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The structure of the title compound is similar to that of the related complexes [Co(C12H8N4S)2(N3)2] and [Ni(C12H8N4S)2(N3)2] in which the azide ion is substituted by the thio­cyanate group. The CuN4S2 octa­hedron is more distorted than the CoN6 and NiN6 octa­hedra.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016011713/rz5192sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989016011713/rz5192Isup2.hkl
Contains datablock I

CCDC reference: 1494615

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.097
  • Data-to-parameter ratio = 21.9

checkCIF/PLATON results

No syntax errors found



Alert level G PLAT230_ALERT_2_G Hirshfeld Test Diff for S2 -- C13 .. 17.0 s.u. PLAT230_ALERT_2_G Hirshfeld Test Diff for N5 -- C13 .. 15.2 s.u. PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Cu1 -- S2 .. 12.2 s.u. PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Cu1 -- N2 .. 5.0 s.u. PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.30 Ratio PLAT774_ALERT_1_G Suspect X-Y Bond in CIF: S1 -- S2 .. 4.01 Ang. PLAT774_ALERT_1_G Suspect X-Y Bond in CIF: S2 -- S1 .. 4.01 Ang. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 9 Check C1 -C2 -S1 1.555 1.555 1.555 28.52 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 30 Check C7 -C8 -S1 1.555 1.555 1.555 32.59 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 50 Check C1 -N2 -S1 1.555 1.555 1.555 38.12 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 54 Check C7 -N3 -S1 1.555 1.555 1.555 37.70 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 59 Check C13 -N5 -S2 1.555 1.555 1.555 1.19 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 76 Check C1 -S1 -N2 1.555 1.555 1.555 28.28 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 79 Check C7 -S1 -N3 1.555 1.555 1.555 27.38 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 80 Check N2 -S1 -N3 1.555 1.555 1.555 31.13 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 82 Check C7 -S1 -C8 1.555 1.555 1.555 27.14 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 85 Check C1 -S1 -C2 1.555 1.555 1.555 23.90 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 94 Check C8 -S1 -N4 1.555 1.555 1.555 27.13 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 103 Check C13 -S2 -N5 1.555 1.555 1.555 0.81 Deg. PLAT794_ALERT_5_G Tentative Bond Valency for Cu1 (II) ..... 2.11 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 1 Note PLAT933_ALERT_2_G Number of OMIT records in Embedded RES ......... 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 10 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 0 ALERT level C = Check. Ensure it is not caused by an omission or oversight 23 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 13 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010).

