Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810101850X/na0129sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129Vsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129VIsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129VIIsup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129VIIIsup9.hkl |
CCDC references: 180182; 180183; 180184; 180185; 180186; 180187; 180188; 180189
Data collection: Kappa-CCD server software (Nonius, 1997) for (I), (II), (IV), (V), (VI), (VII), (VIII); Kappa-CCD server softare (Nonius, 1997) for (III). For all compounds, cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b). Molecular graphics: PLATON (Spek, 20001) for (I); PLATON (Spek, 2001) for (II), (III), (IV), (V), (VI), (VII), (VIII). For all compounds, software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999).
C32H38N4NiO4 | F(000) = 636 |
Mr = 601.37 | Dx = 1.366 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.4970 (4) Å | Cell parameters from 3144 reflections |
b = 10.6563 (4) Å | θ = 2.6–27.5° |
c = 11.9407 (4) Å | µ = 0.71 mm−1 |
β = 92.2080 (17)° | T = 150 K |
V = 1461.83 (9) Å3 | Block, purple |
Z = 2 | 0.36 × 0.26 × 0.18 mm |
Kappa-CCD diffractometer | 3328 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2895 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→14 |
Tmin = 0.785, Tmax = 0.883 | k = 0→13 |
9394 measured reflections | l = −15→15 |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0155P)2 + 0.7435P] where P = (Fo2 + 2Fc2)/3 |
3328 reflections | (Δ/σ)max = 0.001 |
187 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.01919 (9) | |
O1 | 0.39898 (9) | 0.34617 (10) | 0.54652 (8) | 0.0268 (2) | |
O2 | 0.39786 (11) | 0.22396 (11) | 0.39435 (10) | 0.0384 (3) | |
C11 | 0.24257 (12) | 0.19082 (13) | 0.64991 (12) | 0.0217 (3) | |
C12 | 0.27874 (12) | 0.16666 (13) | 0.54398 (12) | 0.0210 (3) | |
C13 | 0.23432 (13) | 0.06007 (14) | 0.48509 (13) | 0.0270 (3) | |
C14 | 0.15576 (14) | −0.01766 (15) | 0.53301 (14) | 0.0308 (3) | |
C15 | 0.11721 (13) | 0.00529 (14) | 0.64248 (14) | 0.0275 (3) | |
C16 | 0.03531 (15) | −0.07267 (17) | 0.69482 (16) | 0.0396 (4) | |
C17 | −0.00158 (16) | −0.0457 (2) | 0.79955 (17) | 0.0442 (5) | |
C18 | 0.04227 (15) | 0.05950 (18) | 0.85834 (15) | 0.0383 (4) | |
C19 | 0.12280 (13) | 0.13622 (15) | 0.81110 (13) | 0.0290 (3) | |
C110 | 0.16119 (12) | 0.11186 (14) | 0.70172 (12) | 0.0232 (3) | |
C111 | 0.36627 (12) | 0.25133 (13) | 0.48961 (12) | 0.0220 (3) | |
N1 | 0.60752 (11) | 0.39074 (12) | 0.40417 (10) | 0.0245 (3) | |
C2 | 0.71607 (14) | 0.37508 (17) | 0.47247 (14) | 0.0325 (4) | |
C3 | 0.68618 (14) | 0.35421 (17) | 0.59425 (14) | 0.0334 (4) | |
N4 | 0.61582 (11) | 0.46044 (13) | 0.63234 (10) | 0.0263 (3) | |
C5 | 0.56383 (14) | 0.43833 (16) | 0.74220 (12) | 0.0302 (3) | |
C6 | 0.48728 (14) | 0.54690 (16) | 0.77773 (12) | 0.0312 (3) | |
C7 | 0.37303 (14) | 0.56273 (15) | 0.71011 (12) | 0.0286 (3) | |
H11 | 0.2726 | 0.2619 | 0.6894 | 0.026* | |
H13 | 0.2594 | 0.0427 | 0.4118 | 0.032* | |
H14 | 0.1265 | −0.0882 | 0.4923 | 0.037* | |
H16 | 0.0057 | −0.1447 | 0.6565 | 0.048* | |
H17 | −0.0572 | −0.0984 | 0.8329 | 0.053* | |
H18 | 0.0161 | 0.0776 | 0.9311 | 0.046* | |
H19 | 0.1531 | 0.2062 | 0.8520 | 0.035* | |
H1 | 0.5731 | 0.3120 | 0.3970 | 0.029* | |
H2A | 0.7652 | 0.4509 | 0.4664 | 0.039* | |
H2B | 0.7603 | 0.3023 | 0.4450 | 0.039* | |
H3A | 0.6420 | 0.2750 | 0.6011 | 0.040* | |
H3B | 0.7586 | 0.3474 | 0.6415 | 0.040* | |
H4 | 0.6654 | 0.5290 | 0.6408 | 0.032* | |
H5A | 0.6270 | 0.4255 | 0.7998 | 0.036* | |
H5B | 0.5166 | 0.3607 | 0.7380 | 0.036* | |
H6A | 0.5324 | 0.6256 | 0.7724 | 0.037* | |
H6B | 0.4693 | 0.5350 | 0.8574 | 0.037* | |
H7A | 0.3322 | 0.4810 | 0.7053 | 0.034* | |
H7B | 0.3226 | 0.6226 | 0.7491 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.02131 (14) | 0.01902 (14) | 0.01737 (13) | −0.00436 (10) | 0.00246 (9) | 0.00057 (9) |
O1 | 0.0335 (6) | 0.0237 (5) | 0.0235 (5) | −0.0114 (4) | 0.0066 (4) | −0.0022 (4) |
O2 | 0.0501 (7) | 0.0347 (6) | 0.0319 (6) | −0.0172 (5) | 0.0192 (5) | −0.0103 (5) |
C11 | 0.0203 (7) | 0.0188 (7) | 0.0259 (7) | −0.0012 (5) | 0.0000 (5) | 0.0024 (5) |
C12 | 0.0201 (6) | 0.0180 (6) | 0.0249 (7) | −0.0012 (5) | −0.0001 (5) | 0.0024 (5) |
C13 | 0.0299 (8) | 0.0249 (8) | 0.0261 (7) | −0.0042 (6) | 0.0000 (6) | −0.0008 (6) |
C14 | 0.0322 (8) | 0.0249 (8) | 0.0350 (8) | −0.0093 (6) | −0.0039 (7) | −0.0004 (6) |
C15 | 0.0234 (7) | 0.0249 (8) | 0.0339 (8) | −0.0054 (6) | −0.0016 (6) | 0.0075 (6) |
C16 | 0.0348 (9) | 0.0353 (9) | 0.0485 (10) | −0.0150 (7) | −0.0018 (8) | 0.0108 (8) |
C17 | 0.0329 (9) | 0.0484 (11) | 0.0519 (11) | −0.0128 (8) | 0.0085 (8) | 0.0194 (9) |
C18 | 0.0339 (9) | 0.0443 (10) | 0.0375 (9) | 0.0009 (8) | 0.0124 (7) | 0.0153 (8) |
C19 | 0.0265 (7) | 0.0288 (8) | 0.0321 (8) | 0.0027 (6) | 0.0050 (6) | 0.0069 (6) |
C110 | 0.0186 (6) | 0.0225 (7) | 0.0284 (7) | 0.0008 (5) | 0.0011 (5) | 0.0067 (6) |
C111 | 0.0237 (7) | 0.0202 (7) | 0.0222 (7) | −0.0026 (6) | 0.0025 (5) | 0.0013 (5) |
N1 | 0.0266 (6) | 0.0222 (6) | 0.0250 (6) | −0.0048 (5) | 0.0046 (5) | 0.0000 (5) |
C2 | 0.0256 (8) | 0.0372 (9) | 0.0351 (8) | 0.0034 (7) | 0.0054 (6) | 0.0020 (7) |
C3 | 0.0293 (8) | 0.0364 (9) | 0.0343 (8) | 0.0038 (7) | −0.0007 (7) | 0.0082 (7) |
N4 | 0.0272 (6) | 0.0288 (7) | 0.0228 (6) | −0.0071 (5) | 0.0009 (5) | 0.0035 (5) |
C5 | 0.0344 (8) | 0.0354 (9) | 0.0206 (7) | −0.0081 (7) | −0.0009 (6) | 0.0059 (6) |
C6 | 0.0393 (9) | 0.0330 (8) | 0.0215 (7) | −0.0115 (7) | 0.0038 (6) | −0.0014 (6) |
C7 | 0.0342 (8) | 0.0283 (8) | 0.0239 (7) | −0.0081 (7) | 0.0099 (6) | −0.0039 (6) |
Ni1—N4i | 2.070 (2) | C18—H18 | 0.95 |
Ni1—N4 | 2.070 (2) | C19—C110 | 1.419 (2) |
Ni1—N1i | 2.074 (2) | C19—H19 | 0.95 |
Ni1—N1 | 2.074 (2) | N1—C2 | 1.474 (2) |
Ni1—O1i | 2.096 (2) | N1—C7i | 1.477 (2) |
Ni1—O1 | 2.096 (2) | N1—H1 | 0.93 |
O1—C111 | 1.267 (2) | C2—C3 | 1.523 (2) |
O2—C111 | 1.242 (2) | C2—H2A | 0.99 |
C11—C12 | 1.371 (2) | C2—H2B | 0.99 |
C11—C110 | 1.418 (2) | C3—N4 | 1.473 (2) |
C11—H11 | 0.95 | C3—H3A | 0.99 |
C12—C13 | 1.420 (2) | C3—H3B | 0.99 |
C12—C111 | 1.516 (2) | N4—C5 | 1.481 (2) |
C13—C14 | 1.367 (2) | N4—H4 | 0.93 |
C13—H13 | 0.95 | C5—C6 | 1.524 (2) |
C14—C15 | 1.418 (2) | C5—H5A | 0.99 |
C14—H14 | 0.95 | C5—H5B | 0.99 |
C15—C16 | 1.419 (2) | C6—C7 | 1.524 (2) |
C15—C110 | 1.421 (2) | C6—H6A | 0.99 |
C16—C17 | 1.367 (3) | C6—H6B | 0.99 |
C16—H16 | 0.95 | C7—N1i | 1.477 (2) |
C17—C18 | 1.406 (3) | C7—H7A | 0.99 |
C17—H17 | 0.95 | C7—H7B | 0.99 |
C18—C19 | 1.373 (2) | ||
N4i—Ni1—N4 | 180.0 | O2—C111—O1 | 126.0 (12) |
N4i—Ni1—N1i | 85.83 (5) | O2—C111—C12 | 118.3 (2) |
N4—Ni1—N1i | 94.17 (5) | O1—C111—C12 | 115.7 (2) |
N4i—Ni1—N1 | 94.17 (5) | C2—N1—C7i | 113.2 (2) |
N4—Ni1—N1 | 85.83 (5) | C2—N1—Ni1 | 105.56 (9) |
N1i—Ni1—N1 | 180.0 | C7i—N1—Ni1 | 115.8 (2) |
N4i—Ni1—O1i | 89.15 (5) | C2—N1—H1 | 107.3 |
N4—Ni1—O1i | 90.85 (5) | C7i—N1—H1 | 107.3 |
N1i—Ni1—O1i | 93.17 (4) | Ni1—N1—H1 | 107.3 |
N1—Ni1—O1i | 86.83 (4) | N1—C2—C3 | 109.1 (2) |
N4i—Ni1—O1 | 90.85 (5) | N1—C2—H2A | 109.9 |
N4—Ni1—O1 | 89.15 (5) | C3—C2—H2A | 109.9 |
N1i—Ni1—O1 | 86.83 (4) | N1—C2—H2B | 109.9 |
N1—Ni1—O1 | 93.17 (4) | C3—C2—H2B | 109.9 |
O1i—Ni1—O1 | 180.0 | H2A—C2—H2B | 108.3 |
C111—O1—Ni1 | 129.63 (9) | N4—C3—C2 | 109.2 (2) |
C12—C11—C110 | 121.3 (2) | N4—C3—H3A | 109.8 |
C12—C11—H11 | 119.3 | C2—C3—H3A | 109.8 |
C110—C11—H11 | 119.3 | N4—C3—H3B | 109.8 |
C11—C12—C13 | 119.4 (2) | C2—C3—H3B | 109.8 |
C11—C12—C111 | 120.9 (2) | H3A—C3—H3B | 108.3 |
C13—C12—C111 | 119.7 (2) | C3—N4—C5 | 113.4 (2) |
C14—C13—C12 | 120.5 (2) | C3—N4—Ni1 | 105.41 (9) |
C14—C13—H13 | 119.7 | C5—N4—Ni1 | 116.02 (9) |
C12—C13—H13 | 119.7 | C3—N4—H4 | 107.2 |
C13—C14—C15 | 121.1 (2) | C5—N4—H4 | 107.2 |
C13—C14—H14 | 119.5 | Ni1—N4—H4 | 107.2 |
C15—C14—H14 | 119.5 | N4—C5—C6 | 112.5 (2) |
C14—C15—C16 | 122.8 (2) | N4—C5—H5A | 109.1 |
C14—C15—C110 | 118.6 (2) | C6—C5—H5A | 109.1 |
C16—C15—C110 | 118.6 (2) | N4—C5—H5B | 109.1 |
C17—C16—C15 | 121.0 (2) | C6—C5—H5B | 109.1 |
C17—C16—H16 | 119.5 | H5A—C5—H5B | 107.8 |
C15—C16—H16 | 119.5 | C5—C6—C7 | 115.6 (2) |
C16—C17—C18 | 120.5 (2) | C5—C6—H6A | 108.4 |
C16—C17—H17 | 119.8 | C7—C6—H6A | 108.4 |
C18—C17—H17 | 119.8 | C5—C6—H6B | 108.4 |
C19—C18—C17 | 120.3 (2) | C7—C6—H6B | 108.4 |
C19—C18—H18 | 119.9 | H6A—C6—H6B | 107.4 |
C17—C18—H18 | 119.9 | N1i—C7—C6 | 111.6 (2) |
C18—C19—C110 | 120.5 (2) | N1i—C7—H7A | 109.3 |
C18—C19—H19 | 119.7 | C6—C7—H7A | 109.3 |
C110—C19—H19 | 119.7 | N1i—C7—H7B | 109.3 |
C11—C110—C19 | 121.8 (2) | C6—C7—H7B | 109.3 |
C11—C110—C15 | 119.0 (2) | H7A—C7—H7B | 108.0 |
C19—C110—C15 | 119.2 (2) | ||
N4i—Ni1—O1—C111 | 56.5 (2) | C11—C12—C111—O1 | −2.5 (2) |
N4—Ni1—O1—C111 | −123.5 (2) | C13—C12—C111—O1 | 178.1 (2) |
N1i—Ni1—O1—C111 | 142.3 (3) | N4i—Ni1—N1—C2 | 165.9 (2) |
N1—Ni1—O1—C111 | −37.7 (2) | N4—Ni1—N1—C2 | −14.1 (2) |
C110—C11—C12—C13 | −0.3 (2) | O1i—Ni1—N1—C2 | 77.03 (9) |
C110—C11—C12—C111 | −179.7 (2) | O1—Ni1—N1—C2 | −103.0 (2) |
C11—C12—C13—C14 | 0.3 (2) | N4i—Ni1—N1—C7i | 39.8 (2) |
C111—C12—C13—C14 | 179.7 (2) | N4—Ni1—N1—C7i | −140.2 (2) |
C12—C13—C14—C15 | −0.4 (2) | O1i—Ni1—N1—C7i | −49.1 (2) |
C13—C14—C15—C16 | 179.6 (2) | O1—Ni1—N1—C7i | 130.9 (2) |
C13—C14—C15—C110 | 0.5 (2) | C7i—N1—C2—C3 | 168.1 (2) |
C14—C15—C16—C17 | −178.5 (2) | Ni1—N1—C2—C3 | 40.4 (2) |
C110—C15—C16—C17 | 0.6 (3) | N1—C2—C3—N4 | −56.9 (2) |
C15—C16—C17—C18 | −0.8 (3) | C2—C3—N4—C5 | 169.2 (2) |
C16—C17—C18—C19 | −0.1 (3) | C2—C3—N4—Ni1 | 41.3 (2) |
C17—C18—C19—C110 | 1.2 (2) | N1i—Ni1—N4—C3 | 164.86 (9) |
C12—C11—C110—C19 | −179.7 (2) | N1—Ni1—N4—C3 | −15.14 (9) |
C12—C11—C110—C15 | 0.4 (2) | O1i—Ni1—N4—C3 | −101.90 (9) |
C18—C19—C110—C11 | 178.8 (2) | O1—Ni1—N4—C3 | 78.10 (9) |
C18—C19—C110—C15 | −1.4 (2) | N1i—Ni1—N4—C5 | 38.9 (2) |
C14—C15—C110—C11 | −0.5 (2) | N1—Ni1—N4—C5 | −141.4 (2) |
C16—C15—C110—C11 | −179.6 (2) | O1i—Ni1—N4—C5 | 131.8 (2) |
C14—C15—C110—C19 | 179.7 (2) | O1—Ni1—N4—C5 | −48.2 (2) |
C16—C15—C110—C19 | 0.5 (2) | C3—N4—C5—C6 | −177.6 (2) |
Ni1—O1—C111—O2 | 7.4 (2) | Ni1—N4—C5—C6 | −55.4 (2) |
Ni1—O1—C111—C12 | −171.29 (9) | N4—C5—C6—C7 | 70.1 (2) |
C11—C12—C111—O2 | 178.6 (2) | C5—C6—C7—N1i | −71.1 (2) |
C13—C12—C111—O2 | −0.7 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
C24H30N8NiO12 | Z = 1 |
Mr = 681.27 | F(000) = 354 |
Triclinic, P1 | Dx = 1.564 Mg m−3 |
a = 7.7663 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.7845 (6) Å | Cell parameters from 5718 reflections |
c = 10.4026 (7) Å | θ = 2.8–27.2° |
α = 99.826 (2)° | µ = 0.75 mm−1 |
β = 97.966 (2)° | T = 293 K |
γ = 108.388 (2)° | Plate, colourless |
V = 723.30 (7) Å3 | 0.30 × 0.24 × 0.02 mm |
Kappa-CCD diffractometer | 3135 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2560 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
φ scans, and ω scans with κ offsets | θmax = 27.2°, θmin = 2.8° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→9 |
Tmin = 0.807, Tmax = 0.985 | k = −12→11 |
