Tetra­aqua­[3-(1H-imidazol-4-yl)-2-(6-{N-[(1H-imid­azol-4-yl)-1-carboxyl­atoethyl]­carbamoyl}-2-pyridyl­carbonyl­amino)­propionato]­nickel(II) pentahydrate

The preparation and crystal structure of the title complex, [Ni(BHISP)(H₂O)₄]·5H₂O, where BHISP^2- is 3-(1H-imidazol-4-yl)-2-(6-{N-[(1H-imidazol-4-yl)-1-carboxyl­atoethyl]­carbam­oyl}-2-pyridyl­carbonyl­amino)­propionate (C₁₉H₁₇N₇O₆), are presented. The Ni^II ion is coordinated by two imidazole N atoms of each histidine arm of the BHISP^2- ligand, and four water mol­ecules complete the octahedral environment of the complex.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.041
• wR factor = 0.114
• Data-to-parameter ratio = 13.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_302  Alert C Anion/Solvent Disorder .......................      17.00 Perc.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: SET4 in CAD-4 EXPRESS; data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai et al., 1996); software used to prepare material for publication: SHELXL97.

Tetraaqua[3-(1H-imidazol-4-yl)-2-(6-{N-[(1H-imidazol-4-yl)-1-carboxylatoethyl]- carbamoyl}-2-pyridylcarbonylamino)propionato]nickel(II) pentahydrate

Crystal data

[Ni(C19H17N7O6)(H2O)4]·5H2O	Z = 2
Mr = 660.25	F(000) = 692
Triclinic, P1	Dx = 1.564 Mg m^−3
a = 9.610 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.313 (2) Å	Cell parameters from 25 reflections
c = 13.455 (3) Å	θ = 9.8–15.3°
α = 80.96 (3)°	µ = 0.78 mm^−1
β = 81.45 (3)°	T = 293 K
γ = 77.78 (3)°	Prismatic, blue
V = 1401.8 (5) Å^3	0.47 × 0.33 × 0.30 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	3865 reflections with I > 2σ(I)'
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.5°, θmin = 2.5°
ω–2θ scans	h = −11→0
Absorption correction: ψ scan (PLATON; Spek, 1990)	k = −13→13
Tmin = 0.688, Tmax = 0.793	l = −16→16
5488 measured reflections	3 standard reflections every 200 reflections
5160 independent reflections	intensity decay: 3.0%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0562P)^2 + 1.1893P] where P = (Fo^2 + 2Fc^2)/3
5160 reflections	(Δ/σ)max < 0.001
388 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.20659 (4)	0.04198 (3)	0.20518 (3)	0.02318 (13)
O1W	0.0678 (2)	0.03222 (19)	0.10603 (16)	0.0329 (5)
H1WA	0.0415	0.0786	0.0533	0.039*
H1WB	0.0465	−0.0281	0.0925	0.039*
O2W	0.2317 (3)	−0.1480 (2)	0.24924 (19)	0.0421 (6)
H2WA	0.2752	−0.1932	0.2119	0.050*
