Dinuclear cobalt and nickel com­plexes of a mercapto­acetic acid substituted 1,2,4-triazole ligand: syntheses, structures and urease inhibitory studies

Because of its versatile coordination modes and strong coordination ability, the mercapto­acetic acid substituted 1,2,4-triazole 2-{[5-(pyridin-2-yl)-4H-1,2,4-tri­azol-3-yl]sulfan­yl}acetic acid (H₂L) was synthesized and characterized. Treatment of H₂L with cobalt and nickel acetate afforded the dinuclear com­plexes {μ-3-[(carboxyl­atometh­yl)sulfan­yl]-5-(pyridin-2-yl)-4H-1,2,4-triazol-4-ido-κ²N¹,N⁵:N²,O}bis­[aqua­(methanol-κO)cobalt(II)] methanol disolvate, [Co₂(C₉H₆N₄O₂S)₂(CH₃OH)₂(H₂O)₂]·2CH₃OH (1), and {μ-3-[(carboxyl­ato­meth­yl)sulfan­yl]-5-(pyri­din-2-yl)-4H-1,2,4-triazol-4-ido-κ²N¹,N⁵:N²,O}bis­[di­aqua­nickel(II)] methanol disolvate dihydrate, [Ni₂(C₉H₆N₄O₂S)₂(H₂O)₄]·2CH₃OH·2H₂O (2), respectively. Complex 1 crystallized in the monoclinic space group P2₁/c, while 2 crystallized in the tetra­gonal space group I4₁/a. Single-crystal X-ray diffraction studies revealed that H₂L is doubly deprotonated and acts as a tetra­dentate bridging ligand in com­plexes 1 and 2. For both of the obtained com­plexes, extensive hydrogen-bond inter­actions contribute to the formation of their three-dimensional supermolecular structures. Hirshfeld surface analysis was used to illustrate the inter­molecular inter­actions. Additionally, the urease inhibitory activities of 1, 2 and H₂L were investigated against jack bean urease, where the two com­plexes revealed strong urease inhibition activities.

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015). Program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007) for (1); SHELXS97 (Sheldrick, 2008) for (2). For both structures, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

{µ-3-[(Carboxylatomethyl)sulfanyl]-5-(pyridin-2-yl)-4H-1,2,4-triazol-4-ido-κ²N¹,N⁵:N²,O}bis[aqua(methanol-κO)cobalt(II)] methanol disolvate (1)

Crystal data

[Co2(C9H6N4O2S)2(CH4O)2(H2O)2]·2CH4O	F(000) = 772
Mr = 375.27	Dx = 1.681 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5941 (5) Å	Cell parameters from 3192 reflections
b = 14.9735 (5) Å	θ = 3.5–27.9°
c = 10.7212 (5) Å	µ = 1.33 mm^−1
β = 105.719 (5)°	T = 293 K
V = 1482.58 (11) Å^3	Block, clear light red
