Bis[(1-ammonio-ethane-1,1-di-yl)diphospho-nato-κO,O']diaqua-nickel(II) nona-hydrate.

The title compound, [Ni(C(2)H(8)NO(6)P(2))(2)(H(2)O)(2)]·9H(2)O, exhibits a slightly distorted octa-hedral coordination environment around the Ni(II) atom. It contains two mol-ecules of 1-amino--ethyl-idenediphospho-nic acid in the zwitterionic form, coord-inated via O atoms from two phospho-nate groups and creating two six-membered chelate rings. Two water mol-ecules in cis positions complete the coordination environment of the Ni(II) atom. The title compound contains nine partly disordered solvent water mol-ecules, which create a three-dimensional network of strong O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For general background to the use of organic diphospho­nic acids, see: Matczak-Jon & Videnova-Adrabinska (2005 ▶). For applications of transition-metal bis­phospho­nates, see: Eberhardt et al. (2005 ▶). For related structures, see: Li et al. (2007 ▶); Dudko et al. (2009 ▶).

Experimental

Crystal data

[Ni(C2H8NO6P2)2(H2O)2]·9H2O

M = 664.95

Monoclinic,

a = 15.1408 (3) Å

b = 13.1972 (3) Å

c = 12.9344 (3) Å

β = 106.1689 (11)°

V = 2482.27 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.14 mm−1

T = 173 K

0.23 × 0.22 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Bruker, 2005 ▶) T min = 0.778, T max = 0.850

