Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615003952/ky3074sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615003952/ky3074Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229615003952/ky3074Isup3.pdf |
CCDC reference: 970136
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: publCIF (Westrip, 2010).
[Ni(C2H3O2)(C12H12N2)2]ClO4·H2O | Z = 2 |
Mr = 603.69 | F(000) = 628 |
Triclinic, P1 | Dx = 1.507 Mg m−3 |
a = 10.8804 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.4335 (3) Å | Cell parameters from 16444 reflections |
c = 12.5387 (3) Å | θ = 4.2–30.7° |
α = 66.319 (2)° | µ = 0.88 mm−1 |
β = 78.224 (2)° | T = 110 K |
γ = 69.035 (2)° | Plate, violet |
V = 1330.59 (7) Å3 | 0.20 × 0.14 × 0.07 mm |
Agilent Xcalibur Sapphire3 diffractometer | 6083 independent reflections |
Radiation source: sealed X-ray tube | 5416 reflections with I > 2σ(I) |
Detector resolution: 16.0655 pixels mm-1 | Rint = 0.035 |
ω scans | θmax = 27.5°, θmin = 4.2° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | h = −14→14 |
Tmin = 0.855, Tmax = 1.000 | k = −14→14 |
31626 measured reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0376P)2 + 1.5035P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
6083 reflections | Δρmax = 0.72 e Å−3 |
370 parameters | Δρmin = −0.45 e Å−3 |
12 restraints |
Experimental. Elemental analysis was performed on CHNOS Elemental Analyzer vario MICRO instrument. Infrared spectra were recorded on a Perkin Elmer Spectrum 100 FT–IR Spectrophotometer with UATR accessory in the range of 4000–400 cm-1. IR (in cm-1): 3554 (s h), 3483 (m), 3427 (m), 3115 (w), 3064 (w), 3047 (s h), 3028 (w), 2980 (w), 2960 (w), 2928 (w), 2872 (w), 2847 (w), 2748 (w), 2794 (w), 1641 (w), 1608 (m), 1601 (s h), 1587 (m), 1576 (m), 1537 (s), 1502 (m), 1481 (s), 1454 (s), 1421 (s h), 1394 (m), 1346 (s h), 1317 (m), 1294 (w), 1250 (w), 1234 (m), 1167 (w), 1149 (m), 1109 (vs), 1098 (s h), 1084 (vs), 1049 (s), 999 (m), 974 (w), 937 (w), 849 (s), 833 (s), 818 (w), 762 (w), 731 (m), 694 (w), 677 (m), 652 (m), 620 (s), 553 (w), 540 (w), 496 (w), 484 (s h), 422 (m). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ni1 | 0.74173 (2) | 0.00664 (2) | 0.73994 (2) | 0.01468 (8) | |
