The synthesis and crystal structure of a ZnII complex with a (3,4-dihydronaphthalen-1(2H-ylidene)-N-phenyl-carbamohydrazinothioate ligand is reported. The crystal structure shows DMSO molecules bridging the complex units, building an one-dimensional H-bonded polymer.
Supporting information
CCDC reference: 1056177
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean
(C-C) = 0.004 Å
- Disorder in solvent or counterion
- R factor = 0.042
- wR factor = 0.097
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level C
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors of C41 Check
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of O41 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.3 Note
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 4.740 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 18 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 13 Note
Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report
PLAT300_ALERT_4_G Atom Site Occupancy of >S41 is Constrained at 0.600 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <S41' is Constrained at 0.400 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C42 is Constrained at 0.600 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C42' is Constrained at 0.400 Check
PLAT302_ALERT_4_G Anion/Solvent Disorder ............ Percentage = 50 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
6 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
7 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-RED32 (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013-2(Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Bis[
N-phenyl-2-(1,2,3,4-tetrahydronaphthalen-1-ylidene)hydrazinecarbothioamidato-
κ2N2,
S]zinc dimethyl
sulfoxide monosolvate
top
Crystal data top
[Zn(C17H16N3S)2]·C2H6OS | F(000) = 1528 |
Mr = 732.27 | Dx = 1.369 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6320 (4) Å | θ = 1.6–26.0° |
b = 17.2695 (5) Å | µ = 0.91 mm−1 |
c = 19.4067 (7) Å | T = 200 K |
β = 94.223 (3)° | Prism, orange |
V = 3553.6 (2) Å3 | 0.14 × 0.10 × 0.06 mm |
Z = 4 | |
Data collection top
STOE IPDS-1 diffractometer | 6947 independent reflections |
Radiation source: fine-focus sealed tube, STOE IPDS-1 | 6171 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ scans | θmax = 26.0°, θmin = 1.6° |
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008) | h = −13→13 |
Tmin = 0.793, Tmax = 0.916 | k = −21→21 |
45253 measured reflections | l = −23→23 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0382P)2 + 2.9458P] where P = (Fo2 + 2Fc2)/3 |
6947 reflections | (Δ/σ)max = 0.001 |
442 parameters | Δρmax = 0.80 e Å−3 |
0 restraints | Δρmin = −0.68 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Zn1 | 0.75764 (2) | 0.193873 (16) | 0.627860 (14) | 0.03590 (9) | |
