Benzene-1,3-diammonium bis-(pyridine-2,6-dicarboxyl-ato)nickelate(II) penta-hydrate.

In the title compound, (C(6)H(10)N(2))[Ni(C(7)H(3)NO(4))(2)]·5H(2)O, the Ni(II) ion is six-coordinated by two N and four O atoms from two pyridine-2,6-dicarboxyl-ate ligands in a distorted octa-hedral fashion. The crystal packing is stabilized by inter-molecular O-H⋯O and N-H⋯O and weak C-H⋯O hydrogen bonds and π-π inter-actions [centroid-centroid distances = 3.4669 (19) and 3.764 (2) Å].

Related literature

For background to proton-transfer compounds, see: Aghabozorg et al. (2008 ▶). For related structures, see: Aghabozorg et al. (2009 ▶); Beatty et al. (2002 ▶); Dobrzycki & Woźniak (2008 ▶); Attar Gharamaleki et al. (2009 ▶); Imaz et al. (2007 ▶); MacDon­ald et al. (2000 ▶, 2004 ▶); Sharif et al. (2007 ▶).

Experimental

Crystal data

(C6H10N2)[Ni(C7H3NO4)2]·5H2O

M = 589.14

Monoclinic,

a = 7.5331 (15) Å

b = 18.085 (4) Å

c = 18.578 (4) Å

β = 100.90 (3)°

V = 2485.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.86 mm−1

T = 298 K

0.20 × 0.15 × 0.10 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: numerical (X-RED and X-SHAPE; Stoe & Cie, 2005 ▶) T min = 0.855, T max = 0.920

18439 measured reflections

6687 independent reflections

3608 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.086

S = 0.92

6687 reflections

407 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.36 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054371/bt5430sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054371/bt5430Isup2.hkl

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

(C6H10N2)[Ni(C7H3NO4)2]·5H2O	F(000) = 1224.0
Mr = 589.14	Dx = 1.574 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6687 reflections
a = 7.5331 (15) Å	θ = 2.2–29.2°
b = 18.085 (4) Å	µ = 0.86 mm−1
c = 18.578 (4) Å	T = 298 K
β = 100.90 (3)°	Needle, green
V = 2485.3 (9) Å3	0.2 × 0.15 × 0.1 mm
Z = 4

Stoe IPDS II diffractometer	6687 independent reflections
Radiation source: fine-focus sealed tube	3608 reflections with I > 2σ(I)
graphite	Rint = 0.090
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.2°, θmin = 2.2°
rotation method scans	h = −10→9
Absorption correction: numerical [shape of crystal determined optically (X-RED and X-SHAPE (Stoe & Cie, 2005)]	k = −24→24
Tmin = 0.855, Tmax = 0.920	l = −25→25
18439 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ2(Fo2) + (0.0238P)2] where P = (Fo2 + 2Fc2)/3
6687 reflections	(Δ/σ)max = 0.001
407 parameters	Δρmax = 0.39 e Å−3
4 restraints	Δρmin = −0.36 e Å−3

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.

