Aqua­bis(1,10-phenanthroline)(4,4′-sulfonyl­dibenzoato)nickel(II) dihydrate

Wu, H.-H.; Lian, F.-Y.; Yuan, D.-Q.; Hong, M.-C.

doi:10.1107/S1600536806051701

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Aquabis(1,10-phenanthroline)(4,4′-sulfonyldibenzoato)nickel(II) dihydrate

H.-H. Wu, F.-Y. Lian, D.-Q. Yuan and M.-C. Hong

In the title compound, [Ni(C₁₄H₈O₆S)(C₁₂H₈N₂)₂(H₂O)]·2H₂O, each Ni atom is coordinated by four N atoms [Ni—N = 2.083 (2)–2.096 (3) Å] from two 1,10-phenanthroline ligands and two O atoms [Ni—O = 2.032 (2) and 2.100 (2) Å] from a 4,4′-sulfonyldibenzoate ligand and a water molecule in a distorted octahedral geometry. The crystal structure exhibits intermolecular O—H

O hydrogen bonds and π–π stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051701/cv2154sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051701/cv2154Isup2.hkl Contains datablock I

CCDC reference: 633665

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.056
wR factor = 0.122
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N2  -NI1 -O1  -C1     90.20  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          8
            N4  -NI1 -N1  -C15  -165.60  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            N4  -NI1 -N1  -C26    23.50  0.90   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         16
            O1  -NI1 -N2  -C24   159.90  0.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         21
            O1  -NI1 -N2  -C25   -22.60  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         30
            O7  -NI1 -N3  -C27  -174.50  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         35
            O7  -NI1 -N3  -C38     7.10  1.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         39
            N1  -NI1 -N4  -C36  -105.90  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         44
            N1  -NI1 -N4  -C37    73.40  0.90   1.555   1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O

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
  12 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

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

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Aquabis(1,10-phenanthroline)(4,4'-sulfonyldibenzoato)nickel(II) dihydrate top

Crystal data top

[Ni(C₁₄H₈O₆S)(C₁₂H₈N₂)₂(H₂O)]·2H₂O	Z = 2
M_r = 777.43	F(000) = 804
Triclinic, P1	D_x = 1.520 Mg m⁻³
a = 8.8457 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.4789 (14) Å	Cell parameters from 3276 reflections
c = 16.673 (2) Å	θ = 2.4–27.5°
α = 105.894 (4)°	µ = 0.70 mm⁻¹
β = 105.091 (4)°	T = 293 K
γ = 91.836 (5)°	Prism, green
V = 1698.4 (3) Å³	0.35 × 0.25 × 0.10 mm

