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
CCDC reference: 1580309
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean
(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
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]·CH4O | Z = 2 |
Mr = 759.88 | F(000) = 782 |
Triclinic, P1 | Dx = 1.481 Mg m−3 |
a = 9.3136 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.4532 (5) Å | Cell parameters from 26748 reflections |
c = 16.1799 (6) Å | θ = 1.8–28.0° |
α = 70.584 (3)° | µ = 0.91 mm−1 |
β = 89.453 (3)° | T = 200 K |
γ = 74.996 (3)° | Block, violet |
V = 1703.51 (11) Å3 | 0.15 × 0.10 × 0.06 mm |
Data collection top
Stoe IPDS-1 diffractometer | 6873 reflections with I > 2σ(I) |
ω scans | Rint = 0.029 |
Absorption correction: numerical (X-RED32 and X-SHAPE; Stoe, 2008) | θmax = 28.0°, θmin = 1.8° |
Tmin = 0.781, Tmax = 0.926 | h = −12→12 |
26748 measured reflections | k = −16→16 |
8222 independent reflections | l = −21→21 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-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 = 1.07 | Δρmax = 0.34 e Å−3 |
8222 reflections | Δρmin = −0.37 e Å−3 |
409 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction 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 | x | y | z | Uiso*/Ueq | |
Co1 | 0.27982 (2) | 0.47102 (2) | 0.28964 (2) | 0.02307 (7) | |
N1 | 0.46073 (15) | 0.54348 (13) | 0.26565 (9) | 0.0314 (3) | |
C1 | 0.55593 (18) | 0.58580 (14) | 0.27195 (11) | 0.0300 (3) | |
S1 | 0.68741 (5) | 0.64636 (5) | 0.28192 (4) | 0.04785 (13) | |
N2 | 0.09728 (15) | 0.40149 (12) | 0.32138 (9) | 0.0299 (3) | |
C2 | 0.00111 (19) | 0.35654 (15) | 0.33143 (11) | 0.0318 (3) | |
S2 | −0.13229 (6) | 0.28999 (5) | 0.34636 (4) | 0.05500 (16) | |
N11 | 0.17465 (15) | 0.61256 (12) | 0.34077 (9) | 0.0281 (3) | |
C11 | 0.1060 (2) | 0.59454 (15) | 0.41509 (11) | 0.0334 (4) | |
H11 | 0.1198 | 0.5155 | 0.4536 | 0.040* | |
C12 | 0.0159 (2) | 0.68505 (15) | 0.43884 (11) | 0.0344 (4) | |
H12 | −0.0278 | 0.6683 | 0.4934 | 0.041* | |
C13 | −0.00972 (19) | 0.80101 (14) | 0.38169 (11) | 0.0294 (3) | |
C14 | 0.06193 (19) | 0.82030 (14) | 0.30472 (11) | 0.0307 (3) | |
H14 | 0.0474 | 0.8982 | 0.2640 | 0.037* | |
C15 | 0.15440 (19) | 0.72529 (14) | 0.28799 (11) | 0.0292 (3) | |
H15 | 0.2066 | 0.7402 | 0.2364 | 0.035* | |
C16 | −0.1113 (2) | 0.90116 (15) | 0.40209 (11) | 0.0334 (4) | |
S11 | −0.24145 (7) | 1.00294 (5) | 0.32725 (3) | 0.05019 (14) | |
N12 | −0.09385 (19) | 0.90110 (14) | 0.48257 (10) | 0.0391 (3) | |