H2WB	0.1664	−0.1807	0.2763	0.050*
O3W	0.3587 (2)	0.0437 (2)	0.30098 (16)	0.0336 (5)
H3WB	0.4118	0.0903	0.2904	0.040*
H3WA	0.4281	−0.0178	0.3060	0.040*
O4W	0.3729 (3)	0.0045 (2)	0.09456 (18)	0.0465 (6)
H4WA	0.4627	0.0036	0.0992	0.056*
H4WB	0.3535	−0.0219	0.0371	0.056*
O21	0.0167 (3)	0.81115 (19)	0.06129 (16)	0.0358 (5)
O22	−0.1696 (3)	0.8328 (2)	0.1808 (2)	0.0500 (7)
O23	0.0294 (2)	0.7149 (2)	0.37584 (17)	0.0360 (5)
O41	−0.4515 (3)	0.1928 (2)	0.24450 (19)	0.0479 (7)
O42	−0.3215 (3)	0.3338 (2)	0.23467 (18)	0.0427 (6)
O43	−0.4645 (3)	0.3401 (2)	0.58953 (18)	0.0418 (6)
N2	−0.2206 (3)	0.5181 (2)	0.45253 (18)	0.0257 (6)
N12	−0.0731 (3)	0.6098 (2)	0.28629 (18)	0.0280 (6)
H12	−0.1424	0.5702	0.2959	0.034*
N16	0.2213 (3)	0.4106 (2)	0.0910 (2)	0.0339 (6)
H16	0.2635	0.4658	0.0583	0.041*
N18	0.1810 (3)	0.2306 (2)	0.15979 (18)	0.0257 (6)
N32	−0.3507 (3)	0.3403 (2)	0.4305 (2)	0.0303 (6)
H32	−0.2883	0.3671	0.3882	0.036*
N36	−0.0760 (3)	0.1328 (3)	0.4573 (2)	0.0360 (7)
H36	−0.0993	0.1716	0.5145	0.043*
N38	0.0450 (3)	0.0621 (2)	0.32151 (18)	0.0257 (6)
C1	−0.1438 (3)	0.5988 (3)	0.4641 (2)	0.0265 (7)
C3	−0.2989 (3)	0.4734 (3)	0.5347 (2)	0.0263 (7)
C4	−0.3058 (3)	0.5085 (3)	0.6295 (2)	0.0322 (7)
H4	−0.3638	0.4769	0.6845	0.039*
C5	−0.2257 (4)	0.5905 (3)	0.6404 (2)	0.0375 (8)
H5	−0.2281	0.6163	0.7030	0.045*
C6	−0.1412 (4)	0.6342 (3)	0.5570 (3)	0.0357 (8)
H6	−0.0824	0.6876	0.5634	0.043*
C11	−0.0549 (3)	0.6485 (3)	0.3706 (2)	0.0270 (7)
C13	−0.0006 (3)	0.6422 (3)	0.1870 (2)	0.0252 (7)
H13	0.1015	0.6341	0.1929	0.030*
C14	−0.0156 (4)	0.5532 (3)	0.1159 (2)	0.0297 (7)
H14A	−0.1145	0.5427	0.1255	0.036*
H14B	0.0048	0.5900	0.0466	0.036*
C15	0.0794 (3)	0.4295 (3)	0.1298 (2)	0.0265 (7)
C17	0.2777 (4)	0.2906 (3)	0.1104 (3)	0.0345 (8)
H17	0.3725	0.2555	0.0912	0.041*
C19	0.0559 (3)	0.3174 (3)	0.1720 (2)	0.0272 (7)
H19	−0.0316	0.3009	0.2045	0.033*
C20	−0.0575 (4)	0.7740 (3)	0.1396 (2)	0.0289 (7)
C31	−0.3790 (3)	0.3786 (3)	0.5207 (2)	0.0273 (7)
C33	−0.4091 (3)	0.2452 (3)	0.3994 (2)	0.0288 (7)
H33	−0.5111	0.2549	0.4255	0.035*
C34	−0.3313 (3)	0.1183 (3)	0.4422 (3)	0.0331 (7)
H34A	−0.3463	0.1100	0.5157	0.040*
H34B	−0.3719	0.0563	0.4207	0.040*
C35	−0.1742 (3)	0.0982 (3)	0.4076 (2)	0.0283 (7)
C37	0.0530 (4)	0.1071 (3)	0.4039 (2)	0.0332 (7)
H37	0.1374	0.1195	0.4229	0.040*
C39	−0.0964 (3)	0.0563 (3)	0.3238 (2)	0.0295 (7)
H39	−0.1337	0.0274	0.2745	0.035*
C40	−0.3939 (3)	0.2593 (3)	0.2830 (2)	0.0304 (7)
O5W	0.3469 (3)	−0.0339 (3)	−0.09530 (19)	0.0531 (7)
