Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030941/ww6413sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030941/ww6413Isup2.hkl |
CCDC reference: 287754
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.146
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level C SHFSU01_ALERT_2_C The absolute value of parameter shift to su ratio > 0.05 Absolute value of the parameter shift to su ratio given 0.052 Additional refinement cycles may be required. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.07 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 83.00 A 3 PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.856(18) ...... 2.22 su-Rat N6 -H6A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.856(18) ...... 2.22 su-Rat N8 -H8A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.89(4), Rep 0.885(18) ...... 2.22 su-Rat N10 -H10A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.845(18) ...... 2.22 su-Rat N16 -H16A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(4), Rep 0.856(18) ...... 2.22 su-Rat N6 -H6A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(4), Rep 0.856(18) ...... 2.22 su-Rat N8 -H8A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.89(4), Rep 0.885(18) ...... 2.22 su-Rat N10 -H10A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.89(4), Rep 0.885(18) ...... 2.22 su-Rat N10 -H10A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.845(18) ...... 2.22 su-Rat N16 -H16A 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 9 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
All reagents were of AR grade from commercial sources and used without further purification. Biimidazole was prepared following a slightly modified procedure (Ramirez et al., 2002) of Fieselmann et al. (1978). Ni(CH3COO)2 (124.43 mg, 0.5 mmol), phthalic acid (83.074 mg, 0.5 mmol) and H2biim (67.07 mg, 0.5 mmol) in a 1:1:1 molar ratio were added directly as a solid in deionized water (10 ml); after the mixture was stirred at room temperature for 30 min, a purple precipitate was obtained. The pH was adjusted to 7.0 using aqueous KOH solution. Then the mixture was placed in a 25 ml Teflon-lined stainless steel vessel and heated at 433 K for 4 d. The reaction vessel was allowed to cool to room temperature slowly, and purple crystals of title complex were obtained and collected by filtration and washed with water (yield 60%).
H atoms on C atoms were treated as riding, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq of the parent atom. H atoms on N atoms were refined with Uiso(H) = 0.08 Å and N—H distances in the range 0.84–0.90 Å. The final electron-density maximum and minimum are ?.?? and ?.??Å from atoms ?? and ??, respectively.
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 2000); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC.
[Ni(C6H6N4)3](C8H4O4) | F(000) = 2576 |
Mr = 625.27 | Dx = 1.473 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7467 reflections |
a = 23.5242 (18) Å | θ = 2.4–24.2° |
b = 11.1168 (9) Å | µ = 0.74 mm−1 |
c = 23.8578 (19) Å | T = 298 K |
β = 115.325 (1)° | Block, purple |
V = 5639.5 (8) Å3 | 0.49 × 0.19 × 0.15 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 13575 independent reflections |
Radiation source: fine-focus sealed tube | 9366 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ϕ and ω scans | θmax = 28.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −15→30 |
Tmin = 0.712, Tmax = 0.897 | k = −14→14 |
34502 measured reflections | l = −31→27 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.086P)2 + 0.3746P] where P = (Fo2 + 2Fc2)/3 |
13575 reflections | (Δ/σ)max = 0.052 |
811 parameters | Δρmax = 0.85 e Å−3 |
12 restraints | Δρmin = −0.41 e Å−3 |
[Ni(C6H6N4)3](C8H4O4) | V = 5639.5 (8) Å3 |
Mr = 625.27 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 23.5242 (18) Å | µ = 0.74 mm−1 |
b = 11.1168 (9) Å | T = 298 K |
c = 23.8578 (19) Å | 0.49 × 0.19 × 0.15 mm |
β = 115.325 (1)° |
Bruker SMART CCD area-detector diffractometer | 13575 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | 9366 reflections with I > 2σ(I) |
Tmin = 0.712, Tmax = 0.897 | Rint = 0.029 |
34502 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 12 restraints |
wR(F2) = 0.146 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.85 e Å−3 |
13575 reflections | Δρmin = −0.41 e Å−3 |
811 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. 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 > σ(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 | ||