Data collection top

Mercury CCD diffractometer	7689 independent reflections
Radiation source: fine-focus sealed tube	5663 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 14.6306 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
φ? ω? scans	h = −11→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	k = −16→16
T_min = 0.792, T_max = 0.934	l = −21→21
13188 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0418P)² + 0.8893P] where P = (F_o² + 2F_c²)/3
7689 reflections	(Δ/σ)_max < 0.001
478 parameters	Δρ_max = 0.49 e Å⁻³
2 restraints	Δρ_min = −0.34 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.29581 (5)	0.26435 (3)	0.22952 (2)	0.03447 (12)
S1	−0.25633 (9)	−0.12158 (6)	0.43467 (5)	0.03760 (19)
O1	0.1371 (3)	0.18269 (16)	0.26739 (14)	0.0420 (5)
O2	0.0149 (3)	0.31978 (19)	0.33203 (19)	0.0691 (8)
O3	−0.9014 (3)	−0.44655 (17)	0.15404 (14)	0.0456 (5)
O4	−1.0106 (3)	−0.2960 (2)	0.20935 (16)	0.0552 (6)
O5	−0.1548 (3)	−0.20901 (18)	0.43217 (16)	0.0517 (6)
O6	−0.2873 (3)	−0.06434 (19)	0.51491 (14)	0.0502 (6)
O7	0.2017 (3)	0.41669 (16)	0.26634 (13)	0.0451 (5)
H7A	0.1650	0.4536	0.2311	0.054*
H7B	0.1257	0.3967	0.2835	0.054*
O8	−1.3178 (4)	−0.3031 (3)	0.0894 (2)	0.0902 (10)
H8B	−1.3002	−0.3612	0.0538	0.108*
H8A	−1.2415	−0.2833	0.1355	0.108*
O9	−1.1926 (3)	−0.5004 (2)	0.00396 (19)	0.0785 (8)
H9A	−1.1753	−0.5163	−0.0456	0.094*
H9B	−1.1052	−0.4822	0.0433	0.094*
N1	0.4555 (3)	0.3136 (2)	0.35388 (15)	0.0387 (6)
N2	0.4791 (3)	0.34821 (19)	0.20564 (16)	0.0379 (6)
N3	0.3744 (3)	0.10997 (19)	0.18140 (15)	0.0354 (6)
N4	0.1579 (3)	0.22000 (19)	0.10079 (15)	0.0354 (6)
C1	0.0435 (4)	0.2202 (2)	0.31045 (19)	0.0380 (7)
C2	−0.0392 (3)	0.1361 (2)	0.33908 (18)	0.0313 (6)
C3	−0.0172 (4)	0.0235 (2)	0.31225 (19)	0.0365 (7)
H3	0.0462	0.0007	0.2755	0.044*
C4	−0.0880 (3)	−0.0548 (2)	0.33929 (19)	0.0364 (7)
H4	−0.0748	−0.1302	0.3198	0.044*
C5	−0.1785 (3)	−0.0203 (2)	0.39545 (18)	0.0328 (6)
C6	−0.2020 (4)	0.0914 (2)	0.4236 (2)	0.0388 (7)
H6	−0.2628	0.1141	0.4619	0.047*
C7	−0.1341 (4)	0.1689 (2)	0.3942 (2)	0.0385 (7)
H7	−0.1521	0.2437	0.4115	0.046*
C8	−0.4407 (3)	−0.1801 (2)	0.35907 (19)	0.0343 (6)
C9	−0.5743 (4)	−0.1358 (3)	0.3732 (2)	0.0447 (8)
H9	−0.5669	−0.0704	0.4179	0.054*
C10	−0.7201 (4)	−0.1885 (3)	0.3206 (2)	0.0436 (8)
H10	−0.8107	−0.1576	0.3296	0.052*
C11	−0.7333 (4)	−0.2872 (2)	0.25427 (19)	0.0358 (7)
C12	−0.5965 (4)	−0.3286 (3)	0.2401 (2)	0.0445 (8)
H12	−0.6034	−0.3937	0.1951	0.053*
C13	−0.4498 (4)	−0.2756 (3)	0.2912 (2)	0.0465 (8)
H13	−0.3587	−0.3036	0.2801	0.056*
C14	−0.8950 (4)	−0.3467 (2)	0.20213 (19)	0.0370 (7)
C15	0.4431 (4)	0.2953 (3)	0.4267 (2)	0.0492 (8)
H15	0.3608	0.2449	0.4239	0.059*
C16	0.5500 (5)	0.3493 (3)	0.5078 (2)	0.0624 (11)
H16	0.5384	0.3341	0.5576	0.075*
C17	0.6704 (5)	0.4238 (3)	0.5133 (2)	0.0616 (11)
