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The crystal structure of the title compound consists of discrete octa­hedral complexes that are linked by inter­molecular N—H...S hydrogen bonds into a three-dimensional network that contains channels in which the hydrogen-bonded methanol mol­ecules are located.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989017015055/wm5421sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989017015055/wm5421Isup2.hkl
Contains datablock I

CCDC reference: 1580309

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.080
  • Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H21 .. S2 .. 2.89 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H31 .. N1 .. 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H34 .. S21 .. 2.95 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H35 .. N2 .. 2.68 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 3.079 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 8 Report PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 5 Note
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 9 Report PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.003 Degree PLAT230_ALERT_2_G Hirshfeld Test Diff for S1 -- C1 .. 9.4 s.u. PLAT230_ALERT_2_G Hirshfeld Test Diff for S2 -- C2 .. 10.6 s.u. PLAT230_ALERT_2_G Hirshfeld Test Diff for N1 -- C1 .. 7.0 s.u. PLAT230_ALERT_2_G Hirshfeld Test Diff for N2 -- C2 .. 7.7 s.u. PLAT432_ALERT_2_G Short Inter X...Y Contact S11 .. C22 .. 3.14 Ang. PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note C H4 O PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 7 ALERT level C = Check. Ensure it is not caused by an omission or oversight 10 ALERT level G = General information/check it is not something unexpected 1 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 4 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe, 2008); cell refinement: X-AREA (Stoe, 2008); data reduction: X-AREA (Stoe, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: publCIF (Westrip, 2010); software used to prepare material for publication: DIAMOND (Brandenburg, 1999).

Bis(pyridine-4-carbothioamide-κN1)bis(thiocyanato-κN)cobalt(II) methanol monosolvate top
Crystal data top
[Co(NCS)2(C6H6NS)4]·CH4OZ = 2
Mr = 759.88F(000) = 782
Triclinic, P1Dx = 1.481 Mg m3
a = 9.3136 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.4532 (5) ÅCell parameters from 26748 reflections
c = 16.1799 (6) Åθ = 1.8–28.0°
α = 70.584 (3)°µ = 0.91 mm1
β = 89.453 (3)°T = 200 K
γ = 74.996 (3)°Block, violet
V = 1703.51 (11) Å30.15 × 0.10 × 0.06 mm
Data collection top
Stoe IPDS-1
diffractometer
6873 reflections with I > 2σ(I)
ω scansRint = 0.029
Absorption correction: numerical