48425 measured reflections

6235 independent reflections

5333 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.072

S = 1.07

6235 reflections

415 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001531X/ez2208sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001531X/ez2208Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C2H8NO6P2)2(H2O)2]·9H2O	F(000) = 1392
Mr = 664.95	Dx = 1.779 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9144 reflections
a = 15.1408 (3) Å	θ = 2.3–28.4°
b = 13.1972 (3) Å	µ = 1.14 mm−1
c = 12.9344 (3) Å	T = 173 K
β = 106.1689 (11)°	Block, light green
V = 2482.27 (9) Å3	0.23 × 0.22 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	6235 independent reflections
Radiation source: fine-focus sealed tube	5333 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 8.33 pixels mm-1	θmax = 28.4°, θmin = 1.4°
φ and ω scans	h = −17→20
Absorption correction: numerical (SADABS; Bruker, 2005)	k = −15→17
Tmin = 0.778, Tmax = 0.850	l = −17→17
48425 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0345P)2 + 1.5506P] where P = (Fo2 + 2Fc2)/3
6235 reflections	(Δ/σ)max = 0.001
415 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	Occ. (<1)
Ni1	0.254825 (15)	0.506019 (16)	0.523912 (16)	0.01040 (6)
P1	0.39949 (3)	0.31363 (3)	0.57666 (3)	0.01121 (10)
P2	0.37259 (3)	0.41840 (3)	0.35969 (3)	0.01008 (9)
P3	0.06502 (3)	0.41352 (3)	0.36142 (3)	0.01021 (9)
P4	0.09045 (3)	0.64384 (3)	0.36384 (3)	0.01202 (10)
C1	0.36922 (12)	0.29690 (12)	0.42905 (13)	0.0115 (3)
C2	0.43105 (13)	0.21769 (14)	0.39811 (14)	0.0168 (4)
H1C	0.4243	0.1528	0.4319	0.025*
H2C	0.4953	0.2400	0.4229	0.025*
H3C	0.4132	0.2096	0.3197	0.025*
C3	0.06373 (12)	0.52864 (13)	0.28050 (13)	0.0119 (3)
C4	−0.02889 (13)	0.53922 (15)	0.19427 (14)	0.0179 (4)
H4C	−0.0284	0.6008	0.1520	0.027*
H5C	−0.0785	0.5436	0.2291	0.027*
H6C	−0.0388	0.4801	0.1466	0.027*
N1	0.27160 (11)	0.25917 (12)	0.39567 (12)	0.0126 (3)
H1N	0.2545 (15)	0.2521 (17)	0.3304 (19)	0.019*
H2N	0.2367 (16)	0.2994 (18)	0.4148 (18)	0.019*
H3N	0.2685 (15)	0.2013 (18)	0.4245 (17)	0.019*
N2	0.13780 (11)	0.51860 (12)	0.22423 (12)	0.0146 (3)
H4N	0.1273 (15)	0.4615 (18)	0.1846 (18)	0.022*
H5N	0.1925 (17)	0.5163 (17)	0.269 (2)	0.022*
H6N	0.1398 (15)	0.5704 (18)	0.1835 (18)	0.022*
O1	0.32986 (8)	0.38339 (9)	0.60142 (9)	0.0134 (2)
O2	0.40603 (9)	0.20946 (9)	0.62466 (9)	0.0160 (3)
O3	0.49780 (9)	0.36086 (10)	0.60780 (10)	0.0170 (3)
