In the title mononuclear [Ni(phen)
3]sq·8H
2O complex [phen is 1,10-phenanthroline (C
12H
8N
2) and sq is squarate (C
4O
42−)], the Ni
II ion has a distorted octahedral coordination geometry composed of six N atoms from three bidentate chelating phen ligands. An extensive three-dimensional network of O
water—H
O, O
water—H
O
water and C—H
O hydrogen-bonding interactions is responsible for crystal stabilization.
Supporting information
CCDC reference: 271844
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.083
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor O12 - H12A ... ?
Alert level C
PLAT417_ALERT_2_C Short Inter D-H..H-D H8B .. H11A .. 2.11 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
[Ni(C12H8N2)3]·C4O4·8H2O | F(000) = 1784 |
Mr = 855.47 | Dx = 1.437 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 12345 reflections |
a = 10.9746 (4) Å | θ = 1.5–27.2° |
b = 21.4090 (11) Å | µ = 0.56 mm−1 |
c = 17.0115 (6) Å | T = 297 K |
β = 98.468 (3)° | Prism, red |
V = 3953.4 (3) Å3 | 0.3 × 0.2 × 0.1 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II diffractometer | 8678 independent reflections |
Radiation source: fine-focus sealed tube | 5074 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.1°, θmin = 1.5° |
ω scans | h = −13→14 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −27→27 |
Tmin = 0.737, Tmax = 0.900 | l = −21→21 |
56939 measured reflections | |
Refinement top
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.84 | w = 1/[σ2(Fo2) + (0.0443P)2] where P = (Fo2 + 2Fc2)/3 |
8678 reflections | (Δ/σ)max = 0.001 |
580 parameters | Δρmax = 0.22 e Å−3 |
24 restraints | Δρmin = −0.33 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.5881 (2) | 0.21726 (11) | 0.15459 (12) | 0.0502 (6) | |
H1 | 0.6384 | 0.2462 | 0.1845 | 0.060* | |
C2 | 0.6063 (2) | 0.20604 (14) | 0.07632 (14) | 0.0654 (7) | |
H2 | 0.6675 | 0.2271 | 0.0544 | 0.078* | |
C3 | 0.5329 (3) | 0.16372 (14) | 0.03292 (14) | 0.0703 (8) | |
H3 | 0.5446 | 0.1554 | −0.0191 | 0.084* | |
C4 | 0.4395 (2) | 0.13240 (12) | 0.06521 (12) | 0.0558 (6) | |
C5 | 0.3553 (3) | 0.08855 (13) | 0.02303 (15) | 0.0714 (8) | |
H5 | 0.3624 | 0.0789 | −0.0294 | 0.086* | |
C6 | 0.2668 (3) | 0.06115 (12) | 0.05717 (15) | 0.0660 (7) | |
H6 | 0.2128 | 0.0334 | 0.0279 | 0.079* | |
C7 | 0.2542 (2) | 0.07405 (10) | 0.13785 (13) | 0.0485 (5) | |
C8 | 0.1649 (2) | 0.04676 (10) | 0.17763 (17) | 0.0606 (7) | |
H8 | 0.1087 | 0.0186 | 0.1512 | 0.073* | |
C9 | 0.1602 (2) | 0.06128 (11) | 0.25467 (17) | 0.0626 (7) | |
H9 | 0.1007 | 0.0433 | 0.2813 | 0.075* | |
C10 | 0.2446 (2) | 0.10312 (10) | 0.29332 (14) | 0.0527 (6) | |
H10 | 0.2403 | 0.1127 | 0.3461 | 0.063* | |
C11 | 0.33598 (19) | 0.11602 (9) | 0.18134 (11) | 0.0402 (5) | |
C12 | 0.4283 (2) | 0.14651 (9) | 0.14409 (11) | 0.0408 (5) | |
C13 | 0.6767 (2) | 0.10070 (10) | 0.31639 (13) | 0.0488 (5) | |
H13 | 0.6857 | 0.1119 | 0.2647 | 0.059* | |
C14 | 0.7547 (2) | 0.05540 (11) | 0.35455 (15) | 0.0591 (6) | |
H14 | 0.8146 | 0.0369 | 0.3287 | 0.071* | |
C15 | 0.7426 (2) | 0.03837 (12) | 0.43006 (16) | 0.0669 (7) | |
H15 | 0.7935 | 0.0078 | 0.4561 | 0.080* | |