H5WA	0.3540	−0.0933	−0.1348	0.064*
H5WB	0.2838	0.0282	−0.1228	0.064*
O6W	−0.3646 (3)	0.5793 (3)	0.2303 (2)	0.0594 (8)
H6WA	−0.3426	0.4874	0.2255	0.071*
H6WB	−0.4073	0.6036	0.2981	0.071*
O7W	−0.5968 (3)	0.1411 (2)	0.6609 (2)	0.0672 (9)
H7WA	−0.5675	0.2165	0.6367	0.081*
H7WB	−0.6733	0.1662	0.7084	0.081*
O8W	−0.2699 (3)	0.3518 (3)	0.0224 (2)	0.0645 (8)
H8WA	−0.2998	0.3369	0.1018	0.077*
H8WB	−0.1775	0.2875	0.0038	0.077*
O9W	0.4315 (12)	−0.2724 (8)	0.1090 (8)	0.082 (3)	0.50
H9WA	0.3851	−0.3125	0.0638	0.099*	0.50
H9WB	0.5152	−0.3180	0.1437	0.099*	0.50
O9W'	0.3887 (11)	−0.3242 (9)	0.1416 (7)	0.077 (3)	0.50
H9WC	0.3430	−0.3634	0.0973	0.092*	0.50
H9WD	0.4705	−0.3709	0.1770	0.092*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0243 (2)	0.0201 (2)	0.0247 (2)	−0.00540 (15)	−0.00122 (15)	−0.00180 (15)
O1W	0.0484 (14)	0.0242 (11)	0.0308 (12)	−0.0130 (10)	−0.0181 (10)	0.0026 (9)
O2W	0.0449 (14)	0.0225 (12)	0.0560 (16)	−0.0075 (11)	0.0019 (12)	−0.0029 (11)
O3W	0.0274 (12)	0.0342 (13)	0.0407 (13)	−0.0097 (10)	−0.0082 (10)	−0.0007 (10)
O4W	0.0297 (13)	0.0721 (18)	0.0404 (14)	−0.0108 (12)	0.0065 (11)	−0.0243 (13)
O21	0.0489 (14)	0.0246 (12)	0.0308 (12)	−0.0107 (11)	0.0005 (11)	0.0060 (9)
O22	0.0496 (16)	0.0318 (14)	0.0557 (16)	0.0049 (12)	0.0083 (13)	0.0026 (12)
O23	0.0413 (14)	0.0358 (13)	0.0365 (13)	−0.0203 (11)	0.0003 (10)	−0.0091 (10)
O41	0.0528 (16)	0.0539 (17)	0.0473 (15)	−0.0253 (14)	−0.0097 (13)	−0.0139 (13)
O42	0.0560 (16)	0.0417 (14)	0.0345 (13)	−0.0236 (13)	0.0030 (11)	−0.0057 (11)
O43	0.0462 (15)	0.0417 (14)	0.0376 (13)	−0.0196 (12)	0.0101 (11)	−0.0045 (11)
N2	0.0289 (14)	0.0254 (13)	0.0248 (13)	−0.0083 (11)	−0.0054 (11)	−0.0027 (10)
N12	0.0369 (15)	0.0247 (13)	0.0248 (13)	−0.0155 (12)	−0.0023 (11)	0.0014 (11)
N16	0.0438 (17)	0.0240 (14)	0.0331 (15)	−0.0153 (13)	0.0037 (13)	0.0029 (11)
N18	0.0308 (14)	0.0204 (13)	0.0260 (13)	−0.0084 (11)	−0.0010 (11)	−0.0011 (10)
N32	0.0288 (14)	0.0325 (15)	0.0312 (15)	−0.0136 (12)	0.0030 (11)	−0.0047 (12)
N36	0.0368 (16)	0.0414 (17)	0.0283 (15)	−0.0002 (13)	−0.0019 (12)	−0.0118 (12)
N38	0.0271 (14)	0.0261 (14)	0.0235 (13)	−0.0069 (11)	−0.0007 (11)	−0.0016 (11)
C1	0.0258 (16)	0.0237 (16)	0.0298 (16)	−0.0027 (13)	−0.0054 (13)	−0.0041 (13)
C3	0.0251 (16)	0.0257 (16)	0.0263 (16)	−0.0019 (13)	−0.0039 (13)	−0.0017 (13)
C4	0.0312 (17)	0.0386 (19)	0.0248 (16)	−0.0049 (15)	−0.0021 (13)	−0.0019 (14)