H3O	0.5017 (16)	0.4180 (18)	0.6090 (18)	0.020*
O4	0.31223 (9)	0.49330 (9)	0.39539 (10)	0.0134 (3)
O5	0.32244 (9)	0.39486 (10)	0.23893 (10)	0.0153 (3)
H5O	0.3493 (16)	0.3661 (18)	0.2144 (19)	0.018*
O6	0.47117 (8)	0.44797 (9)	0.37730 (10)	0.0159 (3)
O7	0.15774 (8)	0.40580 (9)	0.44333 (9)	0.0129 (2)
O8	0.05982 (9)	0.32515 (10)	0.28082 (10)	0.0168 (3)
H8O	0.0131 (16)	0.2986 (18)	0.2607 (18)	0.020*
O9	−0.01636 (8)	0.41774 (10)	0.40575 (10)	0.0156 (3)
O10	0.18139 (9)	0.62792 (9)	0.44657 (9)	0.0152 (3)
O11	0.08907 (9)	0.73164 (9)	0.28909 (10)	0.0166 (3)
O12	0.00776 (9)	0.65624 (10)	0.41202 (11)	0.0176 (3)
H12O	0.0136 (16)	0.6311 (18)	0.4639 (19)	0.021*
O13	0.35399 (10)	0.60034 (11)	0.61432 (11)	0.0191 (3)
H131	0.4115 (18)	0.5931 (17)	0.6123 (18)	0.023*
H132	0.3421 (16)	0.6536 (19)	0.6076 (19)	0.023*
O14	0.18989 (10)	0.51133 (10)	0.64265 (11)	0.0165 (3)
H141	0.1422 (18)	0.5294 (18)	0.6272 (19)	0.020*
H142	0.2110 (16)	0.5442 (17)	0.6965 (19)	0.020*
O15	0.19397 (11)	0.29225 (11)	0.67872 (11)	0.0218 (3)
H151	0.1539 (18)	0.3253 (19)	0.673 (2)	0.026*
H152	0.2340 (17)	0.3238 (18)	0.6574 (19)	0.026*
O16	0.10537 (12)	0.37339 (13)	0.06297 (12)	0.0288 (3)
H161	0.1308 (18)	0.317 (2)	0.095 (2)	0.035*
H162	0.1417 (19)	0.393 (2)	0.035 (2)	0.035*
O17	0.24192 (11)	0.06113 (11)	0.46573 (12)	0.0243 (3)
H171	0.2308 (18)	0.0144 (19)	0.423 (2)	0.029*
H172	0.2931 (18)	0.0380 (19)	0.510 (2)	0.029*
O18	0.22367 (11)	0.61233 (12)	0.83215 (12)	0.0263 (3)
H181	0.2724 (18)	0.6606 (19)	0.8440 (19)	0.032*
H182	0.1789 (18)	0.652 (2)	0.822 (2)	0.032*
O19	0.55044 (11)	0.07361 (13)	0.64598 (13)	0.0291 (3)
H191	0.5136 (19)	0.118 (2)	0.644 (2)	0.035*
H192	0.5823 (18)	0.0687 (19)	0.711 (2)	0.035*
O20	0.30635 (14)	0.79284 (13)	0.63636 (17)	0.0427 (4)
H201	0.336 (2)	0.851 (2)	0.621 (2)	0.051*
H202	0.332 (2)	0.803 (2)	0.707 (3)	0.051*
O21	0.39921 (12)	−0.05323 (13)	0.55580 (15)	0.0333 (4)
H211	0.447 (2)	−0.024 (2)	0.593 (2)	0.040*
H212	0.4083 (19)	−0.069 (2)	0.493 (2)	0.040*
O22A	0.67316 (15)	0.28256 (16)	0.6372 (3)	0.0332 (10)	0.863 (11)
H221	0.613 (2)	0.307 (2)	0.616 (2)	0.040*
H222	0.7072 (19)	0.321 (2)	0.607 (2)	0.040*
O23A	0.1136 (2)	0.6434 (4)	0.0445 (4)	0.0398 (14)	0.81 (2)
H231	0.068 (2)	0.671 (3)	0.025 (3)	0.048*
H232	0.162 (2)	0.684 (2)	0.063 (2)	0.048*
O22B	0.6571 (14)	0.2621 (15)	0.577 (2)	0.058 (6)*	0.137 (11)
O23B	0.1072 (11)	0.6784 (17)	0.0740 (16)	0.045 (5)*	0.19 (2)

