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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901500612X/im2462sup1.cif
Contains datablocks I, publication_text

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901500612X/im2462Isup2.hkl
Contains datablock I

CCDC reference: 1056177

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](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

Computing details top

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]·C2H6OSF(000) = 1528
Mr = 732.27Dx = 1.369 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.6320 (4) Åθ = 1.6–26.0°
b = 17.2695 (5) ŵ = 0.91 mm1
c = 19.4067 (7) ÅT = 200 K
β = 94.223 (3)°Prism, orange
V = 3553.6 (2) Å30.14 × 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-16171 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ scansθmax = 26.0°, θmin = 1.6°
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie, 2008)
h = 1313
Tmin = 0.793, Tmax = 0.916k = 2121
45253 measured reflectionsl = 2323
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-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 parametersΔρmax = 0.80 e Å3
0 restraintsΔρmin = 0.68 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*/UeqOcc. (<1)
Zn10.75764 (2)0.193873 (16)0.627860 (14)0.03590 (9)
C10.7188 (2)0.31745 (15)0.73748 (13)0.0415 (5)
C20.6288 (3)0.36245 (17)0.77834 (15)0.0518 (7)
H2A0.60790.33110.81860.062*
H2B0.54970.37110.74910.062*
C30.6803 (3)0.44078 (18)0.80402 (17)0.0635 (8)
H3A0.61010.47360.81770.076*
H3B0.73990.43310.84510.076*
C40.7473 (3)0.48091 (18)0.74761 (18)0.0633 (8)
H4A0.68830.48830.70620.076*
H4B0.77770.53240.76380.076*
C50.8570 (3)0.43171 (18)0.72969 (15)0.0555 (7)
C60.9733 (3)0.4637 (2)0.71835 (19)0.0716 (10)
H60.98310.51840.71900.086*
C71.0752 (3)0.4175 (2)0.7061 (2)0.0784 (11)
H71.15350.44060.69730.094*
C81.0638 (3)0.3377 (2)0.70660 (18)0.0684 (9)
H81.13450.30590.69940.082*
C90.9483 (3)0.30455 (18)0.71767 (15)0.0524 (7)
H90.94040.24980.71860.063*
C100.8434 (2)0.35090 (16)0.72747 (14)0.0467 (6)
N10.68571 (18)0.25148 (12)0.70903 (10)0.0374 (4)
N20.56703 (18)0.22579 (12)0.72604 (10)0.0390 (4)
C110.5176 (2)0.16915 (14)0.68884 (12)0.0365 (5)
S10.58047 (6)0.11959 (4)0.62029 (3)0.04070 (15)
N30.40074 (18)0.14264 (13)0.70263 (11)0.0407 (5)
