trans-Di­aqua­bis­[4-(4-methyl­phenyl)-3,5-bis(2-pyridyl)-4H-1,2,4-triazole]­nickel(II) diperchlorate tetrahydrate

In the title centrosymmetric mononuclear nickel(II) compound, [Ni(C₁₉H₁₅N₅)₂(H₂O)₂](ClO₄)₂·4H₂O, the central Ni^II atom is coordinated by four N atoms from two 4-(4-methyl­phenyl)-3,5-bis(2-pyridyl)-4H-1,2,4-triazole ligands, and two O atoms from two water mol­ecules. The coordination geometry is slightly distorted octahedral. In the crystal structure, the mol­ecules are linked together by intermolecular O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• H-atom completeness 91%
• Disorder in solvent or counterion
• R factor = 0.065
• wR factor = 0.171
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         41 Perc.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT221_ALERT_4_C Large Solvent/Anion  O     Ueq(max)/Ueq(min) ...       3.94 Ratio
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for        Cl1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      27.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT432_ALERT_2_C Short Inter X...Y Contact  C1     ..  O4B     ..       2.92 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT731_ALERT_1_C Bond    Calc     0.86(6), Rep     0.86(2) ......       3.00 su-Rat
              O3W  -H3WA    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(6), Rep     0.86(2) ......       3.00 su-Rat
              O3W  -H4#     1.555   1.555

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C38 H42 Cl2 N10 Ni1 O14
            Atom count from the _atom_site data:  C38 H38 Cl2 N10 Ni1 O14
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C38 H42 Cl2 N10 Ni O14
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         76.00     76.00    0.00
           H         84.00     76.00    8.00
           Cl         4.00      4.00    0.00
           N         20.00     20.00    0.00
           Ni         2.00      2.00    0.00
           O         28.00     28.00    0.00

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

   8 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
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; 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.

trans-Diaquabis[4-(4-methylphenyl)-3,5-bis(2-pyridyl)-4H-1,2,4- triazole]nickel(II) diperchlorate tetrahydrate

Crystal data

[Ni(C19H15N5)2(H2O)2](ClO4)2·4H2O	F(000) = 1028
Mr = 988.39	Dx = 1.441 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12113 reflections
a = 9.139 (3) Å	θ = 4.2–28.3°
b = 15.480 (6) Å	µ = 0.62 mm^−1
c = 16.240 (6) Å	T = 293 K
β = 95.168 (7)°	Block, blue
V = 2288.2 (14) Å^3	0.20 × 0.15 × 0.09 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	4035 independent reflections
Radiation source: fine-focus sealed tube	1637 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→7
Tmin = 0.887, Tmax = 0.947	k = −18→18
11832 measured reflections	l = −19→18

