




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901500420X/zp2016sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S205698901500420X/zp2016Isup2.hkl |
CCDC reference: 1051597
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.031
- wR factor = 0.072
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H9WA .. H7O .. 2.04 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H9WB .. H7O .. 1.85 Ang.
Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 46 Report PLAT976_ALERT_2_C Check Calcd Residual Density 1.00A From O9 -0.42 eA-3
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 8 Report PLAT153_ALERT_1_G The su's on the Cell Axes are Equal .......... 0.00500 Ang. PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00500 Degree PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 63 Do ! O3 -NI1 -N1 -C1 154.20 0.50 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 68 Do ! O3 -NI1 -N1 -C5 -22.50 0.70 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 82 Do ! O2 -NI1 -N2 -C10 142.90 0.90 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 87 Do ! O2 -NI1 -N2 -C6 -37.40 1.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 97 Do ! N1 -NI1 -O3 -C14 168.80 0.60 1.555 1.555 1.555 1.555 PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 6 Note PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 1 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 10 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 2 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 15 ALERT level G = General information/check it is not something unexpected 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Imidazo[4,5-f][1,10]phenanthroline (IP) derivatives have been used to recognize the secondary structure of DNA in Ru(II) complexes. IP also an important heteroaromatic N-donor ligands for the construction of coordination polymers. A handful of comcpounds based on IP and carboxylate ligands have been described (Liu et al., 2009; Stephenson et al., 2008; Wu et al., 1997; Yang et al., 2010). The title compound was prepared during an attempt to prepare a coordination polymer containing both benzenetricarboxylate (BTC) and IP ligands, however, an simple dinuclear complex obtained.
Nickel nitrate hexahydrate and benzenetricarboxylate acid were obtained commercially. imidazo[4,5-f][1,10]phenanthroline was prepared via a published procedure (Wu et al. (1997). A mixture of Nickel nitrate hexahydrate (133 mg, 0.50 mmol), benzenetricarboxylate acid (105 mg, 0.50 mmol), imidazo[4,5-f][1,10]phenanthroline (0.110 g,0.5 mmol) and 10.0 g water (550 mmol) was placed into a 23 ml Teflon-lined Parr Acid Digestion bomb, which was then heated under autogenous pressure at 398 K for 72 h, then cooled to RT at a rate of 5 °c/h. The resulting green crystals of the title compound were obtained.
All H atoms were found in a difference Fourier map. The H atoms bound to C or N atoms were placed in calculated positions, with C—H= 0.93Å (CH) or N—H=0.86Å (NH)), Uiso(H)= 1.2 times Ueq(C or N). The H atoms bound to O atoms were restrained with O—H = 0.85 Å, and refined with Uiso(H)= 1.5 times Ueq(O).
Imidazo[4,5-f][1,10]phenanthroline (IP) derivatives have been used to recognize the secondary structure of DNA in Ru(II) complexes. IP also an important heteroaromatic N-donor ligands for the construction of coordination polymers. A handful of comcpounds based on IP and carboxylate ligands have been described (Liu et al., 2009; Stephenson et al., 2008; Wu et al., 1997; Yang et al., 2010). The title compound was prepared during an attempt to prepare a coordination polymer containing both benzenetricarboxylate (BTC) and IP ligands, however, an simple dinuclear complex obtained.
For general background, see: Stephenson et al. (2008). For details of the synthesis, see: Liu et al. (2009); Wu et al. (1997); Yang et al. (2010); Che et al. (2013).
Nickel nitrate hexahydrate and benzenetricarboxylate acid were obtained commercially. imidazo[4,5-f][1,10]phenanthroline was prepared via a published procedure (Wu et al. (1997). A mixture of Nickel nitrate hexahydrate (133 mg, 0.50 mmol), benzenetricarboxylate acid (105 mg, 0.50 mmol), imidazo[4,5-f][1,10]phenanthroline (0.110 g,0.5 mmol) and 10.0 g water (550 mmol) was placed into a 23 ml Teflon-lined Parr Acid Digestion bomb, which was then heated under autogenous pressure at 398 K for 72 h, then cooled to RT at a rate of 5 °c/h. The resulting green crystals of the title compound were obtained.