H17	0.7405	0.4609	0.5669	0.074*
C18	0.6882 (4)	0.4445 (3)	0.4378 (2)	0.0480 (8)
C19	0.8128 (4)	0.5199 (3)	0.4363 (3)	0.0601 (11)
H19	0.8834	0.5618	0.4884	0.072*
C20	0.8292 (4)	0.5311 (3)	0.3607 (3)	0.0584 (10)
H20	0.9124	0.5793	0.3617	0.070*
C21	0.7220 (4)	0.4706 (2)	0.2796 (2)	0.0479 (8)
C22	0.7336 (5)	0.4774 (3)	0.1985 (3)	0.0607 (10)
H22	0.8180	0.5210	0.1954	0.073*
C23	0.6215 (5)	0.4203 (3)	0.1246 (3)	0.0609 (10)
H23	0.6297	0.4229	0.0707	0.073*
C24	0.4946 (4)	0.3579 (3)	0.1309 (2)	0.0492 (8)
H24	0.4167	0.3210	0.0802	0.059*
C25	0.5929 (4)	0.4023 (2)	0.2793 (2)	0.0380 (7)
C26	0.5779 (4)	0.3863 (2)	0.35916 (19)	0.0379 (7)
C27	0.4784 (4)	0.0548 (3)	0.2223 (2)	0.0486 (8)
H27	0.5238	0.0855	0.2817	0.058*
C28	0.5231 (4)	−0.0468 (3)	0.1806 (2)	0.0545 (9)
H28	0.5964	−0.0827	0.2119	0.065*
C29	0.4585 (4)	−0.0929 (3)	0.0935 (2)	0.0529 (9)
H29	0.4883	−0.1603	0.0649	0.064*
C30	0.3471 (4)	−0.0387 (2)	0.0472 (2)	0.0412 (7)
C31	0.2681 (4)	−0.0809 (3)	−0.0430 (2)	0.0510 (9)
H31	0.2936	−0.1479	−0.0750	0.061*
C32	0.1580 (4)	−0.0272 (3)	−0.0835 (2)	0.0510 (9)
H32	0.1086	−0.0579	−0.1425	0.061*
C33	0.1154 (4)	0.0768 (2)	−0.03714 (19)	0.0410 (7)
C34	−0.0012 (4)	0.1363 (3)	−0.0752 (2)	0.0488 (8)
H34	−0.0555	0.1091	−0.1338	0.059*
C35	−0.0337 (4)	0.2338 (3)	−0.0253 (2)	0.0479 (8)
H35	−0.1101	0.2740	−0.0497	0.057*
C36	0.0481 (4)	0.2732 (3)	0.0625 (2)	0.0429 (7)
H36	0.0243	0.3400	0.0957	0.051*
C37	0.1909 (3)	0.1223 (2)	0.05146 (18)	0.0330 (6)
C38	0.3084 (4)	0.0635 (2)	0.09479 (19)	0.0349 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0406 (2)	0.0309 (2)	0.0278 (2)	−0.00624 (16)	0.00455 (16)	0.00766 (15)
S1	0.0365 (4)	0.0375 (4)	0.0377 (4)	−0.0014 (3)	0.0067 (3)	0.0133 (3)
O1	0.0500 (14)	0.0340 (11)	0.0440 (13)	−0.0039 (10)	0.0210 (11)	0.0082 (9)
O2	0.100 (2)	0.0377 (13)	0.097 (2)	0.0213 (14)	0.0628 (19)	0.0305 (13)
O3	0.0487 (14)	0.0373 (11)	0.0437 (13)	−0.0037 (10)	0.0094 (11)	0.0045 (10)
O4	0.0392 (14)	0.0531 (14)	0.0610 (16)	0.0046 (12)	0.0066 (12)	0.0037 (12)
O5	0.0448 (14)	0.0427 (12)	0.0665 (16)	0.0088 (11)	0.0040 (12)	0.0246 (11)
O6	0.0549 (15)	0.0576 (14)	0.0338 (12)	−0.0085 (12)	0.0095 (11)	0.0108 (10)
O7	0.0585 (15)	0.0350 (11)	0.0416 (13)	−0.0008 (10)	0.0123 (11)	0.0132 (9)
O8	0.074 (2)	0.093 (2)	0.099 (3)	0.0248 (18)	0.0105 (18)	0.0325 (19)
O9	0.076 (2)	0.098 (2)	0.0632 (19)	0.0006 (17)	0.0277 (16)	0.0182 (16)
N1	0.0490 (16)	0.0356 (13)	0.0282 (13)	0.0018 (12)	0.0065 (12)	0.0083 (10)
N2	0.0423 (15)	0.0326 (12)	0.0361 (14)	−0.0062 (11)	0.0083 (12)	0.0097 (10)
N3	0.0361 (14)	0.0367 (13)	0.0314 (13)	−0.0039 (11)	0.0046 (11)	0.0122 (10)
N4	0.0403 (15)	0.0324 (12)	0.0304 (13)	−0.0020 (11)	0.0051 (11)	0.0094 (10)
C1	0.0477 (19)	0.0330 (15)	0.0315 (16)	0.0000 (14)	0.0082 (14)	0.0099 (12)