17662 measured reflections | l = −13→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.097 | w = 1/[σ2(Fo2)P)2 + 0.3293P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3135 reflections | Δρmax = 0.29 e Å−3 |
206 parameters | Δρmin = −0.43 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.013 (3) |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891]which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.03420 (15) | |
N1 | 0.2732 (3) | 0.5215 (2) | 0.57420 (19) | 0.0407 (5) | |
C2 | 0.2156 (4) | 0.4009 (3) | 0.6446 (3) | 0.0529 (7) | |
C3 | 0.2281 (4) | 0.2618 (3) | 0.5626 (3) | 0.0538 (7) | |
N4 | 0.4181 (3) | 0.2920 (2) | 0.5391 (2) | 0.0415 (5) | |
C5 | 0.4378 (4) | 0.1739 (3) | 0.4400 (3) | 0.0469 (6) | |
C6 | 0.6350 (4) | 0.2085 (3) | 0.4189 (3) | 0.0494 (6) | |
C7 | 0.7033 (4) | 0.3306 (3) | 0.3461 (3) | 0.0484 (6) | |
O11 | 0.3435 (2) | 0.40263 (19) | 0.30221 (16) | 0.0456 (4) | |
O12 | 0.1530 (2) | 0.5311 (2) | 0.28440 (18) | 0.0547 (5) | |
O32 | 0.0894 (3) | −0.0360 (3) | −0.2587 (2) | 0.0800 (7) | |
O31 | 0.2989 (3) | 0.0153 (2) | −0.0804 (2) | 0.0681 (6) | |
O51 | −0.3909 (3) | 0.3286 (3) | −0.0794 (2) | 0.0696 (6) | |
O52 | −0.4066 (3) | 0.1585 (2) | −0.2464 (2) | 0.0704 (6) | |
N3 | 0.1675 (4) | 0.0330 (2) | −0.1442 (2) | 0.0537 (6) | |
N5 | −0.3274 (3) | 0.2430 (3) | −0.1391 (2) | 0.0520 (6) | |
C11 | 0.1133 (3) | 0.3314 (2) | 0.1059 (2) | 0.0362 (5) | |
C12 | 0.1873 (3) | 0.2326 (3) | 0.0429 (2) | 0.0402 (5) | |
C13 | 0.0918 (3) | 0.1419 (3) | −0.0800 (2) | 0.0422 (6) | |
C14 | −0.0744 (4) | 0.1447 (3) | −0.1438 (2) | 0.0454 (6) | |
C15 | −0.1450 (3) | 0.2432 (3) | −0.0773 (2) | 0.0406 (5) | |
C16 | −0.0543 (3) | 0.3368 (3) | 0.0452 (2) | 0.0387 (5) | |
C17 | 0.2114 (3) | 0.4321 (3) | 0.2431 (2) | 0.0373 (5) | |
H1 | 0.1802 | 0.5011 | 0.5024 | 0.049* | |
H2A | 0.0894 | 0.3839 | 0.6563 | 0.063* | |
H2B | 0.2958 | 0.4277 | 0.7319 | 0.063* | |
H3A | 0.1973 | 0.1828 | 0.6097 | 0.065* | |
H3B | 0.1406 | 0.2307 | 0.4781 | 0.065* | |
H4 | 0.4912 | 0.2983 | 0.6178 | 0.050* | |
H5A | 0.3560 | 0.1601 | 0.3558 | 0.056* | |
H5B | 0.3999 | 0.0820 | 0.4694 | 0.056* | |
H6A | 0.6451 | 0.1189 | 0.3693 | 0.059* | |
H6B | 0.7172 | 0.2355 | 0.5054 | 0.059* | |
H7A | 0.8211 | 0.3316 | 0.3244 | 0.058* | |
H7B | 0.6156 | 0.3098 | 0.2631 | 0.058* | |
H12 | 0.2993 | 0.2276 | 0.0829 | 0.048* | |
H14 | −0.1359 | 0.0836 | −0.2272 | 0.055* | |
H16 | −0.1049 | 0.4026 | 0.0865 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0336 (2) | 0.0363 (2) | 0.0305 (2) | 0.01418 (18) | 0.00215 (16) | 0.00157 (16) |
N1 | 0.0408 (11) | 0.0437 (11) | 0.0369 (11) | 0.0181 (9) | 0.0050 (8) | 0.0031 (9) |
C2 | 0.0536 (15) | 0.0572 (16) | 0.0560 (16) | 0.0230 (13) | 0.0247 (13) | 0.0161 (13) |
C3 | 0.0516 (15) | 0.0466 (15) | 0.0645 (18) | 0.0142 (12) | 0.0205 (13) | 0.0148 (13) |
N4 | 0.0432 (11) | 0.0433 (11) | 0.0371 (11) | 0.0181 (9) | 0.0043 (9) | 0.0045 (9) |
C5 | 0.0559 (15) | 0.0361 (13) | 0.0458 (14) | 0.0180 (11) | 0.0060 (12) | 0.0017 (11) |
C6 | 0.0545 (15) | 0.0464 (14) | 0.0495 (15) | 0.0274 (12) | 0.0077 (12) | 0.0009 (12) |
C7 | 0.0502 (14) | 0.0512 (15) | 0.0445 (14) | 0.0244 (12) | 0.0112 (11) | −0.0014 (11) |
O11 | 0.0459 (10) | 0.0510 (10) | 0.0361 (9) | 0.0235 (8) | −0.0060 (7) | −0.0013 (8) |
O12 | 0.0540 (11) | 0.0602 (12) | 0.0452 (10) | 0.0309 (9) | −0.0064 (8) | −0.0082 (9) |
O32 | 0.0983 (17) | 0.0786 (15) | 0.0522 (13) | 0.0348 (13) | 0.0104 (12) | −0.0174 (11) |
O31 | 0.0765 (15) | 0.0683 (14) | 0.0687 (14) | 0.0402 (12) | 0.0159 (12) | 0.0097 (11) |
O51 | 0.0534 (12) | 0.0792 (15) | 0.0716 (14) | 0.0291 (11) | −0.0048 (10) | 0.0081 (12) |
O52 | 0.0660 (13) | 0.0622 (13) | 0.0571 (13) | 0.0111 (10) | −0.0284 (10) | 0.0001 (10) |
N3 | 0.0663 (15) | 0.0442 (13) | 0.0481 (14) | 0.0169 (11) | 0.0188 (12) | 0.0028 (10) |
N5 | 0.0462 (12) | 0.0511 (13) | 0.0490 (13) | 0.0116 (11) | −0.0077 (10) | 0.0104 (11) |
C11 | 0.0376 (12) | 0.0355 (12) | 0.0307 (11) | 0.0090 (9) | 0.0014 (9) | 0.0064 (9) |
C12 | 0.0413 (13) | 0.0410 (13) | 0.0363 (12) | 0.0142 (10) | 0.0036 (10) | 0.0070 (10) |
C13 | 0.0503 (14) | 0.0383 (13) | 0.0363 (13) | 0.0149 (11) | 0.0091 (11) | 0.0043 (10) |
C14 | 0.0537 (15) | 0.0414 (14) | 0.0310 (12) | 0.0088 (11) | 0.0000 (11) | 0.0035 (10) |
C15 | 0.0385 (12) | 0.0406 (13) | 0.0352 (12) | 0.0074 (10) | −0.0032 (10) | 0.0100 (10) |
C16 | 0.0402 (12) | 0.0383 (12) | 0.0348 (12) | 0.0130 (10) | 0.0031 (10) | 0.0065 (10) |
C17 | 0.0338 (11) | 0.0399 (12) | 0.0332 (12) | 0.0119 (10) | 0.0005 (9) | 0.0019 (10) |
Ni1—N1 | 2.073 (2) | C6—H6B | 0.97 |
Ni1—N1i | 2.073 (2) | C7—N1i | 1.482 (3) |
Ni1—N4 | 2.062 (2) | C7—H7A | 0.97 |
Ni1—N4i | 2.062 (2) | C7—H7B | 0.97 |
Ni1—O11i | 2.127 (2) | O11—C17 | 1.259 (3) |
Ni1—O11 | 2.127 (2) | O12—C17 | 1.233 (3) |
N1—C2 | 1.477 (3) | O31—N3 | 1.214 (3) |
N1—C7i | 1.482 (3) | O32—N3 | 1.229 (3) |
N1—H1 | 0.91 | O51—N5 | 1.224 (3) |
C2—C3 | 1.516 (4) | O52—N5 | 1.218 (3) |
C2—H2A | 0.97 | N3—C13 | 1.479 (3) |
C2—H2B | 0.97 | N5—C15 | 1.472 (3) |
C3—N4 | 1.474 (3) | C11—C12 | 1.391 (3) |
C3—H3A | 0.97 | C11—C16 | 1.386 (3) |
C3—H3B | 0.97 | C11—C17 | 1.527 (3) |
N4—C5 | 1.473 (3) | C12—C13 | 1.381 (3) |
N4—H4 | 0.91 | C12—H12 | 0.93 |
C5—C6 | 1.516 (4) | C13—C14 | 1.377 (4) |
C5—H5A | 0.97 | C14—C15 | 1.386 (4) |
C5—H5B | 0.97 | C14—H14 | 0.93 |
C6—C7 | 1.517 (4) | C15—C16 | 1.380 (3) |
C6—H6A | 0.97 | C16—H16 | 0.93 |
N4—Ni1—N4i | 180.0 | C6—C5—H5B | 109.1 |
N4—Ni1—N1 | 85.46 (8) | H5A—C5—H5B | 107.9 |
N4i—Ni1—N1 | 94.54 (8) | C5—C6—C7 | 116.2 (2) |
N4—Ni1—N1i | 94.54 (8) | C5—C6—H6A | 108.2 |
N4i—Ni1—N1i | 85.46 (8) | C7—C6—H6A | 108.2 |
N1—Ni1—N1i | 180.0 | C5—C6—H6B | 108.2 |
N4—Ni1—O11i | 91.86 (7) | C7—C6—H6B | 108.2 |
N4i—Ni1—O11i | 88.14 (7) | H6A—C6—H6B | 107.4 |
N1—Ni1—O11i | 86.49 (7) | N1i—C7—C6 | 112.6 (2) |
N1i—Ni1—O11i | 93.51 (7) | N1i—C7—H7A | 109.1 |
N4—Ni1—O11 | 88.14 (7) | C6—C7—H7A | 109.1 |
N4i—Ni1—O11 | 91.86 (7) | N1i—C7—H7B | 109.1 |
N1—Ni1—O11 | 93.51 (7) | C6—C7—H7B | 109.1 |
N1i—Ni1—O11 | 86.49 (7) | H7A—C7—H7B | 107.8 |
O11i—Ni1—O11 | 180 | C17—O11—Ni1 | 127.9 (2) |
C2—N1—C7i | 114.0 (2) | O31—N3—O32 | 124.4 (3) |
C2—N1—Ni1 | 105.8 (2) | O31—N3—C13 | 118.5 (2) |
C7i—N1—Ni1 | 116.7 (2) | O32—N3—C13 | 117.0 (3) |
C2—N1—H1 | 106.6 | O52—N5—O51 | 123.7 (2) |
C7i—N1—H1 | 106.6 | O52—N5—C15 | 118.5 (2) |
Ni1—N1—H1 | 106.6 | O51—N5—C15 | 117.9 (2) |
N1—C2—C3 | 108.7 (2) | C16—C11—C12 | 119.8 (2) |
N1—C2—H2A | 109.9 | C16—C11—C17 | 119.2 (2) |
C3—C2—H2A | 109.9 | C12—C11—C17 | 121.0 (2) |
N1—C2—H2B | 109.9 | C13—C12—C11 | 118.9 (2) |
C3—C2—H2B | 109.9 | C13—C12—H12 | 120.6 |
H2A—C2—H2B | 108.3 | C11—C12—H12 | 120.6 |
N4—C3—C2 | 109.3 (2) | C14—C13—C12 | 123.0 (2) |
N4—C3—H3A | 109.8 | C14—C13—N3 | 118.3 (2) |
C2—C3—H3A | 109.8 | C12—C13—N3 | 118.6 (2) |
N4—C3—H3B | 109.8 | C13—C14—C15 | 116.5 (2) |
C2—C3—H3B | 109.8 | C13—C14—H14 | 121.8 |
H3A—C3—H3B | 108.3 | C15—C14—H14 | 121.8 |
C5—N4—C3 | 113.9 (2) | C16—C15—C14 | 122.8 (2) |
C5—N4—Ni1 | 115.8 (2) | C16—C15—N5 | 119.3 (2) |
C3—N4—Ni1 | 106.1 (2) | C14—C15—N5 | 117.9 (2) |
C5—N4—H4 | 106.8 | C15—C16—C11 | 119.1 (2) |
C3—N4—H4 | 106.8 | C15—C16—H16 | 120.5 |
Ni1—N4—H4 | 106.8 | C11—C16—H16 | 120.5 |
N4—C5—C6 | 112.4 (2) | O12—C17—O11 | 127.2 (2) |
N4—C5—H5A | 109.1 | O12—C17—C11 | 117.4 (2) |
C6—C5—H5A | 109.1 | O11—C17—C11 | 115.4 (2) |
N4—C5—H5B | 109.1 | ||
N4—Ni1—N1—C2 | 15.0 (2) | N1i—Ni1—O11—C17 | −144.0 (2) |
N4i—Ni1—N1—C2 | −165.0 (2) | C16—C11—C12—C13 | 0.4 (3) |
O11i—Ni1—N1—C2 | −77.1 (2) | C17—C11—C12—C13 | 178.8 (2) |
O11—Ni1—N1—C2 | 102.9 (2) | C11—C12—C13—C14 | 0.0 (4) |
N4—Ni1—N1—C7i | 143.0 (2) | C11—C12—C13—N3 | −177.7 (2) |
N4i—Ni1—N1—C7i | −37.0 (2) | O31—N3—C13—C14 | −169.6 (2) |
O11i—Ni1—N1—C7i | 50.9 (2) | O32—N3—C13—C14 | 9.0 (3) |
O11—Ni1—N1—C7i | −129.2 (2) | O31—N3—C13—C12 | 8.2 (3) |
C7i—N1—C2—C3 | −170.5 (2) | O32—N3—C13—C12 | −173.2 (2) |
Ni1—N1—C2—C3 | −41.0 (2) | C12—C13—C14—C15 | −0.9 (4) |
N1—C2—C3—N4 | 56.4 (3) | N3—C13—C14—C15 | 176.9 (2) |
C2—C3—N4—C5 | −169.1 (2) | C13—C14—C15—C16 | 1.3 (4) |
C2—C3—N4—Ni1 | −40.5 (2) | C13—C14—C15—N5 | −176.6 (2) |
N1—Ni1—N4—C5 | 141.5 (12) | O52—N5—C15—C16 | −179.1 (2) |
N1i—Ni1—N4—C5 | −38.5 (2) | O51—N5—C15—C16 | 1.0 (3) |
O11i—Ni1—N4—C5 | −132.1 (2) | O52—N5—C15—C14 | −1.1 (3) |
O11—Ni1—N4—C5 | 47.9 (2) | O51—N5—C15—C14 | 179.0 (2) |
N1—Ni1—N4—C3 | 14.1 (2) | C14—C15—C16—C11 | −0.9 (4) |
N1i—Ni1—N4—C3 | −165.9 (2) | N5—C15—C16—C11 | 177.0 (2) |
O11i—Ni1—N4—C3 | 100.4 (2) | C12—C11—C16—C15 | 0.0 (3) |
O11—Ni1—N4—C3 | −79.6 (2) | C17—C11—C16—C15 | −178.4 (2) |
C3—N4—C5—C6 | −179.8 (2) | Ni1—O11—C17—O12 | 5.5 (4) |
Ni1—N4—C5—C6 | 56.8 (3) | Ni1—O11—C17—C11 | −173.8 (2) |
N4—C5—C6—C7 | −71.0 (3) | C16—C11—C17—O12 | −11.8 (3) |
C5—C6—C7—N1i | 68.7 (3) | C12—C11—C17—O12 | 169.8 (2) |
N4—Ni1—O11—C17 | 121.4 (2) | C16—C11—C17—O11 | 167.5 (2) |
N4i—Ni1—O11—C17 | −58.6 (2) | C12—C11—C17—O11 | −10.9 (3) |
N1—Ni1—O11—C17 | 36.0 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12 | 0.91 | 2.33 | 3.056 (3) | 137 |
N4—H4···O52ii | 0.91 | 2.35 | 3.132 (3) | 144 |
C2—H2A···O12iii | 0.97 | 2.40 | 3.287 (4) | 152 |
Symmetry codes: (ii) x+1, y, z+1; (iii) −x, −y+1, −z+1. |
C24H32N6NiO8 | F(000) = 620 |
Mr = 591.27 | Dx = 1.555 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.8106 (3) Å | Cell parameters from 2781 reflections |
b = 8.4187 (2) Å | θ = 2.9–27.8° |
c = 12.8397 (4) Å | µ = 0.83 mm−1 |
β = 114.2543 (10)° | T = 150 K |
V = 1262.51 (6) Å3 | Block, colourless |
Z = 2 | 0.26 × 0.24 × 0.22 mm |
Kappa-CCD diffractometer | 2894 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2456 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
φ scans, and ω scans with κ offsets | θmax = 27.8°, θmin = 2.9° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→16 |
Tmin = 0.813, Tmax = 0.838 | k = 0→10 |
8828 measured reflections | l = −16→15 |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0314P)2 + 0.5307P] where P = (Fo2 + 2Fc2)/3 |
2894 reflections | (Δ/σ)max = 0.001 |
178 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.01595 (11) | |
N1 | 0.57282 (10) | 0.33040 (15) | 0.62464 (11) | 0.0193 (3) | |
C2 | 0.62427 (13) | 0.21138 (19) | 0.57574 (14) | 0.0228 (3) | |
C3 | 0.54312 (13) | 0.18189 (19) | 0.45225 (14) | 0.0226 (3) | |
N4 | 0.52317 (10) | 0.33495 (16) | 0.39076 (11) | 0.0195 (3) | |
C5 | 0.43331 (14) | 0.3272 (2) | 0.27367 (14) | 0.0238 (3) | |
C6 | 0.40728 (14) | 0.48956 (19) | 0.21559 (14) | 0.0236 (3) | |
C7 | 0.34781 (13) | 0.6063 (2) | 0.26408 (13) | 0.0217 (3) | |
O11 | 0.33036 (9) | 0.42120 (13) | 0.46359 (10) | 0.0218 (3) | |
O12 | 0.34942 (10) | 0.22940 (17) | 0.59137 (12) | 0.0410 (4) | |
O41 | −0.23591 (12) | 0.2008 (2) | 0.40490 (17) | 0.0595 (5) | |
O42 | −0.25454 (10) | 0.41423 (19) | 0.30553 (12) | 0.0423 (4) | |
N14 | −0.19596 (12) | 0.3093 (2) | 0.36853 (14) | 0.0343 (4) | |
C11 | 0.16301 (13) | 0.32350 (19) | 0.47697 (13) | 0.0195 (3) | |
C12 | 0.09284 (14) | 0.4217 (2) | 0.38919 (14) | 0.0239 (3) | |
C13 | −0.02574 (14) | 0.4187 (2) | 0.35172 (15) | 0.0262 (4) | |
C14 | −0.07089 (13) | 0.3137 (2) | 0.40536 (14) | 0.0250 (4) | |
C15 | −0.00398 (14) | 0.2141 (2) | 0.49259 (15) | 0.0271 (4) | |
