9-(2-Carboxy­phen­yl)-3,6-bis­(diethyl­amino)xanthylium bis­(2-thioxo-1,3-dithiole-4,5-dithiol­ato)nickelate(III)

In the title compound, (C₂₈H₃₁N₂O₃)[Ni(C₃S₅)₂], the two symmetry-independent anions are located on inversion centres and adopt planar conformations with an approximate D_2h symmetry. The Ni atoms both show a square-planar coordination geometry. The xanthene system is planar, with the attached benzene ring twisted by 75.8 (11)° from the xanthene plane. One of the four ethyl groups of the cation is disordered. The xanthylium cation and one of the symmetry-independent 2-thioxo-1,3-dithiole-4,5-dithiol­ate anions are arranged into columns, with the anion sandwiched between hydrogen-bonded dimers of the cation. The second symmetry-independent anion is enclosed between these columns.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.013 Å
• Disorder in main residue
• R factor = 0.088
• wR factor = 0.287
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT213_ALERT_2_B Atom C34A    has ADP max/min Ratio .............       4.30 prola
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.67 Ratio

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.287
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT084_ALERT_2_C High R2 Value ..................................       0.29
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.06
PLAT213_ALERT_2_C Atom N2      has ADP max/min Ratio .............       3.50 prola
PLAT213_ALERT_2_C Atom C31     has ADP max/min Ratio .............       3.10 prola
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.29 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C33A
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         13
PLAT410_ALERT_2_C Short Intra H...H Contact  H31A   ..  H33D    ..       1.92 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      40.00 Deg.
              C33B -N2   -C33A    1.555   1.555   1.555

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

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

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

9-(2-Carboxyphenyl)-3,6-bis(diethylamino)xanthylium bis(2-thioxo-1,3-dithiole-4,5-dithiolato)nickelate(III)

Crystal data

C28H31N2O3·C6NiS10	Z = 2
Mr = 894.92	F(000) = 922
Triclinic, P1	Dx = 1.553 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.187 (4) Å	Cell parameters from 2181 reflections
b = 10.752 (4) Å	θ = 2.5–26.6°
c = 18.285 (7) Å	µ = 1.09 mm^−1
α = 105.729 (7)°	T = 100 K
β = 96.342 (7)°	Plate, black
γ = 91.138 (8)°	0.25 × 0.24 × 0.05 mm
V = 1913.5 (13) Å^3

Data collection

Bruker SMART CCD area detector diffractometer	8212 independent reflections
Radiation source: fine-focus sealed tube	4839 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
Detector resolution: 8.366 pixels mm^-1	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −13→11
Absorption correction: analytical (XPREP; Bruker, 2001)	k = −12→13
Tmin = 0.772, Tmax = 0.948	l = −18→23
11478 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.088	H-atom parameters constrained
wR(F^2) = 0.287	w = 1/[σ^2(Fo^2) + (0.1434P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.003
8212 reflections	Δρmax = 1.53 e Å^−3
479 parameters	Δρmin = −0.74 e Å^−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0052 (14)