C2	0.0310 (15)	0.0305 (14)	0.0298 (15)	0.0005 (12)	0.0044 (12)	0.0088 (11)
C3	0.0397 (17)	0.0336 (15)	0.0383 (17)	0.0067 (13)	0.0163 (14)	0.0085 (12)
C4	0.0339 (16)	0.0319 (14)	0.0407 (17)	0.0042 (13)	0.0098 (14)	0.0069 (12)
C5	0.0269 (15)	0.0332 (14)	0.0355 (16)	−0.0010 (12)	0.0039 (12)	0.0105 (12)
C6	0.0408 (18)	0.0359 (15)	0.0408 (17)	0.0057 (14)	0.0172 (15)	0.0073 (13)
C7	0.0416 (18)	0.0284 (14)	0.0446 (18)	0.0071 (13)	0.0130 (15)	0.0079 (13)
C8	0.0322 (16)	0.0310 (14)	0.0398 (17)	0.0000 (12)	0.0090 (13)	0.0117 (12)
C9	0.0439 (19)	0.0343 (16)	0.0468 (19)	0.0033 (14)	0.0103 (16)	−0.0007 (13)
C10	0.0350 (18)	0.0410 (17)	0.0488 (19)	0.0066 (14)	0.0110 (15)	0.0040 (14)
C11	0.0363 (17)	0.0323 (14)	0.0373 (16)	−0.0004 (13)	0.0092 (14)	0.0095 (12)
C12	0.045 (2)	0.0354 (16)	0.0466 (19)	0.0025 (15)	0.0169 (16)	−0.0015 (14)
C13	0.0390 (19)	0.0399 (17)	0.058 (2)	0.0029 (15)	0.0191 (17)	0.0044 (15)
C14	0.0428 (18)	0.0361 (15)	0.0331 (16)	−0.0006 (14)	0.0105 (14)	0.0123 (13)
C15	0.064 (2)	0.0484 (19)	0.0363 (18)	0.0082 (17)	0.0128 (17)	0.0155 (15)
C16	0.090 (3)	0.063 (2)	0.0310 (18)	0.025 (2)	0.0085 (19)	0.0147 (17)
C17	0.072 (3)	0.052 (2)	0.038 (2)	0.019 (2)	−0.0097 (18)	−0.0011 (16)
C18	0.046 (2)	0.0341 (16)	0.047 (2)	0.0119 (15)	−0.0030 (16)	−0.0005 (14)
C19	0.041 (2)	0.0381 (18)	0.072 (3)	0.0036 (16)	−0.0137 (19)	−0.0041 (17)
C20	0.036 (2)	0.0347 (17)	0.092 (3)	−0.0014 (15)	0.009 (2)	0.0060 (18)
C21	0.0361 (18)	0.0296 (15)	0.075 (3)	0.0033 (14)	0.0141 (18)	0.0113 (15)
C22	0.051 (2)	0.049 (2)	0.095 (3)	0.0008 (18)	0.036 (2)	0.027 (2)
C23	0.068 (3)	0.060 (2)	0.068 (3)	−0.001 (2)	0.035 (2)	0.026 (2)
C24	0.058 (2)	0.0482 (19)	0.0444 (19)	−0.0039 (17)	0.0159 (17)	0.0172 (15)
C25	0.0378 (17)	0.0268 (14)	0.0463 (18)	0.0018 (13)	0.0086 (14)	0.0089 (13)
C26	0.0393 (18)	0.0295 (14)	0.0369 (17)	0.0038 (13)	0.0019 (14)	0.0050 (12)
C27	0.045 (2)	0.052 (2)	0.0427 (19)	0.0028 (16)	−0.0008 (16)	0.0175 (16)
C28	0.052 (2)	0.054 (2)	0.057 (2)	0.0142 (18)	0.0073 (18)	0.0222 (18)
C29	0.055 (2)	0.0418 (18)	0.061 (2)	0.0088 (17)	0.0188 (19)	0.0104 (16)
C30	0.0438 (19)	0.0342 (15)	0.0438 (18)	−0.0015 (14)	0.0136 (15)	0.0077 (13)
C31	0.064 (2)	0.0419 (18)	0.0426 (19)	0.0023 (17)	0.0188 (18)	0.0019 (15)
C32	0.067 (2)	0.0476 (19)	0.0289 (17)	−0.0036 (18)	0.0071 (16)	0.0027 (14)
C33	0.049 (2)	0.0377 (16)	0.0322 (16)	−0.0075 (14)	0.0084 (14)	0.0074 (13)
C34	0.055 (2)	0.0514 (19)	0.0327 (17)	−0.0063 (17)	0.0004 (16)	0.0138 (15)
C35	0.052 (2)	0.0494 (19)	0.0394 (18)	0.0023 (16)	0.0007 (16)	0.0197 (15)
C36	0.048 (2)	0.0358 (16)	0.0416 (18)	0.0030 (15)	0.0047 (15)	0.0131 (13)
C37	0.0369 (17)	0.0295 (14)	0.0294 (15)	−0.0074 (12)	0.0055 (13)	0.0081 (11)
C38	0.0373 (17)	0.0313 (14)	0.0340 (16)	−0.0065 (13)	0.0079 (13)	0.0092 (12)

