Nickel alendronate.

The title compound {sys-tematic name: bis(μ(2)-dihydrogen 4-aza-niumyl-1-hy-droxy-butane-1,1-di-phos-pho-n-ato)bis-[aqua-(dihydrogen 4-aza-nium-yl-1-hy-droxy-butane-1,1-diphospho-n-ato)nickel(II)] dihydrate}, [Ni(2)(C(4)H(12)NO(7)P(2))(4)(H(2)O)(2)]·2H(2)O, was synthesiized under hydro-thermal conditions. Its structure is isotypic with the Co(II) analogue. The crystal structure is built up from centrosymmetric dinuclear complex mol-ecules and the structure is reinforced by a net of inter-molecular O-H⋯O and N-H⋯O hydrogen bonds. One water mol-ecule is bound to the Ni(II) atom in the octahedral coordination sphere, while the second is part of the inter-molecular hydrogen-bond system.

Related literature

For the isotypic CoII compound, see: Man et al. (2006 ▶). For the structures and therapeutic properties of bis­phospho­nates, see: Russell (2011 ▶). For zinc alendronate, see: Dufau et al. (1995 ▶).

Experimental

Crystal data

[Ni2(C4H12NO7P2)4(H2O)2]·2H2O

M = 1181.83

Monoclinic,

a = 12.5042 (3) Å

b = 13.5214 (2) Å

c = 12.4538 (3) Å

β = 109.667 (4)°

V = 1982.78 (9) Å3

Z = 2

Mo Kα radiation

μ = 1.39 mm−1

T = 297 K

0.33 × 0.29 × 0.16 mm

Data collection

Oxford Diffraction KM-4-CCD Sapphire2 diffractometer

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction 2010 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.747, T max = 0.854

20727 measured reflections

3522 independent reflections

3237 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.124

S = 1.07

3522 reflections

298 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.44 e Å−3

Δρmin = −0.67 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), Mercury, publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022532/zj2074sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022532/zj2074Isup2.hkl

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

[Ni2(C4H12NO7P2)4(H2O)2]·2H2O	F(000) = 1224
Mr = 1181.83	Dx = 1.98 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16141 reflections
a = 12.5042 (3) Å	θ = 2.3–28.8°
b = 13.5214 (2) Å	µ = 1.39 mm−1
c = 12.4538 (3) Å	T = 297 K
β = 109.667 (4)°	Block, green
V = 1982.78 (9) Å3	0.33 × 0.29 × 0.16 mm
Z = 2

Oxford Diffraction KM-4-CCD Sapphire2 diffractometer	3522 independent reflections
Graphite monochromator	3237 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm-1	Rint = 0.026
ω scans	θmax = 25.1°, θmin = 2.3°
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction 2010), based on expressions derived by Clark & Reid (1995)]	h = −14→14
Tmin = 0.747, Tmax = 0.854	k = −16→16
20727 measured reflections	l = −14→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0687P)2 + 6.2695P] where P = (Fo2 + 2Fc2)/3
3522 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 2.44 e Å−3
6 restraints	Δρmin = −0.67 e Å−3

