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In the title complex, (C12H11ClN)[Cu(C4N2S2)2], both anions and cations form segregated and regular columnar stacks.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045685/sa2018sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045685/sa2018Isup2.hkl
Contains datablock I

CCDC reference: 630444

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.034
  • wR factor = 0.090
  • Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C2 .. 5.26 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C2 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C4 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C5 - C6 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C7 - C8 ... 1.43 Ang.
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 10 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b.

1-(4-Chlorobenzyl)pyridinium bis(maleonitriledithiolato)copper(III) top
Crystal data top
(C12H11ClN)[Cu(C4N2S2)2]F(000) = 1104
Mr = 548.57Dx = 1.588 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.084 (2) ÅCell parameters from 801 reflections
b = 26.171 (5) Åθ = 3.1–22.4°
c = 7.4355 (15) ŵ = 1.45 mm1
β = 102.57 (3)°T = 293 K
V = 2295.0 (8) Å3Block, brown
Z = 40.25 × 0.15 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5255 independent reflections
Radiation source: fine-focus sealed tube3855 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.76, Tmax = 0.87k = 3333
22178 measured reflectionsl = 89
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0438P)2 + 0.4985P]
where P = (Fo2 + 2Fc2)/3
5255 reflections(Δ/σ)max = 0.001
280 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.33 e Å3
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
N50.27791 (17)0.42294 (7)0.1199 (3)0.0503 (5)
Cl10.23553 (10)0.16815 (3)0.00096 (11)0.0947 (3)
C90.3755 (3)0.42947 (11)0.1708 (5)0.0725 (8)
H9A0.44250.41770.09580.087*
C100.3780 (4)0.45333 (13)0.3323 (6)0.0891 (10)
H10A0.44640.45790.36840.107*
C110.2789 (4)0.47059 (12)0.4412 (4)0.0838 (10)
H11A0.27910.48680.55250.101*
C120.1803 (3)0.46386 (11)0.3853 (5)0.0781 (9)
H12A0.11230.47540.45780.094*
C130.1816 (2)0.44008 (10)0.2226 (4)0.0625 (7)
H13A0.11430.43580.18290.075*
C140.2768 (2)0.39592 (11)0.0563 (3)0.0622 (7)
H14A0.21310.40810.10440.075*
H14B0.34570.40410.14580.075*
C150.2679 (2)0.33880 (10)0.0327 (3)0.0492 (6)
C160.3629 (2)0.30848 (12)0.0755 (4)0.0678 (7)
H16A0.43390.32350.11290.081*
C170.3541 (3)0.25586 (12)0.0636 (4)0.0704 (8)
H17A0.41850.23540.09250.085*
C180.2490 (3)0.23438 (11)0.0086 (3)0.0588 (7)
C190.1535 (2)0.26374 (11)0.0371 (4)0.0696 (8)
H19A0.08260.24860.07530.084*
C200.1639 (2)0.31595 (11)0.0256 (4)0.0643 (7)
H20A0.09940.33620.05800.077*
Cu10.76462 (2)0.225013 (10)0.53759 (4)0.04240 (10)
S10.65452 (5)0.15992 (2)0.43973 (9)0.05046 (15)
S20.90720 (5)0.17599 (2)0.65704 (9)0.05453 (17)
S30.62814 (5)0.27685 (2)0.41405 (9)0.05315 (16)