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	0.0213 (4)
Ni2	0.0000	0.0000	0.0000	0.0252 (4)
S5	0.5250 (2)	0.5910 (2)	0.41095 (13)	0.0262 (5)
S8	0.2649 (2)	0.3213 (2)	0.18965 (13)	0.0279 (5)
S10	0.1720 (2)	0.0588 (2)	0.08365 (14)	0.0288 (5)
S4	0.5335 (2)	0.3090 (2)	0.43047 (13)	0.0246 (5)
S9	−0.0734 (2)	0.1916 (2)	0.02402 (13)	0.0279 (5)
S3	0.5791 (2)	0.4773 (2)	0.24786 (13)	0.0316 (6)
S2	0.5880 (2)	0.2186 (2)	0.26551 (14)	0.0317 (6)
S7	0.0362 (2)	0.4422 (2)	0.13869 (14)	0.0372 (6)
S6	0.2452 (3)	0.6034 (3)	0.25445 (16)	0.0451 (7)
S1	0.6409 (3)	0.2626 (3)	0.11830 (14)	0.0489 (8)
O3	1.0270 (5)	0.0007 (5)	0.4149 (3)	0.0214 (12)
O2	1.1829 (6)	0.0175 (6)	0.5131 (3)	0.0248 (13)
H2	1.1173	0.0282	0.5379	0.037*
O1	0.8956 (5)	0.1679 (5)	0.2309 (3)	0.0225 (13)
C14	1.0191 (8)	−0.0193 (8)	0.2317 (4)	0.0205 (17)
C19	0.9103 (8)	0.0392 (8)	0.2047 (5)	0.0229 (18)
C12	1.0983 (8)	0.1890 (8)	0.3132 (5)	0.0196 (17)
C5	0.0437 (9)	0.2767 (8)	0.0963 (5)	0.0253 (19)
C20	1.2329 (8)	−0.0005 (7)	0.3181 (5)	0.0184 (17)
C13	1.1125 (8)	0.0582 (8)	0.2896 (5)	0.0193 (17)
C22	1.4515 (8)	−0.0742 (8)	0.2991 (5)	0.0247 (19)
H22	1.5196	−0.0946	0.2669	0.030*
C10	1.1679 (8)	0.4067 (8)	0.3923 (5)	0.0243 (18)
H10	1.2332	0.4640	0.4269	0.029*
C25	1.2521 (8)	−0.0172 (7)	0.3915 (5)	0.0219 (18)
C21	1.3352 (8)	−0.0279 (8)	0.2727 (5)	0.0237 (18)
H21	1.3251	−0.0148	0.2231	0.028*
C3	0.5516 (8)	0.4607 (9)	0.3369 (5)	0.0252 (19)
C7	0.9873 (8)	0.2432 (8)	0.2843 (5)	0.0246 (19)
C11	1.1892 (8)	0.2794 (8)	0.3687 (5)	0.0233 (18)
H11	1.2673	0.2485	0.3896	0.028*
C6	0.1505 (8)	0.2197 (9)	0.1200 (5)	0.028 (2)
C24	1.3688 (8)	−0.0620 (8)	0.4180 (4)	0.0200 (17)
H24	1.3806	−0.0732	0.4681	0.024*
C23	1.4698 (8)	−0.0909 (8)	0.3707 (5)	0.027 (2)
H23	1.5504	−0.1220	0.3885	0.033*
C18	0.8120 (8)	−0.0280 (9)	0.1498 (5)	0.0265 (19)
H18	0.7417	0.0166	0.1314	0.032*
C8	0.9589 (8)	0.3725 (8)	0.3111 (6)	0.032 (2)
H8	0.8790	0.4033	0.2920	0.038*
C2	0.5557 (8)	0.3397 (8)	0.3454 (5)	0.0235 (18)
C26	1.1433 (8)	0.0026 (7)	0.4405 (5)	0.0199 (17)
C27	1.1231 (9)	0.6781 (8)	0.4420 (6)	0.036 (2)
H27A	1.1086	0.7616	0.4300	0.043*
H27B	1.2116	0.6506	0.4287	0.043*
C9	1.0486 (8)	0.4561 (8)	0.3661 (5)	0.027 (2)
C15	1.0237 (9)	−0.1537 (9)	0.2016 (5)	0.029 (2)
H15	1.0957	−0.1972	0.2191	0.035*
C16	0.9276 (9)	−0.2222 (9)	0.1481 (5)	0.035 (2)
H16	0.9349	−0.3127	0.1280	0.042*
C17	0.8158 (9)	−0.1628 (10)	0.1208 (6)	0.039 (3)
N1	1.0228 (7)	0.5815 (7)	0.3961 (5)	0.0328 (19)
C28	1.1191 (9)	0.6969 (9)	0.5276 (6)	0.038 (2)
H28A	1.0311	0.7225	0.5408	0.057*