All H atoms were found in a difference Fourier map. The H atoms bound to C or N atoms were placed in calculated positions, with C—H= 0.93Å (CH) or N—H=0.86Å (NH)), Uiso(H)= 1.2 times Ueq(C or N). The H atoms bound to O atoms were restrained with O—H = 0.85 Å, and refined with Uiso(H)= 1.5 times Ueq(O).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Ni2(C9H4O6)2(C13H8N4)2(H2O)4]·2H2O | Z = 1 |
Mr = 1082.22 | F(000) = 556 |
Triclinic, P1 | Dx = 1.713 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 8.581 (5) Å | Cell parameters from 2586 reflections |
b = 9.032 (5) Å | θ = 3.6–24.9° |
c = 14.278 (5) Å | µ = 0.99 mm−1 |
α = 82.222 (5)° | T = 293 K |
β = 87.729 (5)° | Block, yellow-green |
γ = 73.117 (5)° | 0.28 × 0.16 × 0.15 mm |
V = 1049.2 (9) Å3 |
Bruker APEXII CCD diffractometer | 3851 independent reflections |
Radiation source: fine-focus sealed tube | 3050 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
phi and ω scans | θmax = 25.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −6→10 |
Tmin = 0.805, Tmax = 0.867 | k = −10→10 |
5594 measured reflections | l = −16→17 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0333P)2] where P = (Fo2 + 2Fc2)/3 |
3851 reflections | (Δ/σ)max = 0.001 |
325 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
[Ni2(C9H4O6)2(C13H8N4)2(H2O)4]·2H2O | γ = 73.117 (5)° |
Mr = 1082.22 | V = 1049.2 (9) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.581 (5) Å | Mo Kα radiation |
b = 9.032 (5) Å | µ = 0.99 mm−1 |
c = 14.278 (5) Å | T = 293 K |
α = 82.222 (5)° | 0.28 × 0.16 × 0.15 mm |
β = 87.729 (5)° |
Bruker APEXII CCD diffractometer | 3851 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 3050 reflections with I > 2σ(I) |
Tmin = 0.805, Tmax = 0.867 | Rint = 0.048 |
5594 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.30 e Å−3 |
3851 reflections | Δρmin = −0.43 e Å−3 |
325 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6312 (3) | 0.3200 (3) | 0.81421 (15) | 0.0288 (6) | |
H1 | 0.5473 | 0.4127 | 0.8124 | 0.035* | |
C2 | 0.6567 (3) | 0.2172 (3) | 0.89778 (16) | 0.0338 (6) | |
H2 | 0.5912 | 0.2413 | 0.9503 | 0.041* | |
C3 | 0.7796 (3) | 0.0801 (3) | 0.90156 (16) | 0.0310 (6) | |
H3 | 0.7976 | 0.0092 | 0.9565 | 0.037* | |
