Bis[1,3-dihydr­oxy-2-hydroxy­methyl-2-(5-nitro-2-oxidobenzylideneamino)propane-κ³N,O,O′]nickel(II) pyridine solvate

The Ni^II atom in the title complex, [Ni(C₁₁H₁₃N₂O₆)₂]·C₅H₅N, is chelated by a terdentate Schiff base anion in a slightly octa­hedral geometry. One of the coordinated hydroxyl groups forms a hydrogen bond with the pyridine solvent mol­ecule. In the crystal structure, other hydroxyl groups are involved in inter­molecular hydrogen bonding, forming a two-dimensional layer.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.097
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H5O    ..  H6O     ..       2.09 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.675     0.824
            Tmin(prime) and Tmax expected:      0.758     0.818
            RR(prime) =      0.884
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.86 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.38 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.17
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O12  -H12O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O12  -H12O    1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Bis[1,3-dihydroxy-2-hydroxymethyl-2-(5-nitrosalicylidimino)propane- κ³N,O,O']nickel(II) pyridine solvate

Crystal data

[Ni(C11H13N2O6)2]·C5H5N	F(000) = 1408
Mr = 676.28	Dx = 1.612 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8347 reflections
a = 11.2465 (1) Å	θ = 2.6–35.5°
b = 11.4857 (2) Å	µ = 0.77 mm^−1
c = 21.9861 (3) Å	T = 173 K
β = 101.105 (1)°	Prism, green
V = 2786.85 (7) Å^3	0.35 × 0.31 × 0.26 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer	6373 independent reflections
Radiation source: fine-focus sealed tube	6017 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.675, Tmax = 0.824	k = −14→14
39058 measured reflections	l = −28→28

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 2.8761P] where P = (Fo^2 + 2Fc^2)/3
6373 reflections	(Δ/σ)max = 0.001
430 parameters	Δρmax = 0.72 e Å^−3
6 restraints	Δρmin = −0.81 e Å^−3

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

	x	y	z	Uiso*/Ueq
Ni1	0.225342 (17)	0.576195 (18)	0.759261 (9)	0.00804 (7)
O1	0.17355 (10)	0.48595 (10)	0.67963 (5)	0.0113 (2)
O2	0.29775 (15)	0.49661 (16)	0.41497 (7)	0.0323 (4)
O3	0.44317 (12)	0.60418 (12)	0.46432 (6)	0.0191 (3)
O4	0.30077 (11)	0.67934 (12)	0.83459 (6)	0.0151 (3)