Experimental. Absorption correction: CrysAlisPro, Oxford Diffraction 2010, Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid 1995.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.69424 (4)	0.54490 (3)	0.47489 (4)	0.01836 (16)
P1	0.90380 (8)	0.39706 (7)	0.61692 (8)	0.0182 (2)
P2	0.93083 (8)	0.61463 (7)	0.67849 (8)	0.0198 (2)
P3	0.48228 (9)	0.27678 (8)	0.55326 (9)	0.0240 (2)
P4	0.45576 (8)	0.41194 (7)	0.34777 (8)	0.0172 (2)
N1	1.1817 (3)	0.2965 (3)	1.0790 (3)	0.0287 (8)
H1NA	1.2515	0.2964	1.1300	0.043*
H1NB	1.1698	0.2403	1.0396	0.043*
H1NC	1.1313	0.3020	1.1149	0.043*
N2	0.7320 (3)	0.3093 (4)	0.2984 (4)	0.0491 (11)
H2NA	0.7813	0.3066	0.2610	0.074*
H2NB	0.7470	0.3618	0.3441	0.074*
H2C	0.6618	0.3140	0.2487	0.074*
O1	0.7949 (2)	0.4259 (2)	0.5266 (2)	0.0250 (6)
O2	0.8834 (2)	0.2960 (2)	0.6677 (2)	0.0246 (6)
H2	0.9390	0.2603	0.6781	0.037*
O3	1.0060 (2)	0.3913 (2)	0.5783 (2)	0.0254 (6)
O4	0.8202 (2)	0.6342 (2)	0.5835 (2)	0.0240 (6)
O5	0.9503 (2)	0.6825 (2)	0.7794 (2)	0.0277 (6)
O6	1.0338 (2)	0.6234 (2)	0.6349 (2)	0.0270 (6)
H6	1.0115	0.6177	0.5653	0.040*
O7	0.3862 (2)	0.3254 (2)	0.5773 (2)	0.0240 (6)
O8	0.5022 (3)	0.1702 (2)	0.5902 (3)	0.0340 (7)
O9	0.5971 (2)	0.3324 (2)	0.6132 (2)	0.0301 (6)
H9	0.5896	0.3911	0.5960	0.045*
O10	0.5735 (2)	0.4502 (2)	0.3740 (2)	0.0244 (6)
O11	0.3940 (2)	0.4038 (2)	0.2154 (2)	0.0249 (6)
H11	0.4364	0.3770	0.1863	0.037*
O12	0.3763 (2)	0.47229 (19)	0.3918 (2)	0.0212 (6)
O13	0.8408 (2)	0.4841 (2)	0.7805 (2)	0.0244 (6)
H13	0.7813	0.5021	0.7324	0.037*
O14	0.3381 (2)	0.2459 (2)	0.3447 (3)	0.0320 (7)
H14	0.3055	0.2448	0.3918	0.048*
O15	0.7615 (3)	0.5602 (3)	0.3433 (3)	0.0350 (7)
C1	0.9316 (3)	0.4880 (3)	0.7328 (3)	0.0203 (8)
C2	1.0451 (3)	0.4727 (3)	0.8315 (3)	0.0257 (8)
H2A	1.1049	0.4653	0.7987	0.031*
H2B	1.0612	0.5324	0.8773	0.031*
C3	1.0521 (3)	0.3859 (3)	0.9103 (4)	0.0299 (9)
H3A	0.9952	0.3928	0.9469	0.036*
H3B	1.0372	0.3249	0.8667	0.036*
C4	1.1690 (4)	0.3818 (3)	0.9998 (3)	0.0304 (9)
H4A	1.2255	0.3765	0.9624	0.037*
H4B	1.1830	0.4428	1.0433	0.037*
C5	0.4540 (3)	0.2832 (3)	0.3985 (3)	0.0243 (8)
C6	0.5333 (3)	0.2156 (3)	0.3597 (3)	0.0271 (9)
H6A	0.5072	0.1479	0.3587	0.033*
H6B	0.5261	0.2331	0.2820	0.033*
C7	0.6591 (4)	0.2194 (4)	0.4324 (4)	0.0369 (10)
H7A	0.6723	0.2793	0.4779	0.044*
H7B	0.6755	0.1638	0.4845	0.044*
C8	0.7420 (4)	0.2174 (4)	0.3681 (5)	0.0463 (13)
H8A	0.8187	0.2119	0.4217	0.056*
H8B	0.7271	0.1601	0.3184	0.056*
H15A	0.829 (2)	0.577 (5)	0.357 (5)	0.069*
H15B	0.732 (4)	0.584 (5)	0.280 (3)	0.069*
O16	0.6399 (6)	0.5061 (6)	0.1101 (7)	0.116 (2)
H16A	0.584 (8)	0.532 (8)	0.054 (8)	0.175*
H16B	0.605 (9)	0.448 (4)	0.102 (11)	0.175*