Geometric parameters (Å, º) top

Ni1—O1	2.032 (2)	C11—C12	1.382 (4)
Ni1—N2	2.083 (2)	C11—C14	1.511 (4)
Ni1—N4	2.084 (2)	C12—C13	1.381 (4)
Ni1—N3	2.090 (2)	C12—H12	0.9300
Ni1—N1	2.096 (2)	C13—H13	0.9300
Ni1—O7	2.101 (2)	C15—C16	1.404 (5)
S1—O6	1.434 (2)	C15—H15	0.9300
S1—O5	1.434 (2)	C16—C17	1.359 (6)
S1—C5	1.769 (3)	C16—H16	0.9300
S1—C8	1.769 (3)	C17—C18	1.398 (5)
O1—C1	1.253 (3)	C17—H17	0.9300
O2—C1	1.250 (3)	C18—C26	1.402 (4)
O3—C14	1.274 (3)	C18—C19	1.435 (5)
O4—C14	1.234 (4)	C19—C20	1.349 (5)
O7—H7A	0.8501	C19—H19	0.9300
O7—H7B	0.8500	C20—C21	1.424 (5)
O8—H8B	0.8500	C20—H20	0.9300
O8—H8A	0.8501	C21—C25	1.402 (4)
O9—H9A	0.8500	C21—C22	1.407 (5)
O9—H9B	0.8500	C22—C23	1.358 (5)
N1—C15	1.325 (4)	C22—H22	0.9300
N1—C26	1.359 (4)	C23—C24	1.388 (5)
N2—C24	1.325 (4)	C23—H23	0.9300
N2—C25	1.355 (4)	C24—H24	0.9300
N3—C27	1.325 (4)	C25—C26	1.437 (4)
N3—C38	1.358 (4)	C27—C28	1.393 (5)
N4—C36	1.319 (4)	C27—H27	0.9300
N4—C37	1.359 (4)	C28—C29	1.362 (5)
C1—C2	1.507 (4)	C28—H28	0.9300
C2—C3	1.389 (4)	C29—C30	1.400 (5)
C2—C7	1.392 (4)	C29—H29	0.9300
C3—C4	1.378 (4)	C30—C38	1.410 (4)
C3—H3	0.9300	C30—C31	1.422 (4)
C4—C5	1.376 (4)	C31—C32	1.342 (5)
C4—H4	0.9300	C31—H31	0.9300
C5—C6	1.385 (4)	C32—C33	1.434 (4)
C6—C7	1.383 (4)	C32—H32	0.9300
C6—H6	0.9300	C33—C37	1.398 (4)
C7—H7	0.9300	C33—C34	1.408 (5)
C8—C9	1.369 (4)	C34—C35	1.359 (5)
C8—C13	1.384 (4)	C34—H34	0.9300
C9—C10	1.381 (4)	C35—C36	1.393 (4)
C9—H9	0.9300	C35—H35	0.9300
C10—C11	1.389 (4)	C36—H36	0.9300
C10—H10	0.9300	C37—C38	1.445 (4)