H4O	0.289 (3)	0.687 (3)	0.8715 (6)	0.040 (8)*
O5	0.61378 (11)	0.49538 (11)	0.80060 (7)	0.0175 (3)
H5O	0.573 (2)	0.4363 (15)	0.7861 (11)	0.024 (6)*
O6	0.53580 (11)	0.82090 (11)	0.72441 (6)	0.0149 (2)
H6O	0.5955 (17)	0.858 (2)	0.7158 (13)	0.036 (7)*
O7	0.27830 (11)	0.42590 (10)	0.80612 (6)	0.0115 (2)
O8	0.26526 (12)	0.27552 (12)	1.07656 (6)	0.0195 (3)
O9	0.11223 (13)	0.39360 (14)	1.06000 (6)	0.0250 (3)
O10	0.13101 (10)	0.72105 (10)	0.71321 (6)	0.0116 (2)
H10O	0.141 (3)	0.7855 (15)	0.7317 (12)	0.040 (8)*
O11	−0.01863 (11)	0.79973 (11)	0.81303 (6)	0.0162 (3)
H11O	−0.065 (2)	0.8570 (16)	0.8159 (12)	0.028 (7)*
O12	−0.17022 (11)	0.45538 (11)	0.76420 (6)	0.0151 (3)
H12O	−0.2296 (19)	0.485 (3)	0.7773 (14)	0.044 (8)*
N1	0.35195 (15)	0.54397 (14)	0.46283 (7)	0.0177 (3)
N2	0.38896 (12)	0.61374 (12)	0.73787 (6)	0.0094 (3)
N3	0.19560 (14)	0.34090 (13)	1.04244 (7)	0.0150 (3)
N4	0.06541 (12)	0.56291 (12)	0.78799 (7)	0.0092 (3)
N5	0.25502 (15)	0.69332 (14)	0.94831 (7)	0.0183 (3)
C1	0.21814 (15)	0.50111 (14)	0.63022 (8)	0.0110 (3)
C2	0.14988 (16)	0.46495 (15)	0.57167 (8)	0.0144 (3)
H2	0.0721	0.4315	0.5702	0.017*
C3	0.19232 (16)	0.47675 (16)	0.51747 (8)	0.0157 (3)
H3	0.1452	0.4507	0.4793	0.019*
C4	0.30585 (16)	0.52755 (16)	0.51920 (8)	0.0143 (3)
C5	0.37610 (16)	0.56374 (15)	0.57456 (8)	0.0134 (3)
H5	0.4535	0.5969	0.5748	0.016*
C6	0.33492 (15)	0.55219 (15)	0.63013 (8)	0.0115 (3)
C7	0.41624 (15)	0.59771 (14)	0.68463 (8)	0.0110 (3)
H7	0.4963	0.6171	0.6803	0.013*
C8	0.47847 (14)	0.66573 (14)	0.78906 (8)	0.0104 (3)
C9	0.40514 (15)	0.74242 (15)	0.82567 (8)	0.0129 (3)
H9A	0.4554	0.7633	0.8663	0.015*
H9B	0.3803	0.8151	0.8025	0.015*
C10	0.54011 (15)	0.56721 (15)	0.83122 (8)	0.0133 (3)
H10A	0.5909	0.6016	0.8687	0.016*
H10B	0.4772	0.5186	0.8447	0.016*
C11	0.58028 (14)	0.73567 (15)	0.76996 (8)	0.0125 (3)
H11A	0.6279	0.7746	0.8069	0.015*
H11B	0.6351	0.6820	0.7534	0.015*
C12	0.25370 (15)	0.40369 (14)	0.86026 (8)	0.0102 (3)
C13	0.33035 (15)	0.32819 (15)	0.90176 (8)	0.0150 (3)
H13	0.3969	0.2922	0.8884	0.018*
C14	0.31135 (16)	0.30571 (16)	0.96041 (8)	0.0153 (3)
H14	0.3643	0.2557	0.9875	0.018*
C15	0.21227 (15)	0.35802 (15)	0.97961 (8)	0.0130 (3)
C16	0.13164 (15)	0.42791 (14)	0.94016 (8)	0.0117 (3)
H16	0.0636	0.4601	0.9539	0.014*
C17	0.14974 (14)	0.45127 (14)	0.88034 (7)	0.0096 (3)
C18	0.05670 (14)	0.52161 (14)	0.84104 (8)	0.0105 (3)
H18	−0.0154	0.5378	0.8560	0.013*