	U11	U22	U33	U12	U13	U23
Ni1	0.00890 (11)	0.01126 (11)	0.01095 (10)	0.00122 (8)	0.00259 (8)	−0.00011 (7)
P1	0.0109 (2)	0.0114 (2)	0.01128 (18)	0.00152 (16)	0.00294 (16)	0.00155 (15)
P2	0.0093 (2)	0.0103 (2)	0.01103 (18)	0.00031 (16)	0.00354 (15)	0.00037 (14)
P3	0.0084 (2)	0.0113 (2)	0.01100 (18)	−0.00023 (16)	0.00281 (15)	−0.00083 (15)
P4	0.0118 (2)	0.0113 (2)	0.01298 (19)	0.00264 (16)	0.00346 (16)	0.00198 (15)
C1	0.0107 (8)	0.0114 (8)	0.0126 (7)	0.0006 (6)	0.0035 (6)	0.0004 (6)
C2	0.0182 (9)	0.0159 (9)	0.0181 (8)	0.0056 (7)	0.0081 (7)	0.0008 (6)
C3	0.0098 (8)	0.0147 (8)	0.0120 (7)	0.0008 (6)	0.0043 (6)	0.0007 (6)
C4	0.0142 (9)	0.0230 (9)	0.0141 (8)	0.0009 (7)	0.0000 (7)	0.0028 (7)
N1	0.0126 (8)	0.0116 (7)	0.0140 (7)	−0.0005 (6)	0.0041 (6)	−0.0004 (6)
N2	0.0133 (8)	0.0173 (8)	0.0143 (7)	0.0009 (6)	0.0059 (6)	0.0019 (6)
O1	0.0137 (6)	0.0150 (6)	0.0122 (5)	0.0035 (5)	0.0045 (5)	0.0013 (4)
O2	0.0192 (7)	0.0135 (6)	0.0161 (6)	0.0021 (5)	0.0062 (5)	0.0039 (5)
O3	0.0121 (6)	0.0152 (6)	0.0219 (6)	−0.0008 (5)	0.0016 (5)	0.0000 (5)
O4	0.0146 (6)	0.0119 (6)	0.0157 (6)	0.0023 (5)	0.0076 (5)	0.0011 (4)
O5	0.0159 (7)	0.0181 (7)	0.0121 (6)	0.0019 (5)	0.0043 (5)	−0.0010 (5)
O6	0.0109 (6)	0.0162 (6)	0.0216 (6)	−0.0006 (5)	0.0063 (5)	0.0002 (5)
O7	0.0108 (6)	0.0111 (6)	0.0152 (6)	0.0000 (5)	0.0008 (5)	0.0004 (4)
O8	0.0140 (7)	0.0168 (6)	0.0201 (6)	−0.0043 (5)	0.0056 (5)	−0.0069 (5)
O9	0.0106 (6)	0.0205 (6)	0.0175 (6)	0.0024 (5)	0.0067 (5)	0.0021 (5)
O10	0.0153 (6)	0.0120 (6)	0.0163 (6)	0.0010 (5)	0.0010 (5)	0.0004 (4)
O11	0.0160 (7)	0.0148 (6)	0.0191 (6)	0.0028 (5)	0.0053 (5)	0.0064 (5)
O12	0.0185 (7)	0.0195 (7)	0.0175 (6)	0.0064 (5)	0.0095 (5)	0.0050 (5)
O13	0.0123 (7)	0.0156 (6)	0.0281 (7)	0.0001 (5)	0.0035 (5)	−0.0060 (5)
O14	0.0121 (7)	0.0230 (7)	0.0145 (6)	0.0048 (5)	0.0035 (5)	−0.0009 (5)
O15	0.0212 (8)	0.0214 (7)	0.0235 (7)	0.0042 (6)	0.0076 (6)	0.0070 (5)
O16	0.0346 (9)	0.0312 (8)	0.0223 (7)	0.0067 (7)	0.0107 (6)	0.0034 (6)
O17	0.0247 (8)	0.0186 (7)	0.0265 (7)	−0.0006 (6)	0.0018 (6)	0.0005 (6)
O18	0.0244 (8)	0.0219 (7)	0.0317 (8)	0.0003 (6)	0.0061 (6)	−0.0026 (6)
O19	0.0262 (9)	0.0312 (9)	0.0286 (8)	0.0084 (7)	0.0058 (7)	−0.0019 (6)
O20	0.0493 (12)	0.0245 (9)	0.0553 (11)	−0.0003 (8)	0.0161 (9)	−0.0062 (8)
O21	0.0259 (9)	0.0301 (9)	0.0413 (9)	0.0024 (7)	0.0051 (7)	−0.0056 (7)
O22A	0.0208 (12)	0.0242 (11)	0.058 (2)	0.0042 (8)	0.0156 (10)	0.0154 (10)
O23A	0.0491 (18)	0.038 (2)	0.0339 (18)	0.0057 (12)	0.0146 (12)	0.0157 (15)