C16 | 0.11389 (14) | 0.2198 (2) | 0.52871 (14) | 0.0245 (4) | |
C17 | 0.29251 (13) | 0.32381 (19) | 0.51547 (14) | 0.0210 (3) | |
H1 | 0.5135 | 0.2805 | 0.6359 | 0.023* | |
H2A | 0.6378 | 0.1112 | 0.6197 | 0.027* | |
H2B | 0.6987 | 0.2506 | 0.5798 | 0.027* | |
H3A | 0.5771 | 0.1043 | 0.4171 | 0.027* | |
H3B | 0.4698 | 0.1382 | 0.4482 | 0.027* | |
H4 | 0.5910 | 0.3615 | 0.3848 | 0.023* | |
H5A | 0.3625 | 0.2836 | 0.2760 | 0.029* | |
H5B | 0.4580 | 0.2538 | 0.2279 | 0.029* | |
H6A | 0.4801 | 0.5376 | 0.2217 | 0.028* | |
H6B | 0.3584 | 0.4740 | 0.1334 | 0.028* | |
H7A | 0.3159 | 0.6952 | 0.2098 | 0.026* | |
H7B | 0.2834 | 0.5521 | 0.2730 | 0.026* | |
H12 | 0.1264 | 0.4923 | 0.3540 | 0.029* | |
H13 | −0.0737 | 0.4861 | 0.2918 | 0.031* | |
H15 | −0.0380 | 0.1431 | 0.5272 | 0.032* | |
H16 | 0.1614 | 0.1527 | 0.5890 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.01204 (15) | 0.01563 (16) | 0.01780 (16) | −0.00064 (10) | 0.00373 (11) | 0.00118 (10) |
N1 | 0.0137 (6) | 0.0196 (6) | 0.0219 (7) | −0.0007 (5) | 0.0046 (5) | 0.0025 (5) |
C2 | 0.0186 (7) | 0.0188 (8) | 0.0283 (9) | 0.0026 (6) | 0.0068 (6) | 0.0035 (7) |
C3 | 0.0206 (7) | 0.0172 (8) | 0.0285 (9) | 0.0003 (6) | 0.0085 (7) | −0.0004 (6) |
N4 | 0.0139 (6) | 0.0207 (6) | 0.0219 (7) | −0.0022 (5) | 0.0054 (5) | −0.0004 (5) |
C5 | 0.0219 (8) | 0.0263 (8) | 0.0208 (8) | −0.0036 (7) | 0.0063 (6) | −0.0036 (7) |
C6 | 0.0206 (8) | 0.0294 (9) | 0.0190 (8) | −0.0025 (7) | 0.0062 (6) | 0.0013 (7) |
C7 | 0.0161 (7) | 0.0273 (8) | 0.0180 (8) | −0.0023 (6) | 0.0031 (6) | 0.0033 (6) |
O11 | 0.0147 (5) | 0.0245 (6) | 0.0244 (6) | −0.0033 (4) | 0.0062 (4) | 0.0030 (5) |
O12 | 0.0183 (6) | 0.0473 (8) | 0.0505 (9) | 0.0006 (6) | 0.0071 (6) | 0.0282 (7) |
O41 | 0.0273 (7) | 0.0675 (11) | 0.0894 (13) | −0.0090 (7) | 0.0297 (8) | 0.0087 (10) |
O42 | 0.0186 (6) | 0.0622 (10) | 0.0403 (8) | 0.0062 (6) | 0.0061 (6) | −0.0062 (7) |
N14 | 0.0184 (7) | 0.0482 (10) | 0.0376 (9) | −0.0038 (7) | 0.0128 (7) | −0.0118 (8) |
C11 | 0.0167 (7) | 0.0206 (8) | 0.0208 (8) | −0.0021 (6) | 0.0073 (6) | −0.0028 (6) |
C12 | 0.0193 (8) | 0.0258 (9) | 0.0267 (9) | −0.0018 (6) | 0.0094 (6) | 0.0008 (7) |
C13 | 0.0197 (8) | 0.0313 (10) | 0.0253 (9) | 0.0021 (7) | 0.0068 (6) | −0.0015 (7) |
C14 | 0.0148 (7) | 0.0332 (9) | 0.0280 (9) | −0.0030 (6) | 0.0097 (6) | −0.0103 (7) |
C15 | 0.0239 (8) | 0.0316 (9) | 0.0312 (9) | −0.0054 (7) | 0.0169 (7) | −0.0025 (7) |
C16 | 0.0222 (8) | 0.0276 (9) | 0.0245 (8) | −0.0025 (7) | 0.0104 (7) | 0.0004 (7) |
C17 | 0.0168 (7) | 0.0214 (8) | 0.0239 (8) | −0.0029 (6) | 0.0073 (6) | 0.0003 (6) |
Ni1—N1i | 2.060 (2) | C6—H6A | 0.99 |
Ni1—N1 | 2.060 (2) | C6—H6B | 0.99 |
Ni1—N4i | 2.080 (2) | C7—N1i | 1.472 (2) |
Ni1—N4 | 2.080 (2) | C7—H7A | 0.99 |
Ni1—O11i | 2.132 (2) | C7—H7B | 0.99 |
Ni1—O11 | 2.132 (2) | O11—C17 | 1.271 (2) |
N1—C7i | 1.472 (2) | O12—C17 | 1.237 (2) |
N1—C2 | 1.474 (2) | O41—N14 | 1.229 (2) |
N1—H1 | 0.93 | O42—N14 | 1.224 (2) |
C2—C3 | 1.517 (2) | N14—C14 | 1.473 (2) |
C2—H2A | 0.99 | C11—C12 | 1.389 (2) |
C2—H2B | 0.99 | C11—C16 | 1.394 (2) |
C3—N4 | 1.478 (2) | C11—C17 | 1.524 (2) |
C3—H3A | 0.99 | C12—C13 | 1.393 (2) |
C3—H3B | 0.99 | C12—H12 | 0.95 |
N4—C5 | 1.472 (2) | C13—C14 | 1.385 (2) |
N4—H4 | 0.93 | C13—H13 | 0.95 |
C5—C6 | 1.527 (2) | C14—C15 | 1.380 (3) |
C5—H5A | 0.99 | C15—C16 | 1.386 (2) |
C5—H5B | 0.99 | C15—H15 | 0.95 |
C6—C7 | 1.524 (2) | C16—H16 | 0.95 |
N1i—Ni1—N1 | 180.0 | C6—C5—H5A | 109.1 |
N1i—Ni1—N4i | 85.20 (5) | N4—C5—H5B | 109.1 |
N1—Ni1—N4i | 94.80 (5) | C6—C5—H5B | 109.1 |
N1i—Ni1—N4 | 94.80 (5) | H5A—C5—H5B | 107.9 |
N1—Ni1—N4 | 85.20 (5) | C7—C6—C5 | 115.04 (13) |
N4i—Ni1—N4 | 180.0 | C7—C6—H6A | 108.5 |
N1i—Ni1—O11i | 92.88 (5) | C5—C6—H6A | 108.5 |
N1—Ni1—O11i | 87.12 (5) | C7—C6—H6B | 108.5 |
N4i—Ni1—O11i | 93.39 (5) | C5—C6—H6B | 108.5 |
N4—Ni1—O11i | 86.61 (5) | H6A—C6—H6B | 107.5 |
N1i—Ni1—O11 | 87.12 (5) | N1i—C7—C6 | 111.6 (2) |
N1—Ni1—O11 | 92.88 (5) | N1i—C7—H7A | 109.3 |
N4i—Ni1—O11 | 86.61 (5) | C6—C7—H7A | 109.3 |
N4—Ni1—O11 | 93.39 (5) | N1i—C7—H7B | 109.3 |
O11i—Ni1—O11 | 180.0 | C6—C7—H7B | 109.3 |
C7i—N1—C2 | 114.1 (2) | H7A—C7—H7B | 108.0 |
C7i—N1—Ni1 | 114.5 (2) | C17—O11—Ni1 | 131.3 (2) |
C2—N1—Ni1 | 106.2 (2) | O42—N14—O41 | 123.3 (2) |
C7i—N1—H1 | 107.2 | O42—N14—C14 | 119.0 (2) |
C2—N1—H1 | 107.2 | O41—N14—C14 | 117.7 (2) |
Ni1—N1—H1 | 107.2 | C12—C11—C16 | 119.4 (2) |
N1—C2—C3 | 108.8 (2) | C12—C11—C17 | 121.2 (2) |
N1—C2—H2A | 109.9 | C16—C11—C17 | 119.4 (2) |
C3—C2—H2A | 109.9 | C11—C12—C13 | 121.3 (2) |
N1—C2—H2B | 109.9 | C11—C12—H12 | 119.3 |
C3—C2—H2B | 109.9 | C13—C12—H12 | 119.3 |
H2A—C2—H2B | 108.3 | C14—C13—C12 | 117.3 (2) |
N4—C3—C2 | 108.0 (2) | C14—C13—H13 | 121.3 |
N4—C3—H3A | 110.1 | C12—C13—H13 | 121.3 |
C2—C3—H3A | 110.1 | C15—C14—C13 | 123.0 (2) |
N4—C3—H3B | 110.1 | C15—C14—N14 | 118.5 (2) |
C2—C3—H3B | 110.1 | C13—C14—N14 | 118.5 (2) |
H3A—C3—H3B | 108.4 | C14—C15—C16 | 118.6 (2) |
C5—N4—C3 | 113.5 (2) | C14—C15—H15 | 120.7 |
C5—N4—Ni1 | 116.7 (2) | C16—C15—H15 | 120.7 |
C3—N4—Ni1 | 105.28 (9) | C15—C16—C11 | 120.4 (2) |
C5—N4—H4 | 106.9 | C15—C16—H16 | 119.8 |
C3—N4—H4 | 106.9 | C11—C16—H16 | 119.8 |
Ni1—N4—H4 | 106.9 | O12—C17—O11 | 126.8 (2) |
N4—C5—C6 | 112.4 (2) | O12—C17—C11 | 117.7 (2) |
N4—C5—H5A | 109.1 | O11—C17—C11 | 115.5 (2) |
N4i—Ni1—N1—C7i | −39.6 (12) | N1i—Ni1—O11—C17 | −169.7 (2) |
N4—Ni1—N1—C7i | 140.4 (2) | N1—Ni1—O11—C17 | 10.3 (12) |
O11i—Ni1—N1—C7i | 53.5 (2) | N4i—Ni1—O11—C17 | −84.3 (2) |
O11—Ni1—N1—C7i | −126.5 (2) | N4—Ni1—O11—C17 | 95.7 (2) |
N4i—Ni1—N1—C2 | −166.51 (9) | C16—C11—C12—C13 | 0.0 (2) |
N4—Ni1—N1—C2 | 13.49 (9) | C17—C11—C12—C13 | 178.3 (2) |
O11i—Ni1—N1—C2 | −73.34 (9) | C11—C12—C13—C14 | −0.1 (2) |
O11—Ni1—N1—C2 | 106.66 (9) | C12—C13—C14—C15 | 0.0 (3) |
C7i—N1—C2—C3 | −168.2 (2) | C12—C13—C14—N14 | 179.2 (2) |
Ni1—N1—C2—C3 | −41.1 (2) | O42—N14—C14—C15 | 167.8 (2) |
N1—C2—C3—N4 | 58.2 (11) | O41—N14—C14—C15 | −10.9 (2) |
C2—C3—N4—C5 | −172.0 (2) | O42—N14—C14—C13 | −11.5 (2) |
C2—C3—N4—Ni1 | −43.2 (2) | O41—N14—C14—C13 | 169.8 (2) |
N1i—Ni1—N4—C5 | −36.6 (2) | C13—C14—C15—C16 | 0.3 (3) |
N1—Ni1—N4—C5 | 143.4 (2) | N14—C14—C15—C16 | −178.9 (2) |
O11i—Ni1—N4—C5 | −129.2 (2) | C14—C15—C16—C11 | −0.5 (3) |
O11—Ni1—N4—C5 | 50.8 (2) | C12—C11—C16—C15 | 0.3 (2) |
N1i—Ni1—N4—C3 | −163.41 (9) | C17—C11—C16—C15 | −178.0 (2) |
N1—Ni1—N4—C3 | 16.59 (9) | Ni1—O11—C17—O12 | −13.3 (3) |
O11i—Ni1—N4—C3 | 103.98 (9) | Ni1—O11—C17—C11 | 167.9 (2) |
O11—Ni1—N4—C3 | −76.02 (9) | C12—C11—C17—O12 | −177.5 (2) |
C3—N4—C5—C6 | 175.1 (2) | C16—C11—C17—O12 | 0.8 (2) |
Ni1—N4—C5—C6 | 52.5 (2) | C12—C11—C17—O11 | 1.4 (2) |
N4—C5—C6—C7 | −69.4 (2) | C16—C11—C17—O11 | 179.6 (2) |
C5—C6—C7—N1i | 74.1 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12 | 0.93 | 1.99 | 2.845 (2) | 153 |
N4—H4···O41ii | 0.93 | 2.52 | 3.221 (2) | 132 |
C16—H16···O42iii | 0.95 | 2.60 | 3.439 (2) | 148 |
Symmetry codes: (ii) x+1, y, z; (iii) x+1/2, −y+1/2, z+1/2. |
C24H34N4NiO6 | F(000) = 564 |
Mr = 533.26 | Dx = 1.485 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5180 (3) Å | Cell parameters from 2748 reflections |
b = 13.2496 (5) Å | θ = 2.9–27.5° |
c = 10.7720 (4) Å | µ = 0.86 mm−1 |
β = 101.161 (2)° | T = 150 K |
V = 1192.74 (8) Å3 | Needle, colourless |
Z = 2 | 0.40 × 0.28 × 0.22 mm |
Kappa-CCD diffractometer | 2721 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2194 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→11 |
Tmin = 0.724, Tmax = 0.833 | k = 0→17 |
9996 measured reflections | l = −13→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0232P)2 + 0.6219P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2721 reflections | Δρmax = 0.33 e Å−3 |
162 parameters | Δρmin = −0.36 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0036 (10) |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.01498 (11) | |
N1 | 0.43833 (18) | 0.62473 (11) | 0.38455 (13) | 0.0188 (3) | |
C2 | 0.3062 (2) | 0.59176 (15) | 0.28307 (18) | 0.0254 (4) | |
C3 | 0.3435 (2) | 0.48667 (14) | 0.24034 (17) | 0.0255 (4) | |
N4 | 0.36826 (19) | 0.41851 (11) | 0.35181 (14) | 0.0205 (3) | |
C5 | 0.4336 (2) | 0.31855 (14) | 0.32804 (18) | 0.0249 (4) | |
C6 | 0.4585 (2) | 0.25182 (14) | 0.44562 (18) | 0.0267 (4) | |
C7 | 0.5968 (2) | 0.28196 (13) | 0.55099 (18) | 0.0236 (4) | |
O11 | 0.71243 (15) | 0.47431 (9) | 0.43020 (12) | 0.0211 (3) | |
O12 | 0.74555 (16) | 0.60133 (9) | 0.30107 (13) | 0.0256 (3) | |
O13 | 1.07609 (17) | 0.20467 (10) | 0.32970 (12) | 0.0275 (3) | |
C11 | 0.8565 (2) | 0.44052 (13) | 0.26869 (16) | 0.0184 (4) | |
C12 | 0.9286 (2) | 0.35489 (14) | 0.32983 (17) | 0.0200 (4) | |
C13 | 1.0080 (2) | 0.28633 (14) | 0.26516 (17) | 0.0197 (4) | |
C14 | 1.0144 (2) | 0.30365 (14) | 0.13851 (17) | 0.0219 (4) | |
C15 | 0.9400 (2) | 0.38830 (14) | 0.07732 (17) | 0.0226 (4) | |
C16 | 0.8619 (2) | 0.45748 (14) | 0.14164 (17) | 0.0213 (4) | |
C17 | 0.7665 (2) | 0.51106 (13) | 0.33895 (16) | 0.0180 (4) | |
H1 | 0.5252 | 0.6387 | 0.3466 | 0.023* | |
H2A | 0.2942 | 0.6393 | 0.2109 | 0.030* | |
H2B | 0.2046 | 0.5908 | 0.3148 | 0.030* | |
H3A | 0.2537 | 0.4618 | 0.1750 | 0.031* | |
H3B | 0.4411 | 0.4884 | 0.2033 | 0.031* | |
H4 | 0.2682 | 0.4073 | 0.3717 | 0.025* | |
H5A | 0.5371 | 0.3276 | 0.3006 | 0.030* | |
H5B | 0.3591 | 0.2846 | 0.2586 | 0.030* | |
H6A | 0.3588 | 0.2523 | 0.4800 | 0.032* | |
H6B | 0.4764 | 0.1817 | 0.4199 | 0.032* | |
H7A | 0.6187 | 0.2265 | 0.6136 | 0.028* | |
H7B | 0.6941 | 0.2923 | 0.5150 | 0.028* | |
H3 | 1.1246 | 0.1706 | 0.2831 | 0.041* | |
H12 | 0.9237 | 0.3431 | 0.4160 | 0.024* | |
H14 | 1.0695 | 0.2578 | 0.0942 | 0.026* | |
H15 | 0.9423 | 0.3991 | −0.0095 | 0.027* | |
H16 | 0.8127 | 0.5157 | 0.0994 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.01602 (17) | 0.01348 (17) | 0.01663 (16) | 0.00086 (13) | 0.00607 (11) | 0.00009 (12) |
N1 | 0.0184 (8) | 0.0183 (8) | 0.0217 (8) | 0.0016 (6) | 0.0087 (6) | 0.0025 (6) |
C2 | 0.0224 (10) | 0.0275 (10) | 0.0253 (10) | 0.0009 (8) | 0.0022 (8) | 0.0063 (8) |
C3 | 0.0260 (10) | 0.0296 (11) | 0.0199 (9) | −0.0043 (8) | 0.0017 (7) | 0.0000 (8) |
N4 | 0.0206 (8) | 0.0194 (8) | 0.0227 (8) | −0.0019 (6) | 0.0067 (6) | −0.0013 (6) |
C5 | 0.0306 (11) | 0.0195 (10) | 0.0261 (10) | −0.0043 (8) | 0.0096 (8) | −0.0086 (8) |
C6 | 0.0346 (11) | 0.0166 (9) | 0.0317 (11) | −0.0015 (8) | 0.0134 (9) | −0.0034 (8) |
C7 | 0.0285 (10) | 0.0161 (9) | 0.0292 (10) | 0.0081 (8) | 0.0127 (8) | 0.0041 (7) |
O11 | 0.0215 (7) | 0.0213 (7) | 0.0235 (6) | 0.0037 (5) | 0.0121 (5) | 0.0048 (5) |
O12 | 0.0286 (7) | 0.0158 (6) | 0.0372 (8) | 0.0029 (6) | 0.0181 (6) | 0.0042 (6) |
O13 | 0.0321 (8) | 0.0241 (7) | 0.0294 (7) | 0.0091 (6) | 0.0137 (6) | 0.0024 (6) |
C11 | 0.0175 (9) | 0.0175 (9) | 0.0216 (9) | −0.0023 (7) | 0.0072 (7) | 0.0002 (7) |
C12 | 0.0203 (9) | 0.0205 (9) | 0.0208 (9) | −0.0001 (7) | 0.0082 (7) | 0.0016 (7) |
C13 | 0.0183 (9) | 0.0164 (8) | 0.0254 (9) | −0.0010 (7) | 0.0067 (7) | 0.0004 (7) |
C14 | 0.0215 (9) | 0.0219 (9) | 0.0237 (9) | −0.0030 (8) | 0.0080 (7) | −0.0063 (8) |
C15 | 0.0244 (10) | 0.0250 (10) | 0.0194 (9) | −0.0026 (8) | 0.0070 (7) | −0.0011 (7) |