Z = 4	0.13 × 0.1 × 0.06 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Eos detector	2813 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2198 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.040
Detector resolution: 16.0793 pixels mm^-1	θmax = 25.7°, θmin = 3.4°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −18→18
Tmin = 0.697, Tmax = 1.000	l = −13→13
9634 measured reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0452P)^2 + 0.6443P] where P = (Fo^2 + 2Fc^2)/3
2813 reflections	(Δ/σ)max = 0.002
205 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.38 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. 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 > 2sigma(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
O5	0.0600 (3)	0.74701 (16)	0.0046 (3)	0.0537 (7)
H5	−0.0110	0.7161	0.0029	0.081*
Co1	0.43485 (5)	0.58198 (2)	0.12944 (4)	0.03065 (15)
C1	0.1824 (4)	0.6061 (2)	0.2688 (3)	0.0424 (8)
H1	0.2315	0.6572	0.3057	0.051*
C2	0.0517 (4)	0.5871 (2)	0.2921 (3)	0.0498 (9)
H2	0.0128	0.6253	0.3422	0.060*
C3	−0.0206 (4)	0.5109 (2)	0.2404 (4)	0.0507 (9)
H3	−0.1093	0.4968	0.2549	0.061*
C4	0.0402 (4)	0.4552 (2)	0.1663 (3)	0.0411 (8)
H4	−0.0056	0.4025	0.1318	0.049*
C5	0.1700 (3)	0.47971 (18)	0.1449 (3)	0.0313 (7)
C6	0.2399 (3)	0.42889 (18)	0.0612 (3)	0.0296 (7)
C7	0.2879 (3)	0.33642 (19)	−0.0663 (3)	0.0337 (7)
C8	0.4398 (4)	0.1962 (2)	−0.1377 (4)	0.0473 (9)
H8A	0.4916	0.2105	−0.0490	0.057*
H8B	0.4290	0.1318	−0.1435	0.057*
C9	0.5307 (4)	0.22571 (19)	−0.2260 (3)	0.0353 (7)
C10	0.6575 (5)	0.5355 (3)	0.4020 (4)	0.0698 (12)
H10A	0.7565	0.5221	0.4060	0.105*
H10B	0.6311	0.5057	0.4714	0.105*
H10C	0.6466	0.5988	0.4099	0.105*
C11	0.0690 (5)	0.8148 (3)	0.0918 (5)	0.0807 (14)
H11A	0.1567	0.8479	0.0994	0.121*
H11B	0.0696	0.7904	0.1747	0.121*
H11C	−0.0127	0.8538	0.0625	0.121*
H3A	0.589 (6)	0.453 (4)	0.271 (5)	0.121*
N1	0.2425 (3)	0.55455 (16)	0.1956 (2)	0.0340 (6)
N2	0.3592 (3)	0.45912 (15)	0.0357 (2)	0.0307 (6)
N3	0.3906 (3)	0.39900 (15)	−0.0502 (2)	0.0316 (6)
N4	0.1911 (3)	0.35183 (16)	0.0016 (2)	0.0359 (6)
O1	0.5363 (3)	0.30680 (13)	−0.2522 (2)	0.0415 (6)
O2	0.5970 (3)	0.16538 (13)	−0.2667 (2)	0.0474 (6)
O3	0.5676 (3)	0.50635 (15)	0.2832 (2)	0.0520 (7)
O4	0.3017 (3)	0.65918 (15)	−0.0206 (2)	0.0486 (6)
H4A	0.2302	0.6927	−0.0197	0.073*
H4B	0.3305	0.6545	−0.0886	0.073*