H3N0.36670.10970.67210.049*
C120.3262 (2)0.15955 (15)0.75765 (13)0.0399 (5)
C130.2066 (2)0.12656 (17)0.75371 (14)0.0493 (6)
H130.17900.09640.71460.059*
C140.1274 (3)0.1373 (2)0.80637 (16)0.0582 (8)
H140.04550.11500.80270.070*
C150.1657 (3)0.1799 (2)0.86376 (15)0.0580 (8)
H150.11170.18650.90020.070*
C160.2836 (3)0.2128 (2)0.86770 (15)0.0577 (8)
H160.31070.24250.90730.069*
C170.3644 (2)0.20369 (18)0.81488 (14)0.0508 (7)
H170.44500.22760.81820.061*
C210.7844 (2)0.34196 (15)0.54269 (13)0.0408 (5)
C220.8717 (3)0.39974 (16)0.51388 (18)0.0555 (7)
H22A0.90470.37810.47160.067*
H22B0.94420.40840.54800.067*
C230.8086 (3)0.47694 (18)0.4965 (2)0.0655 (9)
H23A0.87360.51600.48760.079*
H23B0.75180.47150.45400.079*
C240.7336 (3)0.50397 (18)0.55528 (19)0.0675 (9)
H24A0.79060.51080.59750.081*
H24B0.69390.55460.54340.081*
C250.6338 (3)0.44571 (17)0.56840 (15)0.0532 (7)
C260.5159 (3)0.4675 (2)0.58907 (18)0.0674 (9)
H260.49920.52060.59710.081*
C270.4235 (3)0.4135 (2)0.59806 (18)0.0718 (10)
H270.34560.42930.61460.086*
C280.4430 (3)0.3370 (2)0.58337 (17)0.0627 (8)
H280.37760.30020.58750.075*
C290.5585 (2)0.31397 (17)0.56250 (15)0.0495 (6)
H290.57120.26120.55090.059*
C300.6571 (2)0.36679 (16)0.55815 (14)0.0440 (6)
N210.82246 (17)0.27193 (12)0.55813 (10)0.0365 (4)
N220.94220 (18)0.25641 (12)0.53682 (11)0.0402 (5)
C310.9966 (2)0.19343 (14)0.56117 (12)0.0370 (5)
S210.93916 (6)0.12624 (4)0.61853 (3)0.04147 (15)
N231.11279 (19)0.17498 (13)0.53992 (11)0.0438 (5)
H23N1.15060.13580.56180.053*
C321.1814 (2)0.20924 (16)0.48819 (13)0.0434 (6)
C331.2983 (3)0.1765 (2)0.47906 (17)0.0627 (8)
H331.32850.13460.50730.075*
C341.3711 (3)0.2057 (2)0.4282 (2)0.0763 (11)
H341.45110.18330.42220.092*
C351.3300 (3)0.2660 (2)0.38675 (17)0.0636 (8)
H351.38040.28530.35210.076*
C361.2150 (3)0.29789 (19)0.39610 (15)0.0551 (7)
H361.18530.33960.36740.066*
C371.1408 (3)0.27054 (18)0.44670 (14)0.0499 (6)
H371.06160.29410.45280.060*
S410.22794 (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
O410.25110 (17)0.04499 (11)0.60282 (11)0.0521 (5)
C410.1008 (4)0.0730 (2)0.5786 (3)0.0915 (13)
H41A0.02410.05100.59580.137*0.60
H41B0.09900.12950.58310.137*0.60
H41C0.10510.05910.52980.137*0.60
H41D0.02430.04130.57800.137*0.40
H41E0.12300.09140.62570.137*0.40