C16 | 0.0221 (9) | 0.0188 (9) | 0.0238 (9) | −0.0010 (8) | 0.0062 (7) | 0.0024 (7) |
C17 | 0.0164 (8) | 0.0176 (9) | 0.0207 (8) | 0.0000 (7) | 0.0054 (7) | 0.0006 (7) |
Ni1—N4 | 2.069 (2) | C6—H6A | 0.99 |
Ni1—N4i | 2.069 (2) | C6—H6B | 0.99 |
Ni1—N1 | 2.074 (2) | C7—N1i | 1.477 (2) |
Ni1—N1i | 2.074 (2) | C7—H7A | 0.99 |
Ni1—O11i | 2.117 (2) | C7—H7B | 0.99 |
Ni1—O11 | 2.117 (2) | O11—C17 | 1.261 (2) |
N1—C2 | 1.475 (2) | O12—C17 | 1.265 (2) |
N1—C7i | 1.477 (2) | O13—C13 | 1.354 (2) |
N1—H1 | 0.93 | O13—H3 | 0.84 |
C2—C3 | 1.519 (3) | C11—C12 | 1.393 (3) |
C2—H2A | 0.99 | C11—C16 | 1.396 (2) |
C2—H2B | 0.99 | C11—C17 | 1.503 (2) |
C3—N4 | 1.485 (2) | C12—C13 | 1.397 (2) |
C3—H3A | 0.99 | C12—H12 | 0.95 |
C3—H3B | 0.99 | C13—C14 | 1.395 (2) |
N4—C5 | 1.478 (2) | C14—C15 | 1.390 (3) |
N4—H4 | 0.93 | C14—H14 | 0.95 |
C5—C6 | 1.525 (3) | C15—C16 | 1.393 (3) |
C5—H5A | 0.99 | C15—H15 | 0.95 |
C5—H5B | 0.99 | C16—H16 | 0.95 |
C6—C7 | 1.523 (3) | ||
N4—Ni1—N4i | 180.0 | N4—C5—H5A | 109.2 |
N4—Ni1—N1 | 85.22 (6) | C6—C5—H5A | 109.2 |
N4i—Ni1—N1 | 94.78 (6) | N4—C5—H5B | 109.2 |
N4—Ni1—N1i | 94.78 (6) | C6—C5—H5B | 109.2 |
N4i—Ni1—N1i | 85.22 (6) | H5A—C5—H5B | 107.9 |
N1—Ni1—N1i | 180.0 | C7—C6—C5 | 115.5 (2) |
N4—Ni1—O11i | 89.12 (6) | C7—C6—H6A | 108.4 |
N4i—Ni1—O11i | 90.88 (6) | C5—C6—H6A | 108.4 |
N1—Ni1—O11i | 87.14 (5) | C7—C6—H6B | 108.4 |
N1i—Ni1—O11i | 92.86 (5) | C5—C6—H6B | 108.4 |
N4—Ni1—O11 | 90.88 (6) | H6A—C6—H6B | 107.5 |
N4i—Ni1—O11 | 89.12 (6) | N1i—C7—C6 | 111.8 (2) |
N1—Ni1—O11 | 92.86 (5) | N1i—C7—H7A | 109.2 |
N1i—Ni1—O11 | 87.14 (5) | C6—C7—H7A | 109.2 |
O11i—Ni1—O11 | 180.0 | N1i—C7—H7B | 109.2 |
C2—N1—C7i | 113.7 (2) | C6—C7—H7B | 109.2 |
C2—N1—Ni1 | 106.1 (2) | H7A—C7—H7B | 107.9 |
C7i—N1—Ni1 | 115.9 (2) | C17—O11—Ni1 | 132.9 (2) |
C2—N1—H1 | 106.9 | C13—O13—H3 | 109.5 |
C7i—N1—H1 | 106.9 | C12—C11—C16 | 120.0 (2) |
Ni1—N1—H1 | 106.9 | C12—C11—C17 | 119.3 (2) |
N1—C2—C3 | 108.8 (2) | C16—C11—C17 | 120.7 (12) |
N1—C2—H2A | 109.9 | C11—C12—C13 | 120.4 (2) |
C3—C2—H2A | 109.9 | C11—C12—H12 | 119.8 |
N1—C2—H2B | 109.9 | C13—C12—H12 | 119.8 |
C3—C2—H2B | 109.9 | O13—C13—C14 | 122.7 (2) |
H2A—C2—H2B | 108.3 | O13—C13—C12 | 117.7 (2) |
N4—C3—C2 | 108.5 (2) | C14—C13—C12 | 119.7 (2) |
N4—C3—H3A | 110.0 | C15—C14—C13 | 119.7 (2) |
C2—C3—H3A | 110.0 | C15—C14—H14 | 120.1 |
N4—C3—H3B | 110.0 | C13—C14—H14 | 120.1 |
C2—C3—H3B | 110.0 | C14—C15—C16 | 120.9 (2) |
H3A—C3—H3B | 108.4 | C14—C15—H15 | 119.6 |
C5—N4—C3 | 113.9 (2) | C16—C15—H15 | 119.6 |
C5—N4—Ni1 | 115.8 (2) | C15—C16—C11 | 119.4 (2) |
C3—N4—Ni1 | 106.1 (2) | C15—C16—H16 | 120.3 |
C5—N4—H4 | 106.9 | C11—C16—H16 | 120.3 |
C3—N4—H4 | 106.9 | O11—C17—O12 | 124.5 (2) |
Ni1—N4—H4 | 106.9 | O11—C17—C11 | 116.8 (2) |
N4—C5—C6 | 111.8 (2) | O12—C17—C11 | 118.6 (2) |
N4—Ni1—N1—C2 | 14.9 (2) | N4—C5—C6—C7 | −71.9 (2) |
N4i—Ni1—N1—C2 | −165.1 (2) | C5—C6—C7—N1i | 71.7 (2) |
O11i—Ni1—N1—C2 | −74.4 (2) | N4—Ni1—O11—C17 | 75.4 (2) |
O11—Ni1—N1—C2 | 105.6 (2) | N4i—Ni1—O11—C17 | −104.6 (2) |
N4—Ni1—N1—C7i | 142.1 (2) | N1—Ni1—O11—C17 | −9.9 (2) |
N4i—Ni1—N1—C7i | −38.0 (2) | N1i—Ni1—O11—C17 | 170.1 (2) |
O11i—Ni1—N1—C7i | 52.7 (2) | C16—C11—C12—C13 | 0.8 (3) |
O11—Ni1—N1—C7i | −127.3 (2) | C17—C11—C12—C13 | 177.7 (2) |
C7i—N1—C2—C3 | −167.0 (2) | C11—C12—C13—O13 | 179.8 (2) |
Ni1—N1—C2—C3 | −41.5 (2) | C11—C12—C13—C14 | −0.3 (3) |
N1—C2—C3—N4 | 56.9 (2) | O13—C13—C14—C15 | 179.1 (2) |
C2—C3—N4—C5 | −169.7 (2) | C12—C13—C14—C15 | −0.8 (3) |
C2—C3—N4—Ni1 | −41.1 (2) | C13—C14—C15—C16 | 1.5 (3) |
N1—Ni1—N4—C5 | 142.0 (2) | C14—C15—C16—C11 | −1.0 (3) |
N1i—Ni1—N4—C5 | −38.0 (2) | C12—C11—C16—C15 | −0.1 (3) |
O11i—Ni1—N4—C5 | −130.832) | C17—C11—C16—C15 | −177.0 (2) |
O11—Ni1—N4—C5 | 49.2 (2) | Ni1—O11—C17—O12 | 34.1 (3) |
N1—Ni1—N4—C3 | 14.6 (2) | Ni1—O11—C17—C11 | −143.6 (2) |
N1i—Ni1—N4—C3 | −165.4 (2) | C12—C11—C17—O11 | −24.2 (2) |
O11i—Ni1—N4—C3 | 101.8 (2) | C16—C11—C17—O11 | 152.7 (2) |
O11—Ni1—N4—C3 | −78.2 (2) | C12—C11—C17—O12 | 157.9 (2) |
C3—N4—C5—C6 | 179.4 (2) | C16—C11—C17—O12 | −25.1 (3) |
Ni1—N4—C5—C6 | 56.0 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12 | 0.93 | 2.09 | 2.943 (2) | 152 |
O13—H3···O12ii | 0.84 | 1.81 | 2.645 (2) | 172 |
Symmetry code: (ii) −x+2, y−1/2, −z+1/2. |
C24H36N6NiO4 | F(000) = 1128 |
Mr = 531.30 | Dx = 1.420 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.4430 (4) Å | Cell parameters from 2913 reflections |
b = 8.4149 (2) Å | θ = 2.8–27.5° |
c = 16.8262 (4) Å | µ = 0.82 mm−1 |
β = 107.8774 (14)° | T = 150 K |
V = 2485.27 (10) Å3 | Block, colourless |
Z = 4 | 0.42 × 0.40 × 0.38 mm |
Kappa-CCD diffractometer | 2823 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2395 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→23 |
Tmin = 0.724, Tmax = 0.745 | k = 0→10 |
12342 measured reflections | l = −21→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
wR(F2) = 0.074 | w = 1/[σ2(Fo2) + (0.0282P)2 + 2.6861P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2823 reflections | Δρmax = 0.32 e Å−3 |
161 parameters | Δρmin = −0.34 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0023 (3) |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.01544 (10) | |
N1 | 0.55981 (7) | 0.42978 (16) | 0.42106 (8) | 0.0203 (3) | |
C2 | 0.50599 (10) | 0.3387 (2) | 0.35408 (10) | 0.0266 (4) | |
C3 | 0.45702 (11) | 0.2348 (2) | 0.39085 (11) | 0.0294 (4) | |
N4 | 0.41827 (8) | 0.33600 (16) | 0.43749 (8) | 0.0238 (3) | |
C5 | 0.38198 (10) | 0.2450 (2) | 0.49033 (12) | 0.0316 (4) | |
C6 | 0.34463 (10) | 0.3531 (2) | 0.53936 (12) | 0.0323 (4) | |
C7 | 0.39919 (10) | 0.4466 (2) | 0.60996 (11) | 0.0270 (4) | |
O11 | 0.55427 (6) | 0.32521 (13) | 0.58986 (7) | 0.0219 (2) | |
O12 | 0.64821 (6) | 0.21858 (14) | 0.54774 (7) | 0.0231 (3) | |
N14 | 0.69692 (8) | −0.14447 (18) | 0.89459 (9) | 0.0283 (3) | |
C11 | 0.63534 (8) | 0.13716 (17) | 0.67784 (9) | 0.0165 (3) | |
C12 | 0.59138 (9) | 0.13522 (18) | 0.73217 (9) | 0.0186 (3) | |
C13 | 0.61119 (9) | 0.04265 (19) | 0.80356 (10) | 0.0206 (3) | |
C14 | 0.67787 (9) | −0.04965 (19) | 0.82489 (10) | 0.0201 (3) | |
C15 | 0.72308 (9) | −0.0451 (2) | 0.77074 (10) | 0.0224 (3) | |
C16 | 0.70153 (9) | 0.04533 (19) | 0.69872 (10) | 0.0201 (3) | |
C17 | 0.61086 (8) | 0.23363 (18) | 0.59906 (9) | 0.0170 (3) | |
H1 | 0.5964 | 0.3580 | 0.4509 | 0.024* | |
H2A | 0.5343 | 0.2714 | 0.3255 | 0.032* | |
H2B | 0.4732 | 0.4123 | 0.3125 | 0.032* | |
H3A | 0.4187 | 0.1778 | 0.3456 | 0.035* | |
H3B | 0.4893 | 0.1550 | 0.4289 | 0.035* | |
H4 | 0.3800 | 0.3916 | 0.3984 | 0.029* | |
H5A | 0.4210 | 0.1784 | 0.5299 | 0.038* | |
H5B | 0.3429 | 0.1732 | 0.4545 | 0.038* | |
H6A | 0.3112 | 0.4293 | 0.4999 | 0.039* | |
H6B | 0.3118 | 0.2871 | 0.5630 | 0.039* | |
H7A | 0.3702 | 0.4970 | 0.6439 | 0.032* | |
H7B | 0.4366 | 0.3727 | 0.6465 | 0.032* | |
H14A | 0.6672 | −0.1481 | 0.9267 | 0.034* | |
H14B | 0.7389 | −0.2017 | 0.9072 | 0.034* | |
H12 | 0.5468 | 0.1990 | 0.7198 | 0.022* | |
H13 | 0.5794 | 0.0415 | 0.8385 | 0.025* | |
H15 | 0.7689 | −0.1050 | 0.7840 | 0.027* | |
H16 | 0.7324 | 0.0450 | 0.6627 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.01769 (15) | 0.01486 (15) | 0.01392 (14) | −0.00007 (10) | 0.00506 (10) | 0.00034 (10) |
N1 | 0.0242 (7) | 0.0204 (7) | 0.0174 (6) | 0.0045 (5) | 0.0080 (5) | 0.0032 (5) |
C2 | 0.0369 (10) | 0.0260 (9) | 0.0164 (7) | 0.0046 (7) | 0.0074 (7) | −0.0014 (6) |
C3 | 0.0401 (10) | 0.0217 (8) | 0.0235 (8) | −0.0040 (7) | 0.0056 (7) | −0.0069 (7) |
N4 | 0.0257 (7) | 0.0216 (7) | 0.0216 (7) | −0.0041 (5) | 0.0036 (6) | 0.0004 (5) |
C5 | 0.0318 (9) | 0.0281 (9) | 0.0341 (9) | −0.0107 (7) | 0.0090 (8) | 0.0034 (8) |
C6 | 0.0232 (8) | 0.0365 (10) | 0.0382 (10) | −0.0031 (7) | 0.0110 (7) | 0.0109 (8) |
C7 | 0.0266 (8) | 0.0328 (9) | 0.0264 (8) | 0.0052 (7) | 0.0152 (7) | 0.0088 (7) |
O11 | 0.0231 (6) | 0.0230 (6) | 0.0207 (5) | 0.0071 (4) | 0.0083 (4) | 0.0062 (4) |
O12 | 0.0229 (6) | 0.0303 (6) | 0.0183 (5) | 0.0043 (5) | 0.0098 (4) | 0.0039 (5) |
N14 | 0.0264 (7) | 0.0360 (8) | 0.0248 (7) | 0.0096 (6) | 0.0113 (6) | 0.0143 (6) |
C11 | 0.0174 (7) | 0.0156 (7) | 0.0163 (7) | −0.0017 (5) | 0.0047 (6) | −0.0010 (6) |
C12 | 0.0191 (7) | 0.0176 (7) | 0.0199 (7) | 0.0019 (6) | 0.0070 (6) | −0.0009 (6) |
C13 | 0.0229 (8) | 0.0221 (8) | 0.0192 (7) | 0.0007 (6) | 0.0100 (6) | −0.0001 (6) |
C14 | 0.0218 (8) | 0.0187 (7) | 0.0191 (7) | −0.0005 (6) | 0.0053 (6) | 0.0021 (6) |
C15 | 0.0186 (7) | 0.0245 (8) | 0.0243 (8) | 0.0048 (6) | 0.0069 (6) | 0.0052 (6) |
C16 | 0.0187 (7) | 0.0223 (8) | 0.0215 (8) | 0.0002 (6) | 0.0093 (6) | 0.0014 (6) |
C17 | 0.0173 (7) | 0.0159 (7) | 0.0166 (7) | −0.0016 (6) | 0.0034 (5) | −0.0005 (6) |
Ni1—N1i | 2.057 (2) | C6—H6A | 0.99 |
Ni1—N1 | 2.057 (2) | C6—H6B | 0.99 |
Ni1—N4i | 2.076 (2) | C7—N1i | 1.473 (2) |
Ni1—N4 | 2.076 (2) | C7—H7A | 0.99 |
Ni1—O11i | 2.127 (2) | C7—H7B | 0.99 |
Ni1—O11 | 2.127 (2) | O11—C17 | 1.268 (2) |
N1—C2 | 1.468 (2) | O12—C17 | 1.266 (2) |
N1—C7i | 1.473 (2) | N14—C14 | 1.372 (2) |
N1—H1 | 0.93 | N14—H14A | 0.88 |
C2—C3 | 1.518 (2) | N14—H14B | 0.88 |
C2—H2A | 0.99 | C11—C16 | 1.395 (2) |
C2—H2B | 0.99 | C11—C12 | 1.396 (2) |
C3—N4 | 1.482 (2) | C11—C17 | 1.501 (2) |
C3—H3A | 0.99 | C12—C13 | 1.383 (2) |
C3—H3B | 0.99 | C12—H12 | 0.95 |
N4—C5 | 1.480 (2) | C13—C14 | 1.405 (2) |
N4—H4 | 0.93 | C13—H13 | 0.95 |
C5—C6 | 1.527 (3) | C14—C15 | 1.412 (2) |
C5—H5A | 0.99 | C15—C16 | 1.382 (2) |
C5—H5B | 0.99 | C15—H15 | 0.95 |
C6—C7 | 1.519 (3) | C16—H16 | 0.95 |
N1i—Ni1—N1 | 180.0 | C6—C5—H5A | 109.2 |
N1i—Ni1—N4i | 86.08 (5) | N4—C5—H5B | 109.2 |
N1—Ni1—N4i | 93.92 (5) | C6—C5—H5B | 109.2 |
N1i—Ni1—N4 | 93.92 (5) | H5A—C5—H5B | 107.9 |
N1—Ni1—N4 | 86.08 (5) | C7—C6—C5 | 115.5 (2) |
N4i—Ni1—N4 | 180.0 | C7—C6—H6A | 108.4 |
N1i—Ni1—O11i | 91.83 (5) | C5—C6—H6A | 108.4 |
N1—Ni1—O11i | 88.18 (5) | C7—C6—H6B | 108.4 |
N4i—Ni1—O11i | 90.60 (5) | C5—C6—H6B | 108.4 |
N4—Ni1—O11i | 89.40 (5) | H6A—C6—H6B | 107.5 |
N1i—Ni1—O11 | 88.18 (5) | N1i—C7—C6 | 112.2 (2) |
N1—Ni1—O11 | 91.82 (5) | N1i—C7—H7A | 109.2 |
N4i—Ni1—O11 | 89.40 (5) | C6—C7—H7A | 109.2 |
N4—Ni1—O11 | 90.60 (5) | N1i—C7—H7B | 109.2 |
O11i—Ni1—O11 | 180.0 | C6—C7—H7B | 109.2 |
C2—N1—C7i | 113.4 (2) | H7A—C7—H7B | 107.9 |
C2—N1—Ni1 | 106.0 (2) | C17—O11—Ni1 | 134.2 (2) |
C7i—N1—Ni1 | 117.5 (2) | C14—N14—H14A | 120.0 |
C2—N1—H1 | 106.4 | C14—N14—H14B | 120.0 |
C7i—N1—H1 | 106.4 | H14A—N14—H14B | 120.0 |
Ni1—N1—H1 | 106.4 | C16—C11—C12 | 117.9 (12) |
N1—C2—C3 | 109.5 (2) | C16—C11—C17 | 121.7 (2) |
N1—C2—H2A | 109.8 | C12—C11—C17 | 120.45 (2) |
C3—C2—H2A | 109.8 | C13—C12—C11 | 121.6 (2) |
N1—C2—H2B | 109.8 | C13—C12—H12 | 119.2 |
C3—C2—H2B | 109.8 | C11—C12—H12 | 119.2 |
H2A—C2—H2B | 108.2 | C12—C13—C14 | 120.7 (2) |
N4—C3—C2 | 109.2 (2) | C12—C13—H13 | 119.7 |
N4—C3—H3A | 109.8 | C14—C13—H13 | 119.7 |
C2—C3—H3A | 109.8 | N14—C14—C13 | 120.9 (2) |
N4—C3—H3B | 109.8 | N14—C14—C15 | 121.4 (2) |
C2—C3—H3B | 109.8 | C13—C14—C15 | 117.7 (2) |
H3A—C3—H3B | 108.3 | C16—C15—C14 | 120.9 (2) |
C5—N4—C3 | 113.7 (2) | C16—C15—H15 | 119.6 |
C5—N4—Ni1 | 115.6 (2) | C14—C15—H15 | 119.6 |