C19	−0.03984 (14)	0.62406 (14)	0.75083 (7)	0.0098 (3)
C20	0.00515 (15)	0.68865 (16)	0.69746 (8)	0.0131 (3)
H20A	−0.0072	0.6378	0.6604	0.016*
H20B	−0.0443	0.7597	0.6866	0.016*
C21	−0.10118 (14)	0.71033 (14)	0.78774 (8)	0.0116 (3)
H21A	−0.1724	0.7453	0.7603	0.014*
H21B	−0.1299	0.6689	0.8217	0.014*
C22	−0.13292 (15)	0.53186 (15)	0.72051 (8)	0.0130 (3)
H22A	−0.2051	0.5722	0.6969	0.016*
H22B	−0.0968	0.4853	0.6908	0.016*
C23	0.14957 (17)	0.73336 (17)	0.95890 (9)	0.0200 (4)
H23	0.0928	0.7645	0.9252	0.024*
C24	0.11936 (19)	0.73142 (19)	1.01731 (10)	0.0256 (4)
H24	0.0436	0.7610	1.0233	0.031*
C25	0.2010 (2)	0.6859 (2)	1.06627 (10)	0.0296 (5)
H25	0.1827	0.6836	1.1067	0.035*
C26	0.3104 (2)	0.64339 (19)	1.05543 (10)	0.0286 (5)
H26	0.3683	0.6109	1.0882	0.034*
C27	0.33360 (19)	0.64913 (18)	0.99622 (10)	0.0231 (4)
H27	0.4089	0.6204	0.9891	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.00587 (11)	0.00800 (12)	0.01086 (12)	−0.00021 (7)	0.00310 (8)	0.00009 (7)
O1	0.0107 (5)	0.0102 (6)	0.0136 (6)	−0.0020 (4)	0.0042 (4)	−0.0007 (4)
O2	0.0365 (9)	0.0475 (10)	0.0129 (7)	−0.0063 (7)	0.0051 (6)	−0.0067 (6)
O3	0.0199 (6)	0.0208 (7)	0.0189 (6)	0.0053 (5)	0.0095 (5)	0.0048 (5)
O4	0.0121 (6)	0.0200 (6)	0.0152 (6)	−0.0061 (5)	0.0079 (5)	−0.0062 (5)
O5	0.0102 (6)	0.0129 (6)	0.0302 (7)	0.0006 (5)	0.0060 (5)	0.0004 (5)
O6	0.0100 (6)	0.0135 (6)	0.0222 (6)	−0.0017 (5)	0.0058 (5)	0.0051 (5)
O7	0.0103 (5)	0.0113 (6)	0.0139 (6)	0.0027 (4)	0.0049 (4)	0.0013 (4)
O8	0.0228 (7)	0.0191 (7)	0.0148 (6)	−0.0022 (5)	−0.0012 (5)	0.0050 (5)
O9	0.0236 (7)	0.0361 (8)	0.0176 (7)	0.0061 (6)	0.0101 (5)	0.0036 (6)
O10	0.0087 (5)	0.0094 (6)	0.0176 (6)	0.0003 (4)	0.0048 (4)	0.0007 (4)
O11	0.0113 (6)	0.0099 (6)	0.0270 (7)	0.0005 (5)	0.0025 (5)	−0.0041 (5)
O12	0.0104 (6)	0.0106 (6)	0.0258 (7)	−0.0006 (5)	0.0068 (5)	0.0004 (5)
N1	0.0218 (8)	0.0188 (8)	0.0129 (7)	0.0065 (6)	0.0047 (6)	0.0019 (6)
N2	0.0066 (6)	0.0088 (6)	0.0129 (6)	0.0006 (5)	0.0020 (5)	0.0010 (5)
N3	0.0154 (7)	0.0149 (7)	0.0141 (7)	−0.0044 (6)	0.0015 (5)	0.0012 (5)
N4	0.0067 (6)	0.0074 (6)	0.0137 (7)	0.0011 (5)	0.0025 (5)	0.0000 (5)
N5	0.0217 (8)	0.0174 (8)	0.0168 (7)	−0.0079 (6)	0.0060 (6)	−0.0035 (6)
C1	0.0115 (7)	0.0074 (7)	0.0146 (8)	0.0024 (6)	0.0036 (6)	0.0012 (6)
C2	0.0124 (8)	0.0141 (8)	0.0163 (8)	−0.0017 (6)	0.0018 (6)	−0.0012 (6)
C3	0.0182 (8)	0.0142 (8)	0.0134 (8)	0.0011 (7)	−0.0004 (6)	−0.0016 (6)