Ni1 | 0.297972 (15) | 0.43282 (3) | 0.408920 (14) | 0.03367 (10) | |
Ni2 | 0.218476 (15) | 0.99385 (3) | 0.146530 (14) | 0.03460 (10) | |
N1 | 0.26147 (10) | 0.59208 (18) | 0.43033 (9) | 0.0367 (5) | |
N2 | 0.28603 (11) | 0.7669 (2) | 0.47927 (10) | 0.0435 (5) | |
N3 | 0.37989 (10) | 0.50533 (18) | 0.47939 (10) | 0.0377 (5) | |
N4 | 0.41950 (11) | 0.6427 (2) | 0.55256 (11) | 0.0479 (6) | |
N5 | 0.30319 (11) | 0.52657 (18) | 0.33531 (10) | 0.0389 (5) | |
N6 | 0.34006 (11) | 0.5351 (2) | 0.26440 (10) | 0.0403 (5) | |
N7 | 0.35223 (10) | 0.31181 (17) | 0.38177 (9) | 0.0362 (5) | |
N8 | 0.40765 (10) | 0.2910 (2) | 0.32733 (10) | 0.0391 (5) | |
N9 | 0.20945 (10) | 0.35107 (19) | 0.35689 (9) | 0.0401 (5) | |
N10 | 0.14189 (12) | 0.2119 (2) | 0.35506 (11) | 0.0553 (6) | |
N11 | 0.29316 (10) | 0.31317 (18) | 0.47335 (9) | 0.0386 (5) | |
N12 | 0.24568 (11) | 0.1590 (2) | 0.49308 (11) | 0.0434 (5) | |
N13 | 0.13287 (10) | 0.93047 (19) | 0.14267 (10) | 0.0405 (5) | |
N14 | 0.08147 (12) | 0.8645 (3) | 0.19503 (12) | 0.0624 (7) | |
N15 | 0.24260 (10) | 0.9692 (2) | 0.24232 (10) | 0.0401 (5) | |
N16 | 0.20404 (12) | 0.9506 (2) | 0.31144 (11) | 0.0501 (6) | |
N17 | 0.20183 (10) | 1.17884 (19) | 0.15165 (9) | 0.0401 (5) | |
N18 | 0.17531 (11) | 1.3507 (2) | 0.09995 (11) | 0.0468 (6) | |
N19 | 0.17682 (10) | 1.03775 (19) | 0.05296 (10) | 0.0393 (5) | |
N20 | 0.12721 (11) | 1.1743 (2) | −0.01800 (10) | 0.0409 (5) | |
N21 | 0.24696 (9) | 0.82579 (17) | 0.12880 (9) | 0.0353 (4) | |
N22 | 0.32457 (11) | 0.7124 (2) | 0.13068 (10) | 0.0427 (5) | |
N23 | 0.31277 (10) | 1.02870 (18) | 0.16627 (10) | 0.0378 (5) | |
N24 | 0.40652 (11) | 0.9503 (2) | 0.19168 (11) | 0.0447 (5) | |
O1 | 0.05404 (14) | 0.8068 (3) | 0.28947 (11) | 0.0933 (9) | |
O2 | 0.11296 (9) | 0.94959 (18) | 0.35324 (9) | 0.0486 (5) | |
O3 | 0.07251 (10) | 1.11458 (17) | 0.42695 (10) | 0.0542 (5) | |
O4 | 0.15186 (9) | 1.00862 (17) | 0.49594 (9) | 0.0515 (5) | |
O5 | 0.38970 (9) | 0.45284 (18) | 0.18420 (8) | 0.0452 (4) | |
O6 | 0.47094 (8) | 0.36130 (19) | 0.25923 (8) | 0.0492 (5) | |
O7 | 0.43473 (9) | 0.64905 (16) | 0.12601 (9) | 0.0478 (5) | |
O8 | 0.36762 (10) | 0.55685 (19) | 0.04029 (10) | 0.0600 (6) | |
C1 | 0.20933 (13) | 0.6636 (2) | 0.40975 (12) | 0.0426 (6) | |
H1 | 0.1698 | 0.6421 | 0.3798 | 0.051* | |
C2 | 0.22402 (14) | 0.7715 (3) | 0.43985 (13) | 0.0477 (7) | |
H2 | 0.1968 | 0.8357 | 0.4344 | 0.057* | |
C3 | 0.30681 (12) | 0.6582 (2) | 0.47202 (11) | 0.0368 (5) | |
C4 | 0.36914 (12) | 0.6076 (2) | 0.50169 (11) | 0.0369 (5) | |
C5 | 0.43941 (13) | 0.4727 (2) | 0.51891 (15) | 0.0499 (7) | |
H5 | 0.4598 | 0.4035 | 0.5153 | 0.060* | |
C6 | 0.46448 (14) | 0.5557 (3) | 0.56412 (16) | 0.0594 (8) | |
H6 | 0.5045 | 0.5543 | 0.5968 | 0.071* | |
C7 | 0.28361 (14) | 0.6318 (2) | 0.30273 (12) | 0.0460 (6) | |
H7 | 0.2590 | 0.6902 | 0.3097 | 0.055* | |
C8 | 0.30544 (14) | 0.6376 (3) | 0.25912 (13) | 0.0496 (7) | |
H8 | 0.2984 | 0.6995 | 0.2307 | 0.060* | |
C9 | 0.33727 (12) | 0.4707 (2) | 0.31076 (11) | 0.0342 (5) | |
C10 | 0.36553 (11) | 0.3573 (2) | 0.33751 (10) | 0.0327 (5) | |
C11 | 0.38889 (12) | 0.2096 (2) | 0.40123 (12) | 0.0414 (6) | |
H11 | 0.3900 | 0.1579 | 0.4323 | 0.050* | |
C12 | 0.42288 (12) | 0.1965 (2) | 0.36820 (12) | 0.0436 (6) | |
H12 | 0.4512 | 0.1351 | 0.3723 | 0.052* | |
C13 | 0.15663 (15) | 0.3584 (3) | 0.30223 (13) | 0.0576 (8) | |
H13 | 0.1507 | 0.4131 | 0.2707 | 0.069* | |
C14 | 0.11430 (16) | 0.2748 (3) | 0.30066 (14) | 0.0688 (10) | |
H14 | 0.0744 | 0.2624 | 0.2690 | 0.083* | |
C15 | 0.19849 (12) | 0.2621 (2) | 0.38807 (12) | 0.0390 (6) | |
C16 | 0.24462 (11) | 0.2397 (2) | 0.45072 (11) | 0.0362 (5) | |
C17 | 0.32740 (13) | 0.2781 (2) | 0.53414 (12) | 0.0444 (6) | |
H17 | 0.3646 | 0.3135 | 0.5620 | 0.053* | |
C18 | 0.29822 (13) | 0.1841 (3) | 0.54666 (12) | 0.0461 (6) | |
H18 | 0.3112 | 0.1441 | 0.5844 | 0.055* | |
C19 | 0.07590 (14) | 0.8848 (3) | 0.10163 (14) | 0.0575 (8) | |
H19 | 0.0613 | 0.8826 | 0.0587 | 0.069* | |
C20 | 0.04454 (15) | 0.8435 (4) | 0.13380 (15) | 0.0724 (10) | |
H20 | 0.0051 | 0.8074 | 0.1172 | 0.087* | |
C21 | 0.13457 (12) | 0.9152 (2) | 0.19808 (12) | 0.0415 (6) | |
C22 | 0.19219 (12) | 0.9448 (2) | 0.25164 (12) | 0.0388 (6) | |
C23 | 0.28938 (14) | 0.9928 (3) | 0.30009 (13) | 0.0538 (8) | |
H23 | 0.3306 | 1.0131 | 0.3086 | 0.065* | |
C24 | 0.26602 (15) | 0.9817 (3) | 0.34299 (14) | 0.0624 (9) | |