C3—N4—Ni1 | 104.9 (2) | C15—C16—C11 | 121.3 (2) |
C5—N4—H4 | 107.4 | C15—C16—H16 | 119.3 |
C3—N4—H4 | 107.4 | C11—C16—H16 | 119.3 |
Ni1—N4—H4 | 107.4 | O12—C17—O11 | 125.3 (2) |
N4—C5—C6 | 112.2 (2) | O12—C17—C11 | 118.0 (2) |
N4—C5—H5A | 109.2 | O11—C17—C11 | 116.7 (2) |
N4i—Ni1—N1—C2 | −166.3 (2) | N4—C5—C6—C7 | −70.8 (2) |
N4—Ni1—N1—C2 | 13.7 (2) | C5—C6—C7—N1i | 69.0 (2) |
O11i—Ni1—N1—C2 | −75.8 (2) | N1i—Ni1—O11—C17 | −168.7 (2) |
O11—Ni1—N1—C2 | 104.2 (2) | N1—Ni1—O11—C17 | 11.4 (2) |
N4i—Ni1—N1—C7i | −38.4 (2) | N4i—Ni1—O11—C17 | −82.6 (2) |
N4—Ni1—N1—C7i | 141.6 (2) | N4—Ni1—O11—C17 | 97.5 (2) |
O11i—Ni1—N1—C7i | 52.1 (2) | C16—C11—C12—C13 | −1.6 (2) |
O11—Ni1—N1—C7i | −127.9 (2) | C17—C11—C12—C13 | 177.5 (2) |
C7i—N1—C2—C3 | −170.3 (2) | C11—C12—C13—C14 | 1.8 (2) |
Ni1—N1—C2—C3 | −40.0 (2) | C12—C13—C14—N14 | −178.5 (2) |
N1—C2—C3—N4 | 56.3 (2) | C12—C13—C14—C15 | −0.5 (2) |
C2—C3—N4—C5 | −168.0 (2) | N14—C14—C15—C16 | 177.1 (2) |
C2—C3—N4—Ni1 | −40.8 (2) | C13—C14—C15—C16 | −1.0 (2) |
N1i—Ni1—N4—C5 | −39.0 (2) | C14—C15—C16—C11 | 1.1 (3) |
N1—Ni1—N4—C5 | 141.1 (1) | C12—C11—C16—C15 | 0.1 (2) |
O11i—Ni1—N4—C5 | −130.7 (2) | C17—C11—C16—C15 | −179.0 (2) |
O11—Ni1—N4—C5 | 49.3 (2) | Ni1—O11—C17—O12 | −5.3 (2) |
N1i—Ni1—N4—C3 | −164.9 (2) | Ni1—O11—C17—C11 | 174.1 (2) |
N1—Ni1—N4—C3 | 15.1 (2) | C16—C11—C17—O12 | 6.3 (2) |
O11i—Ni1—N4—C3 | 103.3 (2) | C12—C11—C17—O12 | −172.8 (2) |
O11—Ni1—N4—C3 | −76.7 (2) | C16—C11—C17—O11 | −173.1 (2) |
C3—N4—C5—C6 | 178.3 (2) | C12—C11—C17—O11 | 7.8 (2) |
Ni1—N4—C5—C6 | 57.0 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12 | 0.93 | 2.00 | 2.868 (2) | 155 |
N14—H14A···O12ii | 0.88 | 2.25 | 3.043 (2) | 150 |
N14—H14B···O12iii | 0.88 | 2.10 | 2.954 (2) | 165 |
Symmetry codes: (ii) x, −y, z+1/2; (iii) −x+3/2, y−1/2, −z+3/2. |
C18H30N4NiO6·4(H2O) | F(000) = 1128 |
Mr = 529.23 | Dx = 1.474 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 18.4057 (8) Å | Cell parameters from 2739 reflections |
b = 9.6927 (4) Å | θ = 2.8–27.5° |
c = 13.4648 (5) Å | µ = 0.87 mm−1 |
β = 96.724 (2)° | T = 150 K |
V = 2385.61 (17) Å3 | Plate, purple |
Z = 4 | 0.36 × 0.34 × 0.04 mm |
Kappa-CCD diffractometer | 5106 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 4757 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −23→23 |
Tmin = 0.744, Tmax = 0.966 | k = −12→12 |
9912 measured reflections | l = −17→17 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2)P)2 + 2.7841P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.082 | (Δ/σ)max = 0.009 |
S = 1.03 | Δρmax = 0.35 e Å−3 |
5106 reflections | Δρmin = −0.36 e Å−3 |
342 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
12 restraints | Extinction coefficient: 0.0014 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 2357 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.434 (11) |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.500367 (18) | 0.19694 (3) | 0.50001 (2) | 0.01553 (9) | |
N1 | 0.51041 (13) | 0.0522 (2) | 0.38875 (16) | 0.0181 (5) | |
C2 | 0.57352 (16) | 0.0933 (4) | 0.3380 (2) | 0.0239 (6) | |
C3 | 0.57334 (16) | 0.2497 (4) | 0.3287 (2) | 0.0221 (6) | |
N4 | 0.57657 (13) | 0.3102 (2) | 0.43020 (16) | 0.0204 (5) | |
C5 | 0.56531 (18) | 0.4616 (3) | 0.4298 (2) | 0.0267 (6) | |
C6 | 0.56375 (18) | 0.5197 (3) | 0.5343 (2) | 0.0279 (6) | |
C7 | 0.49540 (17) | 0.4861 (3) | 0.5834 (2) | 0.0240 (6) | |
N8 | 0.49288 (13) | 0.3398 (2) | 0.61357 (16) | 0.0192 (5) | |
C9 | 0.42410 (18) | 0.3013 (3) | 0.6536 (2) | 0.0243 (7) | |
C10 | 0.42015 (17) | 0.1450 (4) | 0.6640 (2) | 0.0248 (7) | |
N11 | 0.42452 (13) | 0.0827 (2) | 0.56478 (16) | 0.0187 (5) | |
C12 | 0.43508 (17) | −0.0686 (3) | 0.5693 (2) | 0.0249 (6) | |
C13 | 0.44081 (17) | −0.1301 (3) | 0.4667 (2) | 0.0240 (6) | |
C14 | 0.51042 (16) | −0.0937 (3) | 0.4208 (2) | 0.0226 (6) | |
O1 | 0.41696 (11) | 0.3069 (2) | 0.41743 (13) | 0.0200 (4) | |
O2 | 0.37648 (11) | 0.1701 (2) | 0.28844 (14) | 0.0227 (4) | |
O3 | 0.25257 (12) | 0.7176 (2) | 0.47024 (14) | 0.0234 (4) | |
O4 | 0.24784 (12) | 0.8581 (2) | 0.34041 (14) | 0.0239 (4) | |
O5 | 0.22645 (11) | 0.5052 (2) | 0.05556 (13) | 0.0194 (4) | |
C21 | 0.33005 (14) | 0.3993 (3) | 0.29374 (19) | 0.0173 (5) | |
C22 | 0.31571 (15) | 0.5105 (3) | 0.35362 (18) | 0.0169 (5) | |
C23 | 0.27343 (14) | 0.6215 (3) | 0.31330 (18) | 0.0156 (5) | |
C24 | 0.24506 (15) | 0.6192 (3) | 0.2125 (2) | 0.0171 (5) | |
C25 | 0.25802 (14) | 0.5062 (3) | 0.15356 (18) | 0.0151 (5) | |
C26 | 0.30025 (14) | 0.3959 (3) | 0.19354 (18) | 0.0164 (5) | |
C27 | 0.37760 (15) | 0.2817 (3) | 0.33636 (18) | 0.0168 (5) | |
C28 | 0.25685 (14) | 0.7408 (3) | 0.37872 (18) | 0.0164 (5) | |
O6 | 0.58776 (11) | 0.0983 (2) | 0.59862 (14) | 0.0214 (4) | |
O7 | 0.63580 (12) | 0.2779 (2) | 0.74172 (16) | 0.0275 (5) | |
O8 | 0.67775 (13) | 0.2377 (2) | 0.93999 (15) | 0.0287 (5) | |
O9 | 0.76311 (12) | 0.4569 (2) | 1.00127 (16) | 0.0254 (4) | |
O10 | 0.75061 (12) | 0.5538 (2) | 1.19632 (14) | 0.0247 (4) | |
H1 | 0.4694 | 0.0630 | 0.3421 | 0.022* | |
H2A | 0.5701 | 0.0506 | 0.2708 | 0.029* | |
H2B | 0.6195 | 0.0620 | 0.3770 | 0.029* | |
H3A | 0.6161 | 0.2804 | 0.2962 | 0.027* | |
H3B | 0.5283 | 0.2806 | 0.2872 | 0.027* | |
H4 | 0.6227 | 0.2922 | 0.4636 | 0.025* | |
H5A | 0.5185 | 0.4836 | 0.3888 | 0.032* | |
H5B | 0.6052 | 0.5066 | 0.3984 | 0.032* | |
H6C | 0.5687 | 0.6212 | 0.5311 | 0.034* | |
H6D | 0.6069 | 0.4841 | 0.5776 | 0.034* | |
H7C | 0.4941 | 0.5453 | 0.6431 | 0.029* | |
H7D | 0.4516 | 0.5074 | 0.5360 | 0.029* | |
H8 | 0.5315 | 0.3241 | 0.6633 | 0.023* | |
H9C | 0.3817 | 0.3346 | 0.6079 | 0.029* | |
H9D | 0.4224 | 0.3452 | 0.7197 | 0.029* | |
H10C | 0.4612 | 0.1118 | 0.7122 | 0.030* | |
H10D | 0.3736 | 0.1185 | 0.6890 | 0.030* | |
H11 | 0.3796 | 0.0983 | 0.5272 | 0.022* | |
H12A | 0.3934 | −0.1116 | 0.5980 | 0.030* | |
H12B | 0.4802 | −0.0899 | 0.6141 | 0.030* | |
H13A | 0.3982 | −0.0989 | 0.4205 | 0.029* | |
H13B | 0.4377 | −0.2318 | 0.4718 | 0.029* | |
H14A | 0.5535 | −0.1108 | 0.4706 | 0.027* | |
H14B | 0.5146 | −0.1541 | 0.3625 | 0.027* | |
H5 | 0.2404 | 0.4350 | 0.0265 | 0.029* | |
H22 | 0.3347 | 0.5113 | 0.4223 | 0.020* | |
H24 | 0.2169 | 0.6948 | 0.1843 | 0.020* | |
H26 | 0.3087 | 0.3189 | 0.1529 | 0.020* | |
H6A | 0.609 (2) | 0.143 (4) | 0.653 (3) | 0.052 (13)* | |
H6B | 0.6248 (18) | 0.050 (4) | 0.577 (3) | 0.040 (11)* | |
H7A | 0.641 (2) | 0.259 (4) | 0.804 (2) | 0.038 (11)* | |
H7B | 0.670 (2) | 0.334 (4) | 0.722 (3) | 0.040 (11)* | |
H8A | 0.710 (2) | 0.301 (4) | 0.960 (3) | 0.050 (13)* | |
H8B | 0.697 (3) | 0.163 (4) | 0.968 (4) | 0.068 (15)* | |
H9A | 0.758 (2) | 0.489 (4) | 1.059 (2) | 0.035 (10)* | |
H9B | 0.758 (2) | 0.520 (3) | 0.954 (2) | 0.030 (10)* | |
H10A | 0.7918 (17) | 0.602 (3) | 1.222 (2) | 0.026 (8)* | |
H10B | 0.752 (4) | 0.489 (5) | 1.240 (4) | 0.11 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.01649 (15) | 0.01509 (14) | 0.01473 (14) | 0.00102 (14) | 0.00067 (10) | 0.00032 (14) |
N1 | 0.0179 (11) | 0.0185 (12) | 0.0174 (10) | 0.0016 (9) | −0.0008 (8) | −0.0020 (9) |
C2 | 0.0197 (14) | 0.0314 (17) | 0.0206 (13) | 0.0033 (13) | 0.0029 (11) | −0.0047 (12) |
C3 | 0.0221 (15) | 0.0310 (18) | 0.0138 (13) | 0.0012 (14) | 0.0049 (11) | 0.0006 (12) |
N4 | 0.0203 (12) | 0.0200 (12) | 0.0207 (11) | −0.0014 (10) | 0.0011 (9) | 0.0013 (9) |
C5 | 0.0324 (17) | 0.0196 (15) | 0.0278 (15) | −0.0018 (13) | 0.0025 (12) | 0.0042 (11) |
C6 | 0.0303 (16) | 0.0212 (15) | 0.0312 (15) | −0.0039 (13) | −0.0011 (12) | 0.0016 (12) |
C7 | 0.0285 (16) | 0.0176 (14) | 0.0249 (14) | 0.0008 (12) | −0.0012 (11) | −0.0039 (11) |
N8 | 0.0187 (11) | 0.0195 (12) | 0.0188 (11) | 0.0027 (9) | −0.0006 (9) | −0.0015 (9) |
C9 | 0.0240 (15) | 0.0294 (18) | 0.0202 (14) | 0.0042 (13) | 0.0055 (11) | −0.0042 (12) |
C10 | 0.0236 (15) | 0.0304 (18) | 0.0219 (14) | −0.0018 (14) | 0.0084 (11) | 0.0021 (13) |
N11 | 0.0191 (11) | 0.0182 (11) | 0.0184 (10) | −0.0001 (10) | 0.0005 (8) | 0.0020 (9) |
C12 | 0.0271 (15) | 0.0189 (14) | 0.0288 (14) | −0.0017 (12) | 0.0034 (12) | 0.0064 (11) |
C13 | 0.0272 (15) | 0.0155 (13) | 0.0282 (14) | 0.0011 (12) | −0.0016 (12) | −0.0001 (11) |
C14 | 0.0256 (15) | 0.0170 (13) | 0.0246 (13) | 0.0068 (12) | 0.0008 (11) | −0.0045 (10) |
O1 | 0.0212 (10) | 0.0193 (10) | 0.0182 (9) | 0.0048 (8) | −0.0033 (7) | −0.0008 (7) |
O2 | 0.0263 (11) | 0.0176 (10) | 0.0225 (9) | 0.0052 (8) | −0.0042 (8) | −0.0041 (7) |
O3 | 0.0386 (12) | 0.0173 (10) | 0.0150 (9) | 0.0015 (9) | 0.0063 (8) | −0.0002 (7) |
O4 | 0.0375 (12) | 0.0139 (9) | 0.0206 (9) | 0.0014 (9) | 0.0042 (8) | 0.0013 (8) |
O5 | 0.0260 (10) | 0.0182 (10) | 0.0132 (8) | 0.0029 (8) | −0.0005 (7) | 0.0003 (7) |
C21 | 0.0152 (12) | 0.0197 (13) | 0.0165 (12) | 0.0000 (10) | −0.0002 (9) | 0.0019 (10) |
C22 | 0.0193 (12) | 0.0173 (13) | 0.0132 (11) | −0.0002 (10) | −0.0013 (9) | 0.0014 (9) |
C23 | 0.0166 (12) | 0.0131 (12) | 0.0175 (12) | −0.0006 (10) | 0.0042 (10) | −0.0008 (9) |
C24 | 0.0205 (13) | 0.0122 (12) | 0.0181 (12) | 0.0003 (10) | 0.0006 (10) | 0.0020 (9) |
C25 | 0.0159 (12) | 0.0166 (12) | 0.0130 (11) | −0.0015 (10) | 0.0022 (9) | 0.0021 (9) |
C26 | 0.0181 (12) | 0.0175 (12) | 0.0135 (11) | −0.0014 (10) | 0.0017 (9) | −0.0004 (9) |
C27 | 0.0163 (12) | 0.0205 (14) | 0.0138 (11) | 0.0006 (10) | 0.0021 (9) | 0.0012 (9) |
C28 | 0.0183 (13) | 0.0142 (12) | 0.0167 (11) | 0.0017 (10) | 0.0022 (9) | 0.0003 (9) |
O6 | 0.0209 (10) | 0.0246 (11) | 0.0175 (9) | 0.0040 (9) | −0.0023 (7) | 0.0010 (8) |
O7 | 0.0246 (11) | 0.0326 (12) | 0.0236 (11) | −0.0030 (10) | −0.0046 (9) | −0.0012 (9) |
O8 | 0.0346 (12) | 0.0190 (11) | 0.0296 (11) | −0.0034 (10) | −0.0081 (9) | 0.0044 (9) |
O9 | 0.0323 (12) | 0.0202 (10) | 0.0229 (10) | −0.0020 (9) | −0.0007 (9) | 0.0037 (8) |
O10 | 0.0296 (11) | 0.0222 (10) | 0.0214 (10) | −0.0020 (9) | −0.0011 (8) | 0.0043 (8) |
Ni1—N11 | 2.054 (2) | C12—C13 | 1.519 (4) |
Ni1—N1 | 2.077 (2) | C12—H12A | 0.9900 |
Ni1—N8 | 2.079 (2) | C12—H12B | 0.9900 |
Ni1—O1 | 2.081 (2) | C13—C14 | 1.527 (4) |
Ni1—N4 | 2.089 (2) | C13—H13A | 0.9900 |
Ni1—O6 | 2.183 (2) | C13—H13B | 0.9900 |
N1—C2 | 1.470 (4) | C14—H14A | 0.9900 |
N1—C14 | 1.479 (4) | C14—H14B | 0.9900 |
N1—H1 | 0.9300 | O1—C27 | 1.261 (3) |
C2—C3 | 1.521 (5) | O2—C27 | 1.258 (3) |
C2—H2A | 0.9900 | O3—C28 | 1.264 (3) |
C2—H2B | 0.9900 | O4—C28 | 1.252 (3) |
C3—N4 | 1.481 (4) | O5—C25 | 1.378 (3) |
C3—H3A | 0.9900 | O5—H5 | 0.8400 |
C3—H3B | 0.9900 | C21—C22 | 1.390 (4) |
N4—C5 | 1.482 (4) | C21—C26 | 1.396 (3) |
N4—H4 | 0.9300 | C21—C27 | 1.509 (4) |
C5—C6 | 1.520 (4) | C22—C23 | 1.399 (4) |
C5—H5A | 0.9900 | C22—H22 | 0.9500 |
C5—H5B | 0.9900 | C23—C24 | 1.396 (3) |
C6—C7 | 1.523 (5) | C23—C28 | 1.507 (4) |
C6—H6C | 0.9900 | C24—C25 | 1.390 (4) |
C6—H6D | 0.9900 | C24—H24 | 0.9500 |
C7—N8 | 1.477 (4) | C25—C26 | 1.392 (4) |
C7—H7C | 0.9900 | C26—H26 | 0.9500 |
C7—H7D | 0.9900 | O6—H6A | 0.90 (3) |
N8—C9 | 1.481 (4) | O6—H6B | 0.90 (3) |
N8—H8 | 0.9300 | O7—H7A | 0.86 (3) |
C9—C10 | 1.524 (4) | O7—H7B | 0.89 (3) |
C9—H9C | 0.9900 | O8—H8A | 0.88 (3) |
C9—H9D | 0.9900 | O8—H8B | 0.87 (3) |
C10—N11 | 1.477 (4) | O9—H9A | 0.85 (3) |