C4 | 0.8778 (3) | 0.0478 (3) | 0.82195 (15) | 0.0227 (5) | |
C5 | 0.8443 (3) | 0.1596 (2) | 0.74049 (15) | 0.0209 (5) | |
C6 | 0.9472 (3) | 0.1389 (2) | 0.65729 (15) | 0.0207 (5) | |
C7 | 1.0812 (3) | 0.0055 (3) | 0.65371 (15) | 0.0231 (5) | |
C8 | 1.1781 (3) | −0.0002 (3) | 0.57196 (16) | 0.0270 (5) | |
H8 | 1.2676 | −0.0861 | 0.5664 | 0.032* | |
C9 | 1.1399 (3) | 0.1215 (3) | 0.50060 (16) | 0.0280 (6) | |
H9 | 1.2038 | 0.1190 | 0.4464 | 0.034* | |
C10 | 1.0050 (3) | 0.2493 (3) | 0.50942 (15) | 0.0258 (5) | |
H10 | 0.9811 | 0.3315 | 0.4605 | 0.031* | |
C11 | 1.1089 (3) | −0.1101 (3) | 0.73572 (15) | 0.0252 (5) | |
C12 | 1.0117 (3) | −0.0873 (3) | 0.81472 (15) | 0.0243 (5) | |
C13 | 1.2023 (3) | −0.3077 (3) | 0.83840 (17) | 0.0369 (6) | |
H13 | 1.2656 | −0.4031 | 0.8682 | 0.044* | |
C14 | 0.5942 (3) | 0.6540 (2) | 0.43305 (15) | 0.0220 (5) | |
C15 | 0.6305 (3) | 0.7419 (3) | 0.34261 (15) | 0.0212 (5) | |
C16 | 0.7606 (3) | 0.6785 (3) | 0.28582 (15) | 0.0234 (5) | |
H16 | 0.8326 | 0.5814 | 0.3061 | 0.028* | |
C17 | 0.7849 (3) | 0.7588 (3) | 0.19821 (15) | 0.0223 (5) | |
C18 | 0.6787 (3) | 0.9059 (3) | 0.17046 (16) | 0.0264 (5) | |
H18 | 0.6933 | 0.9601 | 0.1122 | 0.032* | |
C19 | 0.5521 (3) | 0.9727 (3) | 0.22814 (15) | 0.0243 (5) | |
C20 | 0.5259 (3) | 0.8897 (3) | 0.31353 (15) | 0.0249 (5) | |
H20 | 0.4384 | 0.9329 | 0.3515 | 0.030* | |
C22 | 0.9187 (3) | 0.6874 (3) | 0.13265 (15) | 0.0240 (5) | |
C23 | 0.4356 (3) | 1.1296 (3) | 0.19953 (17) | 0.0288 (6) | |
Ni1 | 0.70279 (4) | 0.43502 (3) | 0.609962 (19) | 0.02230 (10) | |
N1 | 0.7200 (2) | 0.2927 (2) | 0.73743 (12) | 0.0229 (4) | |
N2 | 0.9089 (2) | 0.2582 (2) | 0.58513 (12) | 0.0217 (4) | |
N3 | 1.2298 (2) | −0.2516 (2) | 0.75156 (13) | 0.0329 (5) | |
N4 | 1.0757 (2) | −0.2163 (2) | 0.88009 (13) | 0.0315 (5) | |
H4 | 1.0409 | −0.2341 | 0.9366 | 0.038* | |
O1 | 0.83799 (18) | 0.55829 (17) | 0.66524 (10) | 0.0274 (4) | |
H1WA | 0.8974 | 0.5175 | 0.7162 | 0.041* | |
H1WB | 0.7704 | 0.6288 | 0.6903 | 0.041* | |
O2 | 0.48839 (19) | 0.60135 (19) | 0.63947 (11) | 0.0368 (4) | |
H2WA | 0.4226 | 0.6611 | 0.6785 | 0.055* | |
H2WB | 0.4306 | 0.6295 | 0.5865 | 0.055* | |
O3 | 0.71191 (18) | 0.56435 (17) | 0.48112 (10) | 0.0257 (4) | |
O4 | 0.44422 (18) | 0.67849 (17) | 0.45611 (10) | 0.0249 (4) | |