H11N | −0.0195 | 0.8485 | 0.5191 | 0.059* | |
H12N | −0.1533 | 0.9521 | 0.5031 | 0.059* | |
N21 | 0.37050 (14) | 0.34643 (12) | 0.22359 (8) | 0.0261 (3) | |
C21 | 0.51800 (17) | 0.30357 (14) | 0.22423 (10) | 0.0282 (3) | |
H21 | 0.5816 | 0.3224 | 0.2597 | 0.034* | |
C22 | 0.58254 (18) | 0.23326 (14) | 0.17595 (11) | 0.0289 (3) | |
H22 | 0.6880 | 0.2046 | 0.1787 | 0.035* | |
C23 | 0.49188 (18) | 0.20501 (14) | 0.12339 (10) | 0.0282 (3) | |
C24 | 0.33894 (19) | 0.24933 (16) | 0.12248 (12) | 0.0346 (4) | |
H24 | 0.2730 | 0.2326 | 0.0870 | 0.041* | |
C25 | 0.28281 (18) | 0.31776 (16) | 0.17335 (11) | 0.0322 (3) | |
H25 | 0.1777 | 0.3459 | 0.1729 | 0.039* | |
C26 | 0.55584 (19) | 0.13437 (15) | 0.06639 (11) | 0.0321 (3) | |
S21 | 0.48865 (5) | 0.17821 (4) | −0.03746 (3) | 0.03921 (11) | |
N22 | 0.6715 (2) | 0.04167 (14) | 0.10307 (11) | 0.0461 (4) | |
H21N | 0.7089 | 0.0010 | 0.0689 | 0.069* | |
H22N | 0.7012 | 0.0187 | 0.1592 | 0.069* | |
N31 | 0.16434 (14) | 0.59080 (12) | 0.16328 (8) | 0.0258 (3) | |
C31 | 0.24284 (18) | 0.63003 (16) | 0.09577 (10) | 0.0313 (3) | |
H31 | 0.3480 | 0.5977 | 0.1024 | 0.038* | |
C32 | 0.17817 (18) | 0.71544 (16) | 0.01669 (11) | 0.0327 (4) | |
H32 | 0.2379 | 0.7391 | −0.0303 | 0.039* | |
C33 | 0.02558 (18) | 0.76625 (14) | 0.00659 (10) | 0.0274 (3) | |
C34 | −0.05686 (18) | 0.72709 (15) | 0.07659 (11) | 0.0310 (3) | |
H34 | −0.1616 | 0.7607 | 0.0726 | 0.037* | |
C35 | 0.01598 (18) | 0.63816 (15) | 0.15246 (11) | 0.0302 (3) | |
H35 | −0.0419 | 0.6092 | 0.1991 | 0.036* | |
C36 | −0.04773 (18) | 0.85862 (15) | −0.07826 (10) | 0.0288 (3) | |
S31 | −0.17011 (6) | 0.98271 (4) | −0.07939 (3) | 0.03822 (11) | |
N32 | −0.00718 (17) | 0.83122 (13) | −0.14892 (9) | 0.0343 (3) | |
H31N | 0.0501 | 0.7620 | −0.1472 | 0.051* | |
H32N | −0.0518 | 0.8772 | −0.2010 | 0.051* | |
N41 | 0.39825 (15) | 0.34459 (12) | 0.41333 (9) | 0.0274 (3) | |
C41 | 0.4822 (2) | 0.37337 (15) | 0.46472 (11) | 0.0361 (4) | |
H41 | 0.4923 | 0.4517 | 0.4457 | 0.043* | |
C42 | 0.5548 (2) | 0.29474 (15) | 0.54422 (11) | 0.0367 (4) | |
H42 | 0.6105 | 0.3199 | 0.5795 | 0.044* | |
C43 | 0.54595 (18) | 0.17943 (14) | 0.57193 (10) | 0.0278 (3) | |
C44 | 0.4615 (2) | 0.14806 (14) | 0.51807 (11) | 0.0330 (4) | |
H44 | 0.4534 | 0.0693 | 0.5343 | 0.040* | |
C45 | 0.3894 (2) | 0.23294 (14) | 0.44069 (11) | 0.0323 (3) | |
H45 | 0.3304 | 0.2108 | 0.4050 | 0.039* | |
C46 | 0.62759 (18) | 0.09095 (14) | 0.65609 (10) | 0.0285 (3) | |
S41 | 0.76058 (5) | −0.02709 (4) | 0.65401 (3) | 0.03816 (11) | |