C16 | 0.6527 (2) | 0.06729 (11) | 0.46858 (14) | 0.0588 (6) | |
C17 | 0.6342 (3) | 0.05385 (15) | 0.54884 (16) | 0.0847 (9) | |
H17 | 0.6837 | 0.0243 | 0.5782 | 0.102* | |
C18 | 0.5468 (3) | 0.08329 (16) | 0.58191 (16) | 0.0868 (10) | |
H18 | 0.5362 | 0.0732 | 0.6337 | 0.104* | |
C19 | 0.4692 (2) | 0.12974 (12) | 0.54003 (13) | 0.0601 (7) | |
C20 | 0.3757 (3) | 0.16180 (14) | 0.57098 (15) | 0.0718 (8) | |
H20 | 0.3602 | 0.1530 | 0.6221 | 0.086* | |
C21 | 0.3079 (2) | 0.20554 (13) | 0.52703 (14) | 0.0631 (7) | |
H21 | 0.2455 | 0.2267 | 0.5475 | 0.076* | |
C22 | 0.3325 (2) | 0.21849 (11) | 0.45107 (12) | 0.0507 (6) | |
H22 | 0.2864 | 0.2492 | 0.4215 | 0.061* | |
C23 | 0.4870 (2) | 0.14473 (10) | 0.46250 (12) | 0.0447 (5) | |
C24 | 0.57914 (19) | 0.11272 (10) | 0.42619 (11) | 0.0433 (5) | |
C25 | 0.6998 (2) | 0.27055 (11) | 0.36242 (12) | 0.0475 (5) | |
H25 | 0.7393 | 0.2322 | 0.3711 | 0.057* | |
C26 | 0.7679 (2) | 0.32488 (12) | 0.38145 (14) | 0.0562 (6) | |
H26 | 0.8508 | 0.3225 | 0.4027 | 0.067* | |
C27 | 0.7125 (2) | 0.38095 (11) | 0.36881 (13) | 0.0531 (6) | |
H27 | 0.7575 | 0.4174 | 0.3811 | 0.064* | |
C28 | 0.5867 (2) | 0.38447 (10) | 0.33697 (12) | 0.0439 (5) | |
C29 | 0.5189 (3) | 0.44140 (10) | 0.32418 (14) | 0.0536 (6) | |
H29 | 0.5594 | 0.4792 | 0.3353 | 0.064* | |
C30 | 0.3977 (3) | 0.44142 (10) | 0.29637 (13) | 0.0526 (6) | |
H30 | 0.3551 | 0.4791 | 0.2902 | 0.063* | |
C31 | 0.3337 (2) | 0.38424 (10) | 0.27613 (11) | 0.0425 (5) | |
C32 | 0.2088 (2) | 0.38178 (11) | 0.24290 (13) | 0.0513 (6) | |
H32 | 0.1629 | 0.4183 | 0.2339 | 0.062* | |
C33 | 0.1563 (2) | 0.32523 (11) | 0.22415 (14) | 0.0538 (6) | |
H33 | 0.0743 | 0.3229 | 0.2007 | 0.065* | |
C34 | 0.2245 (2) | 0.27110 (11) | 0.23998 (12) | 0.0471 (5) | |
H34 | 0.1859 | 0.2329 | 0.2278 | 0.057* | |
C35 | 0.39695 (19) | 0.32754 (9) | 0.28862 (10) | 0.0357 (4) | |
C36 | 0.52564 (19) | 0.32758 (9) | 0.31994 (11) | 0.0363 (4) | |
C37 | 0.8661 (2) | 0.08538 (11) | 0.13652 (13) | 0.0533 (6) | |
C38 | 0.9180 (2) | 0.09563 (10) | 0.06308 (12) | 0.0458 (5) | |
C39 | 0.9540 (2) | 0.15819 (11) | 0.09021 (13) | 0.0540 (6) | |
C40 | 0.8988 (2) | 0.14867 (11) | 0.16111 (13) | 0.0543 (6) | |
N1 | 0.50204 (15) | 0.18838 (8) | 0.18805 (9) | 0.0404 (4) | |
N2 | 0.33129 (16) | 0.13012 (8) | 0.25851 (10) | 0.0413 (4) | |
N3 | 0.59000 (16) | 0.12873 (8) | 0.35023 (9) | 0.0402 (4) | |
N4 | 0.41900 (15) | 0.18902 (8) | 0.41888 (9) | 0.0414 (4) | |
N5 | 0.58151 (15) | 0.27120 (8) | 0.33263 (9) | 0.0386 (4) | |
N6 | 0.34213 (15) | 0.27118 (7) | 0.27163 (9) | 0.0381 (4) | |
O1 | 0.8192 (2) | 0.03948 (9) | 0.16604 (12) | 0.0806 (6) | |
O2 | 0.92778 (16) | 0.06252 (7) | 0.00404 (9) | 0.0586 (4) | |
O3 | 1.0132 (2) | 0.20205 (8) | 0.06372 (11) | 0.0852 (6) | |
O4 | 0.8860 (2) | 0.18207 (8) | 0.22058 (10) | 0.0794 (6) | |
O5 | 0.0043 (3) | 0.18654 (10) | 0.37284 (14) | 0.1155 (9) | |
H5A | 0.036 (4) | 0.2221 (10) | 0.380 (2) | 0.173* | |
H5B | −0.032 (4) | 0.1844 (19) | 0.3259 (11) | 0.173* | |
O6 | 0.0814 (3) | 0.08112 (12) | 0.46285 (14) | 0.1087 (8) | |
H6A | 0.042 (4) | 0.1135 (11) | 0.445 (2) | 0.163* | |