S1	0.26298 (10)	0.24579 (6)	−0.17317 (10)	0.0563 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O5	0.0494 (17)	0.0439 (14)	0.0777 (18)	−0.0033 (11)	0.0340 (15)	−0.0048 (13)
Co1	0.0413 (3)	0.0196 (2)	0.0368 (3)	−0.00182 (17)	0.0205 (2)	−0.00387 (16)
C1	0.059 (2)	0.0312 (16)	0.045 (2)	−0.0015 (15)	0.0283 (18)	−0.0091 (14)
C2	0.063 (3)	0.045 (2)	0.051 (2)	0.0070 (18)	0.033 (2)	−0.0092 (16)
C3	0.051 (2)	0.054 (2)	0.057 (2)	0.0008 (18)	0.0332 (19)	−0.0041 (18)
C4	0.044 (2)	0.0358 (17)	0.0499 (19)	−0.0040 (15)	0.0236 (17)	−0.0062 (15)
C5	0.0378 (19)	0.0261 (15)	0.0346 (16)	0.0011 (13)	0.0174 (14)	0.0009 (12)
C6	0.0322 (18)	0.0246 (14)	0.0353 (16)	−0.0001 (12)	0.0149 (14)	−0.0009 (12)
C7	0.0339 (18)	0.0262 (15)	0.0460 (18)	−0.0019 (13)	0.0195 (15)	−0.0080 (13)
C8	0.073 (3)	0.0228 (15)	0.062 (2)	−0.0019 (15)	0.045 (2)	−0.0035 (15)
C9	0.052 (2)	0.0238 (15)	0.0368 (17)	−0.0052 (13)	0.0228 (15)	−0.0057 (13)
C10	0.083 (3)	0.059 (3)	0.061 (3)	0.018 (2)	0.009 (2)	−0.012 (2)
C11	0.071 (3)	0.076 (3)	0.094 (4)	−0.019 (3)	0.022 (3)	−0.006 (3)
N1	0.0466 (17)	0.0252 (12)	0.0359 (14)	0.0016 (11)	0.0209 (13)	−0.0013 (11)
N2	0.0373 (16)	0.0227 (12)	0.0366 (14)	0.0004 (11)	0.0177 (12)	−0.0051 (10)
N3	0.0369 (16)	0.0232 (12)	0.0390 (14)	−0.0017 (10)	0.0178 (12)	−0.0088 (10)
N4	0.0412 (17)	0.0273 (13)	0.0454 (16)	−0.0024 (11)	0.0225 (13)	−0.0053 (11)
O1	0.0694 (16)	0.0201 (10)	0.0449 (13)	−0.0054 (10)	0.0324 (12)	−0.0042 (9)
O2	0.0729 (18)	0.0242 (11)	0.0614 (15)	0.0004 (10)	0.0460 (14)	−0.0041 (10)
O3	0.0767 (19)	0.0247 (11)	0.0475 (15)	0.0024 (12)	0.0046 (13)	−0.0006 (10)
O4	0.0547 (16)	0.0550 (15)	0.0461 (14)	0.0216 (12)	0.0308 (12)	0.0130 (11)
S1	0.0523 (6)	0.0462 (5)	0.0800 (7)	−0.0165 (4)	0.0345 (6)	−0.0363 (5)

Geometric parameters (Å, º)

O5—H5	0.8200	C7—N4	1.346 (4)
O5—C11	1.367 (5)	C7—S1	1.750 (3)
Co1—N1	2.187 (3)	C8—H8A	0.9700
Co1—N2	2.127 (2)	C8—H8B	0.9700
Co1—N3^i	2.093 (2)	C8—C9	1.517 (4)
Co1—O1^i	2.094 (2)	C8—S1	1.796 (4)
Co1—O3	2.118 (2)	C9—O1	1.251 (3)
Co1—O4	2.108 (2)	C9—O2	1.249 (3)
C1—H1	0.9300	C10—H10A	0.9600
C1—C2	1.373 (5)	C10—H10B	0.9600
C1—N1	1.338 (4)	C10—H10C	0.9600
C2—H2	0.9300	C10—O3	1.400 (4)
C2—C3	1.372 (5)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C3—C4	1.385 (4)	C11—H11C	0.9600
C4—H4	0.9300	N2—N3	1.379 (3)
C4—C5	1.375 (4)	N3—Co1^i	2.093 (2)
C5—C6	1.470 (4)	O1—Co1^i	2.094 (2)
C5—N1	1.353 (4)	O3—H3A	0.84 (6)
