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metal-organic compounds
The Ni atom in the title compound, [Ni(C20H38N4O4)]·4H2O, is chelated by four N atoms of the macrocycle and also covalently bonded to two carboxylate groups, in a cis-N4O2Ni octahedral environment. The mononuclear complex interacts with the solvent water molecules to form a three-dimensional network structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805021033/ci6607sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805021033/ci6607Isup2.hkl |
CCDC reference: 282277
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.055
- wR factor = 0.139
- Data-to-parameter ratio = 19.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H3W2 .. H4W2 .. 2.04 Ang. PLAT420_ALERT_2_B D-H Without Acceptor O4W - H4W1 ... ?
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.713 0.902 Tmin(prime) and Tmax expected: 0.839 0.900 RR(prime) = 0.847 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.84 PLAT417_ALERT_2_C Short Inter D-H..H-D H3W2 .. H4W1 .. 2.13 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
(5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-1,8-
diacetato)nickel(II) tetrahydrate top
Crystal data top
[Ni(C20H38N4O4)]·4H2O | F(000) = 1144 |
Mr = 529.32 | Dx = 1.384 Mg m−3 Dm = 1.380 Mg m−3 Dm measured by flotation in CH2Cl2/CHCl3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8736 reflections |
a = 9.1863 (6) Å | θ = 2.4–28.3° |
b = 13.8653 (9) Å | µ = 0.81 mm−1 |
c = 19.987 (1) Å | T = 295 K |
β = 93.604 (1)° | Prism, blue |
V = 2540.7 (3) Å3 | 0.21 × 0.18 × 0.13 mm |
Z = 4 |
Data collection top
Bruker APEX area-detector diffractometer | 5770 independent reflections |
Radiation source: fine-focus sealed tube | 5188 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
φ and ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→11 |
Tmin = 0.713, Tmax = 0.902 | k = −17→18 |
21339 measured reflections | l = −25→25 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0534P)2 + 2.6926P] where P = (Fo2 + 2Fc2)/3 |
5770 reflections | (Δ/σ)max = 0.001 |
298 parameters | Δρmax = 0.66 e Å−3 |
24 restraints | Δρmin = −0.68 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.62450 (4) | 0.39195 (2) | 0.252575 (17) | 0.02529 (12) | |
