Aqua­(6-meth­oxy-2-{[3-(3-meth­oxy-2-oxidobenzyl­amino)propyl­amino]meth­yl}phenolato)ethano­lnickel(II) nitrate

The title compound, [Ni(C₁₉H₂₅N₂O₄)(C₂H₆O)(H₂O)]NO₃, assembles into centrosymmetric dinuclear complexes through a pair of strong O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.046
• wR factor = 0.140
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .        400 Ang.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.20 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N3
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2     ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23    ..  O3      ..       2.61 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Aqua(6-methoxy-2-{[3-(3-methoxy-2- oxidobenzylamino)propylamino]methyl}phenolato)ethanolnickel(II) nitrate

Crystal data

[Ni(C19H25N2O4)(C2H6O)(H2O)]NO3	F(000) = 1120
Mr = 530.21	Dx = 1.411 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3041 reflections
a = 13.030 (4) Å	θ = 2.4–24.4°
b = 14.458 (4) Å	µ = 0.83 mm^−1
c = 13.484 (4) Å	T = 293 K
β = 100.776 (4)°	Block, blue
V = 2495.5 (12) Å^3	0.45 × 0.43 × 0.37 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	4387 independent reflections
Radiation source: fine-focus sealed tube	2896 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→9
Tmin = 0.706, Tmax = 0.749	k = −17→17
12688 measured reflections	l = −15→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.2037P] where P = (Fo^2 + 2Fc^2)/3
4387 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.38 e Å^−3
1 restraint	Δρmin = −0.42 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.37198 (4)	−0.03691 (3)	0.10030 (3)	0.02852 (18)
N1	0.2099 (2)	−0.0191 (2)	0.0636 (2)	0.0365 (8)
H1A	0.1899	0.0039	0.1199	0.044*
N2	0.3607 (3)	−0.1539 (2)	0.1899 (2)	0.0413 (8)
H2	0.3468	−0.1324	0.2494	0.050*
N3	0.1190 (4)	0.0417 (2)	0.3003 (4)	0.0600 (11)
O1	0.3925 (2)	0.07990 (17)	0.01759 (18)	0.0315 (6)
H1	0.403 (6)	0.076 (6)	−0.037 (4)	0.047*	0.54 (6)
O2	0.4809 (2)	0.24637 (17)	0.0531 (2)	0.0507 (8)
O3	0.5332 (2)	−0.04780 (17)	0.13067 (18)	0.0322 (6)
H3	0.554 (7)	−0.065 (6)	0.083 (6)	0.048*	0.46 (6)