	U11	U22	U33	U12	U13	U23
Ni1	0.0144 (3)	0.0229 (3)	0.0179 (3)	0.00050 (18)	0.00562 (19)	−0.00056 (18)
P1	0.0149 (5)	0.0217 (5)	0.0171 (5)	0.0014 (4)	0.0041 (4)	−0.0012 (4)
P2	0.0161 (5)	0.0231 (5)	0.0200 (5)	−0.0026 (4)	0.0058 (4)	−0.0022 (4)
P3	0.0248 (5)	0.0255 (5)	0.0238 (5)	0.0026 (4)	0.0110 (4)	0.0032 (4)
P4	0.0159 (5)	0.0212 (5)	0.0151 (5)	0.0002 (4)	0.0059 (4)	−0.0006 (3)
N1	0.0223 (17)	0.039 (2)	0.0218 (17)	0.0053 (15)	0.0038 (14)	0.0006 (15)
N2	0.033 (2)	0.070 (3)	0.049 (3)	−0.013 (2)	0.0197 (19)	−0.004 (2)
O1	0.0211 (14)	0.0250 (14)	0.0234 (14)	0.0036 (11)	0.0003 (11)	−0.0042 (11)
O2	0.0201 (13)	0.0247 (14)	0.0289 (14)	0.0018 (11)	0.0079 (12)	0.0019 (11)
O3	0.0195 (13)	0.0352 (16)	0.0228 (14)	0.0004 (11)	0.0090 (11)	−0.0017 (12)
O4	0.0188 (13)	0.0249 (14)	0.0265 (14)	−0.0006 (11)	0.0052 (11)	0.0003 (11)
O5	0.0279 (14)	0.0288 (15)	0.0289 (15)	−0.0080 (12)	0.0128 (12)	−0.0084 (12)
O6	0.0199 (14)	0.0383 (17)	0.0236 (14)	−0.0073 (12)	0.0084 (11)	−0.0020 (13)
O7	0.0228 (14)	0.0291 (15)	0.0216 (13)	0.0060 (11)	0.0093 (11)	0.0047 (11)
O8	0.0457 (18)	0.0267 (16)	0.0394 (17)	0.0087 (13)	0.0271 (15)	0.0096 (13)
O9	0.0259 (15)	0.0345 (16)	0.0280 (15)	0.0012 (12)	0.0063 (12)	0.0035 (13)
O10	0.0162 (13)	0.0342 (16)	0.0228 (14)	−0.0026 (11)	0.0067 (11)	−0.0059 (11)
O11	0.0189 (13)	0.0356 (16)	0.0199 (13)	0.0009 (11)	0.0063 (11)	−0.0044 (11)
O12	0.0197 (13)	0.0259 (14)	0.0203 (13)	0.0014 (11)	0.0096 (11)	−0.0012 (11)
O13	0.0178 (13)	0.0358 (16)	0.0216 (13)	−0.0002 (12)	0.0093 (11)	0.0016 (12)
O14	0.0263 (15)	0.0354 (16)	0.0338 (16)	−0.0070 (13)	0.0092 (13)	−0.0078 (13)
O15	0.0235 (15)	0.056 (2)	0.0284 (16)	−0.0013 (14)	0.0128 (13)	0.0013 (14)
C1	0.0149 (17)	0.0248 (19)	0.0218 (18)	−0.0012 (15)	0.0070 (15)	−0.0015 (15)
C2	0.0184 (19)	0.035 (2)	0.0205 (19)	−0.0012 (16)	0.0025 (15)	−0.0009 (16)
C3	0.022 (2)	0.034 (2)	0.027 (2)	−0.0007 (17)	0.0001 (17)	0.0004 (17)
C4	0.027 (2)	0.038 (2)	0.0219 (19)	−0.0021 (18)	0.0030 (17)	0.0015 (17)
C5	0.024 (2)	0.025 (2)	0.0231 (19)	−0.0009 (16)	0.0079 (16)	0.0001 (16)
C6	0.029 (2)	0.027 (2)	0.027 (2)	0.0000 (17)	0.0113 (17)	−0.0069 (16)
C7	0.032 (2)	0.043 (3)	0.037 (2)	0.004 (2)	0.013 (2)	0.000 (2)
C8	0.029 (2)	0.056 (3)	0.052 (3)	0.011 (2)	0.012 (2)	−0.014 (3)
O16	0.117 (5)	0.110 (5)	0.128 (6)	−0.028 (4)	0.048 (4)	−0.009 (4)