O5 | 1.0320 (2) | 0.57271 (19) | 0.16548 (11) | 0.0346 (4) | |
O6 | 0.9071 (2) | 0.74669 (19) | 0.04712 (11) | 0.0365 (4) | |
O7 | 0.4671 (2) | 1.19600 (19) | 0.11669 (12) | 0.0474 (5) | |
H7O | 0.3828 | 1.2679 | 0.0956 | 0.071* | |
O8 | 0.3214 (2) | 1.18626 (19) | 0.24846 (12) | 0.0436 (5) | |
O9 | 0.7523 (2) | 0.56589 (19) | 0.96006 (11) | 0.0404 (5) | |
H9WA | 0.8263 | 0.5505 | 0.9168 | 0.061* | |
H9WB | 0.7762 | 0.6295 | 0.9933 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0238 (13) | 0.0318 (14) | 0.0252 (13) | −0.0005 (11) | 0.0062 (11) | −0.0021 (10) |
C2 | 0.0336 (15) | 0.0396 (15) | 0.0225 (12) | −0.0044 (12) | 0.0105 (11) | −0.0014 (11) |
C3 | 0.0342 (15) | 0.0327 (14) | 0.0205 (12) | −0.0051 (12) | 0.0044 (11) | 0.0044 (10) |
C4 | 0.0225 (12) | 0.0254 (12) | 0.0193 (11) | −0.0073 (10) | 0.0023 (10) | 0.0007 (9) |
C5 | 0.0202 (12) | 0.0238 (12) | 0.0181 (11) | −0.0062 (10) | 0.0009 (10) | −0.0007 (9) |
C6 | 0.0190 (12) | 0.0242 (12) | 0.0186 (11) | −0.0064 (10) | 0.0004 (9) | −0.0010 (9) |
C7 | 0.0211 (12) | 0.0260 (12) | 0.0216 (12) | −0.0066 (10) | 0.0024 (10) | −0.0027 (10) |
C8 | 0.0240 (13) | 0.0257 (13) | 0.0286 (13) | −0.0039 (11) | 0.0050 (11) | −0.0028 (10) |
C9 | 0.0266 (13) | 0.0334 (14) | 0.0217 (12) | −0.0068 (11) | 0.0088 (10) | −0.0021 (10) |
C10 | 0.0276 (13) | 0.0297 (13) | 0.0192 (11) | −0.0090 (11) | 0.0029 (10) | 0.0012 (10) |
C11 | 0.0252 (13) | 0.0224 (12) | 0.0252 (12) | −0.0040 (11) | 0.0023 (11) | −0.0001 (10) |
C12 | 0.0249 (13) | 0.0258 (12) | 0.0201 (11) | −0.0061 (11) | 0.0023 (10) | 0.0009 (10) |
C13 | 0.0355 (15) | 0.0277 (14) | 0.0354 (15) | 0.0038 (12) | 0.0040 (12) | 0.0084 (11) |
C14 | 0.0252 (13) | 0.0221 (12) | 0.0179 (11) | −0.0054 (11) | 0.0030 (10) | −0.0034 (9) |
C15 | 0.0205 (12) | 0.0250 (12) | 0.0171 (11) | −0.0063 (10) | 0.0003 (10) | 0.0005 (9) |
C16 | 0.0212 (12) | 0.0223 (12) | 0.0224 (12) | −0.0016 (10) | −0.0021 (10) | 0.0024 (9) |
C17 | 0.0197 (12) | 0.0258 (12) | 0.0198 (11) | −0.0051 (10) | 0.0002 (10) | 0.0003 (9) |
C18 | 0.0273 (13) | 0.0277 (13) | 0.0208 (12) | −0.0062 (11) | 0.0017 (10) | 0.0037 (10) |
C19 | 0.0229 (13) | 0.0240 (12) | 0.0235 (12) | −0.0046 (11) | −0.0003 (10) | 0.0013 (10) |
C20 | 0.0214 (12) | 0.0286 (13) | 0.0228 (12) | −0.0045 (11) | 0.0051 (10) | −0.0041 (10) |