C6—N2	1.326 (4)	O4—H4A	0.8522
C6—N4	1.340 (4)	O4—H4B	0.8499
C7—N3	1.336 (4)
C11—O5—H5	109.5	C9—C8—H8A	108.6
N2—Co1—N1	77.33 (9)	C9—C8—H8B	108.6
N3^i—Co1—N1	174.48 (9)	C9—C8—S1	114.6 (2)
N3^i—Co1—N2	97.73 (9)	S1—C8—H8A	108.6
N3^i—Co1—O1^i	99.37 (9)	S1—C8—H8B	108.6
N3^i—Co1—O3	90.55 (11)	O1—C9—C8	119.4 (3)
N3^i—Co1—O4	90.11 (9)	O2—C9—C8	116.1 (3)
O1^i—Co1—N1	85.71 (9)	O2—C9—O1	124.5 (3)
O1^i—Co1—N2	162.68 (9)	H10A—C10—H10B	109.5
O1^i—Co1—O3	89.24 (9)	H10A—C10—H10C	109.5
O1^i—Co1—O4	89.61 (9)	H10B—C10—H10C	109.5
O3—Co1—N1	91.71 (10)	O3—C10—H10A	109.5
O3—Co1—N2	87.80 (9)	O3—C10—H10B	109.5
O4—Co1—N1	87.72 (9)	O3—C10—H10C	109.5
O4—Co1—N2	93.16 (9)	O5—C11—H11A	109.5
O4—Co1—O3	178.75 (9)	O5—C11—H11B	109.5
C2—C1—H1	118.4	O5—C11—H11C	109.5
N1—C1—H1	118.4	H11A—C11—H11B	109.5
N1—C1—C2	123.2 (3)	H11A—C11—H11C	109.5
C1—C2—H2	120.5	H11B—C11—H11C	109.5
C3—C2—C1	119.1 (3)	C1—N1—Co1	128.2 (2)
C3—C2—H2	120.5	C1—N1—C5	117.1 (3)
C2—C3—H3	120.4	C5—N1—Co1	114.39 (19)
C2—C3—C4	119.1 (3)	C6—N2—Co1	113.67 (18)
C4—C3—H3	120.4	C6—N2—N3	105.8 (2)
C3—C4—H4	120.8	N3—N2—Co1	140.52 (19)
C5—C4—C3	118.4 (3)	C7—N3—Co1^i	133.35 (19)
C5—C4—H4	120.8	C7—N3—N2	104.9 (2)
C4—C5—C6	123.2 (3)	N2—N3—Co1^i	121.75 (18)
N1—C5—C4	123.0 (3)	C6—N4—C7	101.7 (2)
N1—C5—C6	113.8 (3)	C9—O1—Co1^i	129.6 (2)
N2—C6—C5	120.7 (2)	Co1—O3—H3A	120 (4)
N2—C6—N4	113.9 (2)	C10—O3—Co1	129.3 (2)
N4—C6—C5	125.4 (3)	C10—O3—H3A	109 (4)
N3—C7—N4	113.8 (3)	Co1—O4—H4A	129.6
N3—C7—S1	126.4 (2)	Co1—O4—H4B	109.8
N4—C7—S1	119.7 (2)	H4A—O4—H4B	120.6
H8A—C8—H8B	107.6	C7—S1—C8	103.21 (16)
Co1—N2—N3—Co1^i	0.4 (4)	N3^i—Co1—N1—C5	24.6 (11)
Co1—N2—N3—C7	−178.2 (2)	N3^i—Co1—N2—C6	−177.0 (2)
C1—C2—C3—C4	0.1 (6)	N3^i—Co1—N2—N3	−0.3 (3)
C2—C1—N1—Co1	172.1 (3)	N3^i—Co1—O3—C10	86.8 (3)
C2—C1—N1—C5	−1.1 (5)	N3—C7—N4—C6	0.3 (4)
C2—C3—C4—C5	−1.4 (5)	N3—C7—S1—C8	51.0 (3)
C3—C4—C5—C6	−176.0 (3)	N4—C6—N2—Co1	179.5 (2)
C3—C4—C5—N1	1.6 (5)	N4—C6—N2—N3	1.7 (3)
C4—C5—C6—N2	174.7 (3)	N4—C7—N3—Co1^i	−177.7 (2)
C4—C5—C6—N4	−3.4 (5)	N4—C7—N3—N2	0.7 (4)
C4—C5—N1—Co1	−174.5 (2)	N4—C7—S1—C8	−134.6 (3)
C4—C5—N1—C1	−0.4 (5)	O1^i—Co1—N1—C1	8.0 (3)
C5—C6—N2—Co1	1.2 (4)	O1^i—Co1—N1—C5	−178.7 (2)
C5—C6—N2—N3	−176.6 (3)	O1^i—Co1—N2—C6	12.4 (4)
C5—C6—N4—C7	177.0 (3)	O1^i—Co1—N2—N3	−170.9 (3)
C6—C5—N1—Co1	3.4 (3)	O1^i—Co1—O3—C10	−12.5 (3)
C6—C5—N1—C1	177.5 (3)	O2—C9—O1—Co1^i	−133.9 (3)
C6—N2—N3—Co1^i	177.22 (19)	O3—Co1—N1—C1	97.1 (3)
