Bis[1,2-bis­(4-tert-butyl­phen­yl)ethyl­ene-1,2-di­thiol­ato(1−)]nickel(II) pentane 0.25-solvate

Das Gupta, T.; Applebaum, J.; Broussard, W.; Mack, C.; Wu, C.; Mague, J.T.; Donahue, J.P.

doi:10.1107/S205698902300097X

Bis[1,2-bis(4-tert-butylphenyl)ethylene-1,2-dithiolato(1−)]nickel(II) pentane 0.25-solvate

T. Das Gupta, J. Applebaum, W. Broussard, C. Mack, C. Wu, J. T. Mague and J. P. Donahue

Square-planar bis[1,2-bis(4-tert-butylphenyl)ethylene-1,2-dithiolato(1–)]nickel(II) crystallizes on a general position in chiral P4₁2₁2, where asymmetry is induced by twisting of the aryl rings due to intermolecular ^tBu-C—H

ring_centroid interactions in the packing pattern.

Keywords: crystal structure; dithiolene; nickel; electron-withdrawing; electron-donating.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205698902300097X/jy2027sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S205698902300097X/jy2027Isup2.hkl Contains datablock I
	Text file https://doi.org/10.1107/S205698902300097X/jy2027sup3.txt Supplementary material

CCDC reference: 2239611

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R factor = 0.045
wR factor = 0.138
Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          3 Report
              C42B      C43B      C44B

Author Response: Disorder in C42 C43 C44 modeled with isotropic refinement.


Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given (or Incomplete) ........     Please Check
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.94 Report
PLAT213_ALERT_2_C Atom C14A            has ADP max/min Ratio .....        3.2 prolat
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        4.3 Ratio
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        5.1 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C11 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C31 Check
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00615 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          4 Check
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  2.11Ang From C47             1.55 eA-3

Alert level G
CHEMS02_ALERT_1_G  Please check that you have entered the correct
            _publ_requested_category classification of your compound;
            FI or CI or EI for inorganic; FM or CM or EM for metal-organic;
            FO or CO or EO for organic.
            From the CIF: _publ_requested_category   FI
            From the CIF: _chemical_formula_sum :C45.25 H55 Ni1 S4
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          7 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         12 Report
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...      0.250 Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       5.79 Why ?
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          3 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          6 Report
PLAT300_ALERT_4_G Atom Site Occupancy of C45        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C46        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C47        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H46A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H46B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H47A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H47B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H47C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H45A       Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H45B       Constrained at       0.25 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        12% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       4.25 Check
PLAT412_ALERT_2_G Short Intra XH3 .. XHn     H9       ..H13B     .       2.03 Ang.
                                                      x,y,z  =      1_555 Check
PLAT412_ALERT_2_G Short Intra XH3 .. XHn     H37      ..H42C     .       2.04 Ang.
                                                      x,y,z  =      1_555 Check
PLAT412_ALERT_2_G Short Intra XH3 .. XHn     H39      ..H43A     .       2.08 Ang.
                                                      x,y,z  =      1_555 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  C45      ..C46      .       1.61 Ang.
                                                -y,-x,3/2-z  =      8_556 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  C45      ..C47      .       2.64 Ang.
                                                -y,-x,3/2-z  =      8_556 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  C46      ..C46      .       2.94 Ang.
                                                -y,-x,3/2-z  =      8_556 Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C5 H12
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1       (III)     .       3.21 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          6 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         27 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          1 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          5 Note
PLAT965_ALERT_2_G The SHELXL WEIGHT Optimisation has not Converged     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  19 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
  17 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX4 (Bruker, 2021); cell refinement: SAINT (Bruker, 2021); data reduction: SAINT (Bruker, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Bis[1,2-bis(4-tert-butylphenyl)ethylene-1,2-dithiolato(1-)]nickel(II) pentane 0.25-solvate top

Crystal data top

[Ni(C₂₂H₂₆S₂)₂]·0.25C₅H₁₂	D_x = 1.169 Mg m⁻³
M_r = 785.84	Cu Kα radiation, λ = 1.54178 Å
Tetragonal, P4₁2₁2	Cell parameters from 9381 reflections
a = 11.7187 (4) Å	θ = 4.0–72.6°
c = 65.014 (4) Å	µ = 2.58 mm⁻¹
V = 8928.2 (8) Å³	T = 150 K
Z = 8	Column, black
F(000) = 3348	0.21 × 0.11 × 0.05 mm

Data collection top

Bruker D8 VENTURE PHOTON 3 CPAD diffractometer	8886 independent reflections
Radiation source: INCOATEC IµS micro—-focus source	8592 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.072
Detector resolution: 7.3910 pixels mm^-1	θ_max = 72.7°, θ_min = 4.0°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −14→14
T_min = 0.77, T_max = 0.88	l = −80→80
203444 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.0951P)² + 5.7915P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.003
8886 reflections	Δρ_max = 1.57 e Å⁻³
497 parameters	Δρ_min = −0.40 e Å⁻³
27 restraints	Absolute structure: Refined as an inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.03 (2)