C10—H10C | 0.9900 | O9—H9B | 0.88 (3) |
C10—H10D | 0.9900 | O10—H10A | 0.92 (3) |
N11—C12 | 1.480 (4) | O10—H10B | 0.87 (3) |
N11—H11 | 0.9300 | ||
N11—Ni1—N1 | 93.70 (9) | N8—C9—H9D | 109.7 |
N11—Ni1—N8 | 86.6 (2) | C10—C9—H9D | 109.7 |
N1—Ni1—N8 | 178.5 (2) | H9C—C9—H9D | 108.2 |
N11—Ni1—O1 | 90.42 (9) | N11—C10—C9 | 108.4 (2) |
N1—Ni1—O1 | 94.76 (8) | N11—C10—H10C | 110.0 |
N8—Ni1—O1 | 86.77 (8) | C9—C10—H10C | 110.0 |
N11—Ni1—N4 | 178.34 (9) | N11—C10—H10D | 110.0 |
N1—Ni1—N4 | 84.80 (9) | C9—C10—H10D | 110.0 |
N8—Ni1—N4 | 94.97 (9) | H10C—C10—H10D | 108.4 |
O1—Ni1—N4 | 89.01 (9) | C10—N11—C12 | 112.9 (2) |
N11—Ni1—O6 | 89.69 (8) | C10—N11—Ni1 | 106.0 (2) |
N1—Ni1—O6 | 91.22 (8) | C12—N11—Ni1 | 117.3 (2) |
N8—Ni1—O6 | 87.25 (8) | C10—N11—H11 | 106.7 |
O1—Ni1—O6 | 174.00 (8) | C12—N11—H11 | 106.7 |
N4—Ni1—O6 | 91.04 (8) | Ni1—N11—H11 | 106.7 |
C2—N1—C14 | 115.0 (2) | N11—C12—C13 | 112.0 (2) |
C2—N1—Ni1 | 107.1 (2) | N11—C12—H12A | 109.2 |
C14—N1—Ni1 | 115.6 (2) | C13—C12—H12A | 109.2 |
C2—N1—H1 | 106.1 | N11—C12—H12B | 109.2 |
C14—N1—H1 | 106.1 | C13—C12—H12B | 109.2 |
Ni1—N1—H1 | 106.1 | H12A—C12—H12B | 107.9 |
N1—C2—C3 | 108.3 (2) | C12—C13—C14 | 115.3 (2) |
N1—C2—H2A | 110.0 | C12—C13—H13A | 108.4 |
C3—C2—H2A | 110.0 | C14—C13—H13A | 108.4 |
N1—C2—H2B | 110.0 | C12—C13—H13B | 108.4 |
C3—C2—H2B | 110.0 | C14—C13—H13B | 108.4 |
H2A—C2—H2B | 108.4 | H13A—C13—H13B | 107.5 |
N4—C3—C2 | 108.6 (2) | N1—C14—C13 | 111.6 (2) |
N4—C3—H3A | 110.0 | N1—C14—H14A | 109.3 |
C2—C3—H3A | 110.0 | C13—C14—H14A | 109.3 |
N4—C3—H3B | 110.0 | N1—C14—H14B | 109.3 |
C2—C3—H3B | 110.0 | C13—C14—H14B | 109.3 |
H3A—C3—H3B | 108.3 | H14A—C14—H14B | 108.0 |
C3—N4—C5 | 113.4 (2) | C27—O1—Ni1 | 132.6 (2) |
C3—N4—Ni1 | 104.5 (2) | C25—O5—H5 | 109.5 |
C5—N4—Ni1 | 114.9 (2) | C22—C21—C26 | 119.9 (2) |
C3—N4—H4 | 107.9 | C22—C21—C27 | 120.4 (2) |
C5—N4—H4 | 107.9 | C26—C21—C27 | 119.6 (2) |
Ni1—N4—H4 | 107.9 | C21—C22—C23 | 120.4 (2) |
N4—C5—C6 | 112.4 (2) | C21—C22—H22 | 119.8 |
N4—C5—H5A | 109.1 | C23—C22—H22 | 119.8 |
C6—C5—H5A | 109.1 | C24—C23—C22 | 119.6 (2) |
N4—C5—H5B | 109.1 | C24—C23—C28 | 120.1 (2) |
C6—C5—H5B | 109.1 | C22—C23—C28 | 120.3 (2) |
H5A—C5—H5B | 107.9 | C25—C24—C23 | 119.9 (2) |
C5—C6—C7 | 115.4 (3) | C25—C24—H24 | 120.1 |
C5—C6—H6C | 108.4 | C23—C24—H24 | 120.1 |
C7—C6—H6C | 108.4 | O5—C25—C24 | 118.1 (2) |
C5—C6—H6D | 108.4 | O5—C25—C26 | 121.2 (2) |
C7—C6—H6D | 108.4 | C24—C25—C26 | 120.6 (2) |
H6C—C6—H6D | 107.5 | C25—C26—C21 | 119.6 (2) |
N8—C7—C6 | 112.2 (2) | C25—C26—H26 | 120.2 |
N8—C7—H7C | 109.2 | C21—C26—H26 | 120.2 |
C6—C7—H7C | 109.2 | O2—C27—O1 | 125.7 (2) |
N8—C7—H7D | 109.2 | O2—C27—C21 | 118.7 (2) |
C6—C7—H7D | 109.2 | O1—C27—C21 | 115.6 (2) |
H7C—C7—H7D | 107.9 | O4—C28—O3 | 122.9 (2) |
C7—N8—C9 | 113.4 (2) | O4—C28—C23 | 118.9 (2) |
C7—N8—Ni1 | 115.5 (2) | O3—C28—C23 | 118.2 (2) |
C9—N8—Ni1 | 103.5 (2) | Ni1—O6—H6A | 120 (3) |
C7—N8—H8 | 108.0 | Ni1—O6—H6B | 124 (2) |
C9—N8—H8 | 108.0 | H6A—O6—H6B | 103 (4) |
Ni1—N8—H8 | 108.0 | H7A—O7—H7B | 115 (4) |
N8—C9—C10 | 109.6 (2) | H8A—O8—H8B | 103 (4) |
N8—C9—H9C | 109.7 | H9A—O9—H9B | 113 (4) |
C10—C9—H9C | 109.7 | H10A—O10—H10B | 99 (5) |
N11—Ni1—N1—C2 | −169.5 (2) | N1—Ni1—N11—C10 | 165.8 (2) |
O1—Ni1—N1—C2 | 99.8 (2) | N8—Ni1—N11—C10 | −12.7 (2) |
N4—Ni1—N1—C2 | 11.2 (2) | O1—Ni1—N11—C10 | −99.4 (2) |
O6—Ni1—N1—C2 | −79.7 (12) | O6—Ni1—N11—C10 | 74.6 (2) |
N11—Ni1—N1—C14 | −39.9 (2) | N1—Ni1—N11—C12 | 38.7 (2) |
O1—Ni1—N1—C14 | −130.6 (2) | N8—Ni1—N11—C12 | −139.8 (2) |
N4—Ni1—N1—C14 | 140.8 (2) | O1—Ni1—N11—C12 | 133.5 (2) |
O6—Ni1—N1—C14 | 49.9 (2) | O6—Ni1—N11—C12 | −52.5 (2) |
C14—N1—C2—C3 | −168.8 (2) | C10—N11—C12—C13 | −179.0 (2) |
Ni1—N1—C2—C3 | −38.9 (2) | Ni1—N11—C12—C13 | −55.3 (3) |
N1—C2—C3—N4 | 58.3 (3) | N11—C12—C13—C14 | 69.5 (3) |
C2—C3—N4—C5 | −171.2 (2) | C2—N1—C14—C13 | −176.3 (2) |
C2—C3—N4—Ni1 | −45.3 (2) | Ni1—N1—C14—C13 | 58.0 (3) |
N1—Ni1—N4—C3 | 18.8 (2) | C12—C13—C14—N1 | −71.6 (3) |
N8—Ni1—N4—C3 | −162.7 (2) | N11—Ni1—O1—C27 | −82.8 (3) |
O1—Ni1—N4—C3 | −76.1 (2) | N1—Ni1—O1—C27 | 10.9 (3) |
O6—Ni1—N4—C3 | 110.0 (2) | N8—Ni1—O1—C27 | −169.4 (3) |
N1—Ni1—N4—C5 | 143.8 (2) | N4—Ni1—O1—C27 | 95.6 (3) |
N8—Ni1—N4—C5 | −37.8 (2) | C26—C21—C22—C23 | −2.0 (4) |
O1—Ni1—N4—C5 | 48.9 (2) | C27—C21—C22—C23 | 178.1 (2) |
O6—Ni1—N4—C5 | −125.1 (2) | C21—C22—C23—C24 | 0.6 (4) |
C3—N4—C5—C6 | 176.1 (2) | C21—C22—C23—C28 | 178.9 (2) |
Ni1—N4—C5—C6 | 56.0 (3) | C22—C23—C24—C25 | 1.0 (4) |
N4—C5—C6—C7 | −72.3 (3) | C28—C23—C24—C25 | −177.3 (3) |
C5—C6—C7—N8 | 72.0 (3) | C23—C24—C25—O5 | 177.2 (2) |
C6—C7—N8—C9 | −175.1 (2) | C23—C24—C25—C26 | −1.2 (4) |
C6—C7—N8—Ni1 | −55.9 (3) | O5—C25—C26—C21 | −178.6 (2) |
N11—Ni1—N8—C7 | −141.4 (2) | C24—C25—C26—C21 | −0.2 (4) |
O1—Ni1—N8—C7 | −50.8 (2) | C22—C21—C26—C25 | 1.8 (4) |
N4—Ni1—N8—C7 | 37.9 (2) | C27—C21—C26—C25 | −178.3 (2) |
O6—Ni1—N8—C7 | 128.7 (2) | Ni1—O1—C27—O2 | 6.7 (4) |
N11—Ni1—N8—C9 | −16.9 (2) | Ni1—O1—C27—C21 | −171.4 (2) |
O1—Ni1—N8—C9 | 73.7 (2) | C22—C21—C27—O2 | 164.3 (3) |
N4—Ni1—N8—C9 | 162.5 (2) | C26—C21—C27—O2 | −15.6 (4) |
O6—Ni1—N8—C9 | −106.8 (2) | C22—C21—C27—O1 | −17.5 (4) |
C7—N8—C9—C10 | 169.3 (2) | C26—C21—C27—O1 | 162.7 (2) |
Ni1—N8—C9—C10 | 43.5 (2) | C24—C23—C28—O4 | −31.6 (4) |
N8—C9—C10—N11 | −58.1 (3) | C22—C23—C28—O4 | 150.1 (3) |
C9—C10—N11—C12 | 169.3 (2) | C24—C23—C28—O3 | 148.3 (3) |
C9—C10—N11—Ni1 | 39.5 (3) | C22—C23—C28—O3 | −30.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.93 | 2.06 | 2.903 (3) | 150 |
N4—H4···O3i | 0.93 | 2.49 | 3.344 (3) | 153 |
N8—H8···O7 | 0.93 | 2.13 | 3.032 (3) | 164 |
N11—H11···O9ii | 0.93 | 2.20 | 3.018 (3) | 147 |
O5—H5···O3iii | 0.84 | 1.69 | 2.519 (3) | 169 |
O6—H6A···O7 | 0.90 (3) | 1.80 (3) | 2.670 (3) | 161 (4) |
O6—H6B···O5iv | 0.90 (3) | 2.00 (3) | 2.864 (3) | 160 (4) |
O7—H7A···O8 | 0.86 (3) | 1.88 (3) | 2.719 (3) | 164 (4) |
O7—H7B···O10iii | 0.89 (3) | 1.91 (3) | 2.793 (3) | 172 (4) |
O8—H8A···O9 | 0.88 (3) | 1.84 (3) | 2.712 (3) | 169 (4) |
O8—H8B···O5v | 0.87 (3) | 1.97 (3) | 2.824 (3) | 167 (5) |
O9—H9A···O10 | 0.85 (3) | 1.97 (3) | 2.824 (3) | 176 (4) |
O9—H9B···O4vi | 0.88 (3) | 1.93 (3) | 2.801 (3) | 174 (4) |
O10—H10A···O2vii | 0.92 (3) | 1.83 (3) | 2.739 (3) | 169 (3) |
O10—H10B···O4v | 0.87 (3) | 1.85 (3) | 2.718 (3) | 174 (8) |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x−1/2, −y+1/2, z−1/2; (iii) x, −y+1, z−1/2; (iv) x+1/2, −y+1/2, z+1/2; (v) x+1/2, y−1/2, z+1; (vi) x+1/2, −y+3/2, z+1/2; (vii) x+1/2, y+1/2, z+1. |
C18H28N4NiO4·H2O | F(000) = 936 |
Mr = 441.17 | Dx = 1.441 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.2155 (4) Å | Cell parameters from 2402 reflections |
b = 16.0404 (6) Å | θ = 2.6–27.5° |
c = 8.8937 (3) Å | µ = 0.99 mm−1 |
β = 118.4900 (16)° | T = 150 K |
V = 2033.14 (11) Å3 | Block, purple |
Z = 4 | 0.18 × 0.16 × 0.16 mm |
Kappa-CCD diffractometer | 2333 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1622 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.088 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→20 |
Tmin = 0.842, Tmax = 0.858 | k = 0→20 |
12978 measured reflections | l = −11→10 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.147 | w = 1/[σ2(Fo2) + (0.0754P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2333 reflections | Δρmax = 0.83 e Å−3 |
134 parameters | Δρmin = −0.85 e Å−3 |
1 restraint | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0193 (17) |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.2500 | 0.2500 | 0.0000 | 0.0247 (2) | |
N1 | 0.17290 (19) | 0.34829 (15) | 0.0202 (3) | 0.0269 (6) | |
C2 | 0.2208 (2) | 0.3725 (2) | 0.2020 (4) | 0.0333 (8) | |
C3 | 0.2515 (2) | 0.2942 (2) | 0.3125 (4) | 0.0326 (8) | |
N4 | 0.31102 (19) | 0.24304 (15) | 0.2643 (3) | 0.0267 (6) | |
C5 | 0.3266 (2) | 0.1572 (2) | 0.3344 (4) | 0.0334 (8) | |
C6 | 0.3900 (2) | 0.1077 (2) | 0.2841 (4) | 0.0350 (8) | |
C7 | 0.3461 (2) | 0.08048 (19) | 0.0968 (4) | 0.0333 (8) | |
O1 | 0.14783 (15) | 0.16226 (13) | −0.0325 (3) | 0.0301 (5) | |
O2 | 0.03070 (16) | 0.22725 (14) | −0.0099 (3) | 0.0338 (6) | |
C11 | 0.0346 (2) | 0.07824 (19) | −0.0107 (4) | 0.0270 (7) | |
C12 | 0.0720 (2) | 0.0063 (2) | −0.0410 (4) | 0.0304 (7) | |
C13 | −0.0374 (2) | 0.07130 (19) | 0.0316 (4) | 0.0288 (7) | |
C14 | 0.0733 (2) | 0.16271 (19) | −0.0194 (4) | 0.0268 (7) | |
O3 | 0.0000 | 0.3041 (3) | 0.2500 | 0.0708 (14) | |
H1 | 0.1149 | 0.3266 | −0.0026 | 0.032* | |
H2A | 0.1778 | 0.4056 | 0.2284 | 0.040* | |
H2B | 0.2763 | 0.4073 | 0.2266 | 0.040* | |
H3A | 0.2871 | 0.3098 | 0.4348 | 0.039* | |
H3B | 0.1957 | 0.2618 | 0.2953 | 0.039* | |
H4 | 0.3693 | 0.2689 | 0.3091 | 0.032* | |
H5A | 0.2655 | 0.1284 | 0.2910 | 0.040* | |
H5B | 0.3557 | 0.1598 | 0.4607 | 0.040* | |
H6A | 0.4117 | 0.0573 | 0.3568 | 0.042* | |
H6B | 0.4461 | 0.1419 | 0.3104 | 0.042* | |
H7A | 0.3891 | 0.0412 | 0.0830 | 0.040* | |
H7B | 0.2866 | 0.0507 | 0.0656 | 0.040* | |
H12 | 0.1218 | 0.0104 | −0.0684 | 0.037* | |
H13 | −0.0629 | 0.1201 | 0.0541 | 0.035* | |
H3 | 0.008 (6) | 0.266 (3) | 0.190 (8) | 0.11 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0270 (4) | 0.0229 (3) | 0.0269 (3) | −0.0040 (2) | 0.0151 (3) | 0.0000 (2) |
N1 | 0.0280 (14) | 0.0243 (14) | 0.0320 (14) | −0.0029 (11) | 0.0172 (12) | 0.0008 (11) |
C2 | 0.0375 (18) | 0.0323 (18) | 0.0349 (18) | −0.0015 (15) | 0.0211 (15) | −0.0062 (14) |
C3 | 0.0362 (19) | 0.036 (2) | 0.0298 (17) | −0.0042 (15) | 0.0192 (15) | −0.0021 (14) |
N4 | 0.0276 (14) | 0.0258 (14) | 0.0274 (13) | −0.0035 (11) | 0.0137 (11) | 0.0009 (11) |
C5 | 0.0346 (18) | 0.0344 (19) | 0.0300 (17) | −0.0040 (15) | 0.0145 (15) | 0.0068 (14) |
C6 | 0.0358 (19) | 0.0306 (18) | 0.0353 (18) | 0.0008 (15) | 0.0143 (15) | 0.0076 (14) |
C7 | 0.0320 (17) | 0.0245 (16) | 0.0445 (19) | −0.0025 (14) | 0.0192 (16) | 0.0020 (14) |
O1 | 0.0306 (12) | 0.0257 (12) | 0.0394 (12) | −0.0067 (10) | 0.0210 (10) | −0.0021 (10) |
O2 | 0.0329 (13) | 0.0280 (12) | 0.0438 (14) | −0.0021 (10) | 0.0211 (11) | 0.0024 (10) |
C11 | 0.0264 (16) | 0.0257 (16) | 0.0277 (16) | −0.0025 (13) | 0.0119 (13) | 0.0049 (13) |
C12 | 0.0258 (16) | 0.0329 (19) | 0.0352 (18) | −0.0029 (13) | 0.0166 (14) | 0.0023 (14) |
C13 | 0.0291 (17) | 0.0241 (16) | 0.0355 (17) | −0.0034 (13) | 0.0173 (14) | 0.0020 (13) |
C14 | 0.0267 (17) | 0.0262 (17) | 0.0268 (16) | −0.0044 (13) | 0.0121 (13) | 0.0027 (13) |
O3 | 0.101 (4) | 0.065 (3) | 0.053 (3) | 0.000 | 0.042 (3) | 0.000 |
Ni1—N1i | 2.072 (3) | C5—H5A | 0.99 |
Ni1—N1 | 2.072 (3) | C5—H5B | 0.99 |
Ni1—N4 | 2.073 (3) | C6—C7 | 1.530 (4) |
Ni1—N4i | 2.073 (3) | C6—H6A | 0.99 |
Ni1—O1 | 2.086 (2) | C6—H6B | 0.99 |
Ni1—O1i | 2.086 (2) | C7—N1i | 1.476 (4) |
N1—C2 | 1.473 (4) | C7—H7A | 0.99 |
N1—C7i | 1.476 (4) | C7—H7B | 0.99 |
N1—H1 | 0.93 | O1—C14 | 1.269 (3) |
C2—C3 | 1.524 (4) | O2—C14 | 1.269 (4) |
C2—H2A | 0.99 | C11—C12 | 1.388 (4) |
C2—H2B | 0.99 | C11—C13 | 1.392 (4) |
C3—N4 | 1.477 (4) | C11—C14 | 1.510 (4) |
C3—H3A | 0.99 | C12—C13ii | 1.385 (4) |
C3—H3B | 0.99 | C12—H12 | 0.95 |
N4—C5 | 1.482 (4) | C13—C12ii | 1.385 (4) |
N4—H4 | 0.93 | C13—H13 | 0.95 |
C5—C6 | 1.525 (5) | O3—H3 | 0.86 (7) |