C6—N2—N3—C7	−1.4 (3)	O3—Co1—N1—C5	−89.5 (2)
C8—C9—O1—Co1^i	45.3 (4)	O3—Co1—N2—C6	92.7 (2)
C9—C8—S1—C7	−95.7 (3)	O3—Co1—N2—N3	−90.6 (3)
N1—Co1—N2—C6	0.5 (2)	O4—Co1—N1—C1	−81.8 (3)
N1—Co1—N2—N3	177.1 (3)	O4—Co1—N1—C5	91.6 (2)
N1—Co1—O3—C10	−98.2 (3)	O4—Co1—N2—C6	−86.5 (2)
N1—C1—C2—C3	1.3 (6)	O4—Co1—N2—N3	90.2 (3)
N1—C5—C6—N2	−3.1 (4)	O4—Co1—O3—C10	−35 (5)
N1—C5—C6—N4	178.7 (3)	S1—C7—N3—Co1^i	−3.0 (5)
N2—Co1—N1—C1	−175.5 (3)	S1—C7—N3—N2	175.5 (2)
N2—Co1—N1—C5	−2.2 (2)	S1—C7—N4—C6	−174.8 (2)
N2—Co1—O3—C10	−175.5 (3)	S1—C8—C9—O1	45.2 (4)
N2—C6—N4—C7	−1.3 (3)	S1—C8—C9—O2	−135.5 (3)
N3^i—Co1—N1—C1	−148.8 (9)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N4^ii	0.82	1.99	2.813 (3)	176
O3—H3A···O2^iii	0.84 (6)	1.83 (6)	2.657 (3)	169 (5)
O4—H4A···O5	0.85	1.90	2.742 (3)	167
O4—H4B···O2^iv	0.85	1.87	2.711 (3)	170

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

{µ-3-[(Carboxylatomethyl)sulfanyl]-5-(pyridin-2-yl)-4H-1,2,4-triazol-4-ido-κ²N¹,N⁵:N²,O}bis[diaquanickel(II)] methanol disolvate dihydrate (2)

Crystal data

[Ni2(C9H6N4O2S)2(H2O)4]·2CH4O·2H2O	Dx = 1.592 Mg m^−3
Mr = 379.04	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, I41/a	Cell parameters from 2774 reflections
a = 25.9178 (6) Å	θ = 5.0–71.1°
c = 9.4186 (3) Å	µ = 3.33 mm^−1
V = 6326.8 (3) Å^3	T = 293 K
Z = 16	Needle, clear light blue
F(000) = 3136	0.35 × 0.06 × 0.02 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Eos detector	2998 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	2584 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.017
Detector resolution: 16.0793 pixels mm^-1	θmax = 70.9°, θmin = 4.8°
ω scans	h = −31→20
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −31→19
Tmin = 0.708, Tmax = 1.000	l = −5→11
6205 measured 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 11.3278P] where P = (Fo^2 + 2Fc^2)/3
2998 reflections	(Δ/σ)max = 0.002
202 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.56 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. 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 > 2sigma(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
C1	0.62621 (10)	0.54575 (10)	0.3750 (3)	0.0452 (6)
H1	0.6450	0.5714	0.3293	0.054*
C2	0.63899 (11)	0.53296 (12)	0.5129 (3)	0.0554 (7)
H2	0.6660	0.5498	0.5587	0.067*
C3	0.61159 (12)	0.49538 (12)	0.5815 (3)	0.0562 (8)