C22 | 0.0237 (13) | 0.0253 (13) | 0.0224 (12) | −0.0071 (11) | 0.0016 (10) | −0.0010 (10) |
C23 | 0.0291 (14) | 0.0255 (13) | 0.0290 (13) | −0.0050 (11) | −0.0001 (12) | −0.0003 (11) |
Ni1 | 0.01924 (16) | 0.02540 (17) | 0.01782 (16) | −0.00195 (13) | 0.00227 (12) | 0.00200 (12) |
N1 | 0.0193 (10) | 0.0253 (10) | 0.0215 (10) | −0.0036 (9) | 0.0017 (8) | −0.0006 (8) |
N2 | 0.0219 (10) | 0.0243 (10) | 0.0166 (9) | −0.0055 (9) | 0.0021 (8) | 0.0017 (8) |
N3 | 0.0295 (12) | 0.0291 (11) | 0.0283 (11) | 0.0053 (10) | 0.0070 (9) | 0.0043 (9) |
N4 | 0.0333 (12) | 0.0313 (12) | 0.0214 (10) | −0.0019 (10) | 0.0070 (9) | 0.0077 (9) |
O1 | 0.0260 (9) | 0.0286 (9) | 0.0230 (8) | −0.0014 (7) | −0.0001 (7) | −0.0022 (7) |
O2 | 0.0285 (10) | 0.0466 (11) | 0.0211 (9) | 0.0106 (8) | 0.0009 (7) | −0.0027 (8) |
O3 | 0.0202 (8) | 0.0312 (9) | 0.0202 (8) | −0.0030 (7) | 0.0009 (7) | 0.0065 (7) |
O4 | 0.0200 (8) | 0.0314 (9) | 0.0201 (8) | −0.0044 (7) | 0.0038 (7) | −0.0001 (7) |
O5 | 0.0287 (10) | 0.0391 (10) | 0.0238 (9) | 0.0074 (8) | 0.0002 (7) | 0.0006 (8) |
O6 | 0.0357 (10) | 0.0424 (11) | 0.0201 (9) | 0.0012 (9) | 0.0069 (8) | 0.0063 (8) |
O7 | 0.0398 (11) | 0.0397 (11) | 0.0407 (11) | 0.0114 (9) | 0.0098 (9) | 0.0172 (9) |
O8 | 0.0469 (12) | 0.0290 (10) | 0.0425 (11) | 0.0061 (9) | 0.0138 (10) | −0.0032 (8) |
O9 | 0.0411 (11) | 0.0382 (10) | 0.0320 (10) | 0.0021 (9) | 0.0049 (8) | −0.0016 (8) |
C1—N1 | 1.319 (3) | C15—C16 | 1.384 (3) |
C1—C2 | 1.392 (3) | C15—C20 | 1.394 (3) |
C1—H1 | 0.9300 | C16—C17 | 1.399 (3) |
C2—C3 | 1.370 (3) | C16—H16 | 0.9300 |
C2—H2 | 0.9300 | C17—C18 | 1.391 (3) |
C3—C4 | 1.399 (3) | C17—C22 | 1.503 (3) |
C3—H3 | 0.9300 | C18—C19 | 1.381 (3) |
C4—C5 | 1.413 (3) | C18—H18 | 0.9300 |
C4—C12 | 1.425 (3) | C19—C20 | 1.388 (3) |
C5—N1 | 1.353 (3) | C19—C23 | 1.492 (3) |
C5—C6 | 1.451 (3) | C20—H20 | 0.9300 |
C6—N2 | 1.361 (3) | C22—O5 | 1.248 (3) |
C6—C7 | 1.408 (3) | C22—O6 | 1.261 (3) |
C7—C8 | 1.404 (3) | C23—O8 | 1.209 (3) |
C7—C11 | 1.437 (3) | C23—O7 | 1.307 (3) |
C8—C9 | 1.367 (3) | Ni1—O3 | 2.0531 (16) |
C8—H8 | 0.9300 | Ni1—N1 | 2.0652 (19) |
C9—C10 | 1.392 (3) | Ni1—N2 | 2.066 (2) |
C9—H9 | 0.9300 | Ni1—O1 | 2.0662 (17) |
C10—N2 | 1.330 (3) | Ni1—O2 | 2.0794 (18) |