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 0.84	w = 1/[σ^2(Fo^2) + (0.079P)^2] where P = (Fo^2 + 2Fc^2)/3
4035 reflections	(Δ/σ)max = 0.014
322 parameters	Δρmax = 0.45 e Å^−3
132 restraints	Δρmin = −0.34 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	0.5000	0.5000	0.5000	0.0543 (4)
N1	0.5200 (5)	0.5606 (3)	0.2565 (3)	0.0516 (12)
N2	0.5601 (5)	0.5121 (3)	0.3820 (3)	0.0567 (13)
N3	0.6868 (5)	0.4993 (3)	0.3444 (3)	0.0578 (13)
N4	0.3086 (5)	0.5501 (3)	0.4364 (3)	0.0550 (13)
N5	0.8649 (6)	0.4648 (4)	0.2176 (4)	0.092 (2)
O1W	0.4285 (6)	0.3757 (3)	0.4747 (3)	0.0774 (16)
H1WA	0.371 (8)	0.368 (5)	0.438 (4)	0.080*
H1WB	0.416 (7)	0.347 (4)	0.515 (4)	0.080*
O2W	0.7656 (10)	0.8529 (5)	0.1554 (5)	0.166 (3)
H2WA	0.757 (8)	0.8004 (16)	0.161 (5)	0.080*
O3W	1.0669 (9)	0.8312 (7)	0.1631 (7)	0.214 (4)
H3WA	0.997 (7)	0.866 (4)	0.146 (4)	0.080*
C1	0.4620 (6)	0.5478 (4)	0.3301 (3)	0.0499 (15)
C2	0.6606 (7)	0.5290 (4)	0.2699 (4)	0.0552 (16)
C3	0.3157 (6)	0.5683 (4)	0.3560 (4)	0.0537 (16)
C4	0.1991 (7)	0.6010 (4)	0.3072 (4)	0.0661 (18)
H4	0.2071	0.6125	0.2516	0.079*
C5	0.0694 (7)	0.6167 (4)	0.3420 (4)	0.075 (2)
H5	−0.0107	0.6406	0.3106	0.090*
C6	0.0607 (7)	0.5966 (4)	0.4235 (5)	0.074 (2)
H6	−0.0266	0.6047	0.4478	0.089*
C7	0.1819 (7)	0.5644 (4)	0.4685 (4)	0.0669 (18)
H7	0.1757	0.5520	0.5241	0.080*
C8	0.7730 (7)	0.5311 (5)	0.2095 (4)	0.0652 (19)
C9	0.7831 (7)	0.5965 (5)	0.1545 (4)	0.084 (2)
H9	0.7154	0.6415	0.1512	0.101*
C10	0.8962 (9)	0.5946 (6)	0.1036 (4)	0.103 (3)
H10	0.9079	0.6385	0.0657	0.124*
C11	0.9897 (10)	0.5265 (7)	0.1110 (5)	0.108 (3)
H11	1.0655	0.5229	0.0765	0.129*
C12	0.9750 (9)	0.4641 (6)	0.1670 (6)	0.108 (3)
H12	1.0425	0.4190	0.1713	0.130*
C13	0.4516 (6)	0.5951 (4)	0.1806 (3)	0.0498 (15)
C14	0.4280 (7)	0.6819 (4)	0.1720 (4)	0.0659 (18)
H14	0.4527	0.7191	0.2160	0.079*
C15	0.3677 (7)	0.7135 (4)	0.0979 (5)	0.0756 (19)
H15	0.3504	0.7725	0.0924	0.091*
C16	0.3317 (7)	0.6601 (5)	0.0311 (4)	0.0657 (18)
C17	0.3563 (6)	0.5731 (5)	0.0415 (4)	0.0632 (18)
H17	0.3320	0.5357	−0.0024	0.076*
C18	0.4166 (6)	0.5403 (4)	0.1164 (4)	0.0549 (16)
H18	0.4329	0.4812	0.1227	0.066*
C19	0.2682 (8)	0.6959 (5)	−0.0509 (4)	0.104 (3)
H19A	0.2506	0.6495	−0.0898	0.156*
H19B	0.3361	0.7362	−0.0713	0.156*
H19C	0.1772	0.7248	−0.0438	0.156*
Cl1	0.2960 (2)	0.28184 (14)	0.12820 (13)	0.1028 (7)
O1A	0.4237 (11)	0.2330 (8)	0.1111 (7)	0.079 (4)*	0.360 (4)
O2A	0.331 (2)	0.3619 (9)	0.1691 (12)	0.221 (14)*	0.360 (4)
O3A	0.2304 (16)	0.2277 (10)	0.1899 (8)	0.128 (6)*	0.360 (4)