H3	0.6197	0.4863	0.6744	0.067*
C4	0.57149 (10)	0.47095 (10)	0.5103 (3)	0.0448 (6)
H4	0.5520	0.4455	0.5546	0.054*
C5	0.56117 (9)	0.48542 (9)	0.3718 (2)	0.0327 (5)
C6	0.51970 (8)	0.46248 (8)	0.2875 (2)	0.0309 (5)
C7	0.45898 (10)	0.41799 (10)	0.2127 (3)	0.0426 (6)
C8	0.41489 (11)	0.34246 (10)	0.0452 (3)	0.0521 (8)
H8A	0.4492	0.3482	0.0070	0.063*
H8B	0.4095	0.3055	0.0528	0.063*
C9	0.37550 (9)	0.36507 (8)	−0.0535 (3)	0.0332 (5)
C10	0.5565 (2)	0.68384 (18)	0.4412 (5)	0.122 (2)
H10A	0.5415	0.7041	0.5160	0.184*
H10B	0.5546	0.7026	0.3535	0.184*
H10C	0.5919	0.6766	0.4633	0.184*
N1	0.58785 (7)	0.52255 (7)	0.3046 (2)	0.0335 (4)
N2	0.51009 (7)	0.47989 (7)	0.15716 (19)	0.0284 (4)
N3	0.46936 (7)	0.45106 (7)	0.1073 (2)	0.0324 (4)
N4	0.48905 (8)	0.42343 (8)	0.3277 (2)	0.0413 (5)
Ni1	0.561554 (13)	0.536693 (13)	0.09288 (4)	0.02623 (12)
O1	0.37598 (6)	0.41291 (6)	−0.07627 (18)	0.0345 (4)
O2	0.34293 (8)	0.33542 (7)	−0.1045 (3)	0.0664 (7)
O3	0.61271 (7)	0.48027 (7)	0.0287 (2)	0.0536 (5)
H3A	0.6057	0.4543	−0.0231	0.080*
H3B	0.6446	0.4859	0.0423	0.080*
O5	0.71385 (8)	0.52417 (8)	0.0399 (2)	0.0603 (5)
H5A	0.7372	0.5280	0.1026	0.090*
H5B	0.6952	0.5510	0.0494	0.090*
O4	0.51684 (6)	0.59610 (6)	0.17180 (18)	0.0397 (4)
H4A	0.5221	0.6001	0.2602	0.059*
H4B	0.4850	0.5895	0.1594	0.059*
O6	0.52968 (10)	0.63812 (9)	0.4282 (2)	0.0635 (6)
H6	0.5263	0.6249	0.5067	0.095*
S1	0.41022 (4)	0.37137 (4)	0.21818 (8)	0.0851 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0396 (13)	0.0461 (14)	0.0500 (15)	−0.0127 (11)	−0.0153 (12)	0.0019 (12)
C2	0.0498 (16)	0.0610 (18)	0.0555 (17)	−0.0166 (14)	−0.0255 (14)	0.0003 (14)
C3	0.0628 (18)	0.0608 (18)	0.0449 (15)	−0.0084 (15)	−0.0269 (14)	0.0072 (13)
C4	0.0498 (15)	0.0415 (14)	0.0430 (13)	−0.0062 (12)	−0.0147 (12)	0.0074 (11)
C5	0.0315 (11)	0.0301 (11)	0.0365 (12)	−0.0013 (9)	−0.0086 (9)	−0.0008 (9)
C6	0.0309 (11)	0.0295 (11)	0.0324 (11)	−0.0036 (9)	−0.0043 (9)	−0.0003 (9)
C7	0.0455 (14)	0.0477 (14)	0.0345 (12)	−0.0225 (12)	−0.0083 (11)	0.0063 (11)
C8	0.0553 (16)	0.0328 (13)	0.0683 (18)	−0.0147 (12)	−0.0342 (15)	0.0124 (12)
C9	0.0323 (11)	0.0280 (11)	0.0391 (12)	−0.0059 (9)	−0.0077 (10)	0.0014 (9)
C10	0.209 (6)	0.084 (3)	0.073 (3)	−0.056 (4)	−0.035 (3)	0.011 (2)
N1	0.0297 (9)	0.0351 (10)	0.0357 (10)	−0.0038 (8)	−0.0093 (8)	−0.0009 (8)