Ni1—O1	2.011 (3)	O7—Ni1i	2.017 (3)
Ni1—O7i	2.017 (3)	O9—H9	0.8200
Ni1—O10	2.054 (3)	O11—H11	0.8200
Ni1—O4	2.082 (3)	O12—Ni1i	2.139 (3)
Ni1—O15	2.089 (3)	O13—C1	1.449 (4)
Ni1—O12i	2.139 (3)	O13—H13	0.8200
P1—O1	1.497 (3)	O14—C5	1.466 (5)
P1—O3	1.511 (3)	O14—H14	0.8200
P1—O2	1.563 (3)	O15—O16	2.882 (8)
P1—C1	1.838 (4)	O15—H15A	0.83 (2)
P2—O5	1.508 (3)	O15—H15B	0.82 (2)
P2—O4	1.510 (3)	C1—C2	1.547 (5)
P2—O6	1.562 (3)	C2—C3	1.513 (6)
P2—C1	1.839 (4)	C2—H2A	0.9700
P3—O7	1.486 (3)	C2—H2B	0.9700
P3—O8	1.507 (3)	C3—C4	1.512 (5)
P3—O9	1.570 (3)	C3—H3A	0.9700
P3—C5	1.841 (4)	C3—H3B	0.9700
P4—O10	1.490 (3)	C4—H4A	0.9700
P4—O12	1.523 (3)	C4—H4B	0.9700
P4—O11	1.571 (3)	C5—C6	1.541 (5)
P4—C5	1.855 (4)	C6—C7	1.529 (6)
N1—C4	1.491 (6)	C6—H6A	0.9700
N1—H1NA	0.8900	C6—H6B	0.9700
N1—H1NB	0.8900	C7—C8	1.508 (6)
N1—H1NC	0.8900	C7—H7A	0.9700
N2—C8	1.496 (7)	C7—H7B	0.9700
N2—H2NA	0.8900	C8—H8A	0.9700
N2—H2NB	0.8900	C8—H8B	0.9700
N2—H2C	0.8900	O16—H16A	0.88 (2)
O2—H2	0.8200	O16—H16B	0.88 (2)
O6—H6	0.8200
O1—Ni1—O7i	171.66 (11)	P4—O12—Ni1i	135.27 (16)
O1—Ni1—O10	87.07 (11)	C1—O13—H13	109.5
O7i—Ni1—O10	99.26 (11)	C5—O14—H14	109.5
O1—Ni1—O4	90.06 (11)	Ni1—O15—O16	123.4 (2)
O7i—Ni1—O4	83.75 (11)	Ni1—O15—H15A	121 (4)
O10—Ni1—O4	176.74 (11)	O16—O15—H15A	115 (4)
O1—Ni1—O15	87.52 (13)	Ni1—O15—H15B	129 (4)
O7i—Ni1—O15	87.12 (12)	H15A—O15—H15B	101 (3)
O10—Ni1—O15	89.36 (12)	O13—C1—C2	107.8 (3)
O4—Ni1—O15	92.05 (12)	O13—C1—P1	109.3 (2)
O1—Ni1—O12i	92.37 (11)	C2—C1—P1	114.5 (3)
O7i—Ni1—O12i	93.08 (10)	O13—C1—P2	106.1 (2)
O10—Ni1—O12i	89.82 (10)	C2—C1—P2	107.9 (3)
O4—Ni1—O12i	88.77 (10)	P1—C1—P2	110.97 (19)
O15—Ni1—O12i	179.18 (12)	C3—C2—C1	117.2 (3)
O1—P1—O3	115.32 (16)	C3—C2—H2A	108.0
O1—P1—O2	107.48 (16)	C1—C2—H2A	108.0
O3—P1—O2	110.75 (16)	C3—C2—H2B	108.0
O1—P1—C1	107.43 (16)	C1—C2—H2B	108.0
O3—P1—C1	109.11 (16)	H2A—C2—H2B	107.2
O2—P1—C1	106.33 (17)	C4—C3—C2	109.7 (3)
O5—P2—O4	113.25 (16)	C4—C3—H3A	109.7
O5—P2—O6	108.80 (16)	C2—C3—H3A	109.7
O4—P2—O6	111.05 (16)	C4—C3—H3B	109.7
O5—P2—C1	106.31 (17)	C2—C3—H3B	109.7
O4—P2—C1	109.97 (16)	H3A—C3—H3B	108.2
O6—P2—C1	107.18 (17)	N1—C4—C3	112.2 (4)
O7—P3—O8	115.04 (17)	N1—C4—H4A	109.2