C4	0.0169 (8)	0.0144 (8)	0.0126 (8)	0.0037 (7)	0.0050 (6)	0.0005 (6)
C5	0.0127 (8)	0.0121 (8)	0.0164 (8)	0.0027 (6)	0.0052 (6)	0.0001 (6)
C6	0.0112 (7)	0.0111 (7)	0.0126 (8)	0.0009 (6)	0.0033 (6)	−0.0004 (6)
C7	0.0080 (7)	0.0099 (7)	0.0156 (8)	−0.0003 (6)	0.0037 (6)	0.0003 (6)
C8	0.0083 (7)	0.0101 (7)	0.0131 (7)	−0.0015 (6)	0.0024 (6)	−0.0007 (6)
C9	0.0108 (7)	0.0123 (8)	0.0169 (8)	−0.0032 (6)	0.0058 (6)	−0.0036 (6)
C10	0.0099 (7)	0.0140 (8)	0.0155 (8)	−0.0007 (6)	0.0011 (6)	0.0014 (6)
C11	0.0077 (7)	0.0141 (8)	0.0160 (8)	−0.0012 (6)	0.0026 (6)	0.0010 (6)
C12	0.0096 (7)	0.0074 (7)	0.0140 (8)	−0.0010 (6)	0.0031 (6)	−0.0009 (6)
C13	0.0125 (8)	0.0146 (8)	0.0186 (8)	0.0055 (6)	0.0050 (6)	0.0022 (6)
C14	0.0127 (8)	0.0151 (8)	0.0175 (8)	0.0020 (6)	0.0012 (6)	0.0030 (6)
C15	0.0138 (8)	0.0133 (8)	0.0121 (7)	−0.0026 (6)	0.0029 (6)	0.0008 (6)
C16	0.0106 (7)	0.0115 (8)	0.0137 (8)	−0.0027 (6)	0.0038 (6)	−0.0009 (6)
C17	0.0081 (7)	0.0076 (7)	0.0134 (7)	−0.0008 (6)	0.0027 (6)	0.0004 (6)
C18	0.0078 (7)	0.0096 (7)	0.0149 (7)	−0.0005 (6)	0.0038 (6)	−0.0012 (6)
C19	0.0072 (7)	0.0097 (7)	0.0129 (7)	0.0007 (6)	0.0026 (6)	0.0010 (6)
C20	0.0085 (7)	0.0159 (8)	0.0154 (8)	0.0012 (6)	0.0031 (6)	0.0035 (6)
C21	0.0081 (7)	0.0098 (7)	0.0172 (8)	0.0019 (6)	0.0034 (6)	0.0000 (6)
C22	0.0107 (7)	0.0125 (8)	0.0155 (8)	−0.0003 (6)	0.0015 (6)	−0.0005 (6)
C23	0.0206 (9)	0.0177 (9)	0.0214 (9)	−0.0061 (7)	0.0030 (7)	−0.0021 (7)
C24	0.0255 (10)	0.0230 (10)	0.0320 (11)	−0.0088 (8)	0.0154 (8)	−0.0094 (8)
C25	0.0460 (13)	0.0268 (11)	0.0189 (9)	−0.0160 (10)	0.0139 (9)	−0.0037 (8)
C26	0.0391 (12)	0.0209 (10)	0.0223 (10)	−0.0061 (9)	−0.0031 (8)	0.0050 (8)
C27	0.0230 (9)	0.0168 (9)	0.0290 (10)	−0.0029 (7)	0.0037 (8)	−0.0020 (8)

Geometric parameters (Å, º)

Ni1—O1	2.021 (1)	C6—C7	1.457 (2)
Ni1—O4	2.080 (1)	C7—H7	0.9500
Ni1—O7	2.040 (1)	C8—C11	1.523 (2)
Ni1—O10	2.123 (1)	C8—C9	1.536 (2)
Ni1—N2	2.031 (1)	C8—C10	1.540 (2)
Ni1—N4	2.024 (1)	C9—H9A	0.9900
O1—C1	1.293 (2)	C9—H9B	0.9900
O2—N1	1.236 (2)	C10—H10A	0.9900
O3—N1	1.232 (2)	C10—H10B	0.9900
O4—C9	1.4247 (19)	C11—H11A	0.9900
O4—H4O	0.853 (10)	C11—H11B	0.9900
O5—C10	1.427 (2)	C12—C13	1.423 (2)
O5—H5O	0.848 (10)	C12—C17	1.435 (2)
O6—C11	1.421 (2)	C13—C14	1.372 (2)
O6—H6O	0.845 (10)	C13—H13	0.9500
O7—C12	1.298 (2)	C14—C15	1.401 (2)
O8—N3	1.230 (2)	C14—H14	0.9500
O9—N3	1.238 (2)	C15—C16	1.384 (2)
O10—C20	1.440 (2)	C16—C17	1.395 (2)