O1—Ni1—N2	172.65 (10)	C8—C13—H13	120.6
O1—Ni1—N4	93.11 (9)	O4—C14—O3	124.8 (3)
N2—Ni1—N4	93.95 (9)	O4—C14—C11	118.2 (3)
O1—Ni1—N3	88.40 (9)	O3—C14—C11	117.0 (3)
N2—Ni1—N3	90.82 (9)	N1—C15—C16	122.3 (3)
N4—Ni1—N3	79.99 (9)	N1—C15—H15	118.9
O1—Ni1—N1	93.08 (9)	C16—C15—H15	118.9
N2—Ni1—N1	79.81 (10)	C17—C16—C15	119.8 (3)
N4—Ni1—N1	173.57 (10)	C17—C16—H16	120.1
N3—Ni1—N1	98.44 (9)	C15—C16—H16	120.1
O1—Ni1—O7	91.59 (8)	C16—C17—C18	119.6 (3)
N2—Ni1—O7	89.87 (9)	C16—C17—H17	120.2
N4—Ni1—O7	94.64 (9)	C18—C17—H17	120.2
N3—Ni1—O7	174.62 (9)	C17—C18—C26	117.2 (3)
N1—Ni1—O7	86.92 (9)	C17—C18—C19	124.0 (3)
O6—S1—O5	119.73 (15)	C26—C18—C19	118.8 (3)
O6—S1—C5	108.08 (13)	C20—C19—C18	121.1 (3)
O5—S1—C5	107.59 (14)	C20—C19—H19	119.4
O6—S1—C8	106.91 (14)	C18—C19—H19	119.4
O5—S1—C8	107.40 (14)	C19—C20—C21	121.4 (3)
C5—S1—C8	106.42 (13)	C19—C20—H20	119.3
C1—O1—Ni1	130.42 (19)	C21—C20—H20	119.3
Ni1—O7—H7A	122.9	C25—C21—C22	117.0 (3)
Ni1—O7—H7B	101.6	C25—C21—C20	118.7 (3)
H7A—O7—H7B	107.1	C22—C21—C20	124.3 (3)
H8B—O8—H8A	110.3	C23—C22—C21	120.0 (3)
H9A—O9—H9B	109.2	C23—C22—H22	120.0
C15—N1—C26	117.9 (3)	C21—C22—H22	120.0
C15—N1—Ni1	129.6 (2)	C22—C23—C24	119.0 (3)
C26—N1—Ni1	111.85 (19)	C22—C23—H23	120.5
C24—N2—C25	118.1 (3)	C24—C23—H23	120.5
C24—N2—Ni1	129.2 (2)	N2—C24—C23	123.2 (3)
C25—N2—Ni1	112.66 (19)	N2—C24—H24	118.4
C27—N3—C38	117.6 (3)	C23—C24—H24	118.4
C27—N3—Ni1	129.7 (2)	N2—C25—C21	122.6 (3)
C38—N3—Ni1	112.73 (19)	N2—C25—C26	117.2 (3)
C36—N4—C37	117.8 (3)	C21—C25—C26	120.2 (3)
C36—N4—Ni1	129.3 (2)	N1—C26—C18	123.2 (3)
C37—N4—Ni1	112.90 (19)	N1—C26—C25	117.3 (3)
O2—C1—O1	126.0 (3)	C18—C26—C25	119.5 (3)
O2—C1—C2	118.1 (3)	N3—C27—C28	123.2 (3)
O1—C1—C2	115.9 (3)	N3—C27—H27	118.4
C3—C2—C7	118.8 (3)	C28—C27—H27	118.4
C3—C2—C1	119.7 (3)	C29—C28—C27	119.3 (3)
C7—C2—C1	121.5 (3)	C29—C28—H28	120.3
C4—C3—C2	121.0 (3)	C27—C28—H28	120.3
C4—C3—H3	119.5	C28—C29—C30	119.9 (3)
C2—C3—H3	119.5	C28—C29—H29	120.1
C5—C4—C3	119.4 (3)	C30—C29—H29	120.1
C5—C4—H4	120.3	C29—C30—C38	116.9 (3)
C3—C4—H4	120.3	C29—C30—C31	124.7 (3)
C4—C5—C6	120.9 (3)	C38—C30—C31	118.4 (3)
C4—C5—S1	118.1 (2)	C32—C31—C30	122.1 (3)
C6—C5—S1	120.9 (2)	C32—C31—H31	118.9
C7—C6—C5	119.2 (3)	C30—C31—H31	118.9
C7—C6—H6	120.4	C31—C32—C33	121.0 (3)
C5—C6—H6	120.4	C31—C32—H32	119.5
C6—C7—C2	120.6 (3)	C33—C32—H32	119.5
C6—C7—H7	119.7	C37—C33—C34	117.1 (3)
C2—C7—H7	119.7	C37—C33—C32	119.0 (3)
C9—C8—C13	120.7 (3)	C34—C33—C32	123.9 (3)
C9—C8—S1	119.1 (2)	C35—C34—C33	119.3 (3)
C13—C8—S1	119.9 (2)	C35—C34—H34	120.3
C8—C9—C10	119.7 (3)	C33—C34—H34	120.3
C8—C9—H9	120.2	C34—C35—C36	119.7 (3)
C10—C9—H9	120.2	C34—C35—H35	120.2
C9—C10—C11	120.9 (3)	C36—C35—H35	120.2
C9—C10—H10	119.6	N4—C36—C35	123.0 (3)
C11—C10—H10	119.6	N4—C36—H36	118.5
C12—C11—C10	118.2 (3)	C35—C36—H36	118.5
C12—C11—C14	122.5 (3)	N4—C37—C33	123.2 (3)
C10—C11—C14	119.3 (3)	N4—C37—C38	117.1 (3)
C11—C12—C13	121.5 (3)	C33—C37—C38	119.7 (3)
C11—C12—H12	119.2	N3—C38—C30	123.1 (3)
C13—C12—H12	119.2	N3—C38—C37	117.1 (3)
C12—C13—C8	118.9 (3)	C30—C38—C37	119.8 (3)
C12—C13—H13	120.6