Special details top

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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.11325 (6)	0.50471 (6)	0.66096 (2)	0.02572 (18)
S1	0.16585 (8)	0.54152 (9)	0.63052 (2)	0.0270 (2)
S2	0.26404 (8)	0.40913 (9)	0.66631 (2)	0.0284 (2)
S3	−0.03961 (8)	0.59838 (8)	0.65575 (2)	0.0264 (2)
S4	0.06448 (9)	0.46883 (9)	0.69166 (2)	0.0318 (2)
C1	0.2970 (3)	0.4783 (3)	0.62760 (6)	0.0252 (7)
C2	0.3415 (3)	0.4174 (3)	0.64413 (6)	0.0253 (7)
C3	−0.1135 (3)	0.5915 (3)	0.67829 (6)	0.0269 (8)
C4	−0.0659 (3)	0.5317 (3)	0.69492 (6)	0.0295 (8)
C5	0.3489 (3)	0.4871 (3)	0.60685 (6)	0.0244 (7)
C6	0.3989 (3)	0.3928 (4)	0.59745 (6)	0.0277 (8)
H6	0.408370	0.323934	0.604960	0.033*
C7	0.4348 (3)	0.3990 (4)	0.57716 (6)	0.0300 (8)
H7	0.467590	0.333322	0.570971	0.036*
C8	0.4244 (3)	0.4987 (4)	0.56554 (6)	0.0303 (8)
C9	0.3773 (4)	0.5935 (4)	0.57528 (6)	0.0308 (8)
H9	0.370156	0.662995	0.567872	0.037*
C10	0.3406 (3)	0.5888 (4)	0.59557 (6)	0.0271 (8)
H10	0.309538	0.655085	0.601869	0.032*
C11	0.4587 (4)	0.5019 (5)	0.54280 (7)	0.0394 (10)
C12A	0.3892 (19)	0.4182 (18)	0.5312 (2)	0.074 (7)	0.461 (19)
H12A	0.421610	0.407950	0.517424	0.111*	0.461 (19)
H12B	0.310697	0.446374	0.530004	0.111*	0.461 (19)
H12C	0.389198	0.344980	0.538470	0.111*	0.461 (19)
C13A	0.4460 (16)	0.6250 (14)	0.53373 (19)	0.058 (4)	0.461 (19)
H13A	0.487709	0.629958	0.520695	0.087*	0.461 (19)
H13B	0.477300	0.680560	0.543481	0.087*	0.461 (19)
H13C	0.365115	0.641493	0.531339	0.087*	0.461 (19)
C14A	0.5838 (13)	0.4692 (18)	0.54094 (19)	0.068 (6)	0.461 (19)
H14A	0.593129	0.414042	0.529742	0.102*	0.461 (19)
H14B	0.609666	0.435055	0.553881	0.102*	0.461 (19)
H14C	0.629133	0.537554	0.537998	0.102*	0.461 (19)
C12B	0.3464 (13)	0.500 (2)	0.5301 (2)	0.086 (6)	0.539 (19)
H12D	0.311742	0.576312	0.530291	0.129*	0.539 (19)
H12E	0.293295	0.444965	0.536151	0.129*	0.539 (19)
H12F	0.363294	0.478302	0.515887	0.129*	0.539 (19)
C13B	0.530 (2)	0.6003 (19)	0.5382 (2)	0.106 (10)	0.539 (19)
H13D	0.492102	0.669788	0.543104	0.158*	0.539 (19)
H13E	0.541539	0.605513	0.523298	0.158*	0.539 (19)
H13F	0.603756	0.591920	0.545073	0.158*	0.539 (19)
C14B	0.510 (2)	0.3851 (15)	0.5356 (2)	0.097 (8)	0.539 (19)
H14D	0.536602	0.391757	0.521379	0.146*	0.539 (19)
H14E	0.451461	0.325667	0.536495	0.146*	0.539 (19)
H14F	0.574518	0.364714	0.544519	0.146*	0.539 (19)
C15	0.4557 (3)	0.3629 (3)	0.64462 (6)	0.0247 (7)
C16	0.4669 (3)	0.2503 (3)	0.65136 (6)	0.0257 (7)
H16	0.400958	0.207967	0.655083	0.031*
C17	0.5738 (3)	0.1998 (3)	0.65265 (6)	0.0267 (7)
H17	0.579397	0.122266	0.656774	0.032*
C18	0.6728 (3)	0.2598 (3)	0.64807 (6)	0.0254 (7)
C19	0.6602 (3)	0.3733 (4)	0.64133 (7)	0.0329 (9)
H19	0.726089	0.416447	0.637899	0.039*
C20	0.5537 (3)	0.4231 (4)	0.63961 (7)	0.0331 (9)
H20	0.547600	0.499669	0.634928	0.040*
C21	0.7914 (3)	0.2093 (3)	0.65087 (6)	0.0289 (8)
C22	0.8510 (4)	0.2736 (4)	0.66836 (8)	0.0411 (10)
H22A	0.856736	0.354653	0.664813	0.062*
H22B	0.927732	0.242173	0.670390	0.062*
H22C	0.806794	0.265018	0.681056	0.062*
C23	0.7887 (4)	0.0820 (4)	0.65608 (8)	0.0383 (10)
H23A	0.753235	0.071129	0.669589	0.057*
H23B	0.866802	0.052053	0.656359	0.057*
H23C	0.744385	0.041142	0.645628	0.057*
C24	0.8616 (4)	0.2242 (5)	0.63087 (9)	0.0492 (13)
H24A	0.816219	0.198526	0.619089	0.074*
H24B	0.931582	0.178616	0.631763	0.074*
H24C	0.881503	0.304810	0.629110	0.074*
C25	−0.2282 (3)	0.6431 (3)	0.67841 (6)	0.0267 (8)