(X-RED32 and X-SHAPE; Stoe, 2008)
θmax = 28.0°, θmin = 1.8°
Tmin = 0.781, Tmax = 0.926h = 1212
26748 measured reflectionsk = 1616
8222 independent reflectionsl = 2121
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031 w = 1/[σ2(Fo2) + (0.0426P)2 + 0.3232P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.080(Δ/σ)max = 0.001
S = 1.07Δρmax = 0.34 e Å3
8222 reflectionsΔρmin = 0.37 e Å3
409 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0030 (7)
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
Co10.27982 (2)0.47102 (2)0.28964 (2)0.02307 (7)
N10.46073 (15)0.54348 (13)0.26565 (9)0.0314 (3)
C10.55593 (18)0.58580 (14)0.27195 (11)0.0300 (3)
S10.68741 (5)0.64636 (5)0.28192 (4)0.04785 (13)
N20.09728 (15)0.40149 (12)0.32138 (9)0.0299 (3)
C20.00111 (19)0.35654 (15)0.33143 (11)0.0318 (3)
S20.13229 (6)0.28999 (5)0.34636 (4)0.05500 (16)
N110.17465 (15)0.61256 (12)0.34077 (9)0.0281 (3)
C110.1060 (2)0.59454 (15)0.41509 (11)0.0334 (4)
H110.11980.51550.45360.040*
C120.0159 (2)0.68505 (15)0.43884 (11)0.0344 (4)
H120.02780.66830.49340.041*
C130.00972 (19)0.80101 (14)0.38169 (11)0.0294 (3)
C140.06193 (19)0.82030 (14)0.30472 (11)0.0307 (3)
H140.04740.89820.26400.037*
C150.15440 (19)0.72529 (14)0.28799 (11)0.0292 (3)
H150.20660.74020.23640.035*
C160.1113 (2)0.90116 (15)0.40209 (11)0.0334 (4)
S110.24145 (7)1.00294 (5)0.32725 (3)0.05019 (14)
N120.09385 (19)0.90110 (14)0.48257 (10)0.0391 (3)
H11N0.01950.84850.51910.059*
H12N0.15330.95210.50310.059*
N210.37050 (14)0.34643 (12)0.22359 (8)0.0261 (3)
C210.51800 (17)0.30357 (14)0.22423 (10)0.0282 (3)
H210.58160.32240.25970.034*
C220.58254 (18)0.23326 (14)0.17595 (11)0.0289 (3)
H220.68800.20460.17870.035*
C230.49188 (18)0.20501 (14)0.12339 (10)0.0282 (3)
C240.33894 (19)0.24933 (16)0.12248 (12)0.0346 (4)
H240.27300.23260.08700.041*
C250.28281 (18)0.31776 (16)0.17335 (11)0.0322 (3)
H250.17770.34590.17290.039*
C260.55584 (19)0.13437 (15)0.06639 (11)0.0321 (3)
S210.48865 (5)0.17821 (4)0.03746 (3)0.03921 (11)
N220.6715 (2)0.04167 (14)0.10307 (11)0.0461 (4)
H21N0.70890.00100.06890.069*
H22N0.70120.01870.15920.069*
N310.16434 (14)0.59080 (12)0.16328 (8)0.0258 (3)
C310.24284 (18)0.63003 (16)0.09577 (10)0.0313 (3)
H310.34800.59770.10240.038*
C320.17817 (18)0.71544 (16)0.01669 (11)0.0327 (4)
H320.23790.73910.03030.039*
C330.02558 (18)0.76625 (14)0.00659 (10)0.0274 (3)
C340.05686 (18)0.72709 (15)0.07659 (11)0.0310 (3)
H340.16160.76070.07260.037*
C350.01598 (18)0.63816 (15)0.15246 (11)0.0302 (3)
H350.04190.60920.19910.036*
C360.04773 (18)0.85862 (15)0.07826 (10)0.0288 (3)
S310.17011 (6)0.98271 (4)0.07939 (3)0.03822 (11)
N320.00718 (17)0.83122 (13)0.14892 (9)0.0343 (3)
H31N0.05010.76200.14720.051*
H32N0.05180.87720.20100.051*
N410.39825 (15)0.34459 (12)0.41333 (9)0.0274 (3)