H6B | 0.048 (4) | 0.0512 (12) | 0.435 (2) | 0.163* | |
O7 | 0.9906 (2) | 0.03432 (10) | 0.60240 (13) | 0.0889 (6) | |
H7A | 1.002 (4) | 0.0635 (12) | 0.5709 (17) | 0.133* | |
H7B | 0.950 (3) | 0.0508 (15) | 0.6353 (16) | 0.133* | |
O8 | 0.8995 (2) | 0.41842 (8) | 0.23219 (11) | 0.0757 (5) | |
H8A | 0.938 (3) | 0.4158 (14) | 0.2793 (9) | 0.114* | |
H8B | 0.871 (3) | 0.3817 (8) | 0.2200 (17) | 0.114* | |
O9 | 0.05824 (19) | 0.43216 (8) | 0.37907 (10) | 0.0634 (5) | |
H9A | 0.103 (2) | 0.4629 (10) | 0.3743 (17) | 0.095* | |
H9B | 0.022 (2) | 0.4366 (13) | 0.4191 (12) | 0.095* | |
O10 | 0.09807 (19) | 0.30435 (8) | 0.42179 (11) | 0.0713 (5) | |
H10A | 0.099 (3) | 0.3410 (7) | 0.4042 (16) | 0.107* | |
H10B | 0.078 (3) | 0.3056 (13) | 0.4677 (10) | 0.107* | |
O11 | 0.8248 (2) | 0.30352 (10) | 0.18068 (13) | 0.0864 (6) | |
H11A | 0.836 (4) | 0.3108 (15) | 0.1335 (10) | 0.130* | |
H11B | 0.859 (3) | 0.2687 (10) | 0.1948 (18) | 0.130* | |
O12 | 0.8715 (3) | 0.30722 (13) | 0.02349 (19) | 0.1307 (10) | |
H12A | 0.933 (3) | 0.3329 (15) | 0.031 (3) | 0.196* | |
H12B | 0.906 (4) | 0.2712 (9) | 0.032 (3) | 0.196* | |
Ni1 | 0.46223 (3) | 0.196308 (11) | 0.303534 (15) | 0.03560 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0443 (13) | 0.0654 (15) | 0.0427 (12) | −0.0047 (11) | 0.0126 (10) | 0.0053 (10) |
C2 | 0.0618 (17) | 0.093 (2) | 0.0456 (13) | 0.0005 (15) | 0.0218 (12) | 0.0104 (13) |
C3 | 0.083 (2) | 0.096 (2) | 0.0342 (12) | 0.0093 (17) | 0.0170 (13) | 0.0021 (13) |
C4 | 0.0653 (17) | 0.0654 (16) | 0.0349 (11) | 0.0083 (13) | 0.0014 (11) | −0.0011 (10) |
C5 | 0.091 (2) | 0.0783 (19) | 0.0400 (13) | 0.0042 (17) | −0.0066 (14) | −0.0138 (13) |
C6 | 0.077 (2) | 0.0574 (15) | 0.0551 (15) | 0.0021 (14) | −0.0186 (14) | −0.0103 (12) |
C7 | 0.0477 (14) | 0.0379 (12) | 0.0545 (13) | 0.0062 (10) | −0.0100 (11) | −0.0033 (10) |
C8 | 0.0472 (15) | 0.0398 (13) | 0.0893 (19) | −0.0046 (11) | −0.0079 (14) | −0.0023 (12) |
C9 | 0.0522 (16) | 0.0490 (14) | 0.0878 (19) | −0.0113 (12) | 0.0151 (14) | 0.0028 (13) |
C10 | 0.0503 (14) | 0.0472 (13) | 0.0639 (14) | −0.0108 (11) | 0.0191 (12) | −0.0013 (11) |
C11 | 0.0386 (12) | 0.0367 (11) | 0.0429 (11) | 0.0047 (9) | −0.0021 (9) | 0.0000 (9) |
C12 | 0.0439 (13) | 0.0438 (12) | 0.0333 (10) | 0.0054 (9) | 0.0006 (9) | −0.0011 (8) |
C13 | 0.0466 (14) | 0.0497 (13) | 0.0513 (12) | 0.0069 (11) | 0.0115 (11) | −0.0044 (10) |
C14 | 0.0529 (16) | 0.0571 (15) | 0.0672 (16) | 0.0167 (12) | 0.0084 (13) | −0.0060 (12) |
C15 | 0.0614 (17) | 0.0622 (16) | 0.0743 (18) | 0.0210 (13) | 0.0011 (14) | 0.0115 (13) |
C16 | 0.0598 (16) | 0.0605 (15) | 0.0545 (14) | 0.0113 (12) | 0.0029 (12) | 0.0122 (11) |
C17 | 0.095 (2) | 0.098 (2) | 0.0592 (16) | 0.0280 (19) | 0.0049 (16) | 0.0332 (15) |
C18 | 0.099 (2) | 0.115 (3) | 0.0493 (15) | 0.023 (2) | 0.0213 (16) | 0.0306 (16) |
C19 | 0.0668 (18) | 0.0771 (17) | 0.0378 (12) | 0.0039 (14) | 0.0125 (12) | 0.0078 (11) |
C20 | 0.077 (2) | 0.102 (2) | 0.0418 (13) | 0.0006 (17) | 0.0272 (13) | 0.0021 (14) |
C21 | 0.0599 (16) | 0.0854 (19) | 0.0489 (13) | 0.0056 (15) | 0.0239 (12) | −0.0082 (13) |