C26	−0.3229 (4)	0.5781 (4)	0.68385 (9)	0.0425 (11)
H26	−0.313031	0.501166	0.688097	0.051*
C27	−0.4317 (4)	0.6248 (4)	0.68311 (9)	0.0453 (12)
H27	−0.495056	0.578704	0.686895	0.054*
C28	−0.4510 (3)	0.7372 (4)	0.67700 (6)	0.0291 (8)
C29	−0.3557 (4)	0.8014 (4)	0.67168 (7)	0.0319 (8)
H29	−0.365326	0.878569	0.667577	0.038*
C30	−0.2463 (4)	0.7548 (4)	0.67226 (7)	0.0319 (9)
H30	−0.182968	0.800535	0.668360	0.038*
C31	−0.5721 (4)	0.7830 (4)	0.67471 (7)	0.0347 (9)
C32	−0.5777 (5)	0.9115 (5)	0.67685 (13)	0.0668 (19)
H32A	−0.542830	0.934267	0.689922	0.100*
H32B	−0.657541	0.936162	0.676570	0.100*
H32C	−0.536216	0.947115	0.665444	0.100*
C33	−0.6538 (5)	0.7297 (6)	0.69042 (11)	0.0655 (18)
H33A	−0.620952	0.736244	0.704226	0.098*
H33B	−0.665624	0.649050	0.687078	0.098*
H33C	−0.727136	0.769902	0.689986	0.098*
C34	−0.6154 (5)	0.7513 (6)	0.65312 (9)	0.0584 (15)
H34A	−0.698181	0.762907	0.652457	0.088*
H34B	−0.597801	0.671104	0.650284	0.088*
H34C	−0.577955	0.799788	0.642861	0.088*
C35	−0.1179 (4)	0.5215 (4)	0.71562 (6)	0.0331 (8)
C36	−0.1179 (5)	0.4183 (4)	0.72576 (7)	0.0448 (11)
H36	−0.088892	0.352356	0.719052	0.054*
C37	−0.1602 (5)	0.4093 (5)	0.74586 (7)	0.0480 (12)
H37	−0.159235	0.337265	0.752549	0.058*
C38	−0.2035 (5)	0.5031 (5)	0.75617 (7)	0.0464 (12)
C39	−0.2077 (6)	0.6049 (5)	0.74547 (8)	0.0572 (15)
H39	−0.239496	0.669983	0.752028	0.069*
C40	−0.1672 (5)	0.6156 (4)	0.72546 (8)	0.0494 (13)
H40	−0.173016	0.686603	0.718481	0.059*
C41	−0.2483 (5)	0.4953 (5)	0.77823 (7)	0.0585 (16)
C42A	−0.1891 (16)	0.3937 (11)	0.78986 (19)	0.051 (4)*	0.48 (3)
H42A	−0.218619	0.389213	0.803941	0.077*	0.48 (3)
H42B	−0.106439	0.406361	0.790249	0.077*	0.48 (3)
H42C	−0.205229	0.322032	0.782647	0.077*	0.48 (3)
C43A	−0.227 (2)	0.6045 (12)	0.7902 (2)	0.059 (4)*	0.48 (3)
H43A	−0.267924	0.667602	0.783673	0.089*	0.48 (3)
H43B	−0.144626	0.621226	0.790162	0.089*	0.48 (3)
H43C	−0.253082	0.595077	0.804358	0.089*	0.48 (3)
C44A	−0.3728 (12)	0.465 (3)	0.7777 (3)	0.083 (6)*	0.48 (3)
H44A	−0.402360	0.461900	0.791837	0.124*	0.48 (3)
H44B	−0.382656	0.390692	0.771135	0.124*	0.48 (3)
H44C	−0.414595	0.523307	0.769961	0.124*	0.48 (3)
C42B	−0.2387 (19)	0.3819 (9)	0.7882 (2)	0.061 (4)*	0.52 (3)
H42D	−0.284956	0.326412	0.780606	0.092*	0.52 (3)
H42E	−0.266099	0.386955	0.802407	0.092*	0.52 (3)
H42F	−0.158737	0.357487	0.788152	0.092*	0.52 (3)
C43B	−0.1921 (14)	0.5929 (10)	0.79087 (17)	0.044 (3)*	0.52 (3)
H43D	−0.210581	0.583221	0.805470	0.066*	0.52 (3)
H43E	−0.221200	0.666640	0.786075	0.066*	0.52 (3)
H43F	−0.109150	0.590326	0.789038	0.066*	0.52 (3)
C44B	−0.3796 (9)	0.5117 (18)	0.7777 (2)	0.064 (4)*	0.52 (3)
H44D	−0.414406	0.449483	0.769802	0.096*	0.52 (3)
H44E	−0.397658	0.584817	0.771121	0.096*	0.52 (3)
H44F	−0.409572	0.511207	0.791743	0.096*	0.52 (3)
C45	−0.6695 (19)	0.6695 (19)	0.750000	0.104 (9)*	0.5
H45A	−0.625613	0.640961	0.738040	0.125*	0.25
H45B	−0.640954	0.625607	0.761958	0.125*	0.25
C46	−0.621 (2)	0.796 (2)	0.7537 (4)	0.126 (8)*	0.5
H46A	−0.665818	0.849448	0.745177	0.152*	0.5
H46B	−0.633358	0.816350	0.768245	0.152*	0.5
C47	−0.497 (2)	0.814 (2)	0.7489 (4)	0.138 (9)*	0.5
H47A	−0.476819	0.893635	0.751644	0.208*	0.5
H47B	−0.450667	0.763562	0.757474	0.208*	0.5
H47C	−0.483233	0.796770	0.734331	0.208*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0209 (3)	0.0316 (4)	0.0247 (3)	0.0036 (2)	0.0032 (2)	0.0019 (3)
S1	0.0211 (4)	0.0343 (5)	0.0257 (4)	0.0055 (3)	0.0021 (3)	0.0047 (4)
