mer-Bis(quinoline-2-carboxaldehyde 4-ethyl­thio­semicarbazonato)nickel(II) methanol 0.33-solvate 0.67-hydrate

In the title compound, [Ni(C₁₃H₁₃N₄S)₂]·0.33CH₃OH·0.67H₂O, the Ni^II atom is coordinated by two tridentate quinoline-2-carboxaldehyde 4-ethyl­thio­semi­car­ba­zonate ligands in a distorted octa­hedral shape. At 100 K, the crystal symmetry is monoclinic (space group P2₁/n). A mixture of water and methanol crystallizes with the title complex, and one of the ethyl groups in the coordinating ligands is disordered over two positions, with an occupancy ratio of 58:42. There is inter­molecular hydrogen bonding between the solvent mol­ecules and the amine and thiol­ate groups in the ligands. No other significant inter­actions are present in the crystal packing.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.036
• wR factor = 0.083
• Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Bond Without Acceptor  O1W      --H1W      .     Please Check

Author Response: Checked and there is no acceptor for H1W

Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
              Calc: C26.33 H28.66 N8 Ni O S2
              Rep.: C26.33 H28.65 N8 Ni O S2
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.8 Ratio
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        4.5 Ratio
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.570 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          8 Note
                1  1  0,   0  2  0,   1  2  0,  -1  0  1,   1  0  1,  -1  1  1,
                0  1  1,   0  2  1,
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
               -1  4  2,  -1  0  3,
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check
               -8  0  6,

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          4 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          3 Report
              H1S   H1W   H2W
PLAT068_ALERT_1_G Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT188_ALERT_3_G A Non-default SIMU Restraint Value has been used     0.0100 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ni1      --S1       .        9.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ni1      --S2       .        6.9 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ni1      --N2       .        5.6 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd    1)         5% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd    2)       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd    3)       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd    2)       1.97 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd    3)       2.02 Check
PLAT484_ALERT_4_G Round D-H..A Angle Rep for O1S      ..S2       .        154 Degree
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1       (II)      .       1.97 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          4 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         36 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          6 Note
                1  0  1,   1  1  0,  -1  0  1,  -1  4  2,  -1  1  1,   0  2  1,
PLAT965_ALERT_2_G The SHELXL WEIGHT Optimisation has not Converged     Please Check
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       2.89 Note
              Predicted wR2: Based on SigI   2  2.85 or SHELX Weight  7.82       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         17 Info

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

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

---

Computing details

mer-Bis(quinoline-2-carboxaldehyde 4-ethylthiosemicarbazonato)nickel(II) methanol 0.33-solvate 0.67-hydrate

Crystal data

[Ni(C13H13N4S)2]·0.328CH4O·0.672H2O	Dx = 1.489 Mg m^−3
Mr = 595.97	Melting point: 541 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.0560 (6) Å	Cell parameters from 9658 reflections
b = 21.3696 (9) Å	θ = 2.6–30.4°
c = 12.5648 (6) Å	µ = 0.93 mm^−1
β = 100.161 (2)°	T = 100 K
V = 2657.7 (2) Å^3	Rod, dark brown
Z = 4	0.13 × 0.13 × 0.10 mm
F(000) = 1242

