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The title compound, [Ni(S2C2(C6H4-p-Cl)2)2] or [Ni(C14H8Cl2S2)2], crystallizes in the triclinic space group P\overline{1} as pairs of mol­ecules disposed about an inversion center at the bc face of the cell. Close inter­molecular C—H...S (2.884 Å) and C—H...Ni (3.032 Å) contacts that are less than the sum of the van der Waals radii appear to induce slight bowing of the mol­ecular planes toward one another. The angles at which the four p-ClC6H4- rings join the NiS2C2 chelate rings [39.37 (9)– 53.41 (6)°] are similarly influenced by these inter­molecular contacts. In the larger packing arrangement, sheets of mol­ecules extend in the direction of the ac face diagonal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314622001481/gg4008sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314622001481/gg4008Isup2.hkl
Contains datablock I

CCDC reference: 2150616

Key indicators

  • Single-crystal X-ray study
  • T = 170 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.112
  • Data-to-parameter ratio = 24.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -0.507 Report PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 2 Report
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:C28 H16 Cl4 Ni1 S4 PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.002 Degree PLAT794_ALERT_5_G Tentative Bond Valency for Ni1 (III) . 3.19 Info PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 4 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 12 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 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 5 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX3 (Bruker, 2020); cell refinement: SAINT (Bruker, 2020); data reduction: SAINT (Bruker, 2020); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Bis[1,2-bis(4-chlorophenyl)-2-sulfanylideneethane-1-thiolato]nickel(II) top
Crystal data top
[Ni(C14H8Cl2S2)2]Z = 2
Mr = 681.16F(000) = 688
Triclinic, P1Dx = 1.594 Mg m3
a = 9.5487 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.4141 (4) ÅCell parameters from 9023 reflections
c = 15.0254 (6) Åθ = 2.4–29.5°
α = 107.486 (2)°µ = 1.37 mm1
β = 94.791 (2)°T = 170 K
γ = 111.423 (2)°Column, intense green
V = 1419.16 (10) Å30.27 × 0.15 × 0.10 mm
Data collection top
Bruker D8 QUEST PHOTON 3
diffractometer
8009 independent reflections
Radiation source: fine-focus sealed tube5941 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 7.3910 pixels mm-1θmax = 29.7°, θmin = 2.4°