C10—H10 | 0.9300 | Ni1—O4i | 2.1540 (17) |
C11—C12 | 1.378 (3) | N4—H4 | 0.8600 |
C11—N3 | 1.390 (3) | O1—H1WA | 0.8794 |
C12—N4 | 1.380 (3) | O1—H1WB | 0.8376 |
C13—N3 | 1.314 (3) | O2—H2WA | 0.8944 |
C13—N4 | 1.333 (3) | O2—H2WB | 0.8873 |
C13—H13 | 0.9300 | O4—Ni1i | 2.1540 (17) |
C14—O3 | 1.255 (3) | O7—H7O | 0.8528 |
C14—O4 | 1.279 (3) | O9—H9WA | 0.8627 |
C14—C15 | 1.493 (3) | O9—H9WB | 0.8651 |
N1—C1—C2 | 123.3 (2) | C19—C18—C17 | 121.0 (2) |
N1—C1—H1 | 118.3 | C19—C18—H18 | 119.5 |
C2—C1—H1 | 118.3 | C17—C18—H18 | 119.5 |
C3—C2—C1 | 119.0 (2) | C18—C19—C20 | 119.7 (2) |
C3—C2—H2 | 120.5 | C18—C19—C23 | 122.0 (2) |
C1—C2—H2 | 120.5 | C20—C19—C23 | 118.2 (2) |
C2—C3—C4 | 119.3 (2) | C19—C20—C15 | 120.2 (2) |
C2—C3—H3 | 120.3 | C19—C20—H20 | 119.9 |
C4—C3—H3 | 120.3 | C15—C20—H20 | 119.9 |
C3—C4—C5 | 117.8 (2) | O5—C22—O6 | 124.3 (2) |
C3—C4—C12 | 126.4 (2) | O5—C22—C17 | 118.4 (2) |
C5—C4—C12 | 115.84 (19) | O6—C22—C17 | 117.2 (2) |
N1—C5—C4 | 122.0 (2) | O8—C23—O7 | 124.1 (2) |
N1—C5—C6 | 117.03 (19) | O8—C23—C19 | 122.2 (2) |
C4—C5—C6 | 120.9 (2) | O7—C23—C19 | 113.7 (2) |
N2—C6—C7 | 122.7 (2) | O3—Ni1—N1 | 173.78 (7) |
N2—C6—C5 | 115.78 (19) | O3—Ni1—N2 | 94.05 (7) |
C7—C6—C5 | 121.52 (19) | N1—Ni1—N2 | 80.10 (7) |
C8—C7—C6 | 117.2 (2) | O3—Ni1—O1 | 88.33 (7) |
C8—C7—C11 | 126.1 (2) | N1—Ni1—O1 | 89.79 (7) |
C6—C7—C11 | 116.7 (2) | N2—Ni1—O1 | 92.10 (8) |
C9—C8—C7 | 119.5 (2) | O3—Ni1—O2 | 89.01 (6) |
C9—C8—H8 | 120.2 | N1—Ni1—O2 | 96.93 (7) |
C7—C8—H8 | 120.2 | N2—Ni1—O2 | 176.09 (7) |
C8—C9—C10 | 119.8 (2) | O1—Ni1—O2 | 90.43 (8) |
C8—C9—H9 | 120.1 | O3—Ni1—O4i | 87.63 (6) |
C10—C9—H9 | 120.1 | N1—Ni1—O4i | 94.41 (7) |
N2—C10—C9 | 122.6 (2) | N2—Ni1—O4i | 89.96 (8) |
N2—C10—H10 | 118.7 | O1—Ni1—O4i | 175.58 (6) |
C9—C10—H10 | 118.7 | O2—Ni1—O4i | 87.72 (8) |
C12—C11—N3 | 109.89 (19) | C1—N1—C5 | 118.49 (19) |
C12—C11—C7 | 121.0 (2) | C1—N1—Ni1 | 128.11 (16) |
N3—C11—C7 | 129.1 (2) | C5—N1—Ni1 | 113.32 (14) |
C11—C12—N4 | 105.6 (2) | C10—N2—C6 | 118.2 (2) |
C11—C12—C4 | 123.9 (2) | C10—N2—Ni1 | 128.14 (16) |
N4—C12—C4 | 130.4 (2) | C6—N2—Ni1 | 113.64 (14) |
N3—C13—N4 | 114.2 (2) | C13—N3—C11 | 103.84 (19) |
N3—C13—H13 | 122.9 | C13—N4—C12 | 106.45 (19) |
N4—C13—H13 | 122.9 | C13—N4—H4 | 126.8 |