H28B	1.1854	0.7646	0.5567	0.057*
H28C	1.1383	0.6156	0.5402	0.057*
C4	0.1868 (9)	0.4627 (9)	0.1959 (5)	0.034 (2)
C1	0.6043 (8)	0.3160 (10)	0.2059 (5)	0.031 (2)
C32	0.4979 (10)	−0.1453 (12)	0.0848 (6)	0.048 (3)
H32A	0.4756	−0.2230	0.1000	0.072*
H32B	0.4205	−0.1223	0.0553	0.072*
H32C	0.5245	−0.0737	0.1307	0.072*
C30	0.8748 (10)	0.6866 (10)	0.3161 (7)	0.049 (3)
H30A	0.9442	0.7546	0.3228	0.073*
H30B	0.7880	0.7238	0.3135	0.073*
H30C	0.8812	0.6191	0.2685	0.073*
C31	0.6108 (11)	−0.1713 (15)	0.0362 (6)	0.066 (4)
H31A	0.5768	−0.2283	−0.0149	0.079*
H31B	0.6433	−0.0884	0.0292	0.079*
C29	0.8917 (8)	0.6294 (9)	0.3819 (6)	0.031 (2)
H29A	0.8738	0.6957	0.4285	0.038*
H29B	0.8250	0.5569	0.3725	0.038*
N2	0.7192 (8)	−0.2301 (9)	0.0679 (6)	0.068 (4)
C33A	0.696 (3)	−0.388 (3)	0.0649 (17)	0.027 (7)	0.48 (3)
H33A	0.7365	−0.4036	0.1131	0.032*	0.48 (3)
H33B	0.6005	−0.4127	0.0578	0.032*	0.48 (3)
C34A	0.760 (2)	−0.4640 (17)	−0.0008 (11)	0.037 (7)	0.48 (3)
H34A	0.7302	−0.4367	−0.0466	0.056*	0.48 (3)
H34B	0.7365	−0.5562	−0.0100	0.056*	0.48 (3)
H34C	0.8565	−0.4494	0.0108	0.056*	0.48 (3)
C33B	0.737 (2)	−0.3580 (15)	0.0188 (10)	0.045 (7)	0.52 (3)
H33C	0.8318	−0.3750	0.0147	0.054*	0.52 (3)
H33D	0.6882	−0.3734	−0.0329	0.054*	0.52 (3)
C34B	0.675 (4)	−0.435 (3)	0.067 (2)	0.041 (8)	0.52 (3)
H34D	0.7209	−0.4095	0.1193	0.061*	0.52 (3)
H34E	0.6839	−0.5278	0.0444	0.061*	0.52 (3)
H34F	0.5815	−0.4172	0.0681	0.061*	0.52 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0211 (8)	0.0222 (8)	0.0188 (8)	0.0001 (6)	0.0017 (6)	0.0029 (6)
Ni2	0.0258 (8)	0.0259 (9)	0.0252 (9)	0.0017 (7)	0.0003 (7)	0.0102 (7)
S5	0.0323 (11)	0.0236 (11)	0.0218 (12)	−0.0013 (9)	0.0021 (9)	0.0052 (9)
S8	0.0262 (11)	0.0320 (13)	0.0242 (12)	0.0062 (9)	0.0018 (9)	0.0056 (9)
S10	0.0271 (11)	0.0241 (12)	0.0359 (13)	0.0015 (9)	−0.0046 (10)	0.0127 (10)
S4	0.0240 (10)	0.0239 (11)	0.0245 (12)	0.0018 (9)	0.0028 (9)	0.0042 (9)
S9	0.0284 (11)	0.0307 (12)	0.0237 (12)	0.0059 (9)	−0.0007 (9)	0.0073 (9)
S3	0.0301 (12)	0.0423 (14)	0.0223 (12)	0.0014 (10)	0.0036 (10)	0.0086 (10)
S2	0.0275 (11)	0.0344 (13)	0.0285 (13)	0.0044 (10)	0.0059 (10)	−0.0008 (10)
S7	0.0357 (13)	0.0380 (14)	0.0283 (13)	0.0176 (11)	−0.0050 (11)	−0.0047 (10)
S6	0.0421 (15)	0.0389 (15)	0.0391 (16)	0.0156 (12)	−0.0099 (12)	−0.0100 (12)
S1	0.0424 (15)	0.084 (2)	0.0182 (13)	0.0302 (15)	0.0062 (11)	0.0081 (13)
O3	0.022 (3)	0.026 (3)	0.016 (3)	−0.001 (2)	0.003 (2)	0.005 (2)
O2	0.025 (3)	0.037 (4)	0.010 (3)	0.002 (3)	0.004 (2)	0.004 (2)
O1	0.022 (3)	0.020 (3)	0.025 (3)	0.000 (2)	−0.002 (3)	0.007 (2)
