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In the title complex, (C6H8N)2[Zn(dmit)2] (dmit is 2-thioxo-1,3-dithiole-4,5-dithiol­ate, C3S5), each Zn atom is coordinated by four dmit S atoms that define a distorted tetra­hedral arrangement. The crystal structure is stabilized by C—H...S hydrogen bonding and S...S contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034434/tk6274sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034434/tk6274Isup2.hkl
Contains datablock I

CCDC reference: 289908

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.053
  • wR factor = 0.138
  • Data-to-parameter ratio = 19.1

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N2 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: The role of authors Wang, Yan Ling: the first author Yu, Wen Tao: determinate the structure Xu, Dong: synthesis Wang, Xin Qiang: synthesis Guo, Wen Feng: synthesis Zhang, Guang Hui: determinate the optical properties

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(N-methylpyridinium) bis(2-thioxo-1,3-dithiole-4,5-dithiolato)zincate(II) top
Crystal data top
(C6H8N)2[Zn(C3S5)2]F(000) = 1312
Mr = 646.30Dx = 1.657 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 30 reflections
a = 14.1687 (19) Åθ = 5.3–12.3°
b = 13.6246 (16) ŵ = 1.77 mm1
c = 14.024 (2) ÅT = 296 K
β = 106.865 (11)°Block, red
V = 2590.8 (6) Å30.40 × 0.36 × 0.31 mm
Z = 4
Data collection top
Bruker P4
diffractometer
3269 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 26.5°, θmin = 2.1°
ω scansh = 1717
Absorption correction: ψ scan
(XSCANS; Bruker, 1996)
k = 171
Tmin = 0.552, Tmax = 0.587l = 117
6564 measured reflections3 standard reflections every 97 reflections
5378 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0624P)2 + 1.3186P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
5378 reflectionsΔρmax = 0.66 e Å3
281 parametersΔρmin = 0.49 e Å3
54 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0039 (4)
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
xyzUiso*/Ueq
C11.0686 (3)0.7684 (4)0.4058 (4)0.0615 (15)
C20.8766 (3)0.7526 (4)0.3750 (4)0.0489 (12)
C30.9091 (3)0.6587 (4)0.3788 (4)0.0532 (13)
C40.4747 (4)0.5893 (4)0.3157 (4)0.0547 (13)
C50.4747 (4)0.5881 (4)0.2193 (4)0.0528 (12)
C60.2875 (4)0.5701 (4)0.2129 (5)0.0672 (16)
C70.8538 (8)0.9181 (7)0.6049 (8)0.166 (4)
H7A0.78520.93290.59420.249*
H7B0.87360.93930.54830.249*