O4	0.7018 (2)	0.0476 (2)	0.2194 (2)	0.0516 (8)
O5	0.0840 (4)	0.0548 (3)	0.2110 (4)	0.1157 (17)
O6	0.2146 (3)	0.0248 (3)	0.3264 (3)	0.0905 (13)
O7	0.0662 (4)	0.0489 (3)	0.3645 (3)	0.1052 (15)
O8	0.3724 (2)	0.04307 (17)	0.22745 (19)	0.0432 (7)
H8	0.3219	0.0440	0.2557	0.065*
O9	0.3699 (3)	−0.1168 (2)	−0.0284 (2)	0.0361 (7)
H22	0.423 (4)	−0.144 (3)	−0.028 (3)	0.059 (17)*
H23	0.359 (4)	−0.091 (3)	−0.082 (4)	0.072 (19)*
C1	0.1782 (3)	0.0504 (3)	−0.0171 (3)	0.0432 (10)
H1B	0.1026	0.0549	−0.0317	0.052*
H1C	0.2008	0.0299	−0.0781	0.052*
C2	0.2234 (3)	0.1438 (3)	0.0114 (3)	0.0366 (9)
C3	0.3308 (3)	0.1546 (2)	0.0227 (3)	0.0311 (9)
C4	0.3742 (3)	0.2423 (2)	0.0449 (3)	0.0363 (9)
C5	0.3125 (3)	0.3168 (3)	0.0589 (3)	0.0440 (10)
H5A	0.3421	0.3748	0.0740	0.053*
C6	0.2061 (4)	0.3040 (3)	0.0503 (3)	0.0512 (12)
H6A	0.1640	0.3536	0.0610	0.061*
C7	0.1617 (3)	0.2190 (3)	0.0261 (3)	0.0501 (11)
H7	0.0898	0.2116	0.0195	0.060*
C8	0.5322 (4)	0.3320 (3)	0.0840 (5)	0.094 (2)
H8A	0.5127	0.3774	0.0320	0.141*
H8B	0.6065	0.3231	0.0958	0.141*
H8C	0.5117	0.3529	0.1450	0.141*
C9	0.4610 (3)	−0.2066 (3)	0.2158 (3)	0.0497 (11)
H9A	0.4504	−0.2594	0.2571	0.060*
H9B	0.4796	−0.2299	0.1540	0.060*
C10	0.5491 (3)	−0.1504 (3)	0.2707 (3)	0.0453 (11)
C11	0.5855 (3)	−0.0749 (3)	0.2235 (3)	0.0351 (9)
C12	0.6712 (3)	−0.0250 (3)	0.2726 (3)	0.0406 (10)
C13	0.7201 (4)	−0.0487 (3)	0.3692 (3)	0.0562 (13)
H13	0.7779	−0.0155	0.4017	0.067*
C14	0.6827 (4)	−0.1212 (4)	0.4165 (3)	0.0655 (14)
H14	0.7144	−0.1363	0.4822	0.079*
C15	0.5990 (4)	−0.1725 (3)	0.3687 (3)	0.0596 (13)
H15	0.5754	−0.2223	0.4019	0.071*
C16	0.7849 (4)	0.1057 (4)	0.2681 (4)	0.0861 (18)
H16A	0.7662	0.1327	0.3273	0.129*
H16B	0.7969	0.1539	0.2226	0.129*
H16C	0.8473	0.0695	0.2870	0.129*
C17	0.1519 (3)	−0.1061 (3)	0.0395 (3)	0.0509 (11)
H17A	0.1741	−0.1351	−0.0179	0.061*
H17B	0.0779	−0.0924	0.0204	0.061*
C18	0.1683 (4)	−0.1729 (3)	0.1268 (4)	0.0594 (13)
H18A	0.1154	−0.2208	0.1131	0.071*
H18B	0.1575	−0.1401	0.1868	0.071*
C19	0.2744 (4)	−0.2187 (3)	0.1493 (4)	0.0585 (13)
H19A	0.2729	−0.2680	0.1979	0.070*
H19B	0.2886	−0.2465	0.0878	0.070*
C20	0.4450 (3)	0.1113 (3)	0.2699 (3)	0.0531 (12)
H20A	0.4124	0.1717	0.2598	0.064*