C22 | 0.0468 (14) | 0.0612 (14) | 0.0468 (12) | 0.0029 (11) | 0.0159 (11) | −0.0084 (10) |
C23 | 0.0466 (13) | 0.0516 (13) | 0.0363 (10) | −0.0015 (10) | 0.0074 (10) | 0.0011 (9) |
C24 | 0.0431 (13) | 0.0465 (12) | 0.0400 (11) | 0.0006 (10) | 0.0054 (9) | 0.0022 (9) |
C25 | 0.0385 (13) | 0.0530 (14) | 0.0491 (12) | −0.0010 (11) | 0.0005 (10) | −0.0041 (10) |
C26 | 0.0362 (13) | 0.0689 (17) | 0.0612 (15) | −0.0096 (12) | −0.0008 (11) | −0.0043 (12) |
C27 | 0.0481 (15) | 0.0544 (14) | 0.0560 (13) | −0.0149 (12) | 0.0047 (11) | −0.0042 (11) |
C28 | 0.0484 (14) | 0.0459 (12) | 0.0380 (11) | −0.0066 (10) | 0.0078 (10) | −0.0009 (9) |
C29 | 0.0661 (17) | 0.0374 (12) | 0.0574 (13) | −0.0059 (12) | 0.0089 (12) | −0.0006 (10) |
C30 | 0.0637 (17) | 0.0391 (12) | 0.0558 (13) | 0.0048 (11) | 0.0111 (12) | 0.0005 (10) |
C31 | 0.0473 (13) | 0.0443 (12) | 0.0375 (10) | 0.0059 (10) | 0.0114 (9) | 0.0052 (9) |
C32 | 0.0477 (14) | 0.0543 (14) | 0.0533 (13) | 0.0137 (11) | 0.0120 (11) | 0.0052 (11) |
C33 | 0.0350 (13) | 0.0677 (16) | 0.0582 (14) | 0.0056 (11) | 0.0049 (11) | 0.0037 (11) |
C34 | 0.0334 (13) | 0.0534 (14) | 0.0545 (13) | −0.0005 (10) | 0.0061 (10) | −0.0004 (10) |
C35 | 0.0376 (12) | 0.0413 (11) | 0.0293 (9) | 0.0011 (9) | 0.0088 (8) | −0.0003 (8) |
C36 | 0.0379 (12) | 0.0408 (11) | 0.0306 (9) | −0.0040 (9) | 0.0062 (9) | −0.0018 (8) |
C37 | 0.0534 (15) | 0.0528 (14) | 0.0555 (13) | 0.0052 (11) | 0.0136 (11) | 0.0046 (11) |
C38 | 0.0433 (13) | 0.0479 (12) | 0.0460 (12) | 0.0046 (10) | 0.0054 (10) | 0.0047 (10) |
C39 | 0.0617 (16) | 0.0473 (13) | 0.0529 (13) | 0.0002 (11) | 0.0083 (11) | 0.0020 (10) |
C40 | 0.0615 (16) | 0.0545 (14) | 0.0460 (12) | 0.0086 (11) | 0.0054 (11) | 0.0000 (10) |
N1 | 0.0383 (10) | 0.0465 (10) | 0.0370 (8) | 0.0002 (8) | 0.0078 (8) | 0.0007 (7) |
N2 | 0.0415 (10) | 0.0395 (9) | 0.0434 (10) | −0.0028 (8) | 0.0078 (8) | −0.0024 (7) |
N3 | 0.0404 (10) | 0.0415 (10) | 0.0397 (9) | 0.0017 (8) | 0.0091 (8) | −0.0009 (7) |
N4 | 0.0415 (10) | 0.0462 (10) | 0.0374 (8) | 0.0013 (8) | 0.0089 (8) | −0.0038 (8) |
N5 | 0.0350 (10) | 0.0436 (10) | 0.0366 (9) | 0.0004 (8) | 0.0033 (8) | −0.0009 (7) |
N6 | 0.0330 (10) | 0.0433 (10) | 0.0380 (9) | −0.0036 (8) | 0.0057 (7) | −0.0018 (7) |
O1 | 0.1002 (15) | 0.0651 (12) | 0.0864 (13) | −0.0117 (11) | 0.0467 (12) | 0.0061 (10) |
O2 | 0.0671 (11) | 0.0540 (9) | 0.0563 (9) | 0.0012 (8) | 0.0137 (8) | −0.0057 (8) |
O3 | 0.1202 (17) | 0.0539 (11) | 0.0898 (13) | −0.0233 (11) | 0.0429 (12) | −0.0020 (10) |
O4 | 0.1145 (17) | 0.0723 (12) | 0.0529 (10) | 0.0102 (11) | 0.0171 (10) | −0.0114 (9) |
O5 | 0.185 (3) | 0.0624 (14) | 0.0830 (15) | 0.0051 (15) | −0.0330 (16) | −0.0019 (11) |
O6 | 0.142 (2) | 0.0864 (16) | 0.0905 (16) | −0.0172 (16) | −0.0074 (15) | 0.0095 (13) |
O7 | 0.1102 (18) | 0.0774 (14) | 0.0823 (15) | 0.0133 (13) | 0.0250 (13) | −0.0033 (11) |
O8 | 0.1043 (17) | 0.0526 (11) | 0.0711 (12) | −0.0043 (11) | 0.0163 (11) | −0.0017 (9) |
O9 | 0.0831 (14) | 0.0555 (11) | 0.0532 (10) | 0.0105 (9) | 0.0156 (9) | −0.0017 (8) |
O10 | 0.0784 (13) | 0.0561 (10) | 0.0829 (13) | 0.0130 (10) | 0.0237 (11) | −0.0040 (10) |