	x	y	z	Uiso*/Ueq
O12	0.0352 (4)	0.65115 (16)	0.82305 (17)	0.0522 (8)
Ni1	0.64385 (6)	0.98344 (2)	0.81233 (2)	0.02316 (10)
N1	0.6858 (3)	1.00256 (12)	0.91843 (12)	0.0203 (5)
N2	0.6146 (3)	0.96578 (13)	0.70636 (12)	0.0225 (6)
O7	0.4041 (3)	0.91734 (12)	0.79023 (11)	0.0312 (5)
O3	0.4988 (3)	1.08346 (11)	0.81671 (11)	0.0305 (5)
O5	0.8722 (3)	1.03845 (12)	0.78742 (11)	0.0368 (6)
C11	0.7284 (5)	0.97699 (19)	0.59762 (16)	0.0354 (8)
H11	0.8166	0.9944	0.5730	0.042*
C12	0.7401 (4)	0.99113 (17)	0.67087 (15)	0.0262 (7)
O1	0.8002 (3)	0.89096 (11)	0.85564 (11)	0.0315 (5)
C1	0.7845 (4)	0.95527 (15)	0.96399 (15)	0.0200 (6)
C5	0.6176 (4)	1.06446 (15)	0.94246 (15)	0.0227 (7)
N3	0.9677 (4)	0.80203 (19)	0.77250 (17)	0.0290 (6)
C3	0.7580 (4)	1.03320 (17)	1.06483 (16)	0.0277 (7)
H3	0.7827	1.0437	1.1147	0.033*
C4	0.6531 (4)	1.08166 (17)	1.01596 (16)	0.0275 (7)
H4	0.6078	1.1249	1.0328	0.033*
C2	0.8252 (4)	0.96944 (16)	1.03883 (15)	0.0272 (7)
H2	0.8960	0.9368	1.0707	0.033*
C8	0.4727 (4)	0.92723 (16)	0.67186 (16)	0.0255 (7)
C15	0.8119 (4)	0.77521 (16)	0.71966 (16)	0.0241 (7)
C7	0.5013 (4)	1.10803 (16)	0.88110 (17)	0.0256 (7)
C20	0.6666 (4)	0.74641 (17)	0.74619 (17)	0.0261 (7)
H20	0.6665	0.7454	0.7962	0.031*
C16	0.8142 (4)	0.77784 (17)	0.64577 (17)	0.0289 (7)
H16	0.9119	0.7982	0.6287	0.035*
O4	0.4185 (3)	1.16332 (11)	0.89702 (12)	0.0322 (5)
O2	0.9292 (4)	0.83930 (13)	0.96180 (12)	0.0431 (6)
O8	0.2157 (3)	0.86339 (14)	0.69685 (13)	0.0467 (7)
O6	1.0038 (3)	1.06724 (13)	0.69308 (13)	0.0468 (7)
C19	0.5220 (4)	0.71920 (16)	0.69634 (16)	0.0238 (7)
N4	0.3701 (4)	0.68770 (17)	0.72430 (17)	0.0275 (6)
C18	0.5215 (4)	0.72028 (17)	0.62201 (17)	0.0303 (8)
H18	0.4235	0.7015	0.5890	0.036*
C6	0.8438 (4)	0.88880 (17)	0.92559 (16)	0.0266 (7)
C14	0.8847 (4)	1.03584 (17)	0.72077 (17)	0.0311 (8)
C17	0.6668 (5)	0.74933 (19)	0.59727 (17)	0.0369 (8)
H17	0.6669	0.7500	0.5472	0.044*
C9	0.4516 (5)	0.91218 (18)	0.59783 (17)	0.0334 (8)
H9	0.3513	0.8863	0.5734	0.040*
C10	0.5841 (5)	0.93673 (19)	0.56106 (18)	0.0394 (9)
H10	0.5756	0.9260	0.5116	0.047*
C13	0.3517 (4)	0.90100 (17)	0.72284 (16)	0.0271 (7)
O11	0.3389 (4)	0.77842 (17)	0.84618 (15)	0.0402 (7)
O9	0.5261 (5)	0.72860 (19)	0.98420 (18)	0.0583 (9)
O10	0.8429 (5)	0.6926 (2)	0.93695 (19)	0.0649 (9)
O13	0.8277 (5)	0.9051 (2)	0.4247 (2)	0.0646 (9)
H11A	0.360 (6)	0.820 (2)	0.839 (2)	0.057 (15)*
H11B	0.381 (6)	0.765 (2)	0.8838 (19)	0.062 (15)*
H12B	0.114 (8)	0.633 (4)	0.852 (3)	0.15 (3)*
H13A	0.879 (7)	0.923 (3)	0.398 (3)	0.11 (3)*
H12A	0.025 (7)	0.627 (3)	0.781 (3)	0.103 (19)*
H9B	0.552 (7)	0.761 (3)	1.018 (3)	0.09 (2)*
H9A	0.628 (7)	0.718 (2)	0.972 (2)	0.067 (17)*
H10A	0.857 (8)	0.670 (3)	0.902 (2)	0.10 (2)*
H13B	0.894 (7)	0.873 (3)	0.446 (3)	0.08 (2)*
H10B	0.882 (7)	0.744 (3)	0.940 (3)	0.095 (18)*
H3A	1.023 (6)	0.763 (2)	0.797 (2)	0.063 (14)*
H3B	1.051 (6)	0.826 (2)	0.750 (2)	0.056 (13)*
H3C	0.932 (6)	0.834 (2)	0.805 (2)	0.061 (13)*
H4C	0.398 (5)	0.641 (2)	0.750 (2)	0.054 (12)*
H4A	0.351 (5)	0.716 (2)	0.763 (2)	0.045 (11)*
H4B	0.279 (5)	0.6851 (18)	0.6925 (19)	0.034 (10)*