C5	0.042 (2)	0.047 (2)	0.0263 (17)	−0.0079 (17)	−0.0058 (15)	−0.0136 (15)
C6	0.0377 (19)	0.0382 (19)	0.0372 (19)	−0.0130 (16)	−0.0068 (15)	−0.0132 (15)
C11	0.0324 (17)	0.0206 (15)	0.0292 (17)	−0.0058 (13)	−0.0041 (13)	−0.0055 (13)
C13	0.0307 (17)	0.0204 (15)	0.0246 (15)	−0.0078 (13)	−0.0040 (13)	0.0014 (12)
C14	0.0417 (19)	0.0227 (16)	0.0249 (16)	−0.0071 (14)	−0.0078 (14)	0.0013 (13)
C15	0.0378 (18)	0.0242 (16)	0.0191 (15)	−0.0087 (14)	−0.0042 (13)	−0.0033 (12)
C17	0.0352 (19)	0.0282 (18)	0.0386 (19)	−0.0084 (15)	0.0014 (15)	−0.0020 (14)
C19	0.0321 (17)	0.0234 (16)	0.0267 (16)	−0.0059 (13)	−0.0050 (13)	−0.0026 (13)
C20	0.0376 (19)	0.0188 (15)	0.0313 (17)	−0.0066 (14)	−0.0060 (14)	−0.0029 (13)
C31	0.0262 (16)	0.0259 (16)	0.0273 (16)	−0.0039 (13)	−0.0011 (13)	0.0009 (13)
C33	0.0250 (16)	0.0262 (16)	0.0367 (18)	−0.0100 (13)	0.0012 (13)	−0.0063 (14)
C34	0.0323 (18)	0.0289 (17)	0.0358 (18)	−0.0101 (14)	0.0040 (14)	0.0004 (14)
C35	0.0293 (17)	0.0251 (16)	0.0271 (16)	−0.0034 (13)	0.0001 (13)	0.0010 (13)
C37	0.0293 (18)	0.0332 (18)	0.0361 (19)	−0.0013 (14)	−0.0065 (14)	−0.0052 (15)
C39	0.0303 (17)	0.0325 (18)	0.0272 (16)	−0.0093 (14)	−0.0034 (13)	−0.0044 (13)
C40	0.0263 (17)	0.0280 (17)	0.0373 (18)	−0.0053 (14)	−0.0030 (14)	−0.0058 (14)
O5W	0.0546 (17)	0.0577 (17)	0.0446 (15)	0.0053 (14)	−0.0144 (13)	−0.0132 (13)
O6W	0.0634 (19)	0.0536 (17)	0.0614 (18)	−0.0148 (15)	0.0032 (15)	−0.0136 (14)
O7W	0.0603 (19)	0.0382 (16)	0.091 (2)	−0.0107 (14)	0.0247 (17)	−0.0013 (15)
O8W	0.075 (2)	0.065 (2)	0.0499 (17)	−0.0160 (16)	0.0048 (15)	−0.0045 (14)
O9W	0.101 (8)	0.054 (6)	0.082 (7)	0.012 (5)	−0.014 (6)	−0.015 (5)
O9W'	0.083 (6)	0.082 (7)	0.058 (6)	0.010 (5)	−0.017 (4)	−0.016 (5)

Geometric parameters (Å, º)

Ni1—N38	2.038 (3)	O1W—H1WA	0.8504
Ni1—O4W	2.038 (2)	O1W—H1WB	0.8057
Ni1—O1W	2.051 (2)	O2W—H2WA	0.7852
Ni1—O3W	2.092 (2)	O2W—H2WB	0.8063
Ni1—N18	2.098 (2)	O3W—H3WB	0.7926
Ni1—O2W	2.110 (2)	O3W—H3WA	0.8573
O21—C20	1.250 (4)	O4W—H4WA	0.8724
O22—C20	1.242 (4)	O4W—H4WB	0.9273
O23—C11	1.232 (4)	N12—H12	0.8625
O41—C40	1.234 (4)	N16—H16	0.8471
O42—C40	1.249 (4)	N32—H32	0.8342
O43—C31	1.233 (4)	N36—H36	0.9213
N2—C1	1.329 (4)	C4—H4	0.9300
N2—C3	1.335 (4)	C5—H5	0.9300
N12—C11	1.325 (4)	C6—H6	0.9300
N12—C13	1.443 (4)	C13—H13	0.9800
N16—C17	1.350 (4)	C14—H14A	0.9700
N16—C15	1.370 (4)	C14—H14B	0.9700
N18—C17	1.306 (4)	C17—H17	0.9300
N18—C19	1.388 (4)	C19—H19	0.9300
N32—C31	1.324 (4)	C33—H33	0.9800
N32—C33	1.454 (4)	C34—H34A	0.9700