O7—P3—O9	111.41 (17)	C3—C4—H4A	109.2
O8—P3—O9	106.36 (18)	N1—C4—H4B	109.2
O7—P3—C5	107.87 (17)	C3—C4—H4B	109.2
O8—P3—C5	108.56 (18)	H4A—C4—H4B	107.9
O9—P3—C5	107.33 (17)	O14—C5—C6	107.1 (3)
O10—P4—O12	116.83 (15)	O14—C5—P3	105.9 (3)
O10—P4—O11	110.80 (16)	C6—C5—P3	112.6 (3)
O12—P4—O11	105.41 (15)	O14—C5—P4	106.9 (3)
O10—P4—C5	112.03 (17)	C6—C5—P4	111.6 (3)
O12—P4—C5	107.24 (16)	P3—C5—P4	112.4 (2)
O11—P4—C5	103.50 (17)	C7—C6—C5	115.9 (3)
C4—N1—H1NA	109.5	C7—C6—H6A	108.3
C4—N1—H1NB	109.5	C5—C6—H6A	108.3
H1NA—N1—H1NB	109.5	C7—C6—H6B	108.3
C4—N1—H1NC	109.5	C5—C6—H6B	108.3
H1NA—N1—H1NC	109.5	H6A—C6—H6B	107.4
H1NB—N1—H1NC	109.5	C8—C7—C6	116.0 (4)
C8—N2—H2NA	109.5	C8—C7—H7A	108.3
C8—N2—H2NB	109.5	C6—C7—H7A	108.3
H2NA—N2—H2NB	109.5	C8—C7—H7B	108.3
C8—N2—H2C	109.5	C6—C7—H7B	108.3
H2NA—N2—H2C	109.5	H7A—C7—H7B	107.4
H2NB—N2—H2C	109.5	N2—C8—C7	110.8 (4)
P1—O1—Ni1	139.66 (17)	N2—C8—H8A	109.5
P1—O2—H2	109.5	C7—C8—H8A	109.5
P2—O4—Ni1	134.46 (17)	N2—C8—H8B	109.5
P2—O6—H6	109.5	C7—C8—H8B	109.5
P3—O7—Ni1i	131.97 (17)	H8A—C8—H8B	108.1
P3—O9—H9	109.5	O15—O16—H16A	135 (9)
P4—O10—Ni1	145.03 (17)	O15—O16—H16B	114 (8)
P4—O11—H11	109.5
O3—P1—O1—Ni1	−101.7 (3)	O1—P1—C1—P2	−54.6 (2)
O2—P1—O1—Ni1	134.3 (3)	O3—P1—C1—P2	71.1 (2)
C1—P1—O1—Ni1	20.2 (3)	O5—P2—C1—O13	59.5 (3)
O10—Ni1—O1—P1	−167.7 (3)	O4—P2—C1—O13	−63.4 (3)
O4—Ni1—O1—P1	10.7 (3)	O6—P2—C1—O13	175.8 (2)
O15—Ni1—O1—P1	102.8 (3)	O5—P2—C1—C2	−55.7 (3)
O12i—Ni1—O1—P1	−78.0 (3)	O4—P2—C1—C2	−178.7 (2)
O5—P2—O4—Ni1	−138.7 (2)	O6—P2—C1—C2	60.5 (3)
O6—P2—O4—Ni1	98.6 (2)	O4—P2—C1—P1	55.1 (2)
C1—P2—O4—Ni1	−19.9 (3)	O6—P2—C1—P1	−65.7 (2)
O1—Ni1—O4—P2	−10.8 (2)	O13—C1—C2—C3	49.4 (5)
O7i—Ni1—O4—P2	174.8 (2)	P1—C1—C2—C3	−72.4 (4)
O15—Ni1—O4—P2	−98.3 (2)	P2—C1—C2—C3	163.5 (3)
O12i—Ni1—O4—P2	81.6 (2)	C1—C2—C3—C4	179.1 (4)
O8—P3—O7—Ni1i	−168.3 (2)	C2—C3—C4—N1	−179.1 (4)
O9—P3—O7—Ni1i	70.6 (3)	O7—P3—C5—O14	−50.5 (3)
C5—P3—O7—Ni1i	−47.0 (3)	O8—P3—C5—O14	74.7 (3)
O12—P4—O10—Ni1	16.8 (4)	O9—P3—C5—O14	−170.7 (2)
O11—P4—O10—Ni1	137.5 (3)	O7—P3—C5—C6	−167.2 (3)
C5—P4—O10—Ni1	−107.5 (3)	O8—P3—C5—C6	−41.9 (3)
O1—Ni1—O10—P4	121.6 (3)	O9—P3—C5—C6	72.6 (3)