	U11	U22	U33	U12	U13	U23
O12	0.064 (2)	0.0460 (17)	0.0440 (17)	0.0030 (15)	0.0021 (16)	−0.0136 (14)
Ni1	0.0261 (2)	0.02501 (18)	0.01821 (16)	−0.0019 (2)	0.00388 (14)	−0.00170 (18)
N1	0.0188 (12)	0.0206 (14)	0.0222 (12)	−0.0019 (9)	0.0056 (10)	−0.0015 (9)
N2	0.0244 (13)	0.0238 (14)	0.0202 (12)	−0.0022 (10)	0.0065 (10)	−0.0012 (10)
O7	0.0347 (13)	0.0370 (13)	0.0238 (11)	−0.0078 (10)	0.0100 (10)	−0.0045 (9)
O3	0.0346 (13)	0.0301 (12)	0.0247 (11)	0.0043 (10)	0.0004 (10)	0.0004 (9)
O5	0.0391 (14)	0.0434 (14)	0.0279 (11)	−0.0156 (11)	0.0059 (10)	−0.0076 (10)
C11	0.047 (2)	0.0370 (18)	0.0253 (15)	−0.0073 (18)	0.0145 (14)	−0.0003 (15)
C12	0.0315 (16)	0.0238 (16)	0.0247 (14)	−0.0044 (14)	0.0087 (12)	0.0014 (13)
O1	0.0398 (14)	0.0310 (12)	0.0236 (11)	0.0110 (10)	0.0055 (10)	−0.0036 (9)
C1	0.0137 (14)	0.0242 (15)	0.0232 (14)	−0.0027 (12)	0.0065 (12)	0.0009 (12)
C5	0.0205 (15)	0.0215 (15)	0.0259 (15)	−0.0013 (12)	0.0037 (13)	0.0000 (12)
N3	0.0201 (15)	0.0389 (18)	0.0281 (15)	−0.0029 (14)	0.0049 (13)	−0.0087 (14)
C3	0.0271 (16)	0.0371 (19)	0.0194 (14)	−0.0066 (14)	0.0055 (13)	−0.0057 (12)
C4	0.0247 (16)	0.0303 (17)	0.0298 (16)	−0.0002 (13)	0.0108 (13)	−0.0110 (13)
C2	0.0287 (16)	0.0288 (18)	0.0222 (14)	−0.0009 (13)	0.0003 (13)	0.0027 (12)
C8	0.0308 (18)	0.0221 (15)	0.0228 (15)	−0.0016 (13)	0.0033 (13)	0.0001 (12)
C15	0.0191 (15)	0.0245 (16)	0.0275 (16)	0.0021 (13)	0.0013 (13)	−0.0072 (13)
C7	0.0231 (16)	0.0222 (16)	0.0300 (17)	−0.0034 (13)	0.0012 (13)	−0.0005 (13)
C20	0.0230 (16)	0.0331 (17)	0.0223 (15)	−0.0011 (14)	0.0045 (13)	−0.0028 (13)
C16	0.0272 (17)	0.0323 (18)	0.0291 (17)	−0.0044 (14)	0.0102 (14)	−0.0026 (14)
O4	0.0273 (12)	0.0288 (12)	0.0397 (13)	0.0071 (10)	0.0046 (10)	−0.0025 (10)
O2	0.0580 (17)	0.0336 (13)	0.0354 (13)	0.0184 (12)	0.0028 (12)	0.0041 (10)
O8	0.0359 (15)	0.0651 (17)	0.0383 (14)	−0.0234 (13)	0.0050 (12)	−0.0055 (12)
O6	0.0472 (16)	0.0525 (16)	0.0451 (15)	−0.0244 (13)	0.0199 (12)	−0.0063 (12)
C19	0.0195 (15)	0.0224 (15)	0.0298 (16)	0.0021 (12)	0.0055 (13)	−0.0021 (13)
N4	0.0202 (15)	0.0293 (16)	0.0323 (16)	−0.0033 (12)	0.0029 (13)	−0.0012 (13)
C18	0.0294 (18)	0.0313 (18)	0.0282 (16)	−0.0047 (14)	0.0001 (14)	−0.0062 (13)
C6	0.0266 (17)	0.0269 (17)	0.0266 (16)	−0.0008 (14)	0.0056 (14)	−0.0010 (13)
C14	0.0299 (18)	0.0325 (19)	0.0337 (17)	−0.0066 (14)	0.0132 (14)	−0.0037 (14)
C17	0.042 (2)	0.047 (2)	0.0215 (16)	−0.0046 (17)	0.0054 (16)	−0.0021 (15)
C9	0.036 (2)	0.0371 (19)	0.0248 (16)	−0.0068 (15)	0.0012 (15)	−0.0032 (14)
C10	0.054 (2)	0.044 (2)	0.0226 (17)	−0.0075 (18)	0.0128 (16)	−0.0024 (15)
C13	0.0239 (17)	0.0287 (17)	0.0299 (17)	−0.0004 (14)	0.0082 (14)	0.0003 (13)
O11	0.0474 (17)	0.0362 (16)	0.0357 (16)	−0.0017 (13)	0.0051 (13)	0.0008 (13)
O9	0.059 (2)	0.068 (2)	0.0464 (19)	0.0053 (18)	0.0066 (17)	−0.0100 (16)
O10	0.077 (2)	0.058 (2)	0.063 (2)	0.0039 (18)	0.0247 (18)	−0.0084 (18)
O13	0.060 (2)	0.082 (3)	0.059 (2)	−0.001 (2)	0.0275 (19)	0.0045 (19)