N42 | 0.59116 (17) | 0.11527 (13) | 0.72785 (9) | 0.0342 (3) | |
H41N | 0.5124 | 0.1720 | 0.7285 | 0.051* | |
H42N | 0.6389 | 0.0731 | 0.7799 | 0.051* | |
O51 | 0.1577 (2) | 0.59710 (15) | −0.13645 (10) | 0.0604 (4) | |
H51 | 0.1793 | 0.6081 | −0.1886 | 0.091* | |
C51 | 0.2618 (3) | 0.4961 (2) | −0.07977 (18) | 0.0658 (7) | |
H51A | 0.3545 | 0.5159 | −0.0713 | 0.099* | |
H51B | 0.2823 | 0.4334 | −0.1057 | 0.099* | |
H51C | 0.2209 | 0.4686 | −0.0229 | 0.099* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.02305 (11) | 0.02408 (11) | 0.01983 (11) | −0.00347 (8) | −0.00100 (7) | −0.00676 (8) |
N1 | 0.0281 (7) | 0.0329 (7) | 0.0307 (7) | −0.0080 (6) | −0.0002 (5) | −0.0080 (6) |
C1 | 0.0281 (8) | 0.0293 (8) | 0.0294 (8) | −0.0015 (6) | 0.0040 (6) | −0.0109 (6) |
S1 | 0.0289 (2) | 0.0497 (3) | 0.0759 (4) | −0.0142 (2) | 0.0085 (2) | −0.0329 (3) |
N2 | 0.0279 (7) | 0.0324 (7) | 0.0271 (7) | −0.0077 (6) | 0.0011 (5) | −0.0073 (5) |
C2 | 0.0301 (8) | 0.0346 (8) | 0.0236 (7) | −0.0040 (7) | −0.0031 (6) | −0.0044 (6) |
S2 | 0.0428 (3) | 0.0648 (3) | 0.0469 (3) | −0.0303 (3) | −0.0122 (2) | 0.0069 (2) |
N11 | 0.0322 (7) | 0.0265 (6) | 0.0260 (6) | −0.0070 (5) | 0.0032 (5) | −0.0102 (5) |
C11 | 0.0453 (10) | 0.0263 (8) | 0.0259 (8) | −0.0083 (7) | 0.0061 (7) | −0.0067 (6) |
C12 | 0.0477 (10) | 0.0293 (8) | 0.0254 (8) | −0.0087 (7) | 0.0099 (7) | −0.0097 (6) |
C13 | 0.0341 (8) | 0.0284 (8) | 0.0257 (7) | −0.0074 (6) | 0.0022 (6) | −0.0100 (6) |
C14 | 0.0393 (9) | 0.0252 (7) | 0.0260 (8) | −0.0083 (7) | 0.0026 (7) | −0.0071 (6) |
C15 | 0.0354 (8) | 0.0291 (8) | 0.0248 (7) | −0.0108 (6) | 0.0058 (6) | −0.0100 (6) |
C16 | 0.0409 (9) | 0.0284 (8) | 0.0288 (8) | −0.0069 (7) | 0.0061 (7) | −0.0093 (6) |
S11 | 0.0599 (3) | 0.0417 (3) | 0.0312 (2) | 0.0116 (2) | −0.0026 (2) | −0.00872 (19) |
N12 | 0.0483 (9) | 0.0359 (8) | 0.0302 (7) | −0.0006 (7) | 0.0017 (7) | −0.0158 (6) |
N21 | 0.0254 (6) | 0.0280 (6) | 0.0242 (6) | −0.0041 (5) | 0.0003 (5) | −0.0103 (5) |
C21 | 0.0250 (7) | 0.0312 (8) | 0.0271 (8) | −0.0032 (6) | −0.0024 (6) | −0.0116 (6) |
C22 | 0.0257 (7) | 0.0297 (8) | 0.0281 (8) | −0.0022 (6) | 0.0002 (6) | −0.0099 (6) |
C23 | 0.0318 (8) | 0.0264 (7) | 0.0255 (7) | −0.0068 (6) | 0.0036 (6) | −0.0085 (6) |
C24 | 0.0308 (8) | 0.0432 (9) | 0.0378 (9) | −0.0120 (7) | 0.0035 (7) | −0.0226 (8) |
C25 | 0.0249 (7) | 0.0411 (9) | 0.0354 (9) | −0.0079 (7) | 0.0020 (6) | −0.0200 (7) |
C26 | 0.0341 (8) | 0.0313 (8) | 0.0321 (8) | −0.0071 (7) | 0.0046 (7) | −0.0136 (7) |
S21 | 0.0365 (2) | 0.0477 (3) | 0.0331 (2) | −0.00146 (19) | −0.00106 (18) | −0.02079 (19) |