C1 | 0.7188 (2) | 0.31745 (15) | 0.73748 (13) | 0.0415 (5) | |
C2 | 0.6288 (3) | 0.36245 (17) | 0.77834 (15) | 0.0518 (7) | |
H2A | 0.6079 | 0.3311 | 0.8186 | 0.062* | |
H2B | 0.5497 | 0.3711 | 0.7491 | 0.062* | |
C3 | 0.6803 (3) | 0.44078 (18) | 0.80402 (17) | 0.0635 (8) | |
H3A | 0.6101 | 0.4736 | 0.8177 | 0.076* | |
H3B | 0.7399 | 0.4331 | 0.8451 | 0.076* | |
C4 | 0.7473 (3) | 0.48091 (18) | 0.74761 (18) | 0.0633 (8) | |
H4A | 0.6883 | 0.4883 | 0.7062 | 0.076* | |
H4B | 0.7777 | 0.5324 | 0.7638 | 0.076* | |
C5 | 0.8570 (3) | 0.43171 (18) | 0.72969 (15) | 0.0555 (7) | |
C6 | 0.9733 (3) | 0.4637 (2) | 0.71835 (19) | 0.0716 (10) | |
H6 | 0.9831 | 0.5184 | 0.7190 | 0.086* | |
C7 | 1.0752 (3) | 0.4175 (2) | 0.7061 (2) | 0.0784 (11) | |
H7 | 1.1535 | 0.4406 | 0.6973 | 0.094* | |
C8 | 1.0638 (3) | 0.3377 (2) | 0.70660 (18) | 0.0684 (9) | |
H8 | 1.1345 | 0.3059 | 0.6994 | 0.082* | |
C9 | 0.9483 (3) | 0.30455 (18) | 0.71767 (15) | 0.0524 (7) | |
H9 | 0.9404 | 0.2498 | 0.7186 | 0.063* | |
C10 | 0.8434 (2) | 0.35090 (16) | 0.72747 (14) | 0.0467 (6) | |
N1 | 0.68571 (18) | 0.25148 (12) | 0.70903 (10) | 0.0374 (4) | |
N2 | 0.56703 (18) | 0.22579 (12) | 0.72604 (10) | 0.0390 (4) | |
C11 | 0.5176 (2) | 0.16915 (14) | 0.68884 (12) | 0.0365 (5) | |
S1 | 0.58047 (6) | 0.11959 (4) | 0.62029 (3) | 0.04070 (15) | |
N3 | 0.40074 (18) | 0.14264 (13) | 0.70263 (11) | 0.0407 (5) | |
H3N | 0.3667 | 0.1097 | 0.6721 | 0.049* | |
C12 | 0.3262 (2) | 0.15955 (15) | 0.75765 (13) | 0.0399 (5) | |
C13 | 0.2066 (2) | 0.12656 (17) | 0.75371 (14) | 0.0493 (6) | |
H13 | 0.1790 | 0.0964 | 0.7146 | 0.059* | |
C14 | 0.1274 (3) | 0.1373 (2) | 0.80637 (16) | 0.0582 (8) | |
H14 | 0.0455 | 0.1150 | 0.8027 | 0.070* | |
C15 | 0.1657 (3) | 0.1799 (2) | 0.86376 (15) | 0.0580 (8) | |
H15 | 0.1117 | 0.1865 | 0.9002 | 0.070* | |
C16 | 0.2836 (3) | 0.2128 (2) | 0.86770 (15) | 0.0577 (8) | |
H16 | 0.3107 | 0.2425 | 0.9073 | 0.069* | |
C17 | 0.3644 (2) | 0.20369 (18) | 0.81488 (14) | 0.0508 (7) | |
H17 | 0.4450 | 0.2276 | 0.8182 | 0.061* | |
C21 | 0.7844 (2) | 0.34196 (15) | 0.54269 (13) | 0.0408 (5) | |
C22 | 0.8717 (3) | 0.39974 (16) | 0.51388 (18) | 0.0555 (7) | |
H22A | 0.9047 | 0.3781 | 0.4716 | 0.067* | |
H22B | 0.9442 | 0.4084 | 0.5480 | 0.067* | |
C23 | 0.8086 (3) | 0.47694 (18) | 0.4965 (2) | 0.0655 (9) | |
H23A | 0.8736 | 0.5160 | 0.4876 | 0.079* | |
H23B | 0.7518 | 0.4715 | 0.4540 | 0.079* | |
C24 | 0.7336 (3) | 0.50397 (18) | 0.55528 (19) | 0.0675 (9) | |
H24A | 0.7906 | 0.5108 | 0.5975 | 0.081* | |
H24B | 0.6939 | 0.5546 | 0.5434 | 0.081* | |
C25 | 0.6338 (3) | 0.44571 (17) | 0.56840 (15) | 0.0532 (7) | |
C26 | 0.5159 (3) | 0.4675 (2) | 0.58907 (18) | 0.0674 (9) | |
H26 | 0.4992 | 0.5206 | 0.5971 | 0.081* | |
C27 | 0.4235 (3) | 0.4135 (2) | 0.59806 (18) | 0.0718 (10) | |