φ and ω scansh = 1313
Absorption correction: numerical
(SADABS; Krause et al., 2015)
k = 1515
Tmin = 0.76, Tmax = 0.88l = 2020
89629 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0524P)2 + 1.0724P]
where P = (Fo2 + 2Fc2)/3
8009 reflections(Δ/σ)max = 0.001
334 parametersΔρmax = 0.78 e Å3
0 restraintsΔρmin = 0.45 e Å3
Special details top

Experimental. The diffraction data were obtained from sets 11 of frames, each of width 0.5° in ω or φ, collected with scan parameters determined by the "strategy" routine in APEX3. The scan time was 15 sec/frame.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å). All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.35173 (3)0.63386 (3)0.56629 (2)0.03136 (9)
Cl11.01198 (10)0.89129 (9)1.11457 (5)0.0646 (2)
Cl20.44766 (10)0.05522 (7)0.82193 (5)0.05315 (18)
Cl30.27660 (10)0.36001 (13)0.00470 (6)0.0866 (3)
Cl40.00224 (9)1.14473 (7)0.34765 (5)0.05241 (18)
S10.51018 (7)0.75530 (5)0.69986 (4)0.03387 (13)
S20.35562 (7)0.45659 (5)0.58196 (4)0.03250 (13)
S30.19444 (7)0.50969 (5)0.43335 (4)0.03449 (13)
S40.32801 (6)0.80720 (5)0.55486 (4)0.03159 (12)
C10.6573 (3)0.7049 (2)0.83698 (16)0.0316 (4)
C20.6637 (3)0.8171 (2)0.91031 (18)0.0402 (5)
H20.5913920.8541760.9020390.048*
C30.7730 (3)0.8754 (3)0.99479 (19)0.0458 (6)
H30.7765860.9524161.0439370.055*
C40.8768 (3)0.8206 (3)1.00694 (18)0.0423 (6)
C50.8749 (3)0.7106 (3)0.9358 (2)0.0460 (6)
H50.9477980.6744050.9448450.055*
C60.7664 (3)0.6533 (3)0.85115 (18)0.0392 (5)
H60.7656550.5778250.8018090.047*
C70.5440 (3)0.6456 (2)0.74536 (16)0.0307 (4)
C80.4672 (3)0.5076 (2)0.69248 (16)0.0314 (4)
C90.4672 (2)0.3986 (2)0.72654 (16)0.0296 (4)
C100.4301 (3)0.3963 (2)0.81393 (16)0.0334 (5)
H100.4103170.4680580.8537270.040*
C110.4218 (3)0.2903 (2)0.84348 (17)0.0353 (5)
H110.3944130.2881010.9024880.042*
C120.4541 (3)0.1880 (2)0.78565 (17)0.0343 (5)
C130.4911 (3)0.1876 (2)0.69874 (17)0.0349 (5)
H130.5125440.1162880.6598640.042*
C140.4966 (3)0.2923 (2)0.66892 (17)0.0325 (5)
H140.5205690.2920320.6087830.039*
C150.0353 (3)0.5525 (2)0.29789 (17)0.0330 (5)
C160.0885 (3)0.4265 (3)0.27169 (19)0.0409 (5)
H160.1068810.3813480.3161520.049*
C170.1839 (3)0.3672 (3)0.1819 (2)0.0527 (7)
H170.2681220.2818520.1644210.063*
C180.1553 (3)0.4339 (3)0.11759 (19)0.0512 (7)
C190.0334 (3)0.5563 (3)0.14068 (19)0.0475 (6)
H190.0150780.6000080.0954170.057*
C200.0625 (3)0.6152 (3)0.23024 (18)0.0395 (5)