N22 | 0.0574 (10) | 0.0387 (8) | 0.0337 (8) | 0.0081 (7) | −0.0027 (7) | −0.0175 (7) |
N31 | 0.0243 (6) | 0.0291 (6) | 0.0203 (6) | −0.0036 (5) | −0.0007 (5) | −0.0067 (5) |
C31 | 0.0235 (7) | 0.0419 (9) | 0.0239 (8) | −0.0050 (7) | 0.0009 (6) | −0.0081 (7) |
C32 | 0.0262 (8) | 0.0435 (9) | 0.0224 (7) | −0.0080 (7) | 0.0017 (6) | −0.0046 (7) |
C33 | 0.0285 (7) | 0.0288 (7) | 0.0223 (7) | −0.0065 (6) | −0.0020 (6) | −0.0063 (6) |
C34 | 0.0233 (7) | 0.0350 (8) | 0.0277 (8) | −0.0030 (6) | −0.0010 (6) | −0.0054 (6) |
C35 | 0.0251 (7) | 0.0357 (8) | 0.0242 (8) | −0.0065 (6) | 0.0018 (6) | −0.0042 (6) |
C36 | 0.0272 (7) | 0.0319 (8) | 0.0238 (7) | −0.0081 (6) | −0.0019 (6) | −0.0047 (6) |
S31 | 0.0474 (3) | 0.0316 (2) | 0.0262 (2) | 0.00146 (18) | −0.00544 (18) | −0.00684 (16) |
N32 | 0.0354 (7) | 0.0369 (8) | 0.0229 (7) | −0.0026 (6) | −0.0028 (6) | −0.0055 (6) |
N41 | 0.0302 (7) | 0.0261 (6) | 0.0225 (6) | −0.0041 (5) | −0.0043 (5) | −0.0067 (5) |
C41 | 0.0490 (10) | 0.0265 (8) | 0.0295 (8) | −0.0110 (7) | −0.0111 (7) | −0.0044 (6) |
C42 | 0.0491 (10) | 0.0305 (8) | 0.0287 (8) | −0.0116 (7) | −0.0134 (7) | −0.0066 (7) |
C43 | 0.0288 (7) | 0.0268 (7) | 0.0239 (7) | −0.0023 (6) | −0.0022 (6) | −0.0072 (6) |
C44 | 0.0400 (9) | 0.0251 (8) | 0.0316 (8) | −0.0085 (7) | −0.0052 (7) | −0.0067 (6) |
C45 | 0.0374 (9) | 0.0283 (8) | 0.0294 (8) | −0.0085 (7) | −0.0071 (7) | −0.0076 (6) |
C46 | 0.0312 (8) | 0.0272 (7) | 0.0245 (7) | −0.0063 (6) | −0.0026 (6) | −0.0065 (6) |
S41 | 0.0462 (3) | 0.0309 (2) | 0.0285 (2) | 0.00573 (18) | −0.00729 (18) | −0.01084 (16) |
N42 | 0.0372 (8) | 0.0336 (7) | 0.0243 (7) | 0.0010 (6) | −0.0035 (6) | −0.0081 (6) |
O51 | 0.0771 (11) | 0.0529 (9) | 0.0403 (8) | 0.0034 (8) | −0.0046 (8) | −0.0176 (7) |
C51 | 0.0840 (18) | 0.0442 (12) | 0.0592 (15) | −0.0041 (12) | −0.0121 (13) | −0.0144 (11) |
Geometric parameters (Å, º) top
Co1—N1 | 2.0847 (14) | N22—H21N | 0.8800 |
Co1—N2 | 2.0865 (14) | N22—H22N | 0.8800 |
Co1—N21 | 2.1608 (13) | N31—C31 | 1.335 (2) |
Co1—N31 | 2.1783 (12) | N31—C35 | 1.342 (2) |
Co1—N41 | 2.1792 (13) | C31—C32 | 1.382 (2) |
Co1—N11 | 2.1933 (14) | C31—H31 | 0.9500 |
N1—C1 | 1.164 (2) | C32—C33 | 1.384 (2) |
C1—S1 | 1.6300 (18) | C32—H32 | 0.9500 |
N2—C2 | 1.157 (2) | C33—C34 | 1.386 (2) |
C2—S2 | 1.6381 (18) | C33—C36 | 1.495 (2) |
N11—C11 | 1.336 (2) | C34—C35 | 1.384 (2) |
N11—C15 | 1.343 (2) | C34—H34 | 0.9500 |
C11—C12 | 1.384 (2) | C35—H35 | 0.9500 |
C11—H11 | 0.9500 | C36—N32 | 1.323 (2) |