N36—C37	1.336 (4)	C34—H34B	0.9700
N36—C35	1.384 (4)	C37—H37	0.9300
N38—C37	1.309 (4)	C39—H39	0.9300
N38—C39	1.370 (4)	O5W—H5WA	0.9056
C1—C6	1.376 (4)	O5W—H5WB	0.8960
C1—C11	1.513 (4)	O6W—H6WA	1.0265
C3—C4	1.383 (4)	O6W—H6WB	0.9981
C3—C31	1.495 (4)	O7W—H7WA	0.9479
C4—C5	1.360 (5)	O7W—H7WB	0.9273
C5—C6	1.374 (5)	O8W—H8WA	1.0605
C13—C14	1.533 (4)	O8W—H8WB	1.0475
C13—C20	1.546 (4)	O9W—H9WA	1.0128
C14—C15	1.502 (4)	O9W—H9WB	0.9961
C15—C19	1.356 (4)	O9W—H9WD	1.3510
C33—C40	1.537 (4)	O9W'—H9WA	1.0388
C33—C34	1.538 (4)	O9W'—H9WB	1.2370
C34—C35	1.492 (4)	O9W'—H9WC	0.9938
C35—C39	1.350 (4)	O9W'—H9WD	0.9907
O9W—O9W'	0.820 (10)
N38—Ni1—O4W	174.42 (10)	Ni1—O2W—H2WA	120.0
N38—Ni1—O1W	92.02 (10)	Ni1—O2W—H2WB	123.0
O4W—Ni1—O1W	88.96 (10)	H2WA—O2W—H2WB	103.8
N38—Ni1—O3W	91.20 (10)	Ni1—O3W—H3WB	123.3
O4W—Ni1—O3W	87.63 (10)	Ni1—O3W—H3WA	117.9
O1W—Ni1—O3W	176.13 (9)	H3WB—O3W—H3WA	92.1
N38—Ni1—N18	92.88 (10)	Ni1—O4W—H4WA	125.5
O4W—Ni1—N18	92.62 (11)	Ni1—O4W—H4WB	117.5
O1W—Ni1—N18	89.42 (10)	H4WA—O4W—H4WB	116.7
O3W—Ni1—N18	92.56 (10)	C11—N12—H12	111.8
N38—Ni1—O2W	87.41 (10)	C13—N12—H12	122.6
O4W—Ni1—O2W	87.10 (11)	C17—N16—H16	127.0
O1W—Ni1—O2W	89.99 (10)	C15—N16—H16	124.3
O3W—Ni1—O2W	88.01 (10)	C31—N32—H32	118.9
N18—Ni1—O2W	179.36 (10)	C33—N32—H32	114.9
C1—N2—C3	117.5 (3)	C37—N36—H36	127.4
C11—N12—C13	125.1 (3)	C35—N36—H36	124.6
C17—N16—C15	108.6 (3)	C5—C4—H4	120.8
C17—N18—C19	105.4 (3)	C3—C4—H4	120.8
C17—N18—Ni1	127.3 (2)	C4—C5—H5	120.7
C19—N18—Ni1	127.2 (2)	C6—C5—H5	120.7
C31—N32—C33	125.9 (3)	C5—C6—H6	120.1
C37—N36—C35	107.9 (3)	C1—C6—H6	120.1
C37—N38—C39	105.6 (3)	N12—C13—H13	108.3
C37—N38—Ni1	124.1 (2)	C14—C13—H13	108.3
C39—N38—Ni1	129.1 (2)	C20—C13—H13	108.3
N2—C1—C6	122.1 (3)	C15—C14—H14A	108.4
N2—C1—C11	117.1 (3)	C13—C14—H14A	108.4
C6—C1—C11	120.8 (3)	C15—C14—H14B	108.4
N2—C3—C4	123.4 (3)	C13—C14—H14B	108.4
N2—C3—C31	116.5 (3)	H14A—C14—H14B	107.4
C4—C3—C31	120.0 (3)	N18—C17—H17	124.6
C5—C4—C3	118.4 (3)	N16—C17—H17	124.6
C4—C5—C6	118.7 (3)	C15—C19—H19	124.8
C5—C6—C1	119.7 (3)	N18—C19—H19	124.8
O23—C11—N12	124.8 (3)	N32—C33—H33	108.9
O23—C11—C1	121.4 (3)	C40—C33—H33	108.9
N12—C11—C1	113.7 (3)	C34—C33—H33	108.9
N12—C13—C14	109.4 (2)	C35—C34—H34A	109.3
N12—C13—C20	113.4 (3)	C33—C34—H34A	109.3
C14—C13—C20	109.1 (2)	C35—C34—H34B	109.3
C15—C14—C13	115.6 (3)	C33—C34—H34B	109.3
C19—C15—N16	104.7 (3)	H34A—C34—H34B	107.9
C19—C15—C14	133.7 (3)	N38—C37—H37	124.4
N16—C15—C14	121.6 (3)	N36—C37—H37	124.4