O12—H12B	0.79 (4)	C2—H2	0.9300
O12—H12A	0.89 (6)	C8—C9	1.381 (4)
Ni1—N2	1.965 (2)	C8—C13	1.510 (5)
Ni1—N1	1.967 (2)	C15—C16	1.377 (4)
Ni1—O5	2.113 (2)	C15—C20	1.384 (4)
Ni1—O1	2.115 (2)	C7—O4	1.244 (4)
Ni1—O3	2.123 (2)	C20—C19	1.380 (4)
Ni1—O7	2.140 (2)	C20—H20	0.9300
N1—C1	1.328 (3)	C16—C17	1.390 (4)
N1—C5	1.343 (4)	C16—H16	0.9300
N2—C12	1.332 (4)	O2—C6	1.226 (3)
N2—C8	1.334 (4)	O8—C13	1.248 (4)
O7—C13	1.274 (3)	O6—C14	1.251 (4)
O3—C7	1.273 (4)	C19—C18	1.381 (4)
O5—C14	1.260 (4)	C19—N4	1.459 (4)
C11—C12	1.371 (4)	N4—H4C	0.97 (4)
C11—C10	1.376 (5)	N4—H4A	0.91 (4)
C11—H11	0.9300	N4—H4B	0.82 (3)
C12—C14	1.522 (4)	C18—C17	1.370 (5)
O1—C6	1.279 (3)	C18—H18	0.9300
C1—C2	1.390 (4)	C17—H17	0.9300
C1—C6	1.508 (4)	C9—C10	1.385 (5)
C5—C4	1.376 (4)	C9—H9	0.9300
C5—C7	1.520 (4)	C10—H10	0.9300
N3—C15	1.463 (4)	O11—H11A	0.79 (4)
N3—H3A	0.91 (4)	O11—H11B	0.75 (3)
N3—H3B	0.93 (5)	O9—H9B	0.85 (5)
N3—H3C	0.91 (5)	O9—H9A	0.86 (5)
C3—C2	1.383 (4)	O10—H10A	0.79 (3)
C3—C4	1.395 (4)	O10—H10B	0.97 (5)
C3—H3	0.9300	O13—H13A	0.76 (4)
C4—H4	0.9300	O13—H13B	0.82 (5)
H12B—O12—H12A	109 (6)	C3—C2—H2	120.7
N2—Ni1—N1	177.13 (11)	C1—C2—H2	120.7
N2—Ni1—O5	78.39 (10)	N2—C8—C9	120.8 (3)
N1—Ni1—O5	98.84 (9)	N2—C8—C13	112.7 (3)
N2—Ni1—O1	101.62 (9)	C9—C8—C13	126.4 (3)
N1—Ni1—O1	77.61 (9)	C16—C15—C20	121.9 (3)
O5—Ni1—O1	92.17 (9)	C16—C15—N3	119.8 (3)
N2—Ni1—O3	102.47 (9)	C20—C15—N3	118.3 (3)
N1—Ni1—O3	78.34 (9)	O4—C7—O3	125.8 (3)
O5—Ni1—O3	93.06 (9)	O4—C7—C5	118.9 (3)
O1—Ni1—O3	155.91 (8)	O3—C7—C5	115.3 (3)
N2—Ni1—O7	77.66 (10)	C19—C20—C15	118.2 (3)
N1—Ni1—O7	105.08 (9)	C19—C20—H20	120.9
O5—Ni1—O7	156.01 (8)	C15—C20—H20	120.9
O1—Ni1—O7	91.16 (9)	C15—C16—C17	118.3 (3)
O3—Ni1—O7	93.54 (9)	C15—C16—H16	120.8
C1—N1—C5	121.9 (2)	C17—C16—H16	120.8
C1—N1—Ni1	119.34 (19)	C20—C19—C18	121.2 (3)
C5—N1—Ni1	118.74 (18)	C20—C19—N4	118.2 (3)
