 1.391 (3) |
N1—C5 | 1.346 (2) | C17—H17 | 0.9500 |
N2—C6 | 1.481 (2) | C18—C19 | 1.384 (3) |
N2—C7 | 1.483 (2) | C18—H18 | 0.9500 |
N2—C13 | 1.508 (2) | C19—C20 | 1.377 (3) |
N3—C12 | 1.341 (2) | C19—H19 | 0.9500 |
N3—C8 | 1.347 (2) | C20—C21 | 1.398 (3) |
C1—C2 | 1.375 (3) | C20—H20 | 0.9500 |
C1—H1 | 0.9500 | C21—H21 | 0.9500 |
C2—C3 | 1.383 (3) | C22—C23 | 1.401 (3) |
C2—H2 | 0.9500 | C22—C27 | 1.406 (2) |
C3—C4 | 1.387 (3) | C23—C24 | 1.395 (3) |
C3—H3 | 0.9500 | C23—H23 | 0.9500 |
C4—C5 | 1.384 (3) | C24—C25 | 1.383 (3) |
C4—H4 | 0.9500 | C24—H24 | 0.9500 |
C5—C6 | 1.506 (2) | C25—C26 | 1.380 (3) |
C6—H6A | 0.9900 | C25—H25 | 0.9500 |
C6—H6B | 0.9900 | C26—C27 | 1.393 (3) |
C7—C8 | 1.500 (3) | C26—H26 | 0.9500 |
C7—H7A | 0.9900 | C27—H27 | 0.9500 |
C7—H7B | 0.9900 | C28—C33 | 1.401 (3) |
C8—C9 | 1.386 (3) | C28—C29 | 1.401 (2) |
C9—C10 | 1.373 (3) | C29—C30 | 1.395 (3) |
C9—H9 | 0.9500 | C29—H29 | 0.9500 |
C10—C11 | 1.383 (3) | C30—C31 | 1.377 (3) |
C10—H10 | 0.9500 | C30—H30 | 0.9500 |
C11—C12 | 1.378 (3) | C31—C32 | 1.385 (3) |
C11—H11 | 0.9500 | C31—H31 | 0.9500 |
C12—H12 | 0.9500 | C32—C33 | 1.394 (3) |
C13—C14A | 1.501 (9) | C32—H32 | 0.9500 |
C13—C14 | 1.512 (4) | C33—H33 | 0.9500 |
C13—H13A | 0.9900 | C34—C35 | 1.398 (3) |
C13—H13B | 0.9900 | C34—C39 | 1.401 (2) |
C13—H13C | 0.9900 | C35—C36 | 1.396 (3) |
C13—H13D | 0.9900 | C35—H35 | 0.9500 |
C14—C15 | 1.298 (8) | C36—C37 | 1.380 (3) |
C14—H14 | 0.9500 | C36—H36 | 0.9500 |
C15—H15A | 0.9500 | C37—C38 | 1.373 (3) |
C15—H15B | 0.9500 | C37—H37 | 0.9500 |
C14A—C15A | 1.26 (2) | C38—C39 | 1.393 (3) |
C14A—H14A | 0.9500 | C38—H38 | 0.9500 |
C15A—H15C | 0.9500 | C39—H39 | 0.9500 |
C15A—H15D | 0.9500 | ||
N1—Cu1—N3 | 163.03 (6) | C15A—C14A—H14A | 122.3 |
N1—Cu1—N2 | 82.34 (6) | C13—C14A—H14A | 122.3 |
N3—Cu1—N2 | 81.17 (6) | C14A—C15A—H15C | 120.0 |
N1—Cu1—Cl1i | 98.38 (4) | C14A—C15A—H15D | 120.0 |
N3—Cu1—Cl1i | 97.16 (4) | H15C—C15A—H15D | 120.0 |
N2—Cu1—Cl1i | 170.01 (4) | C34—B1—C16 | 112.33 (14) |
N1—Cu1—Cl1 | 94.86 (4) | C34—B1—C28 | 110.84 (14) |
N3—Cu1—Cl1 | 91.36 (4) | C16—B1—C28 | 106.17 (13) |
N2—Cu1—Cl1 | 97.92 (4) | C34—B1—C22 | 104.35 (13) |