H27 | 0.3456 | 0.4293 | 0.6146 | 0.086* | |
C28 | 0.4430 (3) | 0.3370 (2) | 0.58337 (17) | 0.0627 (8) | |
H28 | 0.3776 | 0.3002 | 0.5875 | 0.075* | |
C29 | 0.5585 (2) | 0.31397 (17) | 0.56250 (15) | 0.0495 (6) | |
H29 | 0.5712 | 0.2612 | 0.5509 | 0.059* | |
C30 | 0.6571 (2) | 0.36679 (16) | 0.55815 (14) | 0.0440 (6) | |
N21 | 0.82246 (17) | 0.27193 (12) | 0.55813 (10) | 0.0365 (4) | |
N22 | 0.94220 (18) | 0.25641 (12) | 0.53682 (11) | 0.0402 (5) | |
C31 | 0.9966 (2) | 0.19343 (14) | 0.56117 (12) | 0.0370 (5) | |
S21 | 0.93916 (6) | 0.12624 (4) | 0.61853 (3) | 0.04147 (15) | |
N23 | 1.11279 (19) | 0.17498 (13) | 0.53992 (11) | 0.0438 (5) | |
H23N | 1.1506 | 0.1358 | 0.5618 | 0.053* | |
C32 | 1.1814 (2) | 0.20924 (16) | 0.48819 (13) | 0.0434 (6) | |
C33 | 1.2983 (3) | 0.1765 (2) | 0.47906 (17) | 0.0627 (8) | |
H33 | 1.3285 | 0.1346 | 0.5073 | 0.075* | |
C34 | 1.3711 (3) | 0.2057 (2) | 0.4282 (2) | 0.0763 (11) | |
H34 | 1.4511 | 0.1833 | 0.4222 | 0.092* | |
C35 | 1.3300 (3) | 0.2660 (2) | 0.38675 (17) | 0.0636 (8) | |
H35 | 1.3804 | 0.2853 | 0.3521 | 0.076* | |
C36 | 1.2150 (3) | 0.29789 (19) | 0.39610 (15) | 0.0551 (7) | |
H36 | 1.1853 | 0.3396 | 0.3674 | 0.066* | |
C37 | 1.1408 (3) | 0.27054 (18) | 0.44670 (14) | 0.0499 (6) | |
H37 | 1.0616 | 0.2941 | 0.4528 | 0.060* | |
S41 | 0.22794 (16) | −0.03767 (8) | 0.62486 (9) | 0.0732 (4) | 0.60 |
S41' | 0.2187 (2) | −0.01998 (12) | 0.55185 (11) | 0.0653 (5) | 0.40 |
O41 | 0.25110 (17) | 0.04499 (11) | 0.60282 (11) | 0.0521 (5) | |
C41 | 0.1008 (4) | −0.0730 (2) | 0.5786 (3) | 0.0915 (13) | |
H41A | 0.0241 | −0.0510 | 0.5958 | 0.137* | 0.60 |
H41B | 0.0990 | −0.1295 | 0.5831 | 0.137* | 0.60 |
H41C | 0.1051 | −0.0591 | 0.5298 | 0.137* | 0.60 |
H41D | 0.0243 | −0.0413 | 0.5780 | 0.137* | 0.40 |
H41E | 0.1230 | −0.0914 | 0.6257 | 0.137* | 0.40 |
H41F | 0.0857 | −0.1175 | 0.5477 | 0.137* | 0.40 |
C42 | 0.3516 (9) | −0.0914 (6) | 0.5996 (7) | 0.124 (5) | 0.60 |
H42A | 0.4297 | −0.0742 | 0.6249 | 0.186* | 0.60 |
H42B | 0.3586 | −0.0846 | 0.5499 | 0.186* | 0.60 |
H42C | 0.3372 | −0.1462 | 0.6095 | 0.186* | 0.60 |
C42' | 0.3297 (14) | −0.0806 (9) | 0.5512 (7) | 0.099 (5) | 0.40 |
H42D | 0.4055 | −0.0550 | 0.5366 | 0.148* | 0.40 |
H42E | 0.3053 | −0.1226 | 0.5190 | 0.148* | 0.40 |
H42F | 0.3471 | −0.1019 | 0.5978 | 0.148* | 0.40 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.03107 (14) | 0.03978 (16) | 0.03778 (15) | 0.00053 (11) | 0.00889 (10) | −0.00104 (11) |
C1 | 0.0421 (13) | 0.0436 (14) | 0.0397 (13) | −0.0017 (11) | 0.0089 (10) | −0.0057 (11) |
C2 | 0.0520 (15) | 0.0492 (15) | 0.0560 (17) | −0.0006 (13) | 0.0169 (13) | −0.0114 (13) |
C3 | 0.075 (2) | 0.0528 (17) | 0.0647 (19) | −0.0011 (15) | 0.0165 (16) | −0.0208 (15) |