N2	0.0261 (9)	0.0292 (9)	0.0299 (9)	−0.0061 (7)	−0.0049 (7)	−0.0015 (7)
N3	0.0302 (9)	0.0355 (10)	0.0316 (9)	−0.0120 (8)	−0.0057 (8)	0.0009 (8)
N4	0.0462 (12)	0.0433 (11)	0.0344 (10)	−0.0170 (10)	−0.0099 (9)	0.0058 (9)
Ni1	0.02296 (19)	0.02468 (19)	0.0311 (2)	−0.00232 (14)	−0.00332 (15)	−0.00239 (14)
O1	0.0269 (7)	0.0258 (8)	0.0507 (10)	−0.0037 (6)	−0.0054 (7)	0.0020 (7)
O2	0.0732 (14)	0.0314 (9)	0.0946 (16)	−0.0170 (9)	−0.0568 (13)	0.0124 (10)
O3	0.0312 (9)	0.0390 (10)	0.0906 (15)	0.0013 (7)	−0.0007 (9)	−0.0284 (10)
O5	0.0527 (12)	0.0571 (12)	0.0710 (14)	0.0073 (10)	−0.0096 (10)	−0.0174 (11)
O4	0.0311 (8)	0.0423 (9)	0.0456 (10)	0.0054 (7)	−0.0064 (7)	−0.0137 (8)
O6	0.0906 (16)	0.0632 (13)	0.0367 (10)	−0.0081 (12)	−0.0119 (11)	−0.0004 (9)
S1	0.0997 (7)	0.1112 (7)	0.0445 (4)	−0.0825 (6)	−0.0237 (4)	0.0248 (4)

Geometric parameters (Å, º)

C1—H1	0.9300	C9—O2	1.238 (3)
C1—C2	1.381 (4)	C10—H10A	0.9600
C1—N1	1.338 (3)	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C2—C3	1.368 (4)	C10—O6	1.379 (4)
C3—H3	0.9300	N1—Ni1	2.1386 (19)
C3—C4	1.389 (4)	N2—N3	1.376 (2)
C4—H4	0.9300	N2—Ni1	2.0767 (17)
C4—C5	1.383 (3)	N3—Ni1^i	2.0731 (18)
C5—C6	1.463 (3)	Ni1—N3^i	2.0731 (18)
C5—N1	1.344 (3)	Ni1—O1^i	2.0861 (15)
C6—N2	1.331 (3)	Ni1—O3	2.0644 (17)
C6—N4	1.341 (3)	Ni1—O4	2.0654 (16)
C7—N3	1.339 (3)	O1—Ni1^i	2.0861 (15)
C7—N4	1.342 (3)	O3—H3A	0.8516
C7—S1	1.749 (2)	O3—H3B	0.8492
C8—H8A	0.9700	O5—H5A	0.8520
C8—H8B	0.9700	O5—H5B	0.8508
C8—C9	1.500 (3)	O4—H4A	0.8500
C8—S1	1.798 (3)	O4—H4B	0.8505
C9—O1	1.258 (3)	O6—H6	0.8200
C2—C1—H1	118.8	C1—N1—C5	118.1 (2)
N1—C1—H1	118.8	C1—N1—Ni1	128.46 (17)
N1—C1—C2	122.5 (3)	C5—N1—Ni1	113.47 (14)
C1—C2—H2	120.3	C6—N2—N3	105.91 (17)
C3—C2—C1	119.4 (2)	C6—N2—Ni1	112.89 (14)
C3—C2—H2	120.3	N3—N2—Ni1	141.10 (14)
C2—C3—H3	120.5	C7—N3—N2	104.41 (17)
C2—C3—C4	119.0 (3)	C7—N3—Ni1^i	134.00 (15)
C4—C3—H3	120.5	N2—N3—Ni1^i	121.59 (13)
C3—C4—H4	120.8	C6—N4—C7	101.27 (19)
C5—C4—C3	118.4 (2)	N2—Ni1—N1	79.13 (7)
C5—C4—H4	120.8	N2—Ni1—O1^i	164.62 (7)
C4—C5—C6	123.0 (2)	N3^i—Ni1—N1	175.77 (7)
N1—C5—C4	122.6 (2)	N3^i—Ni1—N2	97.21 (7)
N1—C5—C6	114.4 (2)	N3^i—Ni1—O1^i	97.81 (7)
N2—C6—C5	120.0 (2)	O1^i—Ni1—N1	85.98 (7)
N2—C6—N4	113.91 (19)	O3—Ni1—N1	86.97 (8)
N4—C6—C5	126.1 (2)	O3—Ni1—N2	89.76 (7)
N3—C7—N4	114.5 (2)	O3—Ni1—N3^i	95.17 (8)
N3—C7—S1	127.55 (18)	O3—Ni1—O1^i	85.60 (7)
N4—C7—S1	117.92 (18)	O3—Ni1—O4	173.61 (7)
