(Pyridine-2,6-di­carboxyl­ato-κ³O,N,O′)(2,2′:6′,2′′- terpyridine-κ³N,N′,N′′)nickel(II) di­methyl­formamide monosolvate monohydrate

In the title complex, [Ni(C₇H₃NO₄)(C₁₅H₁₁N₃)]·C₃H₇NO·H₂O, the Ni^II ion is six-coordinated within an octa­hedral geometry defined by three N atoms of the 2,2′:6′,2′′-terpyridine ligand, and two O atoms and the N atom of the pyridine-2,6-di­carboxyl­ate di-anion. In the crystal, the complex mol­ecules are stacked in columns parallel to the a axis being connected by π–π stacking [closest inter-centroid separation between pyridyl rings = 3.669 (3) Å]. The connections between columns and solvent mol­ecules to sustain a three-dimensional architecture are of the type water-O—H...O(carbon­yl) and pyridyl-, methyl-C—H...O(carbon­yl).

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.051
• wR factor = 0.105
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.176
PLAT213_ALERT_2_C Atom C10             has ADP max/min Ratio .....        3.4 prolat
PLAT213_ALERT_2_C Atom C20             has ADP max/min Ratio .....        3.2 prolat
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        4.5 Ratio
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C10 Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C20 Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of         N5 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0062 Ang.
PLAT354_ALERT_3_C Short  O-H (X0.82,N0.98A)  O6       - H6A      .       0.71 Ang.
PLAT411_ALERT_2_C Short Inter H...H Contact  H10      ..H20      .       2.10 Ang.
                                           1+x,1/2-y,-1/2+z  =      4_665 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      6.608 Check

Alert level G
PLAT020_ALERT_3_G The Value of Rint is Greater Than 0.12 .........      0.176 Report
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1       (II)      .       2.23 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  12 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXL2014 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(Pyridine-2,6-dicarboxylato-κ³O,N,O')(2,2':6',2''-terpyridine-κ³N,N',N'')nickel(II) dimethylformamide monosolvate monohydrate

Crystal data

[Ni(C7H3NO4)(C15H11N3)]·C3H7NO·H2O	F(000) = 1136
Mr = 548.19	Dx = 1.529 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.6188 (4) Å	Cell parameters from 7834 reflections
b = 27.5899 (13) Å	θ = 2.5–25.4°
c = 10.7559 (5) Å	µ = 0.87 mm^−1
β = 111.3813 (11)°	T = 223 K
V = 2381.62 (19) Å^3	Block, green
Z = 4	0.16 × 0.13 × 0.09 mm

Data collection

PHOTON 100 CMOS detector diffractometer	3085 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.176
φ and ω scans	θmax = 26.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −10→10
Tmin = 0.683, Tmax = 0.745	k = −34→34
66113 measured reflections	l = −13→13
4729 independent reflections

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)] = 0.051	Hydrogen site location: mixed
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0327P)^2 + 2.9447P] where P = (Fo^2 + 2Fc^2)/3
4729 reflections	(Δ/σ)max < 0.001
344 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

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. Hydrogen atoms were positioned geometrically and allowed to ride on their respective parent atoms: C—H = 0.94 Å (CH) or 0.97 Å (CH₃), and U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C). The H atoms of the solvent water molecule were localized from Fourier difference maps and refined with isotropic thermal parameters.