O4A	0.1854 (16)	0.2902 (13)	0.0610 (9)	0.192 (9)*	0.360 (4)
O1B	0.1408 (9)	0.2882 (10)	0.1342 (11)	0.181 (8)*	0.418 (9)
O2B	0.3766 (12)	0.3321 (7)	0.1935 (6)	0.080 (4)*	0.418 (9)
O3B	0.3287 (14)	0.3230 (8)	0.0514 (5)	0.114 (5)*	0.418 (9)
O4B	0.3434 (14)	0.1944 (5)	0.1313 (8)	0.107 (5)*	0.418 (9)
O1C	0.2480 (19)	0.3542 (9)	0.0785 (10)	0.066 (7)*	0.222 (9)
O2C	0.264 (3)	0.2031 (10)	0.0816 (13)	0.173 (14)*	0.222 (9)
O3C	0.4488 (12)	0.288 (2)	0.1557 (18)	0.26 (2)*	0.222 (9)
O4C	0.207 (2)	0.2768 (15)	0.1977 (10)	0.117 (11)*	0.222 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0517 (7)	0.0598 (7)	0.0533 (7)	0.0071 (6)	0.0152 (5)	0.0076 (6)
N1	0.054 (3)	0.057 (3)	0.045 (3)	0.004 (3)	0.011 (2)	0.002 (2)
N2	0.059 (3)	0.062 (4)	0.051 (3)	0.010 (3)	0.014 (3)	0.007 (3)
N3	0.047 (3)	0.072 (3)	0.057 (3)	0.007 (3)	0.019 (2)	0.002 (3)
N4	0.059 (3)	0.055 (3)	0.053 (3)	0.006 (3)	0.017 (3)	0.005 (3)
N5	0.061 (4)	0.137 (6)	0.083 (4)	0.012 (4)	0.030 (3)	−0.019 (4)
O1W	0.096 (4)	0.065 (3)	0.071 (4)	−0.003 (3)	0.007 (3)	0.003 (3)
O2W	0.191 (7)	0.168 (7)	0.131 (5)	−0.006 (7)	−0.025 (5)	0.045 (6)
O3W	0.150 (8)	0.236 (12)	0.266 (11)	−0.027 (6)	0.072 (8)	−0.070 (9)
C1	0.054 (4)	0.054 (4)	0.042 (4)	0.004 (3)	0.009 (3)	0.005 (3)
C2	0.054 (4)	0.066 (4)	0.046 (4)	0.003 (3)	0.010 (3)	0.002 (3)
C3	0.047 (4)	0.048 (4)	0.068 (4)	−0.002 (3)	0.012 (3)	−0.005 (3)
C4	0.054 (4)	0.087 (5)	0.057 (4)	0.008 (4)	0.004 (4)	0.007 (4)
C5	0.056 (5)	0.090 (6)	0.078 (5)	0.015 (4)	−0.004 (4)	−0.003 (4)
C6	0.051 (5)	0.083 (5)	0.091 (6)	0.007 (4)	0.018 (4)	0.004 (4)
C7	0.054 (4)	0.081 (5)	0.070 (4)	0.008 (4)	0.026 (4)	0.012 (4)
C8	0.052 (4)	0.099 (6)	0.046 (4)	0.000 (4)	0.013 (3)	−0.010 (4)
C9	0.061 (5)	0.137 (7)	0.056 (4)	−0.012 (4)	0.011 (4)	0.023 (5)
C10	0.095 (6)	0.149 (7)	0.065 (5)	−0.022 (5)	0.012 (4)	0.021 (5)
C11	0.086 (5)	0.168 (8)	0.073 (5)	−0.014 (6)	0.022 (4)	−0.025 (5)
C12	0.084 (5)	0.139 (7)	0.102 (6)	0.017 (5)	0.005 (5)	−0.026 (5)
C13	0.045 (4)	0.060 (5)	0.046 (4)	−0.006 (3)	0.011 (3)	0.003 (3)
C14	0.087 (5)	0.057 (5)	0.054 (4)	−0.011 (4)	0.003 (4)	−0.010 (3)
C15	0.083 (5)	0.049 (4)	0.092 (6)	−0.008 (4)	−0.009 (4)	0.009 (4)
C16	0.056 (4)	0.075 (5)	0.067 (5)	−0.004 (4)	0.007 (3)	0.014 (4)
C17	0.059 (4)	0.078 (5)	0.054 (4)	0.000 (4)	0.010 (3)	−0.009 (4)
C18	0.055 (4)	0.050 (4)	0.060 (4)	−0.004 (3)	0.010 (3)	−0.003 (3)
C19	0.110 (6)	0.127 (7)	0.071 (5)	0.008 (5)	−0.017 (4)	0.029 (5)
Cl1	0.1089 (17)	0.0890 (16)	0.1140 (17)	0.0216 (13)	0.0297 (14)	−0.0010 (13)