H41F0.08570.11750.54770.137*0.40
C420.3516 (9)0.0914 (6)0.5996 (7)0.124 (5)0.60
H42A0.42970.07420.62490.186*0.60
H42B0.35860.08460.54990.186*0.60
H42C0.33720.14620.60950.186*0.60
C42'0.3297 (14)0.0806 (9)0.5512 (7)0.099 (5)0.40
H42D0.40550.05500.53660.148*0.40
H42E0.30530.12260.51900.148*0.40
H42F0.34710.10190.59780.148*0.40
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03107 (14)0.03978 (16)0.03778 (15)0.00053 (11)0.00889 (10)0.00104 (11)
C10.0421 (13)0.0436 (14)0.0397 (13)0.0017 (11)0.0089 (10)0.0057 (11)
C20.0520 (15)0.0492 (15)0.0560 (17)0.0006 (13)0.0169 (13)0.0114 (13)
C30.075 (2)0.0528 (17)0.0647 (19)0.0011 (15)0.0165 (16)0.0208 (15)
C40.074 (2)0.0467 (16)0.070 (2)0.0102 (15)0.0093 (16)0.0144 (14)
C50.0604 (17)0.0546 (17)0.0519 (16)0.0159 (14)0.0073 (13)0.0132 (13)
C60.074 (2)0.065 (2)0.077 (2)0.0324 (18)0.0117 (18)0.0151 (17)
C70.059 (2)0.093 (3)0.084 (3)0.037 (2)0.0168 (18)0.018 (2)
C80.0451 (16)0.088 (2)0.073 (2)0.0164 (16)0.0134 (15)0.0212 (19)
C90.0423 (14)0.0620 (18)0.0538 (16)0.0092 (13)0.0091 (12)0.0149 (14)
C100.0465 (14)0.0509 (15)0.0436 (14)0.0117 (12)0.0088 (11)0.0099 (12)
N10.0317 (10)0.0431 (11)0.0382 (11)0.0032 (8)0.0080 (8)0.0028 (9)
N20.0320 (10)0.0451 (11)0.0409 (11)0.0039 (9)0.0105 (8)0.0023 (9)
C110.0306 (11)0.0390 (12)0.0403 (13)0.0008 (9)0.0056 (9)0.0017 (10)
S10.0355 (3)0.0431 (3)0.0445 (3)0.0037 (2)0.0101 (2)0.0067 (3)
N30.0321 (10)0.0481 (12)0.0426 (11)0.0056 (9)0.0077 (8)0.0052 (9)
C120.0324 (12)0.0481 (14)0.0401 (13)0.0029 (10)0.0077 (10)0.0038 (11)
C130.0359 (13)0.0656 (18)0.0471 (15)0.0077 (12)0.0076 (11)0.0030 (13)
C140.0334 (13)0.086 (2)0.0565 (17)0.0080 (14)0.0122 (12)0.0018 (16)
C150.0414 (14)0.085 (2)0.0495 (16)0.0000 (14)0.0177 (12)0.0010 (15)
C160.0495 (15)0.080 (2)0.0454 (15)0.0046 (15)0.0145 (12)0.0091 (14)
C170.0369 (13)0.0702 (19)0.0466 (15)0.0075 (12)0.0116 (11)0.0066 (13)
C210.0384 (13)0.0400 (13)0.0445 (14)0.0022 (10)0.0065 (10)0.0026 (11)
C220.0417 (14)0.0459 (15)0.080 (2)0.0006 (12)0.0100 (14)0.0135 (14)
C230.0528 (17)0.0469 (16)0.097 (3)0.0012 (13)0.0082 (17)0.0203 (17)
C240.072 (2)0.0432 (16)0.087 (2)0.0092 (15)0.0019 (18)0.0014 (16)
C250.0564 (16)0.0471 (15)0.0562 (17)0.0139 (13)0.0043 (13)0.0021 (13)
C260.072 (2)0.064 (2)0.066 (2)0.0321 (17)0.0086 (16)0.0015 (16)