C12—N2—C8	121.4 (3)	C18—C19—N4	120.5 (3)
C12—N2—Ni1	118.97 (19)	C19—N4—H4C	114 (2)
C8—N2—Ni1	119.6 (2)	C19—N4—H4A	108 (2)
C13—O7—Ni1	114.3 (2)	H4C—N4—H4A	99 (3)
C7—O3—Ni1	114.67 (18)	C19—N4—H4B	112 (3)
C14—O5—Ni1	114.38 (19)	H4C—N4—H4B	112 (3)
C12—C11—C10	119.0 (3)	H4A—N4—H4B	111 (3)
C12—C11—H11	120.5	C17—C18—C19	119.3 (3)
C10—C11—H11	120.5	C17—C18—H18	120.3
N2—C12—C11	120.6 (3)	C19—C18—H18	120.3
N2—C12—C14	112.0 (2)	O2—C6—O1	125.9 (3)
C11—C12—C14	127.4 (3)	O2—C6—C1	119.6 (3)
C6—O1—Ni1	115.35 (19)	O1—C6—C1	114.5 (3)
N1—C1—C2	120.7 (3)	O6—C14—O5	125.4 (3)
N1—C1—C6	113.1 (2)	O6—C14—C12	118.5 (3)
C2—C1—C6	126.2 (3)	O5—C14—C12	116.1 (3)
N1—C5—C4	120.3 (3)	C18—C17—C16	121.1 (3)
N1—C5—C7	112.7 (2)	C18—C17—H17	119.5
C4—C5—C7	127.1 (3)	C16—C17—H17	119.5
C15—N3—H3A	108 (3)	C8—C9—C10	118.0 (3)
C15—N3—H3B	112 (2)	C8—C9—H9	121.0
H3A—N3—H3B	108 (4)	C10—C9—H9	121.0
C15—N3—H3C	111 (3)	C11—C10—C9	120.1 (3)
H3A—N3—H3C	109 (4)	C11—C10—H10	119.9
H3B—N3—H3C	109 (4)	C9—C10—H10	119.9
C2—C3—C4	119.8 (3)	O8—C13—O7	125.8 (3)
C2—C3—H3	120.1	O8—C13—C8	118.5 (3)
C4—C3—H3	120.1	O7—C13—C8	115.6 (3)
C5—C4—C3	118.9 (3)	H11A—O11—H11B	113 (4)
C5—C4—H4	120.6	H9B—O9—H9A	105 (5)
C3—C4—H4	120.6	H10A—O10—H10B	117 (6)
C3—C2—C1	118.5 (3)	H13A—O13—H13B	106 (6)
N2—Ni1—N1—C1	−74 (2)	Ni1—N1—C5—C4	−176.3 (2)
O5—Ni1—N1—C1	−89.1 (2)	C1—N1—C5—C7	−177.0 (3)
O1—Ni1—N1—C1	1.2 (2)	Ni1—N1—C5—C7	4.9 (3)
O3—Ni1—N1—C1	179.6 (2)	N1—C5—C4—C3	−1.0 (5)
O7—Ni1—N1—C1	89.0 (2)	C7—C5—C4—C3	177.5 (3)
N2—Ni1—N1—C5	104 (2)	C2—C3—C4—C5	0.4 (5)
O5—Ni1—N1—C5	89.0 (2)	C4—C3—C2—C1	−0.4 (5)
O1—Ni1—N1—C5	179.3 (2)	N1—C1—C2—C3	1.1 (4)
O3—Ni1—N1—C5	−2.3 (2)	C6—C1—C2—C3	−179.5 (3)
O7—Ni1—N1—C5	−92.9 (2)	C12—N2—C8—C9	0.2 (4)
N1—Ni1—N2—C12	−14 (2)	Ni1—N2—C8—C9	−178.1 (2)
O5—Ni1—N2—C12	2.1 (2)	C12—N2—C8—C13	177.5 (3)
O1—Ni1—N2—C12	−87.8 (2)	Ni1—N2—C8—C13	−0.8 (3)