H200.1479570.6993440.2462130.047*
C210.1388 (2)0.6145 (2)0.39363 (16)0.0308 (4)
C220.1954 (2)0.7506 (2)0.45073 (16)0.0304 (4)
C230.1474 (2)0.8490 (2)0.42788 (15)0.0295 (4)
C240.0076 (3)0.8158 (2)0.39296 (17)0.0343 (5)
H240.0829640.7297870.3859170.041*
C250.0535 (3)0.9061 (2)0.36839 (17)0.0353 (5)
H250.1591360.8821270.3440000.042*
C260.0569 (3)1.0315 (2)0.37998 (17)0.0349 (5)
C270.2113 (3)1.0700 (2)0.41777 (18)0.0349 (5)
H270.2854231.1577010.4274170.042*
C280.2555 (3)0.9781 (2)0.44116 (17)0.0319 (4)
H280.3609931.0033210.4666670.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.03557 (16)0.02817 (15)0.03695 (16)0.01568 (12)0.01086 (12)0.01650 (12)
Cl10.0720 (5)0.0606 (5)0.0441 (4)0.0149 (4)0.0060 (3)0.0158 (3)
Cl20.0827 (5)0.0370 (3)0.0519 (4)0.0335 (3)0.0112 (3)0.0221 (3)
Cl30.0569 (5)0.1278 (9)0.0417 (4)0.0310 (5)0.0044 (3)0.0022 (5)
Cl40.0681 (4)0.0482 (4)0.0639 (4)0.0402 (3)0.0187 (3)0.0293 (3)
S10.0401 (3)0.0266 (3)0.0392 (3)0.0155 (2)0.0100 (2)0.0150 (2)
S20.0382 (3)0.0270 (3)0.0364 (3)0.0152 (2)0.0095 (2)0.0143 (2)
S30.0407 (3)0.0255 (3)0.0398 (3)0.0148 (2)0.0085 (2)0.0136 (2)
S40.0346 (3)0.0263 (3)0.0358 (3)0.0140 (2)0.0065 (2)0.0121 (2)
C10.0365 (11)0.0275 (10)0.0344 (11)0.0145 (9)0.0131 (9)0.0126 (9)
C20.0494 (14)0.0340 (12)0.0426 (13)0.0231 (11)0.0139 (11)0.0126 (10)
C30.0614 (17)0.0352 (13)0.0393 (13)0.0203 (12)0.0158 (12)0.0095 (11)
C40.0470 (14)0.0411 (13)0.0370 (12)0.0132 (11)0.0078 (11)0.0183 (11)
C50.0453 (14)0.0478 (15)0.0491 (15)0.0244 (12)0.0081 (12)0.0169 (12)
C60.0429 (13)0.0389 (13)0.0388 (12)0.0226 (11)0.0115 (10)0.0100 (10)
C70.0331 (11)0.0318 (11)0.0379 (11)0.0182 (9)0.0162 (9)0.0186 (9)
C80.0366 (11)0.0325 (11)0.0360 (11)0.0201 (9)0.0160 (9)0.0171 (9)
C90.0310 (10)0.0260 (10)0.0358 (11)0.0143 (8)0.0100 (9)0.0125 (9)
C100.0403 (12)0.0303 (11)0.0365 (11)0.0199 (10)0.0137 (9)0.0131 (9)
C110.0448 (13)0.0326 (11)0.0346 (11)0.0197 (10)0.0103 (10)0.0151 (9)
C120.0384 (12)0.0292 (11)0.0386 (12)0.0163 (9)0.0027 (9)0.0149 (9)
C130.0378 (12)0.0283 (11)0.0408 (12)0.0180 (9)0.0081 (10)0.0099 (9)
C140.0341 (11)0.0297 (11)0.0369 (11)0.0159 (9)0.0122 (9)0.0117 (9)
C150.0331 (11)0.0297 (11)0.0371 (12)0.0164 (9)0.0089 (9)0.0082 (9)
C160.0363 (12)0.0365 (12)0.0449 (14)0.0140 (10)0.0136 (10)0.0079 (11)
C170.0325 (13)0.0517 (16)0.0531 (16)0.0120 (12)0.0110 (12)0.0032 (13)
C180.0410 (14)0.0702 (19)0.0369 (13)0.0308 (14)0.0056 (11)0.0028 (13)
C190.0536 (16)0.0589 (17)0.0385 (13)0.0344 (14)0.0107 (12)0.0145 (12)