C410.4822 (2)0.37337 (15)0.46472 (11)0.0361 (4)
H410.49230.45170.44570.043*
C420.5548 (2)0.29474 (15)0.54422 (11)0.0367 (4)
H420.61050.31990.57950.044*
C430.54595 (18)0.17943 (14)0.57193 (10)0.0278 (3)
C440.4615 (2)0.14806 (14)0.51807 (11)0.0330 (4)
H440.45340.06930.53430.040*
C450.3894 (2)0.23294 (14)0.44069 (11)0.0323 (3)
H450.33040.21080.40500.039*
C460.62759 (18)0.09095 (14)0.65609 (10)0.0285 (3)
S410.76058 (5)0.02709 (4)0.65401 (3)0.03816 (11)
N420.59116 (17)0.11527 (13)0.72785 (9)0.0342 (3)
H41N0.51240.17200.72850.051*
H42N0.63890.07310.77990.051*
O510.1577 (2)0.59710 (15)0.13645 (10)0.0604 (4)
H510.17930.60810.18860.091*
C510.2618 (3)0.4961 (2)0.07977 (18)0.0658 (7)
H51A0.35450.51590.07130.099*
H51B0.28230.43340.10570.099*
H51C0.22090.46860.02290.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.02305 (11)0.02408 (11)0.01983 (11)0.00347 (8)0.00100 (7)0.00676 (8)
N10.0281 (7)0.0329 (7)0.0307 (7)0.0080 (6)0.0002 (5)0.0080 (6)
C10.0281 (8)0.0293 (8)0.0294 (8)0.0015 (6)0.0040 (6)0.0109 (6)
S10.0289 (2)0.0497 (3)0.0759 (4)0.0142 (2)0.0085 (2)0.0329 (3)
N20.0279 (7)0.0324 (7)0.0271 (7)0.0077 (6)0.0011 (5)0.0073 (5)
C20.0301 (8)0.0346 (8)0.0236 (7)0.0040 (7)0.0031 (6)0.0044 (6)
S20.0428 (3)0.0648 (3)0.0469 (3)0.0303 (3)0.0122 (2)0.0069 (2)
N110.0322 (7)0.0265 (6)0.0260 (6)0.0070 (5)0.0032 (5)0.0102 (5)
C110.0453 (10)0.0263 (8)0.0259 (8)0.0083 (7)0.0061 (7)0.0067 (6)
C120.0477 (10)0.0293 (8)0.0254 (8)0.0087 (7)0.0099 (7)0.0097 (6)
C130.0341 (8)0.0284 (8)0.0257 (7)0.0074 (6)0.0022 (6)0.0100 (6)
C140.0393 (9)0.0252 (7)0.0260 (8)0.0083 (7)0.0026 (7)0.0071 (6)
C150.0354 (8)0.0291 (8)0.0248 (7)0.0108 (6)0.0058 (6)0.0100 (6)
C160.0409 (9)0.0284 (8)0.0288 (8)0.0069 (7)0.0061 (7)0.0093 (6)
S110.0599 (3)0.0417 (3)0.0312 (2)0.0116 (2)0.0026 (2)0.00872 (19)
N120.0483 (9)0.0359 (8)0.0302 (7)0.0006 (7)0.0017 (7)0.0158 (6)
N210.0254 (6)0.0280 (6)0.0242 (6)0.0041 (5)0.0003 (5)0.0103 (5)
C210.0250 (7)0.0312 (8)0.0271 (8)0.0032 (6)0.0024 (6)0.0116 (6)
C220.0257 (7)0.0297 (8)0.0281 (8)0.0022 (6)0.0002 (6)0.0099 (6)
C230.0318 (8)0.0264 (7)0.0255 (7)0.0068 (6)0.0036 (6)0.0085 (6)
C240.0308 (8)0.0432 (9)0.0378 (9)0.0120 (7)0.0035 (7)0.0226 (8)
C250.0249 (7)0.0411 (9)0.0354 (9)0.0079 (7)0.0020 (6)0.0200 (7)
C260.0341 (8)0.0313 (8)0.0321 (8)0.0071 (7)0.0046 (7)0.0136 (7)
S210.0365 (2)0.0477 (3)0.0331 (2)0.00146 (19)0.00106 (18)0.02079 (19)
N220.0574 (10)0.0387 (8)0.0337 (8)0.0081 (7)0.0027 (7)0.0175 (7)
N310.0243 (6)0.0291 (6)0.0203 (6)0.0036 (5)0.0007 (5)0.0067 (5)
C310.0235 (7)0.0419 (9)0.0239 (8)0.0050 (7)0.0009 (6)0.0081 (7)
C320.0262 (8)0.0435 (9)0.0224 (7)0.0080 (7)0.0017 (6)0.0046 (7)
C330.0285 (7)0.0288 (7)0.0223 (7)0.0065 (6)0.0020 (6)0.0063 (6)