O1 | 0.5296 (2) | 0.49268 (15) | 0.31572 (11) | 0.0365 (5) | |
O2 | 0.3917 (3) | 0.62511 (18) | 0.30452 (15) | 0.0532 (7) | |
O3 | 0.7595 (2) | 0.51133 (15) | 0.23475 (10) | 0.0338 (5) | |
O4 | 0.9252 (3) | 0.59946 (16) | 0.29356 (14) | 0.0494 (6) | |
O1W | 0.5737 (4) | 0.5588 (3) | 0.45332 (17) | 0.0903 (11) | |
H1W1 | 0.5665 | 0.5306 | 0.4155 | 0.135* | |
H1W2 | 0.4936 | 0.5863 | 0.4607 | 0.135* | |
O2W | 0.8572 (7) | 0.5195 (6) | 0.5092 (3) | 0.172 (2) | |
H2W1 | 0.7699 | 0.5379 | 0.4994 | 0.258* | |
H2W2 | 0.8564 | 0.4598 | 0.5204 | 0.258* | |
O3W | 0.1271 (9) | 0.6186 (5) | 0.4048 (4) | 0.203 (3) | |
H3W1 | 0.0372 | 0.6274 | 0.3918 | 0.304* | |
H3W2 | 0.1767 | 0.6657 | 0.3878 | 0.304* | |
O4W | 0.3473 (9) | 0.7063 (6) | 0.4239 (4) | 0.208 (3) | |
H4W1 | 0.3245 | 0.7655 | 0.4363 | 0.312* | |
H4W2 | 0.3849 | 0.7163 | 0.3853 | 0.312* | |
N1 | 0.4302 (3) | 0.42481 (19) | 0.19563 (13) | 0.0340 (5) | |
N2 | 0.6992 (3) | 0.30603 (18) | 0.17542 (12) | 0.0332 (5) | |
H2N | 0.6345 | 0.2614 | 0.1701 | 0.040* | |
N3 | 0.8168 (3) | 0.35176 (16) | 0.30689 (12) | 0.0284 (5) | |
N4 | 0.5097 (3) | 0.27361 (18) | 0.28789 (12) | 0.0319 (5) | |
H4N | 0.5570 | 0.2243 | 0.2747 | 0.038* | |
C1 | 0.4461 (3) | 0.5513 (2) | 0.28269 (17) | 0.0365 (7) | |
C2 | 0.4100 (4) | 0.5285 (2) | 0.20906 (17) | 0.0426 (8) | |
H2A | 0.3098 | 0.5465 | 0.1970 | 0.051* | |
H2B | 0.4727 | 0.5660 | 0.1817 | 0.051* | |
C3 | 0.4356 (4) | 0.4015 (3) | 0.12262 (17) | 0.0448 (8) | |
H3 | 0.4234 | 0.3316 | 0.1179 | 0.054* | |
C4 | 0.3129 (5) | 0.4493 (4) | 0.0789 (2) | 0.0664 (12) | |
H4A | 0.2203 | 0.4314 | 0.0949 | 0.100* | |
H4B | 0.3178 | 0.4284 | 0.0333 | 0.100* | |
H4C | 0.3238 | 0.5181 | 0.0811 | 0.100* | |
C5 | 0.5847 (4) | 0.4269 (3) | 0.09825 (17) | 0.0475 (8) | |
H5A | 0.6192 | 0.4845 | 0.1218 | 0.057* | |
H5B | 0.5718 | 0.4433 | 0.0511 | 0.057* | |
C6 | 0.7056 (4) | 0.3499 (3) | 0.10642 (16) | 0.0422 (8) | |
C7 | 0.8517 (5) | 0.3991 (3) | 0.0974 (2) | 0.0572 (10) | |
H7A | 0.9287 | 0.3523 | 0.1023 | 0.086* | |
H7B | 0.8676 | 0.4484 | 0.1308 | 0.086* | |
H7C | 0.8508 | 0.4275 | 0.0536 | 0.086* | |
C8 | 0.6802 (5) | 0.2698 (3) | 0.05386 (19) | 0.0658 (12) | |
H8A | 0.7561 | 0.2224 | 0.0597 | 0.099* | |
H8B | 0.6813 | 0.2972 | 0.0098 | 0.099* | |
H8C | 0.5875 | 0.2399 | 0.0592 | 0.099* | |