N2—Ni1—O1—C1	90.2 (7)	C9—C8—C13—C12	−2.9 (5)
N4—Ni1—O1—C1	−105.9 (3)	S1—C8—C13—C12	171.2 (3)
N3—Ni1—O1—C1	174.2 (3)	C12—C11—C14—O4	−168.8 (3)
N1—Ni1—O1—C1	75.8 (3)	C10—C11—C14—O4	12.7 (4)
O7—Ni1—O1—C1	−11.2 (3)	C12—C11—C14—O3	11.6 (4)
O1—Ni1—N1—C15	−1.3 (3)	C10—C11—C14—O3	−166.8 (3)
N2—Ni1—N1—C15	−179.4 (3)	C26—N1—C15—C16	0.9 (5)
N4—Ni1—N1—C15	−165.6 (7)	Ni1—N1—C15—C16	−169.5 (2)
N3—Ni1—N1—C15	−90.1 (3)	N1—C15—C16—C17	0.5 (5)
O7—Ni1—N1—C15	90.2 (3)	C15—C16—C17—C18	−1.1 (5)
O1—Ni1—N1—C26	−172.2 (2)	C16—C17—C18—C26	0.3 (5)
N2—Ni1—N1—C26	9.69 (19)	C16—C17—C18—C19	−178.8 (3)
N4—Ni1—N1—C26	23.5 (9)	C17—C18—C19—C20	175.9 (3)
N3—Ni1—N1—C26	99.0 (2)	C26—C18—C19—C20	−3.2 (5)
O7—Ni1—N1—C26	−80.7 (2)	C18—C19—C20—C21	1.4 (5)
O1—Ni1—N2—C24	159.9 (6)	C19—C20—C21—C25	3.0 (5)
N4—Ni1—N2—C24	−4.0 (3)	C19—C20—C21—C22	−179.2 (3)
N3—Ni1—N2—C24	76.0 (3)	C25—C21—C22—C23	0.8 (5)
N1—Ni1—N2—C24	174.5 (3)	C20—C21—C22—C23	−177.1 (3)
O7—Ni1—N2—C24	−98.6 (3)	C21—C22—C23—C24	1.5 (6)
O1—Ni1—N2—C25	−22.6 (8)	C25—N2—C24—C23	0.1 (5)
N4—Ni1—N2—C25	173.5 (2)	Ni1—N2—C24—C23	177.5 (3)
N3—Ni1—N2—C25	−106.4 (2)	C22—C23—C24—N2	−2.1 (6)
N1—Ni1—N2—C25	−8.00 (19)	C24—N2—C25—C21	2.4 (4)
O7—Ni1—N2—C25	78.9 (2)	Ni1—N2—C25—C21	−175.4 (2)
O1—Ni1—N3—C27	−84.5 (3)	C24—N2—C25—C26	−177.0 (3)
N2—Ni1—N3—C27	88.1 (3)	Ni1—N2—C25—C26	5.2 (3)
N4—Ni1—N3—C27	−178.0 (3)	C22—C21—C25—N2	−2.8 (4)
N1—Ni1—N3—C27	8.3 (3)	C20—C21—C25—N2	175.2 (3)
O7—Ni1—N3—C27	−174.5 (8)	C22—C21—C25—C26	176.5 (3)
O1—Ni1—N3—C38	97.0 (2)	C20—C21—C25—C26	−5.5 (4)
N2—Ni1—N3—C38	−90.3 (2)	C15—N1—C26—C18	−1.8 (4)
N4—Ni1—N3—C38	3.58 (19)	Ni1—N1—C26—C18	170.3 (2)
N1—Ni1—N3—C38	−170.10 (19)	C15—N1—C26—C25	177.9 (3)
O7—Ni1—N3—C38	7.1 (10)	Ni1—N1—C26—C25	−10.1 (3)
O1—Ni1—N4—C36	89.8 (3)	C17—C18—C26—N1	1.2 (4)
N2—Ni1—N4—C36	−92.3 (3)	C19—C18—C26—N1	−179.7 (3)
N3—Ni1—N4—C36	177.6 (3)	C17—C18—C26—C25	−178.5 (3)
N1—Ni1—N4—C36	−105.9 (8)	C19—C18—C26—C25	0.7 (4)
O7—Ni1—N4—C36	−2.1 (3)	N2—C25—C26—N1	3.4 (4)
O1—Ni1—N4—C37	−90.94 (19)	C21—C25—C26—N1	−176.0 (3)
N2—Ni1—N4—C37	87.02 (19)	N2—C25—C26—C18	−176.9 (3)
N3—Ni1—N4—C37	−3.12 (18)	C21—C25—C26—C18	3.7 (4)