H24 | 0.2879 | 0.9931 | 0.3856 | 0.075* | |
C25 | 0.21510 (15) | 1.2718 (3) | 0.19319 (13) | 0.0525 (7) | |
H25 | 0.2325 | 1.2633 | 0.2361 | 0.063* | |
C26 | 0.19875 (15) | 1.3796 (3) | 0.16170 (14) | 0.0560 (8) | |
H26 | 0.2028 | 1.4560 | 0.1788 | 0.067* | |
C27 | 0.17784 (12) | 1.2301 (2) | 0.09596 (12) | 0.0367 (5) | |
C28 | 0.16079 (12) | 1.1532 (2) | 0.04266 (11) | 0.0359 (5) | |
C29 | 0.15252 (14) | 0.9837 (2) | −0.00390 (12) | 0.0455 (6) | |
H29 | 0.1565 | 0.9026 | −0.0112 | 0.055* | |
C30 | 0.12160 (14) | 1.0672 (2) | −0.04827 (13) | 0.0477 (7) | |
H30 | 0.1008 | 1.0541 | −0.0908 | 0.057* | |
C31 | 0.35753 (14) | 1.1166 (3) | 0.19275 (13) | 0.0482 (7) | |
H31 | 0.3494 | 1.1963 | 0.1988 | 0.058* | |
C32 | 0.41485 (14) | 1.0689 (3) | 0.20844 (15) | 0.0550 (8) | |
H32 | 0.4531 | 1.1092 | 0.2272 | 0.066* | |
C33 | 0.34427 (12) | 0.9302 (2) | 0.16647 (11) | 0.0350 (5) | |
C34 | 0.30770 (11) | 0.8219 (2) | 0.14281 (11) | 0.0344 (5) | |
C35 | 0.22364 (13) | 0.7145 (2) | 0.10483 (12) | 0.0426 (6) | |
H35 | 0.1818 | 0.6910 | 0.0901 | 0.051* | |
C36 | 0.27134 (13) | 0.6445 (2) | 0.10613 (13) | 0.0469 (7) | |
H36 | 0.2683 | 0.5651 | 0.0928 | 0.056* | |
C37 | 0.07202 (13) | 0.8687 (3) | 0.33813 (13) | 0.0482 (7) | |
C38 | 0.04347 (12) | 0.8393 (2) | 0.38218 (12) | 0.0409 (6) | |
C39 | 0.00462 (15) | 0.7397 (3) | 0.37028 (15) | 0.0586 (8) | |
H39 | −0.0035 | 0.6931 | 0.3353 | 0.070* | |
C40 | −0.02237 (15) | 0.7087 (3) | 0.41005 (17) | 0.0645 (9) | |
H40 | −0.0497 | 0.6435 | 0.4009 | 0.077* | |
C41 | −0.00859 (14) | 0.7742 (3) | 0.46246 (15) | 0.0572 (8) | |
H41 | −0.0261 | 0.7531 | 0.4894 | 0.069* | |
C42 | 0.03107 (13) | 0.8715 (3) | 0.47567 (13) | 0.0474 (6) | |
H42 | 0.0405 | 0.9153 | 0.5118 | 0.057* | |
C43 | 0.05732 (11) | 0.9054 (2) | 0.43567 (12) | 0.0361 (5) | |
C44 | 0.09702 (13) | 1.0175 (2) | 0.45293 (13) | 0.0402 (6) | |
C45 | 0.44221 (12) | 0.4013 (2) | 0.20466 (11) | 0.0361 (5) | |
C46 | 0.47283 (11) | 0.3811 (2) | 0.16111 (11) | 0.0349 (5) | |
C47 | 0.51591 (13) | 0.2876 (2) | 0.17329 (13) | 0.0460 (6) | |
H47 | 0.5269 | 0.2420 | 0.2091 | 0.055* | |
C48 | 0.54272 (15) | 0.2614 (3) | 0.13323 (15) | 0.0585 (8) | |
H48 | 0.5719 | 0.1995 | 0.1425 | 0.070* | |
C49 | 0.52631 (15) | 0.3268 (3) | 0.07977 (15) | 0.0578 (8) | |
H49 | 0.5435 | 0.3080 | 0.0522 | 0.069* | |
C50 | 0.48446 (14) | 0.4200 (3) | 0.06723 (13) | 0.0478 (7) | |
H50 | 0.4740 | 0.4647 | 0.0312 | 0.057* | |
C51 | 0.45730 (11) | 0.4492 (2) | 0.10702 (11) | 0.0356 (5) | |
C52 | 0.41561 (13) | 0.5587 (2) | 0.09025 (13) | 0.0408 (6) | |
H6A | 0.3501 (17) | 0.509 (3) | 0.2361 (14) | 0.080* | |
H22A | 0.3615 (11) | 0.688 (3) | 0.1316 (16) | 0.080* | |
H8A | 0.4211 (16) | 0.312 (3) | 0.3006 (13) | 0.080* | |
H16A | 0.1833 (15) | 0.934 (3) | 0.3318 (15) | 0.080* | |
H14A | 0.0716 (16) | 0.829 (3) | 0.2220 (13) | 0.080* | |
H12A | 0.2172 (13) | 0.110 (3) | 0.4896 (17) | 0.080* | |
H20A | 0.1104 (16) | 1.243 (2) | −0.0336 (16) | 0.080* | |
H18A | 0.1632 (17) | 1.396 (3) | 0.0679 (12) | 0.080* | |
H24A | 0.4395 (12) | 0.912 (3) | 0.1982 (17) | 0.080* | |
H4A | 0.4190 (17) | 0.707 (2) | 0.5732 (15) | 0.080* | |
H2A | 0.3131 (14) | 0.820 (3) | 0.5006 (15) | 0.080* | |
H10A | 0.1183 (14) | 0.164 (3) | 0.3661 (16) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.04099 (19) | 0.03020 (17) | 0.03391 (17) | −0.00446 (13) | 0.01993 (14) | −0.00233 (12) |
Ni2 | 0.03643 (19) | 0.03113 (17) | 0.03620 (18) | 0.00230 (13) | 0.01550 (14) | 0.00068 (13) |
N1 | 0.0400 (12) | 0.0371 (11) | 0.0349 (11) | −0.0005 (9) | 0.0178 (9) | −0.0014 (9) |
N2 | 0.0478 (14) | 0.0362 (12) | 0.0445 (13) | 0.0033 (10) | 0.0177 (11) | −0.0056 (10) |
N3 | 0.0391 (12) | 0.0325 (11) | 0.0444 (12) | −0.0029 (9) | 0.0206 (10) | −0.0067 (9) |
N4 | 0.0447 (13) | 0.0404 (13) | 0.0521 (14) | −0.0014 (10) | 0.0144 (11) | −0.0146 (10) |
N5 | 0.0516 (13) | 0.0318 (10) | 0.0397 (11) | −0.0019 (9) | 0.0257 (10) | −0.0002 (9) |
N6 | 0.0499 (13) | 0.0416 (12) | 0.0350 (11) | −0.0039 (10) | 0.0235 (10) | 0.0005 (9) |
N7 | 0.0439 (12) | 0.0301 (10) | 0.0359 (11) | −0.0053 (9) | 0.0184 (9) | −0.0030 (8) |
N8 | 0.0389 (12) | 0.0405 (12) | 0.0402 (12) | −0.0046 (9) | 0.0192 (10) | −0.0067 (9) |
N9 | 0.0471 (13) | 0.0389 (11) | 0.0353 (11) | −0.0051 (10) | 0.0186 (10) | −0.0015 (9) |
N10 | 0.0536 (15) | 0.0609 (16) | 0.0458 (13) | −0.0223 (13) | 0.0159 (12) | −0.0017 (12) |
N11 | 0.0409 (12) | 0.0382 (11) | 0.0394 (11) | −0.0053 (9) | 0.0196 (10) | −0.0003 (9) |