C9 | 0.8319 (3) | 0.2544 (2) | 0.20329 (17) | 0.0386 (7) | |
H9A | 0.8944 | 0.2395 | 0.1673 | 0.046* | |
H9B | 0.8035 | 0.1941 | 0.2233 | 0.046* | |
C10 | 0.9159 (3) | 0.3152 (2) | 0.25579 (16) | 0.0355 (7) | |
H10A | 0.9930 | 0.2768 | 0.2778 | 0.043* | |
H10B | 0.9606 | 0.3694 | 0.2342 | 0.043* | |
C11 | 0.8761 (3) | 0.4438 (2) | 0.33424 (16) | 0.0344 (6) | |
H11A | 0.9796 | 0.4367 | 0.3458 | 0.041* | |
H11B | 0.8285 | 0.4601 | 0.3747 | 0.041* | |
C12 | 0.8517 (3) | 0.5244 (2) | 0.28302 (16) | 0.0336 (6) | |
C13 | 0.7914 (3) | 0.2769 (2) | 0.35950 (16) | 0.0357 (7) | |
H13 | 0.7750 | 0.2153 | 0.3362 | 0.043* | |
C14 | 0.9218 (4) | 0.2630 (3) | 0.4099 (2) | 0.0555 (10) | |
H14A | 1.0071 | 0.2488 | 0.3863 | 0.083* | |
H14B | 0.9025 | 0.2106 | 0.4394 | 0.083* | |
H14C | 0.9376 | 0.3211 | 0.4355 | 0.083* | |
C15 | 0.6527 (4) | 0.3001 (2) | 0.39488 (15) | 0.0391 (7) | |
H15A | 0.6441 | 0.3697 | 0.3977 | 0.047* | |
H15B | 0.6648 | 0.2757 | 0.4404 | 0.047* | |
C16 | 0.5078 (4) | 0.2603 (2) | 0.36284 (16) | 0.0385 (7) | |
C17 | 0.3832 (4) | 0.3154 (3) | 0.3922 (2) | 0.0545 (10) | |
H17A | 0.2918 | 0.2919 | 0.3727 | 0.082* | |
H17B | 0.3924 | 0.3828 | 0.3824 | 0.082* | |
H17C | 0.3871 | 0.3061 | 0.4398 | 0.082* | |
C18 | 0.4962 (5) | 0.1517 (3) | 0.3774 (2) | 0.0574 (10) | |
H18A | 0.4058 | 0.1274 | 0.3574 | 0.086* | |
H18B | 0.4995 | 0.1416 | 0.4250 | 0.086* | |
H18C | 0.5761 | 0.1185 | 0.3589 | 0.086* | |
C19 | 0.3675 (3) | 0.2691 (2) | 0.24787 (18) | 0.0417 (7) | |
H19A | 0.2957 | 0.2380 | 0.2742 | 0.050* | |
H19B | 0.3784 | 0.2304 | 0.2081 | 0.050* | |
C20 | 0.3139 (3) | 0.3692 (2) | 0.22733 (18) | 0.0401 (7) | |
H20A | 0.2294 | 0.3636 | 0.1959 | 0.048* | |
H20B | 0.2845 | 0.4036 | 0.2665 | 0.048* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.02330 (19) | 0.02274 (19) | 0.0294 (2) | 0.00150 (13) | −0.00140 (13) | −0.00099 (13) |
O1 | 0.0401 (12) | 0.0320 (11) | 0.0373 (11) | 0.0033 (9) | 0.0020 (9) | −0.0038 (9) |
O2 | 0.0446 (14) | 0.0378 (13) | 0.0772 (18) | 0.0109 (11) | 0.0032 (13) | −0.0157 (12) |
O3 | 0.0358 (11) | 0.0272 (10) | 0.0380 (11) | −0.0006 (8) | −0.0016 (9) | 0.0041 (8) |
O4 | 0.0484 (14) | 0.0280 (12) | 0.0697 (17) | −0.0128 (10) | −0.0120 (12) | 0.0095 (11) |