C270.0560 (19)0.093 (3)0.069 (2)0.0343 (19)0.0194 (16)0.0174 (19)
C280.0392 (14)0.080 (2)0.071 (2)0.0158 (14)0.0134 (14)0.0230 (17)
C290.0378 (13)0.0543 (16)0.0568 (16)0.0100 (12)0.0077 (12)0.0111 (13)
C300.0400 (13)0.0463 (14)0.0461 (14)0.0088 (11)0.0067 (11)0.0040 (11)
N210.0307 (9)0.0397 (11)0.0400 (11)0.0036 (8)0.0087 (8)0.0016 (9)
N220.0303 (10)0.0461 (12)0.0456 (12)0.0034 (9)0.0115 (8)0.0040 (9)
C310.0307 (11)0.0425 (13)0.0384 (12)0.0028 (10)0.0063 (9)0.0032 (10)
S210.0358 (3)0.0414 (3)0.0485 (4)0.0060 (2)0.0114 (3)0.0056 (3)
N230.0335 (10)0.0502 (12)0.0487 (12)0.0082 (9)0.0098 (9)0.0067 (10)
C320.0302 (12)0.0564 (16)0.0447 (14)0.0015 (11)0.0100 (10)0.0048 (12)
C330.0385 (14)0.083 (2)0.068 (2)0.0139 (15)0.0157 (13)0.0114 (17)
C340.0399 (16)0.109 (3)0.084 (2)0.0103 (17)0.0283 (16)0.006 (2)
C350.0452 (16)0.092 (2)0.0559 (18)0.0123 (16)0.0208 (13)0.0027 (17)
C360.0493 (15)0.0673 (19)0.0500 (16)0.0089 (14)0.0131 (12)0.0024 (14)
C370.0398 (14)0.0617 (17)0.0499 (15)0.0004 (12)0.0142 (11)0.0033 (13)
S410.0817 (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)
O410.0462 (10)0.0444 (10)0.0654 (12)0.0011 (8)0.0033 (9)0.0082 (9)
C410.071 (2)0.068 (2)0.135 (4)0.0099 (19)0.010 (2)0.023 (2)
C420.067 (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—N12.057 (2)C23—H23A0.9900
Zn1—N212.064 (2)C23—H23B0.9900
Zn1—S212.2745 (6)C24—C251.498 (4)
Zn1—S12.2747 (7)C24—H24A0.9900
C1—N11.303 (3)C24—H24B0.9900
C1—C101.471 (3)C25—C261.396 (4)
C1—C21.503 (3)C25—C301.402 (4)
C2—C31.529 (4)C26—C271.375 (5)
C2—H2A0.9900C26—H260.9500
C2—H2B0.9900C27—C281.370 (5)
C3—C41.517 (4)C27—H270.9500
C3—H3A0.9900C28—C291.380 (4)
C3—H3B0.9900C28—H280.9500
C4—C51.504 (4)C29—C301.397 (4)
C4—H4A0.9900C29—H290.9500
C4—H4B0.9900N21—N221.393 (3)
C5—C61.387 (4)N22—C311.304 (3)
C5—C101.403 (4)C31—N231.368 (3)
C6—C71.380 (5)C31—S211.749 (2)
C6—H60.9500N23—C321.414 (3)
C7—C81.384 (5)N23—H23N0.8800
C7—H70.9500C32—C371.380 (4)
C8—C91.386 (4)C32—C331.388 (4)
C8—H80.9500C33—C341.392 (4)
C9—C101.397 (4)C33—H330.9500
C9—H90.9500C34—C351.367 (5)
N1—N21.400 (3)C34—H340.9500
N2—C111.303 (3)C35—C361.365 (4)
C11—N31.369 (3)C35—H350.9500
C11—S11.755 (2)C36—C371.387 (4)
N3—C121.407 (3)C36—H360.9500
N3—H3N0.8800C37—H370.9500