C200.0444 (13)0.0385 (13)0.0404 (13)0.0219 (11)0.0105 (10)0.0139 (10)
C210.0303 (10)0.0281 (10)0.0397 (12)0.0141 (9)0.0116 (9)0.0161 (9)
C220.0286 (10)0.0309 (11)0.0385 (11)0.0149 (9)0.0119 (9)0.0170 (9)
C230.0318 (11)0.0277 (10)0.0327 (11)0.0142 (9)0.0107 (9)0.0121 (9)
C240.0307 (11)0.0293 (11)0.0458 (13)0.0127 (9)0.0127 (10)0.0157 (10)
C250.0307 (11)0.0374 (12)0.0408 (12)0.0177 (9)0.0073 (9)0.0132 (10)
C260.0466 (13)0.0349 (12)0.0363 (12)0.0270 (10)0.0141 (10)0.0161 (10)
C270.0372 (12)0.0255 (10)0.0453 (13)0.0128 (9)0.0168 (10)0.0152 (9)
C280.0301 (10)0.0278 (10)0.0393 (12)0.0131 (9)0.0106 (9)0.0117 (9)
Geometric parameters (Å, º) top
Ni1—S22.1192 (6)C11—C121.383 (3)
Ni1—S32.1207 (7)C11—H110.9500
Ni1—S42.1261 (6)C12—C131.380 (3)
Ni1—S12.1277 (7)C13—C141.382 (3)
Cl1—C41.743 (3)C13—H130.9500
Cl2—C121.741 (2)C14—H140.9500
Cl3—C181.740 (3)C15—C201.400 (3)
Cl4—C261.733 (2)C15—C161.400 (3)
S1—C71.706 (2)C15—C211.479 (3)
S2—C81.704 (2)C16—C171.380 (4)
S3—C211.706 (2)C16—H160.9500
S4—C221.713 (2)C17—C181.387 (5)
C1—C21.393 (3)C17—H170.9500
C1—C61.402 (3)C18—C191.371 (4)
C1—C71.477 (3)C19—C201.379 (4)
C2—C31.381 (4)C19—H190.9500
C2—H20.9500C20—H200.9500
C3—C41.378 (4)C21—C221.397 (3)
C3—H30.9500C22—C231.473 (3)
C4—C51.376 (4)C23—C241.397 (3)
C5—C61.379 (4)C23—C281.398 (3)
C5—H50.9500C24—C251.386 (3)
C6—H60.9500C24—H240.9500
C7—C81.399 (3)C25—C261.381 (3)
C8—C91.480 (3)C25—H250.9500
C9—C101.394 (3)C26—C271.388 (3)
C9—C141.400 (3)C27—C281.386 (3)
C10—C111.387 (3)C27—H270.9500
C10—H100.9500C28—H280.9500
S2—Ni1—S387.80 (2)C12—C13—H13120.4
S2—Ni1—S4174.64 (3)C14—C13—H13120.4
S3—Ni1—S491.24 (2)C13—C14—C9120.6 (2)
S2—Ni1—S191.15 (2)C13—C14—H14119.7
S3—Ni1—S1178.94 (2)C9—C14—H14119.7
S4—Ni1—S189.82 (2)C20—C15—C16118.6 (2)
C7—S1—Ni1105.72 (8)C20—C15—C21121.0 (2)
C8—S2—Ni1105.67 (8)C16—C15—C21120.4 (2)
C21—S3—Ni1105.66 (8)C17—C16—C15120.6 (3)
C22—S4—Ni1105.76 (8)C17—C16—H16119.7
C2—C1—C6117.9 (2)C15—C16—H16119.7
C2—C1—C7121.3 (2)C16—C17—C18119.1 (3)
C6—C1—C7120.7 (2)C16—C17—H17120.5
C3—C2—C1121.3 (2)C18—C17—H17120.5
C3—C2—H2119.3C19—C18—C17121.6 (3)
C1—C2—H2119.3C19—C18—Cl3119.3 (2)
C4—C3—C2119.2 (2)C17—C18—Cl3119.1 (2)
C4—C3—H3120.4C18—C19—C20119.3 (3)
C2—C3—H3120.4C18—C19—H19120.3
C5—C4—C3121.1 (2)C20—C19—H19120.3
C5—C4—Cl1119.5 (2)C19—C20—C15120.8 (3)
C3—C4—Cl1119.4 (2)C19—C20—H20119.6
C4—C5—C6119.6 (2)C15—C20—H20119.6
C4—C5—H5120.2C22—C21—C15124.79 (19)
C6—C5—H5120.2C22—C21—S3119.14 (17)
C5—C6—C1120.9 (2)C15—C21—S3116.05 (16)