O1W | 0.111 (3) | 0.092 (3) | 0.066 (2) | −0.013 (2) | −0.0014 (19) | −0.0151 (19) |
O2W | 0.132 (4) | 0.227 (6) | 0.157 (5) | 0.004 (4) | 0.003 (4) | 0.004 (5) |
O3W | 0.236 (6) | 0.152 (5) | 0.203 (6) | 0.004 (5) | −0.122 (5) | 0.003 (4) |
O4W | 0.222 (6) | 0.222 (7) | 0.182 (6) | 0.035 (6) | 0.023 (5) | −0.020 (5) |
N1 | 0.0312 (13) | 0.0329 (13) | 0.0374 (13) | 0.0049 (10) | −0.0040 (10) | −0.0031 (11) |
N2 | 0.0319 (13) | 0.0320 (13) | 0.0352 (13) | 0.0026 (10) | −0.0022 (10) | −0.0057 (10) |
N3 | 0.0274 (12) | 0.0222 (11) | 0.0350 (12) | −0.0015 (9) | −0.0031 (10) | 0.0031 (9) |
N4 | 0.0302 (13) | 0.0268 (12) | 0.0385 (13) | −0.0011 (10) | 0.0008 (10) | −0.0027 (10) |
C1 | 0.0277 (15) | 0.0303 (15) | 0.0518 (18) | 0.0012 (12) | 0.0038 (13) | −0.0053 (13) |
C2 | 0.0421 (18) | 0.0343 (17) | 0.0501 (19) | 0.0124 (14) | −0.0062 (15) | 0.0021 (14) |
C3 | 0.0460 (19) | 0.049 (2) | 0.0372 (17) | 0.0088 (15) | −0.0120 (14) | −0.0052 (14) |
C4 | 0.059 (3) | 0.088 (3) | 0.049 (2) | 0.018 (2) | −0.0245 (19) | −0.001 (2) |
C5 | 0.054 (2) | 0.054 (2) | 0.0345 (17) | 0.0109 (17) | −0.0008 (15) | 0.0039 (15) |
C6 | 0.0459 (19) | 0.050 (2) | 0.0309 (15) | 0.0072 (15) | 0.0017 (13) | −0.0061 (14) |
C7 | 0.057 (2) | 0.067 (3) | 0.049 (2) | 0.006 (2) | 0.0142 (18) | 0.0071 (19) |
C8 | 0.077 (3) | 0.078 (3) | 0.041 (2) | 0.013 (2) | −0.0058 (19) | −0.024 (2) |
C9 | 0.0360 (17) | 0.0322 (16) | 0.0476 (18) | 0.0086 (13) | 0.0032 (13) | −0.0037 (13) |
C10 | 0.0222 (14) | 0.0345 (16) | 0.0492 (18) | 0.0062 (11) | −0.0027 (12) | 0.0042 (13) |
C11 | 0.0357 (16) | 0.0257 (14) | 0.0400 (16) | −0.0062 (12) | −0.0116 (13) | 0.0006 (12) |
C12 | 0.0323 (15) | 0.0262 (14) | 0.0422 (16) | −0.0015 (11) | 0.0013 (12) | 0.0019 (12) |
C13 | 0.0385 (17) | 0.0272 (15) | 0.0402 (16) | −0.0022 (12) | −0.0073 (13) | 0.0083 (12) |
C14 | 0.055 (2) | 0.053 (2) | 0.056 (2) | −0.0039 (18) | −0.0208 (18) | 0.0217 (18) |
C15 | 0.0488 (19) | 0.0356 (16) | 0.0330 (15) | −0.0061 (14) | 0.0024 (13) | 0.0045 (13) |
C16 | 0.0393 (17) | 0.0355 (16) | 0.0415 (17) | −0.0095 (13) | 0.0087 (13) | 0.0035 (13) |
C17 | 0.051 (2) | 0.061 (2) | 0.054 (2) | −0.0097 (18) | 0.0183 (17) | −0.0032 (18) |
C18 | 0.068 (3) | 0.041 (2) | 0.064 (2) | −0.0178 (18) | 0.008 (2) | 0.0137 (18) |