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

	x	y	z	Uiso*/Ueq
Ni1	0.36206 (5)	0.16002 (2)	0.23583 (4)	0.02137 (13)
O1	0.1553 (3)	0.14429 (8)	0.0586 (2)	0.0267 (6)
O2	−0.0024 (3)	0.08186 (9)	−0.0495 (2)	0.0378 (6)
O3	0.5679 (3)	0.14403 (9)	0.4142 (2)	0.0309 (6)
O4	0.7196 (3)	0.08116 (10)	0.5247 (3)	0.0467 (7)
N1	0.3587 (3)	0.08889 (9)	0.2374 (3)	0.0203 (6)
N2	0.5267 (3)	0.17374 (10)	0.1390 (3)	0.0260 (7)
N3	0.3713 (3)	0.23164 (9)	0.2408 (3)	0.0233 (6)
N4	0.2007 (3)	0.17652 (10)	0.3353 (3)	0.0259 (7)
C1	0.2379 (4)	0.06562 (12)	0.1423 (3)	0.0224 (8)
C2	0.2282 (5)	0.01548 (13)	0.1436 (4)	0.0304 (9)
H2	0.1413	−0.0011	0.0780	0.037*
C3	0.3494 (5)	−0.00932 (12)	0.2437 (4)	0.0347 (9)
H3	0.3457	−0.0433	0.2467	0.042*
C4	0.4770 (5)	0.01570 (13)	0.3402 (4)	0.0313 (9)
H4	0.5614	−0.0011	0.4076	0.038*
C5	0.4770 (4)	0.06553 (12)	0.3350 (3)	0.0239 (8)
C6	0.1188 (4)	0.09963 (13)	0.0402 (3)	0.0262 (8)
C7	0.6005 (4)	0.09928 (14)	0.4347 (4)	0.0295 (8)
C8	0.6049 (5)	0.14092 (14)	0.0920 (4)	0.0349 (9)
H8	0.5753	0.1081	0.0923	0.042*
C9	0.7263 (6)	0.15281 (16)	0.0435 (5)	0.0611 (14)
H9	0.7804	0.1288	0.0121	0.073*
C10	0.7662 (7)	0.20063 (18)	0.0422 (7)	0.099 (2)
H10	0.8502	0.2099	0.0106	0.119*
C11	0.6846 (6)	0.23548 (16)	0.0869 (6)	0.0767 (18)
H11	0.7097	0.2685	0.0837	0.092*
C12	0.5658 (4)	0.22089 (13)	0.1361 (4)	0.0328 (9)
C13	0.4719 (4)	0.25468 (12)	0.1902 (4)	0.0303 (9)
C14	0.4840 (5)	0.30440 (14)	0.1940 (4)	0.0451 (11)
H14	0.5530	0.3206	0.1571	0.054*
C15	0.3911 (5)	0.33003 (13)	0.2541 (5)	0.0506 (12)
H15	0.3992	0.3640	0.2599	0.061*
C16	0.2876 (5)	0.30606 (14)	0.3051 (4)	0.0423 (10)
H16	0.2230	0.3233	0.3441	0.051*
C17	0.2804 (4)	0.25613 (12)	0.2978 (3)	0.0273 (8)
C18	0.1788 (5)	0.22411 (13)	0.3493 (4)	0.0311 (9)
C19	0.0730 (7)	0.24084 (16)	0.4088 (6)	0.0727 (17)
H19	0.0593	0.2742	0.4188	0.087*
C20	−0.0130 (8)	0.20715 (19)	0.4536 (7)	0.100 (2)
H20	−0.0847	0.2177	0.4962	0.120*
C21	0.0047 (6)	0.15893 (17)	0.4370 (5)	0.0616 (14)
H21	−0.0564	0.1359	0.4647	0.074*
C22	0.1139 (5)	0.14506 (14)	0.3787 (4)	0.0364 (10)
H22	0.1290	0.1118	0.3685	0.044*
O5	0.4038 (4)	0.05868 (11)	0.8998 (3)	0.0635 (9)
N5	0.1913 (4)	0.01358 (12)	0.7603 (3)	0.0400 (8)
C23	0.3260 (6)	0.02115 (17)	0.8683 (4)	0.0503 (11)
H23	0.3651	−0.0053	0.9265	0.060*
C24	0.1119 (6)	−0.03242 (17)	0.7291 (5)	0.0701 (15)
H24A	−0.0072	−0.0284	0.7054	0.105*
H24B	0.1553	−0.0536	0.8060	0.105*
H24C	0.1336	−0.0466	0.6544	0.105*
C25	0.1256 (7)	0.05288 (19)	0.6690 (6)	0.0858 (18)
H25A	0.1672	0.0507	0.5967	0.129*
H25B	0.1602	0.0834	0.7156	0.129*
H25C	0.0049	0.0511	0.6331	0.129*
O6	0.8679 (5)	0.15110 (13)	0.7334 (5)	0.0590 (10)
H6A	0.896 (6)	0.1358 (18)	0.790 (5)	0.052 (19)*