H7C0.89240.95170.66340.249*
C80.9591 (5)0.7747 (7)0.6340 (5)0.101 (2)
H8A1.01410.81450.64110.121*
C90.9686 (7)0.6772 (8)0.6398 (6)0.121 (3)
H9A1.03070.64940.65100.145*
C100.8891 (7)0.6178 (7)0.6297 (6)0.133 (3)
H10A0.89580.54990.63060.159*
C110.8001 (7)0.6603 (7)0.6183 (6)0.119 (3)
H11A0.74530.62190.61630.142*
C120.7916 (6)0.7597 (7)0.6098 (5)0.103 (3)
H12A0.72990.78880.59810.123*
C130.5429 (7)0.3466 (6)0.0910 (6)0.130 (3)
H13A0.47240.35170.06660.195*
H13B0.56410.28780.06550.195*
H13C0.57250.40260.06940.195*
C140.5058 (5)0.3492 (5)0.2492 (7)0.090 (2)
H14A0.43910.35350.21500.108*
C150.5364 (6)0.3490 (5)0.3506 (7)0.098 (2)
H15A0.49060.35250.38640.117*
C160.6348 (6)0.3437 (6)0.3993 (6)0.111 (3)
H16A0.65670.34560.46860.133*
C170.6988 (6)0.3359 (6)0.3473 (7)0.103 (2)
H17A0.76560.32990.38060.124*
C180.6699 (5)0.3364 (5)0.2497 (6)0.0839 (19)
H18A0.71620.33230.21460.101*
N10.8689 (5)0.8147 (5)0.6179 (4)0.0916 (17)
N20.5731 (5)0.3430 (3)0.1997 (4)0.0755 (14)
S11.18119 (11)0.80862 (15)0.42218 (15)0.0903 (6)
S20.96808 (9)0.84290 (10)0.39239 (10)0.0576 (4)
S31.03617 (10)0.64565 (12)0.40077 (12)0.0679 (4)
S40.75521 (9)0.79096 (10)0.35236 (12)0.0639 (4)
S50.83913 (11)0.55215 (11)0.36545 (12)0.0679 (4)
S60.57550 (11)0.60265 (12)0.42015 (11)0.0677 (4)
S70.57637 (10)0.60064 (12)0.17480 (11)0.0619 (4)
S80.35874 (11)0.57555 (12)0.33468 (13)0.0718 (4)
S90.35934 (10)0.57362 (11)0.13191 (12)0.0668 (4)
S100.16741 (11)0.55873 (15)0.17715 (17)0.0998 (7)
Zn10.68832 (4)0.63263 (5)0.33119 (5)0.0574 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.046 (3)0.082 (4)0.052 (3)0.004 (3)0.007 (2)0.010 (3)
C20.044 (3)0.051 (3)0.050 (3)0.002 (2)0.010 (2)0.001 (2)
C30.043 (3)0.061 (3)0.052 (3)0.006 (2)0.009 (2)0.002 (3)
C40.051 (3)0.048 (3)0.069 (4)0.005 (2)0.023 (3)0.002 (3)
C50.047 (3)0.046 (3)0.063 (3)0.003 (2)0.012 (2)0.002 (3)
C60.057 (3)0.043 (3)0.103 (5)0.002 (3)0.025 (3)0.005 (3)
C70.228 (7)0.114 (5)0.161 (7)0.010 (5)0.065 (6)0.001 (5)
C80.097 (4)0.139 (6)0.074 (4)0.029 (4)0.036 (4)0.007 (4)
C90.115 (5)0.164 (6)0.088 (5)0.034 (5)0.035 (4)0.009 (5)
C100.185 (7)0.113 (6)0.100 (5)0.023 (5)0.043 (5)0.005 (4)
C110.133 (6)0.123 (6)0.089 (5)0.030 (5)0.014 (4)0.003 (5)
C120.080 (5)0.148 (8)0.077 (5)0.009 (5)0.016 (4)0.011 (5)
C130.166 (6)0.109 (5)0.102 (5)0.005 (5)0.018 (5)0.004 (4)
C140.070 (4)0.051 (4)0.152 (8)0.001 (3)0.036 (5)0.003 (4)
C150.120 (5)0.073 (4)0.122 (5)0.007 (4)0.070 (4)0.002 (4)