Cl1 | 0.77635 (5) | 0.49449 (5) | 0.76694 (4) | 0.02327 (12) | |
O1 | 0.65942 (14) | 0.02326 (15) | 0.59259 (12) | 0.0201 (3) | |
O2 | 0.55764 (14) | 0.15889 (15) | 0.68879 (13) | 0.0221 (3) | |
O3 | 0.76577 (19) | 0.50234 (18) | 0.88070 (14) | 0.0355 (4) | |
O4 | 0.68946 (19) | 0.42413 (19) | 0.76736 (17) | 0.0392 (4) | |
O5 | 0.73810 (17) | 0.62781 (16) | 0.68170 (14) | 0.0306 (4) | |
O6 | 0.90982 (17) | 0.42330 (19) | 0.73845 (15) | 0.0359 (4) | |
O7A | 0.4688 (4) | 0.4515 (5) | 0.6443 (5) | 0.0750 (11) | 0.670 (5) |
H1W | 0.529 (3) | 0.4774 (18) | 0.659 (4) | 0.113* | |
H2W | 0.510 (4) | 0.3641 (12) | 0.668 (6) | 0.113* | 0.670 (5) |
O7B | 0.4626 (9) | 0.5364 (10) | 0.6152 (10) | 0.0750 (11) | 0.330 (5) |
H3W | 0.507 (7) | 0.545 (12) | 0.546 (2) | 0.113* | 0.330 (5) |
N1 | 0.85437 (17) | 0.12639 (17) | 0.63477 (14) | 0.0168 (3) | |
N2 | 0.92407 (16) | −0.13710 (17) | 0.73759 (14) | 0.0162 (3) | |
N3 | 0.75971 (16) | 0.02205 (16) | 0.89466 (14) | 0.0162 (3) | |
N4 | 0.64260 (16) | −0.12145 (17) | 0.85625 (14) | 0.0166 (3) | |
C1 | 0.9822 (2) | 0.0611 (2) | 0.61426 (17) | 0.0177 (4) | |
C2 | 1.0686 (2) | 0.1309 (2) | 0.54360 (18) | 0.0222 (4) | |
H2 | 1.1585 | 0.0840 | 0.5300 | 0.027* | |
C3 | 1.0219 (2) | 0.2696 (2) | 0.49320 (18) | 0.0241 (4) | |
H3 | 1.0802 | 0.3184 | 0.4452 | 0.029* | |
C4 | 0.8900 (2) | 0.3377 (2) | 0.51278 (18) | 0.0222 (4) | |
C5 | 0.8108 (2) | 0.2602 (2) | 0.58515 (17) | 0.0207 (4) | |
H5 | 0.7205 | 0.3048 | 0.6002 | 0.025* | |
C6 | 0.8331 (3) | 0.4873 (2) | 0.4580 (2) | 0.0294 (5) | |
H6A | 0.8079 | 0.5267 | 0.5188 | 0.044* | |
H6B | 0.7550 | 0.5090 | 0.4178 | 0.044* | |
H6C | 0.8991 | 0.5239 | 0.4017 | 0.044* | |
C7 | 1.02135 (19) | −0.0865 (2) | 0.67171 (16) | 0.0168 (4) | |
C8 | 1.1489 (2) | −0.1704 (2) | 0.66115 (18) | 0.0216 (4) | |
H8 | 1.2157 | −0.1342 | 0.6128 | 0.026* | |
C9 | 1.1772 (2) | −0.3071 (2) | 0.72177 (19) | 0.0229 (4) | |
H9 | 1.2640 | −0.3650 | 0.7151 | 0.027* | |
C10 | 1.0794 (2) | −0.3602 (2) | 0.79243 (18) | 0.0219 (4) | |
C11 | 0.9534 (2) | −0.2700 (2) | 0.79509 (17) | 0.0185 (4) | |