Data collection

Bruker D8 Venture diffractometer	7523 reflections with I > 2σ(I)
Radiation source: Microfocus Sealed Tube	Rint = 0.076
φ and ω scans	θmax = 30.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −14→14
Tmin = 0.710, Tmax = 0.746	k = −30→30
143112 measured reflections	l = −17→17
8094 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: mixed
wR(F^2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0226P)^2 + 3.305P] where P = (Fo^2 + 2Fc^2)/3
8094 reflections	(Δ/σ)max = 0.002
385 parameters	Δρmax = 0.46 e Å^−3
36 restraints	Δρmin = −0.47 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.37125 (2)	0.34643 (2)	0.54815 (2)	0.01053 (5)
S1	0.58288 (4)	0.34892 (2)	0.48937 (3)	0.01341 (8)
S2	0.23953 (4)	0.30891 (2)	0.37971 (3)	0.01339 (8)
N1	0.21681 (13)	0.31495 (6)	0.63795 (11)	0.0125 (2)
N2	0.44276 (13)	0.26050 (6)	0.60052 (10)	0.0113 (2)
N3	0.55983 (13)	0.23412 (6)	0.58182 (11)	0.0126 (2)
N4	0.74864 (14)	0.25342 (7)	0.50791 (12)	0.0156 (3)
H4	0.791 (2)	0.2775 (11)	0.4735 (19)	0.024 (6)*
N5	0.44660 (13)	0.41468 (6)	0.67711 (10)	0.0119 (2)
N6	0.31246 (13)	0.42947 (6)	0.47570 (10)	0.0117 (2)
N7	0.24729 (13)	0.43707 (6)	0.37230 (11)	0.0130 (2)
N8	0.14719 (14)	0.38603 (7)	0.21967 (11)	0.0159 (3)
H8	0.125 (2)	0.3518 (11)	0.187 (2)	0.025 (6)*
C1	0.10008 (15)	0.34256 (7)	0.65722 (13)	0.0143 (3)
C2	0.07119 (17)	0.40507 (8)	0.62318 (15)	0.0202 (3)
H2	0.132819	0.427501	0.588242	0.024*
C3	−0.04576 (18)	0.43326 (9)	0.64064 (17)	0.0244 (4)
H3	−0.064523	0.475099	0.617169	0.029*
C4	−0.13860 (17)	0.40102 (9)	0.69295 (16)	0.0220 (3)
H4A	−0.219476	0.421041	0.703837	0.026*
C5	−0.11204 (16)	0.34105 (8)	0.72788 (14)	0.0188 (3)
H5	−0.174306	0.319666	0.763675	0.023*
C6	0.00747 (15)	0.31046 (8)	0.71120 (13)	0.0148 (3)
C7	0.03928 (16)	0.24885 (8)	0.74760 (13)	0.0161 (3)
H7	−0.020396	0.226208	0.784164	0.019*
C8	0.15664 (16)	0.22215 (7)	0.72970 (13)	0.0146 (3)
H8A	0.180217	0.181002	0.754807	0.018*
C9	0.24290 (15)	0.25634 (7)	0.67338 (12)	0.0124 (3)
C10	0.36676 (15)	0.22762 (7)	0.65212 (12)	0.0124 (3)
H10	0.390954	0.186202	0.675312	0.015*
C11	0.63063 (15)	0.27363 (7)	0.53007 (12)	0.0124 (3)
C12	0.80517 (16)	0.19107 (8)	0.53084 (14)	0.0172 (3)
H12A	0.786655	0.177009	0.601868	0.021*
H12B	0.904409	0.193044	0.535614	0.021*
C13	0.74744 (19)	0.14358 (8)	0.44520 (16)	0.0228 (3)
H13A	0.790999	0.102944	0.462710	0.034*
H13B	0.764093	0.157600	0.374460	0.034*
H13C	0.649940	0.139539	0.443148	0.034*
C14	0.51401 (15)	0.40752 (7)	0.78126 (12)	0.0123 (3)