S40.87876 (5)0.28799 (2)0.63778 (9)0.05535 (17)
N10.6684 (2)0.02087 (9)0.3781 (4)0.0806 (8)
N21.0093 (3)0.04658 (10)0.6614 (4)0.0888 (9)
N30.5608 (2)0.41329 (9)0.3539 (4)0.0830 (8)
N40.9029 (2)0.42673 (9)0.6168 (4)0.0786 (7)
C10.7054 (2)0.05960 (10)0.4318 (4)0.0562 (6)
C20.7483 (2)0.10886 (9)0.4939 (3)0.0458 (5)
C30.8564 (2)0.11594 (9)0.5849 (3)0.0470 (5)
C40.9387 (2)0.07612 (10)0.6263 (4)0.0582 (6)
C50.6192 (2)0.37972 (9)0.4034 (4)0.0537 (6)
C60.6893 (2)0.33634 (8)0.4644 (3)0.0439 (5)
C70.7976 (2)0.34099 (8)0.5561 (3)0.0434 (5)
C80.8544 (2)0.38909 (9)0.5895 (3)0.0525 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N50.0487 (12)0.0439 (10)0.0556 (11)0.0003 (9)0.0059 (9)0.0024 (9)
Cl10.1586 (10)0.0561 (4)0.0694 (5)0.0002 (5)0.0246 (5)0.0081 (4)
C90.0507 (16)0.0717 (18)0.094 (2)0.0025 (14)0.0134 (15)0.0128 (17)
C100.093 (3)0.074 (2)0.115 (3)0.0017 (18)0.053 (2)0.013 (2)
C110.130 (3)0.0517 (16)0.071 (2)0.0066 (19)0.023 (2)0.0093 (15)
C120.082 (2)0.0590 (17)0.082 (2)0.0013 (16)0.0074 (18)0.0109 (16)
C130.0504 (15)0.0543 (15)0.0792 (18)0.0009 (12)0.0059 (13)0.0045 (14)
C140.0667 (18)0.0653 (16)0.0519 (14)0.0014 (13)0.0071 (12)0.0015 (13)
C150.0468 (13)0.0573 (14)0.0426 (11)0.0003 (11)0.0078 (10)0.0039 (11)
C160.0432 (14)0.0781 (19)0.0773 (18)0.0001 (13)0.0029 (13)0.0057 (15)
C170.0578 (17)0.0740 (19)0.0782 (19)0.0204 (15)0.0119 (14)0.0077 (16)
C180.081 (2)0.0541 (14)0.0420 (12)0.0009 (13)0.0140 (12)0.0079 (11)
C190.0505 (15)0.0707 (18)0.0802 (19)0.0125 (14)0.0021 (14)0.0150 (16)
C200.0418 (14)0.0678 (17)0.0798 (18)0.0021 (12)0.0059 (13)0.0133 (15)
Cu10.04319 (16)0.03816 (15)0.04398 (16)0.00112 (11)0.00540 (11)0.00276 (11)
S10.0440 (3)0.0422 (3)0.0631 (4)0.0040 (2)0.0071 (3)0.0012 (3)
S20.0467 (3)0.0458 (3)0.0648 (4)0.0016 (3)0.0017 (3)0.0016 (3)
S30.0435 (3)0.0439 (3)0.0646 (4)0.0016 (2)0.0045 (3)0.0040 (3)
S40.0454 (3)0.0441 (3)0.0678 (4)0.0027 (3)0.0069 (3)0.0041 (3)
N10.0887 (19)0.0484 (13)0.0971 (19)0.0089 (13)0.0035 (15)0.0056 (13)
N20.087 (2)0.0687 (16)0.103 (2)0.0284 (15)0.0034 (16)0.0013 (15)
N30.0708 (17)0.0556 (14)0.114 (2)0.0160 (13)0.0017 (15)0.0005 (14)
N40.0765 (18)0.0509 (13)0.1017 (19)0.0143 (12)0.0050 (14)0.0043 (13)
C10.0580 (15)0.0464 (14)0.0618 (15)0.0015 (12)0.0075 (12)0.0024 (12)
C20.0522 (14)0.0400 (11)0.0462 (12)0.0033 (10)0.0132 (10)0.0010 (10)
C30.0548 (14)0.0420 (12)0.0456 (12)0.0048 (10)0.0141 (10)0.0043 (10)
C40.0627 (17)0.0502 (14)0.0596 (15)0.0056 (13)0.0088 (12)0.0006 (12)
C50.0503 (14)0.0441 (13)0.0641 (15)0.0027 (11)0.0068 (11)0.0035 (12)
C60.0476 (13)0.0385 (11)0.0450 (11)0.0007 (9)0.0089 (10)0.0013 (10)
C70.0475 (12)0.0376 (11)0.0454 (12)0.0009 (9)0.0107 (10)0.0001 (10)
C80.0515 (14)0.0475 (13)0.0573 (14)0.0014 (11)0.0091 (11)0.0002 (11)
Geometric parameters (Å, º) top
Cu1—S42.1740 (7)C9—C101.360 (4)
Cu1—S22.1765 (8)C9—H9A0.9300
Cu1—S32.1783 (8)C10—C111.369 (5)