O10—H10O	0.842 (10)	C16—H16	0.9500
O11—C21	1.424 (2)	C17—C18	1.465 (2)
O11—H11O	0.847 (10)	C18—H18	0.9500
O12—C22	1.423 (2)	C19—C21	1.527 (2)
O12—H12O	0.850 (10)	C19—C22	1.547 (2)
N1—C4	1.445 (2)	C19—C20	1.553 (2)
N2—C7	1.279 (2)	C20—H20A	0.9900
N2—C8	1.483 (2)	C20—H20B	0.9900
N3—C15	1.443 (2)	C21—H21A	0.9900
N4—C18	1.280 (2)	C21—H21B	0.9900
N4—C19	1.480 (2)	C22—H22A	0.9900
N5—C23	1.334 (3)	C22—H22B	0.9900
N5—C27	1.338 (3)	C23—C24	1.390 (3)
C1—C2	1.428 (2)	C23—H23	0.9500
C1—C6	1.439 (2)	C24—C25	1.376 (3)
C2—C3	1.373 (2)	C24—H24	0.9500
C2—H2	0.9500	C25—C26	1.386 (3)
C3—C4	1.398 (3)	C25—H25	0.9500
C3—H3	0.9500	C26—C27	1.378 (3)
C4—C5	1.381 (2)	C26—H26	0.9500
C5—C6	1.394 (2)	C27—H27	0.9500
C5—H5	0.9500
O1—Ni1—O4	170.81 (5)	O5—C10—C8	112.07 (14)
O1—Ni1—O7	90.63 (5)	O5—C10—H10A	109.2
O1—Ni1—O10	87.40 (5)	C8—C10—H10A	109.2
O1—Ni1—N2	91.79 (5)	O5—C10—H10B	109.2
O1—Ni1—N4	96.11 (5)	C8—C10—H10B	109.2
O4—Ni1—O7	92.59 (5)	H10A—C10—H10B	107.9
O4—Ni1—O10	91.32 (5)	O6—C11—C8	112.12 (13)
O4—Ni1—N2	79.32 (5)	O6—C11—H11A	109.2
O4—Ni1—N4	92.59 (5)	C8—C11—H11A	109.2
O7—Ni1—O10	167.14 (5)	O6—C11—H11B	109.2
O7—Ni1—N2	96.15 (5)	C8—C11—H11B	109.2
O7—Ni1—N4	88.23 (5)	H11A—C11—H11B	107.9
N2—Ni1—N4	170.93 (6)	O7—C12—C13	119.86 (15)
O10—Ni1—N2	96.60 (5)	O7—C12—C17	122.50 (15)
O10—Ni1—N4	79.36 (5)	C13—C12—C17	117.63 (15)
C1—O1—Ni1	124.40 (11)	C14—C13—C12	122.19 (16)
C9—O4—Ni1	113.61 (10)	C14—C13—H13	118.9
C9—O4—H4O	111 (2)	C12—C13—H13	118.9
Ni1—O4—H4O	135 (2)	C13—C14—C15	118.66 (16)
C10—O5—H5O	108.3 (18)	C13—C14—H14	120.7
C11—O6—H6O	108.3 (19)	C15—C14—H14	120.7
C12—O7—Ni1	122.44 (10)	C16—C15—C14	121.54 (16)
C20—O10—Ni1	106.86 (9)	C16—C15—N3	119.25 (15)
C20—O10—H10O	112 (2)	C14—C15—N3	119.19 (15)
Ni1—O10—H10O	117 (2)	C15—C16—C17	120.35 (16)
C21—O11—H11O	103.1 (18)	C15—C16—H16	119.8
C22—O12—H12O	109 (2)	C17—C16—H16	119.8
O3—N1—O2	122.75 (16)	C16—C17—C12	119.49 (15)
O3—N1—C4	119.01 (15)	C16—C17—C18	116.40 (14)
O2—N1—C4	118.24 (16)	C12—C17—C18	124.09 (15)
C7—N2—C8	120.33 (14)	N4—C18—C17	124.77 (15)
C7—N2—Ni1	124.67 (12)	N4—C18—H18	117.6
C8—N2—Ni1	114.99 (10)	C17—C18—H18	117.6
O8—N3—O9	122.65 (15)	N4—C19—C21	114.20 (13)
O8—N3—C15	118.81 (15)	N4—C19—C22	108.42 (13)
O9—N3—C15	118.53 (15)	C21—C19—C22	109.62 (13)
C18—N4—C19	119.04 (14)	N4—C19—C20	107.55 (13)
C18—N4—Ni1	122.74 (11)	C21—C19—C20	109.75 (13)
C19—N4—Ni1	117.16 (10)	C22—C19—C20	107.05 (13)