C4 | 0.074 (2) | 0.0467 (16) | 0.070 (2) | −0.0102 (15) | 0.0093 (16) | −0.0144 (14) |
C5 | 0.0604 (17) | 0.0546 (17) | 0.0519 (16) | −0.0159 (14) | 0.0073 (13) | −0.0132 (13) |
C6 | 0.074 (2) | 0.065 (2) | 0.077 (2) | −0.0324 (18) | 0.0117 (18) | −0.0151 (17) |
C7 | 0.059 (2) | 0.093 (3) | 0.084 (3) | −0.037 (2) | 0.0168 (18) | −0.018 (2) |
C8 | 0.0451 (16) | 0.088 (2) | 0.073 (2) | −0.0164 (16) | 0.0134 (15) | −0.0212 (19) |
C9 | 0.0423 (14) | 0.0620 (18) | 0.0538 (16) | −0.0092 (13) | 0.0091 (12) | −0.0149 (14) |
C10 | 0.0465 (14) | 0.0509 (15) | 0.0436 (14) | −0.0117 (12) | 0.0088 (11) | −0.0099 (12) |
N1 | 0.0317 (10) | 0.0431 (11) | 0.0382 (11) | −0.0032 (8) | 0.0080 (8) | −0.0028 (9) |
N2 | 0.0320 (10) | 0.0451 (11) | 0.0409 (11) | −0.0039 (9) | 0.0105 (8) | −0.0023 (9) |
C11 | 0.0306 (11) | 0.0390 (12) | 0.0403 (13) | 0.0008 (9) | 0.0056 (9) | 0.0017 (10) |
S1 | 0.0355 (3) | 0.0431 (3) | 0.0445 (3) | −0.0037 (2) | 0.0101 (2) | −0.0067 (3) |
N3 | 0.0321 (10) | 0.0481 (12) | 0.0426 (11) | −0.0056 (9) | 0.0077 (8) | −0.0052 (9) |
C12 | 0.0324 (12) | 0.0481 (14) | 0.0401 (13) | 0.0029 (10) | 0.0077 (10) | 0.0038 (11) |
C13 | 0.0359 (13) | 0.0656 (18) | 0.0471 (15) | −0.0077 (12) | 0.0076 (11) | −0.0030 (13) |
C14 | 0.0334 (13) | 0.086 (2) | 0.0565 (17) | −0.0080 (14) | 0.0122 (12) | 0.0018 (16) |
C15 | 0.0414 (14) | 0.085 (2) | 0.0495 (16) | 0.0000 (14) | 0.0177 (12) | −0.0010 (15) |
C16 | 0.0495 (15) | 0.080 (2) | 0.0454 (15) | −0.0046 (15) | 0.0145 (12) | −0.0091 (14) |
C17 | 0.0369 (13) | 0.0702 (19) | 0.0466 (15) | −0.0075 (12) | 0.0116 (11) | −0.0066 (13) |
C21 | 0.0384 (13) | 0.0400 (13) | 0.0445 (14) | 0.0022 (10) | 0.0065 (10) | 0.0026 (11) |
C22 | 0.0417 (14) | 0.0459 (15) | 0.080 (2) | −0.0006 (12) | 0.0100 (14) | 0.0135 (14) |
C23 | 0.0528 (17) | 0.0469 (16) | 0.097 (3) | −0.0012 (13) | 0.0082 (17) | 0.0203 (17) |
C24 | 0.072 (2) | 0.0432 (16) | 0.087 (2) | 0.0092 (15) | −0.0019 (18) | 0.0014 (16) |
C25 | 0.0564 (16) | 0.0471 (15) | 0.0562 (17) | 0.0139 (13) | 0.0043 (13) | 0.0021 (13) |
C26 | 0.072 (2) | 0.064 (2) | 0.066 (2) | 0.0321 (17) | 0.0086 (16) | −0.0015 (16) |
C27 | 0.0560 (19) | 0.093 (3) | 0.069 (2) | 0.0343 (19) | 0.0194 (16) | 0.0174 (19) |
C28 | 0.0392 (14) | 0.080 (2) | 0.071 (2) | 0.0158 (14) | 0.0134 (14) | 0.0230 (17) |
C29 | 0.0378 (13) | 0.0543 (16) | 0.0568 (16) | 0.0100 (12) | 0.0077 (12) | 0.0111 (13) |
C30 | 0.0400 (13) | 0.0463 (14) | 0.0461 (14) | 0.0088 (11) | 0.0067 (11) | 0.0040 (11) |
N21 | 0.0307 (9) | 0.0397 (11) | 0.0400 (11) | 0.0036 (8) | 0.0087 (8) | 0.0016 (9) |
N22 | 0.0303 (10) | 0.0461 (12) | 0.0456 (12) | 0.0034 (9) | 0.0115 (8) | 0.0040 (9) |
C31 | 0.0307 (11) | 0.0425 (13) | 0.0384 (12) | 0.0028 (10) | 0.0063 (9) | −0.0032 (10) |
S21 | 0.0358 (3) | 0.0414 (3) | 0.0485 (4) | 0.0060 (2) | 0.0114 (3) | 0.0056 (3) |