Ni1—O1	2.0689 (12)	N1—H3N	0.86 (2)
Ni1—O4	2.0861 (13)	N2—H4N	0.90 (2)
Ni1—O7	2.0355 (12)	N2—H5N	0.87 (2)
Ni1—O10	2.0508 (12)	N2—H6N	0.87 (2)
Ni1—O13	2.0477 (13)	O3—H3O	0.76 (2)
Ni1—O14	2.0424 (14)	O5—H5O	0.69 (2)
P1—O1	1.4999 (13)	O8—H8O	0.77 (2)
P1—O2	1.5003 (12)	O12—H12O	0.73 (2)
P1—O3	1.5596 (14)	O13—H131	0.88 (3)
P1—C1	1.8484 (16)	O13—H132	0.72 (2)
P2—O6	1.4976 (13)	O14—H141	0.73 (2)
P2—O4	1.5035 (13)	O14—H142	0.81 (2)
P2—O5	1.5660 (13)	O15—H151	0.73 (3)
P2—C1	1.8449 (17)	O15—H152	0.84 (3)
P3—O9	1.4978 (13)	O16—H161	0.88 (3)
P3—O7	1.5085 (12)	O16—H162	0.78 (3)
P3—O8	1.5515 (13)	O17—H171	0.81 (3)
P3—C3	1.8419 (17)	O17—H172	0.88 (3)
P4—O10	1.5048 (12)	O18—H181	0.95 (3)
P4—O11	1.5056 (12)	O18—H182	0.83 (3)
P4—O12	1.5547 (14)	O19—H191	0.81 (3)
P4—C3	1.8423 (17)	O19—H192	0.85 (3)
C1—N1	1.505 (2)	O20—H201	0.94 (3)
C1—C2	1.529 (2)	O20—H202	0.90 (3)
C2—H1C	0.9800	O21—H211	0.85 (3)
C2—H2C	0.9800	O21—H212	0.88 (3)
C2—H3C	0.9800	O22A—H221	0.94 (3)
C3—N2	1.503 (2)	O22A—H222	0.89 (3)
C3—C4	1.536 (2)	O23A—H231	0.76 (3)
C4—H4C	0.9800	O23A—H232	0.89 (3)
C4—H5C	0.9800	O22B—H221	1.12 (3)
C4—H6C	0.9800	O22B—H222	1.08 (3)
N1—H1N	0.82 (2)	O23B—H231	0.75 (3)
N1—H2N	0.83 (2)	O23B—H232	0.88 (3)
O1—Ni1—O4	91.65 (5)	H2C—C2—H3C	109.5
O7—Ni1—O10	92.51 (5)	N2—C3—C4	108.05 (14)
O14—Ni1—O13	88.83 (6)	N2—C3—P3	108.13 (11)
O7—Ni1—O14	88.69 (5)	C4—C3—P3	110.53 (12)
O7—Ni1—O13	175.95 (5)	N2—C3—P4	106.51 (12)
O14—Ni1—O10	91.76 (5)	C4—C3—P4	110.93 (12)
O13—Ni1—O10	90.77 (5)	P3—C3—P4	112.48 (9)
O7—Ni1—O1	87.74 (5)	C3—C4—H4C	109.5
O14—Ni1—O1	88.67 (5)	C3—C4—H5C	109.5
O13—Ni1—O1	88.99 (5)	H4C—C4—H5C	109.5
O10—Ni1—O1	179.50 (5)	C3—C4—H6C	109.5
O7—Ni1—O4	86.64 (5)	H4C—C4—H6C	109.5
O14—Ni1—O4	175.30 (5)	H5C—C4—H6C	109.5
O13—Ni1—O4	95.86 (5)	C1—N1—H1N	109.7 (16)
O10—Ni1—O4	87.94 (5)	C1—N1—H2N	110.9 (15)
O1—P1—O2	116.32 (7)	H1N—N1—H2N	110 (2)
O1—P1—O3	112.12 (7)	C1—N1—H3N	109.8 (14)
O2—P1—O3	108.12 (7)	H1N—N1—H3N	108 (2)
O1—P1—C1	107.88 (7)	H2N—N1—H3N	109 (2)
O2—P1—C1	106.67 (7)	C3—N2—H4N	108.2 (15)
O3—P1—C1	105.00 (8)	C3—N2—H5N	112.4 (16)