O11 | 0.0948 (16) | 0.0679 (13) | 0.0988 (15) | −0.0213 (12) | 0.0220 (13) | −0.0141 (12) |
O12 | 0.176 (3) | 0.108 (2) | 0.115 (2) | 0.0107 (19) | 0.043 (2) | 0.0098 (19) |
Ni1 | 0.03541 (14) | 0.03821 (13) | 0.03380 (12) | −0.00090 (13) | 0.00717 (9) | −0.00187 (12) |
Geometric parameters (Å, º) top
C1—N1 | 1.325 (3) | C26—C27 | 1.348 (3) |
C1—C2 | 1.396 (3) | C26—H26 | 0.93 |
C1—H1 | 0.93 | C27—C28 | 1.409 (3) |
C2—C3 | 1.357 (4) | C27—H27 | 0.93 |
C2—H2 | 0.93 | C28—C36 | 1.400 (3) |
C3—C4 | 1.402 (4) | C28—C29 | 1.428 (3) |
C3—H3 | 0.93 | C29—C30 | 1.344 (3) |
C4—C12 | 1.399 (3) | C29—H29 | 0.93 |
C4—C5 | 1.433 (4) | C30—C31 | 1.428 (3) |
C5—C6 | 1.339 (4) | C30—H30 | 0.93 |
C5—H5 | 0.93 | C31—C35 | 1.399 (3) |
C6—C7 | 1.426 (3) | C31—C32 | 1.404 (3) |
C6—H6 | 0.93 | C32—C33 | 1.359 (3) |
C7—C8 | 1.398 (3) | C32—H32 | 0.93 |
C7—C11 | 1.402 (3) | C33—C34 | 1.385 (3) |
C8—C9 | 1.355 (4) | C33—H33 | 0.93 |
C8—H8 | 0.93 | C34—N6 | 1.323 (3) |
C9—C10 | 1.383 (3) | C34—H34 | 0.93 |
C9—H9 | 0.93 | C35—N6 | 1.360 (2) |
C10—N2 | 1.325 (3) | C35—C36 | 1.434 (3) |
C10—H10 | 0.93 | C36—N5 | 1.357 (2) |
C11—N2 | 1.355 (2) | C37—O1 | 1.249 (3) |
C11—C12 | 1.429 (3) | C37—C40 | 1.448 (3) |
C12—N1 | 1.356 (2) | C37—C38 | 1.464 (3) |
C13—N3 | 1.326 (3) | C38—O2 | 1.247 (2) |
C13—C14 | 1.390 (3) | C38—C39 | 1.452 (3) |
C13—H13 | 0.93 | C39—O3 | 1.263 (3) |
C14—C15 | 1.361 (3) | C39—C40 | 1.441 (3) |
C14—H14 | 0.93 | C40—O4 | 1.263 (3) |
C15—C16 | 1.406 (4) | N1—Ni1 | 2.0814 (15) |
C15—H15 | 0.93 | N2—Ni1 | 2.0823 (17) |
C16—C24 | 1.395 (3) | N3—Ni1 | 2.0886 (17) |
C16—C17 | 1.439 (4) | N4—Ni1 | 2.0913 (16) |
C17—C18 | 1.339 (4) | N5—Ni1 | 2.0829 (16) |
C17—H17 | 0.93 | N6—Ni1 | 2.0954 (17) |
C18—C19 | 1.429 (4) | O5—H5A | 0.84 (3) |
C18—H18 | 0.93 | O5—H5B | 0.84 (3) |
C19—C23 | 1.399 (3) | O6—H6A | 0.85 (3) |
C19—C20 | 1.400 (4) | O6—H6B | 0.85 (3) |
C20—C21 | 1.351 (4) | O7—H7A | 0.84 (3) |
C20—H20 | 0.93 | O7—H7B | 0.84 (3) |
C21—C22 | 1.387 (3) | O8—H8A | 0.85 (2) |
C21—H21 | 0.93 | O8—H8B | 0.86 (2) |
C22—N4 | 1.324 (3) | O9—H9A | 0.83 (2) |
C22—H22 | 0.93 | O9—H9B | 0.84 (2) |
C23—N4 | 1.358 (3) | O10—H10A | 0.84 (2) |
C23—C24 | 1.434 (3) | O10—H10B | 0.84 (2) |
C24—N3 | 1.359 (2) | O11—H11A | 0.84 (2) |
C25—N5 | 1.322 (3) | O11—H11B | 0.85 (2) |
C25—C26 | 1.394 (3) | O12—H12A | 0.87 (3) |
C25—H25 | 0.93 | O12—H12B | 0.86 (3) |
| | | |
N1—C1—C2 | 122.7 (2) | C36—C28—C27 | 116.4 (2) |
N1—C1—H1 | 118.6 | C36—C28—C29 | 119.2 (2) |
C2—C1—H1 | 118.6 | C27—C28—C29 | 124.3 (2) |
C3—C2—C1 | 118.5 (2) | C30—C29—C28 | 121.4 (2) |
C3—C2—H2 | 120.8 | C30—C29—H29 | 119.3 |
C1—C2—H2 | 120.8 | C28—C29—H29 | 119.3 |
C2—C3—C4 | 121.1 (2) | C29—C30—C31 | 120.7 (2) |
C2—C3—H3 | 119.5 | C29—C30—H30 | 119.6 |
C4—C3—H3 | 119.5 | C31—C30—H30 | 119.6 |
C12—C4—C3 | 116.5 (2) | C35—C31—C32 | 117.5 (2) |
C12—C4—C5 | 118.7 (2) | C35—C31—C30 | 119.4 (2) |
C3—C4—C5 | 124.8 (2) | C32—C31—C30 | 123.1 (2) |
C6—C5—C4 | 121.7 (2) | C33—C32—C31 | 118.9 (2) |
C6—C5—H5 | 119.1 | C33—C32—H32 | 120.5 |
C4—C5—H5 | 119.1 | C31—C32—H32 | 120.5 |
C5—C6—C7 | 120.8 (2) | C32—C33—C34 | 120.1 (2) |
C5—C6—H6 | 119.6 | C32—C33—H33 | 120.0 |