H20B	0.5040	0.1106	0.2355	0.064*
C21	0.4819 (4)	0.0961 (4)	0.3771 (4)	0.0877 (18)
H21A	0.4246	0.1026	0.4122	0.132*
H21B	0.5349	0.1407	0.4023	0.132*
H21C	0.5105	0.0349	0.3876	0.132*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0272 (3)	0.0287 (3)	0.0308 (3)	−0.0012 (2)	0.0083 (2)	−0.0018 (2)
N1	0.0279 (18)	0.0385 (19)	0.0447 (19)	−0.0050 (15)	0.0111 (15)	−0.0106 (15)
N2	0.048 (2)	0.0345 (18)	0.045 (2)	−0.0047 (17)	0.0172 (17)	0.0014 (15)
N3	0.075 (3)	0.039 (2)	0.078 (3)	0.004 (2)	0.044 (3)	−0.003 (2)
O1	0.0312 (15)	0.0325 (14)	0.0332 (14)	0.0069 (12)	0.0121 (13)	0.0033 (12)
O2	0.0395 (18)	0.0344 (15)	0.081 (2)	−0.0059 (14)	0.0189 (16)	−0.0073 (14)
O3	0.0302 (15)	0.0430 (16)	0.0236 (13)	0.0069 (12)	0.0058 (12)	0.0019 (12)
O4	0.0407 (18)	0.067 (2)	0.0420 (16)	−0.0103 (15)	−0.0041 (14)	0.0029 (15)
O5	0.130 (4)	0.142 (4)	0.082 (3)	0.046 (3)	0.039 (3)	−0.012 (3)
O6	0.074 (3)	0.104 (3)	0.105 (3)	−0.003 (2)	0.047 (3)	0.017 (2)
O7	0.105 (4)	0.124 (4)	0.108 (3)	0.018 (3)	0.076 (3)	0.010 (3)
O8	0.0395 (17)	0.0505 (17)	0.0423 (16)	−0.0082 (14)	0.0144 (13)	−0.0160 (13)
O9	0.0330 (18)	0.0381 (16)	0.0386 (18)	0.0019 (14)	0.0103 (14)	−0.0050 (14)
C1	0.025 (2)	0.053 (3)	0.049 (2)	0.0022 (19)	−0.0005 (19)	−0.005 (2)
C2	0.031 (2)	0.040 (2)	0.036 (2)	0.0054 (18)	−0.0002 (18)	0.0008 (17)
C3	0.034 (2)	0.030 (2)	0.029 (2)	0.0080 (18)	0.0066 (17)	0.0009 (16)
C4	0.039 (2)	0.033 (2)	0.039 (2)	0.0053 (18)	0.0117 (19)	0.0000 (17)
C5	0.053 (3)	0.033 (2)	0.045 (2)	0.009 (2)	0.007 (2)	0.0001 (19)
C6	0.049 (3)	0.044 (3)	0.059 (3)	0.024 (2)	0.009 (2)	−0.004 (2)
C7	0.032 (2)	0.053 (3)	0.063 (3)	0.018 (2)	0.006 (2)	0.001 (2)
C8	0.061 (4)	0.055 (3)	0.171 (6)	−0.022 (3)	0.033 (4)	−0.033 (4)
C9	0.064 (3)	0.034 (2)	0.053 (3)	0.008 (2)	0.016 (2)	0.013 (2)
C10	0.049 (3)	0.045 (2)	0.044 (2)	0.017 (2)	0.013 (2)	0.010 (2)
C11	0.032 (2)	0.043 (2)	0.030 (2)	0.0141 (19)	0.0077 (18)	0.0053 (18)
C12	0.033 (2)	0.054 (3)	0.034 (2)	0.014 (2)	0.0049 (18)	0.0024 (19)
C13	0.042 (3)	0.084 (4)	0.039 (2)	0.017 (3)	−0.002 (2)	0.001 (2)
C14	0.053 (3)	0.098 (4)	0.042 (3)	0.028 (3)	−0.001 (2)	0.021 (3)
C15	0.061 (3)	0.069 (3)	0.050 (3)	0.022 (3)	0.013 (2)	0.027 (2)