O6—P2—O4	116.57 (7)	H4N—N2—H5N	109 (2)
O6—P2—O5	112.91 (8)	C3—N2—H6N	112.4 (15)
O4—P2—O5	105.62 (7)	H4N—N2—H6N	110 (2)
O6—P2—C1	108.30 (8)	H5N—N2—H6N	104 (2)
O4—P2—C1	108.70 (8)	P1—O1—Ni1	134.46 (7)
O5—P2—C1	103.96 (7)	P1—O3—H3O	117.9 (18)
O9—P3—O7	115.95 (7)	P2—O4—Ni1	136.17 (7)
O9—P3—O8	113.07 (8)	P2—O5—H5O	112.4 (19)
O7—P3—O8	106.51 (7)	P3—O7—Ni1	135.55 (7)
O9—P3—C3	107.89 (8)	P3—O8—H8O	116.2 (18)
O7—P3—C3	108.38 (7)	P4—O10—Ni1	136.12 (8)
O8—P3—C3	104.34 (7)	P4—O12—H12O	114.5 (19)
O10—P4—O11	114.22 (7)	Ni1—O13—H131	119.3 (15)
O10—P4—O12	114.15 (7)	Ni1—O13—H132	113.7 (19)
O11—P4—O12	107.92 (7)	H131—O13—H132	108 (2)
O10—P4—C3	108.02 (7)	Ni1—O14—H141	116.7 (19)
O11—P4—C3	107.33 (7)	Ni1—O14—H142	120.6 (17)
O12—P4—C3	104.55 (8)	H141—O14—H142	101 (2)
N1—C1—C2	108.83 (14)	H151—O15—H152	109 (3)
N1—C1—P2	107.83 (11)	H161—O16—H162	102 (3)
C2—C1—P2	111.41 (12)	H171—O17—H172	99 (2)
N1—C1—P1	106.09 (11)	H181—O18—H182	100 (2)
C2—C1—P1	110.99 (11)	H191—O19—H192	106 (3)
P2—C1—P1	111.47 (9)	H201—O20—H202	90 (2)
C1—C2—H1C	109.5	H211—O21—H212	108 (3)
C1—C2—H2C	109.5	H221—O22A—H222	108 (2)
H1C—C2—H2C	109.5	H231—O23A—H232	115 (3)
C1—C2—H3C	109.5	H221—O22B—H222	85 (3)
H1C—C2—H3C	109.5	H231—O23B—H232	117 (4)
O6—P2—C1—N1	−170.58 (11)	O12—P4—C3—C4	57.74 (14)
O4—P2—C1—N1	61.89 (12)	O10—P4—C3—P3	55.30 (11)
O5—P2—C1—N1	−50.27 (13)	O11—P4—C3—P3	178.91 (9)
O6—P2—C1—C2	−51.23 (13)	O12—P4—C3—P3	−66.64 (10)
O4—P2—C1—C2	−178.76 (11)	O2—P1—O1—Ni1	−153.15 (9)
O5—P2—C1—C2	69.08 (13)	O3—P1—O1—Ni1	81.70 (11)
O6—P2—C1—P1	73.36 (10)	C1—P1—O1—Ni1	−33.43 (12)
O4—P2—C1—P1	−54.17 (11)	O7—Ni1—O1—P1	87.56 (11)
O5—P2—C1—P1	−166.33 (9)	O14—Ni1—O1—P1	176.31 (11)
O1—P1—C1—N1	−55.84 (12)	O13—Ni1—O1—P1	−94.84 (11)
O2—P1—C1—N1	69.81 (12)	O4—Ni1—O1—P1	1.00 (11)
O3—P1—C1—N1	−175.58 (11)	O6—P2—O4—Ni1	−104.40 (11)
O1—P1—C1—C2	−173.91 (12)	O5—P2—O4—Ni1	129.32 (11)
O2—P1—C1—C2	−48.25 (14)	C1—P2—O4—Ni1	18.27 (13)
O3—P1—C1—C2	66.35 (14)	O7—Ni1—O4—P2	−79.32 (11)
O1—P1—C1—P2	61.27 (11)	O13—Ni1—O4—P2	97.48 (11)
O2—P1—C1—P2	−173.07 (8)	O10—Ni1—O4—P2	−171.96 (11)
O3—P1—C1—P2	−58.47 (11)	O1—Ni1—O4—P2	8.33 (11)