Cl1i—Cu1—Cl1 | 91.960 (15) | C16—B1—C22 | 110.60 (14) |
Cu1i—Cl1—Cu1 | 88.041 (15) | C28—B1—C22 | 112.70 (14) |
C1—N1—C5 | 118.75 (17) | C17—C16—C21 | 114.94 (16) |
C1—N1—Cu1 | 126.67 (14) | C17—C16—B1 | 120.84 (15) |
C5—N1—Cu1 | 114.00 (11) | C21—C16—B1 | 124.20 (15) |
C6—N2—C7 | 113.21 (14) | C18—C17—C16 | 123.01 (19) |
C6—N2—C13 | 111.24 (15) | C18—C17—H17 | 118.5 |
C7—N2—C13 | 109.16 (13) | C16—C17—H17 | 118.5 |
C6—N2—Cu1 | 106.20 (10) | C19—C18—C17 | 120.0 (2) |
C7—N2—Cu1 | 104.50 (11) | C19—C18—H18 | 120.0 |
C13—N2—Cu1 | 112.37 (11) | C17—C18—H18 | 120.0 |
C12—N3—C8 | 119.01 (16) | C20—C19—C18 | 119.11 (18) |
C12—N3—Cu1 | 128.37 (12) | C20—C19—H19 | 120.4 |
C8—N3—Cu1 | 112.59 (12) | C18—C19—H19 | 120.4 |
N1—C1—C2 | 122.28 (19) | C19—C20—C21 | 120.1 (2) |
N1—C1—H1 | 118.9 | C19—C20—H20 | 120.0 |
C2—C1—H1 | 118.9 | C21—C20—H20 | 120.0 |
C1—C2—C3 | 119.07 (18) | C20—C21—C16 | 122.72 (19) |
C1—C2—H2 | 120.5 | C20—C21—H21 | 118.6 |
C3—C2—H2 | 120.5 | C16—C21—H21 | 118.6 |
C2—C3—C4 | 119.1 (2) | C23—C22—C27 | 114.71 (16) |
C2—C3—H3 | 120.5 | C23—C22—B1 | 124.03 (15) |
C4—C3—H3 | 120.5 | C27—C22—B1 | 120.98 (16) |
C5—C4—C3 | 118.9 (2) | C24—C23—C22 | 123.39 (17) |
C5—C4—H4 | 120.6 | C24—C23—H23 | 118.3 |
C3—C4—H4 | 120.6 | C22—C23—H23 | 118.3 |
N1—C5—C4 | 121.93 (17) | C25—C24—C23 | 119.76 (19) |
N1—C5—C6 | 114.73 (16) | C25—C24—H24 | 120.1 |
C4—C5—C6 | 123.34 (18) | C23—C24—H24 | 120.1 |
N2—C6—C5 | 108.74 (15) | C26—C25—C24 | 118.94 (18) |
N2—C6—H6A | 109.9 | C26—C25—H25 | 120.5 |
C5—C6—H6A | 109.9 | C24—C25—H25 | 120.5 |
N2—C6—H6B | 109.9 | C25—C26—C27 | 120.60 (18) |
C5—C6—H6B | 109.9 | C25—C26—H26 | 119.7 |
H6A—C6—H6B | 108.3 | C27—C26—H26 | 119.7 |
N2—C7—C8 | 107.27 (14) | C26—C27—C22 | 122.59 (18) |
N2—C7—H7A | 110.3 | C26—C27—H27 | 118.7 |
C8—C7—H7A | 110.3 | C22—C27—H27 | 118.7 |
N2—C7—H7B | 110.3 | C33—C28—C29 | 115.56 (16) |
C8—C7—H7B | 110.3 | C33—C28—B1 | 120.13 (15) |
H7A—C7—H7B | 108.5 | C29—C28—B1 | 124.20 (16) |
N3—C8—C9 | 121.64 (18) | C30—C29—C28 | 122.22 (19) |
N3—C8—C7 | 115.62 (15) | C30—C29—H29 | 118.9 |
C9—C8—C7 | 122.74 (16) | C28—C29—H29 | 118.9 |