C16	0.067 (4)	0.114 (5)	0.070 (4)	−0.037 (4)	−0.007 (3)	0.003 (3)
C17	0.032 (2)	0.048 (3)	0.073 (3)	−0.014 (2)	0.010 (2)	−0.009 (2)
C18	0.053 (3)	0.051 (3)	0.078 (3)	−0.025 (2)	0.024 (3)	−0.005 (3)
C19	0.067 (3)	0.036 (2)	0.073 (3)	−0.015 (2)	0.016 (3)	0.002 (2)
C20	0.041 (3)	0.055 (3)	0.062 (3)	−0.001 (2)	0.007 (2)	−0.023 (2)
C21	0.074 (4)	0.115 (5)	0.067 (4)	0.025 (4)	−0.005 (3)	−0.029 (3)

Geometric parameters (Å, º)

Ni1—O8	2.067 (2)	C6—C7	1.372 (6)
Ni1—O1	2.069 (2)	C6—H6A	0.9300
Ni1—O3	2.070 (3)	C7—H7	0.9300
Ni1—O9	2.080 (3)	C8—H8A	0.9600
Ni1—N1	2.093 (3)	C8—H8B	0.9600
Ni1—N2	2.100 (3)	C8—H8C	0.9600
N1—C17	1.473 (5)	C9—C10	1.486 (6)
N1—C1	1.482 (5)	C9—H9A	0.9700
N1—H1A	0.9100	C9—H9B	0.9700
N2—C19	1.487 (5)	C10—C11	1.390 (5)
N2—C9	1.496 (5)	C10—C15	1.396 (6)
N2—H2	0.9100	C11—C12	1.389 (6)
N3—O7	1.208 (5)	C12—C13	1.382 (5)
N3—O5	1.220 (5)	C13—C14	1.364 (7)
N3—O6	1.254 (6)	C13—H13	0.9300
O1—C3	1.356 (4)	C14—C15	1.376 (7)
O1—H1	0.78 (5)	C14—H14	0.9300
O2—C4	1.376 (5)	C15—H15	0.9300
O2—C8	1.431 (5)	C16—H16A	0.9600
O3—C11	1.366 (4)	C16—H16B	0.9600
O3—H3	0.78 (5)	C16—H16C	0.9600
O4—C12	1.373 (5)	C17—C18	1.507 (6)
O4—C16	1.428 (5)	C17—H17A	0.9700
O8—C20	1.411 (5)	C17—H17B	0.9700
O8—H8	0.8200	C18—C19	1.513 (6)
O9—H22	0.80 (5)	C18—H18A	0.9700
O9—H23	0.80 (5)	C18—H18B	0.9700
C1—C2	1.495 (5)	C19—H19A	0.9700
C1—H1B	0.9700	C19—H19B	0.9700
C1—H1C	0.9700	C20—C21	1.452 (6)
C2—C7	1.387 (5)	C20—H20A	0.9700
C2—C3	1.389 (5)	C20—H20B	0.9700
C3—C4	1.397 (5)	C21—H21A	0.9600
C4—C5	1.377 (5)	C21—H21B	0.9600
C5—C6	1.383 (6)	C21—H21C	0.9600
C5—H5A	0.9300
O8—Ni1—O1	90.57 (10)	C2—C7—H7	119.8
O8—Ni1—O3	91.90 (10)	O2—C8—H8A	109.5
O1—Ni1—O3	86.56 (10)	O2—C8—H8B	109.5
O8—Ni1—O9	179.35 (13)	H8A—C8—H8B	109.5
O1—Ni1—O9	89.22 (12)	O2—C8—H8C	109.5
O3—Ni1—O9	88.70 (11)	H8A—C8—H8C	109.5
O8—Ni1—N1	88.47 (11)	H8B—C8—H8C	109.5
O1—Ni1—N1	89.91 (11)	C10—C9—N2	113.4 (3)
O3—Ni1—N1	176.46 (11)	C10—C9—H9A	108.9
O9—Ni1—N1	90.92 (12)	N2—C9—H9A	108.9
O8—Ni1—N2	87.89 (11)	C10—C9—H9B	108.9
O1—Ni1—N2	176.31 (12)	N2—C9—H9B	108.9
O3—Ni1—N2	90.14 (12)	H9A—C9—H9B	107.7
O9—Ni1—N2	92.36 (13)	C11—C10—C15	118.3 (4)
N1—Ni1—N2	93.40 (12)	C11—C10—C9	119.9 (4)