N12 | 0.0445 (13) | 0.0370 (12) | 0.0514 (13) | −0.0036 (10) | 0.0232 (11) | 0.0070 (10) |
N13 | 0.0351 (12) | 0.0461 (13) | 0.0378 (11) | 0.0015 (10) | 0.0132 (9) | −0.0024 (9) |
N14 | 0.0423 (14) | 0.097 (2) | 0.0486 (15) | −0.0237 (14) | 0.0203 (12) | −0.0083 (14) |
N15 | 0.0376 (12) | 0.0440 (12) | 0.0375 (11) | −0.0069 (10) | 0.0149 (10) | −0.0025 (9) |
N16 | 0.0495 (14) | 0.0641 (16) | 0.0393 (13) | −0.0185 (12) | 0.0214 (11) | −0.0093 (11) |
N17 | 0.0459 (13) | 0.0356 (11) | 0.0387 (11) | 0.0010 (10) | 0.0179 (10) | −0.0039 (9) |
N18 | 0.0571 (15) | 0.0306 (11) | 0.0486 (13) | 0.0014 (10) | 0.0186 (12) | −0.0006 (10) |
N19 | 0.0479 (13) | 0.0344 (11) | 0.0383 (11) | 0.0041 (10) | 0.0210 (10) | −0.0008 (9) |
N20 | 0.0452 (13) | 0.0360 (11) | 0.0386 (11) | 0.0055 (10) | 0.0152 (10) | 0.0033 (9) |
N21 | 0.0362 (11) | 0.0269 (10) | 0.0409 (11) | 0.0014 (8) | 0.0146 (9) | 0.0021 (8) |
N22 | 0.0469 (13) | 0.0365 (11) | 0.0490 (13) | 0.0068 (10) | 0.0247 (11) | −0.0001 (10) |
N23 | 0.0423 (12) | 0.0312 (10) | 0.0408 (11) | −0.0031 (9) | 0.0188 (10) | 0.0015 (9) |
N24 | 0.0366 (12) | 0.0486 (14) | 0.0484 (13) | −0.0021 (10) | 0.0177 (11) | 0.0021 (11) |
O1 | 0.118 (2) | 0.115 (2) | 0.0648 (15) | −0.0619 (19) | 0.0566 (15) | −0.0397 (15) |
O2 | 0.0501 (12) | 0.0506 (11) | 0.0544 (12) | −0.0123 (9) | 0.0312 (10) | −0.0043 (9) |
O3 | 0.0579 (13) | 0.0338 (10) | 0.0655 (13) | −0.0020 (9) | 0.0213 (10) | 0.0012 (9) |
O4 | 0.0471 (12) | 0.0479 (11) | 0.0527 (12) | −0.0110 (9) | 0.0149 (10) | −0.0042 (9) |
O5 | 0.0415 (10) | 0.0577 (12) | 0.0409 (10) | 0.0081 (9) | 0.0218 (8) | 0.0034 (9) |
O6 | 0.0392 (10) | 0.0690 (13) | 0.0418 (10) | 0.0037 (9) | 0.0194 (8) | 0.0168 (9) |
O7 | 0.0500 (11) | 0.0328 (9) | 0.0651 (12) | 0.0013 (8) | 0.0289 (10) | 0.0003 (9) |
O8 | 0.0577 (13) | 0.0537 (13) | 0.0560 (13) | 0.0110 (10) | 0.0122 (11) | 0.0086 (10) |
C1 | 0.0414 (15) | 0.0471 (15) | 0.0382 (13) | −0.0008 (12) | 0.0161 (12) | 0.0021 (12) |
C2 | 0.0498 (17) | 0.0450 (15) | 0.0480 (16) | 0.0093 (13) | 0.0207 (13) | 0.0012 (12) |
C3 | 0.0447 (15) | 0.0311 (12) | 0.0380 (13) | 0.0005 (11) | 0.0211 (11) | −0.0033 (10) |
C4 | 0.0384 (14) | 0.0341 (12) | 0.0395 (13) | −0.0016 (11) | 0.0181 (11) | −0.0052 (10) |
C5 | 0.0403 (15) | 0.0379 (14) | 0.0687 (19) | 0.0025 (12) | 0.0207 (14) | −0.0108 (13) |
C6 | 0.0387 (16) | 0.0541 (18) | 0.068 (2) | 0.0035 (14) | 0.0065 (14) | −0.0132 (15) |
C7 | 0.0601 (18) | 0.0351 (14) | 0.0494 (15) | 0.0073 (12) | 0.0297 (14) | 0.0064 (12) |
C8 | 0.0657 (19) | 0.0427 (15) | 0.0435 (15) | 0.0057 (14) | 0.0262 (14) | 0.0121 (12) |
C9 | 0.0398 (14) | 0.0335 (12) | 0.0322 (12) | −0.0053 (10) | 0.0181 (11) | −0.0030 (10) |
C10 | 0.0341 (13) | 0.0316 (12) | 0.0323 (12) | −0.0070 (10) | 0.0140 (10) | −0.0069 (10) |
C11 | 0.0454 (15) | 0.0316 (12) | 0.0435 (14) | −0.0033 (11) | 0.0155 (12) | −0.0004 (11) |
C12 | 0.0414 (15) | 0.0351 (13) | 0.0508 (15) | 0.0022 (11) | 0.0164 (12) | −0.0016 (12) |
C13 | 0.065 (2) | 0.068 (2) | 0.0350 (14) | −0.0082 (16) | 0.0167 (14) | 0.0049 (14) |
C14 | 0.063 (2) | 0.086 (2) | 0.0413 (16) | −0.0248 (19) | 0.0069 (15) | 0.0001 (16) |
C15 | 0.0438 (14) | 0.0362 (13) | 0.0403 (13) | −0.0058 (11) | 0.0211 (12) | −0.0030 (11) |
C16 | 0.0382 (14) | 0.0330 (12) | 0.0407 (13) | −0.0008 (11) | 0.0202 (11) | 0.0002 (10) |
C17 | 0.0412 (15) | 0.0464 (15) | 0.0406 (14) | −0.0025 (12) | 0.0126 (12) | 0.0048 (12) |
C18 | 0.0430 (15) | 0.0494 (16) | 0.0415 (14) | 0.0028 (12) | 0.0138 (12) | 0.0133 (12) |
C19 | 0.0417 (16) | 0.079 (2) | 0.0423 (16) | −0.0043 (15) | 0.0085 (13) | −0.0077 (15) |
C20 | 0.0415 (17) | 0.113 (3) | 0.056 (2) | −0.0264 (19) | 0.0145 (15) | −0.0135 (19) |
C21 | 0.0345 (13) | 0.0481 (15) | 0.0416 (14) | −0.0022 (11) | 0.0161 (11) | −0.0053 (12) |
C22 | 0.0401 (14) | 0.0397 (13) | 0.0376 (13) | −0.0056 (11) | 0.0176 (11) | −0.0028 (11) |
C23 | 0.0418 (16) | 0.070 (2) | 0.0461 (16) | −0.0166 (14) | 0.0155 (13) | −0.0062 (14) |
C24 | 0.0515 (18) | 0.091 (3) | 0.0410 (16) | −0.0249 (17) | 0.0161 (14) | −0.0137 (16) |
C25 | 0.067 (2) | 0.0468 (16) | 0.0414 (15) | 0.0008 (14) | 0.0215 (14) | −0.0094 (12) |
C26 | 0.074 (2) | 0.0368 (15) | 0.0549 (17) | −0.0013 (14) | 0.0250 (16) | −0.0114 (13) |
C27 | 0.0369 (13) | 0.0313 (12) | 0.0422 (13) | 0.0011 (10) | 0.0172 (11) | −0.0014 (10) |
C28 | 0.0384 (13) | 0.0325 (12) | 0.0370 (13) | 0.0011 (10) | 0.0164 (11) | −0.0003 (10) |