H6B	0.825 (8)	0.133 (2)	0.681 (6)	0.10 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0231 (2)	0.0176 (2)	0.0246 (2)	−0.0026 (2)	0.01005 (17)	−0.0023 (2)
O1	0.0277 (13)	0.0196 (13)	0.0297 (14)	−0.0020 (10)	0.0067 (11)	−0.0014 (10)
O2	0.0318 (15)	0.0330 (16)	0.0351 (15)	−0.0064 (12)	−0.0038 (13)	−0.0066 (12)
O3	0.0301 (14)	0.0295 (15)	0.0282 (14)	−0.0047 (11)	0.0048 (12)	−0.0050 (11)
O4	0.0410 (17)	0.0473 (18)	0.0350 (16)	0.0014 (14)	−0.0061 (14)	0.0063 (14)
N1	0.0212 (14)	0.0200 (14)	0.0211 (14)	0.0003 (13)	0.0096 (12)	0.0015 (13)
N2	0.0278 (16)	0.0220 (17)	0.0313 (17)	−0.0016 (12)	0.0145 (14)	−0.0019 (13)
N3	0.0244 (15)	0.0189 (14)	0.0280 (15)	−0.0009 (13)	0.0112 (13)	−0.0031 (13)
N4	0.0280 (16)	0.0218 (16)	0.0306 (17)	−0.0042 (13)	0.0141 (14)	−0.0042 (13)
C1	0.0236 (18)	0.0212 (19)	0.0246 (19)	−0.0027 (15)	0.0113 (16)	−0.0056 (15)
C2	0.033 (2)	0.024 (2)	0.035 (2)	−0.0027 (17)	0.0129 (18)	−0.0049 (17)
C3	0.047 (2)	0.0163 (18)	0.046 (2)	0.0005 (19)	0.023 (2)	0.0017 (19)
C4	0.034 (2)	0.028 (2)	0.032 (2)	0.0094 (17)	0.0125 (18)	0.0100 (17)
C5	0.0254 (19)	0.027 (2)	0.0228 (19)	0.0034 (15)	0.0130 (16)	0.0051 (15)
C6	0.027 (2)	0.026 (2)	0.028 (2)	−0.0055 (16)	0.0120 (17)	−0.0041 (16)
C7	0.029 (2)	0.034 (2)	0.026 (2)	−0.0038 (18)	0.0104 (18)	0.0014 (18)
C8	0.039 (2)	0.028 (2)	0.045 (2)	0.0015 (18)	0.024 (2)	−0.0037 (18)
C9	0.074 (3)	0.039 (3)	0.104 (4)	0.003 (2)	0.072 (3)	−0.006 (3)
C10	0.120 (5)	0.043 (3)	0.205 (7)	−0.008 (3)	0.143 (5)	−0.007 (4)
C11	0.095 (4)	0.028 (3)	0.157 (5)	−0.010 (3)	0.106 (4)	−0.006 (3)
C12	0.034 (2)	0.024 (2)	0.048 (2)	−0.0033 (17)	0.026 (2)	−0.0026 (18)
C13	0.031 (2)	0.0197 (19)	0.043 (2)	−0.0033 (16)	0.0162 (19)	0.0010 (17)
C14	0.050 (3)	0.026 (2)	0.073 (3)	−0.0043 (19)	0.039 (3)	0.005 (2)
C15	0.062 (3)	0.018 (2)	0.084 (4)	−0.005 (2)	0.041 (3)	−0.003 (2)
C16	0.050 (3)	0.024 (2)	0.064 (3)	0.0024 (19)	0.033 (2)	−0.008 (2)
C17	0.027 (2)	0.023 (2)	0.032 (2)	0.0006 (15)	0.0116 (17)	−0.0040 (16)
C18	0.040 (2)	0.025 (2)	0.036 (2)	−0.0011 (17)	0.0229 (19)	−0.0053 (17)
C19	0.103 (4)	0.031 (3)	0.132 (5)	0.002 (3)	0.100 (4)	−0.005 (3)
C20	0.141 (5)	0.049 (3)	0.184 (7)	0.005 (3)	0.146 (6)	−0.002 (4)
C21	0.081 (3)	0.038 (3)	0.101 (4)	−0.007 (3)	0.075 (3)	−0.003 (3)
C22	0.047 (2)	0.025 (2)	0.048 (3)	−0.0044 (18)	0.030 (2)	−0.0031 (17)
O5	0.068 (2)	0.046 (2)	0.068 (2)	−0.0134 (17)	0.0142 (18)	−0.0164 (17)
N5	0.041 (2)	0.0323 (19)	0.045 (2)	0.0012 (16)	0.0135 (18)	−0.0004 (16)
C23	0.061 (3)	0.052 (3)	0.041 (3)	0.003 (2)	0.022 (2)	−0.003 (2)
C24	0.071 (4)	0.057 (3)	0.090 (4)	−0.021 (3)	0.039 (3)	−0.014 (3)
C25	0.067 (4)	0.065 (4)	0.099 (5)	0.012 (3)	0.000 (3)	0.017 (3)
O6	0.063 (2)	0.046 (2)	0.053 (2)	0.009 (2)	0.0028 (18)	0.003 (2)