C5—C6—H6119.6C21—C22—C23124.3 (2)
C1—C6—H6119.6C21—C22—S4118.07 (16)
C8—C7—C1124.84 (19)C23—C22—S4117.60 (17)
C8—C7—S1118.29 (17)C24—C23—C28118.3 (2)
C1—C7—S1116.84 (16)C24—C23—C22120.7 (2)
C7—C8—C9125.3 (2)C28—C23—C22120.95 (19)
C7—C8—S2118.86 (16)C25—C24—C23121.3 (2)
C9—C8—S2115.76 (17)C25—C24—H24119.4
C10—C9—C14118.9 (2)C23—C24—H24119.4
C10—C9—C8120.74 (19)C26—C25—C24118.9 (2)
C14—C9—C8120.3 (2)C26—C25—H25120.6
C11—C10—C9120.8 (2)C24—C25—H25120.6
C11—C10—H10119.6C25—C26—C27121.5 (2)
C9—C10—H10119.6C25—C26—Cl4119.58 (18)
C12—C11—C10118.9 (2)C27—C26—Cl4118.88 (18)
C12—C11—H11120.5C28—C27—C26118.8 (2)
C10—C11—H11120.5C28—C27—H27120.6
C13—C12—C11121.6 (2)C26—C27—H27120.6
C13—C12—Cl2118.56 (18)C27—C28—C23121.1 (2)
C11—C12—Cl2119.87 (18)C27—C28—H28119.4
C12—C13—C14119.3 (2)C23—C28—H28119.4
C6—C1—C2—C30.5 (4)C20—C15—C16—C171.7 (4)
C7—C1—C2—C3177.8 (2)C21—C15—C16—C17179.0 (2)
C1—C2—C3—C40.6 (4)C15—C16—C17—C180.3 (4)
C2—C3—C4—C51.2 (4)C16—C17—C18—C190.9 (4)
C2—C3—C4—Cl1178.4 (2)C16—C17—C18—Cl3179.4 (2)
C3—C4—C5—C60.6 (4)C17—C18—C19—C200.6 (4)
Cl1—C4—C5—C6179.0 (2)Cl3—C18—C19—C20179.73 (19)
C4—C5—C6—C10.5 (4)C18—C19—C20—C150.9 (4)
C2—C1—C6—C51.1 (4)C16—C15—C20—C192.0 (3)
C7—C1—C6—C5178.4 (2)C21—C15—C20—C19179.3 (2)
C2—C1—C7—C8142.3 (2)C20—C15—C21—C2244.4 (3)
C6—C1—C7—C840.5 (3)C16—C15—C21—C22138.4 (2)
C2—C1—C7—S139.8 (3)C20—C15—C21—S3133.8 (2)
C6—C1—C7—S1137.4 (2)C16—C15—C21—S343.5 (3)
Ni1—S1—C7—C80.78 (19)Ni1—S3—C21—C222.11 (19)
Ni1—S1—C7—C1177.20 (14)Ni1—S3—C21—C15176.18 (15)
C1—C7—C8—C910.5 (3)C15—C21—C22—C236.6 (3)
S1—C7—C8—C9171.64 (17)S3—C21—C22—C23175.30 (17)
C1—C7—C8—S2172.99 (17)C15—C21—C22—S4174.10 (17)
S1—C7—C8—S24.8 (3)S3—C21—C22—S44.0 (3)
Ni1—S2—C8—C76.26 (19)Ni1—S4—C22—C213.77 (19)
Ni1—S2—C8—C9170.53 (14)Ni1—S4—C22—C23175.60 (14)
C7—C8—C9—C1051.3 (3)C21—C22—C23—C2442.9 (3)
S2—C8—C9—C10125.3 (2)S4—C22—C23—C24136.43 (19)
C7—C8—C9—C14132.1 (2)C21—C22—C23—C28137.6 (2)
S2—C8—C9—C1451.3 (3)S4—C22—C23—C2843.1 (3)
C14—C9—C10—C110.2 (3)C28—C23—C24—C252.5 (3)
C8—C9—C10—C11176.4 (2)C22—C23—C24—C25178.0 (2)
C9—C10—C11—C121.3 (4)C23—C24—C25—C260.7 (4)
C10—C11—C12—C131.3 (4)C24—C25—C26—C271.7 (4)
C10—C11—C12—Cl2178.92 (18)C24—C25—C26—Cl4178.84 (18)
C11—C12—C13—C140.2 (4)C25—C26—C27—C282.2 (4)
Cl2—C12—C13—C14179.98 (18)Cl4—C26—C27—C28178.26 (18)
C12—C13—C14—C90.9 (3)C26—C27—C28—C230.4 (3)
C10—C9—C14—C130.9 (3)C24—C23—C28—C271.9 (3)
C8—C9—C14—C13177.6 (2)C22—C23—C28—C27178.5 (2)
 

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