O9—P3—C3—N2	−172.77 (11)	O9—P3—O7—Ni1	−91.92 (12)
O7—P3—C3—N2	60.95 (12)	O8—P3—O7—Ni1	141.28 (10)
O8—P3—C3—N2	−52.26 (12)	C3—P3—O7—Ni1	29.52 (13)
O9—P3—C3—C4	−54.68 (14)	O14—Ni1—O7—P3	89.45 (11)
O7—P3—C3—C4	179.03 (12)	O10—Ni1—O7—P3	−2.25 (11)
O8—P3—C3—C4	65.82 (14)	O1—Ni1—O7—P3	178.18 (11)
O9—P3—C3—P4	69.91 (10)	O4—Ni1—O7—P3	−90.04 (11)
O7—P3—C3—P4	−56.38 (11)	O11—P4—O10—Ni1	−146.97 (10)
O8—P3—C3—P4	−169.59 (9)	O12—P4—O10—Ni1	88.17 (12)
O10—P4—C3—N2	−62.98 (12)	C3—P4—O10—Ni1	−27.64 (13)
O11—P4—C3—N2	60.62 (12)	O7—Ni1—O10—P4	1.17 (12)
O12—P4—C3—N2	175.08 (10)	O14—Ni1—O10—P4	−87.60 (12)
O10—P4—C3—C4	179.67 (12)	O13—Ni1—O10—P4	−176.46 (12)
O11—P4—C3—C4	−56.72 (14)	O4—Ni1—O10—P4	87.71 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O15i	0.82 (2)	2.01 (2)	2.807 (2)	166 (2)
N1—H2N···O7	0.83 (2)	1.95 (2)	2.773 (2)	172 (2)
N1—H3N···O17	0.86 (2)	2.00 (2)	2.843 (2)	169 (2)
N2—H4N···O16	0.90 (2)	1.91 (2)	2.774 (2)	160 (2)
N2—H5N···O4	0.87 (2)	2.10 (3)	2.955 (2)	169 (2)
N2—H6N···O23A	0.87 (2)	1.98 (2)	2.789 (3)	154 (2)
O3—H3O···O6ii	0.76 (2)	1.81 (2)	2.5637 (18)	172 (2)
O5—H5O···O2i	0.69 (2)	1.91 (2)	2.5930 (18)	170 (3)
O8—H8O···O11iii	0.77 (2)	1.74 (2)	2.5075 (18)	176 (3)
O12—H12O···O9iv	0.73 (2)	1.79 (2)	2.5209 (18)	172 (3)
O13—H131···O6ii	0.88 (3)	1.83 (3)	2.696 (2)	167 (2)
O13—H132···O20	0.72 (2)	1.98 (3)	2.678 (2)	162 (3)
O14—H141···O9iv	0.73 (2)	1.96 (3)	2.6936 (19)	176 (3)
O14—H142···O18	0.81 (2)	1.93 (2)	2.711 (2)	162 (2)
O15—H151···O12iv	0.73 (3)	2.40 (3)	3.029 (2)	145 (2)
O15—H152···O1	0.84 (3)	1.96 (3)	2.797 (2)	174 (2)
O16—H161···O15i	0.88 (3)	1.90 (3)	2.775 (2)	172 (2)
O16—H162···O17i	0.78 (3)	2.06 (3)	2.838 (2)	177 (3)
O17—H171···O18i	0.81 (3)	2.03 (3)	2.835 (2)	170 (3)
O17—H172···O21	0.88 (3)	1.96 (3)	2.786 (2)	155 (2)
O18—H181···O22Av	0.95 (3)	1.79 (3)	2.702 (2)	158 (2)
O18—H182···O11vi	0.83 (3)	2.02 (3)	2.841 (2)	168 (2)
O19—H191···O2	0.81 (3)	1.98 (3)	2.781 (2)	169 (3)
O19—H192···O13vii	0.85 (3)	2.23 (3)	3.055 (2)	163 (2)
O20—H201···O21viii	0.94 (3)	1.91 (3)	2.829 (3)	164 (3)