S2	0.0234 (4)	0.0357 (5)	0.0263 (4)	0.0056 (4)	0.0023 (3)	0.0051 (4)
S3	0.0229 (4)	0.0314 (5)	0.0249 (4)	0.0042 (3)	0.0037 (3)	0.0034 (3)
S4	0.0290 (5)	0.0412 (5)	0.0252 (4)	0.0091 (4)	0.0026 (3)	0.0044 (4)
C1	0.0194 (16)	0.0253 (17)	0.0309 (18)	−0.0014 (14)	0.0005 (14)	−0.0002 (15)
C2	0.0218 (17)	0.0276 (18)	0.0266 (17)	−0.0019 (14)	0.0007 (14)	−0.0009 (15)
C3	0.0256 (18)	0.0277 (19)	0.0275 (18)	−0.0003 (15)	0.0060 (15)	−0.0006 (15)
C4	0.0286 (18)	0.0312 (19)	0.0287 (18)	0.0025 (16)	0.0030 (15)	0.0009 (15)
C5	0.0164 (15)	0.0282 (19)	0.0286 (17)	−0.0003 (13)	−0.0017 (13)	0.0029 (15)
C6	0.0214 (17)	0.0296 (19)	0.0320 (19)	0.0018 (15)	0.0000 (15)	0.0013 (15)
C7	0.0244 (18)	0.034 (2)	0.032 (2)	0.0011 (15)	0.0011 (15)	−0.0030 (16)
C8	0.0217 (18)	0.042 (2)	0.0275 (19)	−0.0056 (16)	0.0012 (15)	−0.0005 (17)
C9	0.0264 (19)	0.035 (2)	0.031 (2)	−0.0045 (16)	−0.0010 (15)	0.0049 (16)
C10	0.0215 (17)	0.0301 (19)	0.0295 (19)	−0.0002 (15)	−0.0007 (14)	0.0033 (16)
C11	0.041 (2)	0.052 (3)	0.0252 (19)	−0.005 (2)	0.0031 (18)	−0.0001 (19)
C12A	0.095 (15)	0.097 (14)	0.029 (6)	−0.052 (12)	0.006 (7)	−0.005 (7)
C13A	0.072 (10)	0.074 (9)	0.028 (5)	0.007 (8)	0.012 (6)	0.019 (5)
C14A	0.061 (8)	0.111 (15)	0.032 (6)	0.024 (9)	0.031 (6)	0.017 (7)
C12B	0.064 (8)	0.16 (2)	0.037 (6)	0.010 (10)	−0.011 (5)	−0.001 (9)
C13B	0.133 (19)	0.132 (17)	0.052 (8)	−0.075 (16)	0.049 (11)	−0.023 (9)
C14B	0.16 (2)	0.083 (11)	0.052 (7)	0.056 (13)	0.039 (10)	−0.007 (7)
C15	0.0208 (17)	0.0276 (18)	0.0257 (17)	0.0022 (14)	−0.0011 (14)	0.0024 (14)
C16	0.0232 (17)	0.0265 (18)	0.0274 (17)	−0.0030 (14)	−0.0003 (14)	−0.0008 (15)
C17	0.0266 (18)	0.0231 (17)	0.0304 (18)	−0.0003 (14)	−0.0009 (15)	0.0011 (15)
C18	0.0214 (17)	0.0282 (19)	0.0266 (17)	0.0034 (15)	−0.0009 (14)	0.0000 (14)
C19	0.0205 (18)	0.031 (2)	0.048 (2)	0.0012 (15)	0.0031 (17)	0.0103 (18)
C20	0.0236 (19)	0.0287 (19)	0.047 (2)	0.0016 (16)	0.0011 (17)	0.0137 (18)
C21	0.0240 (18)	0.030 (2)	0.033 (2)	0.0049 (15)	0.0013 (15)	0.0011 (16)
C22	0.026 (2)	0.042 (2)	0.055 (3)	0.0059 (18)	−0.0105 (19)	−0.004 (2)
C23	0.030 (2)	0.030 (2)	0.055 (3)	0.0086 (17)	−0.0027 (19)	0.0017 (19)
C24	0.035 (2)	0.060 (3)	0.053 (3)	0.017 (2)	0.017 (2)	0.011 (2)
C25	0.0255 (19)	0.0282 (19)	0.0264 (17)	0.0009 (15)	0.0043 (14)	−0.0009 (15)
C26	0.030 (2)	0.032 (2)	0.066 (3)	0.0067 (18)	0.016 (2)	0.013 (2)
C27	0.028 (2)	0.030 (2)	0.078 (4)	0.0019 (17)	0.019 (2)	0.013 (2)
C28	0.0240 (18)	0.030 (2)	0.0337 (19)	0.0036 (15)	0.0044 (15)	−0.0020 (16)
C29	0.027 (2)	0.0261 (19)	0.042 (2)	0.0004 (15)	0.0012 (17)	0.0051 (17)
C30	0.027 (2)	0.030 (2)	0.039 (2)	−0.0010 (16)	0.0019 (16)	0.0042 (17)
C31	0.029 (2)	0.031 (2)	0.045 (2)	0.0054 (16)	0.0057 (17)	0.0025 (17)
C32	0.034 (3)	0.034 (3)	0.133 (6)	0.013 (2)	−0.009 (3)	−0.015 (3)
C33	0.033 (3)	0.078 (4)	0.086 (4)	0.019 (3)	0.025 (3)	0.022 (4)
C34	0.036 (3)	0.077 (4)	0.062 (3)	0.023 (3)	−0.009 (2)	−0.018 (3)
C35	0.032 (2)	0.039 (2)	0.0279 (19)	0.0029 (17)	0.0062 (16)	0.0016 (16)
C36	0.062 (3)	0.039 (2)	0.034 (2)	0.009 (2)	0.014 (2)	0.0048 (19)
C37	0.070 (4)	0.042 (3)	0.031 (2)	0.003 (2)	0.013 (2)	0.007 (2)
C38	0.063 (3)	0.047 (3)	0.029 (2)	−0.006 (2)	0.013 (2)	0.000 (2)
C39	0.085 (4)	0.046 (3)	0.041 (3)	0.006 (3)	0.024 (3)	−0.008 (2)
C40	0.075 (4)	0.038 (2)	0.036 (2)	0.008 (2)	0.019 (2)	0.006 (2)
C41	0.087 (4)	0.056 (3)	0.032 (2)	−0.011 (3)	0.023 (3)	−0.002 (2)