O3—Ni1—N2—C12	92.7 (2)	Ni1—O3—C7—O4	−176.1 (3)
O7—Ni1—N2—C12	−176.4 (2)	Ni1—O3—C7—C5	4.0 (3)
N1—Ni1—N2—C8	164.8 (19)	N1—C5—C7—O4	174.2 (3)
O5—Ni1—N2—C8	−179.6 (2)	C4—C5—C7—O4	−4.4 (5)
O1—Ni1—N2—C8	90.5 (2)	N1—C5—C7—O3	−5.9 (4)
O3—Ni1—N2—C8	−89.0 (2)	C4—C5—C7—O3	175.5 (3)
O7—Ni1—N2—C8	1.9 (2)	C16—C15—C20—C19	0.6 (5)
N2—Ni1—O7—C13	−2.9 (2)	N3—C15—C20—C19	−178.2 (3)
N1—Ni1—O7—C13	178.0 (2)	C20—C15—C16—C17	−1.2 (5)
O5—Ni1—O7—C13	−6.6 (3)	N3—C15—C16—C17	177.6 (3)
O1—Ni1—O7—C13	−104.5 (2)	C15—C20—C19—C18	0.2 (4)
O3—Ni1—O7—C13	99.1 (2)	C15—C20—C19—N4	179.0 (3)
N2—Ni1—O3—C7	−178.4 (2)	C20—C19—C18—C17	−0.4 (5)
N1—Ni1—O3—C7	−1.2 (2)	N4—C19—C18—C17	−179.2 (3)
O5—Ni1—O3—C7	−99.6 (2)	Ni1—O1—C6—O2	177.8 (3)
O1—Ni1—O3—C7	2.7 (4)	Ni1—O1—C6—C1	−3.4 (3)
O7—Ni1—O3—C7	103.5 (2)	N1—C1—C6—O2	−176.8 (3)
N2—Ni1—O5—C14	0.6 (2)	C2—C1—C6—O2	3.7 (5)
N1—Ni1—O5—C14	179.8 (2)	N1—C1—C6—O1	4.4 (4)
O1—Ni1—O5—C14	102.0 (2)	C2—C1—C6—O1	−175.1 (3)
O3—Ni1—O5—C14	−101.6 (2)	Ni1—O5—C14—O6	176.6 (3)
O7—Ni1—O5—C14	4.2 (4)	Ni1—O5—C14—C12	−2.7 (3)
C8—N2—C12—C11	−1.2 (4)	N2—C12—C14—O6	−175.0 (3)
Ni1—N2—C12—C11	177.1 (2)	C11—C12—C14—O6	3.9 (5)
C8—N2—C12—C14	177.8 (3)	N2—C12—C14—O5	4.3 (4)
Ni1—N2—C12—C14	−3.9 (3)	C11—C12—C14—O5	−176.7 (3)
C10—C11—C12—N2	0.6 (5)	C19—C18—C17—C16	−0.2 (5)
C10—C11—C12—C14	−178.3 (3)	C15—C16—C17—C18	0.9 (5)
N2—Ni1—O1—C6	178.6 (2)	N2—C8—C9—C10	1.5 (5)
N1—Ni1—O1—C6	1.5 (2)	C13—C8—C9—C10	−175.4 (3)
O5—Ni1—O1—C6	100.0 (2)	C12—C11—C10—C9	1.1 (5)
O3—Ni1—O1—C6	−2.4 (4)	C8—C9—C10—C11	−2.1 (5)
O7—Ni1—O1—C6	−103.7 (2)	Ni1—O7—C13—O8	−179.7 (3)
C5—N1—C1—C2	−1.8 (4)	Ni1—O7—C13—C8	3.3 (3)
Ni1—N1—C1—C2	176.3 (2)	N2—C8—C13—O8	−179.0 (3)
C5—N1—C1—C6	178.8 (3)	C9—C8—C13—O8	−1.9 (5)
Ni1—N1—C1—C6	−3.2 (3)	N2—C8—C13—O7	−1.8 (4)
C1—N1—C5—C4	1.7 (4)	C9—C8—C13—O7	175.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2i	0.93	2.48	3.118 (4)	126.