C12—C13 | 1.391 (2) | C36—S31 | 1.6605 (17) |
C12—H12 | 0.9500 | N32—H31N | 0.8800 |
C13—C14 | 1.386 (2) | N32—H32N | 0.8799 |
C13—C16 | 1.489 (2) | N41—C45 | 1.336 (2) |
C14—C15 | 1.377 (2) | N41—C41 | 1.336 (2) |
C14—H14 | 0.9500 | C41—C42 | 1.381 (2) |
C15—H15 | 0.9500 | C41—H41 | 0.9500 |
C16—N12 | 1.314 (2) | C42—C43 | 1.379 (2) |
C16—S11 | 1.6594 (18) | C42—H42 | 0.9500 |
N12—H11N | 0.8799 | C43—C44 | 1.389 (2) |
N12—H12N | 0.8800 | C43—C46 | 1.495 (2) |
N21—C21 | 1.338 (2) | C44—C45 | 1.380 (2) |
N21—C25 | 1.346 (2) | C44—H44 | 0.9500 |
C21—C22 | 1.383 (2) | C45—H45 | 0.9500 |
C21—H21 | 0.9500 | C46—N42 | 1.314 (2) |
C22—C23 | 1.388 (2) | C46—S41 | 1.6690 (17) |
C22—H22 | 0.9500 | N42—H41N | 0.8800 |
C23—C24 | 1.386 (2) | N42—H42N | 0.8800 |
C23—C26 | 1.496 (2) | O51—C51 | 1.408 (3) |
C24—C25 | 1.380 (2) | O51—H51 | 0.8400 |
C24—H24 | 0.9500 | C51—H51A | 0.9800 |
C25—H25 | 0.9500 | C51—H51B | 0.9800 |
C26—N22 | 1.326 (2) | C51—H51C | 0.9800 |
C26—S21 | 1.6572 (18) | | |
| | | |
N1—Co1—N2 | 176.11 (6) | N22—C26—C23 | 115.73 (15) |
N1—Co1—N21 | 92.32 (5) | N22—C26—S21 | 124.05 (14) |
N2—Co1—N21 | 91.06 (5) | C23—C26—S21 | 120.11 (12) |
N1—Co1—N31 | 91.36 (5) | C26—N22—H21N | 115.1 |
N2—Co1—N31 | 90.73 (5) | C26—N22—H22N | 121.5 |
N21—Co1—N31 | 87.09 (5) | H21N—N22—H22N | 123.0 |
N1—Co1—N41 | 89.20 (5) | C31—N31—C35 | 117.36 (13) |
N2—Co1—N41 | 88.87 (5) | C31—N31—Co1 | 119.81 (10) |
N21—Co1—N41 | 90.24 (5) | C35—N31—Co1 | 122.41 (11) |
N31—Co1—N41 | 177.29 (5) | N31—C31—C32 | 123.04 (15) |
N1—Co1—N11 | 87.53 (6) | N31—C31—H31 | 118.5 |
N2—Co1—N11 | 89.35 (5) | C32—C31—H31 | 118.5 |
N21—Co1—N11 | 172.94 (5) | C31—C32—C33 | 119.40 (16) |
N31—Co1—N11 | 85.85 (5) | C31—C32—H32 | 120.3 |
N41—Co1—N11 | 96.82 (5) | C33—C32—H32 | 120.3 |
C1—N1—Co1 | 163.69 (14) | C32—C33—C34 | 118.04 (14) |
N1—C1—S1 | 178.93 (16) | C32—C33—C36 | 120.67 (15) |
C2—N2—Co1 | 171.72 (14) | C34—C33—C36 | 121.28 (14) |
N2—C2—S2 | 178.71 (16) | C35—C34—C33 | 118.87 (15) |
C11—N11—C15 | 116.99 (14) | C35—C34—H34 | 120.6 |
C11—N11—Co1 | 123.49 (11) | C33—C34—H34 | 120.6 |
C15—N11—Co1 | 118.44 (11) | N31—C35—C34 | 123.21 (15) |
N11—C11—C12 | 123.40 (15) | N31—C35—H35 | 118.4 |
N11—C11—H11 | 118.3 | C34—C35—H35 | 118.4 |
C12—C11—H11 | 118.3 | N32—C36—C33 | 114.27 (15) |
C11—C12—C13 | 119.03 (16) | N32—C36—S31 | 124.92 (12) |
C11—C12—H12 | 120.5 | C33—C36—S31 | 120.80 (12) |
C13—C12—H12 | 120.5 | C36—N32—H31N | 124.0 |
C14—C13—C12 | 117.78 (15) | C36—N32—H32N | 120.1 |
C14—C13—C16 | 121.00 (15) | H31N—N32—H32N | 114.8 |