N1i—Ni1—N1 | 180 | C5—N4—Ni1 | 114.9 (2) |
N1i—Ni1—N4 | 94.4 (2) | C3—N4—H4 | 107.4 |
N1—Ni1—N4 | 85.7 (2) | C5—N4—H4 | 107.4 |
N1i—Ni1—N4i | 85.7 (2) | Ni1—N4—H4 | 107.4 |
N1—Ni1—N4i | 94.4 (2) | N4—C5—C6 | 111.4 (3) |
N4—Ni1—N4i | 180 | N4—C5—H5A | 109.4 |
N1i—Ni1—O1 | 87.0 (2) | C6—C5—H5A | 109.4 |
N1—Ni1—O1 | 93.1 (2) | N4—C5—H5B | 109.4 |
N4—Ni1—O1 | 92.22 (9) | C6—C5—H5B | 109.4 |
N4i—Ni1—O1 | 87.78 (9) | H5A—C5—H5B | 108.0 |
N1i—Ni1—O1i | 93.1 (2) | C5—C6—C7 | 116.1 (3) |
N1—Ni1—O1i | 87.0 (2) | C5—C6—H6A | 108.3 |
N4—Ni1—O1i | 87.78 (9) | C7—C6—H6A | 108.3 |
N4i—Ni1—O1i | 92.22 (9) | C5—C6—H6B | 108.3 |
O1—Ni1—O1i | 180 | C7—C6—H6B | 108.3 |
C2—N1—C7i | 113.2 (2) | H6A—C6—H6B | 107.4 |
C2—N1—Ni1 | 105.7 (2) | N1i—C7—C6 | 112.3 (3) |
C7i—N1—Ni1 | 117.4 (2) | N1i—C7—H7A | 109.2 |
C2—N1—H1 | 106.6 | C6—C7—H7A | 109.2 |
C7i—N1—H1 | 106.6 | N1i—C7—H7B | 109.2 |
Ni1—N1—H1 | 106.6 | C6—C7—H7B | 109.2 |
N1—C2—C3 | 109.3 (3) | H7A—C7—H7B | 107.9 |
N1—C2—H2A | 109.8 | C14—O1—Ni1 | 135.4 (2) |
C3—C2—H2A | 109.8 | C12—C11—C13 | 119.1 (3) |
N1—C2—H2B | 109.8 | C12—C11—C14 | 120.4 (3) |
C3—C2—H2B | 109.8 | C13—C11—C14 | 120.5 (3) |
H2A—C2—H2B | 108.3 | C13ii—C12—C11 | 120.5 (3) |
N4—C3—C2 | 109.1 (2) | C13ii—C12—H12 | 119.7 |
N4—C3—H3A | 109.9 | C11—C12—H12 | 119.7 |
C2—C3—H3A | 109.9 | C12ii—C13—C11 | 120.3 (3) |
N4—C3—H3B | 109.9 | C12ii—C13—H13 | 119.8 |
C2—C3—H3B | 109.9 | C11—C13—H13 | 119.8 |
H3A—C3—H3B | 108.3 | O1—C14—O2 | 125.7 (3) |
C3—N4—C5 | 113.4 (2) | O1—C14—C11 | 115.9 (3) |
C3—N4—Ni1 | 105.9 (2) | O2—C14—C11 | 118.4 (3) |
N4—Ni1—N1—C2 | 15.2 (2) | O1i—Ni1—N4—C5 | −133.1 (2) |
N4i—Ni1—N1—C2 | −164.8 (2) | C3—N4—C5—C6 | −178.8 (2) |
O1—Ni1—N1—C2 | 107.2 (2) | Ni1—N4—C5—C6 | 59.1 (3) |
O1i—Ni1—N1—C2 | −72.8 (2) | N4—C5—C6—C7 | −72.6 (4) |
N4—Ni1—N1—C7i | 142.5 (2) | C5—C6—C7—N1i | 68.4 (4) |
N4i—Ni1—N1—C7i | −37.5 (2) | N1i—Ni1—O1—C14 | 170.1 (3) |
O1—Ni1—N1—C7i | −125.5 (2) | N1—Ni1—O1—C14 | −9.9 (3) |
O1i—Ni1—N1—C7i | 54.5 (2) | N4—Ni1—O1—C14 | 75.9 (3) |
C7i—N1—C2—C3 | −170.9 (3) | N4i—Ni1—O1—C14 | −104.1 (3) |
Ni1—N1—C2—C3 | −41.1 (3) | C13—C11—C12—C13ii | 0.9 (5) |
N1—C2—C3—N4 | 56.1 (3) | C14—C11—C12—C13ii | 179.4 (3) |
C2—C3—N4—C5 | −166.7 (3) | C12—C11—C13—C12ii | −0.9 (5) |
C2—C3—N4—Ni1 | −39.8 (3) | C14—C11—C13—C12ii | −179.4 (3) |
N1i—Ni1—N4—C3 | −166.2 (2) | Ni1—O1—C14—O2 | 14.0 (5) |
N1—Ni1—N4—C3 | 13.8 (2) | Ni1—O1—C14—C11 | −164.5 (2) |
O1—Ni1—N4—C3 | −79.1 (2) | C12—C11—C14—O1 | −9.0 (4) |
O1i—Ni1—N4—C3 | 100.9 (2) | C13—C11—C14—O1 | 169.5 (3) |
N1i—Ni1—N4—C5 | −40.2 (2) | C12—C11—C14—O2 | 172.3 (3) |
N1—Ni1—N4—C5 | 139.8 (2) | C13—C11—C14—O2 | −9.2 (4) |
O1—Ni1—N4—C5 | 46.9 (2) |
Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) −x, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.93 | 2.08 | 2.927 (4) | 151 |
N4—H4···O2iii | 0.93 | 2.33 | 3.182 (3) | 152 |
O3—H3···O2 | 0.86 (7) | 2.09 (4) | 2.865 (3) | 152 (5) |
Symmetry code: (iii) x+1/2, −y+1/2, z+1/2. |
2(C15H25N4NiO4)·C10H28N4NiO2·2(ClO4)·0.86(H2O) | F(000) = 1345 |
Mr = 1277.62 | Dx = 1.550 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8295 (3) Å | Cell parameters from 6029 reflections |
b = 16.9416 (5) Å | θ = 2.6–27.5° |
c = 14.9596 (5) Å | µ = 1.20 mm−1 |
β = 93.6260 (13)° | T = 150 K |
V = 2739.13 (14) Å3 | Plate, purple |
Z = 2 | 0.40 × 0.36 × 0.12 mm |
Kappa-CCD diffractometer | 6277 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 5362 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→14 |
Tmin = 0.646, Tmax = 0.869 | k = 0→21 |
20675 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0347P)2 + 1.8839P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
6277 reflections | Δρmax = 0.45 e Å−3 |
377 parameters | Δρmin = −0.62 e Å−3 |
12 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0031 (6) |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.02030 (10) | |
O1 | 0.38485 (14) | 0.60422 (9) | 0.51792 (10) | 0.0259 (3) | |
N1 | 0.39309 (15) | 0.43568 (10) | 0.58281 (11) | 0.0236 (3) | |
N4 | 0.37720 (15) | 0.46280 (10) | 0.39646 (11) | 0.0237 (3) | |
C2 | 0.27679 (19) | 0.41805 (12) | 0.52933 (14) | 0.0272 (4) | |
C3 | 0.30689 (19) | 0.39725 (12) | 0.43400 (14) | 0.0274 (4) | |
C5 | 0.4313 (2) | 0.44231 (13) | 0.31113 (14) | 0.0302 (5) | |
C6 | 0.5073 (2) | 0.50998 (14) | 0.27584 (14) | 0.0330 (5) | |
C7 | 0.6280 (2) | 0.52759 (14) | 0.32990 (14) | 0.0302 (5) | |
Ni2 | 0.05830 (2) | 0.726187 (13) | 0.219586 (15) | 0.01786 (9) | |
N21 | 0.24350 (16) | 0.74376 (10) | 0.25471 (11) | 0.0243 (3) | |
N24 | 0.11892 (16) | 0.65442 (9) | 0.11953 (10) | 0.0229 (3) | |
N28 | −0.12864 (16) | 0.70977 (10) | 0.18166 (11) | 0.0232 (3) | |
N211 | −0.00371 (16) | 0.79631 (9) | 0.32214 (10) | 0.0229 (3) | |
C22 | 0.3101 (2) | 0.71693 (13) | 0.17691 (15) | 0.0309 (5) | |
C23 | 0.2520 (2) | 0.64054 (13) | 0.14163 (14) | 0.0293 (4) | |
C25 | 0.0468 (2) | 0.58163 (12) | 0.10260 (14) | 0.0290 (4) | |
C26 | −0.0892 (2) | 0.59926 (13) | 0.07795 (14) | 0.0312 (5) | |
C27 | −0.1634 (2) | 0.62875 (13) | 0.15456 (14) | 0.0286 (4) | |
C29 | −0.1968 (2) | 0.73968 (14) | 0.25759 (14) | 0.0302 (4) | |
C210 | −0.1339 (2) | 0.81369 (12) | 0.29573 (14) | 0.0286 (4) | |
C212 | 0.0701 (2) | 0.86785 (12) | 0.34468 (13) | 0.0295 (5) | |
C213 | 0.2064 (2) | 0.84962 (13) | 0.36452 (14) | 0.0332 (5) | |
C214 | 0.2767 (2) | 0.82481 (13) | 0.28417 (14) | 0.0307 (5) | |
O31 | 0.22188 (12) | 0.61039 (8) | 0.37722 (9) | 0.0241 (3) | |
O32 | 0.03561 (12) | 0.63084 (8) | 0.30767 (8) | 0.0203 (3) | |
O33 | 0.05499 (14) | 0.67231 (8) | 0.64061 (8) | 0.0238 (3) | |
O34 | 0.06560 (15) | 0.71343 (8) | 0.49881 (9) | 0.0294 (3) | |
C31 | 0.04684 (16) | 0.55333 (10) | 0.43868 (11) | 0.0159 (3) | |
C32 | 0.03135 (16) | 0.57742 (10) | 0.52690 (11) | 0.0163 (3) | |
C33 | 0.01418 (16) | 0.47667 (10) | 0.41329 (11) | 0.0170 (3) | |
C37 | 0.10573 (17) | 0.60403 (10) | 0.37045 (11) | 0.0175 (3) | |
C38 | 0.05380 (17) | 0.66177 (10) | 0.55700 (11) | 0.0180 (4) | |
O2 | 0.6171 (6) | 1.0018 (3) | 0.5361 (5) | 0.080 (3) | 0.430 (9) |
Cl1 | 0.56740 (10) | 0.78843 (7) | 0.45060 (7) | 0.0347 (2) | 0.914 (4) |
O3 | 0.4901 (2) | 0.76585 (13) | 0.52103 (15) | 0.0531 (7) | 0.914 (4) |
O4 | 0.5410 (2) | 0.73697 (12) | 0.37519 (14) | 0.0498 (6) | 0.914 (4) |
O5 | 0.5434 (3) | 0.86856 (12) | 0.42446 (17) | 0.0570 (7) | 0.914 (4) |
O6 | 0.6948 (3) | 0.7793 (2) | 0.4816 (3) | 0.0500 (7) | 0.914 (4) |
Cl21 | 0.5838 (12) | 0.8020 (8) | 0.4670 (9) | 0.0347 (2) | 0.086 (4) |
O23 | 0.540 (2) | 0.8302 (13) | 0.5482 (13) | 0.052 (5)* | 0.086 (4) |
O24 | 0.502 (2) | 0.7348 (12) | 0.4352 (15) | 0.052 (5)* | 0.086 (4) |
O25 | 0.569 (3) | 0.8595 (15) | 0.3952 (15) | 0.052 (5)* | 0.086 (4) |
O26 | 0.708 (3) | 0.773 (2) | 0.477 (3) | 0.052 (5)* | 0.086 (4) |
H1A | 0.415 (3) | 0.6503 (16) | 0.5209 (19) | 0.050 (6)* | |
H1B | 0.328 (3) | 0.6076 (18) | 0.4750 (18) | 0.050 (6)* | |
H11 | 0.4333 | 0.3879 | 0.5944 | 0.028* | |
H4 | 0.3217 | 0.5039 | 0.3844 | 0.028* | |
H2A | 0.2214 | 0.4646 | 0.5286 | 0.033* | |
H2B | 0.2338 | 0.3733 | 0.5564 | 0.033* | |
H3A | 0.3565 | 0.3482 | 0.4342 | 0.033* | |
H3B | 0.2294 | 0.3883 | 0.3967 | 0.033* | |
H5A | 0.3640 | 0.4287 | 0.2659 | 0.036* | |
H5B | 0.4849 | 0.3953 | 0.3204 | 0.036* | |
H6A | 0.5265 | 0.4976 | 0.2136 | 0.040* | |
H6B | 0.4558 | 0.5583 | 0.2739 | 0.040* | |
H7A | 0.6748 | 0.4778 | 0.3401 | 0.036* | |
H7B | 0.6789 | 0.5635 | 0.2951 | 0.036* | |
H21 | 0.2651 | 0.7100 | 0.3021 | 0.029* | |
H24 | 0.1127 | 0.6837 | 0.0668 | 0.027* | |
H28 | −0.1479 | 0.7425 | 0.1329 | 0.028* | |
H211 | −0.0026 | 0.7652 | 0.3734 | 0.027* | |
H22A | 0.3985 | 0.7082 | 0.1951 | 0.037* | |
H22B | 0.3046 | 0.7577 | 0.1294 | 0.037* | |
H23A | 0.2926 | 0.6232 | 0.0875 | 0.035* | |
H23B | 0.2629 | 0.5986 | 0.1875 | 0.035* | |
H25A | 0.0534 | 0.5480 | 0.1569 | 0.035* | |
H25B | 0.0819 | 0.5519 | 0.0532 | 0.035* | |
H26A | −0.0940 | 0.6394 | 0.0298 | 0.037* | |
H26B | −0.1289 | 0.5506 | 0.0533 | 0.037* | |
H27A | −0.2527 | 0.6273 | 0.1357 | 0.034* | |
H27B | −0.1494 | 0.5930 | 0.2066 | 0.034* | |
H29A | −0.1983 | 0.6987 | 0.3047 | 0.036* | |
H29B | −0.2833 | 0.7519 | 0.2368 | 0.036* | |
H10A | −0.1386 | 0.8561 | 0.2502 | 0.034* | |
H10B | −0.1766 | 0.8321 | 0.3484 | 0.034* | |
H12A | 0.0372 | 0.8936 | 0.3976 | 0.035* | |
H12B | 0.0611 | 0.9054 | 0.2940 | 0.035* | |
H13A | 0.2136 | 0.8069 | 0.4097 | 0.040* | |
H13B | 0.2469 | 0.8970 | 0.3916 | 0.040* | |
H14A | 0.2578 | 0.8620 | 0.2341 | 0.037* | |
H14B | 0.3668 | 0.8274 | 0.3002 | 0.037* | |
H33 | 0.0233 | 0.4607 | 0.3532 | 0.020* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.01959 (18) | 0.02151 (18) | 0.01963 (17) | 0.00139 (13) | −0.00010 (13) | −0.00117 (13) |
O1 | 0.0260 (7) | 0.0237 (7) | 0.0277 (7) | 0.0037 (6) | −0.0020 (6) | −0.0016 (6) |
N1 | 0.0234 (8) | 0.0237 (8) | 0.0237 (8) | 0.0016 (6) | 0.0010 (6) | 0.0001 (7) |
N4 | 0.0235 (8) | 0.0243 (8) | 0.0231 (8) | 0.0019 (6) | −0.0010 (6) | −0.0020 (7) |
C2 | 0.0241 (10) | 0.0266 (10) | 0.0309 (10) | −0.0013 (8) | 0.0018 (8) | −0.0004 (8) |
C3 | 0.0243 (10) | 0.0262 (10) | 0.0312 (10) | −0.0007 (8) | −0.0016 (8) | −0.0017 (8) |
C5 | 0.0333 (11) | 0.0340 (12) | 0.0229 (10) | 0.0001 (9) | −0.0006 (8) | −0.0060 (9) |
C6 | 0.0377 (12) | 0.0393 (12) | 0.0221 (10) | −0.0013 (10) | 0.0023 (9) | 0.0010 (9) |
C7 | 0.0324 (11) | 0.0345 (11) | 0.0245 (10) | −0.0008 (9) | 0.0080 (8) | −0.0001 (9) |
Ni2 | 0.02472 (15) | 0.01504 (13) | 0.01393 (13) | 0.00146 (9) | 0.00205 (9) | 0.00220 (8) |
N21 | 0.0288 (9) | 0.0223 (8) | 0.0221 (8) | −0.0018 (7) | 0.0029 (7) | 0.0061 (7) |
N24 | 0.0338 (9) | 0.0179 (8) | 0.0173 (7) | 0.0045 (7) | 0.0046 (6) | 0.0026 (6) |
N28 | 0.0281 (9) | 0.0235 (8) | 0.0179 (7) | 0.0023 (7) | 0.0001 (6) | 0.0021 (6) |
N211 | 0.0338 (9) | 0.0192 (8) | 0.0158 (7) | 0.0022 (7) | 0.0032 (6) | 0.0015 (6) |
C22 | 0.0294 (11) | 0.0345 (12) | 0.0296 (11) | 0.0022 (9) | 0.0084 (9) | 0.0079 (9) |
C23 | 0.0334 (11) | 0.0285 (11) | 0.0269 (10) | 0.0093 (9) | 0.0085 (8) | 0.0044 (8) |
C25 | 0.0469 (13) | 0.0177 (9) | 0.0226 (9) | 0.0012 (9) | 0.0028 (9) | −0.0016 (8) |
C26 | 0.0438 (13) | 0.0265 (10) | 0.0224 (10) | −0.0043 (9) | −0.0041 (9) | −0.0048 (8) |
C27 | 0.0312 (11) | 0.0296 (11) | 0.0245 (10) | −0.0061 (8) | −0.0027 (8) | 0.0009 (8) |
C29 | 0.0277 (11) | 0.0365 (12) | 0.0270 (10) | 0.0052 (9) | 0.0060 (8) | 0.0011 (9) |
C210 | 0.0357 (11) | 0.0276 (10) | 0.0231 (9) | 0.0098 (9) | 0.0060 (8) | 0.0007 (8) |
C212 | 0.0494 (13) | 0.0185 (9) | 0.0207 (9) | −0.0004 (9) | 0.0026 (9) | −0.0016 (8) |
C213 | 0.0465 (13) | 0.0269 (11) | 0.0253 (10) | −0.0099 (9) | −0.0052 (9) | −0.0005 (9) |
C214 | 0.0346 (11) | 0.0262 (10) | 0.0307 (11) | −0.0091 (9) | −0.0022 (9) | 0.0050 (9) |
O31 | 0.0213 (7) | 0.0254 (7) | 0.0255 (7) | −0.0008 (5) | 0.0009 (5) | 0.0090 (6) |
O32 | 0.0264 (7) | 0.0186 (6) | 0.0156 (6) | −0.0007 (5) | −0.0010 (5) | 0.0054 (5) |
O33 | 0.0409 (8) | 0.0170 (6) | 0.0138 (6) | −0.0047 (6) | 0.0035 (5) | −0.0035 (5) |
O34 | 0.0554 (10) | 0.0157 (6) | 0.0169 (6) | −0.0056 (6) | 0.0015 (6) | 0.0006 (5) |