C15	0.54723 (16)	0.34674 (7)	0.82233 (13)	0.0147 (3)
H15	0.524935	0.311347	0.776942	0.018*
C16	0.61140 (16)	0.33856 (8)	0.92725 (13)	0.0164 (3)
H16	0.632372	0.297488	0.953940	0.020*
C17	0.64651 (17)	0.39034 (8)	0.99577 (14)	0.0181 (3)
H17	0.689126	0.383985	1.068662	0.022*
C18	0.61934 (17)	0.44984 (8)	0.95752 (13)	0.0173 (3)
H18	0.645279	0.484621	1.003611	0.021*
C19	0.55302 (16)	0.45990 (7)	0.85004 (13)	0.0142 (3)
C20	0.52339 (17)	0.52050 (8)	0.80729 (13)	0.0171 (3)
H20	0.548570	0.556342	0.850925	0.020*
C21	0.45851 (17)	0.52724 (7)	0.70315 (13)	0.0163 (3)
H21	0.438725	0.567711	0.673239	0.020*
C22	0.42098 (15)	0.47294 (7)	0.64009 (12)	0.0128 (3)
C23	0.35131 (16)	0.47991 (7)	0.52932 (13)	0.0136 (3)
H23	0.334804	0.520070	0.497294	0.016*
C24	0.21181 (15)	0.38279 (7)	0.32265 (12)	0.0121 (3)
C25	0.1078 (15)	0.4456 (8)	0.1591 (14)	0.021 (2)	0.58 (2)
H25A	0.161021	0.480574	0.196717	0.025*	0.58 (2)
H25B	0.130426	0.442171	0.085764	0.025*	0.58 (2)
C26	−0.0373 (7)	0.4598 (3)	0.1497 (11)	0.0455 (18)	0.58 (2)
H26A	−0.055776	0.501394	0.117810	0.068*	0.58 (2)
H26B	−0.062309	0.458858	0.221588	0.068*	0.58 (2)
H26C	−0.090205	0.428441	0.103356	0.068*	0.58 (2)
C25A	0.1242 (19)	0.4421 (11)	0.1610 (18)	0.017 (2)	0.42 (2)
H25C	0.181819	0.443287	0.104807	0.021*	0.42 (2)
H25D	0.149015	0.478010	0.210232	0.021*	0.42 (2)
C26A	−0.0277 (10)	0.4477 (6)	0.1064 (12)	0.041 (2)	0.42 (2)
H26D	−0.043953	0.489086	0.073039	0.061*	0.42 (2)
H26E	−0.085129	0.442191	0.161080	0.061*	0.42 (2)
H26F	−0.049072	0.415319	0.050730	0.061*	0.42 (2)
O1W	0.9174 (12)	0.3352 (4)	0.3991 (10)	0.0262 (8)	0.672 (6)
H1W	0.926373	0.363814	0.449173	0.039*	0.672 (6)
H2W	0.999607	0.326761	0.391031	0.039*	0.672 (6)
O1S	0.924 (3)	0.3269 (10)	0.394 (2)	0.0262 (8)	0.328 (6)
H1S	1.007535	0.322428	0.413664	0.039*	0.328 (6)
C1S	0.8922 (6)	0.3926 (3)	0.3797 (5)	0.0262 (8)	0.328 (6)
H1A	0.828778	0.404763	0.426964	0.039*	0.328 (6)
H1B	0.851011	0.400377	0.304168	0.039*	0.328 (6)
H1C	0.975225	0.417242	0.398023	0.039*	0.328 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.00948 (9)	0.00951 (9)	0.01260 (9)	0.00096 (6)	0.00196 (7)	0.00092 (7)
S1	0.01215 (16)	0.01128 (16)	0.01730 (18)	0.00052 (12)	0.00392 (13)	0.00194 (13)
S2	0.01316 (16)	0.01044 (15)	0.01588 (17)	0.00003 (12)	0.00072 (13)	0.00007 (13)
N1	0.0099 (5)	0.0132 (6)	0.0148 (6)	0.0006 (4)	0.0033 (5)	0.0001 (5)
N2	0.0094 (5)	0.0121 (5)	0.0122 (6)	0.0006 (4)	0.0012 (4)	−0.0004 (4)
N3	0.0100 (5)	0.0128 (6)	0.0152 (6)	0.0021 (4)	0.0031 (5)	0.0008 (5)
N4	0.0120 (6)	0.0154 (6)	0.0202 (7)	0.0020 (5)	0.0054 (5)	0.0030 (5)