Bis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole-κ2N2,N3]bis(thiocyanato-κS)copper(II) top
Crystal data top
[Cu(NCS)2(C12H8N4S)2]Dx = 1.635 Mg m3
Mr = 660.27Melting point: 538 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.0205 (3) ÅCell parameters from 4089 reflections
b = 7.8434 (3) Åθ = 2.5–30.5°
c = 21.3454 (9) ŵ = 1.17 mm1
β = 92.565 (2)°T = 296 K
V = 1341.45 (9) Å3Block, brown
Z = 20.35 × 0.32 × 0.26 mm
F(000) = 670
Data collection top
Bruker X8 APEX
diffractometer
4089 independent reflections
Radiation source: fine-focus sealed tube3155 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
φ and ω scansθmax = 30.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 1111
Tmin = 0.604, Tmax = 0.746k = 1111
42199 measured reflectionsl = 2730
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0418P)2 + 0.834P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4089 reflectionsΔρmax = 0.56 e Å3
187 parametersΔρmin = 0.51 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4345 (2)0.6803 (2)0.38733 (8)0.0240 (4)
C20.5958 (2)0.6037 (2)0.37724 (8)0.0240 (4)
C30.6786 (3)0.6181 (3)0.32209 (9)0.0327 (4)
H30.63140.67780.28810.039*
C40.8333 (3)0.5416 (3)0.31863 (10)0.0372 (5)
H40.89090.54690.28180.045*
C50.9012 (3)0.4572 (3)0.37055 (11)0.0366 (5)
H51.00650.40790.36960.044*
C60.8102 (3)0.4473 (3)0.42395 (10)0.0320 (4)
H60.85630.38960.45860.038*
C70.1712 (2)0.8133 (2)0.39355 (9)0.0251 (4)
C80.0124 (2)0.9022 (3)0.38144 (9)0.0270 (4)
C90.1027 (3)0.9212 (3)0.42773 (10)0.0322 (4)
H90.08040.87960.46800.039*
C100.2511 (3)1.0036 (3)0.41222 (12)0.0387 (5)
H100.33061.01980.44210.046*
C110.2792 (3)1.0615 (3)0.35150 (12)0.0430 (5)
H110.37821.11680.33960.052*
C120.1570 (3)1.0356 (3)0.30870 (12)0.0439 (6)
H120.17721.07470.26790.053*
C130.3302 (3)0.2765 (3)0.36867 (13)0.0423 (5)
N10.65894 (19)0.5170 (2)0.42789 (7)0.0246 (3)
N20.36607 (19)0.6566 (2)0.44138 (7)0.0258 (3)
N30.2129 (2)0.7323 (2)0.44510 (7)0.0282 (3)
N40.0124 (2)0.9581 (2)0.32252 (8)0.0354 (4)
N50.3255 (3)0.3117 (3)0.31799 (10)0.0568 (6)
Cu10.50000.50000.50000.02713 (10)
S10.31614 (6)0.80256 (7)0.33603 (2)0.02941 (12)
S20.33021 (9)0.22277 (9)0.44310 (3)0.04809 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0269 (9)0.0275 (9)0.0174 (8)0.0018 (7)0.0005 (6)0.0016 (7)
C20.0256 (8)0.0274 (9)0.0191 (8)0.0026 (7)0.0017 (6)0.0008 (7)
C30.0359 (10)0.0429 (12)0.0196 (9)0.0034 (9)0.0058 (7)0.0018 (8)
C40.0368 (11)0.0480 (13)0.0278 (11)0.0035 (9)0.0142 (8)0.0039 (9)
C50.0309 (10)0.0421 (12)0.0379 (12)0.0034 (9)0.0140 (9)0.0007 (9)
C60.0298 (10)0.0346 (10)0.0322 (11)0.0052 (8)0.0067 (8)0.0050 (8)
C70.0244 (8)0.0291 (9)0.0219 (9)0.0009 (7)0.0004 (6)0.0005 (7)
C80.0257 (9)0.0294 (9)0.0256 (9)0.0003 (7)0.0006 (7)0.0017 (7)
C90.0327 (10)0.0371 (11)0.0269 (10)0.0007 (8)0.0020 (8)0.0004 (8)
C100.0318 (10)0.0400 (12)0.0449 (13)0.0049 (9)0.0081 (9)0.0054 (10)
C110.0314 (11)0.0419 (12)0.0554 (15)0.0082 (9)0.0016 (10)0.0047 (11)
C120.0414 (12)0.0523 (14)0.0376 (13)0.0085 (11)0.0036 (10)0.0139 (11)
C130.0331 (11)0.0369 (12)0.0568 (16)0.0028 (9)0.0003 (10)0.0137 (11)
N10.0247 (7)0.0278 (8)0.0217 (8)0.0002 (6)0.0047 (6)0.0015 (6)
N20.0246 (7)0.0311 (8)0.0216 (8)0.0017 (6)0.0016 (6)0.0026 (6)
N30.0267 (8)0.0346 (9)0.0236 (8)0.0046 (7)0.0035 (6)0.0034 (7)
N40.0319 (9)0.0440 (10)0.0304 (9)0.0065 (8)0.0022 (7)0.0108 (8)