C7—C6—H6 | 119.6 | C34—C33—H33 | 120.0 |
C8—C7—C11 | 116.9 (2) | N6—C34—C33 | 123.0 (2) |
C8—C7—C6 | 124.0 (2) | N6—C34—H34 | 118.5 |
C11—C7—C6 | 119.1 (2) | C33—C34—H34 | 118.5 |
C9—C8—C7 | 120.1 (2) | N6—C35—C31 | 122.90 (18) |
C9—C8—H8 | 119.9 | N6—C35—C36 | 117.38 (18) |
C7—C8—H8 | 119.9 | C31—C35—C36 | 119.71 (19) |
C8—C9—C10 | 119.3 (2) | N5—C36—C28 | 123.35 (19) |
C8—C9—H9 | 120.3 | N5—C36—C35 | 117.12 (17) |
C10—C9—H9 | 120.3 | C28—C36—C35 | 119.52 (19) |
N2—C10—C9 | 123.0 (2) | O1—C37—C40 | 136.1 (2) |
N2—C10—H10 | 118.5 | O1—C37—C38 | 134.1 (2) |
C9—C10—H10 | 118.5 | C40—C37—C38 | 89.71 (18) |
N2—C11—C7 | 122.8 (2) | O2—C38—C39 | 136.8 (2) |
N2—C11—C12 | 117.27 (18) | O2—C38—C37 | 133.8 (2) |
C7—C11—C12 | 119.95 (19) | C39—C38—C37 | 89.35 (18) |
N1—C12—C4 | 122.8 (2) | O3—C39—C40 | 134.9 (2) |
N1—C12—C11 | 117.51 (17) | O3—C39—C38 | 134.6 (2) |
C4—C12—C11 | 119.7 (2) | C40—C39—C38 | 90.45 (18) |
N3—C13—C14 | 123.0 (2) | O4—C40—C39 | 134.4 (2) |
N3—C13—H13 | 118.5 | O4—C40—C37 | 135.1 (2) |
C14—C13—H13 | 118.5 | C39—C40—C37 | 90.43 (18) |
C15—C14—C13 | 119.3 (2) | C1—N1—C12 | 118.47 (18) |
C15—C14—H14 | 120.4 | C1—N1—Ni1 | 129.00 (14) |
C13—C14—H14 | 120.4 | C12—N1—Ni1 | 112.52 (13) |
C14—C15—C16 | 119.7 (2) | C10—N2—C11 | 117.90 (19) |
C14—C15—H15 | 120.2 | C10—N2—Ni1 | 129.39 (15) |
C16—C15—H15 | 120.2 | C11—N2—Ni1 | 112.66 (13) |
C24—C16—C15 | 117.3 (2) | C13—N3—C24 | 117.89 (18) |
C24—C16—C17 | 118.6 (2) | C13—N3—Ni1 | 129.26 (14) |
C15—C16—C17 | 124.1 (2) | C24—N3—Ni1 | 112.85 (13) |
C18—C17—C16 | 121.0 (3) | C22—N4—C23 | 118.48 (18) |
C18—C17—H17 | 119.5 | C22—N4—Ni1 | 128.91 (15) |
C16—C17—H17 | 119.5 | C23—N4—Ni1 | 112.48 (13) |
C17—C18—C19 | 122.0 (2) | C25—N5—C36 | 117.74 (18) |
C17—C18—H18 | 119.0 | C25—N5—Ni1 | 129.06 (15) |
C19—C18—H18 | 119.0 | C36—N5—Ni1 | 113.18 (12) |
C23—C19—C20 | 117.0 (2) | C34—N6—C35 | 117.52 (18) |
C23—C19—C18 | 118.3 (2) | C34—N6—Ni1 | 130.02 (15) |
C20—C19—C18 | 124.7 (2) | C35—N6—Ni1 | 112.45 (12) |
C21—C20—C19 | 120.4 (2) | H5A—O5—H5B | 108 (2) |
C21—C20—H20 | 119.8 | H6A—O6—H6B | 105 (2) |
C19—C20—H20 | 119.8 | H7A—O7—H7B | 105 (2) |
C20—C21—C22 | 119.1 (2) | H8A—O8—H8B | 106 (2) |
C20—C21—H21 | 120.4 | H9A—O9—H9B | 110 (2) |
C22—C21—H21 | 120.4 | H10A—O10—H10B | 109 (2) |
N4—C22—C21 | 122.7 (2) | H11A—O11—H11B | 108 (2) |
N4—C22—H22 | 118.7 | H12A—O12—H12B | 103.2 (16) |
C21—C22—H22 | 118.7 | N1—Ni1—N2 | 80.02 (7) |
N4—C23—C19 | 122.2 (2) | N1—Ni1—N5 | 94.31 (6) |
N4—C23—C24 | 117.64 (18) | N2—Ni1—N5 | 170.69 (7) |
C19—C23—C24 | 120.1 (2) | N1—Ni1—N3 | 94.59 (6) |
N3—C24—C16 | 122.8 (2) | N2—Ni1—N3 | 93.26 (6) |
N3—C24—C23 | 117.08 (18) | N5—Ni1—N3 | 94.56 (6) |
C16—C24—C23 | 120.1 (2) | N1—Ni1—N4 | 170.99 (6) |
N5—C25—C26 | 122.8 (2) | N2—Ni1—N4 | 93.13 (7) |
N5—C25—H25 | 118.6 | N5—Ni1—N4 | 93.21 (6) |
C26—C25—H25 | 118.6 | N3—Ni1—N4 | 79.85 (7) |
C27—C26—C25 | 119.5 (2) | N1—Ni1—N6 | 91.68 (6) |
C27—C26—H26 | 120.2 | N2—Ni1—N6 | 92.96 (6) |
C25—C26—H26 | 120.2 | N5—Ni1—N6 | 79.75 (6) |
C26—C27—C28 | 120.1 (2) | N3—Ni1—N6 | 171.84 (6) |
C26—C27—H27 | 119.9 | N4—Ni1—N6 | 94.54 (6) |
C28—C27—H27 | 119.9 | | |
| | | |