N5	0.0104 (5)	0.0125 (6)	0.0130 (6)	−0.0002 (4)	0.0025 (4)	0.0002 (4)
N6	0.0100 (5)	0.0131 (6)	0.0122 (6)	0.0018 (4)	0.0022 (4)	0.0007 (4)
N7	0.0137 (6)	0.0126 (6)	0.0122 (6)	0.0010 (4)	0.0004 (5)	0.0006 (5)
N8	0.0180 (6)	0.0141 (6)	0.0142 (6)	−0.0001 (5)	−0.0012 (5)	−0.0008 (5)
C1	0.0117 (6)	0.0154 (7)	0.0155 (7)	0.0011 (5)	0.0018 (5)	−0.0005 (5)
C2	0.0163 (7)	0.0166 (7)	0.0297 (9)	0.0037 (6)	0.0094 (7)	0.0032 (6)
C3	0.0182 (8)	0.0192 (8)	0.0377 (10)	0.0053 (6)	0.0104 (7)	0.0014 (7)
C4	0.0127 (7)	0.0245 (8)	0.0298 (9)	0.0040 (6)	0.0067 (6)	−0.0035 (7)
C5	0.0114 (7)	0.0242 (8)	0.0219 (8)	−0.0004 (6)	0.0062 (6)	−0.0036 (6)
C6	0.0103 (6)	0.0195 (7)	0.0148 (7)	−0.0008 (5)	0.0025 (5)	−0.0015 (6)
C7	0.0140 (7)	0.0202 (7)	0.0147 (7)	−0.0026 (6)	0.0040 (5)	0.0010 (6)
C8	0.0138 (7)	0.0152 (7)	0.0148 (7)	−0.0019 (5)	0.0026 (5)	0.0023 (5)
C9	0.0127 (6)	0.0131 (6)	0.0113 (6)	−0.0006 (5)	0.0017 (5)	0.0000 (5)
C10	0.0122 (6)	0.0107 (6)	0.0144 (7)	0.0005 (5)	0.0024 (5)	0.0010 (5)
C11	0.0112 (6)	0.0133 (6)	0.0124 (6)	0.0006 (5)	0.0015 (5)	0.0000 (5)
C12	0.0131 (7)	0.0189 (7)	0.0198 (8)	0.0066 (6)	0.0037 (6)	0.0035 (6)
C13	0.0232 (8)	0.0183 (8)	0.0269 (9)	0.0053 (6)	0.0041 (7)	0.0009 (7)
C14	0.0098 (6)	0.0141 (6)	0.0133 (7)	−0.0001 (5)	0.0024 (5)	0.0002 (5)
C15	0.0155 (7)	0.0136 (7)	0.0146 (7)	0.0011 (5)	0.0017 (5)	−0.0003 (5)
C16	0.0159 (7)	0.0159 (7)	0.0168 (7)	0.0021 (5)	0.0015 (6)	0.0020 (6)
C17	0.0171 (7)	0.0202 (7)	0.0155 (7)	0.0005 (6)	−0.0012 (6)	0.0001 (6)
C18	0.0183 (7)	0.0170 (7)	0.0153 (7)	−0.0018 (6)	−0.0009 (6)	−0.0024 (6)
C19	0.0137 (7)	0.0143 (7)	0.0145 (7)	−0.0012 (5)	0.0020 (5)	−0.0006 (5)
C20	0.0209 (8)	0.0134 (7)	0.0160 (7)	−0.0019 (6)	0.0009 (6)	−0.0020 (6)
C21	0.0201 (7)	0.0117 (6)	0.0170 (7)	−0.0008 (5)	0.0030 (6)	−0.0004 (5)
C22	0.0119 (6)	0.0124 (6)	0.0140 (7)	−0.0002 (5)	0.0026 (5)	0.0000 (5)
C23	0.0144 (7)	0.0115 (6)	0.0146 (7)	0.0010 (5)	0.0021 (5)	0.0019 (5)
C24	0.0093 (6)	0.0132 (6)	0.0138 (7)	0.0006 (5)	0.0022 (5)	0.0006 (5)
C25	0.030 (5)	0.014 (2)	0.017 (2)	0.004 (3)	−0.002 (3)	0.0074 (18)
C26	0.028 (2)	0.031 (2)	0.068 (4)	0.0062 (17)	−0.017 (3)	0.003 (3)
C25A	0.010 (3)	0.022 (4)	0.016 (3)	0.001 (3)	−0.006 (2)	−0.003 (3)
C26A	0.030 (3)	0.037 (4)	0.049 (5)	0.002 (3)	−0.011 (3)	0.020 (3)
O1W	0.0180 (11)	0.033 (2)	0.0285 (12)	−0.0032 (15)	0.0077 (8)	−0.0046 (16)
O1S	0.0180 (11)	0.033 (2)	0.0285 (12)	−0.0032 (15)	0.0077 (8)	−0.0046 (16)
C1S	0.0180 (11)	0.033 (2)	0.0285 (12)	−0.0032 (15)	0.0077 (8)	−0.0046 (16)