C31 | 0.0187 (8) | 0.0137 (8) | 0.0152 (8) | 0.0009 (6) | −0.0005 (6) | 0.0010 (6) |
C32 | 0.0189 (8) | 0.0151 (8) | 0.0148 (8) | −0.0003 (6) | −0.0003 (6) | −0.0003 (6) |
C33 | 0.0226 (9) | 0.0157 (8) | 0.0128 (7) | 0.0003 (7) | 0.0005 (6) | −0.0002 (6) |
C37 | 0.0259 (9) | 0.0129 (8) | 0.0138 (8) | 0.0003 (7) | 0.0014 (7) | −0.0012 (6) |
C38 | 0.0225 (9) | 0.0163 (8) | 0.0151 (8) | −0.0008 (7) | 0.0006 (7) | −0.0006 (7) |
O2 | 0.081 (4) | 0.051 (3) | 0.104 (5) | 0.005 (3) | −0.023 (3) | −0.027 (3) |
Cl1 | 0.0388 (4) | 0.0278 (5) | 0.0379 (5) | −0.0003 (3) | 0.0054 (3) | −0.0003 (3) |
O3 | 0.0557 (14) | 0.0475 (13) | 0.0596 (14) | −0.0008 (10) | 0.0309 (11) | −0.0035 (10) |
O4 | 0.0691 (15) | 0.0357 (11) | 0.0438 (12) | 0.0074 (10) | −0.0038 (10) | −0.0073 (9) |
O5 | 0.086 (2) | 0.0241 (10) | 0.0598 (16) | 0.0048 (10) | −0.0016 (13) | 0.0006 (10) |
O6 | 0.0388 (13) | 0.0518 (15) | 0.0589 (15) | −0.0083 (10) | −0.0002 (11) | 0.0090 (11) |
Cl21 | 0.0388 (4) | 0.0278 (5) | 0.0379 (5) | −0.0003 (3) | 0.0054 (3) | −0.0003 (3) |
Ni1—N1i | 2.060 (2) | C22—C23 | 1.519 (3) |
Ni1—N1 | 2.060 (2) | C22—H22A | 0.99 |
Ni1—N4 | 2.075 (2) | C22—H22B | 0.99 |
Ni1—N4i | 2.075 (2) | C23—H23A | 0.99 |
Ni1—O1i | 2.188 (2) | C23—H23B | 0.99 |
Ni1—O1 | 2.188 (2) | C25—C26 | 1.525 (3) |
O1—H1A | 0.85 (3) | C25—H25A | 0.99 |
O1—H1B | 0.86 (3) | C25—H25B | 0.99 |
N1—C7i | 1.477 (3) | C26—C27 | 1.525 (3) |
N1—C2 | 1.479 (3) | C26—H26A | 0.99 |
N1—H11 | 0.93 | C26—H26B | 0.99 |
N4—C3 | 1.477 (3) | C27—H27A | 0.99 |
N4—C5 | 1.479 (3) | C27—H27B | 0.99 |
N4—H4 | 0.93 | C29—C210 | 1.521 (3) |
C2—C3 | 1.524 (3) | C29—H29A | 0.99 |
C2—H2A | 0.99 | C29—H29B | 0.99 |
C2—H2B | 0.99 | C210—H10A | 0.99 |
C3—H3A | 0.99 | C210—H10B | 0.99 |
C3—H3B | 0.99 | C212—C213 | 1.519 (3) |
C5—C6 | 1.525 (3) | C212—H12A | 0.99 |
C5—H5A | 0.99 | C212—H12B | 0.99 |
C5—H5B | 0.99 | C213—C214 | 1.523 (3) |
C6—C7 | 1.523 (3) | C213—H13A | 0.99 |
C6—H6A | 0.99 | C213—H13B | 0.99 |
C6—H6B | 0.99 | C214—H14A | 0.99 |
C7—N1i | 1.477 (3) | C214—H14B | 0.99 |
C7—H7A | 0.99 | O31—C37 | 1.260 (2) |
C7—H7B | 0.99 | O32—C37 | 1.255 (2) |
Ni2—N21 | 2.063 (2) | O33—C38 | 1.263 (2) |
Ni2—N24 | 2.067 (2) | O33—Ni2iii | 2.086 (2) |
Ni2—N211 | 2.085 (2) | O34—C38 | 1.247 (2) |
Ni2—O33ii | 2.085 (2) | C31—C33 | 1.393 (2) |
Ni2—N28 | 2.086 (2) | C31—C32 | 1.401 (2) |
Ni2—O32 | 2.109 (2) | C31—C37 | 1.506 (2) |
N21—C22 | 1.479 (3) | C32—C33iv | 1.393 (2) |
N21—C214 | 1.480 (3) | C32—C38 | 1.513 (2) |
N21—H21 | 0.93 | C33—C32iv | 1.393 (2) |
N24—C25 | 1.473 (3) | C33—H33 | 0.95 |
N24—C23 | 1.477 (3) | Cl1—O5 | 1.432 (2) |
N24—H24 | 0.93 | Cl1—O6 | 1.436 (3) |
N28—C27 | 1.474 (3) | Cl1—O3 | 1.438 (2) |
N28—C29 | 1.482 (3) | Cl1—O4 | 1.440 (2) |
N28—H28 | 0.93 | Cl21—O23 | 1.42 (2) |
N211—C210 | 1.469 (3) | Cl21—O26 | 1.43 (2) |
N211—C212 | 1.479 (3) | Cl21—O25 | 1.45 (2) |
N211—H211 | 0.93 | Cl21—O24 | 1.50 (2) |
N1i—Ni1—N1 | 180 | C210—N211—Ni2 | 105.3 (2) |
N1i—Ni1—N4 | 94.00 (6) | C212—N211—Ni2 | 116.1 (2) |
N1—Ni1—N4 | 86.00 (6) | C210—N211—H211 | 107.3 |
N1i—Ni1—N4i | 85.99 (6) | C212—N211—H211 | 107.3 |
N1—Ni1—N4i | 94.01 (6) | Ni2—N211—H211 | 107.3 |
N4—Ni1—N4i | 180 | N21—C22—C23 | 108.9 (2) |
N1i—Ni1—O1i | 90.39 (6) | N21—C22—H22A | 109.9 |
N1—Ni1—O1i | 89.60 (6) | C23—C22—H22A | 109.9 |
N4—Ni1—O1i | 90.39 (6) | N21—C22—H22B | 109.9 |
N4i—Ni1—O1i | 89.61 (6) | C23—C22—H22B | 109.9 |
N1i—Ni1—O1 | 89.61 (6) | H22A—C22—H22B | 108.3 |
N1—Ni1—O1 | 90.40 (6) | N24—C23—C22 | 108.6 (2) |
N4—Ni1—O1 | 89.61 (6) | N24—C23—H23A | 110.0 |
N4i—Ni1—O1 | 90.39 (6) | C22—C23—H23A | 110.0 |
O1i—Ni1—O1 | 180 | N24—C23—H23B | 110.0 |
Ni1—O1—H1A | 122 (2) | C22—C23—H23B | 110.0 |
Ni1—O1—H1B | 110 (2) | H23A—C23—H23B | 108.4 |
H1A—O1—H1B | 103 (3) | N24—C25—C26 | 111.8 (2) |
C7i—N1—C2 | 112.9 (2) | N24—C25—H25A | 109.3 |
C7i—N1—Ni1 | 115.7 (2) | C26—C25—H25A | 109.3 |
C2—N1—Ni1 | 105.9 (2) | N24—C25—H25B | 109.3 |
C7i—N1—H11 | 107.3 | C26—C25—H25B | 109.3 |
C2—N1—H11 | 107.3 | H25A—C25—H25B | 107.9 |
Ni1—N1—H11 | 107.3 | C27—C26—C25 | 115.4 (2) |
C3—N4—C5 | 113.2 (2) | C27—C26—H26A | 108.4 |
C3—N4—Ni1 | 105.4 (2) | C25—C26—H26A | 108.4 |
C5—N4—Ni1 | 116.4 (2) | C27—C26—H26B | 108.4 |
C3—N4—H4 | 107.1 | C25—C26—H26B | 108.4 |
C5—N4—H4 | 107.1 | H26A—C26—H26B | 107.5 |
Ni1—N4—H4 | 107.1 | N28—C27—C26 | 112.0 (2) |
N1—C2—C3 | 109.12 (16) | N28—C27—H27A | 109.2 |
N1—C2—H2A | 109.9 | C26—C27—H27A | 109.2 |
C3—C2—H2A | 109.9 | N28—C27—H27B | 109.2 |
N1—C2—H2B | 109.9 | C26—C27—H27B | 109.2 |
C3—C2—H2B | 109.9 | H27A—C27—H27B | 107.9 |
H2A—C2—H2B | 108.3 | N28—C29—C210 | 109.7 (2) |
N4—C3—C2 | 109.1 (2) | N28—C29—H29A | 109.7 |
N4—C3—H3A | 109.9 | C210—C29—H29A | 109.7 |
C2—C3—H3A | 109.9 | N28—C29—H29B | 109.7 |
N4—C3—H3B | 109.9 | C210—C29—H29B | 109.7 |
C2—C3—H3B | 109.9 | H29A—C29—H29B | 108.2 |
H3A—C3—H3B | 108.3 | N211—C210—C29 | 109.6 (2) |
N4—C5—C6 | 112.0 (2) | N211—C210—H10A | 109.8 |
N4—C5—H5A | 109.2 | C29—C210—H10A | 109.8 |
C6—C5—H5A | 109.2 | N211—C210—H10B | 109.8 |
N4—C5—H5B | 109.2 | C29—C210—H10B | 109.8 |
C6—C5—H5B | 109.2 | H10A—C210—H10B | 108.2 |
H5A—C5—H5B | 107.9 | N211—C212—C213 | 112.5 (2) |
C7—C6—C5 | 115.3 (2) | N211—C212—H12A | 109.1 |
C7—C6—H6A | 108.4 | C213—C212—H12A | 109.1 |
C5—C6—H6A | 108.4 | N211—C212—H12B | 109.1 |
C7—C6—H6B | 108.4 | C213—C212—H12B | 109.1 |
C5—C6—H6B | 108.4 | H12A—C212—H12B | 107.8 |
H6A—C6—H6B | 107.5 | C212—C213—C214 | 115.5 (2) |
N1i—C7—C6 | 112.1 (2) | C212—C213—H13A | 108.4 |
N1i—C7—H7A | 109.2 | C214—C213—H13A | 108.4 |
C6—C7—H7A | 109.2 | C212—C213—H13B | 108.4 |
N1i—C7—H7B | 109.2 | C214—C213—H13B | 108.4 |
C6—C7—H7B | 109.2 | H13A—C213—H13B | 107.5 |
H7A—C7—H7B | 107.9 | N21—C214—C213 | 111.5 (2) |
N21—Ni2—N24 | 85.48 (7) | N21—C214—H14A | 109.3 |
N21—Ni2—N211 | 94.80 (7) | C213—C214—H14A | 109.3 |
N24—Ni2—N211 | 178.71 (6) | N21—C214—H14B | 109.3 |
N21—Ni2—O33ii | 90.39 (6) | C213—C214—H14B | 109.3 |
N24—Ni2—O33ii | 93.99 (6) | H14A—C214—H14B | 108.0 |
N211—Ni2—O33ii | 87.26 (6) | C37—O32—Ni2 | 131.0 (2) |
N21—Ni2—N28 | 178.82 (6) | C38—O33—Ni2iii | 132.6 (2) |
N24—Ni2—N28 | 94.12 (7) | C33—C31—C32 | 119.0 (2) |
N211—Ni2—N28 | 85.63 (7) | C33—C31—C37 | 117.3 (2) |
O33ii—Ni2—N28 | 88.53 (6) | C32—C31—C37 | 123.6 (2) |
N21—Ni2—O32 | 95.81 (6) | C33iv—C32—C31 | 118.8 (2) |
N24—Ni2—O32 | 93.26 (6) | C33iv—C32—C38 | 119.1 (2) |
N211—Ni2—O32 | 85.47 (6) | C31—C32—C38 | 121.9 (2) |
O33ii—Ni2—O32 | 170.81 (5) | C31—C33—C32iv | 122.2 (2) |
N28—Ni2—O32 | 85.32 (6) | C31—C33—H33 | 118.9 |
C22—N21—C214 | 113.5 (2) | C32iv—C33—H33 | 118.9 |
C22—N21—Ni2 | 105.7 (2) | O32—C37—O31 | 125.7 (2) |
C214—N21—Ni2 | 115.1 (2) | O32—C37—C31 | 116.8 (2) |
C22—N21—H21 | 107.4 | O31—C37—C31 | 117.2 (2) |
C214—N21—H21 | 107.4 | O34—C38—O33 | 126.7 (2) |
Ni2—N21—H21 | 107.4 | O34—C38—C32 | 118.5 (2) |
C25—N24—C23 | 113.9 (2) | O33—C38—C32 | 114.8 (2) |
C25—N24—Ni2 | 115.3 (2) | O5—Cl1—O6 | 110.1 (2) |
C23—N24—Ni2 | 106.4 (2) | O5—Cl1—O3 | 110.4 (2) |
C25—N24—H24 | 106.9 | O6—Cl1—O3 | 109.1 (2) |
C23—N24—H24 | 106.9 | O5—Cl1—O4 | 109.7 (2) |
Ni2—N24—H24 | 106.9 | O6—Cl1—O4 | 109.1 (2) |
C27—N28—C29 | 113.5 (2) | O3—Cl1—O4 | 108.5 (2) |
C27—N28—Ni2 | 115.2 (2) | O23—Cl21—O26 | 113 (2) |
C29—N28—Ni2 | 105.5 (2) | O23—Cl21—O25 | 113 (2) |
C27—N28—H28 | 107.4 | O26—Cl21—O25 | 111 (2) |
C29—N28—H28 | 107.4 | O23—Cl21—O24 | 108 (2) |
Ni2—N28—H28 | 107.4 | O26—Cl21—O24 | 108 (2) |
C210—N211—C212 | 113.1 (2) | O25—Cl21—O24 | 104 (2) |
N4—Ni1—N1—C7i | −140.2 (2) | N28—Ni2—N211—C210 | −16.1 (2) |
N4i—Ni1—N1—C7i | 39.9 (2) | O32—Ni2—N211—C210 | −101.7 (2) |
O1i—Ni1—N1—C7i | 129.4 (2) | N21—Ni2—N211—C212 | 36.9 (2) |
O1—Ni1—N1—C7i | −50.6 (2) | O33ii—Ni2—N211—C212 | −53.3 (2) |
N4—Ni1—N1—C2 | −14.3 (2) | N28—Ni2—N211—C212 | −142.0 (2) |
N4i—Ni1—N1—C2 | 165.7 (2) | O32—Ni2—N211—C212 | 132.3 (2) |
O1i—Ni1—N1—C2 | −104.8 (2) | C214—N21—C22—C23 | −169.4 (2) |
O1—Ni1—N1—C2 | 75.2 (2) | Ni2—N21—C22—C23 | −42.4 (2) |
N1i—Ni1—N4—C3 | 165.4 (2) | C25—N24—C23—C22 | −167.9 (2) |
N1—Ni1—N4—C3 | −14.6 (2) | Ni2—N24—C23—C22 | −39.8 (2) |
O1i—Ni1—N4—C3 | 74.9 (2) | N21—C22—C23—N24 | 56.6 (2) |
O1—Ni1—N4—C3 | −105.1 (2) | C23—N24—C25—C26 | −178.6 (2) |
N1i—Ni1—N4—C5 | 39.0 (2) | Ni2—N24—C25—C26 | 58.0 (2) |
N1—Ni1—N4—C5 | −141.0 (2) | N24—C25—C26—C27 | −71.7 (2) |
O1i—Ni1—N4—C5 | −51.4 (2) | C29—N28—C27—C26 | −178.6 (2) |
O1—Ni1—N4—C5 | 128.6 (2) | Ni2—N28—C27—C26 | −56.8 (2) |
C7i—N1—C2—C3 | 1678.0 (2) | C25—C26—C27—N28 | 71.1 (2) |
Ni1—N1—C2—C3 | 40.5 (2) | C27—N28—C29—C210 | 166.0 (2) |
C5—N4—C3—C2 | 169.0 (2) | Ni2—N28—C29—C210 | 38.9 (2) |
Ni1—N4—C3—C2 | 40.642) | C212—N211—C210—C29 | 169.7 (2) |
N1—C2—C3—N4 | −56.3 (2) | Ni2—N211—C210—C29 | 41.8 (2) |
C3—N4—C5—C6 | −177.89 (2) | N28—C29—C210—N211 | −56.4 (2) |
Ni1—N4—C5—C6 | −55.4 (2) | C210—N211—C212—C213 | −175.4 (2) |
N4—C5—C6—C7 | 69.7 (2) | Ni2—N211—C212—C213 | −53.4 (2) |
C5—C6—C7—N1i | −71.4 (2) | N211—C212—C213—C214 | 70.3 (2) |
N24—Ni2—N21—C22 | 16.1 (2) | C22—N21—C214—C213 | −179.8 (2) |
N211—Ni2—N21—C22 | −165.1 (2) | Ni2—N21—C214—C213 | 58.4 (2) |
O33ii—Ni2—N21—C22 | −77.9 (2) | C212—C213—C214—N21 | −73.2 (2) |
O32—Ni2—N21—C22 | 108.9 (2) | N21—Ni2—O32—C37 | 10.84 (16) |
N24—Ni2—N21—C214 | 142.1 (2) | N24—Ni2—O32—C37 | 96.62 (16) |
N211—Ni2—N21—C214 | −39.2 (2) | N211—Ni2—O32—C37 | −83.5 (2) |
O33ii—Ni2—N21—C214 | 48.1 (2) | N28—Ni2—O32—C37 | −169.5 (2) |
O32—Ni2—N21—C214 | −125.1 (2) | C33—C31—C32—C33iv | 1.1 (3) |
N21—Ni2—N24—C25 | 140.5 (2) | C37—C31—C32—C33iv | −174.3 (2) |
O33ii—Ni2—N24—C25 | −129.5 (2) | C33—C31—C32—C38 | −174.4 (2) |
N28—Ni2—N24—C25 | −40.7 (2) | C37—C31—C32—C38 | 10.2 (3) |
O32—Ni2—N24—C25 | 44.9 (2) | C32—C31—C33—C32iv | −1.2 (3) |
N21—Ni2—N24—C23 | 13.2 (2) | C37—C31—C33—C32iv | 174.6 (2) |
O33ii—Ni2—N24—C23 | 103.3 (2) | Ni2—O32—C37—O31 | −25.6 (3) |
N28—Ni2—N24—C23 | −167.9 (2) | Ni2—O32—C37—C31 | 160.6 (2) |
O32—Ni2—N24—C23 | −82.4 (2) | C33—C31—C37—O32 | 75.1 (2) |
N24—Ni2—N28—C27 | 40.1 (2) | C32—C31—C37—O32 | −109.4 (2) |
N211—Ni2—N28—C27 | −138.6 (2) | C33—C31—C37—O31 | −99.3 (2) |
O33ii—Ni2—N28—C27 | 134.0 (2) | C32—C31—C37—O31 | 76.3 (2) |
O32—Ni2—N28—C27 | −52.8 (2) | Ni2iii—O33—C38—O34 | 7.0 (3) |
N24—Ni2—N28—C29 | 166.1 (2) | Ni2iii—O33—C38—C32 | −170.9 (2) |
N211—Ni2—N28—C29 | −12.7 (2) | C33iv—C32—C38—O34 | −163.1 (2) |
O33ii—Ni2—N28—C29 | −100.0 (2) | C31—C32—C38—O34 | 12.4 (3) |
O32—Ni2—N28—C29 | 73.2 (2) | C33iv—C32—C38—O33 | 15.0 (2) |
N21—Ni2—N211—C210 | 162.9 (2) | C31—C32—C38—O33 | −169.6 (2) |
O33ii—Ni2—N211—C210 | 72.7 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2; (iv) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O3 | 0.85 (3) | 2.12 (3) | 2.965 (3) | 177 (3) |
O1—H1A···O24 | 0.85 (3) | 2.17 (4) | 2.87 (2) | 139 (3) |
O1—H1B···O31 | 0.86 (3) | 1.80 (3) | 2.662 (2) | 173 (3) |
N1—H11···O4i | 0.93 | 2.18 | 3.066 (3) | 159 |
N1—H11···O24i | 0.93 | 2.25 | 3.12 (2) | 156 |
N4—H4···O31 | 0.93 | 2.10 | 3.017 (2) | 167 |
N21—H21···O31 | 0.93 | 2.10 | 2.928 (2) | 148 |
N24—H24···O34ii | 0.93 | 2.07 | 2.911 (2) | 150 |
N211—H211···O34 | 0.93 | 2.16 | 3.045 (2) | 159 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2. |