C29 | 0.0595 (18) | 0.0362 (14) | 0.0430 (15) | 0.0025 (12) | 0.0241 (14) | −0.0063 (11) |
C30 | 0.0563 (18) | 0.0449 (15) | 0.0381 (14) | 0.0016 (13) | 0.0165 (13) | −0.0072 (12) |
C31 | 0.0521 (17) | 0.0362 (14) | 0.0554 (17) | −0.0092 (13) | 0.0221 (14) | −0.0035 (12) |
C32 | 0.0464 (17) | 0.0559 (18) | 0.0590 (18) | −0.0170 (14) | 0.0190 (14) | −0.0069 (15) |
C33 | 0.0367 (13) | 0.0351 (13) | 0.0372 (13) | 0.0000 (10) | 0.0196 (11) | 0.0034 (10) |
C34 | 0.0373 (13) | 0.0320 (12) | 0.0354 (12) | 0.0033 (10) | 0.0169 (11) | 0.0027 (10) |
C35 | 0.0473 (15) | 0.0332 (13) | 0.0434 (14) | −0.0043 (12) | 0.0156 (12) | −0.0033 (11) |
C36 | 0.0593 (18) | 0.0310 (13) | 0.0532 (16) | −0.0021 (12) | 0.0268 (14) | −0.0084 (12) |
C37 | 0.0461 (16) | 0.0553 (17) | 0.0430 (15) | −0.0118 (14) | 0.0189 (13) | −0.0069 (13) |
C38 | 0.0354 (14) | 0.0413 (13) | 0.0439 (14) | −0.0071 (11) | 0.0148 (11) | 0.0007 (11) |
C39 | 0.0589 (19) | 0.0521 (17) | 0.0586 (18) | −0.0201 (15) | 0.0191 (15) | −0.0053 (14) |
C40 | 0.0549 (19) | 0.0560 (19) | 0.081 (2) | −0.0229 (15) | 0.0280 (18) | 0.0052 (17) |
C41 | 0.0488 (17) | 0.065 (2) | 0.064 (2) | −0.0038 (15) | 0.0303 (15) | 0.0170 (16) |
C42 | 0.0452 (16) | 0.0497 (16) | 0.0543 (16) | −0.0009 (13) | 0.0279 (13) | 0.0028 (13) |
C43 | 0.0325 (13) | 0.0346 (12) | 0.0426 (13) | −0.0002 (10) | 0.0173 (11) | 0.0039 (11) |
C44 | 0.0436 (15) | 0.0369 (14) | 0.0455 (15) | −0.0050 (11) | 0.0243 (13) | −0.0037 (11) |
C45 | 0.0352 (13) | 0.0355 (12) | 0.0392 (13) | −0.0034 (11) | 0.0174 (11) | 0.0021 (10) |
C46 | 0.0338 (13) | 0.0311 (12) | 0.0408 (13) | −0.0018 (10) | 0.0168 (11) | 0.0000 (10) |
C47 | 0.0458 (16) | 0.0385 (14) | 0.0524 (16) | 0.0079 (12) | 0.0199 (13) | 0.0074 (12) |
C48 | 0.0580 (19) | 0.0493 (17) | 0.071 (2) | 0.0162 (15) | 0.0305 (17) | −0.0028 (15) |
C49 | 0.064 (2) | 0.0582 (19) | 0.066 (2) | 0.0063 (16) | 0.0424 (17) | −0.0081 (16) |
C50 | 0.0539 (17) | 0.0488 (16) | 0.0495 (16) | −0.0011 (13) | 0.0303 (14) | 0.0008 (13) |
C51 | 0.0375 (13) | 0.0312 (12) | 0.0402 (13) | −0.0048 (10) | 0.0187 (11) | −0.0020 (10) |
C52 | 0.0443 (15) | 0.0344 (13) | 0.0517 (16) | −0.0002 (11) | 0.0281 (13) | 0.0096 (12) |
Ni1—N11 | 2.072 (2) | O2—C37 | 1.252 (3) |
Ni1—N5 | 2.090 (2) | O3—C44 | 1.255 (3) |
Ni1—N3 | 2.102 (2) | O4—C44 | 1.263 (3) |
Ni1—N9 | 2.119 (2) | O5—C45 | 1.255 (3) |
Ni1—N1 | 2.123 (2) | O6—C45 | 1.264 (3) |
Ni1—N7 | 2.137 (2) | O7—C52 | 1.269 (3) |
Ni2—N19 | 2.076 (2) | O8—C52 | 1.243 (3) |
Ni2—N21 | 2.088 (2) | C1—C2 | 1.364 (4) |
Ni2—N23 | 2.097 (2) | C1—H1 | 0.9300 |
Ni2—N13 | 2.098 (2) | C2—H2 | 0.9300 |
Ni2—N17 | 2.107 (2) | C3—C4 | 1.442 (4) |
Ni2—N15 | 2.124 (2) | C5—C6 | 1.349 (4) |
N1—C3 | 1.326 (3) | C5—H5 | 0.9300 |
N1—C1 | 1.365 (3) | C6—H6 | 0.9300 |
N2—C3 | 1.342 (3) | C7—C8 | 1.344 (4) |
N2—C2 | 1.357 (4) | C7—H7 | 0.9300 |
N2—H2A | 0.854 (18) | C8—H8 | 0.9300 |
N3—C4 | 1.325 (3) | C9—C10 | 1.441 (3) |
N3—C5 | 1.361 (3) | C11—C12 | 1.349 (4) |
N4—C4 | 1.341 (3) | C11—H11 | 0.9300 |
N4—C6 | 1.371 (4) | C12—H12 | 0.9300 |
N4—H4A | 0.875 (18) | C13—C14 | 1.351 (4) |
N5—C9 | 1.331 (3) | C13—H13 | 0.9300 |
N5—C7 | 1.371 (3) | C14—H14 | 0.9300 |
N6—C9 | 1.342 (3) | C15—C16 | 1.445 (4) |
N6—C8 | 1.375 (4) | C17—C18 | 1.352 (4) |
N6—H6A | 0.856 (18) | C17—H17 | 0.9300 |
N7—C10 | 1.324 (3) | C18—H18 | 0.9300 |
N7—C11 | 1.381 (3) | C19—C20 | 1.352 (5) |
N8—C10 | 1.338 (3) | C19—H19 | 0.9300 |
N8—C12 | 1.372 (3) | C20—H20 | 0.9300 |
N8—H8A | 0.856 (18) | C21—C22 | 1.448 (4) |
N9—C15 | 1.327 (3) | C23—C24 | 1.359 (4) |
N9—C13 | 1.366 (4) | C23—H23 | 0.9300 |
N10—C15 | 1.345 (3) | C24—H24 | 0.9300 |
N10—C14 | 1.369 (4) | C25—C26 | 1.379 (4) |
N10—H10A | 0.885 (18) | C25—H25 | 0.9300 |
N11—C16 | 1.317 (3) | C26—H26 | 0.9300 |
N11—C17 | 1.380 (3) | C27—C28 | 1.439 (3) |
N12—C16 | 1.344 (3) | C29—C30 | 1.361 (4) |
N12—C18 | 1.374 (4) | C29—H29 | 0.9300 |
N12—H12A | 0.843 (18) | C30—H30 | 0.9300 |
N13—C21 | 1.316 (3) | C31—C32 | 1.344 (4) |
N13—C19 | 1.375 (4) | C31—H31 | 0.9300 |
N14—C21 | 1.344 (3) | C32—H32 | 0.9300 |
N14—C20 | 1.363 (4) | C33—C34 | 1.447 (3) |
N14—H14A | 0.865 (18) | C35—C36 | 1.355 (4) |
N15—C22 | 1.325 (3) | C35—H35 | 0.9300 |
N15—C23 | 1.372 (3) | C36—H36 | 0.9300 |
N16—C22 | 1.333 (3) | C37—C38 | 1.506 (4) |
N16—C24 | 1.369 (4) | C38—C39 | 1.385 (4) |
N16—H16A | 0.845 (18) | C38—C43 | 1.385 (4) |
N17—C27 | 1.329 (3) | C39—C40 | 1.392 (5) |
N17—C25 | 1.372 (3) | C39—H39 | 0.9300 |