N23 | 0.0335 (10) | 0.0502 (12) | 0.0487 (12) | 0.0082 (9) | 0.0098 (9) | 0.0067 (10) |
C32 | 0.0302 (12) | 0.0564 (16) | 0.0447 (14) | −0.0015 (11) | 0.0100 (10) | −0.0048 (12) |
C33 | 0.0385 (14) | 0.083 (2) | 0.068 (2) | 0.0139 (15) | 0.0157 (13) | 0.0114 (17) |
C34 | 0.0399 (16) | 0.109 (3) | 0.084 (2) | 0.0103 (17) | 0.0283 (16) | 0.006 (2) |
C35 | 0.0452 (16) | 0.092 (2) | 0.0559 (18) | −0.0123 (16) | 0.0208 (13) | −0.0027 (17) |
C36 | 0.0493 (15) | 0.0673 (19) | 0.0500 (16) | −0.0089 (14) | 0.0131 (12) | 0.0024 (14) |
C37 | 0.0398 (14) | 0.0617 (17) | 0.0499 (15) | 0.0004 (12) | 0.0142 (11) | 0.0033 (13) |
S41 | 0.0817 (10) | 0.0498 (7) | 0.0839 (10) | −0.0036 (7) | −0.0225 (8) | 0.0050 (7) |
S41' | 0.0815 (14) | 0.0555 (11) | 0.0591 (12) | −0.0035 (10) | 0.0072 (10) | −0.0126 (9) |
O41 | 0.0462 (10) | 0.0444 (10) | 0.0654 (12) | 0.0011 (8) | 0.0033 (9) | −0.0082 (9) |
C41 | 0.071 (2) | 0.068 (2) | 0.135 (4) | −0.0099 (19) | 0.010 (2) | −0.023 (2) |
C42 | 0.067 (4) | 0.062 (5) | 0.238 (14) | 0.028 (4) | −0.021 (8) | −0.031 (8) |
C42' | 0.093 (10) | 0.084 (8) | 0.125 (11) | 0.029 (7) | 0.042 (9) | −0.024 (9) |
Geometric parameters (Å, º) top
Zn1—N1 | 2.057 (2) | C23—H23A | 0.9900 |
Zn1—N21 | 2.064 (2) | C23—H23B | 0.9900 |
Zn1—S21 | 2.2745 (6) | C24—C25 | 1.498 (4) |
Zn1—S1 | 2.2747 (7) | C24—H24A | 0.9900 |
C1—N1 | 1.303 (3) | C24—H24B | 0.9900 |
C1—C10 | 1.471 (3) | C25—C26 | 1.396 (4) |
C1—C2 | 1.503 (3) | C25—C30 | 1.402 (4) |
C2—C3 | 1.529 (4) | C26—C27 | 1.375 (5) |
C2—H2A | 0.9900 | C26—H26 | 0.9500 |
C2—H2B | 0.9900 | C27—C28 | 1.370 (5) |
C3—C4 | 1.517 (4) | C27—H27 | 0.9500 |
C3—H3A | 0.9900 | C28—C29 | 1.380 (4) |
C3—H3B | 0.9900 | C28—H28 | 0.9500 |
C4—C5 | 1.504 (4) | C29—C30 | 1.397 (4) |
C4—H4A | 0.9900 | C29—H29 | 0.9500 |
C4—H4B | 0.9900 | N21—N22 | 1.393 (3) |
C5—C6 | 1.387 (4) | N22—C31 | 1.304 (3) |
C5—C10 | 1.403 (4) | C31—N23 | 1.368 (3) |
C6—C7 | 1.380 (5) | C31—S21 | 1.749 (2) |
C6—H6 | 0.9500 | N23—C32 | 1.414 (3) |
C7—C8 | 1.384 (5) | N23—H23N | 0.8800 |
C7—H7 | 0.9500 | C32—C37 | 1.380 (4) |
C8—C9 | 1.386 (4) | C32—C33 | 1.388 (4) |
C8—H8 | 0.9500 | C33—C34 | 1.392 (4) |
C9—C10 | 1.397 (4) | C33—H33 | 0.9500 |
C9—H9 | 0.9500 | C34—C35 | 1.367 (5) |
N1—N2 | 1.400 (3) | C34—H34 | 0.9500 |
N2—C11 | 1.303 (3) | C35—C36 | 1.365 (4) |
C11—N3 | 1.369 (3) | C35—H35 | 0.9500 |
C11—S1 | 1.755 (2) | C36—C37 | 1.387 (4) |
N3—C12 | 1.407 (3) | C36—H36 | 0.9500 |
N3—H3N | 0.8800 | C37—H37 | 0.9500 |
C12—C17 | 1.383 (4) | S41—O41 | 1.516 (2) |
C12—C13 | 1.390 (3) | S41—C41 | 1.682 (4) |
C13—C14 | 1.383 (4) | S41—C42 | 1.709 (9) |
C13—H13 | 0.9500 | S41'—O41 | 1.518 (3) |
C14—C15 | 1.371 (4) | S41'—C42' | 1.578 (13) |
C14—H14 | 0.9500 | S41'—C41 | 1.666 (4) |
C15—C16 | 1.373 (4) | C41—H41A | 0.9800 |