H11 | 0.8843 | −0.3047 | 0.8402 | 0.022* | |
C12 | 1.1083 (2) | −0.5075 (2) | 0.8643 (2) | 0.0299 (5) | |
H12A | 1.1657 | −0.5600 | 0.8175 | 0.045* | |
H12B | 1.0255 | −0.5299 | 0.8889 | 0.045* | |
H12C | 1.1526 | −0.5286 | 0.9334 | 0.045* | |
C13 | 0.70751 (19) | −0.0578 (2) | 0.99095 (17) | 0.0171 (4) | |
C14 | 0.7201 (2) | −0.0656 (2) | 1.10211 (18) | 0.0226 (4) | |
H14 | 0.6832 | −0.1225 | 1.1692 | 0.027* | |
C15 | 0.7874 (2) | 0.0109 (2) | 1.11331 (18) | 0.0232 (4) | |
H15 | 0.7978 | 0.0055 | 1.1887 | 0.028* | |
C16 | 0.8397 (2) | 0.0957 (2) | 1.01468 (18) | 0.0191 (4) | |
C17 | 0.82251 (19) | 0.0968 (2) | 0.90710 (17) | 0.0176 (4) | |
H17 | 0.8574 | 0.1539 | 0.8386 | 0.021* | |
C18 | 0.9108 (2) | 0.1835 (2) | 1.02124 (19) | 0.0229 (4) | |
H18A | 0.8465 | 0.2680 | 1.0244 | 0.034* | |
H18B | 0.9721 | 0.2024 | 0.9520 | 0.034* | |
H18C | 0.9601 | 0.1374 | 1.0916 | 0.034* | |
C19 | 0.63658 (19) | −0.13402 (19) | 0.96885 (17) | 0.0172 (4) | |
C20 | 0.5661 (2) | −0.2118 (2) | 1.05512 (18) | 0.0212 (4) | |
H20 | 0.5623 | −0.2199 | 1.1341 | 0.025* | |
C21 | 0.5013 (2) | −0.2776 (2) | 1.02487 (19) | 0.0232 (4) | |
H21 | 0.4531 | −0.3315 | 1.0833 | 0.028* | |
C22 | 0.5069 (2) | −0.2646 (2) | 0.90901 (19) | 0.0213 (4) | |
C23 | 0.57996 (19) | −0.1856 (2) | 0.82881 (19) | 0.0203 (4) | |
H23 | 0.5858 | −0.1765 | 0.7494 | 0.024* | |
C24 | 0.4363 (2) | −0.3307 (2) | 0.8704 (2) | 0.0282 (5) | |
H24A | 0.3629 | −0.2622 | 0.8245 | 0.042* | |
H24B | 0.4022 | −0.3937 | 0.9390 | 0.042* | |
H24C | 0.4979 | −0.3795 | 0.8223 | 0.042* | |
C25 | 0.5617 (2) | 0.1188 (2) | 0.60673 (18) | 0.0217 (4) | |
C26 | 0.4511 (3) | 0.1848 (3) | 0.5268 (3) | 0.0453 (7) | |
H26A | 0.4684 | 0.2620 | 0.4615 | 0.068* | |
H26B | 0.3679 | 0.2152 | 0.5701 | 0.068* | |
H26C | 0.4449 | 0.1203 | 0.4967 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.01446 (13) | 0.01728 (13) | 0.01351 (13) | −0.00572 (10) | 0.00119 (9) | −0.00706 (10) |
Cl1 | 0.0257 (3) | 0.0222 (2) | 0.0203 (2) | −0.0080 (2) | 0.00409 (19) | −0.00808 (19) |
O1 | 0.0197 (7) | 0.0241 (7) | 0.0181 (7) | −0.0062 (6) | −0.0011 (5) | −0.0097 (6) |