C12—C13—C16 | 121.22 (15) | C45—N41—C41 | 117.06 (14) |
C15—C14—C13 | 119.26 (15) | C45—N41—Co1 | 120.25 (10) |
C15—C14—H14 | 120.4 | C41—N41—Co1 | 122.68 (11) |
C13—C14—H14 | 120.4 | N41—C41—C42 | 123.16 (16) |
N11—C15—C14 | 123.42 (16) | N41—C41—H41 | 118.4 |
N11—C15—H15 | 118.3 | C42—C41—H41 | 118.4 |
C14—C15—H15 | 118.3 | C43—C42—C41 | 119.50 (15) |
N12—C16—C13 | 115.95 (15) | C43—C42—H42 | 120.2 |
N12—C16—S11 | 123.07 (14) | C41—C42—H42 | 120.2 |
C13—C16—S11 | 120.95 (13) | C42—C43—C44 | 117.72 (14) |
C16—N12—H11N | 120.2 | C42—C43—C46 | 120.89 (14) |
C16—N12—H12N | 123.4 | C44—C43—C46 | 121.37 (14) |
H11N—N12—H12N | 116.3 | C45—C44—C43 | 119.03 (15) |
C21—N21—C25 | 117.15 (14) | C45—C44—H44 | 120.5 |
C21—N21—Co1 | 120.78 (10) | C43—C44—H44 | 120.5 |
C25—N21—Co1 | 121.75 (11) | N41—C45—C44 | 123.49 (15) |
N21—C21—C22 | 123.32 (14) | N41—C45—H45 | 118.3 |
N21—C21—H21 | 118.3 | C44—C45—H45 | 118.3 |
C22—C21—H21 | 118.3 | N42—C46—C43 | 116.01 (14) |
C21—C22—C23 | 119.39 (15) | N42—C46—S41 | 124.26 (12) |
C21—C22—H22 | 120.3 | C43—C46—S41 | 119.69 (12) |
C23—C22—H22 | 120.3 | C46—N42—H41N | 122.5 |
C24—C23—C22 | 117.47 (15) | C46—N42—H42N | 123.2 |
C24—C23—C26 | 120.86 (15) | H41N—N42—H42N | 114.2 |
C22—C23—C26 | 121.61 (15) | C51—O51—H51 | 109.5 |
C25—C24—C23 | 119.77 (15) | O51—C51—H51A | 109.5 |
C25—C24—H24 | 120.1 | O51—C51—H51B | 109.5 |
C23—C24—H24 | 120.1 | H51A—C51—H51B | 109.5 |
N21—C25—C24 | 122.88 (15) | O51—C51—H51C | 109.5 |
N21—C25—H25 | 118.6 | H51A—C51—H51C | 109.5 |
C24—C25—H25 | 118.6 | H51B—C51—H51C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H11N···S2i | 0.88 | 2.45 | 3.3010 (16) | 163 |
N12—H12N···S41ii | 0.88 | 2.64 | 3.3589 (16) | 140 |
C21—H21···S2iii | 0.95 | 2.89 | 3.7626 (16) | 153 |
N22—H21N···S31iv | 0.88 | 2.69 | 3.4969 (17) | 152 |
N22—H22N···S11iv | 0.88 | 2.71 | 3.5691 (17) | 166 |
C31—H31···N1 | 0.95 | 2.65 | 3.137 (2) | 112 |
C34—H34···S21v | 0.95 | 2.95 | 3.8809 (17) | 165 |
C35—H35···S1vi | 0.95 | 2.85 | 3.6906 (17) | 148 |
C35—H35···N2 | 0.95 | 2.68 | 3.203 (2) | 115 |
N32—H31N···O51 | 0.88 | 1.99 | 2.863 (2) | 173 |
N32—H32N···S41vii | 0.88 | 2.67 | 3.5176 (14) | 163 |
N42—H41N···S1viii | 0.88 | 2.49 | 3.3580 (16) | 171 |
N42—H42N···S31ix | 0.88 | 2.64 | 3.4935 (14) | 165 |
O51—H51···S2v | 0.84 | 2.43 | 3.1994 (17) | 153 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y+1, z; (iii) x+1, y, z; (iv) x+1, y−1, z; (v) −x, −y+1, −z; (vi) x−1, y, z; (vii) x−1, y+1, z−1; (viii) −x+1, −y+1, −z+1; (ix) x+1, y−1, z+1. |