C160.146 (6)0.087 (5)0.097 (5)0.006 (4)0.032 (5)0.000 (4)
C170.098 (6)0.090 (6)0.118 (7)0.004 (4)0.025 (6)0.012 (5)
C180.075 (4)0.076 (5)0.108 (6)0.003 (4)0.039 (4)0.010 (4)
N10.137 (6)0.087 (4)0.060 (3)0.008 (4)0.044 (4)0.010 (3)
N20.100 (4)0.050 (3)0.075 (4)0.007 (3)0.023 (3)0.004 (3)
S10.0467 (8)0.1119 (15)0.1105 (14)0.0052 (9)0.0202 (9)0.0056 (12)
S20.0460 (7)0.0604 (9)0.0637 (8)0.0020 (6)0.0119 (6)0.0041 (7)
S30.0487 (7)0.0717 (10)0.0798 (10)0.0122 (7)0.0132 (7)0.0013 (8)
S40.0432 (7)0.0521 (8)0.0940 (11)0.0015 (6)0.0160 (7)0.0003 (8)
S50.0607 (8)0.0509 (8)0.0885 (11)0.0037 (7)0.0159 (8)0.0030 (8)
S60.0629 (9)0.0822 (11)0.0595 (9)0.0110 (8)0.0201 (7)0.0069 (8)
S70.0525 (7)0.0736 (10)0.0594 (8)0.0086 (7)0.0162 (6)0.0028 (7)
S80.0601 (8)0.0708 (10)0.0916 (11)0.0094 (7)0.0332 (8)0.0057 (9)
S90.0497 (7)0.0653 (9)0.0785 (10)0.0049 (7)0.0074 (7)0.0014 (8)
S100.0481 (8)0.0897 (13)0.1583 (19)0.0030 (8)0.0250 (10)0.0019 (13)
Zn10.0492 (3)0.0568 (4)0.0648 (4)0.0039 (3)0.0144 (3)0.0028 (3)
Geometric parameters (Å, º) top
Zn1—S42.3401 (15)C8—N11.347 (11)
Zn1—S52.3245 (16)C8—H8A0.9300
Zn1—S62.3315 (16)C9—C101.360 (14)
Zn1—S72.3447 (15)C9—H9A0.9300
S1—C11.639 (5)C10—C111.355 (14)
S2—C11.714 (5)C10—H10A0.9300
S3—C11.731 (6)C11—C121.362 (13)
C2—C31.355 (7)C11—H11A0.9300
S4—C21.737 (5)C12—N11.304 (9)
S2—C21.753 (5)C12—H12A0.9300
S5—C31.737 (5)C13—N21.460 (9)
S3—C31.746 (5)C13—H13A0.9600
C4—C51.352 (7)C13—H13B0.9600
S6—C41.734 (5)C13—H13C0.9600
S8—C41.749 (5)C14—N21.335 (8)
S7—C51.737 (5)C14—C151.360 (10)
S9—C51.746 (5)C14—H14A0.9300
S10—C61.635 (5)C15—C161.366 (13)
S8—C61.714 (6)C15—H15A0.9300
S9—C61.732 (6)C16—C171.323 (10)
C7—N11.429 (11)C16—H16A0.9300
C7—H7A0.9600C17—C181.310 (10)
C7—H7B0.9600C17—H17A0.9300
C7—H7C0.9600C18—N21.349 (8)
C8—C91.335 (11)C18—H18A0.9300
S1—C1—S2124.2 (4)N2—C13—H13B109.5
S1—C1—S3124.4 (3)H13A—C13—H13B109.5
S2—C1—S3111.4 (3)N2—C13—H13C109.5
C3—C2—S4126.8 (4)H13A—C13—H13C109.5
C3—C2—S2115.4 (4)H13B—C13—H13C109.5
S4—C2—S2117.8 (3)N2—C14—C15119.0 (7)
C2—C3—S5127.4 (4)N2—C14—H14A120.5
C2—C3—S3115.1 (4)C15—C14—H14A120.5
S5—C3—S3117.4 (3)C14—C15—C16119.5 (7)
C5—C4—S6127.4 (4)C14—C15—H15A120.3
C5—C4—S8115.1 (4)C16—C15—H15A120.3
S6—C4—S8117.6 (3)C17—C16—C15119.5 (8)
C4—C5—S7126.8 (4)C17—C16—H16A120.3
C4—C5—S9115.6 (4)C15—C16—H16A120.3
S7—C5—S9117.6 (3)C18—C17—C16121.3 (8)
S10—C6—S8124.7 (4)C18—C17—H17A119.4