C17—N1—C1	110.8 (3)	C15—C10—C9	121.7 (4)
C17—N1—Ni1	113.6 (2)	O3—C11—C12	120.4 (3)
C1—N1—Ni1	112.8 (2)	O3—C11—C10	119.4 (4)
C17—N1—H1A	106.3	C12—C11—C10	120.2 (4)
C1—N1—H1A	106.3	O4—C12—C13	123.7 (4)
Ni1—N1—H1A	106.3	O4—C12—C11	115.8 (3)
C19—N2—C9	109.4 (3)	C13—C12—C11	120.6 (4)
C19—N2—Ni1	115.2 (3)	C14—C13—C12	119.3 (5)
C9—N2—Ni1	113.1 (2)	C14—C13—H13	120.4
C19—N2—H2	106.1	C12—C13—H13	120.4
C9—N2—H2	106.1	C13—C14—C15	121.1 (4)
Ni1—N2—H2	106.1	C13—C14—H14	119.5
O7—N3—O5	122.5 (6)	C15—C14—H14	119.5
O7—N3—O6	119.0 (5)	C14—C15—C10	120.6 (4)
O5—N3—O6	118.4 (5)	C14—C15—H15	119.7
C3—O1—Ni1	119.1 (2)	C10—C15—H15	119.7
C3—O1—H1	108 (6)	O4—C16—H16A	109.5
Ni1—O1—H1	121 (6)	O4—C16—H16B	109.5
C4—O2—C8	118.0 (3)	H16A—C16—H16B	109.5
C11—O3—Ni1	121.1 (2)	O4—C16—H16C	109.5
C11—O3—H3	118 (7)	H16A—C16—H16C	109.5
Ni1—O3—H3	111 (7)	H16B—C16—H16C	109.5
C12—O4—C16	118.6 (3)	N1—C17—C18	112.5 (3)
C20—O8—Ni1	128.7 (2)	N1—C17—H17A	109.1
C20—O8—H8	109.6	C18—C17—H17A	109.1
Ni1—O8—H8	121.1	N1—C17—H17B	109.1
Ni1—O9—H22	113 (3)	C18—C17—H17B	109.1
Ni1—O9—H23	117 (4)	H17A—C17—H17B	107.8
H22—O9—H23	105 (5)	C17—C18—C19	115.3 (4)
N1—C1—C2	112.4 (3)	C17—C18—H18A	108.4
N1—C1—H1B	109.1	C19—C18—H18A	108.4
C2—C1—H1B	109.1	C17—C18—H18B	108.4
N1—C1—H1C	109.1	C19—C18—H18B	108.4
C2—C1—H1C	109.1	H18A—C18—H18B	107.5
H1B—C1—H1C	107.9	N2—C19—C18	113.5 (3)
C7—C2—C3	119.7 (4)	N2—C19—H19A	108.9
C7—C2—C1	122.2 (4)	C18—C19—H19A	108.9
C3—C2—C1	118.1 (3)	N2—C19—H19B	108.9
O1—C3—C2	120.0 (3)	C18—C19—H19B	108.9
O1—C3—C4	120.9 (3)	H19A—C19—H19B	107.7
C2—C3—C4	119.0 (3)	O8—C20—C21	111.7 (4)
O2—C4—C5	124.2 (4)	O8—C20—H20A	109.3
O2—C4—C3	114.7 (3)	C21—C20—H20A	109.3
C5—C4—C3	121.1 (4)	O8—C20—H20B	109.3
C4—C5—C6	119.0 (4)	C21—C20—H20B	109.3
C4—C5—H5A	120.5	H20A—C20—H20B	107.9
C6—C5—H5A	120.5	C20—C21—H21A	109.5
C7—C6—C5	120.8 (4)	C20—C21—H21B	109.5
C7—C6—H6A	119.6	H21A—C21—H21B	109.5
C5—C6—H6A	119.6	C20—C21—H21C	109.5
C6—C7—C2	120.4 (4)	H21A—C21—H21C	109.5
C6—C7—H7	119.8	H21B—C21—H21C	109.5
O8—Ni1—N1—C17	−130.4 (3)	O1—C3—C4—O2	4.6 (5)
O1—Ni1—N1—C17	139.0 (3)	C2—C3—C4—O2	−179.0 (3)
O9—Ni1—N1—C17	49.8 (3)	O1—C3—C4—C5	−174.2 (3)