C23—N5—C27	117.92 (17)	O10—C20—C19	112.95 (13)
O1—C1—C2	119.35 (15)	O10—C20—H20A	109.0
O1—C1—C6	123.91 (15)	C19—C20—H20A	109.0
C2—C1—C6	116.73 (15)	O10—C20—H20B	109.0
C3—C2—C1	122.51 (16)	C19—C20—H20B	109.0
C3—C2—H2	118.7	H20A—C20—H20B	107.8
C1—C2—H2	118.7	O11—C21—C19	110.38 (13)
C2—C3—C4	119.08 (16)	O11—C21—H21A	109.6
C2—C3—H3	120.5	C19—C21—H21A	109.6
C4—C3—H3	120.5	O11—C21—H21B	109.6
C5—C4—C3	120.93 (16)	C19—C21—H21B	109.6
C5—C4—N1	118.53 (16)	H21A—C21—H21B	108.1
C3—C4—N1	120.53 (16)	O12—C22—C19	113.24 (14)
C4—C5—C6	120.90 (16)	O12—C22—H22A	108.9
C4—C5—H5	119.6	C19—C22—H22A	108.9
C6—C5—H5	119.6	O12—C22—H22B	108.9
C5—C6—C1	119.84 (15)	C19—C22—H22B	108.9
C5—C6—C7	115.14 (15)	H22A—C22—H22B	107.7
C1—C6—C7	125.00 (15)	N5—C23—C24	122.65 (19)
N2—C7—C6	125.52 (15)	N5—C23—H23	118.7
N2—C7—H7	117.2	C24—C23—H23	118.7
C6—C7—H7	117.2	C25—C24—C23	118.9 (2)
N2—C8—C11	116.08 (13)	C25—C24—H24	120.5
N2—C8—C9	105.90 (13)	C23—C24—H24	120.5
C11—C8—C9	110.50 (14)	C24—C25—C26	118.66 (19)
N2—C8—C10	108.77 (13)	C24—C25—H25	120.7
C11—C8—C10	106.16 (13)	C26—C25—H25	120.7
C9—C8—C10	109.31 (14)	C27—C26—C25	118.8 (2)
O4—C9—C8	108.68 (13)	C27—C26—H26	120.6
O4—C9—H9A	110.0	C25—C26—H26	120.6
C8—C9—H9A	110.0	N5—C27—C26	123.1 (2)
O4—C9—H9B	110.0	N5—C27—H27	118.5
C8—C9—H9B	110.0	C26—C27—H27	118.5
H9A—C9—H9B	108.3
N4—Ni1—O1—C1	151.96 (13)	C7—N2—C8—C9	143.96 (15)
N2—Ni1—O1—C1	−23.58 (13)	Ni1—N2—C8—C9	−34.66 (15)
O7—Ni1—O1—C1	−119.75 (13)	C7—N2—C8—C10	−98.65 (17)
O10—Ni1—O1—C1	72.96 (13)	Ni1—N2—C8—C10	82.74 (14)
N4—Ni1—O4—C9	−161.62 (11)	Ni1—O4—C9—C8	−36.86 (16)
N2—Ni1—O4—C9	14.26 (11)	N2—C8—C9—O4	44.95 (17)
O7—Ni1—O4—C9	110.03 (11)	C11—C8—C9—O4	171.43 (13)
O10—Ni1—O4—C9	−82.22 (11)	C10—C8—C9—O4	−72.08 (17)
N4—Ni1—O7—C12	−40.27 (13)	N2—C8—C10—O5	67.14 (17)
O1—Ni1—O7—C12	−136.36 (12)	C11—C8—C10—O5	−58.45 (17)
N2—Ni1—O7—C12	131.77 (13)	C9—C8—C10—O5	−177.66 (13)
O4—Ni1—O7—C12	52.24 (13)	N2—C8—C11—O6	51.46 (19)
O10—Ni1—O7—C12	−55.3 (3)	C9—C8—C11—O6	−69.12 (18)
N4—Ni1—O10—C20	−33.69 (10)	C10—C8—C11—O6	172.46 (13)
O1—Ni1—O10—C20	63.02 (10)	Ni1—O7—C12—C13	−153.42 (13)
N2—Ni1—O10—C20	154.52 (10)	Ni1—O7—C12—C17	27.5 (2)
O7—Ni1—O10—C20	−18.4 (3)	O7—C12—C13—C14	177.22 (16)
O4—Ni1—O10—C20	−126.08 (10)	C17—C12—C13—C14	−3.7 (3)
O1—Ni1—N2—C7	11.98 (14)	C12—C13—C14—C15	0.7 (3)
O7—Ni1—N2—C7	102.81 (14)	C13—C14—C15—C16	2.3 (3)
O4—Ni1—N2—C7	−165.71 (15)	C13—C14—C15—N3	−176.18 (16)