C340.0233 (7)0.0350 (8)0.0277 (8)0.0030 (6)0.0010 (6)0.0054 (6)
C350.0251 (7)0.0357 (8)0.0242 (8)0.0065 (6)0.0018 (6)0.0042 (6)
C360.0272 (7)0.0319 (8)0.0238 (7)0.0081 (6)0.0019 (6)0.0047 (6)
S310.0474 (3)0.0316 (2)0.0262 (2)0.00146 (18)0.00544 (18)0.00684 (16)
N320.0354 (7)0.0369 (8)0.0229 (7)0.0026 (6)0.0028 (6)0.0055 (6)
N410.0302 (7)0.0261 (6)0.0225 (6)0.0041 (5)0.0043 (5)0.0067 (5)
C410.0490 (10)0.0265 (8)0.0295 (8)0.0110 (7)0.0111 (7)0.0044 (6)
C420.0491 (10)0.0305 (8)0.0287 (8)0.0116 (7)0.0134 (7)0.0066 (7)
C430.0288 (7)0.0268 (7)0.0239 (7)0.0023 (6)0.0022 (6)0.0072 (6)
C440.0400 (9)0.0251 (8)0.0316 (8)0.0085 (7)0.0052 (7)0.0067 (6)
C450.0374 (9)0.0283 (8)0.0294 (8)0.0085 (7)0.0071 (7)0.0076 (6)
C460.0312 (8)0.0272 (7)0.0245 (7)0.0063 (6)0.0026 (6)0.0065 (6)
S410.0462 (3)0.0309 (2)0.0285 (2)0.00573 (18)0.00729 (18)0.01084 (16)
N420.0372 (8)0.0336 (7)0.0243 (7)0.0010 (6)0.0035 (6)0.0081 (6)
O510.0771 (11)0.0529 (9)0.0403 (8)0.0034 (8)0.0046 (8)0.0176 (7)
C510.0840 (18)0.0442 (12)0.0592 (15)0.0041 (12)0.0121 (13)0.0144 (11)
Geometric parameters (Å, º) top
Co1—N12.0847 (14)N22—H21N0.8800
Co1—N22.0865 (14)N22—H22N0.8800
Co1—N212.1608 (13)N31—C311.335 (2)
Co1—N312.1783 (12)N31—C351.342 (2)
Co1—N412.1792 (13)C31—C321.382 (2)
Co1—N112.1933 (14)C31—H310.9500
N1—C11.164 (2)C32—C331.384 (2)
C1—S11.6300 (18)C32—H320.9500
N2—C21.157 (2)C33—C341.386 (2)
C2—S21.6381 (18)C33—C361.495 (2)
N11—C111.336 (2)C34—C351.384 (2)
N11—C151.343 (2)C34—H340.9500
C11—C121.384 (2)C35—H350.9500
C11—H110.9500C36—N321.323 (2)
C12—C131.391 (2)C36—S311.6605 (17)
C12—H120.9500N32—H31N0.8800
C13—C141.386 (2)N32—H32N0.8799
C13—C161.489 (2)N41—C451.336 (2)
C14—C151.377 (2)N41—C411.336 (2)
C14—H140.9500C41—C421.381 (2)
C15—H150.9500C41—H410.9500
C16—N121.314 (2)C42—C431.379 (2)
C16—S111.6594 (18)C42—H420.9500
N12—H11N0.8799C43—C441.389 (2)
N12—H12N0.8800C43—C461.495 (2)
N21—C211.338 (2)C44—C451.380 (2)
N21—C251.346 (2)C44—H440.9500
C21—C221.383 (2)C45—H450.9500
C21—H210.9500C46—N421.314 (2)
C22—C231.388 (2)C46—S411.6690 (17)
C22—H220.9500N42—H41N0.8800
C23—C241.386 (2)N42—H42N0.8800
C23—C261.496 (2)O51—C511.408 (3)
C24—C251.380 (2)O51—H510.8400
C24—H240.9500C51—H51A0.9800
C25—H250.9500C51—H51B0.9800
C26—N221.326 (2)C51—H51C0.9800
C26—S211.6572 (18)
N1—Co1—N2176.11 (6)N22—C26—C23115.73 (15)
N1—Co1—N2192.32 (5)N22—C26—S21124.05 (14)
N2—Co1—N2191.06 (5)C23—C26—S21120.11 (12)
N1—Co1—N3191.36 (5)C26—N22—H21N115.1
N2—Co1—N3190.73 (5)C26—N22—H22N121.5
N21—Co1—N3187.09 (5)H21N—N22—H22N123.0
N1—Co1—N4189.20 (5)C31—N31—C35117.36 (13)
N2—Co1—N4188.87 (5)C31—N31—Co1119.81 (10)
N21—Co1—N4190.24 (5)C35—N31—Co1122.41 (11)
N31—Co1—N41177.29 (5)N31—C31—C32123.04 (15)
N1—Co1—N1187.53 (6)N31—C31—H31118.5
N2—Co1—N1189.35 (5)C32—C31—H31118.5