Geometric parameters (Å, º)

Ni1—N2^i	2.048 (4)	C9—H9	0.93
Ni1—N2	2.048 (4)	C10—C11	1.356 (11)
Ni1—O1W	2.062 (5)	C10—H10	0.93
Ni1—O1W^i	2.062 (5)	C11—C12	1.343 (11)
Ni1—N4	2.098 (5)	C11—H11	0.93
Ni1—N4^i	2.098 (5)	C12—H12	0.93
N1—C1	1.365 (6)	C13—C18	1.360 (7)
N1—C2	1.374 (7)	C13—C14	1.367 (8)
N1—C13	1.434 (7)	C14—C15	1.368 (8)
N2—C1	1.298 (7)	C14—H14	0.93
N2—N3	1.371 (5)	C15—C16	1.379 (8)
N3—C2	1.297 (7)	C15—H15	0.93
N4—C7	1.330 (6)	C16—C17	1.373 (8)
N4—C3	1.343 (7)	C16—C19	1.509 (8)
N5—C8	1.325 (8)	C17—C18	1.386 (8)
N5—C12	1.355 (9)	C17—H17	0.93
O1W—H1WA	0.77 (6)	C18—H18	0.93
O1W—H1WB	0.80 (6)	C19—H19A	0.96
O2W—H2WA	0.82 (2)	C19—H19B	0.96
O3W—H3WA	0.86 (2)	C19—H19C	0.96
C1—C3	1.472 (7)	Cl1—O4B	1.420 (7)
C2—C8	1.483 (8)	Cl1—O4A	1.425 (8)
C3—C4	1.367 (7)	Cl1—O1C	1.426 (8)
C4—C5	1.379 (8)	Cl1—O2A	1.428 (8)
C4—H4	0.93	Cl1—O3C	1.430 (9)
C5—C6	1.369 (8)	Cl1—O1B	1.434 (8)
C5—H5	0.93	Cl1—O1A	1.438 (7)
C6—C7	1.365 (8)	Cl1—O2C	1.450 (9)
C6—H6	0.93	Cl1—O4C	1.453 (8)
C7—H7	0.93	Cl1—O3B	1.456 (7)
C8—C9	1.359 (8)	Cl1—O2B	1.460 (7)
C9—C10	1.380 (9)	Cl1—O3A	1.475 (8)
N2^i—Ni1—N2	180.000 (1)	C8—C9—H9	120.8
N2^i—Ni1—O1W	89.69 (19)	C10—C9—H9	120.8
N2—Ni1—O1W	90.31 (19)	C11—C10—C9	117.7 (8)
N2^i—Ni1—O1W^i	90.31 (19)	C11—C10—H10	121.2
N2—Ni1—O1W^i	89.69 (19)	C9—C10—H10	121.2
O1W—Ni1—O1W^i	180.000 (1)	C12—C11—C10	121.2 (8)
N2^i—Ni1—N4	102.24 (19)	C12—C11—H11	119.4
N2—Ni1—N4	77.76 (19)	C10—C11—H11	119.4
O1W—Ni1—N4	90.65 (19)	C11—C12—N5	122.0 (8)
O1W^i—Ni1—N4	89.35 (19)	C11—C12—H12	119.0
N2^i—Ni1—N4^i	77.76 (19)	N5—C12—H12	119.0
N2—Ni1—N4^i	102.24 (19)	C18—C13—C14	120.8 (6)
O1W—Ni1—N4^i	89.35 (19)	C18—C13—N1	118.8 (6)
O1W^i—Ni1—N4^i	90.65 (19)	C14—C13—N1	120.4 (6)
N4—Ni1—N4^i	180.000 (1)	C13—C14—C15	119.2 (6)
C1—N1—C2	104.0 (5)	C13—C14—H14	120.4