C15—H15 | 0.9500 | C41—H41B | 0.9800 |
C16—C17 | 1.394 (4) | C41—H41C | 0.9800 |
C16—H16 | 0.9500 | C41—H41D | 0.9800 |
C17—H17 | 0.9500 | C41—H41E | 0.9800 |
C21—N21 | 1.303 (3) | C41—H41F | 0.9800 |
C21—C30 | 1.471 (3) | C42—H42A | 0.9800 |
C21—C22 | 1.499 (4) | C42—H42B | 0.9800 |
C22—C23 | 1.519 (4) | C42—H42C | 0.9800 |
C22—H22A | 0.9900 | C42'—H42D | 0.9800 |
C22—H22B | 0.9900 | C42'—H42E | 0.9800 |
C23—C24 | 1.513 (5) | C42'—H42F | 0.9800 |
| | | |
N1—Zn1—N21 | 110.30 (8) | H24A—C24—H24B | 108.2 |
N1—Zn1—S21 | 132.43 (6) | C26—C25—C30 | 118.3 (3) |
N21—Zn1—S21 | 87.53 (5) | C26—C25—C24 | 122.0 (3) |
N1—Zn1—S1 | 88.25 (6) | C30—C25—C24 | 119.6 (3) |
N21—Zn1—S1 | 129.85 (6) | C27—C26—C25 | 121.3 (3) |
S21—Zn1—S1 | 114.13 (3) | C27—C26—H26 | 119.4 |
N1—C1—C10 | 120.3 (2) | C25—C26—H26 | 119.4 |
N1—C1—C2 | 120.9 (2) | C28—C27—C26 | 120.4 (3) |
C10—C1—C2 | 118.7 (2) | C28—C27—H27 | 119.8 |
C1—C2—C3 | 113.8 (2) | C26—C27—H27 | 119.8 |
C1—C2—H2A | 108.8 | C27—C28—C29 | 119.4 (3) |
C3—C2—H2A | 108.8 | C27—C28—H28 | 120.3 |
C1—C2—H2B | 108.8 | C29—C28—H28 | 120.3 |
C3—C2—H2B | 108.8 | C28—C29—C30 | 121.2 (3) |
H2A—C2—H2B | 107.7 | C28—C29—H29 | 119.4 |
C4—C3—C2 | 110.2 (2) | C30—C29—H29 | 119.4 |
C4—C3—H3A | 109.6 | C29—C30—C25 | 119.0 (2) |
C2—C3—H3A | 109.6 | C29—C30—C21 | 121.9 (2) |
C4—C3—H3B | 109.6 | C25—C30—C21 | 119.1 (2) |
C2—C3—H3B | 109.6 | C21—N21—N22 | 112.67 (19) |
H3A—C3—H3B | 108.1 | C21—N21—Zn1 | 130.06 (16) |
C5—C4—C3 | 108.8 (3) | N22—N21—Zn1 | 115.18 (14) |
C5—C4—H4A | 109.9 | C31—N22—N21 | 116.34 (19) |
C3—C4—H4A | 109.9 | N22—C31—N23 | 118.1 (2) |
C5—C4—H4B | 109.9 | N22—C31—S21 | 128.12 (18) |
C3—C4—H4B | 109.9 | N23—C31—S21 | 113.76 (18) |
H4A—C4—H4B | 108.3 | C31—S21—Zn1 | 92.77 (8) |
C6—C5—C10 | 118.9 (3) | C31—N23—C32 | 129.9 (2) |
C6—C5—C4 | 121.8 (3) | C31—N23—H23N | 115.1 |
C10—C5—C4 | 119.2 (3) | C32—N23—H23N | 115.1 |
C7—C6—C5 | 121.1 (3) | C37—C32—C33 | 118.8 (2) |
C7—C6—H6 | 119.4 | C37—C32—N23 | 125.4 (2) |
C5—C6—H6 | 119.4 | C33—C32—N23 | 115.7 (3) |
C6—C7—C8 | 120.3 (3) | C32—C33—C34 | 119.5 (3) |
C6—C7—H7 | 119.9 | C32—C33—H33 | 120.3 |
C8—C7—H7 | 119.9 | C34—C33—H33 | 120.3 |
C7—C8—C9 | 119.5 (3) | C35—C34—C33 | 121.5 (3) |
C7—C8—H8 | 120.3 | C35—C34—H34 | 119.2 |
C9—C8—H8 | 120.3 | C33—C34—H34 | 119.2 |
C8—C9—C10 | 120.6 (3) | C36—C35—C34 | 118.6 (3) |
C8—C9—H9 | 119.7 | C36—C35—H35 | 120.7 |
C10—C9—H9 | 119.7 | C34—C35—H35 | 120.7 |
C9—C10—C5 | 119.5 (3) | C35—C36—C37 | 121.2 (3) |
C9—C10—C1 | 121.9 (3) | C35—C36—H36 | 119.4 |
C5—C10—C1 | 118.6 (3) | C37—C36—H36 | 119.4 |
C1—N1—N2 | 113.40 (19) | C32—C37—C36 | 120.3 (3) |
C1—N1—Zn1 | 130.03 (16) | C32—C37—H37 | 119.9 |
N2—N1—Zn1 | 114.81 (14) | C36—C37—H37 | 119.9 |
C11—N2—N1 | 116.18 (19) | O41—S41—C41 | 109.37 (19) |
N2—C11—N3 | 118.5 (2) | O41—S41—C42 | 106.6 (4) |