Geometric parameters (Å, º)

Ni1—N1	1.963 (2)	C11—C12	1.373 (5)
Ni1—N3	1.978 (3)	C11—H11	0.9400
Ni1—N2	2.078 (3)	C12—C13	1.486 (5)
Ni1—N4	2.091 (3)	C13—C14	1.375 (5)
Ni1—O1	2.126 (2)	C14—C15	1.391 (5)
Ni1—O3	2.131 (2)	C14—H14	0.9400
O1—C6	1.269 (4)	C15—C16	1.375 (5)
O2—C6	1.236 (4)	C15—H15	0.9400
O3—C7	1.268 (4)	C16—C17	1.380 (5)
O4—C7	1.232 (4)	C16—H16	0.9400
N1—C1	1.329 (4)	C17—C18	1.485 (5)
N1—C5	1.333 (4)	C18—C19	1.372 (5)
N2—C8	1.333 (4)	C19—C20	1.380 (6)
N2—C12	1.347 (4)	C19—H19	0.9400
N3—C17	1.340 (4)	C20—C21	1.358 (6)
N3—C13	1.340 (4)	C20—H20	0.9400
N4—C22	1.336 (4)	C21—C22	1.362 (5)
N4—C18	1.343 (4)	C21—H21	0.9400
C1—C2	1.386 (5)	C22—H22	0.9400
C1—C6	1.523 (5)	O5—C23	1.213 (5)
C2—C3	1.377 (5)	N5—C23	1.326 (5)
C2—H2	0.9400	N5—C24	1.423 (5)
C3—C4	1.390 (5)	N5—C25	1.433 (6)
C3—H3	0.9400	C23—H23	0.9400
C4—C5	1.376 (5)	C24—H24A	0.9700
C4—H4	0.9400	C24—H24B	0.9700
C5—C7	1.523 (5)	C24—H24C	0.9700
C8—C9	1.369 (5)	C25—H25A	0.9700
C8—H8	0.9400	C25—H25B	0.9700
C9—C10	1.365 (6)	C25—H25C	0.9700
C9—H9	0.9400	O6—H6A	0.71 (5)
C10—C11	1.377 (6)	O6—H6B	0.74 (6)
C10—H10	0.9400
N1—Ni1—N3	177.95 (12)	C9—C10—H10	119.7
N1—Ni1—N2	101.62 (11)	C11—C10—H10	119.7
N3—Ni1—N2	78.67 (11)	C12—C11—C10	118.5 (4)
N1—Ni1—N4	101.44 (11)	C12—C11—H11	120.7
N3—Ni1—N4	78.25 (11)	C10—C11—H11	120.7
N2—Ni1—N4	156.92 (10)	N2—C12—C11	121.4 (3)
N1—Ni1—O1	78.07 (10)	N2—C12—C13	114.8 (3)
N3—Ni1—O1	103.93 (10)	C11—C12—C13	123.8 (3)
N2—Ni1—O1	95.16 (10)	N3—C13—C14	120.9 (3)
N4—Ni1—O1	90.40 (10)	N3—C13—C12	112.8 (3)
N1—Ni1—O3	78.18 (11)	C14—C13—C12	126.3 (3)
N3—Ni1—O3	99.81 (11)	C13—C14—C15	118.1 (3)
N2—Ni1—O3	89.59 (10)	C13—C14—H14	121.0
N4—Ni1—O3	94.29 (10)	C15—C14—H14	121.0
O1—Ni1—O3	156.26 (9)	C16—C15—C14	120.5 (3)
C6—O1—Ni1	114.7 (2)	C16—C15—H15	119.7
C7—O3—Ni1	114.7 (2)	C14—C15—H15	119.7