O2 | 0.0194 (7) | 0.0261 (8) | 0.0213 (7) | −0.0040 (6) | −0.0003 (6) | −0.0123 (6) |
O3 | 0.0440 (10) | 0.0332 (9) | 0.0217 (8) | −0.0017 (8) | −0.0011 (7) | −0.0119 (7) |
O4 | 0.0421 (11) | 0.0382 (10) | 0.0480 (11) | −0.0267 (9) | 0.0166 (8) | −0.0230 (9) |
O5 | 0.0352 (9) | 0.0258 (8) | 0.0244 (8) | −0.0097 (7) | 0.0003 (7) | −0.0037 (7) |
O6 | 0.0278 (9) | 0.0414 (10) | 0.0313 (9) | −0.0017 (8) | 0.0034 (7) | −0.0164 (8) |
O7A | 0.0502 (19) | 0.052 (2) | 0.114 (3) | −0.005 (2) | −0.020 (2) | −0.023 (3) |
O7B | 0.0502 (19) | 0.052 (2) | 0.114 (3) | −0.005 (2) | −0.020 (2) | −0.023 (3) |
N1 | 0.0191 (8) | 0.0200 (8) | 0.0139 (8) | −0.0081 (7) | 0.0009 (6) | −0.0077 (6) |
N2 | 0.0164 (8) | 0.0209 (8) | 0.0140 (7) | −0.0061 (7) | −0.0003 (6) | −0.0090 (6) |
N3 | 0.0155 (8) | 0.0173 (8) | 0.0149 (8) | −0.0035 (6) | 0.0002 (6) | −0.0071 (6) |
N4 | 0.0148 (8) | 0.0178 (8) | 0.0177 (8) | −0.0055 (6) | 0.0013 (6) | −0.0077 (6) |
C1 | 0.0185 (9) | 0.0248 (10) | 0.0140 (9) | −0.0093 (8) | 0.0012 (7) | −0.0101 (8) |
C2 | 0.0202 (10) | 0.0319 (11) | 0.0212 (10) | −0.0140 (9) | 0.0033 (8) | −0.0133 (9) |
C3 | 0.0302 (11) | 0.0311 (12) | 0.0196 (10) | −0.0202 (10) | 0.0047 (8) | −0.0112 (9) |
C4 | 0.0334 (12) | 0.0231 (10) | 0.0160 (9) | −0.0150 (9) | 0.0006 (8) | −0.0085 (8) |
C5 | 0.0263 (11) | 0.0199 (10) | 0.0179 (9) | −0.0093 (8) | 0.0036 (8) | −0.0093 (8) |
C6 | 0.0421 (14) | 0.0236 (11) | 0.0250 (11) | −0.0159 (10) | 0.0017 (10) | −0.0082 (9) |
C7 | 0.0163 (9) | 0.0243 (10) | 0.0139 (9) | −0.0070 (8) | −0.0002 (7) | −0.0107 (8) |
C8 | 0.0162 (10) | 0.0320 (11) | 0.0216 (10) | −0.0077 (8) | 0.0014 (8) | −0.0156 (9) |
C9 | 0.0164 (10) | 0.0288 (11) | 0.0254 (11) | −0.0004 (8) | −0.0040 (8) | −0.0163 (9) |
C10 | 0.0237 (10) | 0.0238 (10) | 0.0198 (10) | −0.0019 (8) | −0.0066 (8) | −0.0118 (8) |
C11 | 0.0205 (10) | 0.0208 (10) | 0.0152 (9) | −0.0057 (8) | −0.0010 (7) | −0.0083 (8) |
C12 | 0.0324 (12) | 0.0227 (11) | 0.0282 (12) | 0.0012 (9) | −0.0061 (9) | −0.0095 (9) |
C13 | 0.0162 (9) | 0.0164 (9) | 0.0164 (9) | −0.0025 (7) | −0.0007 (7) | −0.0061 (7) |
C14 | 0.0273 (11) | 0.0231 (10) | 0.0153 (9) | −0.0073 (9) | −0.0004 (8) | −0.0059 (8) |