N2—C11—S1 | 128.70 (18) | C41—S41—C42 | 104.8 (4) |
N3—C11—S1 | 112.77 (18) | O41—S41'—C42' | 111.2 (6) |
C11—S1—Zn1 | 92.06 (8) | O41—S41'—C41 | 110.1 (2) |
C11—N3—C12 | 130.5 (2) | C42'—S41'—C41 | 102.6 (7) |
C11—N3—H3N | 114.8 | S41—O41—S41' | 56.91 (12) |
C12—N3—H3N | 114.8 | S41'—C41—S41 | 51.17 (14) |
C17—C12—C13 | 118.9 (2) | S41'—C41—H41A | 123.9 |
C17—C12—N3 | 125.1 (2) | S41—C41—H41A | 109.5 |
C13—C12—N3 | 115.9 (2) | S41'—C41—H41B | 126.5 |
C14—C13—C12 | 120.5 (3) | S41—C41—H41B | 109.5 |
C14—C13—H13 | 119.7 | H41A—C41—H41B | 109.5 |
C12—C13—H13 | 119.7 | S41'—C41—H41C | 58.3 |
C15—C14—C13 | 120.8 (3) | S41—C41—H41C | 109.5 |
C15—C14—H14 | 119.6 | H41A—C41—H41C | 109.5 |
C13—C14—H14 | 119.6 | H41B—C41—H41C | 109.5 |
C14—C15—C16 | 118.9 (3) | S41'—C41—H41D | 109.5 |
C14—C15—H15 | 120.6 | S41—C41—H41D | 115.9 |
C16—C15—H15 | 120.6 | H41B—C41—H41D | 122.4 |
C15—C16—C17 | 121.4 (3) | H41C—C41—H41D | 87.2 |
C15—C16—H16 | 119.3 | S41'—C41—H41E | 109.5 |
C17—C16—H16 | 119.3 | S41—C41—H41E | 59.4 |
C12—C17—C16 | 119.5 (3) | H41A—C41—H41E | 87.5 |
C12—C17—H17 | 120.2 | H41B—C41—H41E | 66.3 |
C16—C17—H17 | 120.2 | H41C—C41—H41E | 162.6 |
N21—C21—C30 | 119.9 (2) | H41D—C41—H41E | 109.5 |
N21—C21—C22 | 120.9 (2) | S41'—C41—H41F | 109.5 |
C30—C21—C22 | 119.1 (2) | S41—C41—H41F | 134.4 |
C21—C22—C23 | 113.1 (2) | H41A—C41—H41F | 114.2 |
C21—C22—H22A | 109.0 | H41C—C41—H41F | 67.7 |
C23—C22—H22A | 109.0 | H41D—C41—H41F | 109.5 |
C21—C22—H22B | 109.0 | H41E—C41—H41F | 109.5 |
C23—C22—H22B | 109.0 | S41—C42—H42A | 109.5 |
H22A—C22—H22B | 107.8 | S41—C42—H42B | 109.5 |
C24—C23—C22 | 110.6 (3) | H42A—C42—H42B | 109.5 |
C24—C23—H23A | 109.5 | S41—C42—H42C | 109.5 |
C22—C23—H23A | 109.5 | H42A—C42—H42C | 109.5 |
C24—C23—H23B | 109.5 | H42B—C42—H42C | 109.5 |
C22—C23—H23B | 109.5 | S41'—C42'—H42D | 109.5 |
H23A—C23—H23B | 108.1 | S41'—C42'—H42E | 109.5 |
C25—C24—C23 | 109.9 (3) | H42D—C42'—H42E | 109.5 |
C25—C24—H24A | 109.7 | S41'—C42'—H42F | 109.5 |
C23—C24—H24A | 109.7 | H42D—C42'—H42F | 109.5 |
C25—C24—H24B | 109.7 | H42E—C42'—H42F | 109.5 |
C23—C24—H24B | 109.7 | | |
| | | |
N1—C1—C2—C3 | −176.3 (3) | C23—C24—C25—C30 | 33.3 (4) |
C10—C1—C2—C3 | 1.0 (4) | C30—C25—C26—C27 | −1.2 (5) |
C1—C2—C3—C4 | 42.4 (4) | C24—C25—C26—C27 | 177.2 (3) |
C2—C3—C4—C5 | −61.7 (4) | C25—C26—C27—C28 | −3.4 (5) |
C3—C4—C5—C6 | −138.1 (3) | C26—C27—C28—C29 | 3.0 (5) |
C3—C4—C5—C10 | 38.9 (4) | C27—C28—C29—C30 | 2.0 (5) |
C10—C5—C6—C7 | −1.0 (5) | C28—C29—C30—C25 | −6.6 (4) |
C4—C5—C6—C7 | 176.0 (3) | C28—C29—C30—C21 | 173.8 (3) |
C5—C6—C7—C8 | −1.6 (6) | C26—C25—C30—C29 | 6.0 (4) |
C6—C7—C8—C9 | 1.7 (6) | C24—C25—C30—C29 | −172.4 (3) |
C7—C8—C9—C10 | 0.8 (5) | C26—C25—C30—C21 | −174.3 (3) |
C8—C9—C10—C5 | −3.4 (4) | C24—C25—C30—C21 | 7.2 (4) |