N18—C27 | 1.348 (3) | C40—C41 | 1.361 (5) |
N18—C26 | 1.372 (4) | C40—H40 | 0.9300 |
N18—H18A | 0.853 (18) | C41—C42 | 1.374 (4) |
N19—C28 | 1.331 (3) | C41—H41 | 0.9300 |
N19—C29 | 1.366 (3) | C42—C43 | 1.392 (3) |
N20—C28 | 1.340 (3) | C42—H42 | 0.9300 |
N20—C30 | 1.369 (3) | C43—C44 | 1.506 (3) |
N20—H20A | 0.872 (18) | C45—C46 | 1.513 (3) |
N21—C34 | 1.322 (3) | C46—C47 | 1.392 (3) |
N21—C35 | 1.375 (3) | C46—C51 | 1.403 (3) |
N22—C34 | 1.349 (3) | C47—C48 | 1.383 (4) |
N22—C36 | 1.362 (3) | C47—H47 | 0.9300 |
N22—H22A | 0.902 (18) | C48—C49 | 1.372 (4) |
N23—C33 | 1.321 (3) | C48—H48 | 0.9300 |
N23—C31 | 1.376 (3) | C49—C50 | 1.371 (4) |
N24—C33 | 1.343 (3) | C49—H49 | 0.9300 |
N24—C32 | 1.368 (4) | C50—C51 | 1.391 (4) |
N24—H24A | 0.841 (18) | C50—H50 | 0.9300 |
O1—C37 | 1.257 (3) | C51—C52 | 1.506 (3) |
N11—Ni1—N5 | 169.97 (8) | N7—C10—N8 | 112.3 (2) |
N11—Ni1—N3 | 88.58 (8) | N7—C10—C9 | 117.8 (2) |
N5—Ni1—N3 | 96.75 (8) | N8—C10—C9 | 129.7 (2) |
N11—Ni1—N9 | 78.90 (8) | C12—C11—N7 | 109.5 (2) |
N5—Ni1—N9 | 96.76 (8) | C12—C11—H11 | 125.3 |
N3—Ni1—N9 | 165.43 (8) | N7—C11—H11 | 125.3 |
N11—Ni1—N1 | 101.58 (8) | C11—C12—N8 | 107.0 (2) |
N5—Ni1—N1 | 87.79 (8) | C11—C12—H12 | 126.5 |
N3—Ni1—N1 | 79.31 (8) | N8—C12—H12 | 126.5 |
N9—Ni1—N1 | 95.82 (8) | C14—C13—N9 | 110.1 (3) |
N11—Ni1—N7 | 92.87 (8) | C14—C13—H13 | 124.9 |
N5—Ni1—N7 | 78.57 (8) | N9—C13—H13 | 124.9 |
N3—Ni1—N7 | 91.25 (8) | C13—C14—N10 | 106.3 (3) |
N9—Ni1—N7 | 96.73 (8) | C13—C14—H14 | 126.9 |
N1—Ni1—N7 | 162.44 (8) | N10—C14—H14 | 126.9 |
N19—Ni2—N21 | 92.13 (8) | N9—C15—N10 | 111.2 (2) |
N19—Ni2—N23 | 99.52 (8) | N9—C15—C16 | 118.0 (2) |
N21—Ni2—N23 | 79.07 (8) | N10—C15—C16 | 130.7 (2) |
N19—Ni2—N13 | 91.66 (9) | N11—C16—N12 | 111.8 (2) |
N21—Ni2—N13 | 94.35 (8) | N11—C16—C15 | 116.9 (2) |
N23—Ni2—N13 | 167.17 (8) | N12—C16—C15 | 131.1 (2) |
N19—Ni2—N17 | 79.57 (8) | C18—C17—N11 | 109.1 (2) |
N21—Ni2—N17 | 165.64 (8) | C18—C17—H17 | 125.5 |
N23—Ni2—N17 | 90.67 (8) | N11—C17—H17 | 125.5 |
N13—Ni2—N17 | 97.57 (8) | C17—C18—N12 | 106.9 (2) |
N19—Ni2—N15 | 166.75 (8) | C17—C18—H18 | 126.5 |
N21—Ni2—N15 | 98.11 (8) | N12—C18—H18 | 126.5 |
N23—Ni2—N15 | 90.70 (8) | C20—C19—N13 | 108.9 (3) |
N13—Ni2—N15 | 79.25 (8) | C20—C19—H19 | 125.6 |
N17—Ni2—N15 | 91.98 (8) | N13—C19—H19 | 125.6 |
C3—N1—C1 | 104.9 (2) | C19—C20—N14 | 107.3 (3) |
C3—N1—Ni1 | 111.36 (16) | C19—C20—H20 | 126.3 |
C1—N1—Ni1 | 142.47 (18) | N14—C20—H20 | 126.3 |
C3—N2—C2 | 106.7 (2) | N13—C21—N14 | 111.8 (2) |
C3—N2—H2A | 118 (2) | N13—C21—C22 | 118.2 (2) |
C2—N2—H2A | 134 (2) | N14—C21—C22 | 129.8 (3) |
C4—N3—C5 | 105.5 (2) | N15—C22—N16 | 112.2 (2) |
C4—N3—Ni1 | 112.54 (17) | N15—C22—C21 | 117.7 (2) |
C5—N3—Ni1 | 140.50 (17) | N16—C22—C21 | 130.1 (2) |
C4—N4—C6 | 106.5 (2) | C24—C23—N15 | 109.3 (3) |
C4—N4—H4A | 122 (2) | C24—C23—H23 | 125.3 |
C6—N4—H4A | 131 (2) | N15—C23—H23 | 125.3 |
C9—N5—C7 | 105.5 (2) | C23—C24—N16 | 106.7 (3) |
C9—N5—Ni1 | 113.58 (16) | C23—C24—H24 | 126.6 |
C7—N5—Ni1 | 140.87 (18) | N16—C24—H24 | 126.6 |
C9—N6—C8 | 106.4 (2) | N17—C25—C26 | 109.7 (2) |
C9—N6—H6A | 126 (3) | N17—C25—H25 | 125.2 |
C8—N6—H6A | 124 (3) | C26—C25—H25 | 125.2 |
C10—N7—C11 | 104.8 (2) | N18—C26—C25 | 105.8 (2) |
C10—N7—Ni1 | 112.14 (16) | N18—C26—H26 | 127.1 |
C11—N7—Ni1 | 141.64 (17) | C25—C26—H26 | 127.1 |
C10—N8—C12 | 106.4 (2) | N17—C27—N18 | 111.6 (2) |
C10—N8—H8A | 121 (2) | N17—C27—C28 | 117.9 (2) |
C12—N8—H8A | 132 (2) | N18—C27—C28 | 130.5 (2) |
C15—N9—C13 | 105.3 (2) | N19—C28—N20 | 111.0 (2) |
C15—N9—Ni1 | 111.65 (17) | N19—C28—C27 | 117.4 (2) |
C13—N9—Ni1 | 142.97 (19) | N20—C28—C27 | 131.5 (2) |
C15—N10—C14 | 107.0 (2) | C30—C29—N19 | 109.2 (2) |
C15—N10—H10A | 132 (2) | C30—C29—H29 | 125.4 |
C14—N10—H10A | 119 (2) | N19—C29—H29 | 125.4 |
C16—N11—C17 | 105.6 (2) | C29—C30—N20 | 106.5 (2) |
C16—N11—Ni1 | 114.01 (16) | C29—C30—H30 | 126.7 |
C17—N11—Ni1 | 140.20 (18) | N20—C30—H30 | 126.7 |
C16—N12—C18 | 106.5 (2) | C32—C31—N23 | 109.1 (3) |
C16—N12—H12A | 127 (3) | C32—C31—H31 | 125.5 |
C18—N12—H12A | 126 (3) | N23—C31—H31 | 125.5 |
C21—N13—C19 | 105.6 (2) | C31—C32—N24 | 107.3 (3) |
C21—N13—Ni2 | 112.52 (17) | C31—C32—H32 | 126.3 |
C19—N13—Ni2 | 141.29 (19) | N24—C32—H32 | 126.3 |
C21—N14—C20 | 106.4 (3) | N23—C33—N24 | 111.5 (2) |
C21—N14—H14A | 134 (2) | N23—C33—C34 | 116.7 (2) |
C20—N14—H14A | 118 (2) | N24—C33—C34 | 131.8 (2) |
C22—N15—C23 | 105.1 (2) | N21—C34—N22 | 111.2 (2) |
C22—N15—Ni2 | 111.15 (17) | N21—C34—C33 | 118.0 (2) |