C15 | 0.0268 (11) | 0.0248 (11) | 0.0166 (9) | −0.0022 (9) | −0.0042 (8) | −0.0097 (8) |
C16 | 0.0164 (9) | 0.0196 (10) | 0.0217 (10) | 0.0002 (8) | −0.0043 (7) | −0.0113 (8) |
C17 | 0.0160 (9) | 0.0194 (9) | 0.0183 (9) | −0.0044 (8) | −0.0001 (7) | −0.0091 (8) |
C18 | 0.0228 (10) | 0.0251 (11) | 0.0254 (11) | −0.0044 (9) | −0.0052 (8) | −0.0146 (9) |
C19 | 0.0147 (9) | 0.0156 (9) | 0.0181 (9) | −0.0018 (7) | 0.0002 (7) | −0.0060 (7) |
C20 | 0.0210 (10) | 0.0183 (10) | 0.0189 (10) | −0.0039 (8) | 0.0019 (8) | −0.0045 (8) |
C21 | 0.0195 (10) | 0.0181 (10) | 0.0266 (11) | −0.0064 (8) | 0.0043 (8) | −0.0050 (8) |
C22 | 0.0147 (9) | 0.0184 (10) | 0.0306 (11) | −0.0044 (8) | 0.0010 (8) | −0.0104 (8) |
C23 | 0.0152 (9) | 0.0223 (10) | 0.0279 (11) | −0.0068 (8) | 0.0035 (8) | −0.0150 (9) |
C24 | 0.0227 (11) | 0.0275 (12) | 0.0397 (13) | −0.0126 (9) | 0.0026 (9) | −0.0155 (10) |
C25 | 0.0211 (10) | 0.0234 (10) | 0.0208 (10) | −0.0060 (8) | −0.0027 (8) | −0.0083 (8) |
C26 | 0.0394 (15) | 0.0483 (16) | 0.0450 (16) | 0.0106 (13) | −0.0238 (12) | −0.0248 (13) |
Ni1—N1 | 2.0510 (17) | C8—C9 | 1.382 (3) |
Ni1—N4 | 2.0511 (17) | C8—H8 | 0.9500 |
Ni1—N3 | 2.0706 (16) | C9—C10 | 1.390 (3) |
Ni1—N2 | 2.0784 (17) | C9—H9 | 0.9500 |
Ni1—O1 | 2.1268 (14) | C10—C11 | 1.393 (3) |
Ni1—O2 | 2.1414 (15) | C10—C12 | 1.505 (3) |
Cl1—O5 | 1.4346 (16) | C11—H11 | 0.9500 |
Cl1—O6 | 1.4405 (17) | C12—H12A | 0.9800 |
Cl1—O4 | 1.4422 (18) | C12—H12B | 0.9800 |
Cl1—O3 | 1.4437 (17) | C12—H12C | 0.9800 |
O1—C25 | 1.266 (3) | C13—C14 | 1.393 (3) |
O2—C25 | 1.271 (3) | C13—C19 | 1.481 (3) |
O7A—O7B | 0.871 (9) | C14—C15 | 1.385 (3) |
O7A—H1W | 0.885 (8) | C14—H14 | 0.9500 |
O7A—H2W | 0.886 (8) | C15—C16 | 1.392 (3) |
O7B—H1W | 0.891 (10) | C15—H15 | 0.9500 |
O7B—H3W | 0.886 (8) | C16—C17 | 1.394 (3) |
N1—C5 | 1.337 (3) | C16—C18 | 1.504 (3) |
N1—C1 | 1.350 (3) | C17—H17 | 0.9500 |
N2—C11 | 1.341 (3) | C18—H18A | 0.9800 |
N2—C7 | 1.355 (3) | C18—H18B | 0.9800 |
N3—C17 | 1.338 (3) | C18—H18C | 0.9800 |
N3—C13 | 1.349 (3) | C19—C20 | 1.387 (3) |
N4—C23 | 1.333 (3) | C20—C21 | 1.388 (3) |