O3—C14—O4 | 125.1 (2) | C12—N4—H4 | 126.8 |
O3—C14—C15 | 118.1 (2) | Ni1—O1—H1WA | 120.3 |
O4—C14—C15 | 116.79 (19) | Ni1—O1—H1WB | 105.6 |
C16—C15—C20 | 119.6 (2) | H1WA—O1—H1WB | 96.1 |
C16—C15—C14 | 121.87 (19) | Ni1—O2—H2WA | 152.1 |
C20—C15—C14 | 118.51 (19) | Ni1—O2—H2WB | 106.7 |
C15—C16—C17 | 120.7 (2) | H2WA—O2—H2WB | 101.2 |
C15—C16—H16 | 119.7 | C14—O3—Ni1 | 127.43 (14) |
C17—C16—H16 | 119.7 | C14—O4—Ni1i | 119.27 (14) |
C18—C17—C16 | 118.7 (2) | C23—O7—H7O | 109.8 |
C18—C17—C22 | 119.7 (2) | H9WA—O9—H9WB | 105.2 |
C16—C17—C22 | 121.5 (2) | ||
N1—C1—C2—C3 | −0.1 (4) | C18—C19—C23—O8 | 177.5 (2) |
C1—C2—C3—C4 | 0.9 (4) | C20—C19—C23—O8 | 0.7 (4) |
C2—C3—C4—C5 | −0.2 (4) | C18—C19—C23—O7 | −0.9 (3) |
C2—C3—C4—C12 | 178.8 (2) | C20—C19—C23—O7 | −177.7 (2) |
C3—C4—C5—N1 | −1.4 (3) | C2—C1—N1—C5 | −1.4 (4) |
C12—C4—C5—N1 | 179.49 (19) | C2—C1—N1—Ni1 | −177.93 (17) |
C3—C4—C5—C6 | 176.1 (2) | C4—C5—N1—C1 | 2.2 (3) |
C12—C4—C5—C6 | −3.1 (3) | C6—C5—N1—C1 | −175.4 (2) |
N1—C5—C6—N2 | 1.3 (3) | C4—C5—N1—Ni1 | 179.18 (17) |
C4—C5—C6—N2 | −176.32 (19) | C6—C5—N1—Ni1 | 1.6 (2) |
N1—C5—C6—C7 | 179.14 (19) | O3—Ni1—N1—C1 | 154.2 (5) |
C4—C5—C6—C7 | 1.6 (3) | N2—Ni1—N1—C1 | 174.0 (2) |
N2—C6—C7—C8 | 0.9 (3) | O1—Ni1—N1—C1 | 81.8 (2) |
C5—C6—C7—C8 | −176.9 (2) | O2—Ni1—N1—C1 | −8.6 (2) |
N2—C6—C7—C11 | 178.9 (2) | O4i—Ni1—N1—C1 | −96.8 (2) |
C5—C6—C7—C11 | 1.1 (3) | O3—Ni1—N1—C5 | −22.5 (7) |
C6—C7—C8—C9 | 0.2 (3) | N2—Ni1—N1—C5 | −2.66 (15) |
C11—C7—C8—C9 | −177.6 (2) | O1—Ni1—N1—C5 | −94.83 (16) |
C7—C8—C9—C10 | −0.4 (4) | O2—Ni1—N1—C5 | 174.76 (15) |
C8—C9—C10—N2 | −0.5 (4) | O4i—Ni1—N1—C5 | 86.53 (15) |
C8—C7—C11—C12 | 175.6 (2) | C9—C10—N2—C6 | 1.5 (3) |
C6—C7—C11—C12 | −2.2 (3) | C9—C10—N2—Ni1 | −178.89 (16) |
C8—C7—C11—N3 | −2.5 (4) | C7—C6—N2—C10 | −1.7 (3) |
C6—C7—C11—N3 | 179.7 (2) | C5—C6—N2—C10 | 176.17 (19) |
N3—C11—C12—N4 | 0.7 (3) | C7—C6—N2—Ni1 | 178.65 (16) |
C7—C11—C12—N4 | −177.7 (2) | C5—C6—N2—Ni1 | −3.5 (2) |
N3—C11—C12—C4 | 179.1 (2) | O3—Ni1—N2—C10 | 1.62 (19) |
C7—C11—C12—C4 | 0.7 (4) | N1—Ni1—N2—C10 | −176.3 (2) |
C3—C4—C12—C11 | −177.0 (2) | O1—Ni1—N2—C10 | −86.85 (19) |
C5—C4—C12—C11 | 2.0 (3) | O2—Ni1—N2—C10 | 142.9 (9) |
C3—C4—C12—N4 | 0.9 (4) | O4i—Ni1—N2—C10 | 89.23 (19) |
C5—C4—C12—N4 | 179.9 (2) | O3—Ni1—N2—C6 | −178.76 (15) |