C23—N15—Ni2 | 141.88 (19) | N22—C34—C33 | 130.8 (2) |
C22—N16—C24 | 106.7 (2) | C36—C35—N21 | 109.2 (2) |
C22—N16—H16A | 134 (3) | C36—C35—H35 | 125.4 |
C24—N16—H16A | 119 (3) | N21—C35—H35 | 125.4 |
C27—N17—C25 | 105.5 (2) | C35—C36—N22 | 106.9 (2) |
C27—N17—Ni2 | 111.72 (16) | C35—C36—H36 | 126.5 |
C25—N17—Ni2 | 141.86 (19) | N22—C36—H36 | 126.5 |
C27—N18—C26 | 107.4 (2) | O2—C37—O1 | 124.9 (3) |
C27—N18—H18A | 122 (3) | O2—C37—C38 | 118.2 (2) |
C26—N18—H18A | 131 (3) | O1—C37—C38 | 116.8 (2) |
C28—N19—C29 | 106.0 (2) | C39—C38—C43 | 119.2 (3) |
C28—N19—Ni2 | 113.04 (16) | C39—C38—C37 | 118.9 (3) |
C29—N19—Ni2 | 140.27 (18) | C43—C38—C37 | 121.9 (2) |
C28—N20—C30 | 107.3 (2) | C38—C39—C40 | 120.8 (3) |
C28—N20—H20A | 124 (2) | C38—C39—H39 | 119.6 |
C30—N20—H20A | 128 (2) | C40—C39—H39 | 119.6 |
C34—N21—C35 | 105.7 (2) | C41—C40—C39 | 119.6 (3) |
C34—N21—Ni2 | 112.60 (15) | C41—C40—H40 | 120.2 |
C35—N21—Ni2 | 141.61 (18) | C39—C40—H40 | 120.2 |
C34—N22—C36 | 107.0 (2) | C40—C41—C42 | 120.2 (3) |
C34—N22—H22A | 129 (2) | C40—C41—H41 | 119.9 |
C36—N22—H22A | 123 (2) | C42—C41—H41 | 119.9 |
C33—N23—C31 | 105.6 (2) | C41—C42—C43 | 120.8 (3) |
C33—N23—Ni2 | 112.66 (16) | C41—C42—H42 | 119.6 |
C31—N23—Ni2 | 139.66 (19) | C43—C42—H42 | 119.6 |
C33—N24—C32 | 106.5 (2) | C38—C43—C42 | 119.3 (2) |
C33—N24—H24A | 138 (3) | C38—C43—C44 | 124.4 (2) |
C32—N24—H24A | 116 (3) | C42—C43—C44 | 116.2 (2) |
C2—C1—N1 | 109.7 (2) | O3—C44—O4 | 124.2 (2) |
C2—C1—H1 | 125.2 | O3—C44—C43 | 118.5 (2) |
N1—C1—H1 | 125.2 | O4—C44—C43 | 117.1 (2) |
N2—C2—C1 | 106.6 (2) | O5—C45—O6 | 124.4 (2) |
N2—C2—H2 | 126.7 | O5—C45—C46 | 118.6 (2) |
C1—C2—H2 | 126.7 | O6—C45—C46 | 116.9 (2) |
N1—C3—N2 | 112.0 (2) | C47—C46—C51 | 118.3 (2) |
N1—C3—C4 | 118.4 (2) | C47—C46—C45 | 119.0 (2) |
N2—C3—C4 | 129.6 (2) | C51—C46—C45 | 122.6 (2) |
N3—C4—N4 | 111.5 (2) | C48—C47—C46 | 121.3 (3) |
N3—C4—C3 | 117.8 (2) | C48—C47—H47 | 119.4 |
N4—C4—C3 | 130.5 (2) | C46—C47—H47 | 119.4 |
C6—C5—N3 | 109.9 (2) | C49—C48—C47 | 120.1 (3) |
C6—C5—H5 | 125.1 | C49—C48—H48 | 120.0 |
N3—C5—H5 | 125.1 | C47—C48—H48 | 120.0 |
C5—C6—N4 | 106.6 (3) | C50—C49—C48 | 119.6 (3) |
C5—C6—H6 | 126.7 | C50—C49—H49 | 120.2 |
N4—C6—H6 | 126.7 | C48—C49—H49 | 120.2 |
C8—C7—N5 | 109.4 (2) | C49—C50—C51 | 121.6 (3) |
C8—C7—H7 | 125.3 | C49—C50—H50 | 119.2 |
N5—C7—H7 | 125.3 | C51—C50—H50 | 119.2 |
C7—C8—N6 | 107.3 (2) | C50—C51—C46 | 119.1 (2) |
C7—C8—H8 | 126.4 | C50—C51—C52 | 116.4 (2) |
N6—C8—H8 | 126.4 | C46—C51—C52 | 124.4 (2) |
N5—C9—N6 | 111.4 (2) | O8—C52—O7 | 125.0 (2) |
N5—C9—C10 | 117.6 (2) | O8—C52—C51 | 117.5 (2) |
N6—C9—C10 | 131.0 (2) | O7—C52—C51 | 117.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O8i | 0.85 (2) | 1.84 (2) | 2.693 (3) | 175 (4) |
N4—H4A···O7i | 0.88 (2) | 1.97 (2) | 2.832 (3) | 169 (3) |
N6—H6A···O5 | 0.86 (2) | 1.94 (2) | 2.788 (3) | 169 (4) |
N8—H8A···O6 | 0.86 (2) | 1.91 (2) | 2.745 (3) | 165 (3) |
N10—H10A···O2ii | 0.89 (2) | 2.40 (3) | 2.990 (3) | 124 (3) |
N10—H10A···O3ii | 0.89 (2) | 2.22 (2) | 3.028 (3) | 152 (3) |
N12—H12A···O4ii | 0.84 (2) | 1.96 (2) | 2.792 (3) | 169 (4) |
N14—H14A···O1 | 0.87 (2) | 1.84 (2) | 2.674 (3) | 161 (4) |
N16—H16A···O2 | 0.85 (2) | 1.94 (2) | 2.723 (3) | 154 (4) |
N18—H18A···O4iii | 0.85 (2) | 1.94 (2) | 2.781 (3) | 169 (4) |
N20—H20A···O3iii | 0.87 (2) | 1.86 (2) | 2.728 (3) | 175 (3) |
N22—H22A···O7 | 0.90 (2) | 1.84 (2) | 2.733 (3) | 174 (3) |
N24—H24A···O6iv | 0.84 (2) | 1.99 (2) | 2.788 (3) | 158 (4) |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y−1, z; (iii) x, −y+5/2, z−1/2; (iv) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C6H6N4)3](C8H4O4) |
Mr | 625.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 23.5242 (18), 11.1168 (9), 23.8578 (19) |
β (°) | 115.325 (1) |
V (Å3) | 5639.5 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.74 |
Crystal size (mm) | 0.49 × 0.19 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2000) |
Tmin, Tmax | 0.712, 0.897 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 34502, 13575, 9366 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.666 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.146, 1.05 |
No. of reflections | 13575 |
No. of parameters | 811 |
No. of restraints | 12 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.85, −0.41 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 2000), SHELXL97 (Sheldrick, 2000), SHELXTL/PC (Sheldrick, 1999), SHELXTL/PC.