N4—C19 | 1.351 (3) | C20—H20 | 0.9500 |
C1—C2 | 1.390 (3) | C21—C22 | 1.390 (3) |
C1—C7 | 1.478 (3) | C21—H21 | 0.9500 |
C2—C3 | 1.387 (3) | C22—C23 | 1.385 (3) |
C2—H2 | 0.9500 | C22—C24 | 1.502 (3) |
C3—C4 | 1.391 (3) | C23—H23 | 0.9500 |
C3—H3 | 0.9500 | C24—H24A | 0.9800 |
C4—C5 | 1.390 (3) | C24—H24B | 0.9800 |
C4—C6 | 1.501 (3) | C24—H24C | 0.9800 |
C5—H5 | 0.9500 | C25—C26 | 1.502 (3) |
C6—H6A | 0.9800 | C26—H26A | 0.9800 |
C6—H6B | 0.9800 | C26—H26B | 0.9800 |
C6—H6C | 0.9800 | C26—H26C | 0.9800 |
C7—C8 | 1.392 (3) | ||
N1—Ni1—N4 | 174.56 (7) | C8—C9—C10 | 120.37 (19) |
N1—Ni1—N3 | 96.73 (6) | C8—C9—H9 | 119.8 |
N4—Ni1—N3 | 79.38 (7) | C10—C9—H9 | 119.8 |
N1—Ni1—N2 | 79.39 (7) | C9—C10—C11 | 116.8 (2) |
N4—Ni1—N2 | 97.14 (7) | C9—C10—C12 | 121.8 (2) |
N3—Ni1—N2 | 95.96 (6) | C11—C10—C12 | 121.5 (2) |
N1—Ni1—O1 | 91.24 (6) | N2—C11—C10 | 123.76 (19) |
N4—Ni1—O1 | 93.59 (6) | N2—C11—H11 | 118.1 |
N3—Ni1—O1 | 161.67 (6) | C10—C11—H11 | 118.1 |
N2—Ni1—O1 | 101.73 (6) | C10—C12—H12A | 109.5 |
N1—Ni1—O2 | 94.43 (6) | C10—C12—H12B | 109.5 |
N4—Ni1—O2 | 90.06 (6) | H12A—C12—H12B | 109.5 |
N3—Ni1—O2 | 100.94 (6) | C10—C12—H12C | 109.5 |
N2—Ni1—O2 | 162.60 (6) | H12A—C12—H12C | 109.5 |
O1—Ni1—O2 | 61.87 (5) | H12B—C12—H12C | 109.5 |
O5—Cl1—O6 | 109.97 (11) | N3—C13—C14 | 121.31 (19) |
O5—Cl1—O4 | 109.19 (12) | N3—C13—C19 | 115.18 (17) |
O6—Cl1—O4 | 109.06 (11) | C14—C13—C19 | 123.52 (18) |
O5—Cl1—O3 | 109.09 (10) | C15—C14—C13 | 119.02 (19) |
O6—Cl1—O3 | 110.19 (11) | C15—C14—H14 | 120.5 |
O4—Cl1—O3 | 109.33 (11) | C13—C14—H14 | 120.5 |
C25—O1—Ni1 | 89.58 (12) | C14—C15—C16 | 120.34 (19) |
C25—O2—Ni1 | 88.80 (12) | C14—C15—H15 | 119.8 |
H1W—O7A—H2W | 98.5 (17) | C16—C15—H15 | 119.8 |
H1W—O7A—H3W | 69 (5) | C15—C16—C17 | 116.69 (19) |
H2W—O7A—H3W | 124 (6) | C15—C16—C18 | 122.73 (18) |
H1W—O7B—H3W | 97.8 (18) | C17—C16—C18 | 120.57 (19) |
C5—N1—C1 | 119.03 (18) | N3—C17—C16 | 123.81 (19) |
C5—N1—Ni1 | 125.46 (14) | N3—C17—H17 | 118.1 |
C1—N1—Ni1 | 115.50 (13) | C16—C17—H17 | 118.1 |
C11—N2—C7 | 118.74 (17) | C16—C18—H18A | 109.5 |
C11—N2—Ni1 | 126.94 (14) | C16—C18—H18B | 109.5 |
C7—N2—Ni1 | 114.31 (13) | H18A—C18—H18B | 109.5 |