C19 | 0.0309 (16) | 0.0359 (17) | 0.057 (2) | −0.0066 (13) | −0.0034 (14) | −0.0073 (15) |
C20 | 0.0270 (15) | 0.0405 (17) | 0.0520 (19) | 0.0014 (13) | −0.0053 (14) | −0.0054 (15) |
Geometric parameters (Å, º) top
Ni1—N1 | 2.106 (2) | C5—H5A | 0.97 |
Ni1—N2 | 2.098 (2) | C5—H5B | 0.97 |
Ni1—N3 | 2.090 (2) | C6—C7 | 1.526 (5) |
Ni1—N4 | 2.097 (2) | C6—C8 | 1.536 (5) |
Ni1—O1 | 2.108 (2) | C7—H7A | 0.96 |
Ni1—O3 | 2.112 (2) | C7—H7B | 0.96 |
O1—C1 | 1.273 (4) | C7—H7C | 0.96 |
O2—C1 | 1.231 (4) | C8—H8A | 0.96 |
O3—C12 | 1.257 (4) | C8—H8B | 0.96 |
O4—C12 | 1.251 (4) | C8—H8C | 0.96 |
O1W—H1W1 | 0.85 | C9—C10 | 1.518 (4) |
O1W—H1W2 | 0.85 | C9—H9A | 0.97 |
O2W—H2W1 | 0.85 | C9—H9B | 0.97 |
O2W—H2W2 | 0.86 | C10—H10A | 0.97 |
O3W—H3W1 | 0.86 | C10—H10B | 0.97 |
O3W—H3W2 | 0.88 | C11—C12 | 1.523 (4) |
O4W—H4W1 | 0.89 | C11—H11A | 0.97 |
O4W—H4W2 | 0.88 | C11—H11B | 0.97 |
N1—C2 | 1.477 (4) | C13—C14 | 1.527 (4) |
N1—C20 | 1.490 (4) | C13—C15 | 1.530 (5) |
N1—C3 | 1.498 (4) | C13—H13 | 0.98 |
N2—C9 | 1.492 (4) | C14—H14A | 0.96 |
N2—C6 | 1.512 (4) | C14—H14B | 0.96 |
N2—H2N | 0.86 | C14—H14C | 0.96 |
N3—C11 | 1.478 (4) | C15—C16 | 1.543 (5) |
N3—C10 | 1.499 (4) | C15—H15A | 0.97 |
N3—C13 | 1.506 (4) | C15—H15B | 0.97 |
N4—C19 | 1.490 (4) | C16—C17 | 1.523 (5) |
N4—C16 | 1.511 (4) | C16—C18 | 1.538 (5) |
N4—H4N | 0.86 | C17—H17A | 0.96 |
C1—C2 | 1.521 (5) | C17—H17B | 0.96 |
C2—H2A | 0.97 | C17—H17C | 0.96 |
C2—H2B | 0.97 | C18—H18A | 0.96 |
C3—C5 | 1.524 (5) | C18—H18B | 0.96 |
C3—C4 | 1.533 (5) | C18—H18C | 0.96 |
C3—H3 | 0.98 | C19—C20 | 1.521 (5) |
C4—H4A | 0.96 | C19—H19A | 0.97 |
C4—H4B | 0.96 | C19—H19B | 0.97 |
C4—H4C | 0.96 | C20—H20A | 0.97 |
C5—C6 | 1.542 (5) | C20—H20B | 0.97 |
N1—Ni1—N2 | 91.8 (1) | H7A—C7—H7B | 109.5 |
N1—Ni1—N3 | 176.9 (1) | C6—C7—H7C | 109.5 |
N1—Ni1—N4 | 85.6 (1) | H7A—C7—H7C | 109.5 |
N1—Ni1—O1 | 79.1 (1) | H7B—C7—H7C | 109.5 |
N1—Ni1—O3 | 103.1 (1) | C6—C8—H8A | 109.5 |
N2—Ni1—N3 | 85.7 (1) | C6—C8—H8B | 109.5 |
N2—Ni1—N4 | 89.9 (1) | H8A—C8—H8B | 109.5 |
N2—Ni1—O1 | 169.5 (1) | C6—C8—H8C | 109.5 |
N2—Ni1—O3 | 95.7 (1) | H8A—C8—H8C | 109.5 |
N3—Ni1—N4 | 92.5 (1) | H8B—C8—H8C | 109.5 |
N3—Ni1—O1 | 103.5 (1) | N2—C9—C10 | 111.1 (2) |
N3—Ni1—O3 | 79.1 (1) | N2—C9—H9A | 109.4 |
N4—Ni1—O1 | 94.7 (1) | C10—C9—H9A | 109.4 |
N4—Ni1—O3 | 169.5 (1) | N2—C9—H9B | 109.4 |