Geometric parameters (Å, º)

Ni1—N6	2.0339 (13)	C12—C13	1.518 (2)
Ni1—N2	2.0384 (13)	C12—H12A	0.9900
Ni1—N1	2.1808 (13)	C12—H12B	0.9900
Ni1—N5	2.2120 (13)	C13—H13A	0.9800
Ni1—S1	2.3731 (4)	C13—H13B	0.9800
Ni1—S2	2.4264 (4)	C13—H13C	0.9800
S1—C11	1.7303 (15)	C14—C15	1.416 (2)
S2—C24	1.7359 (15)	C14—C19	1.426 (2)
N1—C9	1.3395 (19)	C15—C16	1.373 (2)
N1—C1	1.3730 (19)	C15—H15	0.9500
N2—C10	1.2935 (19)	C16—C17	1.408 (2)
N2—N3	1.3625 (17)	C16—H16	0.9500
N3—C11	1.3438 (19)	C17—C18	1.370 (2)
N4—C11	1.3376 (19)	C17—H17	0.9500
N4—C12	1.457 (2)	C18—C19	1.413 (2)
N4—H4	0.84 (2)	C18—H18	0.9500
N5—C22	1.3381 (19)	C19—C20	1.413 (2)
N5—C14	1.3720 (19)	C20—C21	1.363 (2)
N6—C23	1.294 (2)	C20—H20	0.9500
N6—N7	1.3578 (18)	C21—C22	1.418 (2)
N7—C24	1.3355 (19)	C21—H21	0.9500
N8—C24	1.343 (2)	C22—C23	1.451 (2)
N8—C25A	1.40 (2)	C23—H23	0.9500
N8—C25	1.499 (15)	C25—C26	1.474 (15)
N8—H8	0.85 (2)	C25—H25A	0.9900
C1—C2	1.417 (2)	C25—H25B	0.9900
C1—C6	1.422 (2)	C26—H26A	0.9800
C2—C3	1.373 (2)	C26—H26B	0.9800
C2—H2	0.9500	C26—H26C	0.9800
C3—C4	1.412 (3)	C25A—C26A	1.56 (2)
C3—H3	0.9500	C25A—H25C	0.9900
C4—C5	1.366 (3)	C25A—H25D	0.9900
C4—H4A	0.9500	C26A—H26D	0.9800
C5—C6	1.416 (2)	C26A—H26E	0.9800
C5—H5	0.9500	C26A—H26F	0.9800
C6—C7	1.412 (2)	O1W—H1W	0.8700
C7—C8	1.365 (2)	O1W—H2W	0.8700
C7—H7	0.9500	O1S—C1S	1.44 (2)
C8—C9	1.416 (2)	O1S—H1S	0.8400
C8—H8A	0.9500	C1S—H1A	0.9800
C9—C10	1.455 (2)	C1S—H1B	0.9800
C10—H10	0.9500	C1S—H1C	0.9800
N6—Ni1—N2	171.31 (5)	N4—C12—H12B	109.1
N6—Ni1—N1	108.87 (5)	C13—C12—H12B	109.1
N2—Ni1—N1	78.34 (5)	H12A—C12—H12B	107.8
N6—Ni1—N5	77.74 (5)	C12—C13—H13A	109.5
N2—Ni1—N5	107.56 (5)	C12—C13—H13B	109.5
N1—Ni1—N5	90.43 (5)	H13A—C13—H13B	109.5
N6—Ni1—S1	92.69 (4)	C12—C13—H13C	109.5
N2—Ni1—S1	80.56 (4)	H13A—C13—H13C	109.5
N1—Ni1—S1	158.05 (4)	H13B—C13—H13C	109.5
N5—Ni1—S1	90.18 (4)	N5—C14—C15	119.67 (14)
N6—Ni1—S2	80.04 (4)	N5—C14—C19	121.82 (14)
N2—Ni1—S2	95.23 (4)	C15—C14—C19	118.50 (14)
N1—Ni1—S2	91.16 (4)	C16—C15—C14	120.50 (15)
N5—Ni1—S2	157.00 (4)	C16—C15—H15	119.7
S1—Ni1—S2	96.747 (15)	C14—C15—H15	119.7
C11—S1—Ni1	96.00 (5)	C15—C16—C17	120.78 (15)
C24—S2—Ni1	94.75 (5)	C15—C16—H16	119.6
C9—N1—C1	117.82 (13)	C17—C16—H16	119.6
C9—N1—Ni1	110.17 (10)	C18—C17—C16	120.13 (15)