C10—C9—C8 | 118.95 (18) | C31—C30—C29 | 120.5 (2) |
C10—C9—H9 | 120.5 | C31—C30—H30 | 119.8 |
C8—C9—H9 | 120.5 | C29—C30—H30 | 119.8 |
C9—C10—C11 | 119.47 (18) | C30—C31—C32 | 119.13 (19) |
C9—C10—H10 | 120.3 | C30—C31—H31 | 120.4 |
C11—C10—H10 | 120.3 | C32—C31—H31 | 120.4 |
C12—C11—C10 | 118.9 (2) | C31—C32—C33 | 119.9 (2) |
C12—C11—H11 | 120.5 | C31—C32—H32 | 120.0 |
C10—C11—H11 | 120.5 | C33—C32—H32 | 120.0 |
N3—C12—C11 | 121.99 (18) | C32—C33—C28 | 122.66 (19) |
N3—C12—H12 | 119.0 | C32—C33—H33 | 118.7 |
C11—C12—H12 | 119.0 | C28—C33—H33 | 118.7 |
C14A—C13—N2 | 116.2 (3) | C35—C34—C39 | 114.66 (16) |
N2—C13—C14 | 112.03 (17) | C35—C34—B1 | 123.55 (15) |
N2—C13—H13A | 109.2 | C39—C34—B1 | 121.48 (16) |
C14—C13—H13A | 109.2 | C36—C35—C34 | 122.96 (18) |
N2—C13—H13B | 109.2 | C36—C35—H35 | 118.5 |
C14—C13—H13B | 109.2 | C34—C35—H35 | 118.5 |
H13A—C13—H13B | 107.9 | C37—C36—C35 | 120.17 (19) |
C14A—C13—H13C | 108.2 | C37—C36—H36 | 119.9 |
N2—C13—H13C | 108.2 | C35—C36—H36 | 119.9 |
C14A—C13—H13D | 108.2 | C38—C37—C36 | 118.82 (18) |
N2—C13—H13D | 108.2 | C38—C37—H37 | 120.6 |
H13C—C13—H13D | 107.4 | C36—C37—H37 | 120.6 |
C15—C14—C13 | 123.5 (5) | C37—C38—C39 | 120.39 (18) |
C15—C14—H14 | 118.3 | C37—C38—H38 | 119.8 |
C13—C14—H14 | 118.3 | C39—C38—H38 | 119.8 |
C14—C15—H15A | 120.0 | C38—C39—C34 | 122.96 (18) |
C14—C15—H15B | 120.0 | C38—C39—H39 | 118.5 |
H15A—C15—H15B | 120.0 | C34—C39—H39 | 118.5 |
C15A—C14A—C13 | 115.5 (15) | ||
C5—N1—C1—C2 | 0.1 (3) | C16—C17—C18—C19 | 1.1 (3) |
Cu1—N1—C1—C2 | 170.78 (14) | C17—C18—C19—C20 | 2.2 (3) |
N1—C1—C2—C3 | −0.6 (3) | C18—C19—C20—C21 | −2.6 (3) |
C1—C2—C3—C4 | 0.7 (3) | C19—C20—C21—C16 | −0.3 (3) |
C2—C3—C4—C5 | −0.3 (3) | C17—C16—C21—C20 | 3.4 (3) |
C1—N1—C5—C4 | 0.4 (3) | B1—C16—C21—C20 | −178.08 (16) |
Cu1—N1—C5—C4 | −171.48 (14) | C34—B1—C22—C23 | 100.91 (18) |
C1—N1—C5—C6 | −178.74 (16) | C16—B1—C22—C23 | −20.1 (2) |
Cu1—N1—C5—C6 | 9.42 (19) | C28—B1—C22—C23 | −138.76 (16) |
C3—C4—C5—N1 | −0.3 (3) | C34—B1—C22—C27 | −72.70 (18) |
C3—C4—C5—C6 | 178.75 (18) | C16—B1—C22—C27 | 166.29 (14) |
C7—N2—C6—C5 | 153.66 (15) | C28—B1—C22—C27 | 47.6 (2) |