O1—Ni1—O3 | 81.4 (1) | C10—C9—H9B | 109.4 |
C1—O1—Ni1 | 111.77 (19) | H9A—C9—H9B | 108.0 |
C12—O3—Ni1 | 111.00 (18) | N3—C10—C9 | 110.8 (2) |
H1W1—O1W—H1W2 | 110.0 | N3—C10—H10A | 109.5 |
H2W1—O2W—H2W2 | 109.0 | C9—C10—H10A | 109.5 |
H3W1—O3W—H3W2 | 106.9 | N3—C10—H10B | 109.5 |
H4W1—O4W—H4W2 | 102.3 | C9—C10—H10B | 109.5 |
C2—N1—C20 | 109.0 (3) | H10A—C10—H10B | 108.1 |
C2—N1—C3 | 113.5 (3) | N3—C11—C12 | 110.5 (2) |
C20—N1—C3 | 111.8 (3) | N3—C11—H11A | 109.6 |
C2—N1—Ni1 | 102.96 (19) | C12—C11—H11A | 109.6 |
C20—N1—Ni1 | 105.32 (19) | N3—C11—H11B | 109.6 |
C3—N1—Ni1 | 113.62 (19) | C12—C11—H11B | 109.6 |
C9—N2—C6 | 117.1 (2) | H11A—C11—H11B | 108.1 |
C9—N2—Ni1 | 107.18 (18) | O4—C12—O3 | 125.5 (3) |
C6—N2—Ni1 | 118.40 (19) | O4—C12—C11 | 116.3 (3) |
C9—N2—H2N | 104.1 | O3—C12—C11 | 118.3 (3) |
C6—N2—H2N | 104.1 | N3—C13—C14 | 113.4 (3) |
Ni1—N2—H2N | 104.1 | N3—C13—C15 | 110.3 (2) |
C11—N3—C10 | 108.6 (2) | C14—C13—C15 | 111.3 (3) |
C11—N3—C13 | 114.0 (2) | N3—C13—H13 | 107.2 |
C10—N3—C13 | 111.7 (2) | C14—C13—H13 | 107.2 |
C11—N3—Ni1 | 103.98 (17) | C15—C13—H13 | 107.2 |
C10—N3—Ni1 | 105.42 (17) | C13—C14—H14A | 109.5 |
C13—N3—Ni1 | 112.57 (18) | C13—C14—H14B | 109.5 |
C19—N4—C16 | 117.6 (2) | H14A—C14—H14B | 109.5 |
C19—N4—Ni1 | 107.16 (19) | C13—C14—H14C | 109.5 |
C16—N4—Ni1 | 117.86 (18) | H14A—C14—H14C | 109.5 |
C19—N4—H4N | 104.1 | H14B—C14—H14C | 109.5 |
C16—N4—H4N | 104.1 | C13—C15—C16 | 117.0 (3) |
Ni1—N4—H4N | 104.1 | C13—C15—H15A | 108.0 |
O2—C1—O1 | 126.3 (3) | C16—C15—H15A | 108.0 |
O2—C1—C2 | 116.5 (3) | C13—C15—H15B | 108.0 |
O1—C1—C2 | 117.2 (3) | C16—C15—H15B | 108.0 |
N1—C2—C1 | 110.8 (3) | H15A—C15—H15B | 107.3 |
N1—C2—H2A | 109.5 | N4—C16—C17 | 112.1 (3) |
C1—C2—H2A | 109.5 | N4—C16—C18 | 108.2 (3) |
N1—C2—H2B | 109.5 | C17—C16—C18 | 110.8 (3) |
C1—C2—H2B | 109.5 | N4—C16—C15 | 107.7 (2) |
H2A—C2—H2B | 108.1 | C17—C16—C15 | 108.1 (3) |
N1—C3—C5 | 110.3 (3) | C18—C16—C15 | 109.9 (3) |
N1—C3—C4 | 113.2 (3) | C16—C17—H17A | 109.5 |
C5—C3—C4 | 111.2 (3) | C16—C17—H17B | 109.5 |
N1—C3—H3 | 107.3 | H17A—C17—H17B | 109.5 |
C5—C3—H3 | 107.3 | C16—C17—H17C | 109.5 |
C4—C3—H3 | 107.3 | H17A—C17—H17C | 109.5 |
C3—C4—H4A | 109.5 | H17B—C17—H17C | 109.5 |
C3—C4—H4B | 109.5 | C16—C18—H18A | 109.5 |