Geometric parameters (Å, º) top

Ni1—S1	2.1174 (11)	C24—H24B	0.9800
Ni1—S4	2.1185 (11)	C24—H24C	0.9800
Ni1—S2	2.1207 (11)	C25—C30	1.386 (6)
Ni1—S3	2.1281 (11)	C25—C26	1.392 (6)
S1—C1	1.716 (4)	C26—C27	1.389 (6)
S2—C2	1.707 (4)	C26—H26	0.9500
S3—C3	1.704 (4)	C27—C28	1.394 (6)
S4—C4	1.710 (4)	C27—H27	0.9500
C1—C2	1.392 (5)	C28—C29	1.390 (6)
C1—C5	1.484 (5)	C28—C31	1.525 (6)
C2—C15	1.483 (5)	C29—C30	1.394 (6)
C3—C4	1.404 (6)	C29—H29	0.9500
C3—C25	1.473 (5)	C30—H30	0.9500
C4—C35	1.482 (5)	C31—C32	1.513 (7)
C5—C6	1.392 (6)	C31—C33	1.533 (7)
C5—C10	1.402 (5)	C31—C34	1.538 (7)
C6—C7	1.386 (6)	C32—H32A	0.9800
C6—H6	0.9500	C32—H32B	0.9800
C7—C8	1.396 (6)	C32—H32C	0.9800
C7—H7	0.9500	C33—H33A	0.9800
C8—C9	1.393 (6)	C33—H33B	0.9800
C8—C11	1.532 (5)	C33—H33C	0.9800
C9—C10	1.389 (6)	C34—H34A	0.9800
C9—H9	0.9500	C34—H34B	0.9800
C10—H10	0.9500	C34—H34C	0.9800
C11—C13B	1.455 (16)	C35—C36	1.378 (7)
C11—C12A	1.481 (15)	C35—C40	1.400 (7)
C11—C14A	1.520 (14)	C36—C37	1.402 (6)
C11—C12B	1.553 (14)	C36—H36	0.9500
C11—C13A	1.566 (15)	C37—C38	1.384 (8)
C11—C14B	1.567 (14)	C37—H37	0.9500
C12A—H12A	0.9800	C38—C39	1.382 (8)
C12A—H12B	0.9800	C38—C41	1.530 (6)
C12A—H12C	0.9800	C39—C40	1.391 (7)
C13A—H13A	0.9800	C39—H39	0.9500
C13A—H13B	0.9800	C40—H40	0.9500
C13A—H13C	0.9800	C41—C42B	1.482 (10)
C14A—H14A	0.9800	C41—C44A	1.501 (12)
C14A—H14B	0.9800	C41—C43A	1.518 (11)
C14A—H14C	0.9800	C41—C44B	1.551 (11)
C12B—H12D	0.9800	C41—C43B	1.554 (10)
C12B—H12E	0.9800	C41—C42A	1.572 (10)
C12B—H12F	0.9800	C42A—H42A	0.9800
C13B—H13D	0.9800	C42A—H42B	0.9800
C13B—H13E	0.9800	C42A—H42C	0.9800
C13B—H13F	0.9800	C43A—H43A	0.9800
C14B—H14D	0.9800	C43A—H43B	0.9800
C14B—H14E	0.9800	C43A—H43C	0.9800
C14B—H14F	0.9800	C44A—H44A	0.9800
C15—C20	1.387 (6)	C44A—H44B	0.9800
C15—C16	1.397 (5)	C44A—H44C	0.9800
C16—C17	1.388 (6)	C42B—H42D	0.9800
C16—H16	0.9500	C42B—H42E	0.9800
C17—C18	1.389 (6)	C42B—H42F	0.9800
C17—H17	0.9500	C43B—H43D	0.9800
C18—C19	1.409 (6)	C43B—H43E	0.9800
C18—C21	1.521 (5)	C43B—H43F	0.9800
C19—C20	1.382 (6)	C44B—H44D	0.9800
C19—H19	0.9500	C44B—H44E	0.9800
C20—H20	0.9500	C44B—H44F	0.9800
C21—C23	1.530 (6)	C45—C46ⁱ	1.61 (3)
C21—C22	1.533 (6)	C45—C46	1.61 (3)
C21—C24	1.548 (6)	C45—H45A	0.9900
C22—H22A	0.9800	C45—H45B	0.9900
C22—H22B	0.9800	C46—C47	1.49 (3)
C22—H22C	0.9800	C46—H46A	0.9900
C23—H23A	0.9800	C46—H46B	0.9900
C23—H23B	0.9800	C47—H47A	0.9800
C23—H23C	0.9800	C47—H47B	0.9800
C24—H24A	0.9800	C47—H47C	0.9800