N50.0803 (17)0.0623 (15)0.0260 (10)0.0160 (13)0.0157 (10)0.0098 (10)
Cu10.02419 (16)0.0377 (2)0.02004 (17)0.00875 (13)0.00685 (11)0.00895 (13)
S10.0304 (2)0.0383 (3)0.0196 (2)0.0038 (2)0.00108 (17)0.00653 (19)
S20.0581 (4)0.0487 (4)0.0380 (3)0.0128 (3)0.0077 (3)0.0015 (3)
Geometric parameters (Å, º) top
C1—N21.313 (2)C10—C111.382 (4)
C1—C21.452 (3)C10—H100.9300
C1—S11.7106 (18)C11—C121.384 (4)
C2—N11.356 (2)C11—H110.9300
C2—C31.382 (3)C12—N41.331 (3)
C2—S12.8397 (19)C12—H120.9300
C3—C41.383 (3)C13—N51.115 (3)
C3—H30.9300C13—S21.644 (3)
C4—C51.382 (3)N1—Cu12.0463 (15)
C4—H40.9300N2—N31.370 (2)
C5—C61.383 (3)N2—Cu12.0267 (16)
C5—H50.9300N2—S12.5392 (16)
C6—N11.337 (2)N3—S12.5657 (16)
C6—H60.9300N4—S12.9062 (18)
C7—N31.301 (2)N5—S22.759 (2)
C7—C81.465 (3)Cu1—N2i2.0267 (16)
C7—S11.7300 (19)Cu1—N1i2.0463 (15)
C8—N41.338 (3)Cu1—S2i2.8124 (7)
C8—C91.390 (3)Cu1—S22.8125 (7)
C8—S12.774 (2)S1—S2ii4.0094 (9)
C9—C101.382 (3)S2—S1iii4.0094 (9)
C9—H90.9300
N2—C1—C2118.82 (16)N2—N3—S173.37 (9)
N2—C1—S1113.60 (14)C12—N4—C8116.71 (19)
C2—C1—S1127.58 (14)C12—N4—S1172.31 (16)
N1—C2—C3122.97 (18)C8—N4—S170.92 (11)
N1—C2—C1113.12 (15)C13—N5—S21.19 (15)
C3—C2—C1123.91 (18)N2—Cu1—N2i180.0
N1—C2—S1141.62 (12)N2—Cu1—N1i99.96 (6)
C3—C2—S195.40 (13)N2i—Cu1—N1i80.04 (6)
C1—C2—S128.52 (8)N2—Cu1—N180.04 (6)
C2—C3—C4118.45 (19)N2i—Cu1—N199.96 (6)
C2—C3—H3120.8N1i—Cu1—N1180.0
C4—C3—H3120.8N2—Cu1—S2i91.78 (5)
C5—C4—C3119.16 (19)N2i—Cu1—S2i88.22 (5)
C5—C4—H4120.4N1i—Cu1—S2i91.80 (5)
C3—C4—H4120.4N1—Cu1—S2i88.20 (5)
C4—C5—C6119.0 (2)N2—Cu1—S288.22 (5)
C4—C5—H5120.5N2i—Cu1—S291.78 (5)
C6—C5—H5120.5N1i—Cu1—S288.20 (5)
N1—C6—C5122.9 (2)N1—Cu1—S291.80 (5)
N1—C6—H6118.6S2i—Cu1—S2180.00 (2)
C5—C6—H6118.6C1—S1—C786.79 (9)
N3—C7—C8124.76 (17)C1—S1—N228.28 (7)
N3—C7—S1114.92 (14)C7—S1—N258.51 (7)
C8—C7—S1120.27 (14)C1—S1—N359.41 (7)
N4—C8—C9123.86 (18)C7—S1—N327.38 (7)
N4—C8—C7114.43 (17)N2—S1—N331.13 (5)
C9—C8—C7121.69 (18)C1—S1—C8113.89 (8)
N4—C8—S181.95 (12)C7—S1—C827.14 (7)
C9—C8—S1154.16 (14)N2—S1—C885.63 (5)
C7—C8—S132.59 (9)N3—S1—C854.50 (5)
C10—C9—C8118.2 (2)C1—S1—C223.90 (7)
C10—C9—H9120.9C7—S1—C2110.69 (7)
C8—C9—H9120.9N2—S1—C252.18 (5)
C9—C10—C11118.7 (2)N3—S1—C283.31 (5)
C9—C10—H10120.6C8—S1—C2137.77 (6)
C11—C10—H10120.6C1—S1—N4140.66 (7)
C10—C11—C12118.7 (2)C7—S1—N454.21 (7)
C10—C11—H11120.6N2—S1—N4112.55 (5)
C12—C11—H11120.6N3—S1—N481.50 (5)
N4—C12—C11123.8 (2)C8—S1—N427.13 (5)
N4—C12—H12118.1C2—S1—N4164.06 (5)
C11—C12—H12118.1C1—S1—S2ii95.46 (7)
N5—C13—S2178.0 (3)C7—S1—S2ii63.79 (7)
C6—N1—C2117.53 (16)N2—S1—S2ii82.33 (4)
C6—N1—Cu1128.20 (13)N3—S1—S2ii70.21 (4)
C2—N1—Cu1114.18 (12)C8—S1—S2ii64.66 (4)
C1—N2—N3113.62 (15)C2—S1—S2ii105.86 (4)
C1—N2—Cu1113.43 (13)N4—S1—S2ii73.36 (4)
N3—N2—Cu1132.74 (12)C13—S2—N50.81 (10)
C1—N2—S138.12 (9)C13—S2—Cu1101.44 (9)
N3—N2—S175.50 (9)N5—S2—Cu1102.00 (6)
Cu1—N2—S1151.43 (8)C13—S2—S1iii70.19 (8)
C7—N3—N2111.07 (15)N5—S2—S1iii69.96 (5)
C7—N3—S137.70 (9)Cu1—S2—S1iii151.94 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z; (iii) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N5iv0.932.533.353 (3)147
C6—H6···N3i0.932.353.143 (3)142
C4—H4···N4v0.932.573.458 (3)161
Symmetry codes: (i) x+1, y+1, z+1; (iv) x+1, y+1/2, z+1/2; (v) x+1, y1/2, z+1/2.
 

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