C13—N2—C6—C5 | −82.99 (17) | C27—C22—C23—C24 | −0.8 (3) |
Cu1—N2—C6—C5 | 39.56 (17) | B1—C22—C23—C24 | −174.80 (16) |
N1—C5—C6—N2 | −33.5 (2) | C22—C23—C24—C25 | 0.5 (3) |
C4—C5—C6—N2 | 147.40 (18) | C23—C24—C25—C26 | 0.0 (3) |
C6—N2—C7—C8 | −159.88 (14) | C24—C25—C26—C27 | −0.2 (3) |
C13—N2—C7—C8 | 75.62 (18) | C25—C26—C27—C22 | −0.2 (3) |
Cu1—N2—C7—C8 | −44.77 (15) | C23—C22—C27—C26 | 0.7 (2) |
C12—N3—C8—C9 | 1.0 (3) | B1—C22—C27—C26 | 174.85 (16) |
Cu1—N3—C8—C9 | 179.30 (13) | C34—B1—C28—C33 | −46.5 (2) |
C12—N3—C8—C7 | −179.71 (15) | C16—B1—C28—C33 | 75.74 (19) |
Cu1—N3—C8—C7 | −1.45 (19) | C22—B1—C28—C33 | −163.04 (15) |
N2—C7—C8—N3 | 31.9 (2) | C34—B1—C28—C29 | 137.32 (17) |
N2—C7—C8—C9 | −148.81 (16) | C16—B1—C28—C29 | −100.43 (18) |
N3—C8—C9—C10 | −1.3 (3) | C22—B1—C28—C29 | 20.8 (2) |
C7—C8—C9—C10 | 179.47 (17) | C33—C28—C29—C30 | 0.9 (3) |
C8—C9—C10—C11 | 0.5 (3) | B1—C28—C29—C30 | 177.23 (17) |
C9—C10—C11—C12 | 0.7 (3) | C28—C29—C30—C31 | 0.2 (3) |
C8—N3—C12—C11 | 0.1 (3) | C29—C30—C31—C32 | −1.0 (3) |
Cu1—N3—C12—C11 | −177.82 (14) | C30—C31—C32—C33 | 0.6 (3) |
C10—C11—C12—N3 | −1.0 (3) | C31—C32—C33—C28 | 0.6 (3) |
C6—N2—C13—C14A | 51.9 (6) | C29—C28—C33—C32 | −1.3 (3) |
C7—N2—C13—C14A | 177.5 (6) | B1—C28—C33—C32 | −177.77 (16) |
Cu1—N2—C13—C14A | −67.0 (6) | C16—B1—C34—C35 | −144.98 (17) |
C6—N2—C13—C14 | 89.7 (3) | C28—B1—C34—C35 | −26.4 (2) |
C7—N2—C13—C14 | −144.7 (2) | C22—B1—C34—C35 | 95.18 (19) |
Cu1—N2—C13—C14 | −29.2 (3) | C16—B1—C34—C39 | 41.8 (2) |
N2—C13—C14—C15 | −115.0 (3) | C28—B1—C34—C39 | 160.34 (16) |
N2—C13—C14A—C15A | 112.0 (9) | C22—B1—C34—C39 | −78.09 (19) |
C34—B1—C16—C17 | −159.66 (15) | C39—C34—C35—C36 | −1.2 (3) |
C28—B1—C16—C17 | 79.05 (19) | B1—C34—C35—C36 | −174.91 (18) |
C22—B1—C16—C17 | −43.5 (2) | C34—C35—C36—C37 | −0.3 (3) |
C34—B1—C16—C21 | 21.9 (2) | C35—C36—C37—C38 | 1.3 (3) |
C28—B1—C16—C21 | −99.42 (18) | C36—C37—C38—C39 | −0.6 (3) |
C22—B1—C16—C21 | 138.02 (16) | C37—C38—C39—C34 | −1.1 (3) |
C21—C16—C17—C18 | −3.7 (3) | C35—C34—C39—C38 | 2.0 (3) |
B1—C16—C17—C18 | 177.65 (16) | B1—C34—C39—C38 | 175.79 (17) |
Symmetry code: (i) −x+1, −y+2, −z. |