C1—N1—C13	129.3 (5)	C15—C14—H14	120.4
C2—N1—C13	126.7 (4)	C14—C15—C16	121.8 (6)
C1—N2—N3	109.5 (5)	C14—C15—H15	119.1
C1—N2—Ni1	114.8 (4)	C16—C15—H15	119.1
N3—N2—Ni1	135.4 (4)	C17—C16—C15	117.8 (6)
C2—N3—N2	105.9 (5)	C17—C16—C19	120.9 (7)
C7—N4—C3	117.7 (5)	C15—C16—C19	121.3 (7)
C7—N4—Ni1	125.9 (4)	C16—C17—C18	121.1 (6)
C3—N4—Ni1	116.4 (4)	C16—C17—H17	119.5
C8—N5—C12	116.4 (7)	C18—C17—H17	119.5
Ni1—O1W—H1WA	118 (5)	C13—C18—C17	119.4 (6)
Ni1—O1W—H1WB	115 (5)	C13—C18—H18	120.3
H1WA—O1W—H1WB	114 (8)	C17—C18—H18	120.3
N2—C1—N1	109.3 (5)	C16—C19—H19A	109.5
N2—C1—C3	119.9 (5)	C16—C19—H19B	109.5
N1—C1—C3	130.8 (6)	H19A—C19—H19B	109.5
N3—C2—N1	111.4 (5)	C16—C19—H19C	109.5
N3—C2—C8	123.0 (6)	H19A—C19—H19C	109.5
N1—C2—C8	125.5 (6)	H19B—C19—H19C	109.5
N4—C3—C4	122.5 (5)	O4A—Cl1—O2A	112.9 (9)
N4—C3—C1	111.0 (5)	O1C—Cl1—O3C	111.5 (10)
C4—C3—C1	126.5 (6)	O4B—Cl1—O1B	111.3 (7)
C3—C4—C5	118.8 (6)	O4A—Cl1—O1A	115.6 (8)
C3—C4—H4	120.6	O2A—Cl1—O1A	113.4 (8)
C5—C4—H4	120.6	O1C—Cl1—O2C	109.1 (9)
C6—C5—C4	118.8 (6)	O3C—Cl1—O2C	111.3 (10)
C6—C5—H5	120.6	O1C—Cl1—O4C	108.4 (9)
C4—C5—H5	120.6	O3C—Cl1—O4C	111.2 (10)
C7—C6—C5	119.0 (6)	O2C—Cl1—O4C	105.0 (9)
C7—C6—H6	120.5	O4B—Cl1—O3B	111.2 (7)
C5—C6—H6	120.5	O1B—Cl1—O3B	108.0 (7)
N4—C7—C6	123.0 (6)	O4B—Cl1—O2B	110.5 (6)
N4—C7—H7	118.5	O1B—Cl1—O2B	110.6 (7)
C6—C7—H7	118.5	O3B—Cl1—O2B	105.1 (6)
N5—C8—C9	124.2 (6)	O4A—Cl1—O3A	105.5 (8)
N5—C8—C2	112.8 (6)	O2A—Cl1—O3A	105.3 (8)
C9—C8—C2	122.9 (7)	O1A—Cl1—O3A	102.7 (7)
C8—C9—C10	118.4 (7)
O1W—Ni1—N2—C1	94.9 (4)	N1—C1—C3—N4	−175.6 (5)
O1W^i—Ni1—N2—C1	−85.1 (4)	N2—C1—C3—C4	−175.8 (6)
N4—Ni1—N2—C1	4.3 (4)	N1—C1—C3—C4	4.9 (10)
N4^i—Ni1—N2—C1	−175.7 (4)	N4—C3—C4—C5	0.7 (9)
O1W—Ni1—N2—N3	−93.1 (5)	C1—C3—C4—C5	−179.8 (6)
O1W^i—Ni1—N2—N3	86.9 (5)	C3—C4—C5—C6	−1.9 (10)