N21—Co1—N11172.94 (5)C31—C32—C33119.40 (16)
N31—Co1—N1185.85 (5)C31—C32—H32120.3
N41—Co1—N1196.82 (5)C33—C32—H32120.3
C1—N1—Co1163.69 (14)C32—C33—C34118.04 (14)
N1—C1—S1178.93 (16)C32—C33—C36120.67 (15)
C2—N2—Co1171.72 (14)C34—C33—C36121.28 (14)
N2—C2—S2178.71 (16)C35—C34—C33118.87 (15)
C11—N11—C15116.99 (14)C35—C34—H34120.6
C11—N11—Co1123.49 (11)C33—C34—H34120.6
C15—N11—Co1118.44 (11)N31—C35—C34123.21 (15)
N11—C11—C12123.40 (15)N31—C35—H35118.4
N11—C11—H11118.3C34—C35—H35118.4
C12—C11—H11118.3N32—C36—C33114.27 (15)
C11—C12—C13119.03 (16)N32—C36—S31124.92 (12)
C11—C12—H12120.5C33—C36—S31120.80 (12)
C13—C12—H12120.5C36—N32—H31N124.0
C14—C13—C12117.78 (15)C36—N32—H32N120.1
C14—C13—C16121.00 (15)H31N—N32—H32N114.8
C12—C13—C16121.22 (15)C45—N41—C41117.06 (14)
C15—C14—C13119.26 (15)C45—N41—Co1120.25 (10)
C15—C14—H14120.4C41—N41—Co1122.68 (11)
C13—C14—H14120.4N41—C41—C42123.16 (16)
N11—C15—C14123.42 (16)N41—C41—H41118.4
N11—C15—H15118.3C42—C41—H41118.4
C14—C15—H15118.3C43—C42—C41119.50 (15)
N12—C16—C13115.95 (15)C43—C42—H42120.2
N12—C16—S11123.07 (14)C41—C42—H42120.2
C13—C16—S11120.95 (13)C42—C43—C44117.72 (14)
C16—N12—H11N120.2C42—C43—C46120.89 (14)
C16—N12—H12N123.4C44—C43—C46121.37 (14)
H11N—N12—H12N116.3C45—C44—C43119.03 (15)
C21—N21—C25117.15 (14)C45—C44—H44120.5
C21—N21—Co1120.78 (10)C43—C44—H44120.5
C25—N21—Co1121.75 (11)N41—C45—C44123.49 (15)
N21—C21—C22123.32 (14)N41—C45—H45118.3
N21—C21—H21118.3C44—C45—H45118.3
C22—C21—H21118.3N42—C46—C43116.01 (14)
C21—C22—C23119.39 (15)N42—C46—S41124.26 (12)
C21—C22—H22120.3C43—C46—S41119.69 (12)
C23—C22—H22120.3C46—N42—H41N122.5
C24—C23—C22117.47 (15)C46—N42—H42N123.2
C24—C23—C26120.86 (15)H41N—N42—H42N114.2
C22—C23—C26121.61 (15)C51—O51—H51109.5
C25—C24—C23119.77 (15)O51—C51—H51A109.5
C25—C24—H24120.1O51—C51—H51B109.5
C23—C24—H24120.1H51A—C51—H51B109.5
N21—C25—C24122.88 (15)O51—C51—H51C109.5
N21—C25—H25118.6H51A—C51—H51C109.5
C24—C25—H25118.6H51B—C51—H51C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N12—H11N···S2i0.882.453.3010 (16)163
N12—H12N···S41ii0.882.643.3589 (16)140
C21—H21···S2iii0.952.893.7626 (16)153
N22—H21N···S31iv0.882.693.4969 (17)152
N22—H22N···S11iv0.882.713.5691 (17)166
C31—H31···N10.952.653.137 (2)112
C34—H34···S21v0.952.953.8809 (17)165
C35—H35···S1vi0.952.853.6906 (17)148
C35—H35···N20.952.683.203 (2)115
N32—H31N···O510.881.992.863 (2)173
N32—H32N···S41vii0.882.673.5176 (14)163
N42—H41N···S1viii0.882.493.3580 (16)171
N42—H42N···S31ix0.882.643.4935 (14)165
O51—H51···S2v0.842.433.1994 (17)153
Symmetry codes: (i) x, y+1, z+1; (ii) x1, y+1, z; (iii) x+1, y, z; (iv) x+1, y1, z; (v) x, y+1, z; (vi) x1, y, z; (vii) x1, y+1, z1; (viii) x+1, y+1, z+1; (ix) x+1, y1, z+1.
 

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