N18—C17—N16	110.8 (3)	C35—C39—H39	124.6
C15—C19—N18	110.4 (3)	N38—C39—H39	124.6
O22—C20—O21	126.1 (3)	H5WA—O5W—H5WB	104.0
O22—C20—C13	119.0 (3)	H6WA—O6W—H6WB	115.9
O21—C20—C13	114.9 (3)	H7WA—O7W—H7WB	100.2
O43—C31—N32	123.6 (3)	H8WA—O8W—H8WB	108.4
O43—C31—C3	121.3 (3)	O9W'—O9W—H9WA	68.1
N32—C31—C3	115.1 (3)	O9W'—O9W—H9WB	85.3
N32—C33—C40	109.0 (2)	H9WA—O9W—H9WB	121.3
N32—C33—C34	110.6 (3)	O9W'—O9W—H9WD	46.8
C40—C33—C34	110.7 (3)	H9WA—O9W—H9WD	98.5
C35—C34—C33	111.8 (3)	H9WB—O9W—H9WD	38.4
C39—C35—N36	104.5 (3)	O9W—O9W'—H9WA	64.8
C39—C35—C34	131.9 (3)	O9W—O9W'—H9WB	53.4
N36—C35—C34	123.4 (3)	H9WA—O9W'—H9WB	100.2
N38—C37—N36	111.2 (3)	O9W—O9W'—H9WC	111.9
C35—C39—N38	110.7 (3)	H9WA—O9W'—H9WC	47.1
O41—C40—O42	125.0 (3)	H9WB—O9W'—H9WC	131.9
O41—C40—C33	116.9 (3)	O9W—O9W'—H9WD	96.0
O42—C40—C33	118.1 (3)	H9WA—O9W'—H9WD	125.5
Ni1—O1W—H1WA	132.4	H9WB—O9W'—H9WD	42.7
Ni1—O1W—H1WB	127.7	H9WC—O9W'—H9WD	120.8
H1WA—O1W—H1WB	96.2
N2—C3—C31—N32	7.0 (4)	C11—N12—C13—C14	163.9 (3)
C3—C31—N32—C33	177.1 (3)	C11—N12—C13—C20	−74.1 (4)
N2—C1—C11—N12	4.2 (4)	C31—N32—C33—C34	−78.0 (4)
C1—C11—N12—C13	−179.4 (3)	C31—N32—C33—C40	160.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O21^i	0.85	1.90	2.748 (3)	177
O1W—H1WB···O21^ii	0.81	2.02	2.817 (3)	173
O2W—H2WA···O9W	0.79	2.04	2.800 (11)	162
O2W—H2WA···O9W′	0.79	1.93	2.708 (11)	170
O2W—H2WB···O23^ii	0.81	2.14	2.923 (3)	166
O3W—H3WB···O41^iii	0.79	1.91	2.691 (3)	171
O3W—H3WA···O7W^iv	0.86	1.96	2.803 (4)	168
O4W—H4WA···O5W^v	0.87	1.92	2.784 (4)	169
O4W—H4WB···O5W	0.93	1.82	2.713 (4)	161
N12—H12···N2	0.86	2.16	2.653 (4)	116
N16—H16···O8W^i	0.85	2.18	2.968 (4)	154
N32—H32···N2	0.83	2.28	2.657 (4)	108
N32—H32···O42	0.83	2.24	2.619 (4)	108
N36—H36···O23^vi	0.92	2.35	3.170 (4)	148
O5W—H5WA···O41^vii	0.91	2.00	2.836 (4)	153
O5W—H5WB···O22^i	0.90	1.85	2.743 (4)	173
O6W—H6WA···O42	1.03	1.69	2.713 (4)	171
O6W—H6WB···O43^viii	1.00	1.90	2.877 (4)	164
O7W—H7WA···O43	0.95	1.86	2.789 (4)	166
O7W—H7WB···O22^viii	0.93	1.96	2.857 (4)	163
O8W—H8WA···O42	1.06	1.76	2.808 (4)	167
O8W—H8WB···O21^i	1.05	1.89	2.920 (4)	167
O9W—H9WA···O8W^vii	1.01	1.88	2.871 (12)	167
O9W—H9WB···O6W^ix	1.00	1.86	2.831 (12)	165
O9W′—H9WC···O8W^vii	0.99	1.83	2.717 (11)	148
O9W′—H9WD···O6W^ix	0.99	1.78	2.752 (11)	166

Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z; (iii) x+1, y, z; (iv) −x, −y, −z+1; (v) −x+1, −y, −z; (vi) −x, −y+1, −z+1; (vii) −x, −y, −z; (viii) −x−1, −y+1, −z+1; (ix) x+1, y−1, z.