C14	0.026 (4)	0.026 (4)	0.010 (4)	0.003 (3)	0.005 (3)	0.006 (3)
C19	0.024 (4)	0.026 (5)	0.019 (4)	0.002 (4)	0.004 (4)	0.007 (4)
C12	0.018 (4)	0.021 (4)	0.020 (4)	−0.002 (3)	0.000 (3)	0.007 (3)
C5	0.030 (5)	0.027 (5)	0.016 (4)	0.009 (4)	0.004 (4)	0.000 (3)
C20	0.021 (4)	0.016 (4)	0.016 (4)	0.002 (3)	0.003 (3)	0.002 (3)
C13	0.024 (4)	0.023 (4)	0.013 (4)	0.002 (3)	0.004 (3)	0.009 (3)
C22	0.021 (4)	0.024 (5)	0.030 (5)	0.008 (3)	0.010 (4)	0.007 (4)
C10	0.021 (4)	0.025 (5)	0.024 (5)	0.002 (3)	0.004 (4)	0.002 (4)
C25	0.027 (4)	0.009 (4)	0.027 (5)	0.001 (3)	−0.002 (4)	0.000 (3)
C21	0.028 (4)	0.029 (5)	0.016 (4)	0.005 (4)	0.006 (4)	0.007 (4)
C3	0.020 (4)	0.032 (5)	0.022 (5)	−0.002 (4)	0.001 (4)	0.006 (4)
C7	0.020 (4)	0.020 (4)	0.034 (5)	−0.001 (3)	−0.002 (4)	0.011 (4)
C11	0.018 (4)	0.023 (5)	0.027 (5)	0.000 (3)	0.000 (4)	0.006 (4)
C6	0.023 (4)	0.033 (5)	0.028 (5)	−0.004 (4)	0.002 (4)	0.011 (4)
C24	0.029 (4)	0.021 (4)	0.009 (4)	0.006 (3)	0.002 (3)	0.001 (3)
C23	0.021 (4)	0.019 (4)	0.042 (6)	0.005 (3)	−0.001 (4)	0.008 (4)
C18	0.020 (4)	0.041 (5)	0.016 (4)	0.002 (4)	0.001 (3)	0.005 (4)
C8	0.022 (4)	0.023 (5)	0.051 (6)	0.001 (4)	−0.005 (4)	0.015 (4)
C2	0.020 (4)	0.029 (5)	0.018 (4)	0.001 (3)	0.001 (3)	0.001 (4)
C26	0.030 (4)	0.013 (4)	0.017 (4)	0.003 (3)	0.004 (4)	0.004 (3)
C27	0.032 (5)	0.012 (4)	0.059 (7)	0.000 (4)	0.003 (5)	0.005 (4)
C9	0.025 (4)	0.020 (5)	0.035 (5)	0.001 (4)	0.005 (4)	0.008 (4)
C15	0.025 (4)	0.033 (5)	0.026 (5)	−0.001 (4)	0.000 (4)	0.004 (4)
C16	0.035 (5)	0.030 (5)	0.028 (5)	0.003 (4)	0.004 (4)	−0.011 (4)
C17	0.029 (5)	0.047 (6)	0.026 (5)	0.008 (4)	0.002 (4)	−0.016 (4)
N1	0.024 (4)	0.019 (4)	0.054 (5)	−0.001 (3)	0.001 (4)	0.008 (4)
C28	0.028 (5)	0.029 (5)	0.052 (7)	0.001 (4)	0.010 (5)	0.000 (5)
C4	0.033 (5)	0.036 (5)	0.027 (5)	0.013 (4)	−0.002 (4)	0.000 (4)
C1	0.021 (4)	0.052 (6)	0.018 (5)	0.006 (4)	0.000 (4)	0.006 (4)
C32	0.038 (6)	0.061 (7)	0.039 (6)	0.001 (5)	0.000 (5)	0.005 (5)
C30	0.031 (5)	0.026 (5)	0.090 (10)	−0.001 (4)	−0.005 (6)	0.022 (6)
C31	0.033 (6)	0.112 (11)	0.026 (6)	0.012 (6)	−0.007 (5)	−0.024 (6)
C29	0.027 (5)	0.023 (5)	0.045 (6)	0.010 (4)	0.012 (4)	0.007 (4)
N2	0.029 (5)	0.059 (6)	0.073 (7)	0.018 (4)	−0.014 (5)	−0.047 (5)
C33A	0.042 (14)	0.014 (14)	0.024 (14)	−0.007 (12)	0.004 (10)	0.004 (12)
C34A	0.074 (16)	0.008 (10)	0.031 (12)	0.011 (9)	0.026 (11)	−0.001 (8)
C33B	0.075 (15)	0.031 (13)	0.025 (11)	−0.022 (11)	−0.020 (11)	0.013 (9)
C34B	0.053 (17)	0.04 (2)	0.048 (16)	0.001 (15)	0.010 (13)	0.035 (18)