C1—N1—C5	122.2 (3)	C15—C16—C17	118.7 (3)
C1—N1—Ni1	119.1 (2)	C15—C16—H16	120.7
C5—N1—Ni1	118.7 (2)	C17—C16—H16	120.7
C8—N2—C12	118.8 (3)	N3—C17—C16	120.5 (3)
C8—N2—Ni1	126.7 (2)	N3—C17—C18	113.1 (3)
C12—N2—Ni1	114.2 (2)	C16—C17—C18	126.4 (3)
C17—N3—C13	121.3 (3)	N4—C18—C19	121.7 (3)
C17—N3—Ni1	119.4 (2)	N4—C18—C17	114.4 (3)
C13—N3—Ni1	119.2 (2)	C19—C18—C17	123.8 (3)
C22—N4—C18	118.5 (3)	C18—C19—C20	118.0 (4)
C22—N4—Ni1	126.8 (2)	C18—C19—H19	121.0
C18—N4—Ni1	114.6 (2)	C20—C19—H19	121.0
N1—C1—C2	120.5 (3)	C21—C20—C19	120.9 (4)
N1—C1—C6	113.0 (3)	C21—C20—H20	119.5
C2—C1—C6	126.5 (3)	C19—C20—H20	119.5
C3—C2—C1	118.2 (3)	C20—C21—C22	117.7 (4)
C3—C2—H2	120.9	C20—C21—H21	121.1
C1—C2—H2	120.9	C22—C21—H21	121.1
C2—C3—C4	120.3 (3)	N4—C22—C21	123.2 (4)
C2—C3—H3	119.8	N4—C22—H22	118.4
C4—C3—H3	119.8	C21—C22—H22	118.4
C5—C4—C3	118.5 (3)	C23—N5—C24	122.6 (4)
C5—C4—H4	120.7	C23—N5—C25	118.8 (4)
C3—C4—H4	120.7	C24—N5—C25	118.5 (4)
N1—C5—C4	120.3 (3)	O5—C23—N5	126.7 (5)
N1—C5—C7	113.4 (3)	O5—C23—H23	116.7
C4—C5—C7	126.4 (3)	N5—C23—H23	116.7
O2—C6—O1	126.7 (3)	N5—C24—H24A	109.5
O2—C6—C1	118.3 (3)	N5—C24—H24B	109.5
O1—C6—C1	115.0 (3)	H24A—C24—H24B	109.5
O4—C7—O3	126.9 (3)	N5—C24—H24C	109.5
O4—C7—C5	118.3 (3)	H24A—C24—H24C	109.5
O3—C7—C5	114.8 (3)	H24B—C24—H24C	109.5
N2—C8—C9	122.9 (4)	N5—C25—H25A	109.5
N2—C8—H8	118.5	N5—C25—H25B	109.5
C9—C8—H8	118.5	H25A—C25—H25B	109.5
C10—C9—C8	117.8 (4)	N5—C25—H25C	109.5
C10—C9—H9	121.1	H25A—C25—H25C	109.5
C8—C9—H9	121.1	H25B—C25—H25C	109.5
C9—C10—C11	120.6 (4)	H6A—O6—H6B	100 (6)
C5—N1—C1—C2	1.9 (5)	C10—C11—C12—C13	178.5 (5)
Ni1—N1—C1—C2	−177.4 (2)	C17—N3—C13—C14	−0.6 (6)
C5—N1—C1—C6	−179.0 (3)	Ni1—N3—C13—C14	−178.8 (3)
Ni1—N1—C1—C6	1.7 (3)	C17—N3—C13—C12	178.0 (3)
N1—C1—C2—C3	−1.8 (5)	Ni1—N3—C13—C12	−0.3 (4)