O3—C14—C15—C16 | 34.7 (3) | N1—Ni1—N2—C6 | 3.35 (15) |
O4—C14—C15—C16 | −146.4 (2) | O1—Ni1—N2—C6 | 92.77 (15) |
O3—C14—C15—C20 | −147.8 (2) | O2—Ni1—N2—C6 | −37.4 (10) |
O4—C14—C15—C20 | 31.1 (3) | O4i—Ni1—N2—C6 | −91.14 (15) |
C20—C15—C16—C17 | −2.2 (3) | N4—C13—N3—C11 | −0.1 (3) |
C14—C15—C16—C17 | 175.4 (2) | C12—C11—N3—C13 | −0.4 (3) |
C15—C16—C17—C18 | 2.0 (3) | C7—C11—N3—C13 | 177.8 (2) |
C15—C16—C17—C22 | −175.8 (2) | N3—C13—N4—C12 | 0.5 (3) |
C16—C17—C18—C19 | 0.4 (3) | C11—C12—N4—C13 | −0.7 (3) |
C22—C17—C18—C19 | 178.3 (2) | C4—C12—N4—C13 | −178.9 (2) |
C17—C18—C19—C20 | −2.6 (3) | O4—C14—O3—Ni1 | −1.4 (3) |
C17—C18—C19—C23 | −179.4 (2) | C15—C14—O3—Ni1 | 177.45 (13) |
C18—C19—C20—C15 | 2.3 (3) | N1—Ni1—O3—C14 | 168.8 (6) |
C23—C19—C20—C15 | 179.2 (2) | N2—Ni1—O3—C14 | 149.23 (18) |
C16—C15—C20—C19 | 0.0 (3) | O1—Ni1—O3—C14 | −118.78 (18) |
C14—C15—C20—C19 | −177.6 (2) | O2—Ni1—O3—C14 | −28.32 (18) |
C18—C17—C22—O5 | 165.0 (2) | O4i—Ni1—O3—C14 | 59.44 (18) |
C16—C17—C22—O5 | −17.2 (3) | O3—C14—O4—Ni1i | −101.9 (2) |
C18—C17—C22—O6 | −16.0 (3) | C15—C14—O4—Ni1i | 79.2 (2) |
C16—C17—C22—O6 | 161.7 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O6ii | 0.86 | 1.93 | 2.772 (3) | 165 |
O1—H1WA···O5iii | 0.88 | 1.82 | 2.676 (2) | 165 |
O1—H1WB···O8iv | 0.84 | 1.94 | 2.741 (2) | 161 |
O2—H2WA···N3v | 0.89 | 1.94 | 2.798 (3) | 160 |
O2—H2WB···O4 | 0.89 | 1.86 | 2.630 (2) | 144 |
O7—H7O···O9iv | 0.85 | 1.72 | 2.558 (2) | 166 |
O9—H9WA···O5iii | 0.86 | 1.88 | 2.684 (2) | 153 |
O9—H9WB···O6vi | 0.87 | 1.99 | 2.813 (3) | 159 |
Symmetry codes: (ii) x, y−1, z+1; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+2, −z+1; (v) x−1, y+1, z; (vi) x, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O6i | 0.86 | 1.93 | 2.772 (3) | 164.8 |
O1—H1WA···O5ii | 0.88 | 1.82 | 2.676 (2) | 164.5 |
O1—H1WB···O8iii | 0.84 | 1.94 | 2.741 (2) | 160.8 |
O2—H2WA···N3iv | 0.89 | 1.94 | 2.798 (3) | 159.5 |
O2—H2WB···O4 | 0.89 | 1.86 | 2.630 (2) | 143.8 |
O7—H7O···O9iii | 0.85 | 1.72 | 2.558 (2) | 165.8 |
O9—H9WA···O5ii | 0.86 | 1.88 | 2.684 (2) | 153.4 |
O9—H9WB···O6v | 0.87 | 1.99 | 2.813 (3) | 159.4 |
Symmetry codes: (i) x, y−1, z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) x−1, y+1, z; (v) x, y, z+1. |