C12—C171.383 (4)S41—O411.516 (2)
C12—C131.390 (3)S41—C411.682 (4)
C13—C141.383 (4)S41—C421.709 (9)
C13—H130.9500S41'—O411.518 (3)
C14—C151.371 (4)S41'—C42'1.578 (13)
C14—H140.9500S41'—C411.666 (4)
C15—C161.373 (4)C41—H41A0.9800
C15—H150.9500C41—H41B0.9800
C16—C171.394 (4)C41—H41C0.9800
C16—H160.9500C41—H41D0.9800
C17—H170.9500C41—H41E0.9800
C21—N211.303 (3)C41—H41F0.9800
C21—C301.471 (3)C42—H42A0.9800
C21—C221.499 (4)C42—H42B0.9800
C22—C231.519 (4)C42—H42C0.9800
C22—H22A0.9900C42'—H42D0.9800
C22—H22B0.9900C42'—H42E0.9800
C23—C241.513 (5)C42'—H42F0.9800
N1—Zn1—N21110.30 (8)H24A—C24—H24B108.2
N1—Zn1—S21132.43 (6)C26—C25—C30118.3 (3)
N21—Zn1—S2187.53 (5)C26—C25—C24122.0 (3)
N1—Zn1—S188.25 (6)C30—C25—C24119.6 (3)
N21—Zn1—S1129.85 (6)C27—C26—C25121.3 (3)
S21—Zn1—S1114.13 (3)C27—C26—H26119.4
N1—C1—C10120.3 (2)C25—C26—H26119.4
N1—C1—C2120.9 (2)C28—C27—C26120.4 (3)
C10—C1—C2118.7 (2)C28—C27—H27119.8
C1—C2—C3113.8 (2)C26—C27—H27119.8
C1—C2—H2A108.8C27—C28—C29119.4 (3)
C3—C2—H2A108.8C27—C28—H28120.3
C1—C2—H2B108.8C29—C28—H28120.3
C3—C2—H2B108.8C28—C29—C30121.2 (3)
H2A—C2—H2B107.7C28—C29—H29119.4
C4—C3—C2110.2 (2)C30—C29—H29119.4
C4—C3—H3A109.6C29—C30—C25119.0 (2)
C2—C3—H3A109.6C29—C30—C21121.9 (2)
C4—C3—H3B109.6C25—C30—C21119.1 (2)
C2—C3—H3B109.6C21—N21—N22112.67 (19)
H3A—C3—H3B108.1C21—N21—Zn1130.06 (16)
C5—C4—C3108.8 (3)N22—N21—Zn1115.18 (14)
C5—C4—H4A109.9C31—N22—N21116.34 (19)
C3—C4—H4A109.9N22—C31—N23118.1 (2)
C5—C4—H4B109.9N22—C31—S21128.12 (18)
C3—C4—H4B109.9N23—C31—S21113.76 (18)
H4A—C4—H4B108.3C31—S21—Zn192.77 (8)
C6—C5—C10118.9 (3)C31—N23—C32129.9 (2)
C6—C5—C4121.8 (3)C31—N23—H23N115.1
C10—C5—C4119.2 (3)C32—N23—H23N115.1
C7—C6—C5121.1 (3)C37—C32—C33118.8 (2)
C7—C6—H6119.4C37—C32—N23125.4 (2)
C5—C6—H6119.4C33—C32—N23115.7 (3)
C6—C7—C8120.3 (3)C32—C33—C34119.5 (3)
C6—C7—H7119.9C32—C33—H33120.3
C8—C7—H7119.9C34—C33—H33120.3
C7—C8—C9119.5 (3)C35—C34—C33121.5 (3)
C7—C8—H8120.3C35—C34—H34119.2
C9—C8—H8120.3C33—C34—H34119.2
C8—C9—C10120.6 (3)C36—C35—C34118.6 (3)
C8—C9—H9119.7C36—C35—H35120.7
C10—C9—H9119.7C34—C35—H35120.7
C9—C10—C5119.5 (3)C35—C36—C37121.2 (3)
C9—C10—C1121.9 (3)C35—C36—H36119.4
C5—C10—C1118.6 (3)C37—C36—H36119.4
C1—N1—N2113.40 (19)C32—C37—C36120.3 (3)
C1—N1—Zn1130.03 (16)C32—C37—H37119.9
N2—N1—Zn1114.81 (14)C36—C37—H37119.9