N1—Ni1—N4—C37	73.4 (9)	C38—N3—C27—C28	0.5 (5)
O7—Ni1—N4—C37	177.21 (19)	Ni1—N3—C27—C28	−177.8 (2)
Ni1—O1—C1—O2	8.7 (5)	N3—C27—C28—C29	0.2 (5)
Ni1—O1—C1—C2	−170.40 (19)	C27—C28—C29—C30	−0.7 (5)
O2—C1—C2—C3	176.4 (3)	C28—C29—C30—C38	0.3 (5)
O1—C1—C2—C3	−4.4 (4)	C28—C29—C30—C31	−177.7 (3)
O2—C1—C2—C7	−5.5 (5)	C29—C30—C31—C32	177.5 (3)
O1—C1—C2—C7	173.7 (3)	C38—C30—C31—C32	−0.5 (5)
C7—C2—C3—C4	0.1 (4)	C30—C31—C32—C33	0.4 (5)
C1—C2—C3—C4	178.3 (3)	C31—C32—C33—C37	0.2 (5)
C2—C3—C4—C5	−1.7 (5)	C31—C32—C33—C34	−178.7 (3)
C3—C4—C5—C6	1.4 (5)	C37—C33—C34—C35	0.6 (5)
C3—C4—C5—S1	−175.7 (2)	C32—C33—C34—C35	179.4 (3)
O6—S1—C5—C4	156.6 (2)	C33—C34—C35—C36	−0.3 (5)
O5—S1—C5—C4	26.0 (3)	C37—N4—C36—C35	−0.2 (5)
C8—S1—C5—C4	−88.9 (3)	Ni1—N4—C36—C35	179.0 (2)
O6—S1—C5—C6	−20.5 (3)	C34—C35—C36—N4	0.1 (5)
O5—S1—C5—C6	−151.1 (2)	C36—N4—C37—C33	0.5 (4)
C8—S1—C5—C6	94.0 (3)	Ni1—N4—C37—C33	−178.8 (2)
C4—C5—C6—C7	0.4 (5)	C36—N4—C37—C38	−178.4 (3)
S1—C5—C6—C7	177.4 (2)	Ni1—N4—C37—C38	2.2 (3)
C5—C6—C7—C2	−2.0 (5)	C34—C33—C37—N4	−0.7 (4)
C3—C2—C7—C6	1.7 (5)	C32—C33—C37—N4	−179.7 (3)
C1—C2—C7—C6	−176.4 (3)	C34—C33—C37—C38	178.2 (3)
O6—S1—C8—C9	21.8 (3)	C32—C33—C37—C38	−0.8 (4)
O5—S1—C8—C9	151.5 (2)	C27—N3—C38—C30	−0.9 (4)
C5—S1—C8—C9	−93.5 (3)	Ni1—N3—C38—C30	177.8 (2)
O6—S1—C8—C13	−152.4 (3)	C27—N3—C38—C37	177.8 (3)
O5—S1—C8—C13	−22.8 (3)	Ni1—N3—C38—C37	−3.5 (3)
C5—S1—C8—C13	92.2 (3)	C29—C30—C38—N3	0.4 (4)
C13—C8—C9—C10	1.8 (5)	C31—C30—C38—N3	178.6 (3)
S1—C8—C9—C10	−172.4 (3)	C29—C30—C38—C37	−178.2 (3)
C8—C9—C10—C11	1.1 (5)	C31—C30—C38—C37	0.0 (4)
C9—C10—C11—C12	−2.7 (5)	N4—C37—C38—N3	0.9 (4)
C9—C10—C11—C14	175.8 (3)	C33—C37—C38—N3	−178.1 (3)
C10—C11—C12—C13	1.5 (5)	N4—C37—C38—C30	179.6 (3)
C14—C11—C12—C13	−177.0 (3)	C33—C37—C38—C30	0.7 (4)
C11—C12—C13—C8	1.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O3ⁱ	0.85	2.02	2.865 (3)	174
O7—H7B···O2	0.85	1.82	2.633 (3)	159
O8—H8B···O9	0.85	2.08	2.897 (4)	160
O8—H8A···O4	0.85	2.13	2.907 (4)	152
O9—H9A···O3ⁱⁱ	0.85	2.04	2.879 (3)	171
O9—H9B···O3	0.85	2.15	2.993 (4)	171

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

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