H8A—C8—H8B	108.1	O4—Ni1—N1	88.34 (7)
C9—C8—H8A	109.5	O4—Ni1—N2	93.62 (7)
C9—C8—H8B	109.5	O4—Ni1—N3^i	89.80 (7)
C9—C8—S1	110.7 (2)	O4—Ni1—O1^i	89.75 (6)
S1—C8—H8A	109.5	C9—O1—Ni1^i	129.61 (15)
S1—C8—H8B	109.5	Ni1—O3—H3A	126.3
O1—C9—C8	118.9 (2)	Ni1—O3—H3B	117.3
O2—C9—C8	117.5 (2)	H3A—O3—H3B	115.5
O2—C9—O1	123.5 (2)	H5A—O5—H5B	103.6
H10A—C10—H10B	109.5	Ni1—O4—H4A	110.8
H10A—C10—H10C	109.5	Ni1—O4—H4B	110.3
H10B—C10—H10C	109.5	H4A—O4—H4B	108.2
O6—C10—H10A	109.5	C10—O6—H6	109.5
O6—C10—H10B	109.5	C7—S1—C8	102.27 (13)
O6—C10—H10C	109.5
C1—C2—C3—C4	0.0 (5)	C6—N2—Ni1—O1^i	12.2 (3)
C1—N1—Ni1—N2	−178.3 (2)	C6—N2—Ni1—O3	84.49 (16)
C1—N1—Ni1—N3^i	−148.2 (10)	C6—N2—Ni1—O4	−90.08 (16)
C1—N1—Ni1—O1^i	5.6 (2)	C8—C9—O1—Ni1^i	36.0 (3)
C1—N1—Ni1—O3	91.4 (2)	C9—C8—S1—C7	−98.1 (2)
C1—N1—Ni1—O4	−84.2 (2)	N1—C1—C2—C3	−0.3 (5)
C2—C1—N1—C5	−0.1 (4)	N1—C5—C6—N2	−2.1 (3)
C2—C1—N1—Ni1	179.5 (2)	N1—C5—C6—N4	177.0 (2)
C2—C3—C4—C5	0.6 (5)	N2—C6—N4—C7	−0.6 (3)
C3—C4—C5—C6	−179.6 (2)	N3—C7—N4—C6	−0.3 (3)
C3—C4—C5—N1	−1.0 (4)	N3—C7—S1—C8	45.0 (3)
C4—C5—C6—N2	176.7 (2)	N3—N2—Ni1—N1	−178.0 (2)
C4—C5—C6—N4	−4.3 (4)	N3—N2—Ni1—N3^i	4.1 (3)
C4—C5—N1—C1	0.8 (4)	N3—N2—Ni1—O1^i	−163.3 (2)
C4—C5—N1—Ni1	−179.0 (2)	N3—N2—Ni1—O3	−91.0 (2)
C5—C6—N2—N3	−179.6 (2)	N3—N2—Ni1—O4	94.4 (2)
C5—C6—N2—Ni1	3.3 (3)	N4—C6—N2—N3	1.2 (3)
C5—C6—N4—C7	−179.7 (2)	N4—C6—N2—Ni1	−175.88 (16)
C5—N1—Ni1—N2	1.43 (16)	N4—C7—N3—N2	1.0 (3)
C5—N1—Ni1—N3^i	31.5 (11)	N4—C7—N3—Ni1^i	−179.86 (18)
C5—N1—Ni1—O1^i	−174.69 (16)	N4—C7—S1—C8	−137.5 (2)
C5—N1—Ni1—O3	−88.90 (16)	Ni1—N2—N3—C7	174.5 (2)
C5—N1—Ni1—O4	95.44 (16)	Ni1—N2—N3—Ni1^i	−4.8 (3)
C6—C5—N1—C1	179.5 (2)	O2—C9—O1—Ni1^i	−146.6 (2)
C6—C5—N1—Ni1	−0.2 (2)	S1—C7—N3—N2	178.5 (2)
C6—N2—N3—C7	−1.2 (2)	S1—C7—N3—Ni1^i	−2.3 (4)
C6—N2—N3—Ni1^i	179.46 (15)	S1—C7—N4—C6	−178.08 (19)
C6—N2—Ni1—N1	−2.47 (15)	S1—C8—C9—O1	58.6 (3)
C6—N2—Ni1—N3^i	179.67 (15)	S1—C8—C9—O2	−118.9 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2^ii	0.85	1.76	2.606 (3)	171
O3—H3B···O5	0.85	2.05	2.860 (3)	159
O5—H5A···O5^iii	0.85	2.02	2.8434 (16)	163
O5—H5B···O1^i	0.85	2.08	2.863 (3)	152
O4—H4A···O6	0.85	1.87	2.670 (3)	155
O4—H4B···O2^iv	0.85	1.83	2.663 (2)	165
O6—H6···N4^v	0.82	2.04	2.840 (3)	165

Symmetry codes: (i) −x+1, −y+1, −z; (ii) y+1/4, −x+3/4, −z−1/4; (iii) y+1/4, −x+5/4, z+1/4; (iv) −y+3/4, x+1/4, z+1/4; (v) −x+1, −y+1, −z+1.