Cu1—S12.1865 (7)C10—H10A0.9300
S1—C21.741 (2)C11—C121.356 (5)
S2—C31.729 (2)C11—H11A0.9300
S3—C61.729 (2)C12—C131.357 (4)
S4—C71.731 (2)C12—H12A0.9300
N1—C11.145 (3)C13—H13A0.9300
N2—C41.138 (3)C14—C151.506 (4)
N3—C51.137 (3)C14—H14A0.9700
N4—C81.142 (3)C14—H14B0.9700
N5—C131.323 (3)C15—C201.374 (3)
N5—C91.326 (3)C15—C161.374 (4)
N5—C141.491 (3)C16—C171.382 (4)
Cl1—C181.741 (3)C16—H16A0.9300
C1—C21.428 (3)C17—C181.368 (4)
C2—C31.347 (3)C17—H17A0.9300
C3—C41.427 (3)C18—C191.366 (4)
C5—C61.430 (3)C19—C201.373 (4)
C6—C71.343 (3)C19—H19A0.9300
C7—C81.430 (3)C20—H20A0.9300
S4—Cu1—S285.42 (3)C11—C10—H10A120.3
S4—Cu1—S392.18 (3)C12—C11—C10119.4 (3)
S2—Cu1—S3177.03 (3)C12—C11—H11A120.3
S4—Cu1—S1178.10 (3)C10—C11—H11A120.3
S2—Cu1—S192.68 (3)C11—C12—C13119.4 (3)
S3—Cu1—S189.71 (3)C11—C12—H12A120.3
C2—S1—Cu1101.70 (8)C13—C12—H12A120.3
C3—S2—Cu1102.31 (9)N5—C13—C12120.6 (3)
C6—S3—Cu1102.76 (8)N5—C13—H13A119.7
C7—S4—Cu1102.62 (8)C12—C13—H13A119.7
C13—N5—C9121.1 (2)N5—C14—C15112.5 (2)
C13—N5—C14119.5 (2)N5—C14—H14A109.1
C9—N5—C14119.4 (2)C15—C14—H14A109.1
N1—C1—C2177.8 (3)N5—C14—H14B109.1
C3—C2—C1122.0 (2)C15—C14—H14B109.1
C3—C2—S1121.45 (18)H14A—C14—H14B107.8
C1—C2—S1116.49 (19)C20—C15—C16118.8 (3)
C2—C3—C4124.2 (2)C20—C15—C14120.4 (2)
C2—C3—S2121.38 (18)C16—C15—C14120.8 (2)
C4—C3—S2114.41 (19)C15—C16—C17120.8 (3)
N2—C4—C3175.9 (3)C15—C16—H16A119.6
N3—C5—C6178.0 (3)C17—C16—H16A119.6
C7—C6—C5122.2 (2)C18—C17—C16118.8 (3)
C7—C6—S3120.98 (17)C18—C17—H17A120.6
C5—C6—S3116.79 (18)C16—C17—H17A120.6
C6—C7—C8123.1 (2)C19—C18—C17121.5 (3)
C6—C7—S4121.38 (17)C19—C18—Cl1118.9 (2)
C8—C7—S4115.50 (18)C17—C18—Cl1119.6 (2)
N4—C8—C7177.9 (3)C18—C19—C20118.9 (3)
N5—C9—C10120.2 (3)C18—C19—H19A120.6
N5—C9—H9A119.9C20—C19—H19A120.6
C10—C9—H9A119.9C19—C20—C15121.2 (3)
C9—C10—C11119.3 (3)C19—C20—H20A119.4
C9—C10—H10A120.3C15—C20—H20A119.4
S4—Cu1—S2—C3173.71 (9)C9—C10—C11—C120.4 (5)
S1—Cu1—S3—C6179.14 (9)C10—C11—C12—C130.1 (5)
S4—Cu1—S3—C60.62 (9)C11—C12—C13—N50.9 (4)
S2—Cu1—S4—C7176.44 (9)N5—C14—C15—C2084.1 (3)
S3—Cu1—S4—C71.81 (9)N5—C14—C15—C1698.3 (3)
S3—Cu1—S1—C2172.66 (9)C20—C15—C16—C171.2 (4)
S1—Cu1—S2—C36.10 (9)C16—C15—C20—C191.6 (4)
S2—Cu1—S1—C25.57 (9)C14—C15—C20—C19176.0 (2)
Cu1—S1—C2—C1174.36 (18)C14—C15—C16—C17176.4 (2)
Cu1—S1—C2—C33.8 (2)C15—C16—C17—C180.1 (4)
Cu1—S2—C3—C25.7 (2)C16—C17—C18—Cl1178.2 (2)
Cu1—S2—C3—C4172.94 (17)C16—C17—C18—C191.0 (4)
Cu1—S3—C6—C5178.90 (18)C17—C18—C19—C200.6 (4)
Cu1—S3—C6—C71.2 (2)Cl1—C18—C19—C20178.6 (2)
Cu1—S4—C7—C63.2 (2)C18—C19—C20—C150.7 (4)
Cu1—S4—C7—C8175.45 (16)C1—C2—C3—S2179.4 (2)
C13—N5—C9—C101.1 (4)S1—C2—C3—C4177.1 (2)
C13—N5—C14—C1593.5 (3)C1—C2—C3—C40.9 (4)
C14—N5—C9—C10179.0 (3)S1—C2—C3—S21.3 (3)
C14—N5—C13—C12178.7 (3)S3—C6—C7—S43.2 (3)
C9—N5—C14—C1586.6 (3)C5—C6—C7—C84.4 (4)
C9—N5—C13—C121.5 (4)S3—C6—C7—C8175.40 (18)
N5—C9—C10—C110.2 (5)C5—C6—C7—S4177.0 (2)
 

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