C17—N3—C13 | 118.81 (17) | C16—C18—H18C | 109.5 |
C17—N3—Ni1 | 126.39 (13) | H18A—C18—H18C | 109.5 |
C13—N3—Ni1 | 114.70 (13) | H18B—C18—H18C | 109.5 |
C23—N4—C19 | 118.94 (17) | N4—C19—C20 | 120.95 (19) |
C23—N4—Ni1 | 125.64 (14) | N4—C19—C13 | 115.20 (17) |
C19—N4—Ni1 | 115.33 (13) | C20—C19—C13 | 123.84 (18) |
N1—C1—C2 | 121.08 (19) | C19—C20—C21 | 119.31 (19) |
N1—C1—C7 | 115.29 (17) | C19—C20—H20 | 120.3 |
C2—C1—C7 | 123.63 (19) | C21—C20—H20 | 120.3 |
C3—C2—C1 | 119.2 (2) | C20—C21—C22 | 119.93 (19) |
C3—C2—H2 | 120.4 | C20—C21—H21 | 120.0 |
C1—C2—H2 | 120.4 | C22—C21—H21 | 120.0 |
C2—C3—C4 | 120.20 (19) | C23—C22—C21 | 116.87 (19) |
C2—C3—H3 | 119.9 | C23—C22—C24 | 120.7 (2) |
C4—C3—H3 | 119.9 | C21—C22—C24 | 122.5 (2) |
C5—C4—C3 | 116.8 (2) | N4—C23—C22 | 124.0 (2) |
C5—C4—C6 | 120.6 (2) | N4—C23—H23 | 118.0 |
C3—C4—C6 | 122.6 (2) | C22—C23—H23 | 118.0 |
N1—C5—C4 | 123.7 (2) | C22—C24—H24A | 109.5 |
N1—C5—H5 | 118.2 | C22—C24—H24B | 109.5 |
C4—C5—H5 | 118.2 | H24A—C24—H24B | 109.5 |
C4—C6—H6A | 109.5 | C22—C24—H24C | 109.5 |
C4—C6—H6B | 109.5 | H24A—C24—H24C | 109.5 |
H6A—C6—H6B | 109.5 | H24B—C24—H24C | 109.5 |
C4—C6—H6C | 109.5 | O1—C25—O2 | 119.72 (19) |
H6A—C6—H6C | 109.5 | O1—C25—C26 | 120.2 (2) |
H6B—C6—H6C | 109.5 | O2—C25—C26 | 120.1 (2) |
N2—C7—C8 | 121.00 (19) | C25—C26—H26A | 109.5 |
N2—C7—C1 | 115.49 (17) | C25—C26—H26B | 109.5 |
C8—C7—C1 | 123.51 (18) | H26A—C26—H26B | 109.5 |
C9—C8—C7 | 119.3 (2) | C25—C26—H26C | 109.5 |
C9—C8—H8 | 120.3 | H26A—C26—H26C | 109.5 |
C7—C8—H8 | 120.3 | H26B—C26—H26C | 109.5 |
C5—N1—C1—C2 | 0.5 (3) | C17—N3—C13—C19 | 178.34 (17) |
Ni1—N1—C1—C2 | 179.49 (15) | Ni1—N3—C13—C19 | −5.0 (2) |
C5—N1—C1—C7 | −179.44 (17) | N3—C13—C14—C15 | 0.2 (3) |
Ni1—N1—C1—C7 | −0.5 (2) | C19—C13—C14—C15 | −179.34 (19) |
N1—C1—C2—C3 | −0.3 (3) | C13—C14—C15—C16 | 1.0 (3) |
C7—C1—C2—C3 | 179.70 (18) | C14—C15—C16—C17 | −1.0 (3) |
C1—C2—C3—C4 | −0.4 (3) | C14—C15—C16—C18 | 178.50 (19) |
C2—C3—C4—C5 | 0.8 (3) | C13—N3—C17—C16 | 1.2 (3) |
C2—C3—C4—C6 | −178.3 (2) | Ni1—N3—C17—C16 | −175.11 (15) |
C1—N1—C5—C4 | −0.1 (3) | C15—C16—C17—N3 | 0.0 (3) |