H4A—C4—H4B | 109.5 | C16—C18—H18B | 109.5 |
C3—C4—H4C | 109.5 | H18A—C18—H18B | 109.5 |
H4A—C4—H4C | 109.5 | C16—C18—H18C | 109.5 |
H4B—C4—H4C | 109.5 | H18A—C18—H18C | 109.5 |
C3—C5—C6 | 117.5 (3) | H18B—C18—H18C | 109.5 |
C3—C5—H5A | 107.9 | N4—C19—C20 | 111.4 (3) |
C6—C5—H5A | 107.9 | N4—C19—H19A | 109.4 |
C3—C5—H5B | 107.9 | C20—C19—H19A | 109.4 |
C6—C5—H5B | 107.9 | N4—C19—H19B | 109.4 |
H5A—C5—H5B | 107.2 | C20—C19—H19B | 109.4 |
N2—C6—C7 | 111.8 (3) | H19A—C19—H19B | 108.0 |
N2—C6—C8 | 108.7 (3) | N1—C20—C19 | 111.0 (3) |
C7—C6—C8 | 109.8 (3) | N1—C20—H20A | 109.4 |
N2—C6—C5 | 107.8 (2) | C19—C20—H20A | 109.4 |
C7—C6—C5 | 108.1 (3) | N1—C20—H20B | 109.4 |
C8—C6—C5 | 110.5 (3) | C19—C20—H20B | 109.4 |
C6—C7—H7A | 109.5 | H20A—C20—H20B | 108.0 |
C6—C7—H7B | 109.5 | ||
N3—Ni1—O1—C1 | 154.5 (2) | C3—N1—C2—C1 | −164.7 (3) |
N4—Ni1—O1—C1 | −111.8 (2) | Ni1—N1—C2—C1 | −41.4 (3) |
N2—Ni1—O1—C1 | 3.4 (6) | O2—C1—C2—N1 | −157.7 (3) |
N1—Ni1—O1—C1 | −27.2 (2) | O1—C1—C2—N1 | 22.5 (4) |
O3—Ni1—O1—C1 | 78.0 (2) | C2—N1—C3—C5 | 77.9 (3) |
N3—Ni1—O3—C12 | −29.3 (2) | C20—N1—C3—C5 | −158.3 (3) |
N4—Ni1—O3—C12 | 7.6 (6) | Ni1—N1—C3—C5 | −39.3 (3) |
N2—Ni1—O3—C12 | −113.8 (2) | C2—N1—C3—C4 | −47.3 (4) |
N1—Ni1—O3—C12 | 153.1 (2) | C20—N1—C3—C4 | 76.4 (4) |
O1—Ni1—O3—C12 | 76.4 (2) | Ni1—N1—C3—C4 | −164.6 (3) |
N4—Ni1—N1—C2 | 131.7 (2) | N1—C3—C5—C6 | 86.8 (4) |
N2—Ni1—N1—C2 | −138.6 (2) | C4—C3—C5—C6 | −146.8 (3) |
O1—Ni1—N1—C2 | 36.1 (2) | C9—N2—C6—C7 | −41.8 (4) |
O3—Ni1—N1—C2 | −42.3 (2) | Ni1—N2—C6—C7 | 89.0 (3) |
N4—Ni1—N1—C20 | 17.58 (19) | C9—N2—C6—C8 | 79.6 (4) |
N2—Ni1—N1—C20 | 107.3 (2) | Ni1—N2—C6—C8 | −149.5 (3) |
O1—Ni1—N1—C20 | −78.02 (19) | C9—N2—C6—C5 | −160.5 (3) |
O3—Ni1—N1—C20 | −156.47 (18) | Ni1—N2—C6—C5 | −29.7 (3) |
N4—Ni1—N1—C3 | −105.1 (2) | C3—C5—C6—N2 | −43.4 (4) |
N2—Ni1—N1—C3 | −15.3 (2) | C3—C5—C6—C7 | −164.5 (3) |
O1—Ni1—N1—C3 | 159.3 (2) | C3—C5—C6—C8 | 75.3 (4) |
O3—Ni1—N1—C3 | 80.9 (2) | C6—N2—C9—C10 | 103.7 (3) |
N3—Ni1—N2—C9 | 7.5 (2) | Ni1—N2—C9—C10 | −32.2 (3) |
N4—Ni1—N2—C9 | −85.0 (2) | C11—N3—C10—C9 | −151.8 (2) |
N1—Ni1—N2—C9 | −170.6 (2) | C13—N3—C10—C9 | 81.7 (3) |
O1—Ni1—N2—C9 | 159.4 (5) | Ni1—N3—C10—C9 | −40.9 (3) |
O3—Ni1—N2—C9 | 86.1 (2) | N2—C9—C10—N3 | 50.7 (3) |
N3—Ni1—N2—C6 | −127.7 (2) | C10—N3—C11—C12 | 73.5 (3) |