C11—N2—N1116.18 (19)O41—S41—C41109.37 (19)
N2—C11—N3118.5 (2)O41—S41—C42106.6 (4)
N2—C11—S1128.70 (18)C41—S41—C42104.8 (4)
N3—C11—S1112.77 (18)O41—S41'—C42'111.2 (6)
C11—S1—Zn192.06 (8)O41—S41'—C41110.1 (2)
C11—N3—C12130.5 (2)C42'—S41'—C41102.6 (7)
C11—N3—H3N114.8S41—O41—S41'56.91 (12)
C12—N3—H3N114.8S41'—C41—S4151.17 (14)
C17—C12—C13118.9 (2)S41'—C41—H41A123.9
C17—C12—N3125.1 (2)S41—C41—H41A109.5
C13—C12—N3115.9 (2)S41'—C41—H41B126.5
C14—C13—C12120.5 (3)S41—C41—H41B109.5
C14—C13—H13119.7H41A—C41—H41B109.5
C12—C13—H13119.7S41'—C41—H41C58.3
C15—C14—C13120.8 (3)S41—C41—H41C109.5
C15—C14—H14119.6H41A—C41—H41C109.5
C13—C14—H14119.6H41B—C41—H41C109.5
C14—C15—C16118.9 (3)S41'—C41—H41D109.5
C14—C15—H15120.6S41—C41—H41D115.9
C16—C15—H15120.6H41B—C41—H41D122.4
C15—C16—C17121.4 (3)H41C—C41—H41D87.2
C15—C16—H16119.3S41'—C41—H41E109.5
C17—C16—H16119.3S41—C41—H41E59.4
C12—C17—C16119.5 (3)H41A—C41—H41E87.5
C12—C17—H17120.2H41B—C41—H41E66.3
C16—C17—H17120.2H41C—C41—H41E162.6
N21—C21—C30119.9 (2)H41D—C41—H41E109.5
N21—C21—C22120.9 (2)S41'—C41—H41F109.5
C30—C21—C22119.1 (2)S41—C41—H41F134.4
C21—C22—C23113.1 (2)H41A—C41—H41F114.2
C21—C22—H22A109.0H41C—C41—H41F67.7
C23—C22—H22A109.0H41D—C41—H41F109.5
C21—C22—H22B109.0H41E—C41—H41F109.5
C23—C22—H22B109.0S41—C42—H42A109.5
H22A—C22—H22B107.8S41—C42—H42B109.5
C24—C23—C22110.6 (3)H42A—C42—H42B109.5
C24—C23—H23A109.5S41—C42—H42C109.5
C22—C23—H23A109.5H42A—C42—H42C109.5
C24—C23—H23B109.5H42B—C42—H42C109.5
C22—C23—H23B109.5S41'—C42'—H42D109.5
H23A—C23—H23B108.1S41'—C42'—H42E109.5
C25—C24—C23109.9 (3)H42D—C42'—H42E109.5
C25—C24—H24A109.7S41'—C42'—H42F109.5
C23—C24—H24A109.7H42D—C42'—H42F109.5
C25—C24—H24B109.7H42E—C42'—H42F109.5
C23—C24—H24B109.7
N1—C1—C2—C3176.3 (3)C23—C24—C25—C3033.3 (4)
C10—C1—C2—C31.0 (4)C30—C25—C26—C271.2 (5)
C1—C2—C3—C442.4 (4)C24—C25—C26—C27177.2 (3)
C2—C3—C4—C561.7 (4)C25—C26—C27—C283.4 (5)
C3—C4—C5—C6138.1 (3)C26—C27—C28—C293.0 (5)
C3—C4—C5—C1038.9 (4)C27—C28—C29—C302.0 (5)
C10—C5—C6—C71.0 (5)C28—C29—C30—C256.6 (4)
C4—C5—C6—C7176.0 (3)C28—C29—C30—C21173.8 (3)
C5—C6—C7—C81.6 (6)C26—C25—C30—C296.0 (4)
C6—C7—C8—C91.7 (6)C24—C25—C30—C29172.4 (3)
C7—C8—C9—C100.8 (5)C26—C25—C30—C21174.3 (3)
C8—C9—C10—C53.4 (4)C24—C25—C30—C217.2 (4)