S10—C6—S9123.9 (4)C16—C17—H17A119.4
S8—C6—S9111.3 (3)C17—C18—N2120.4 (7)
N1—C7—H7A109.5C17—C18—H18A119.8
N1—C7—H7B109.5N2—C18—H18A119.8
H7A—C7—H7B109.5C12—N1—C8120.9 (7)
N1—C7—H7C109.5C12—N1—C7117.7 (8)
H7A—C7—H7C109.5C8—N1—C7121.3 (8)
H7B—C7—H7C109.5C14—N2—C18120.4 (6)
C9—C8—N1119.1 (8)C14—N2—C13120.3 (7)
C9—C8—H8A120.5C18—N2—C13119.3 (7)
N1—C8—H8A120.5C1—S2—C299.0 (3)
C8—C9—C10121.4 (9)C1—S3—C399.0 (2)
C8—C9—H9A119.3C2—S4—Zn195.08 (17)
C10—C9—H9A119.3C3—S5—Zn195.13 (17)
C11—C10—C9118.2 (9)C4—S6—Zn195.22 (18)
C11—C10—H10A120.9C5—S7—Zn195.09 (18)
C9—C10—H10A120.9C6—S8—C499.3 (3)
C10—C11—C12119.4 (9)C6—S9—C598.7 (3)
C10—C11—H11A120.3S4—Zn1—S595.42 (5)
C12—C11—H11A120.3S4—Zn1—S6114.14 (6)
N1—C12—C11120.9 (8)S4—Zn1—S7115.42 (6)
N1—C12—H12A119.5S5—Zn1—S6122.58 (6)
C11—C12—H12A119.5S5—Zn1—S7115.94 (6)
N2—C13—H13A109.5S6—Zn1—S794.89 (5)
S4—C2—C3—S51.8 (8)C2—C3—S3—C11.5 (5)
S2—C2—C3—S5179.6 (3)S5—C3—S3—C1179.1 (3)
S4—C2—C3—S3178.8 (3)C3—C2—S4—Zn11.3 (5)
S2—C2—C3—S30.2 (6)S2—C2—S4—Zn1177.2 (3)
S6—C4—C5—S70.6 (8)C2—C3—S5—Zn13.7 (5)
S8—C4—C5—S7179.5 (3)S3—C3—S5—Zn1177.0 (3)
S6—C4—C5—S9179.8 (3)C5—C4—S6—Zn16.0 (5)
S8—C4—C5—S90.3 (6)S8—C4—S6—Zn1174.2 (3)
N1—C8—C9—C100.0 (13)C4—C5—S7—Zn15.1 (5)
C8—C9—C10—C113.1 (15)S9—C5—S7—Zn1174.1 (3)
C9—C10—C11—C124.9 (14)S10—C6—S8—C4179.0 (4)
C10—C11—C12—N13.7 (13)S9—C6—S8—C43.2 (3)
N2—C14—C15—C160.7 (11)C5—C4—S8—C62.2 (5)
C14—C15—C16—C172.0 (12)S6—C4—S8—C6178.0 (3)
C15—C16—C17—C182.3 (13)S10—C6—S9—C5179.2 (4)
C16—C17—C18—N21.4 (12)S8—C6—S9—C53.0 (3)
C11—C12—N1—C80.6 (11)C4—C5—S9—C61.7 (5)
C11—C12—N1—C7178.0 (8)S7—C5—S9—C6177.6 (3)
C9—C8—N1—C121.3 (11)C3—S5—Zn1—S6126.49 (18)
C9—C8—N1—C7176.1 (8)C3—S5—Zn1—S43.25 (18)
C15—C14—N2—C180.2 (9)C3—S5—Zn1—S7118.46 (18)
C15—C14—N2—C13177.8 (7)C4—S6—Zn1—S5131.77 (19)
C17—C18—N2—C140.1 (10)C4—S6—Zn1—S4114.06 (19)
C17—C18—N2—C13178.1 (7)C4—S6—Zn1—S76.62 (19)
S1—C1—S2—C2178.4 (4)C2—S4—Zn1—S52.68 (18)
S3—C1—S2—C22.0 (3)C2—S4—Zn1—S6132.13 (17)
C3—C2—S2—C11.2 (5)C2—S4—Zn1—S7119.44 (17)
S4—C2—S2—C1177.6 (3)C5—S7—Zn1—S5136.43 (18)
S1—C1—S3—C3178.3 (4)C5—S7—Zn1—S66.44 (18)
S2—C1—S3—C32.1 (3)C5—S7—Zn1—S4113.24 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···S10i0.932.713.632 (8)174
C14—H14A···S4ii0.932.773.644 (7)157
C18—H18A···S1iii0.932.743.655 (8)168
Symmetry codes: (i) x+1, y+3/2, z+1/2; (ii) x+1, y1/2, z+1/2; (iii) x+2, y1/2, z+1/2.
 

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