N4—Ni1—N2—C6 | 139.8 (2) | C13—N3—C11—C12 | −161.3 (2) |
N1—Ni1—N2—C6 | 54.2 (2) | Ni1—N3—C11—C12 | −38.3 (3) |
O1—Ni1—N2—C6 | 24.2 (6) | Ni1—O3—C12—O4 | −164.3 (3) |
O3—Ni1—N2—C6 | −49.1 (2) | Ni1—O3—C12—C11 | 14.6 (3) |
N4—Ni1—N3—C11 | −138.13 (18) | N3—C11—C12—O4 | −164.0 (3) |
N2—Ni1—N3—C11 | 132.19 (19) | N3—C11—C12—O3 | 17.0 (4) |
O1—Ni1—N3—C11 | −42.73 (19) | C11—N3—C13—C14 | −48.8 (4) |
O3—Ni1—N3—C11 | 35.59 (18) | C10—N3—C13—C14 | 74.7 (3) |
N4—Ni1—N3—C10 | 107.73 (18) | Ni1—N3—C13—C14 | −166.9 (2) |
N2—Ni1—N3—C10 | 18.05 (18) | C11—N3—C13—C15 | 76.8 (3) |
O1—Ni1—N3—C10 | −156.88 (17) | C10—N3—C13—C15 | −159.7 (2) |
O3—Ni1—N3—C10 | −78.56 (18) | Ni1—N3—C13—C15 | −41.3 (3) |
N4—Ni1—N3—C13 | −14.3 (2) | N3—C13—C15—C16 | 87.7 (3) |
N2—Ni1—N3—C13 | −104.0 (2) | C14—C13—C15—C16 | −145.5 (3) |
O1—Ni1—N3—C13 | 81.1 (2) | C19—N4—C16—C17 | −43.0 (4) |
O3—Ni1—N3—C13 | 159.4 (2) | Ni1—N4—C16—C17 | 87.7 (3) |
N3—Ni1—N4—C19 | −169.62 (19) | C19—N4—C16—C18 | 79.5 (4) |
N2—Ni1—N4—C19 | −83.9 (2) | Ni1—N4—C16—C18 | −149.8 (2) |
N1—Ni1—N4—C19 | 7.90 (19) | C19—N4—C16—C15 | −161.7 (3) |
O1—Ni1—N4—C19 | 86.61 (19) | Ni1—N4—C16—C15 | −31.0 (3) |
O3—Ni1—N4—C19 | 154.2 (4) | C13—C15—C16—N4 | −41.8 (4) |
N3—Ni1—N4—C16 | 55.1 (2) | C13—C15—C16—C17 | −163.0 (3) |
N2—Ni1—N4—C16 | 140.8 (2) | C13—C15—C16—C18 | 75.9 (4) |
N1—Ni1—N4—C16 | −127.4 (2) | C16—N4—C19—C20 | 103.1 (3) |
O1—Ni1—N4—C16 | −48.7 (2) | Ni1—N4—C19—C20 | −32.4 (3) |
O3—Ni1—N4—C16 | 18.9 (6) | C2—N1—C20—C19 | −150.1 (3) |
Ni1—O1—C1—O2 | −169.6 (3) | C3—N1—C20—C19 | 83.6 (3) |
Ni1—O1—C1—C2 | 10.2 (3) | Ni1—N1—C20—C19 | −40.3 (3) |
C20—N1—C2—C1 | 70.1 (3) | N4—C19—C20—N1 | 50.6 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O4i | 0.86 | 2.43 | 3.160 (4) | 143 |
N4—H4N···O4i | 0.86 | 2.22 | 2.993 (3) | 150 |
O1W—H1W1···O1 | 0.85 | 2.07 | 2.903 (4) | 167 |
O1W—H1W2···O4W | 0.85 | 2.24 | 2.949 (9) | 142 |
O2W—H2W1···O1W | 0.85 | 1.99 | 2.822 (7) | 164 |
O2W—H2W2···O3Wii | 0.86 | 1.85 | 2.57 (1) | 141 |
O3W—H3W1···O4iii | 0.86 | 2.19 | 2.817 (6) | 129 |
O3W—H3W2···O4W | 0.88 | 1.78 | 2.37 (1) | 123 |
O4W—H4W2···O2 | 0.88 | 2.05 | 2.693 (8) | 129 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z. |
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