C6—C1—C2—C3	179.2 (3)	N2—C12—C13—N3	4.1 (5)
C1—C2—C3—C4	0.1 (5)	C11—C12—C13—N3	−175.6 (4)
C2—C3—C4—C5	1.5 (5)	N2—C12—C13—C14	−177.4 (4)
C1—N1—C5—C4	−0.2 (5)	C11—C12—C13—C14	2.9 (7)
Ni1—N1—C5—C4	179.1 (2)	N3—C13—C14—C15	1.1 (6)
C1—N1—C5—C7	−178.8 (3)	C12—C13—C14—C15	−177.2 (4)
Ni1—N1—C5—C7	0.5 (3)	C13—C14—C15—C16	−1.5 (7)
C3—C4—C5—N1	−1.5 (5)	C14—C15—C16—C17	1.3 (7)
C3—C4—C5—C7	176.9 (3)	C13—N3—C17—C16	0.4 (5)
Ni1—O1—C6—O2	174.4 (3)	Ni1—N3—C17—C16	178.6 (3)
Ni1—O1—C6—C1	−4.7 (3)	C13—N3—C17—C18	−179.3 (3)
N1—C1—C6—O2	−177.0 (3)	Ni1—N3—C17—C18	−1.0 (4)
C2—C1—C6—O2	2.1 (5)	C15—C16—C17—N3	−0.7 (6)
N1—C1—C6—O1	2.2 (4)	C15—C16—C17—C18	178.9 (4)
C2—C1—C6—O1	−178.7 (3)	C22—N4—C18—C19	1.3 (6)
Ni1—O3—C7—O4	174.3 (3)	Ni1—N4—C18—C19	178.0 (4)
Ni1—O3—C7—C5	−5.4 (3)	C22—N4—C18—C17	−179.9 (3)
N1—C5—C7—O4	−176.2 (3)	Ni1—N4—C18—C17	−3.1 (4)
C4—C5—C7—O4	5.3 (5)	N3—C17—C18—N4	2.7 (5)
N1—C5—C7—O3	3.4 (4)	C16—C17—C18—N4	−176.9 (4)
C4—C5—C7—O3	−175.0 (3)	N3—C17—C18—C19	−178.4 (4)
C12—N2—C8—C9	1.5 (6)	C16—C17—C18—C19	2.0 (7)
Ni1—N2—C8—C9	−172.1 (3)	N4—C18—C19—C20	−0.6 (8)
N2—C8—C9—C10	−0.8 (8)	C17—C18—C19—C20	−179.3 (5)
C8—C9—C10—C11	−0.9 (9)	C18—C19—C20—C21	−1.2 (10)
C9—C10—C11—C12	1.8 (10)	C19—C20—C21—C22	2.1 (10)
C8—N2—C12—C11	−0.4 (6)	C18—N4—C22—C21	−0.3 (6)
Ni1—N2—C12—C11	173.9 (4)	Ni1—N4—C22—C21	−176.6 (3)
C8—N2—C12—C13	179.8 (3)	C20—C21—C22—N4	−1.4 (8)
Ni1—N2—C12—C13	−5.8 (4)	C24—N5—C23—O5	177.5 (4)
C10—C11—C12—N2	−1.2 (8)	C25—N5—C23—O5	−0.7 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O2^i	0.71 (5)	2.21 (5)	2.907 (5)	172 (5)
O6—H6B···O4	0.74 (6)	2.14 (6)	2.881 (5)	175 (7)
C2—H2···O2^ii	0.94	2.49	3.254 (4)	138
C8—H8···O5^iii	0.94	2.47	3.133 (5)	128
C9—H9···O2^iv	0.94	2.55	3.465 (5)	163
C25—H25C···O4^v	0.97	2.45	3.361 (6)	157

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