N4—Ni1—N2—N3	176.3 (6)	C4—C5—C6—C7	2.2 (10)
N4^i—Ni1—N2—N3	−3.7 (6)	C3—N4—C7—C6	0.0 (9)
C1—N2—N3—C2	0.5 (6)	Ni1—N4—C7—C6	−179.4 (5)
Ni1—N2—N3—C2	−171.8 (4)	C5—C6—C7—N4	−1.3 (10)
N2^i—Ni1—N4—C7	−2.9 (5)	C12—N5—C8—C9	0.1 (10)
N2—Ni1—N4—C7	177.1 (5)	C12—N5—C8—C2	−177.2 (6)
O1W—Ni1—N4—C7	86.9 (5)	N3—C2—C8—N5	34.1 (9)
O1W^i—Ni1—N4—C7	−93.1 (5)	N1—C2—C8—N5	−148.9 (6)
N2^i—Ni1—N4—C3	177.6 (4)	N3—C2—C8—C9	−143.2 (7)
N2—Ni1—N4—C3	−2.4 (4)	N1—C2—C8—C9	33.9 (9)
O1W—Ni1—N4—C3	−92.5 (4)	N5—C8—C9—C10	−0.2 (10)
O1W^i—Ni1—N4—C3	87.5 (4)	C2—C8—C9—C10	176.8 (6)
N3—N2—C1—N1	−0.4 (6)	C8—C9—C10—C11	0.9 (11)
Ni1—N2—C1—N1	173.6 (3)	C9—C10—C11—C12	−1.5 (13)
N3—N2—C1—C3	−179.8 (5)	C10—C11—C12—N5	1.5 (13)
Ni1—N2—C1—C3	−5.8 (7)	C8—N5—C12—C11	−0.7 (11)
C2—N1—C1—N2	0.2 (6)	C1—N1—C13—C18	−106.5 (6)
C13—N1—C1—N2	177.5 (5)	C2—N1—C13—C18	70.3 (7)
C2—N1—C1—C3	179.5 (6)	C1—N1—C13—C14	76.3 (7)
C13—N1—C1—C3	−3.1 (10)	C2—N1—C13—C14	−106.9 (7)
N2—N3—C2—N1	−0.4 (6)	C18—C13—C14—C15	0.3 (9)
N2—N3—C2—C8	177.1 (5)	N1—C13—C14—C15	177.6 (5)
C1—N1—C2—N3	0.1 (6)	C13—C14—C15—C16	−0.9 (10)
C13—N1—C2—N3	−177.3 (5)	C14—C15—C16—C17	1.1 (10)
C1—N1—C2—C8	−177.2 (6)	C14—C15—C16—C19	−178.7 (6)
C13—N1—C2—C8	5.3 (9)	C15—C16—C17—C18	−0.7 (9)
C7—N4—C3—C4	0.3 (9)	C19—C16—C17—C18	179.1 (5)
Ni1—N4—C3—C4	179.8 (5)	C14—C13—C18—C17	0.0 (8)
C7—N4—C3—C1	−179.2 (5)	N1—C13—C18—C17	−177.2 (5)
Ni1—N4—C3—C1	0.2 (6)	C16—C17—C18—C13	0.2 (8)
N2—C1—C3—N4	3.7 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2W^ii	0.77 (6)	1.89 (6)	2.657 (9)	178 (8)
O1W—H1WB···O1A^iii	0.80 (6)	1.99 (6)	2.785 (12)	169 (7)
O1W—H1WB···O4B^iii	0.80 (6)	2.16 (6)	2.933 (13)	162 (7)
O1W—H1WB···O2C^iii	0.80 (6)	2.00 (6)	2.69 (2)	144 (6)
O3W—H3WA···O2W	0.86 (2)	2.15 (7)	2.766 (12)	129 (7)

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