C1—N1—Ni1	131.89 (11)	C18—C17—H17	119.9
C10—N2—N3	117.81 (13)	C16—C17—H17	119.9
C10—N2—Ni1	116.44 (10)	C17—C18—C19	120.52 (15)
N3—N2—Ni1	125.69 (10)	C17—C18—H18	119.7
C11—N3—N2	111.78 (12)	C19—C18—H18	119.7
C11—N4—C12	125.70 (14)	C18—C19—C20	122.34 (15)
C11—N4—H4	117.6 (16)	C18—C19—C14	119.52 (14)
C12—N4—H4	116.6 (16)	C20—C19—C14	118.15 (14)
C22—N5—C14	117.88 (13)	C21—C20—C19	119.66 (15)
C22—N5—Ni1	109.80 (10)	C21—C20—H20	120.2
C14—N5—Ni1	132.30 (10)	C19—C20—H20	120.2
C23—N6—N7	116.66 (13)	C20—C21—C22	119.02 (15)
C23—N6—Ni1	117.15 (10)	C20—C21—H21	120.5
N7—N6—Ni1	125.86 (10)	C22—C21—H21	120.5
C24—N7—N6	112.77 (12)	N5—C22—C21	123.45 (14)
C24—N8—C25A	123.8 (9)	N5—C22—C23	117.36 (13)
C24—N8—C25	124.9 (7)	C21—C22—C23	119.19 (14)
C24—N8—H8	117.5 (16)	N6—C23—C22	117.65 (14)
C25A—N8—H8	118.5 (19)	N6—C23—H23	121.2
C25—N8—H8	117.6 (17)	C22—C23—H23	121.2
N1—C1—C2	119.21 (14)	N7—C24—N8	116.68 (14)
N1—C1—C6	121.95 (14)	N7—C24—S2	125.94 (12)
C2—C1—C6	118.83 (14)	N8—C24—S2	117.37 (12)
C3—C2—C1	120.07 (16)	C26—C25—N8	112.6 (10)
C3—C2—H2	120.0	C26—C25—H25A	109.1
C1—C2—H2	120.0	N8—C25—H25A	109.1
C2—C3—C4	121.03 (17)	C26—C25—H25B	109.1
C2—C3—H3	119.5	N8—C25—H25B	109.1
C4—C3—H3	119.5	H25A—C25—H25B	107.8
C5—C4—C3	119.96 (16)	C25—C26—H26A	109.5
C5—C4—H4A	120.0	C25—C26—H26B	109.5
C3—C4—H4A	120.0	H26A—C26—H26B	109.5
C4—C5—C6	120.58 (16)	C25—C26—H26C	109.5
C4—C5—H5	119.7	H26A—C26—H26C	109.5
C6—C5—H5	119.7	H26B—C26—H26C	109.5
C7—C6—C5	122.16 (15)	N8—C25A—C26A	110.7 (14)
C7—C6—C1	118.33 (14)	N8—C25A—H25C	109.5
C5—C6—C1	119.50 (15)	C26A—C25A—H25C	109.5
C8—C7—C6	119.31 (15)	N8—C25A—H25D	109.5
C8—C7—H7	120.3	C26A—C25A—H25D	109.5
C6—C7—H7	120.3	H25C—C25A—H25D	108.1
C7—C8—C9	119.38 (15)	C25A—C26A—H26D	109.5
C7—C8—H8A	120.3	C25A—C26A—H26E	109.5
C9—C8—H8A	120.3	H26D—C26A—H26E	109.5
N1—C9—C8	123.19 (14)	C25A—C26A—H26F	109.5
N1—C9—C10	117.21 (13)	H26D—C26A—H26F	109.5
C8—C9—C10	119.61 (14)	H26E—C26A—H26F	109.5
N2—C10—C9	117.62 (13)	H1W—O1W—H2W	104.5
N2—C10—H10	121.2	C1S—O1S—H1S	109.5
C9—C10—H10	121.2	O1S—C1S—H1A	109.5
N4—C11—N3	117.59 (14)	O1S—C1S—H1B	109.5
N4—C11—S1	116.67 (12)	H1A—C1S—H1B	109.5
N3—C11—S1	125.74 (12)	O1S—C1S—H1C	109.5
N4—C12—C13	112.58 (14)	H1A—C1S—H1C	109.5