O20—H202···O22Av	0.90 (3)	2.05 (3)	2.861 (4)	149 (3)
O21—H211···O19	0.85 (3)	1.99 (3)	2.814 (2)	163 (3)
O21—H212···O19ix	0.88 (3)	2.06 (3)	2.928 (3)	166 (3)
O22A—H221···O3	0.94 (3)	1.86 (3)	2.775 (2)	167 (3)
O22A—H222···O10ii	0.89 (3)	2.10 (3)	2.958 (3)	161 (2)
O23A—H231···O16x	0.76 (3)	2.62 (3)	3.225 (4)	139 (3)
O23A—H232···O20xi	0.89 (3)	2.14 (3)	2.951 (4)	150 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O15i	0.82 (2)	2.01 (2)	2.807 (2)	166 (2)
N1—H2N⋯O7	0.83 (2)	1.95 (2)	2.773 (2)	172 (2)
N1—H3N⋯O17	0.86 (2)	2.00 (2)	2.843 (2)	169 (2)
N2—H4N⋯O16	0.90 (2)	1.91 (2)	2.774 (2)	160 (2)
N2—H5N⋯O4	0.87 (2)	2.10 (3)	2.955 (2)	169 (2)
N2—H6N⋯O23A	0.87 (2)	1.98 (2)	2.789 (3)	154 (2)
O3—H3O⋯O6ii	0.76 (2)	1.81 (2)	2.5637 (18)	172 (2)
O5—H5O⋯O2i	0.69 (2)	1.91 (2)	2.5930 (18)	170 (3)
O8—H8O⋯O11iii	0.77 (2)	1.74 (2)	2.5075 (18)	176 (3)
O12—H12O⋯O9iv	0.73 (2)	1.79 (2)	2.5209 (18)	172 (3)
O13—H131⋯O6ii	0.88 (3)	1.83 (3)	2.696 (2)	167 (2)
O13—H132⋯O20	0.72 (2)	1.98 (3)	2.678 (2)	162 (3)
O14—H141⋯O9iv	0.73 (2)	1.96 (3)	2.6936 (19)	176 (3)
O14—H142⋯O18	0.81 (2)	1.93 (2)	2.711 (2)	162 (2)
O15—H151⋯O12iv	0.73 (3)	2.40 (3)	3.029 (2)	145 (2)
O15—H152⋯O1	0.84 (3)	1.96 (3)	2.797 (2)	174 (2)
O16—H161⋯O15i	0.88 (3)	1.90 (3)	2.775 (2)	172 (2)
O16—H162⋯O17i	0.78 (3)	2.06 (3)	2.838 (2)	177 (3)
O17—H171⋯O18i	0.81 (3)	2.03 (3)	2.835 (2)	170 (3)
O17—H172⋯O21	0.88 (3)	1.96 (3)	2.786 (2)	155 (2)
O18—H181⋯O22Av	0.95 (3)	1.79 (3)	2.702 (2)	158 (2)
O18—H182⋯O11vi	0.83 (3)	2.02 (3)	2.841 (2)	168 (2)
O19—H191⋯O2	0.81 (3)	1.98 (3)	2.781 (2)	169 (3)
O19—H192⋯O13vii	0.85 (3)	2.23 (3)	3.055 (2)	163 (2)
O20—H201⋯O21viii	0.94 (3)	1.91 (3)	2.829 (3)	164 (3)
O20—H202⋯O22Av	0.90 (3)	2.05 (3)	2.861 (4)	149 (3)
O21—H211⋯O19	0.85 (3)	1.99 (3)	2.814 (2)	163 (3)
O21—H212⋯O19ix	0.88 (3)	2.06 (3)	2.928 (3)	166 (3)
O22A—H221⋯O3	0.94 (3)	1.86 (3)	2.775 (2)	167 (3)
O22A—H222⋯O10ii	0.89 (3)	2.10 (3)	2.958 (3)	161 (2)
O23A—H231⋯O16x	0.76 (3)	2.62 (3)	3.225 (4)	139 (3)
O23A—H232⋯O20xi	0.89 (3)	2.14 (3)	2.951 (4)	150 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) ; (xi) .