Geometric parameters (Å, º)

Ni1—S5	2.149 (2)	C7—C8	1.391 (12)
Ni1—S5^i	2.149 (2)	C11—H11	0.9500
Ni1—S4	2.158 (2)	C24—C23	1.402 (12)
Ni1—S4^i	2.158 (2)	C24—H24	0.9500
Ni2—S9^ii	2.154 (2)	C23—H23	0.9500
Ni2—S9	2.154 (2)	C18—C17	1.405 (13)
Ni2—S10	2.156 (2)	C18—H18	0.9500
Ni2—S10^ii	2.156 (2)	C8—C9	1.389 (12)
S5—C3	1.713 (9)	C8—H8	0.9500
S8—C4	1.712 (9)	C27—N1	1.458 (11)
S8—C6	1.744 (9)	C27—C28	1.527 (15)
S8—S3	3.501 (3)	C27—H27A	0.9900
S10—C6	1.705 (10)	C27—H27B	0.9900
S4—C2	1.713 (9)	C9—N1	1.354 (11)
S9—C5	1.720 (9)	C15—C16	1.352 (12)
S3—C1	1.733 (10)	C15—H15	0.9500
S3—C3	1.737 (9)	C16—C17	1.425 (13)
S3—S6	3.689 (4)	C16—H16	0.9500
S2—C1	1.722 (10)	C17—N2	1.345 (12)
S2—C2	1.740 (9)	N1—C29	1.462 (11)
S7—C4	1.733 (9)	C28—H28A	0.9800
S7—C5	1.745 (9)	C28—H28B	0.9800
S6—C4	1.653 (10)	C28—H28C	0.9800
S1—C1	1.635 (10)	C32—C31	1.515 (15)
S1—S9^iii	3.537 (4)	C32—H32A	0.9800
O3—C26	1.223 (9)	C32—H32B	0.9800
O2—C26	1.310 (9)	C32—H32C	0.9800
O2—H2	0.8400	C30—C29	1.488 (14)
O1—C7	1.350 (10)	C30—H30A	0.9800
O1—C19	1.353 (10)	C30—H30B	0.9800
C14—C19	1.395 (11)	C30—H30C	0.9800
C14—C15	1.403 (12)	C31—N2	1.429 (14)
C14—C13	1.410 (11)	C31—H31A	0.9900
C19—C18	1.374 (12)	C31—H31B	0.9900
C12—C13	1.370 (11)	C29—H29A	0.9900
C12—C7	1.399 (11)	C29—H29B	0.9900
C12—C11	1.433 (11)	N2—C33B	1.452 (16)
C5—C6	1.347 (12)	N2—C33A	1.69 (3)
C20—C21	1.390 (11)	C33A—C34A	1.48 (4)
C20—C25	1.394 (11)	C33A—H33A	0.9900
C20—C13	1.498 (11)	C33A—H33B	0.9900
C22—C23	1.362 (12)	C34A—H34A	0.9800
C22—C21	1.383 (11)	C34A—H34B	0.9800
C22—H22	0.9500	C34A—H34C	0.9800
C10—C11	1.349 (12)	C33B—C34B	1.54 (3)
C10—C9	1.423 (11)	C33B—H33C	0.9900
C10—H10	0.9500	C33B—H33D	0.9900
C25—C24	1.380 (11)	C34B—H34D	0.9800
C25—C26	1.484 (12)	C34B—H34E	0.9800
C21—H21	0.9500	C34B—H34F	0.9800
C3—C2	1.352 (12)
S5—Ni1—S5^i	180.0	C3—C2—S2	116.0 (7)
S5—Ni1—S4	93.96 (9)	S4—C2—S2	122.4 (5)
S5^i—Ni1—S4	86.04 (9)	O3—C26—O2	123.2 (8)
S5—Ni1—S4^i	86.04 (9)	O3—C26—C25	122.9 (7)
S5^i—Ni1—S4^i	93.96 (9)	O2—C26—C25	113.8 (7)
S4—Ni1—S4^i	180.00 (11)	N1—C27—C28	111.6 (8)
S9^ii—Ni2—S9	180.0	N1—C27—H27A	109.3
S9^ii—Ni2—S10	86.45 (8)	C28—C27—H27A	109.3
S9—Ni2—S10	93.55 (8)	N1—C27—H27B	109.3
S9^ii—Ni2—S10^ii	93.55 (8)	C28—C27—H27B	109.3
S9—Ni2—S10^ii	86.45 (8)	H27A—C27—H27B	108.0
S10—Ni2—S10^ii	180.0	N1—C9—C8	121.2 (8)
C3—S5—Ni1	101.5 (3)	N1—C9—C10	120.1 (8)
C4—S8—C6	97.7 (4)	C8—C9—C10	118.7 (8)
C4—S8—S3	93.7 (3)	C16—C15—C14	121.2 (8)
C6—S8—S3	150.8 (3)	C16—C15—H15	119.4
C6—S10—Ni2	101.7 (3)	C14—C15—H15	119.4
C2—S4—Ni1	101.3 (3)	C15—C16—C17	122.0 (9)
C5—S9—Ni2	101.5 (3)	C15—C16—H16	119.0
C1—S3—C3	96.9 (4)	C17—C16—H16	119.0
C1—S3—S8	73.6 (3)	N2—C17—C18	120.5 (9)
C3—S3—S8	83.7 (3)	N2—C17—C16	122.5 (9)
C1—S3—S6	122.1 (3)	C18—C17—C16	117.0 (8)
C3—S3—S6	81.7 (3)	C9—N1—C27	122.9 (7)
S8—S3—S6	48.57 (7)	C9—N1—C29	121.5 (7)
C1—S2—C2	97.2 (4)	C27—N1—C29	115.6 (7)
C4—S7—C5	96.8 (4)	C27—C28—H28A	109.5
C4—S6—S3	88.2 (3)	C27—C28—H28B	109.5
C1—S1—S9^iii	138.2 (3)	H28A—C28—H28B	109.5
C26—O2—H2	109.5	C27—C28—H28C	109.5
C7—O1—C19	120.2 (6)	H28A—C28—H28C	109.5
C19—C14—C15	116.9 (8)	H28B—C28—H28C	109.5
C19—C14—C13	118.4 (7)	S6—C4—S8	123.3 (5)
C15—C14—C13	124.6 (7)	S6—C4—S7	123.3 (5)
O1—C19—C18	115.4 (7)	S8—C4—S7	113.3 (5)
O1—C19—C14	121.5 (7)	S1—C1—S2	123.6 (6)
C18—C19—C14	123.0 (8)	S1—C1—S3	122.9 (6)
C13—C12—C7	120.3 (7)	S2—C1—S3	113.4 (5)
C13—C12—C11	124.7 (7)	C31—C32—H32A	109.5
C7—C12—C11	114.9 (7)	C31—C32—H32B	109.5
C6—C5—S9	121.3 (7)	H32A—C32—H32B	109.5
C6—C5—S7	116.4 (7)	C31—C32—H32C	109.5
S9—C5—S7	122.2 (5)	H32A—C32—H32C	109.5
C21—C20—C25	118.4 (7)	H32B—C32—H32C	109.5
C21—C20—C13	118.8 (7)	C29—C30—H30A	109.5