N1—C1—C2—C3 | −0.1 (4) | C38—C37—C40—O4 | 178.8 (3) |
C1—C2—C3—C4 | 0.8 (4) | O1—C37—C40—C39 | 174.8 (3) |
C2—C3—C4—C12 | −1.0 (4) | C38—C37—C40—C39 | −1.90 (18) |
C2—C3—C4—C5 | 177.9 (3) | C2—C1—N1—C12 | −0.5 (3) |
C12—C4—C5—C6 | 0.1 (4) | C2—C1—N1—Ni1 | 178.29 (17) |
C3—C4—C5—C6 | −178.7 (3) | C4—C12—N1—C1 | 0.3 (3) |
C4—C5—C6—C7 | −1.0 (4) | C11—C12—N1—C1 | −179.87 (18) |
C5—C6—C7—C8 | −179.3 (2) | C4—C12—N1—Ni1 | −178.68 (17) |
C5—C6—C7—C11 | 0.1 (4) | C11—C12—N1—Ni1 | 1.2 (2) |
C11—C7—C8—C9 | 0.0 (3) | C9—C10—N2—C11 | 0.5 (3) |
C6—C7—C8—C9 | 179.4 (2) | C9—C10—N2—Ni1 | 177.42 (17) |
C7—C8—C9—C10 | −0.2 (4) | C7—C11—N2—C10 | −0.6 (3) |
C8—C9—C10—N2 | −0.1 (4) | C12—C11—N2—C10 | 178.69 (19) |
C8—C7—C11—N2 | 0.3 (3) | C7—C11—N2—Ni1 | −178.05 (15) |
C6—C7—C11—N2 | −179.1 (2) | C12—C11—N2—Ni1 | 1.2 (2) |
C8—C7—C11—C12 | −178.92 (19) | C14—C13—N3—C24 | 1.0 (3) |
C6—C7—C11—C12 | 1.7 (3) | C14—C13—N3—Ni1 | −178.93 (17) |
C3—C4—C12—N1 | 0.4 (3) | C16—C24—N3—C13 | −1.7 (3) |
C5—C4—C12—N1 | −178.5 (2) | C23—C24—N3—C13 | 178.39 (19) |
C3—C4—C12—C11 | −179.4 (2) | C16—C24—N3—Ni1 | 178.25 (18) |
C5—C4—C12—C11 | 1.6 (3) | C23—C24—N3—Ni1 | −1.6 (2) |
N2—C11—C12—N1 | −1.7 (3) | C21—C22—N4—C23 | −0.7 (3) |
C7—C11—C12—N1 | 177.64 (17) | C21—C22—N4—Ni1 | 174.94 (18) |
N2—C11—C12—C4 | 178.20 (19) | C19—C23—N4—C22 | −0.4 (3) |
C7—C11—C12—C4 | −2.5 (3) | C24—C23—N4—C22 | 179.16 (19) |
N3—C13—C14—C15 | 0.2 (4) | C19—C23—N4—Ni1 | −176.74 (18) |
C13—C14—C15—C16 | −0.8 (4) | C24—C23—N4—Ni1 | 2.9 (2) |
C14—C15—C16—C24 | 0.1 (4) | C26—C25—N5—C36 | 0.4 (3) |
C14—C15—C16—C17 | −178.4 (3) | C26—C25—N5—Ni1 | −177.92 (16) |
C24—C16—C17—C18 | 1.3 (5) | C28—C36—N5—C25 | −0.2 (3) |
C15—C16—C17—C18 | 179.9 (3) | C35—C36—N5—C25 | −179.18 (17) |
C16—C17—C18—C19 | −0.9 (5) | C28—C36—N5—Ni1 | 178.42 (15) |
C17—C18—C19—C23 | −0.6 (5) | C35—C36—N5—Ni1 | −0.57 (19) |
C17—C18—C19—C20 | 179.5 (3) | C33—C34—N6—C35 | −0.3 (3) |
C23—C19—C20—C21 | −0.6 (4) | C33—C34—N6—Ni1 | 178.18 (16) |
C18—C19—C20—C21 | 179.3 (3) | C31—C35—N6—C34 | 1.8 (3) |
C19—C20—C21—C22 | −0.4 (4) | C36—C35—N6—C34 | −177.55 (17) |
C20—C21—C22—N4 | 1.1 (4) | C31—C35—N6—Ni1 | −176.92 (14) |
C20—C19—C23—N4 | 1.1 (4) | C36—C35—N6—Ni1 | 3.68 (19) |
C18—C19—C23—N4 | −178.9 (2) | C1—N1—Ni1—N2 | −179.20 (19) |
C20—C19—C23—C24 | −178.5 (2) | C12—N1—Ni1—N2 | −0.39 (13) |
C18—C19—C23—C24 | 1.6 (4) | C1—N1—Ni1—N5 | 8.25 (19) |
C15—C16—C24—N3 | 1.1 (4) | C12—N1—Ni1—N5 | −172.94 (13) |
C17—C16—C24—N3 | 179.8 (2) | C1—N1—Ni1—N3 | −86.69 (19) |
C15—C16—C24—C23 | −179.0 (2) | C12—N1—Ni1—N3 | 92.12 (14) |
C17—C16—C24—C23 | −0.3 (4) | C1—N1—Ni1—N6 | 88.09 (19) |
N4—C23—C24—N3 | −0.8 (3) | C12—N1—Ni1—N6 | −93.10 (14) |
C19—C23—C24—N3 | 178.8 (2) | C10—N2—Ni1—N1 | −177.5 (2) |
N4—C23—C24—C16 | 179.3 (2) | C11—N2—Ni1—N1 | −0.46 (13) |
C19—C23—C24—C16 | −1.1 (3) | C10—N2—Ni1—N3 | 88.36 (19) |
N5—C25—C26—C27 | −0.5 (4) | C11—N2—Ni1—N3 | −94.56 (14) |
C25—C26—C27—C28 | 0.3 (3) | C10—N2—Ni1—N4 | 8.4 (2) |
C26—C27—C28—C36 | −0.1 (3) | C11—N2—Ni1—N4 | −174.56 (14) |
C26—C27—C28—C29 | 177.6 (2) | C10—N2—Ni1—N6 | −86.35 (19) |
C36—C28—C29—C30 | 0.2 (3) | C11—N2—Ni1—N6 | 90.73 (14) |