S1—Ni1—S4	178.67 (5)	H24A—C24—H24C	109.5
S1—Ni1—S2	91.05 (4)	H24B—C24—H24C	109.5
S4—Ni1—S2	88.02 (4)	C30—C25—C26	117.9 (4)
S1—Ni1—S3	89.49 (4)	C30—C25—C3	121.7 (4)
S4—Ni1—S3	91.45 (4)	C26—C25—C3	120.3 (4)
S2—Ni1—S3	179.10 (6)	C27—C26—C25	120.6 (4)
C1—S1—Ni1	106.01 (14)	C27—C26—H26	119.7
C2—S2—Ni1	105.95 (14)	C25—C26—H26	119.7
C3—S3—Ni1	105.44 (14)	C26—C27—C28	122.1 (4)
C4—S4—Ni1	105.80 (14)	C26—C27—H27	119.0
C2—C1—C5	125.8 (3)	C28—C27—H27	119.0
C2—C1—S1	118.2 (3)	C29—C28—C27	116.9 (4)
C5—C1—S1	115.9 (3)	C29—C28—C31	122.2 (4)
C1—C2—C15	125.2 (3)	C27—C28—C31	120.7 (4)
C1—C2—S2	118.8 (3)	C28—C29—C30	121.4 (4)
C15—C2—S2	115.9 (3)	C28—C29—H29	119.3
C4—C3—C25	124.3 (4)	C30—C29—H29	119.3
C4—C3—S3	119.0 (3)	C25—C30—C29	121.3 (4)
C25—C3—S3	116.6 (3)	C25—C30—H30	119.4
C3—C4—C35	125.2 (4)	C29—C30—H30	119.4
C3—C4—S4	118.3 (3)	C32—C31—C28	112.4 (4)
C35—C4—S4	116.4 (3)	C32—C31—C33	108.5 (5)
C6—C5—C10	118.3 (4)	C28—C31—C33	111.9 (4)
C6—C5—C1	121.1 (4)	C32—C31—C34	108.0 (5)
C10—C5—C1	120.4 (4)	C28—C31—C34	108.2 (4)
C7—C6—C5	120.2 (4)	C33—C31—C34	107.7 (5)
C7—C6—H6	119.9	C31—C32—H32A	109.5
C5—C6—H6	119.9	C31—C32—H32B	109.5
C6—C7—C8	122.2 (4)	H32A—C32—H32B	109.5
C6—C7—H7	118.9	C31—C32—H32C	109.5
C8—C7—H7	118.9	H32A—C32—H32C	109.5
C9—C8—C7	117.1 (4)	H32B—C32—H32C	109.5
C9—C8—C11	121.5 (4)	C31—C33—H33A	109.5
C7—C8—C11	121.3 (4)	C31—C33—H33B	109.5
C10—C9—C8	121.6 (4)	H33A—C33—H33B	109.5
C10—C9—H9	119.2	C31—C33—H33C	109.5
C8—C9—H9	119.2	H33A—C33—H33C	109.5
C9—C10—C5	120.6 (4)	H33B—C33—H33C	109.5
C9—C10—H10	119.7	C31—C34—H34A	109.5
C5—C10—H10	119.7	C31—C34—H34B	109.5
C12A—C11—C14A	108.9 (12)	H34A—C34—H34B	109.5
C13B—C11—C8	111.6 (7)	C31—C34—H34C	109.5
C12A—C11—C8	109.3 (6)	H34A—C34—H34C	109.5
C14A—C11—C8	108.9 (6)	H34B—C34—H34C	109.5
C13B—C11—C12B	112.7 (13)	C36—C35—C40	118.2 (4)
C8—C11—C12B	106.9 (6)	C36—C35—C4	120.3 (4)
C12A—C11—C13A	111.5 (11)	C40—C35—C4	121.4 (4)
C14A—C11—C13A	107.1 (10)	C35—C36—C37	120.8 (5)
C8—C11—C13A	111.2 (6)	C35—C36—H36	119.6
C13B—C11—C14B	114.3 (12)	C37—C36—H36	119.6
C8—C11—C14B	111.5 (6)	C38—C37—C36	121.5 (5)
C12B—C11—C14B	99.0 (12)	C38—C37—H37	119.3
C11—C12A—H12A	109.5	C36—C37—H37	119.3
C11—C12A—H12B	109.5	C39—C38—C37	117.0 (4)
H12A—C12A—H12B	109.5	C39—C38—C41	120.8 (5)
C11—C12A—H12C	109.5	C37—C38—C41	122.2 (5)
H12A—C12A—H12C	109.5	C38—C39—C40	122.5 (5)
H12B—C12A—H12C	109.5	C38—C39—H39	118.8
C11—C13A—H13A	109.5	C40—C39—H39	118.8
C11—C13A—H13B	109.5	C39—C40—C35	119.8 (5)
H13A—C13A—H13B	109.5	C39—C40—H40	120.1
C11—C13A—H13C	109.5	C35—C40—H40	120.1
H13A—C13A—H13C	109.5	C44A—C41—C43A	111.8 (12)
H13B—C13A—H13C	109.5	C42B—C41—C38	115.9 (7)