C25—C20—C13	122.5 (7)	C29—C30—H30B	109.5
C12—C13—C14	119.0 (7)	H30A—C30—H30B	109.5
C12—C13—C20	120.9 (7)	C29—C30—H30C	109.5
C14—C13—C20	119.8 (7)	H30A—C30—H30C	109.5
C23—C22—C21	120.9 (8)	H30B—C30—H30C	109.5
C23—C22—H22	119.6	N2—C31—C32	114.0 (11)
C21—C22—H22	119.6	N2—C31—H31A	108.8
C11—C10—C9	120.8 (8)	C32—C31—H31A	108.8
C11—C10—H10	119.6	N2—C31—H31B	108.8
C9—C10—H10	119.6	C32—C31—H31B	108.8
C24—C25—C20	120.9 (8)	H31A—C31—H31B	107.6
C24—C25—C26	118.3 (7)	N1—C29—C30	114.6 (8)
C20—C25—C26	120.6 (7)	N1—C29—H29A	108.6
C22—C21—C20	120.5 (8)	C30—C29—H29A	108.6
C22—C21—H21	119.7	N1—C29—H29B	108.6
C20—C21—H21	119.7	C30—C29—H29B	108.6
C2—C3—S5	121.6 (7)	H29A—C29—H29B	107.6
C2—C3—S3	116.4 (7)	C17—N2—C31	123.4 (10)
S5—C3—S3	122.0 (5)	C17—N2—C33B	122.3 (11)
O1—C7—C8	115.8 (7)	C31—N2—C33B	111.1 (11)
O1—C7—C12	120.4 (7)	C17—N2—C33A	115.8 (14)
C8—C7—C12	123.7 (8)	C31—N2—C33A	116.9 (14)
C10—C11—C12	122.4 (7)	C33B—N2—C33A	40.0 (15)
C10—C11—H11	118.8	C34A—C33A—N2	106.8 (18)
C12—C11—H11	118.8	C34A—C33A—H33A	110.4
C5—C6—S10	121.8 (7)	N2—C33A—H33A	110.4
C5—C6—S8	115.6 (7)	C34A—C33A—H33B	110.4
S10—C6—S8	122.5 (5)	N2—C33A—H33B	110.4
C25—C24—C23	119.6 (7)	H33A—C33A—H33B	108.6
C25—C24—H24	120.2	N2—C33B—C34B	96.8 (18)
C23—C24—H24	120.2	N2—C33B—H33C	112.4
C22—C23—C24	119.6 (7)	C34B—C33B—H33C	112.4
C22—C23—H23	120.2	N2—C33B—H33D	112.4
C24—C23—H23	120.2	C34B—C33B—H33D	112.4
C19—C18—C17	119.8 (8)	H33C—C33B—H33D	110.0
C19—C18—H18	120.1	C33B—C34B—H34D	109.5
C17—C18—H18	120.1	C33B—C34B—H34E	109.5
C9—C8—C7	119.2 (7)	H34D—C34B—H34E	109.5
C9—C8—H8	120.4	C33B—C34B—H34F	109.5
C7—C8—H8	120.4	H34D—C34B—H34F	109.5
C3—C2—S4	121.6 (7)	H34E—C34B—H34F	109.5

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3^iv	0.84	1.85	2.662 (8)	163

Symmetry code: (iv) −x+2, −y, −z+1.