O10—Ni1—N2—C7	−75.61 (14)	O8—N3—C15—C16	177.58 (15)
O1—Ni1—N2—C8	−169.47 (11)	O9—N3—C15—C16	−3.1 (2)
O7—Ni1—N2—C8	−78.65 (11)	O8—N3—C15—C14	−3.9 (2)
O4—Ni1—N2—C8	12.84 (11)	O9—N3—C15—C14	175.43 (17)
O10—Ni1—N2—C8	102.94 (11)	C14—C15—C16—C17	−2.2 (3)
O1—Ni1—N4—C18	125.17 (13)	N3—C15—C16—C17	176.29 (15)
O7—Ni1—N4—C18	34.73 (14)	C15—C16—C17—C12	−0.9 (2)
O4—Ni1—N4—C18	−57.79 (14)	C15—C16—C17—C18	177.26 (15)
O10—Ni1—N4—C18	−148.65 (14)	O7—C12—C17—C16	−177.19 (15)
O1—Ni1—N4—C19	−66.71 (11)	C13—C12—C17—C16	3.7 (2)
O7—Ni1—N4—C19	−157.15 (11)	O7—C12—C17—C18	4.8 (3)
O4—Ni1—N4—C19	110.34 (11)	C13—C12—C17—C18	−174.31 (15)
O10—Ni1—N4—C19	19.48 (11)	C19—N4—C18—C17	174.81 (15)
Ni1—O1—C1—C2	−158.34 (12)	Ni1—N4—C18—C17	−17.3 (2)
Ni1—O1—C1—C6	22.2 (2)	C16—C17—C18—N4	171.26 (16)
O1—C1—C2—C3	−179.00 (16)	C12—C17—C18—N4	−10.6 (3)
C6—C1—C2—C3	0.5 (3)	C18—N4—C19—C21	44.9 (2)
C1—C2—C3—C4	−1.0 (3)	Ni1—N4—C19—C21	−123.64 (12)
C2—C3—C4—C5	1.2 (3)	C18—N4—C19—C22	−77.57 (18)
C2—C3—C4—N1	−178.44 (16)	Ni1—N4—C19—C22	113.84 (12)
O3—N1—C4—C5	−10.4 (2)	C18—N4—C19—C20	166.99 (15)
O2—N1—C4—C5	169.58 (17)	Ni1—N4—C19—C20	−1.59 (16)
O3—N1—C4—C3	169.24 (16)	Ni1—O10—C20—C19	43.21 (15)
O2—N1—C4—C3	−10.8 (3)	N4—C19—C20—O10	−28.37 (18)
C3—C4—C5—C6	−1.0 (3)	C21—C19—C20—O10	96.40 (16)
N1—C4—C5—C6	178.66 (15)	C22—C19—C20—O10	−144.71 (14)
C4—C5—C6—C1	0.5 (3)	N4—C19—C21—O11	61.49 (18)
C4—C5—C6—C7	−177.88 (16)	C22—C19—C21—O11	−176.64 (13)
O1—C1—C6—C5	179.22 (15)	C20—C19—C21—O11	−59.34 (17)
C2—C1—C6—C5	−0.2 (2)	N4—C19—C22—O12	56.44 (17)
O1—C1—C6—C7	−2.6 (3)	C21—C19—C22—O12	−68.82 (17)
C2—C1—C6—C7	177.97 (16)	C20—C19—C22—O12	172.20 (13)
C8—N2—C7—C6	−177.25 (15)	C27—N5—C23—C24	0.4 (3)
Ni1—N2—C7—C6	1.2 (2)	N5—C23—C24—C25	−0.4 (3)
C5—C6—C7—N2	167.84 (16)	C23—C24—C25—C26	−0.1 (3)
C1—C6—C7—N2	−10.5 (3)	C24—C25—C26—C27	0.5 (3)
C7—N2—C8—C11	20.9 (2)	C23—N5—C27—C26	0.0 (3)
Ni1—N2—C8—C11	−157.67 (11)	C25—C26—C27—N5	−0.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4o···N5	0.85 (1)	1.80 (1)	2.653 (2)	175 (3)
O4—H4o···N5	0.85 (1)	1.80 (1)	2.653 (2)	175 (3)
O5—H5o···O6^i	0.85 (1)	1.79 (1)	2.606 (2)	162 (3)
O6—H6o···O7^ii	0.85 (1)	1.77 (1)	2.611 (2)	176 (3)
O10—H10o···O12^iii	0.84 (1)	1.98 (2)	2.757 (2)	153 (3)
O11—H11o···O1^iii	0.85 (1)	1.94 (1)	2.783 (2)	178 (3)
O12—H12o···O5^iv	0.85 (1)	1.93 (2)	2.739 (2)	159 (3)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x, y+1/2, −z+3/2; (iv) x−1, y, z.