C11—C14A—H14A	109.5	C44A—C41—C38	109.1 (9)
C11—C14A—H14B	109.5	C43A—C41—C38	111.8 (8)
H14A—C14A—H14B	109.5	C42B—C41—C44B	101.3 (9)
C11—C14A—H14C	109.5	C38—C41—C44B	108.1 (7)
H14A—C14A—H14C	109.5	C42B—C41—C43B	113.4 (8)
H14B—C14A—H14C	109.5	C38—C41—C43B	107.8 (6)
C11—C12B—H12D	109.5	C44B—C41—C43B	110.0 (9)
C11—C12B—H12E	109.5	C44A—C41—C42A	105.1 (11)
H12D—C12B—H12E	109.5	C43A—C41—C42A	108.6 (9)
C11—C12B—H12F	109.5	C38—C41—C42A	110.2 (7)
H12D—C12B—H12F	109.5	C41—C42A—H42A	109.5
H12E—C12B—H12F	109.5	C41—C42A—H42B	109.5
C11—C13B—H13D	109.5	H42A—C42A—H42B	109.5
C11—C13B—H13E	109.5	C41—C42A—H42C	109.5
H13D—C13B—H13E	109.5	H42A—C42A—H42C	109.5
C11—C13B—H13F	109.5	H42B—C42A—H42C	109.5
H13D—C13B—H13F	109.5	C41—C43A—H43A	109.5
H13E—C13B—H13F	109.5	C41—C43A—H43B	109.5
C11—C14B—H14D	109.5	H43A—C43A—H43B	109.5
C11—C14B—H14E	109.5	C41—C43A—H43C	109.5
H14D—C14B—H14E	109.5	H43A—C43A—H43C	109.5
C11—C14B—H14F	109.5	H43B—C43A—H43C	109.5
H14D—C14B—H14F	109.5	C41—C44A—H44A	109.5
H14E—C14B—H14F	109.5	C41—C44A—H44B	109.5
C20—C15—C16	118.5 (4)	H44A—C44A—H44B	109.5
C20—C15—C2	121.5 (3)	C41—C44A—H44C	109.5
C16—C15—C2	119.9 (4)	H44A—C44A—H44C	109.5
C17—C16—C15	120.4 (4)	H44B—C44A—H44C	109.5
C17—C16—H16	119.8	C41—C42B—H42D	109.5
C15—C16—H16	119.8	C41—C42B—H42E	109.5
C16—C17—C18	121.7 (4)	H42D—C42B—H42E	109.5
C16—C17—H17	119.1	C41—C42B—H42F	109.5
C18—C17—H17	119.1	H42D—C42B—H42F	109.5
C17—C18—C19	117.1 (4)	H42E—C42B—H42F	109.5
C17—C18—C21	122.7 (4)	C41—C43B—H43D	109.5
C19—C18—C21	120.1 (4)	C41—C43B—H43E	109.5
C20—C19—C18	121.3 (4)	H43D—C43B—H43E	109.5
C20—C19—H19	119.3	C41—C43B—H43F	109.5
C18—C19—H19	119.3	H43D—C43B—H43F	109.5
C19—C20—C15	120.9 (4)	H43E—C43B—H43F	109.5
C19—C20—H20	119.6	C41—C44B—H44D	109.5
C15—C20—H20	119.6	C41—C44B—H44E	109.5
C18—C21—C23	112.8 (3)	H44D—C44B—H44E	109.5
C18—C21—C22	108.3 (3)	C41—C44B—H44F	109.5
C23—C21—C22	109.0 (4)	H44D—C44B—H44F	109.5
C18—C21—C24	109.9 (3)	H44E—C44B—H44F	109.5
C23—C21—C24	107.9 (4)	C46ⁱ—C45—C46	133 (3)
C22—C21—C24	109.0 (4)	C46ⁱ—C45—H45A	104.0
C21—C22—H22A	109.5	C46—C45—H45A	104.0
C21—C22—H22B	109.5	C46ⁱ—C45—H45B	104.0
H22A—C22—H22B	109.5	C46—C45—H45B	104.0
C21—C22—H22C	109.5	H45A—C45—H45B	105.5
H22A—C22—H22C	109.5	C47—C46—C45	116 (2)
H22B—C22—H22C	109.5	C47—C46—H46A	108.2
C21—C23—H23A	109.5	C45—C46—H46A	108.2
C21—C23—H23B	109.5	C47—C46—H46B	108.2
H23A—C23—H23B	109.5	C45—C46—H46B	108.2
C21—C23—H23C	109.5	H46A—C46—H46B	107.3
H23A—C23—H23C	109.5	C46—C47—H47A	109.5
H23B—C23—H23C	109.5	C46—C47—H47B	109.5
C21—C24—H24A	109.5	H47A—C47—H47B	109.5
C21—C24—H24B	109.5	C46—C47—H47C	109.5
H24A—C24—H24B	109.5	H47A—C47—H47C	109.5
C21—C24—H24C	109.5	H47B—C47—H47C	109.5