C8—C9—C10—C1 | 178.3 (3) | N21—C21—C30—C29 | −26.2 (4) |
C6—C5—C10—C9 | 3.4 (4) | C22—C21—C30—C29 | 158.1 (3) |
C4—C5—C10—C9 | −173.7 (3) | N21—C21—C30—C25 | 154.2 (3) |
C6—C5—C10—C1 | −178.2 (3) | C22—C21—C30—C25 | −21.5 (4) |
C4—C5—C10—C1 | 4.7 (4) | C30—C21—N21—N22 | 176.8 (2) |
N1—C1—C10—C9 | −30.4 (4) | C22—C21—N21—N22 | −7.6 (3) |
C2—C1—C10—C9 | 152.3 (3) | C30—C21—N21—Zn1 | −20.7 (4) |
N1—C1—C10—C5 | 151.3 (3) | C22—C21—N21—Zn1 | 154.9 (2) |
C2—C1—C10—C5 | −26.0 (4) | N1—Zn1—N21—C21 | −29.8 (2) |
C10—C1—N1—N2 | 177.2 (2) | S21—Zn1—N21—C21 | −164.6 (2) |
C2—C1—N1—N2 | −5.6 (3) | S1—Zn1—N21—C21 | 75.6 (2) |
C10—C1—N1—Zn1 | −18.9 (4) | N1—Zn1—N21—N22 | 132.36 (16) |
C2—C1—N1—Zn1 | 158.3 (2) | S21—Zn1—N21—N22 | −2.39 (15) |
N21—Zn1—N1—C1 | −32.0 (2) | S1—Zn1—N21—N22 | −122.19 (14) |
S21—Zn1—N1—C1 | 74.0 (2) | C21—N21—N22—C31 | 167.8 (2) |
S1—Zn1—N1—C1 | −164.2 (2) | Zn1—N21—N22—C31 | 2.5 (3) |
N21—Zn1—N1—N2 | 131.70 (16) | N21—N22—C31—N23 | 178.2 (2) |
S21—Zn1—N1—N2 | −122.29 (14) | N21—N22—C31—S21 | −1.0 (3) |
S1—Zn1—N1—N2 | −0.55 (15) | N22—C31—S21—Zn1 | −0.7 (2) |
C1—N1—N2—C11 | 166.6 (2) | N23—C31—S21—Zn1 | −179.98 (18) |
Zn1—N1—N2—C11 | 0.1 (3) | N1—Zn1—S21—C31 | −114.08 (11) |
N1—N2—C11—N3 | −179.0 (2) | N21—Zn1—S21—C31 | 1.45 (10) |
N1—N2—C11—S1 | 0.7 (3) | S1—Zn1—S21—C31 | 134.57 (8) |
N2—C11—S1—Zn1 | −0.9 (2) | N22—C31—N23—C32 | −8.0 (4) |
N3—C11—S1—Zn1 | 178.75 (17) | S21—C31—N23—C32 | 171.3 (2) |
N1—Zn1—S1—C11 | 0.64 (10) | C31—N23—C32—C37 | −0.9 (5) |
N21—Zn1—S1—C11 | −114.62 (11) | C31—N23—C32—C33 | 180.0 (3) |
S21—Zn1—S1—C11 | 137.18 (8) | C37—C32—C33—C34 | −0.5 (5) |
N2—C11—N3—C12 | −9.2 (4) | N23—C32—C33—C34 | 178.7 (3) |
S1—C11—N3—C12 | 171.1 (2) | C32—C33—C34—C35 | −0.1 (6) |
C11—N3—C12—C17 | −6.5 (4) | C33—C34—C35—C36 | 0.2 (6) |
C11—N3—C12—C13 | 175.6 (3) | C34—C35—C36—C37 | 0.3 (5) |
C17—C12—C13—C14 | −0.4 (4) | C33—C32—C37—C36 | 1.0 (4) |
N3—C12—C13—C14 | 177.7 (3) | N23—C32—C37—C36 | −178.1 (3) |
C12—C13—C14—C15 | −0.8 (5) | C35—C36—C37—C32 | −1.0 (5) |
C13—C14—C15—C16 | 1.0 (5) | O41—S41—O41—S41' | 0 (47) |
C14—C15—C16—C17 | −0.1 (5) | C41—S41—O41—S41' | −43.9 (2) |
C13—C12—C17—C16 | 1.3 (4) | C42—S41—O41—S41' | 68.9 (4) |
N3—C12—C17—C16 | −176.6 (3) | O41—S41'—O41—S41 | 0 (58) |
C15—C16—C17—C12 | −1.0 (5) | C42'—S41'—O41—S41 | −68.3 (6) |
N21—C21—C22—C23 | 177.7 (3) | C41—S41'—O41—S41 | 44.7 (2) |
C30—C21—C22—C23 | −6.7 (4) | O41—S41'—C41—S41 | −42.94 (17) |
C21—C22—C23—C24 | 46.8 (4) | C42'—S41'—C41—S41 | 75.5 (6) |
C22—C23—C24—C25 | −60.0 (4) | O41—S41—C41—S41' | 42.81 (18) |
C23—C24—C25—C26 | −145.1 (3) | C42—S41—C41—S41' | −71.1 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O41 | 0.88 | 2.08 | 2.945 (3) | 168 |
N23—H23N···O41i | 0.88 | 2.03 | 2.903 (3) | 173 |
Symmetry code: (i) x+1, y, z. |