O7i—Ni1—O10—P4	−63.8 (3)	O7—P3—C5—P4	65.8 (2)
O15—Ni1—O10—P4	−150.8 (3)	O8—P3—C5—P4	−168.9 (2)
O12i—Ni1—O10—P4	29.2 (3)	O9—P3—C5—P4	−54.3 (2)
O10—P4—O12—Ni1i	−106.8 (2)	O10—P4—C5—O14	−166.6 (2)
O11—P4—O12—Ni1i	129.6 (2)	O12—P4—C5—O14	63.9 (3)
C5—P4—O12—Ni1i	19.8 (3)	O11—P4—C5—O14	−47.2 (3)
O1—Ni1—O15—O16	104.2 (3)	O10—P4—C5—C6	−49.9 (3)
O7i—Ni1—O15—O16	−82.2 (3)	O12—P4—C5—C6	−179.3 (3)
O10—Ni1—O15—O16	17.1 (3)	O11—P4—C5—C6	69.5 (3)
O4—Ni1—O15—O16	−165.8 (3)	O10—P4—C5—P3	77.6 (2)
O1—P1—C1—O13	62.1 (3)	O12—P4—C5—P3	−51.8 (2)
O3—P1—C1—O13	−172.3 (2)	O14—C5—C6—C7	−161.5 (4)
O2—P1—C1—O13	−52.8 (3)	P3—C5—C6—C7	−45.5 (4)
O1—P1—C1—C2	−177.0 (3)	P4—C5—C6—C7	81.9 (4)
O3—P1—C1—C2	−51.3 (3)	C5—C6—C7—C8	−139.6 (4)
O2—P1—C1—C2	68.2 (3)	C6—C7—C8—N2	66.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O11ii	0.89	2.27	3.000 (4)	140
N1—H1NB···O4iii	0.89	2.13	2.980 (5)	159
N1—H1NC···O5iv	0.89	1.93	2.806 (4)	168
N2—H2NA···O2v	0.89	2.43	3.215 (5)	147
N2—H2NB···O1	0.89	2.31	3.111 (5)	149
N2—H2C···O8v	0.89	2.30	3.169 (6)	167
O2—H2···O5iii	0.82	1.68	2.487 (4)	170
O6—H6···O3vi	0.82	1.73	2.539 (4)	168
O9—H9···O12i	0.82	1.89	2.665 (4)	157
O11—H11···O8v	0.82	1.78	2.585 (4)	165
O13—H13···O12i	0.82	2.08	2.898 (4)	172
O15—H15A···O3vi	0.83 (2)	2.00 (2)	2.815 (4)	168 (5)
O15—H15B···O16	0.82 (2)	2.29 (5)	2.882 (8)	130 (6)
O16—H16A···O8vii	0.88 (2)	2.57 (5)	3.365 (9)	151 (10)
O16—H16B···O8v	0.88 (2)	2.03 (3)	2.902 (8)	169 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NA⋯O11i	0.89	2.27	3.000 (4)	140
N1—H1NB⋯O4ii	0.89	2.13	2.980 (5)	159
N1—H1NC⋯O5iii	0.89	1.93	2.806 (4)	168
N2—H2NA⋯O2iv	0.89	2.43	3.215 (5)	147
N2—H2NB⋯O1	0.89	2.31	3.111 (5)	149
N2—H2C⋯O8iv	0.89	2.30	3.169 (6)	167
O2—H2⋯O5ii	0.82	1.68	2.487 (4)	170
O6—H6⋯O3v	0.82	1.73	2.539 (4)	168
O9—H9⋯O12vi	0.82	1.89	2.665 (4)	157
O11—H11⋯O8iv	0.82	1.78	2.585 (4)	165
O13—H13⋯O12vi	0.82	2.08	2.898 (4)	172
O15—H15A⋯O3v	0.83 (2)	2.00 (2)	2.815 (4)	168 (5)
O15—H15B⋯O16	0.82 (2)	2.29 (5)	2.882 (8)	130 (6)
O16—H16A⋯O8vii	0.88 (2)	2.57 (5)	3.365 (9)	151 (10)
O16—H16B⋯O8iv	0.88 (2)	2.03 (3)	2.902 (8)	169 (13)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .