Diaqua-(5-carb-oxy-benzene-1,3-dicarboxyl-ato-κO,O)(6,6'-dimethyl-2,2'-bipyridine-κN,N')nickel(II) hepta-hydrate.

In the title compound, [Ni(C(9)H(4)O(6))(C(12)H(12)N(2))(H(2)O)(2)]·7H(2)O, the Ni(II) atom is six-coordinated by two O atoms from a chelating carboxyl-ate group of a 5-carb-oxy-benzene-1,3-dicarboxyl-ate ligand, two O atoms of two water mol-ecules and two N atoms from a 6,6'-dimethyl-2,2'-bipyridine ligand in a distorted octa-hedral geometry. The compound exhibits a three-dimensional supra-molecular structure composed of the complex mol-ecules and lattice water mol-ecules, which are linked together by inter-molecular O-H⋯O hydrogen bonds and partly overlapping π-π inter-actions between the pyridine and benzene rings [centroid-centroid distances = 3.922 (2) and 3.921 (2) Å]. One of the lattice water mol-ecules is disordered over two positions in an occupancy ratio of 0.521 (6):0.479 (6).

Related literature

For background to network topologies and applications of coordination polymers, see: Maspoch et al. (2007 ▶); Ockwig et al. (2005 ▶); Zang et al. (2006 ▶). For O—H⋯O hydrogen bonds, see: Desiraju (2004 ▶). For π–π inter­actions, see: Zang et al. (2010 ▶).

Experimental

Crystal data

[Ni(C9H4O6)(C12H12N2)(H2O)2]·7H2O

M = 613.21

Monoclinic,

a = 7.4358 (5) Å

b = 19.9044 (7) Å

c = 18.7547 (12) Å

β = 100.748 (6)°

V = 2727.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.79 mm−1

T = 296 K

0.21 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.852, T max = 0.865

10544 measured reflections

4792 independent reflections

3924 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.112

S = 1.07

4792 reflections

359 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811032090/hy2454sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032090/hy2454Isup2.hkl

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

[Ni(C9H4O6)(C12H12N2)(H2O)2]·7H2O	F(000) = 1288
Mr = 613.21	Dx = 1.494 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5756 reflections
a = 7.4358 (5) Å	θ = 3.1–25.1°
b = 19.9044 (7) Å	µ = 0.79 mm−1
c = 18.7547 (12) Å	T = 296 K
β = 100.748 (6)°	Block, green
V = 2727.1 (3) Å3	0.21 × 0.20 × 0.19 mm
Z = 4

Bruker APEXII CCD diffractometer	4792 independent reflections
Radiation source: fine-focus sealed tube	3924 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→7
Tmin = 0.852, Tmax = 0.865	k = −23→23
10544 measured reflections	l = −22→18

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0512P)2 + 1.4022P] where P = (Fo2 + 2Fc2)/3
4792 reflections	(Δ/σ)max < 0.001
359 parameters	Δρmax = 0.52 e Å−3
7 restraints	Δρmin = −0.44 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.70769 (6)	0.080884 (19)	0.25745 (2)	0.03021 (16)
O1	0.7517 (4)	−0.01080 (10)	0.20364 (13)	0.0418 (6)
O2	0.6738 (3)	−0.01416 (10)	0.30997 (12)	0.0346 (5)
O3	0.7991 (4)	−0.21564 (10)	0.07083 (12)	0.0413 (6)
H3	0.7996	−0.2377	0.0339	0.062*
O4	0.8529 (4)	−0.31588 (11)	0.12401 (12)	0.0407 (6)
O5	0.7135 (3)	−0.32604 (11)	0.38608 (12)	0.0403 (6)
O6	0.7669 (4)	−0.22980 (11)	0.44653 (12)	0.0414 (6)
O1W	0.9818 (3)	0.07458 (11)	0.30571 (13)	0.0402 (6)
H1WA	1.0248	0.1139	0.3142	0.060*
H1WB	0.9917	0.0530	0.3454	0.060*
O2W	0.4405 (4)	0.07809 (12)	0.20585 (16)	0.0592 (8)
H2WA	0.4003	0.1180	0.1991	0.089*
H2WC	0.3779	0.0569	0.2321	0.089*
O3W	0.2685 (6)	0.07326 (15)	0.00654 (18)	0.0889 (12)
H3WA	0.2790	0.1069	0.0349	0.133*
H3WB	0.2908	0.0402	0.0355	0.133*
O4W	0.0439 (13)	0.3920 (4)	0.0141 (4)	0.0793 (16)	0.479 (6)
H4WA	0.1206	0.3496	0.0243	0.119*	0.479 (6)
H4WB	0.0705	0.3718	−0.0225	0.119*	0.479 (6)
O4W'	0.1795 (12)	0.4147 (3)	0.0175 (4)	0.0793 (16)	0.521 (6)
H4WD	0.1938	0.3757	0.0273	0.119*	0.521 (6)
H4WF	0.0831	0.4181	−0.0182	0.119*	0.521 (6)
O5W	0.6215 (7)	0.43234 (17)	0.1293 (4)	0.175 (3)
H5WA	0.6808	0.4337	0.1758	0.262*
H5WC	0.5221	0.4502	0.1360	0.262*
O6W	0.9119 (5)	0.48672 (16)	0.08448 (19)	0.0840 (11)
H6WC	0.9703	0.4542	0.0703	0.126*
H6WA	0.8303	0.4723	0.0972	0.126*
O7W	0.8074 (5)	0.4822 (2)	0.2739 (2)	0.0973 (12)
H7WB	0.8414	0.4718	0.3154	0.146*
H7WC	0.8916	0.5056	0.2610	0.146*
O8W	0.9166 (6)	0.4315 (3)	0.4073 (3)	0.1361 (19)
H8WB	0.8012	0.4305	0.4152	0.204*
H8WC	0.9868	0.4048	0.4350	0.204*
O9W	0.5399 (5)	0.45536 (17)	0.42213 (18)	0.0861 (11)
H9WB	0.4716	0.4663	0.3823	0.129*
H9WC	0.4442	0.4530	0.4406	0.129*
N1	0.7626 (4)	0.16095 (13)	0.19407 (16)	0.0380 (7)
N2	0.6634 (4)	0.15982 (13)	0.32397 (16)	0.0371 (7)
C1	0.7209 (4)	−0.04411 (16)	0.25714 (17)	0.0301 (7)
C2	0.8196 (4)	−0.25571 (15)	0.12681 (17)	0.0296 (7)
C3	0.7403 (4)	−0.26418 (15)	0.38882 (17)	0.0287 (7)
C4	0.7420 (4)	−0.11928 (15)	0.25751 (16)	0.0270 (7)
C5	0.7759 (4)	−0.15158 (14)	0.19578 (16)	0.0274 (7)
H5	0.7871	−0.1267	0.1549	0.033*
C6	0.7933 (4)	−0.22150 (14)	0.19505 (16)	0.0254 (7)
C7	0.7778 (4)	−0.25820 (15)	0.25693 (16)	0.0262 (7)
H7	0.7881	−0.3048	0.2564	0.031*
C8	0.7472 (4)	−0.22603 (14)	0.31937 (16)	0.0251 (7)
C9	0.7290 (4)	−0.15617 (14)	0.31904 (16)	0.0281 (7)
H9	0.7079	−0.1342	0.3605	0.034*
C10	0.8084 (5)	0.15830 (19)	0.1278 (2)	0.0463 (9)
C11	0.8383 (8)	0.0920 (2)	0.0959 (2)	0.0712 (14)
H11A	0.9197	0.0657	0.1308	0.107*
H11B	0.8912	0.0983	0.0535	0.107*
H11C	0.7233	0.0690	0.0828	0.107*
C12	0.8301 (6)	0.2173 (2)	0.0901 (2)	0.0556 (11)
H12	0.8643	0.2151	0.0449	0.067*
C13	0.8017 (6)	0.2778 (2)	0.1191 (3)	0.0645 (13)
H13	0.8127	0.3171	0.0933	0.077*
C14	0.7566 (6)	0.28089 (18)	0.1865 (3)	0.0577 (12)
H14	0.7375	0.3222	0.2071	0.069*
C15	0.7398 (5)	0.22160 (16)	0.2236 (2)	0.0414 (9)
C16	0.6961 (5)	0.22106 (16)	0.2969 (2)	0.0412 (9)
C17	0.6877 (6)	0.27930 (19)	0.3363 (3)	0.0585 (12)
H17	0.7148	0.3207	0.3178	0.070*
C18	0.6393 (6)	0.2752 (2)	0.4028 (3)	0.0659 (13)
H18	0.6316	0.3140	0.4297	0.079*
C19	0.6020 (6)	0.2140 (2)	0.4300 (2)	0.0581 (12)
H19	0.5677	0.2112	0.4751	0.070*
C20	0.6156 (5)	0.15593 (18)	0.3898 (2)	0.0455 (9)
C21	0.5736 (8)	0.0888 (2)	0.4174 (2)	0.0686 (14)
H21A	0.4809	0.0673	0.3824	0.103*
H21B	0.5305	0.0941	0.4622	0.103*
H21C	0.6824	0.0618	0.4254	0.103*

	U11	U22	U33	U12	U13	U23
Ni1	0.0398 (3)	0.0199 (2)	0.0289 (3)	−0.00149 (17)	0.00125 (18)	0.00021 (16)
O1	0.0762 (19)	0.0220 (11)	0.0287 (13)	−0.0036 (11)	0.0135 (12)	0.0041 (10)
O2	0.0500 (15)	0.0223 (11)	0.0325 (13)	0.0009 (10)	0.0104 (11)	−0.0024 (9)
O3	0.0785 (19)	0.0281 (12)	0.0199 (12)	0.0030 (12)	0.0156 (12)	−0.0016 (10)
O4	0.0666 (17)	0.0266 (12)	0.0291 (13)	0.0142 (11)	0.0092 (12)	−0.0010 (10)
O5	0.0648 (17)	0.0262 (12)	0.0289 (13)	−0.0097 (11)	0.0058 (12)	0.0044 (10)
O6	0.0755 (19)	0.0306 (12)	0.0196 (12)	−0.0032 (12)	0.0123 (12)	0.0001 (10)
O1W	0.0412 (14)	0.0314 (12)	0.0441 (15)	−0.0031 (10)	−0.0022 (11)	0.0000 (11)
O2W	0.0478 (16)	0.0412 (14)	0.078 (2)	−0.0101 (12)	−0.0174 (14)	0.0219 (14)
O3W	0.151 (4)	0.0525 (19)	0.057 (2)	0.020 (2)	0.004 (2)	−0.0123 (16)
O4W	0.105 (4)	0.068 (3)	0.065 (3)	0.021 (3)	0.013 (3)	0.006 (2)
O4W'	0.105 (4)	0.068 (3)	0.065 (3)	0.021 (3)	0.013 (3)	0.006 (2)
O5W	0.194 (5)	0.052 (2)	0.336 (8)	0.018 (3)	0.198 (6)	0.017 (3)
O6W	0.083 (3)	0.073 (2)	0.091 (3)	−0.0016 (18)	0.004 (2)	−0.0246 (19)
O7W	0.070 (2)	0.130 (3)	0.098 (3)	0.026 (2)	0.031 (2)	−0.006 (3)
O8W	0.102 (3)	0.180 (5)	0.135 (4)	0.023 (3)	0.043 (3)	0.070 (4)
O9W	0.100 (3)	0.092 (2)	0.058 (2)	0.017 (2)	−0.0040 (19)	0.0068 (19)
N1	0.0387 (17)	0.0293 (14)	0.0420 (18)	−0.0055 (12)	−0.0027 (13)	0.0060 (13)
N2	0.0342 (16)	0.0318 (15)	0.0420 (18)	0.0030 (12)	−0.0010 (13)	−0.0071 (13)
C1	0.0387 (19)	0.0241 (16)	0.0255 (17)	−0.0023 (14)	0.0006 (14)	−0.0025 (14)
C2	0.0364 (19)	0.0286 (17)	0.0243 (17)	0.0008 (14)	0.0067 (14)	0.0007 (14)
C3	0.0370 (19)	0.0264 (16)	0.0226 (17)	−0.0004 (14)	0.0054 (13)	0.0024 (13)
C4	0.0346 (18)	0.0211 (15)	0.0245 (16)	−0.0032 (13)	0.0035 (13)	−0.0002 (12)
C5	0.0392 (19)	0.0250 (15)	0.0178 (15)	−0.0002 (13)	0.0046 (13)	0.0037 (12)
C6	0.0320 (17)	0.0233 (15)	0.0201 (15)	0.0005 (13)	0.0029 (13)	0.0012 (12)
C7	0.0337 (17)	0.0207 (14)	0.0228 (16)	0.0002 (13)	0.0017 (13)	0.0010 (12)
C8	0.0320 (17)	0.0236 (15)	0.0194 (15)	−0.0022 (13)	0.0037 (13)	0.0015 (12)
C9	0.0389 (19)	0.0253 (15)	0.0208 (16)	−0.0011 (13)	0.0072 (13)	−0.0023 (13)
C10	0.048 (2)	0.047 (2)	0.041 (2)	−0.0110 (18)	−0.0007 (18)	0.0122 (18)
C11	0.117 (4)	0.060 (3)	0.042 (2)	−0.019 (3)	0.029 (3)	0.001 (2)
C12	0.050 (3)	0.057 (3)	0.056 (3)	−0.010 (2)	−0.001 (2)	0.026 (2)
C13	0.054 (3)	0.052 (3)	0.083 (4)	−0.008 (2)	−0.001 (2)	0.036 (2)
C14	0.050 (3)	0.0293 (19)	0.089 (4)	0.0000 (17)	0.002 (2)	0.015 (2)
C15	0.0311 (19)	0.0276 (18)	0.061 (3)	−0.0013 (14)	−0.0029 (17)	0.0042 (17)
C16	0.0294 (19)	0.0255 (17)	0.063 (3)	0.0015 (14)	−0.0057 (17)	−0.0059 (16)
C17	0.055 (3)	0.032 (2)	0.081 (3)	0.0043 (18)	−0.006 (2)	−0.013 (2)
C18	0.064 (3)	0.045 (2)	0.080 (4)	0.008 (2)	−0.010 (3)	−0.030 (2)
C19	0.057 (3)	0.061 (3)	0.051 (3)	0.010 (2)	−0.004 (2)	−0.027 (2)
C20	0.045 (2)	0.045 (2)	0.043 (2)	0.0077 (17)	−0.0010 (17)	−0.0136 (18)
C21	0.104 (4)	0.060 (3)	0.047 (3)	0.004 (3)	0.029 (3)	−0.008 (2)

Ni1—O2W	2.042 (3)	N2—C16	1.360 (4)
Ni1—N2	2.070 (3)	C1—C4	1.504 (4)
Ni1—O1W	2.074 (2)	C2—C6	1.494 (4)
Ni1—N1	2.074 (3)	C3—C8	1.517 (4)
Ni1—O1	2.140 (2)	C4—C9	1.386 (4)
Ni1—O2	2.169 (2)	C4—C5	1.388 (4)
O1—C1	1.259 (4)	C5—C6	1.398 (4)
O2—C1	1.261 (4)	C5—H5	0.9300
O3—C2	1.305 (4)	C6—C7	1.394 (4)
O3—H3	0.8200	C7—C8	1.390 (4)
O4—C2	1.226 (4)	C7—H7	0.9300
O5—C3	1.247 (4)	C8—C9	1.397 (4)
O6—C3	1.265 (4)	C9—H9	0.9300
O1W—H1WA	0.8500	C10—C12	1.396 (5)
O1W—H1WB	0.8499	C10—C11	1.483 (6)
O2W—H2WA	0.8502	C11—H11A	0.9600
O2W—H2WC	0.8499	C11—H11B	0.9600
O3W—H3WA	0.8500	C11—H11C	0.9600
O3W—H3WB	0.8497	C12—C13	1.354 (6)
O4W—H4WA	1.0159	C12—H12	0.9300
O4W—H4WB	0.8499	C13—C14	1.368 (7)
O4W'—H4WD	0.8000	C13—H13	0.9300
O4W'—H4WF	0.8879	C14—C15	1.388 (5)
O5W—H5WA	0.9000	C14—H14	0.9300
O5W—H5WC	0.8500	C15—C16	1.470 (6)
O6W—H6WC	0.8499	C16—C17	1.383 (5)
O6W—H6WA	0.7500	C17—C18	1.362 (7)
O7W—H7WC	0.8500	C17—H17	0.9300
O7W—H7WB	0.8001	C18—C19	1.368 (6)
O7W—H7WC	0.8500	C18—H18	0.9300
O8W—H8WB	0.8978	C19—C20	1.395 (5)
O8W—H8WC	0.8500	C19—H19	0.9300
O9W—H9WB	0.8502	C20—C21	1.486 (6)
O9W—H9WC	0.8499	C21—H21A	0.9600
N1—C10	1.350 (5)	C21—H21B	0.9600
N1—C15	1.352 (4)	C21—H21C	0.9600
N2—C20	1.349 (5)
O2W—Ni1—N2	93.23 (11)	C7—C6—C5	119.4 (3)
O2W—Ni1—O1W	174.46 (10)	C7—C6—C2	121.2 (3)
N2—Ni1—O1W	92.10 (10)	C5—C6—C2	119.3 (3)
O2W—Ni1—N1	91.57 (11)	C8—C7—C6	120.8 (3)
N2—Ni1—N1	80.36 (12)	C8—C7—H7	119.6
O1W—Ni1—N1	90.82 (10)	C6—C7—H7	119.6
O2W—Ni1—O1	88.51 (11)	C7—C8—C9	119.1 (3)
N2—Ni1—O1	170.69 (10)	C7—C8—C3	122.0 (3)
O1W—Ni1—O1	85.99 (10)	C9—C8—C3	118.9 (3)
N1—Ni1—O1	108.75 (10)	C4—C9—C8	120.6 (3)
O2W—Ni1—O2	90.35 (9)	C4—C9—H9	119.7
N2—Ni1—O2	110.07 (10)	C8—C9—H9	119.7
O1W—Ni1—O2	86.39 (9)	N1—C10—C12	120.4 (4)
N1—Ni1—O2	169.27 (10)	N1—C10—C11	119.3 (3)
O1—Ni1—O2	60.74 (9)	C12—C10—C11	120.3 (4)
C1—O1—Ni1	90.39 (19)	C10—C11—H11A	109.5
C1—O2—Ni1	89.00 (18)	C10—C11—H11B	109.5
C2—O3—H3	109.5	H11A—C11—H11B	109.5
Ni1—O1W—H1WA	109.3	C10—C11—H11C	109.5
Ni1—O1W—H1WB	109.3	H11A—C11—H11C	109.5
H1WA—O1W—H1WB	109.5	H11B—C11—H11C	109.5
Ni1—O2W—H2WA	109.2	C13—C12—C10	120.2 (4)
Ni1—O2W—H2WC	109.2	C13—C12—H12	119.9
H2WA—O2W—H2WC	109.5	C10—C12—H12	119.9
H3WA—O3W—H3WB	103.1	C12—C13—C14	119.6 (4)
H4WA—O4W—H4WB	63.5	C12—C13—H13	120.2
H4WB—O4W—H4WD	71.2	C14—C13—H13	120.2
H4WD—O4W'—H4WF	107.6	C13—C14—C15	119.1 (4)
H5WA—O5W—H5WC	97.4	C13—C14—H14	120.5
H6WC—O6W—H6WA	107.4	C15—C14—H14	120.5
H7WC—O7W—H7WB	107.6	N1—C15—C14	121.6 (4)
H7WB—O7W—H7WC	107.6	N1—C15—C16	116.3 (3)
H8WB—O8W—H8WC	112.6	C14—C15—C16	122.1 (3)
H9WB—O9W—H9WC	88.0	N2—C16—C17	121.5 (4)
C10—N1—C15	119.0 (3)	N2—C16—C15	116.2 (3)
C10—N1—Ni1	127.5 (2)	C17—C16—C15	122.3 (3)
C15—N1—Ni1	113.4 (2)	C18—C17—C16	119.0 (4)
C20—N2—C16	119.3 (3)	C18—C17—H17	120.5
C20—N2—Ni1	127.3 (2)	C16—C17—H17	120.5
C16—N2—Ni1	113.3 (2)	C17—C18—C19	120.1 (4)
O1—C1—O2	119.7 (3)	C17—C18—H18	120.0
O1—C1—C4	119.5 (3)	C19—C18—H18	120.0
O2—C1—C4	120.7 (3)	C18—C19—C20	119.7 (4)
O4—C2—O3	123.9 (3)	C18—C19—H19	120.1
O4—C2—C6	122.8 (3)	C20—C19—H19	120.1
O3—C2—C6	113.3 (3)	N2—C20—C19	120.4 (4)
O5—C3—O6	124.6 (3)	N2—C20—C21	118.6 (3)
O5—C3—C8	119.3 (3)	C19—C20—C21	121.0 (4)
O6—C3—C8	116.1 (3)	C20—C21—H21A	109.5
C9—C4—C5	120.1 (3)	C20—C21—H21B	109.5
C9—C4—C1	120.5 (3)	H21A—C21—H21B	109.5
C5—C4—C1	119.5 (3)	C20—C21—H21C	109.5
C4—C5—C6	120.1 (3)	H21A—C21—H21C	109.5
C4—C5—H5	120.0	H21B—C21—H21C	109.5
C6—C5—H5	120.0
O2W—Ni1—O1—C1	−93.3 (2)	C2—C6—C7—C8	−177.8 (3)
O1W—Ni1—O1—C1	86.0 (2)	C6—C7—C8—C9	1.1 (5)
N1—Ni1—O1—C1	175.52 (19)	C6—C7—C8—C3	−176.5 (3)
O2—Ni1—O1—C1	−2.09 (18)	O5—C3—C8—C7	−19.0 (5)
O2W—Ni1—O2—C1	90.2 (2)	O6—C3—C8—C7	159.5 (3)
N2—Ni1—O2—C1	−176.26 (18)	O5—C3—C8—C9	163.4 (3)
O1W—Ni1—O2—C1	−85.34 (19)	O6—C3—C8—C9	−18.1 (4)
N1—Ni1—O2—C1	−10.2 (6)	C5—C4—C9—C8	−0.9 (5)
O1—Ni1—O2—C1	2.08 (18)	C1—C4—C9—C8	179.5 (3)
O2W—Ni1—N1—C10	−85.4 (3)	C7—C8—C9—C4	−0.3 (5)
N2—Ni1—N1—C10	−178.4 (3)	C3—C8—C9—C4	177.4 (3)
O1W—Ni1—N1—C10	89.6 (3)	C15—N1—C10—C12	−0.6 (5)
O1—Ni1—N1—C10	3.6 (3)	Ni1—N1—C10—C12	176.0 (3)
O2—Ni1—N1—C10	14.8 (7)	C15—N1—C10—C11	178.4 (4)
O2W—Ni1—N1—C15	91.4 (2)	Ni1—N1—C10—C11	−5.0 (5)
N2—Ni1—N1—C15	−1.6 (2)	N1—C10—C12—C13	−1.4 (6)
O1W—Ni1—N1—C15	−93.6 (2)	C11—C10—C12—C13	179.6 (4)
O1—Ni1—N1—C15	−179.6 (2)	C10—C12—C13—C14	1.9 (6)
O2—Ni1—N1—C15	−168.3 (5)	C12—C13—C14—C15	−0.4 (6)
O2W—Ni1—N2—C20	89.9 (3)	C10—N1—C15—C14	2.1 (5)
O1W—Ni1—N2—C20	−88.6 (3)	Ni1—N1—C15—C14	−175.0 (3)
N1—Ni1—N2—C20	−179.1 (3)	C10—N1—C15—C16	−178.0 (3)
O2—Ni1—N2—C20	−1.7 (3)	Ni1—N1—C15—C16	4.9 (4)
O2W—Ni1—N2—C16	−93.2 (2)	C13—C14—C15—N1	−1.6 (6)
O1W—Ni1—N2—C16	88.3 (2)	C13—C14—C15—C16	178.5 (4)
N1—Ni1—N2—C16	−2.2 (2)	C20—N2—C16—C17	2.3 (5)
O2—Ni1—N2—C16	175.2 (2)	Ni1—N2—C16—C17	−174.9 (3)
Ni1—O1—C1—O2	3.6 (3)	C20—N2—C16—C15	−177.5 (3)
Ni1—O1—C1—C4	−176.0 (3)	Ni1—N2—C16—C15	5.4 (4)
Ni1—O2—C1—O1	−3.6 (3)	N1—C15—C16—N2	−7.0 (5)
Ni1—O2—C1—C4	176.0 (3)	C14—C15—C16—N2	172.9 (3)
O1—C1—C4—C9	172.7 (3)	N1—C15—C16—C17	173.3 (3)
O2—C1—C4—C9	−6.9 (5)	C14—C15—C16—C17	−6.9 (6)
O1—C1—C4—C5	−6.9 (5)	N2—C16—C17—C18	−2.3 (6)
O2—C1—C4—C5	173.6 (3)	C15—C16—C17—C18	177.4 (4)
C9—C4—C5—C6	1.3 (5)	C16—C17—C18—C19	0.8 (6)
C1—C4—C5—C6	−179.1 (3)	C17—C18—C19—C20	0.6 (6)
C4—C5—C6—C7	−0.5 (5)	C16—N2—C20—C19	−0.8 (5)
C4—C5—C6—C2	176.7 (3)	Ni1—N2—C20—C19	176.0 (3)
O4—C2—C6—C7	−9.8 (5)	C16—N2—C20—C21	177.8 (4)
O3—C2—C6—C7	168.5 (3)	Ni1—N2—C20—C21	−5.5 (5)
O4—C2—C6—C5	173.0 (3)	C18—C19—C20—N2	−0.7 (6)
O3—C2—C6—C5	−8.7 (4)	C18—C19—C20—C21	−179.2 (4)
C5—C6—C7—C8	−0.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O6i	0.82	1.74	2.542 (3)	167
O1W—H1WA···O4ii	0.85	1.93	2.720 (3)	154
O1W—H1WB···O6Wiii	0.85	1.91	2.705 (4)	156
O2W—H2WA···O5iv	0.85	2.00	2.681 (3)	136
O2W—H2WC···O7Wv	0.85	2.02	2.729 (4)	141
O3W—H3WA···O5iv	0.85	1.99	2.827 (4)	169
O3W—H3WB···O9Wv	0.85	2.17	2.935 (5)	150
O4W—H4WA···O6iv	1.02	1.82	2.830 (7)	170
O4W—H4WB···O4vi	0.85	2.36	3.215 (8)	179
O4W'—H4WD···O6iv	0.80	2.16	2.964 (7)	180
O4W'—H4WF···O6Wvii	0.89	2.27	2.736 (7)	113
O5W—H5WA···O7W	0.90	2.14	2.974 (8)	155
O5W—H5WC···O2iv	0.85	2.05	2.860 (4)	159
O6W—H6WC···O4Wviii	0.85	1.78	2.597 (8)	162
O6W—H6WA···O5W	0.75	1.94	2.687 (5)	178
O7W—H7WB···O8W	0.80	1.89	2.681 (6)	170
O7W—H7WC···O1Wii	0.85	2.19	2.990 (5)	158
O8W—H8WB···O9W	0.90	2.03	2.905 (6)	164
O8W—H8WC···O3Wix	0.85	2.31	2.916 (6)	129
O9W—H9WB···O1iv	0.85	2.14	2.968 (4)	166
O9W—H9WC···O3Wx	0.85	2.03	2.845 (5)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O6i	0.82	1.74	2.542 (3)	167
O1W—H1WA⋯O4ii	0.85	1.93	2.720 (3)	154
O1W—H1WB⋯O6Wiii	0.85	1.91	2.705 (4)	156
O2W—H2WA⋯O5iv	0.85	2.00	2.681 (3)	136
O2W—H2WC⋯O7Wv	0.85	2.02	2.729 (4)	141
O3W—H3WA⋯O5iv	0.85	1.99	2.827 (4)	169
O3W—H3WB⋯O9Wv	0.85	2.17	2.935 (5)	150
O4W—H4WA⋯O6iv	1.02	1.82	2.830 (7)	170
O4W—H4WB⋯O4vi	0.85	2.36	3.215 (8)	179
O4W′—H4WD⋯O6iv	0.80	2.16	2.964 (7)	180
O4W′—H4WF⋯O6Wvii	0.89	2.27	2.736 (7)	113
O5W—H5WA⋯O7W	0.90	2.14	2.974 (8)	155
O5W—H5WC⋯O2iv	0.85	2.05	2.860 (4)	159
O6W—H6WC⋯O4Wviii	0.85	1.78	2.597 (8)	162
O6W—H6WA⋯O5W	0.75	1.94	2.687 (5)	178
O7W—H7WB⋯O8W	0.80	1.89	2.681 (6)	170
O7W—H7WC⋯O1Wii	0.85	2.19	2.990 (5)	158
O8W—H8WB⋯O9W	0.90	2.03	2.905 (6)	164
O8W—H8WC⋯O3Wix	0.85	2.31	2.916 (6)	129
O9W—H9WB⋯O1iv	0.85	2.14	2.968 (4)	166
O9W—H9WC⋯O3Wx	0.85	2.03	2.845 (5)	162

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