C3—H3···O7ii	0.93	2.56	3.284 (4)	135.
O13—H13B···O9iii	0.82 (5)	2.14 (5)	2.945 (6)	166 (5)
O13—H13A···O6iv	0.76 (4)	2.05 (4)	2.776 (5)	158 (6)
O12—H12B···O13v	0.79 (4)	2.02 (4)	2.808 (5)	176 (8)
O12—H12A···O3vi	0.89 (6)	1.95 (6)	2.838 (4)	174 (5)
O11—H11B···O9	0.75 (3)	2.08 (3)	2.829 (4)	173 (5)
O11—H11A···O7	0.79 (4)	2.03 (4)	2.798 (4)	163 (4)
O10—H10B···O2	0.97 (5)	1.80 (5)	2.750 (4)	168 (5)
O10—H10A···O12vii	0.79 (3)	2.20 (5)	2.880 (5)	146 (6)
O9—H9B···O4ii	0.85 (5)	2.07 (5)	2.918 (4)	172 (5)
O9—H9A···O10	0.86 (5)	1.91 (5)	2.772 (5)	176 (4)
N4—H4C···O6viii	0.97 (4)	1.78 (4)	2.730 (4)	167 (3)
N4—H4B···O4vi	0.82 (3)	2.05 (4)	2.854 (4)	168 (3)
N4—H4A···O11	0.91 (4)	1.94 (4)	2.842 (4)	173 (3)
N3—H3C···O1	0.91 (5)	1.82 (5)	2.702 (4)	164 (4)
N3—H3B···O8vii	0.93 (5)	1.85 (5)	2.773 (4)	173 (4)
N3—H3A···O12vii	0.91 (4)	2.07 (4)	2.899 (5)	152 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2i	0.93	2.48	3.118 (4)	126
C3—H3⋯O7ii	0.93	2.56	3.284 (4)	135
O13—H13B⋯O9iii	0.82 (5)	2.14 (5)	2.945 (6)	166 (5)
O13—H13A⋯O6iv	0.76 (4)	2.05 (4)	2.776 (5)	158 (6)
O12—H12B⋯O13v	0.79 (4)	2.02 (4)	2.808 (5)	176 (8)
O12—H12A⋯O3vi	0.89 (6)	1.95 (6)	2.838 (4)	174 (5)
O11—H11B⋯O9	0.75 (3)	2.08 (3)	2.829 (4)	173 (5)
O11—H11A⋯O7	0.79 (4)	2.03 (4)	2.798 (4)	163 (4)
O10—H10B⋯O2	0.97 (5)	1.80 (5)	2.750 (4)	168 (5)
O10—H10A⋯O12vii	0.79 (3)	2.20 (5)	2.880 (5)	146 (6)
O9—H9B⋯O4ii	0.85 (5)	2.07 (5)	2.918 (4)	172 (5)
O9—H9A⋯O10	0.86 (5)	1.91 (5)	2.772 (5)	176 (4)
N4—H4C⋯O6viii	0.97 (4)	1.78 (4)	2.730 (4)	167 (3)
N4—H4B⋯O4vi	0.82 (3)	2.05 (4)	2.854 (4)	168 (3)
N4—H4A⋯O11	0.91 (4)	1.94 (4)	2.842 (4)	173 (3)
N3—H3C⋯O1	0.91 (5)	1.82 (5)	2.702 (4)	164 (4)
N3—H3B⋯O8vii	0.93 (5)	1.85 (5)	2.773 (4)	173 (4)
N3—H3A⋯O12vii	0.91 (4)	2.07 (4)	2.899 (5)	152 (4)

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