Ni1—N11 | 2.072 (2) | Ni2—N19 | 2.076 (2) |
Ni1—N5 | 2.090 (2) | Ni2—N21 | 2.088 (2) |
Ni1—N3 | 2.102 (2) | Ni2—N23 | 2.097 (2) |
Ni1—N9 | 2.119 (2) | Ni2—N13 | 2.098 (2) |
Ni1—N1 | 2.123 (2) | Ni2—N17 | 2.107 (2) |
Ni1—N7 | 2.137 (2) | Ni2—N15 | 2.124 (2) |
N11—Ni1—N5 | 169.97 (8) | N19—Ni2—N21 | 92.13 (8) |
N11—Ni1—N3 | 88.58 (8) | N19—Ni2—N23 | 99.52 (8) |
N5—Ni1—N3 | 96.75 (8) | N21—Ni2—N23 | 79.07 (8) |
N11—Ni1—N9 | 78.90 (8) | N19—Ni2—N13 | 91.66 (9) |
N5—Ni1—N9 | 96.76 (8) | N21—Ni2—N13 | 94.35 (8) |
N3—Ni1—N9 | 165.43 (8) | N23—Ni2—N13 | 167.17 (8) |
N11—Ni1—N1 | 101.58 (8) | N19—Ni2—N17 | 79.57 (8) |
N5—Ni1—N1 | 87.79 (8) | N21—Ni2—N17 | 165.64 (8) |
N3—Ni1—N1 | 79.31 (8) | N23—Ni2—N17 | 90.67 (8) |
N9—Ni1—N1 | 95.82 (8) | N13—Ni2—N17 | 97.57 (8) |
N11—Ni1—N7 | 92.87 (8) | N19—Ni2—N15 | 166.75 (8) |
N5—Ni1—N7 | 78.57 (8) | N21—Ni2—N15 | 98.11 (8) |
N3—Ni1—N7 | 91.25 (8) | N23—Ni2—N15 | 90.70 (8) |
N9—Ni1—N7 | 96.73 (8) | N13—Ni2—N15 | 79.25 (8) |
N1—Ni1—N7 | 162.44 (8) | N17—Ni2—N15 | 91.98 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O8i | 0.854 (18) | 1.842 (19) | 2.693 (3) | 175 (4) |
N4—H4A···O7i | 0.875 (18) | 1.968 (19) | 2.832 (3) | 169 (3) |
N6—H6A···O5 | 0.856 (18) | 1.94 (2) | 2.788 (3) | 169 (4) |
N8—H8A···O6 | 0.856 (18) | 1.91 (2) | 2.745 (3) | 165 (3) |
N10—H10A···O2ii | 0.885 (18) | 2.40 (3) | 2.990 (3) | 124 (3) |
N10—H10A···O3ii | 0.885 (18) | 2.22 (2) | 3.028 (3) | 152 (3) |
N12—H12A···O4ii | 0.843 (18) | 1.960 (19) | 2.792 (3) | 169 (4) |
N14—H14A···O1 | 0.865 (18) | 1.84 (2) | 2.674 (3) | 161 (4) |
N16—H16A···O2 | 0.845 (18) | 1.94 (2) | 2.723 (3) | 154 (4) |
N18—H18A···O4iii | 0.853 (18) | 1.94 (2) | 2.781 (3) | 169 (4) |
N20—H20A···O3iii | 0.872 (18) | 1.858 (19) | 2.728 (3) | 175 (3) |
N22—H22A···O7 | 0.902 (18) | 1.835 (19) | 2.733 (3) | 174 (3) |
N24—H24A···O6iv | 0.841 (18) | 1.99 (2) | 2.788 (3) | 158 (4) |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y−1, z; (iii) x, −y+5/2, z−1/2; (iv) −x+1, y+1/2, −z+1/2. |
In recent years, the controlled assembly of molecular building blocks to give three-dimensional nets connected via coordinative, hydrogen or covalent bonds, has been an important area for the development of molecular-based materials science (Ferey, 2001; Moulton & Zaworotko, 2002). 2,2'-Biimidazole (H2biim) possesses dual properties, namely coordination to metal centres and theability to act as a donor in hydrogen-bonding interactions (Fortin & Beauchamp, 2001; Sang et al., 2002; Atencio et al., 2004).
The structure of the title compound, (I), consists of [Ni(H2biim)3]2+ cations hydrogen bonded to phthalate dianions (Fig. 1). There are two molecules in the asymmetric unit. The coordination geometry of the nickel(II) centre can be described as distorted octahedral, formed by six N atoms from three chelating H2biim ligands. The main distortion results from the small N—Ni—N bite angles of the H2biim ligands, viz. 78.57 (8)–79.31 (8)° for [Ni1(H2biim)3]2+ and 79.07 (8)–79.57 (8)° for [Ni2(H2biim)3]2+ (Table 1). The Ni—N bond lengths are in the range 2.072 (2)–2.137 (2) Å. A similarly distorted octahedron has been reported previously for the analogous complex [NiII(Hbiim)3](NMe4) (NMe4 is tetramethylammonium), in which the Ni—N bond lengths are in the range of 1.96 (3)–2.19 (2) Å (Tadokoro et al., 1999).
Each [Ni1(H2bim)3]2+ complex cation is connected to three phthalate dianions through seven N—H···O hydrogen bonds, with N—O distances of 2.693 (3)–3.028 (3) Å (Table 2). In the hydrogen-bond environment of Ni2, however, each [Ni2(H2biim)3]2+ complex cation is connected through six strong N—H···O hydrogen bonds, with N—O distances of 2.674 (3)–2.788 (3) Å, to four phthalate dianions (Fig. 2). Through this complicated and dense three-dimensional network of hydrogen bonds, the crystal packing is formed (Fig. 3).