N4—C12—H12A	109.1	H1B—C1S—H1C	109.5
C13—C12—H12A	109.1
C10—N2—N3—C11	−178.48 (14)	C22—N5—C14—C15	−177.83 (14)
Ni1—N2—N3—C11	4.53 (18)	Ni1—N5—C14—C15	0.2 (2)
C23—N6—N7—C24	179.47 (13)	C22—N5—C14—C19	1.7 (2)
Ni1—N6—N7—C24	6.23 (18)	Ni1—N5—C14—C19	179.77 (11)
C9—N1—C1—C2	178.43 (15)	N5—C14—C15—C16	−178.22 (15)
Ni1—N1—C1—C2	−6.1 (2)	C19—C14—C15—C16	2.2 (2)
C9—N1—C1—C6	−1.1 (2)	C14—C15—C16—C17	−0.6 (2)
Ni1—N1—C1—C6	174.43 (11)	C15—C16—C17—C18	−1.4 (3)
N1—C1—C2—C3	179.27 (17)	C16—C17—C18—C19	1.6 (3)
C6—C1—C2—C3	−1.2 (3)	C17—C18—C19—C20	−179.83 (16)
C1—C2—C3—C4	0.4 (3)	C17—C18—C19—C14	0.1 (2)
C2—C3—C4—C5	0.6 (3)	N5—C14—C19—C18	178.44 (14)
C3—C4—C5—C6	−0.6 (3)	C15—C14—C19—C18	−2.0 (2)
C4—C5—C6—C7	179.03 (16)	N5—C14—C19—C20	−1.6 (2)
C4—C5—C6—C1	−0.2 (3)	C15—C14—C19—C20	177.97 (15)
N1—C1—C6—C7	1.3 (2)	C18—C19—C20—C21	−179.63 (16)
C2—C1—C6—C7	−178.14 (15)	C14—C19—C20—C21	0.4 (2)
N1—C1—C6—C5	−179.35 (15)	C19—C20—C21—C22	0.6 (2)
C2—C1—C6—C5	1.2 (2)	C14—N5—C22—C21	−0.7 (2)
C5—C6—C7—C8	−179.50 (16)	Ni1—N5—C22—C21	−179.18 (12)
C1—C6—C7—C8	−0.2 (2)	C14—N5—C22—C23	179.15 (13)
C6—C7—C8—C9	−1.1 (2)	Ni1—N5—C22—C23	0.68 (17)
C1—N1—C9—C8	−0.3 (2)	C20—C21—C22—N5	−0.4 (2)
Ni1—N1—C9—C8	−176.77 (12)	C20—C21—C22—C23	179.71 (15)
C1—N1—C9—C10	179.83 (13)	N7—N6—C23—C22	179.89 (13)
Ni1—N1—C9—C10	3.41 (16)	Ni1—N6—C23—C22	−6.25 (18)
C7—C8—C9—N1	1.4 (2)	N5—C22—C23—N6	3.5 (2)
C7—C8—C9—C10	−178.73 (14)	C21—C22—C23—N6	−176.61 (14)
N3—N2—C10—C9	179.06 (13)	N6—N7—C24—N8	−179.73 (13)
Ni1—N2—C10—C9	−3.66 (18)	N6—N7—C24—S2	1.23 (19)
N1—C9—C10—N2	−0.1 (2)	C25A—N8—C24—N7	4.5 (11)
C8—C9—C10—N2	−179.93 (14)	C25—N8—C24—N7	−2.6 (8)
C12—N4—C11—N3	2.8 (2)	C25A—N8—C24—S2	−176.4 (11)
C12—N4—C11—S1	−177.32 (13)	C25—N8—C24—S2	176.5 (8)
N2—N3—C11—N4	179.34 (13)	Ni1—S2—C24—N7	−5.77 (14)
N2—N3—C11—S1	−0.52 (19)	Ni1—S2—C24—N8	175.20 (12)
Ni1—S1—C11—N4	177.62 (12)	C24—N8—C25—C26	−103.1 (11)
Ni1—S1—C11—N3	−2.52 (14)	C24—N8—C25A—C26A	−129.9 (12)
C11—N4—C12—C13	82.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1W	0.84 (2)	2.10 (3)	2.936 (12)	174 (2)
N4—H4···O1S	0.84 (2)	2.08 (4)	2.91 (3)	170 (2)
O1S—H1S···S2^i	0.84	2.46	3.24 (2)	154
N8—H8···N3^ii	0.85 (2)	2.29 (2)	3.1349 (19)	174 (2)

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