Ni1—N1—C5—C4 | −178.94 (15) | C18—C16—C17—N3 | −179.57 (18) |
C3—C4—C5—N1 | −0.6 (3) | C23—N4—C19—C20 | −0.3 (3) |
C6—C4—C5—N1 | 178.56 (19) | Ni1—N4—C19—C20 | 176.39 (15) |
C11—N2—C7—C8 | 1.5 (3) | C23—N4—C19—C13 | −179.20 (17) |
Ni1—N2—C7—C8 | −179.70 (14) | Ni1—N4—C19—C13 | −2.5 (2) |
C11—N2—C7—C1 | −178.06 (16) | N3—C13—C19—N4 | 5.0 (3) |
Ni1—N2—C7—C1 | 0.7 (2) | C14—C13—C19—N4 | −175.41 (18) |
N1—C1—C7—N2 | −0.1 (2) | N3—C13—C19—C20 | −173.90 (18) |
C2—C1—C7—N2 | 179.88 (18) | C14—C13—C19—C20 | 5.7 (3) |
N1—C1—C7—C8 | −179.73 (18) | N4—C19—C20—C21 | 0.1 (3) |
C2—C1—C7—C8 | 0.3 (3) | C13—C19—C20—C21 | 178.98 (19) |
N2—C7—C8—C9 | −2.0 (3) | C19—C20—C21—C22 | −0.3 (3) |
C1—C7—C8—C9 | 177.59 (18) | C20—C21—C22—C23 | 0.6 (3) |
C7—C8—C9—C10 | 0.1 (3) | C20—C21—C22—C24 | −178.6 (2) |
C8—C9—C10—C11 | 2.1 (3) | C19—N4—C23—C22 | 0.6 (3) |
C8—C9—C10—C12 | −176.87 (19) | Ni1—N4—C23—C22 | −175.66 (15) |
C7—N2—C11—C10 | 0.8 (3) | C21—C22—C23—N4 | −0.8 (3) |
Ni1—N2—C11—C10 | −177.76 (14) | C24—C22—C23—N4 | 178.44 (19) |
C9—C10—C11—N2 | −2.6 (3) | Ni1—O1—C25—O2 | 1.4 (2) |
C12—C10—C11—N2 | 176.34 (19) | Ni1—O1—C25—C26 | −178.7 (2) |
C17—N3—C13—C14 | −1.3 (3) | Ni1—O2—C25—O1 | −1.3 (2) |
Ni1—N3—C13—C14 | 175.44 (15) | Ni1—O2—C25—C26 | 178.7 (2) |
Geometry of hydrogen bonds and other noncovalent interactions (Å, °) |
D—H···A | D—H | H···A | D···A | D—H···A |
O7A—H1W···O4 | 0.89 (1) | 2.19 (1) | 2.971 (5) | 147 (2) |
O7B—H1W···O4 | 0.89 (1) | 2.19 (1) | 3.011 (10) | 153 (2) |
O7A—H2W···O2 | 0.89 (1) | 2.13 (1) | 2.974 (5) | 159 (3) |
O7B—H3W···O7Ai | 0.89 (1) | 2.33 (5) | 3.144 (12) | 152 (11) |
O7B—H3W···O7Bi | 0.89 (1) | 2.46 (10) | 3.19 (2) | 140 (12) |
C2—H2···O1ii | 0.95 | 2.52 | 3.376 (3) | 151 |
C3—H3···O5iii | 0.95 | 2.37 | 3.285 (3) | 161 |
C5—H5···O2 | 0.95 | 2.64 | 3.198 (3) | 118 |
C20—H20···O2iv | 0.95 | 2.56 | 3.421 (3) | 152 |
C21—H21···O4iv | 0.95 | 2.33 | 3.267 (3) | 169 |
C23—H23···O1 | 0.95 | 2.60 | 3.158 (3) | 118 |
C23—H23···O5v | 0.95 | 2.60 | 3.187 (3) | 120 |
C26—H26A···O7Bi | 0.98 | 2.44 | 3.334 (11) | 151 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y, −z+2; (v) x, y−1, z. |