N2—Ni1—N1—C17	−42.6 (3)	C2—C3—C4—C5	2.2 (6)
O8—Ni1—N1—C1	102.4 (2)	O2—C4—C5—C6	−179.0 (4)
O1—Ni1—N1—C1	11.8 (2)	C3—C4—C5—C6	−0.3 (6)
O9—Ni1—N1—C1	−77.4 (2)	C4—C5—C6—C7	−1.3 (6)
N2—Ni1—N1—C1	−169.8 (2)	C5—C6—C7—C2	1.0 (6)
O8—Ni1—N2—C19	128.1 (3)	C3—C2—C7—C6	0.9 (6)
O3—Ni1—N2—C19	−140.0 (3)	C1—C2—C7—C6	−178.7 (4)
O9—Ni1—N2—C19	−51.3 (3)	C19—N2—C9—C10	−171.6 (3)
N1—Ni1—N2—C19	39.7 (3)	Ni1—N2—C9—C10	58.5 (4)
O8—Ni1—N2—C9	−105.0 (3)	N2—C9—C10—C11	−64.1 (5)
O3—Ni1—N2—C9	−13.2 (3)	N2—C9—C10—C15	117.5 (4)
O9—Ni1—N2—C9	75.5 (3)	Ni1—O3—C11—C12	−131.5 (3)
N1—Ni1—N2—C9	166.6 (3)	Ni1—O3—C11—C10	45.4 (4)
O8—Ni1—O1—C3	−48.2 (3)	C15—C10—C11—O3	−175.1 (4)
O3—Ni1—O1—C3	−140.0 (3)	C9—C10—C11—O3	6.4 (5)
O9—Ni1—O1—C3	131.2 (3)	C15—C10—C11—C12	1.7 (6)
N1—Ni1—O1—C3	40.3 (3)	C9—C10—C11—C12	−176.8 (4)
O8—Ni1—O3—C11	50.9 (3)	C16—O4—C12—C13	−3.7 (6)
O1—Ni1—O3—C11	141.3 (3)	C16—O4—C12—C11	175.7 (4)
O9—Ni1—O3—C11	−129.4 (3)	O3—C11—C12—O4	−3.8 (5)
N2—Ni1—O3—C11	−37.0 (3)	C10—C11—C12—O4	179.4 (3)
O1—Ni1—O8—C20	−49.9 (3)	O3—C11—C12—C13	175.7 (3)
O3—Ni1—O8—C20	36.6 (3)	C10—C11—C12—C13	−1.1 (6)
N1—Ni1—O8—C20	−139.8 (3)	O4—C12—C13—C14	178.9 (4)
N2—Ni1—O8—C20	126.7 (3)	C11—C12—C13—C14	−0.6 (6)
C17—N1—C1—C2	171.5 (3)	C12—C13—C14—C15	1.6 (7)
Ni1—N1—C1—C2	−59.8 (4)	C13—C14—C15—C10	−1.0 (7)
N1—C1—C2—C7	−113.5 (4)	C11—C10—C15—C14	−0.7 (7)
N1—C1—C2—C3	66.9 (5)	C9—C10—C15—C14	177.7 (4)
Ni1—O1—C3—C2	−48.2 (4)	C1—N1—C17—C18	−170.5 (3)
Ni1—O1—C3—C4	128.2 (3)	Ni1—N1—C17—C18	61.3 (4)
C7—C2—C3—O1	174.0 (3)	N1—C17—C18—C19	−72.8 (5)
C1—C2—C3—O1	−6.4 (5)	C9—N2—C19—C18	176.4 (4)
C7—C2—C3—C4	−2.4 (5)	Ni1—N2—C19—C18	−54.8 (4)
C1—C2—C3—C4	177.2 (3)	C17—C18—C19—N2	68.8 (5)
C8—O2—C4—C5	3.9 (6)	Ni1—O8—C20—C21	−129.2 (3)
C8—O2—C4—C3	−174.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5	0.91	2.14	3.001 (5)	157
O8—H8···O6	0.82	1.85	2.665 (5)	170
O3—H3···O1^i	0.78 (5)	1.65 (5)	2.423 (3)	169 (10)
O1—H1···O3^i	0.78 (5)	1.68 (5)	2.423 (3)	158 (9)
O9—H22···O1^i	0.80 (5)	2.55 (5)	3.118 (4)	129 (4)
O9—H22···O2^i	0.80 (5)	2.00 (5)	2.764 (4)	159 (4)
O9—H23···O4^i	0.80 (5)	1.98 (5)	2.758 (4)	165 (5)
O9—H23···O3^i	0.80 (5)	2.61 (5)	3.132 (4)	125 (4)

Symmetry code: (i) −x+1, −y, −z.