C27—C28—C29—C30 | −177.4 (2) | C25—N5—Ni1—N1 | −88.74 (18) |
C28—C29—C30—C31 | −2.1 (3) | C36—N5—Ni1—N1 | 92.85 (13) |
C29—C30—C31—C35 | 2.7 (3) | C25—N5—Ni1—N3 | 6.23 (18) |
C29—C30—C31—C32 | −176.5 (2) | C36—N5—Ni1—N3 | −172.18 (13) |
C35—C31—C32—C33 | −0.4 (3) | C25—N5—Ni1—N4 | 86.29 (18) |
C30—C31—C32—C33 | 178.7 (2) | C36—N5—Ni1—N4 | −92.12 (13) |
C31—C32—C33—C34 | 1.9 (3) | C25—N5—Ni1—N6 | −179.67 (18) |
C32—C33—C34—N6 | −1.5 (4) | C36—N5—Ni1—N6 | 1.92 (13) |
C32—C31—C35—N6 | −1.5 (3) | C13—N3—Ni1—N1 | 9.51 (19) |
C30—C31—C35—N6 | 179.32 (18) | C24—N3—Ni1—N1 | −170.46 (14) |
C32—C31—C35—C36 | 177.92 (17) | C13—N3—Ni1—N2 | 89.75 (19) |
C30—C31—C35—C36 | −1.3 (3) | C24—N3—Ni1—N2 | −90.22 (14) |
C27—C28—C36—N5 | 0.0 (3) | C13—N3—Ni1—N5 | −85.19 (19) |
C29—C28—C36—N5 | −177.78 (18) | C24—N3—Ni1—N5 | 94.83 (14) |
C27—C28—C36—C35 | 178.98 (17) | C13—N3—Ni1—N4 | −177.64 (19) |
C29—C28—C36—C35 | 1.2 (3) | C24—N3—Ni1—N4 | 2.38 (14) |
N6—C35—C36—N5 | −2.1 (2) | C22—N4—Ni1—N2 | −85.88 (19) |
C31—C35—C36—N5 | 178.43 (17) | C23—N4—Ni1—N2 | 89.95 (14) |
N6—C35—C36—C28 | 178.82 (17) | C22—N4—Ni1—N5 | 87.30 (19) |
C31—C35—C36—C28 | −0.6 (2) | C23—N4—Ni1—N5 | −96.87 (14) |
O1—C37—C38—O2 | 3.7 (5) | C22—N4—Ni1—N3 | −178.63 (19) |
C40—C37—C38—O2 | −179.4 (3) | C23—N4—Ni1—N3 | −2.80 (14) |
O1—C37—C38—C39 | −174.9 (3) | C22—N4—Ni1—N6 | 7.34 (19) |
C40—C37—C38—C39 | 1.89 (18) | C23—N4—Ni1—N6 | −176.83 (14) |
O2—C38—C39—O3 | −2.7 (5) | C34—N6—Ni1—N1 | 84.35 (18) |
C37—C38—C39—O3 | 175.9 (3) | C35—N6—Ni1—N1 | −97.08 (13) |
O2—C38—C39—C40 | 179.5 (3) | C34—N6—Ni1—N2 | 4.26 (18) |
C37—C38—C39—C40 | −1.90 (18) | C35—N6—Ni1—N2 | −177.17 (13) |
O3—C39—C40—O4 | 3.5 (5) | C34—N6—Ni1—N5 | 178.42 (18) |
C38—C39—C40—O4 | −178.8 (3) | C35—N6—Ni1—N5 | −3.01 (13) |
O3—C39—C40—C37 | −175.8 (3) | C34—N6—Ni1—N4 | −89.13 (18) |
C38—C39—C40—C37 | 1.92 (18) | C35—N6—Ni1—N4 | 89.44 (13) |
O1—C37—C40—O4 | −4.5 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O10 | 0.84 (3) | 1.98 (3) | 2.804 (3) | 166 (4) |
O5—H5B···O4i | 0.84 (2) | 1.88 (2) | 2.723 (3) | 178 (3) |
O6—H6A···O5 | 0.85 (3) | 1.99 (3) | 2.788 (3) | 155 (4) |
O6—H6B···O7ii | 0.85 (3) | 1.96 (3) | 2.776 (3) | 160 (3) |
O7—H7A···O6iii | 0.84 (3) | 2.18 (3) | 2.886 (3) | 141 (3) |
O7—H7B···O8iv | 0.84 (3) | 1.93 (3) | 2.747 (3) | 163 (3) |
O8—H8A···O9iii | 0.85 (2) | 2.02 (2) | 2.843 (3) | 162 (3) |
O8—H8B···O11 | 0.86 (2) | 1.85 (2) | 2.698 (3) | 171 (3) |
O9—H9A···O1v | 0.83 (2) | 2.02 (2) | 2.825 (3) | 164 (3) |
O9—H9B···O2vi | 0.84 (2) | 1.90 (2) | 2.735 (2) | 173 (3) |
O10—H10A···O9 | 0.84 (2) | 2.04 (2) | 2.848 (2) | 163 (3) |
O10—H10B···O3vi | 0.84 (2) | 1.88 (2) | 2.716 (3) | 170 (3) |
O11—H11A···O12 | 0.84 (2) | 1.97 (2) | 2.797 (4) | 167 (3) |
O11—H11B···O4 | 0.85 (2) | 1.92 (2) | 2.746 (3) | 163 (3) |
O12—H12B···O3 | 0.86 (3) | 1.92 (3) | 2.765 (4) | 167 (3) |
C6—H6···O2vii | 0.93 | 2.58 | 3.464 (3) | 159 |
C30—H30···O1v | 0.93 | 2.51 | 3.306 (4) | 144 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1; (iii) x+1, y, z; (iv) x, −y+1/2, z+1/2; (v) −x+1, y+1/2, −z+1/2; (vi) x−1, −y+1/2, z+1/2; (vii) −x+1, −y, −z. |