C8—C9—C10—C1178.3 (3)N21—C21—C30—C2926.2 (4)
C6—C5—C10—C93.4 (4)C22—C21—C30—C29158.1 (3)
C4—C5—C10—C9173.7 (3)N21—C21—C30—C25154.2 (3)
C6—C5—C10—C1178.2 (3)C22—C21—C30—C2521.5 (4)
C4—C5—C10—C14.7 (4)C30—C21—N21—N22176.8 (2)
N1—C1—C10—C930.4 (4)C22—C21—N21—N227.6 (3)
C2—C1—C10—C9152.3 (3)C30—C21—N21—Zn120.7 (4)
N1—C1—C10—C5151.3 (3)C22—C21—N21—Zn1154.9 (2)
C2—C1—C10—C526.0 (4)N1—Zn1—N21—C2129.8 (2)
C10—C1—N1—N2177.2 (2)S21—Zn1—N21—C21164.6 (2)
C2—C1—N1—N25.6 (3)S1—Zn1—N21—C2175.6 (2)
C10—C1—N1—Zn118.9 (4)N1—Zn1—N21—N22132.36 (16)
C2—C1—N1—Zn1158.3 (2)S21—Zn1—N21—N222.39 (15)
N21—Zn1—N1—C132.0 (2)S1—Zn1—N21—N22122.19 (14)
S21—Zn1—N1—C174.0 (2)C21—N21—N22—C31167.8 (2)
S1—Zn1—N1—C1164.2 (2)Zn1—N21—N22—C312.5 (3)
N21—Zn1—N1—N2131.70 (16)N21—N22—C31—N23178.2 (2)
S21—Zn1—N1—N2122.29 (14)N21—N22—C31—S211.0 (3)
S1—Zn1—N1—N20.55 (15)N22—C31—S21—Zn10.7 (2)
C1—N1—N2—C11166.6 (2)N23—C31—S21—Zn1179.98 (18)
Zn1—N1—N2—C110.1 (3)N1—Zn1—S21—C31114.08 (11)
N1—N2—C11—N3179.0 (2)N21—Zn1—S21—C311.45 (10)
N1—N2—C11—S10.7 (3)S1—Zn1—S21—C31134.57 (8)
N2—C11—S1—Zn10.9 (2)N22—C31—N23—C328.0 (4)
N3—C11—S1—Zn1178.75 (17)S21—C31—N23—C32171.3 (2)
N1—Zn1—S1—C110.64 (10)C31—N23—C32—C370.9 (5)
N21—Zn1—S1—C11114.62 (11)C31—N23—C32—C33180.0 (3)
S21—Zn1—S1—C11137.18 (8)C37—C32—C33—C340.5 (5)
N2—C11—N3—C129.2 (4)N23—C32—C33—C34178.7 (3)
S1—C11—N3—C12171.1 (2)C32—C33—C34—C350.1 (6)
C11—N3—C12—C176.5 (4)C33—C34—C35—C360.2 (6)
C11—N3—C12—C13175.6 (3)C34—C35—C36—C370.3 (5)
C17—C12—C13—C140.4 (4)C33—C32—C37—C361.0 (4)
N3—C12—C13—C14177.7 (3)N23—C32—C37—C36178.1 (3)
C12—C13—C14—C150.8 (5)C35—C36—C37—C321.0 (5)
C13—C14—C15—C161.0 (5)O41—S41—O41—S41'0 (47)
C14—C15—C16—C170.1 (5)C41—S41—O41—S41'43.9 (2)
C13—C12—C17—C161.3 (4)C42—S41—O41—S41'68.9 (4)
N3—C12—C17—C16176.6 (3)O41—S41'—O41—S410 (58)
C15—C16—C17—C121.0 (5)C42'—S41'—O41—S4168.3 (6)
N21—C21—C22—C23177.7 (3)C41—S41'—O41—S4144.7 (2)
C30—C21—C22—C236.7 (4)O41—S41'—C41—S4142.94 (17)
C21—C22—C23—C2446.8 (4)C42'—S41'—C41—S4175.5 (6)
C22—C23—C24—C2560.0 (4)O41—S41—C41—S41'42.81 (18)
C23—C24—C25—C26145.1 (3)C42—S41—C41—S41'71.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O410.882.082.945 (3)168
N23—H23N···O41i0.882.032.903 (3)173
Symmetry code: (i) x+1, y, z.
 

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