Symmetry code: (i) −y, −x, −z+3/2.

Structural parameters (Å, °) for selected [M(S₂C₂Ar₂)₂] complexes (M = Ni²⁺, Pd²⁺, Pt²⁺, Au³⁺; Ar = aryl group) top

φ represents the angles between the MS₄C₄ MS4C4 mean plane and the aryl C₆ planes. Values of φ that were refined in SHELXL carry an uncertainty. All other values of φ were evaluated using Mercury 3.7.

Ar, M	Space group	M—S	S—C	C—C_chelate	φ	Refcode
Ph, Ni²⁺	P1	2.120, 2.127	1.701 (4), 1.695 (4)	1.424	50.64, 44.79	NIDPDS01^a
		2.125, 2.125	1.718 (4), 1.702 (4)	1.404	53.06, 34.75
Ph, Ni²⁺	P2₁/n	2.1209 (6)	1.7152 (17)	1.388 (2)	34.20	NIDPDS03^b
		2.1226 (7)	1.7035 (17)		65.77
Ph, Pd²⁺	P2₁/n	2.2502, 2.2496	1.696 (2), 1.712 (2)	1.399 (3)	35.83, 66.40	GOLRAA^c
Ph, Pt²⁺	P2₁/n	2.2443, 2.2460	1.6978, 1.7161	1.3965	35.87, 66.68	BUGDUC^d
MeO-p-C₆H₄, Ni²⁺	P1	2.1221 (6)	1.7169 (19)		29.40	SICWOR^e
		2.1218 (6)	1.7029 (19)	1.393 (3)	53.00
		2.1341 (5)	1.7171 (19)	1.391 (3)	41.61
		2.1182 (6)	1.7100 (19)		39.91
MeO-p-C₆H₄, Pd²⁺	P1	2.2535 (18)	1.699 (6)		40.24	SONPUI^f
		2.2566 (18)	1.715 (6)	1.417 (9)	43.57
		2.2706 (18)	1.711 (6)	1.411 (9)	30.22
		2.2505 (18)	1.708 (6)		51.76
MeO-p-C₆H₄, Pt²⁺	P1	2.240 (2), 2.243 (2)	1.696 (9), 1.710 (7)	1.402 (12)	40.83, 42.04	SOPMOB^f
		2.245 (3), 2.249 (3)	1.712 (8), 1.709 (9)	1.391 (12)	45.82, 38.35
MeO-p-C₆H₄, Ni²⁺	P1	2.104 (3), 2.108 (3)	1.689 (5), 1.699 (5)	1.394 (6)	40.41, 43.96	ECEKAA^b
		2.103 (3), 2.106 (3)	1.682 (5), 1.698 (5)	1.386 (6)	54.91, 35.28
Cl-p-C₆H₄, Ni²⁺	P1	2.1277 (7)	1.706 (2)		35.39 (9)	DATTUR^g
		2.1192 (6)	1.704 (2)	1.399 (3)	54.34 (5)
		2.1207 (7)	1.706 (2)	1.391 (3)	40.05 (6)
		2.1261 (6)	1.713 (2)		42.99 (7)
3,5-(MeO)₂-4-BuO-C₆H₂, Ni²⁺	P2₁/n	2.112	1.67 (1)		45.55	JUHJUR^h
		2.123	1.69 (2)	1.39 (2)	48.73
^tBu-p-C₆H₄, Ni²⁺, 1	P4₁2₁2	2.1175 (11)	1.717 (4)		41.7 (1)	This work
		2.1206 (12)	1.705 (4)	1.393 (6)	53.5 (1)
		2.1280 (11)	1.705 (4)	1.403 (6)	53.4 (1)
		2.1185 (11)	1.709 (4)		44.5 (2)
^tBu-p-C₆H₄, Pd²⁺	Pna2₁	2.2503 (10)			44.16	TEYSEWⁱ
		2.2443 (10)	1.707 (4)	1.393 (5)	49.40
		2.2667 (10)	1.712 (4)		51.77
		2.2440 (10)			51.38
^tBu-p-C₆H₄, Pt²⁺	Pna2₁	2.243 (2), 2.242 (2)	1.728 (9), 1.729 (8)	1.381 (12)	48.37, 44.80	TIDBEO^j
		2.259 (2), 2.243 (2)	1.709 (10), 1.685 (9)	1.404 (13)	52.30, 52.63
^tBu-p-C₆H₄, Au³⁺	P4₁2₁2	2.284 (5), 2.288 (5)	1.74 (2), 1.745 (18)	1.38 (2)	41.16, 56.21	TEYSASⁱ
		2.290 (5), 2.303 (5)	1.751 (19). 1.76 (2)	1.33 (2)	47.30, 54.24

Notes: (a) Megnamisi-Belombe & Nuber (1989); (b) Miao et al. (2011); (c) Sheu & Lee (1999); (d) Dessy et al. (1982); (e) Arumugam et al. (2007); (f) Chandrasekaran et al. (2014); (g) Koehne et al. (2022); (h) Nakazumi et al. (1992); (i) Kotakam et al. (2007); (j) Pap et al. (2007).

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Bis[1,2-bis­(4-tert-butyl­phen­yl)ethyl­ene-1,2-di­thiol­ato(1−)]nickel(II) pentane 0.25-solvate

Supporting information

Key indicators

checkCIF/PLATON results

Bis[1,2-bis(4-tert-butylphenyl)ethylene-1,2-dithiolato(1−)]nickel(II) pentane 0.25-solvate