Crystal structure and DFT study of a zinc xanthate complex

Qadir, A.M.; Kansiz, S.; Dege, N.; Rosair, G.M.; Fritsky, I.O.

doi:10.1107/S2056989019013148

Crystal structure and DFT study of a zinc xanthate complex

A. M. Qadir, S. Kansiz, N. Dege, G. M. Rosair and I. O. Fritsky

In the title compound, the Zn^II ion is coordinated by two N atoms of the N,N,N′,N′-tetramethylethylenediamine ligand and two S atoms from two 2-methoxyethyl xanthate ligands. Two C—H

O and two C—H

S intramolecular interactions occur. In the crystal, molecules are linked by C—H

O and C—H

S hydrogen bonds, forming a three-dimensional supramolecular architecture.

Keywords: crystal structure; xanthate; zinc (II); DFT; molecular electrostatic potential.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019013148/lh5921sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019013148/lh5921Isup2.hkl Contains datablock I

CCDC reference: 1420207

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.040
wR factor = 0.105
Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
DENSD01_ALERT_1_B  The ratio of the submitted crystal density and that
            calculated from the formula is outside the range 0.95 <> 1.05
            Crystal density given    =      1.346
            Calculated crystal density =      1.426
PLAT043_ALERT_1_B Calculated and Reported Mol. Weight Differ by ..      29.02 Check
PLAT046_ALERT_1_B Reported Z, MW and D(calc) are Inconsistent ....      1.427 Check
PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of .        114 Ang   3

Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1       --C7       .        5.7 s.u.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5AA     ..S1       .       2.92 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A      ..O17      .       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9B      ..S2       .       2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18B     ..S2       .       3.02 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.089 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          5 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        103 Report
PLAT921_ALERT_1_C R1  in the CIF and FCF Differ by ...............    -0.0016 Check
PLAT922_ALERT_1_C wR2 in the CIF and FCF Differ by ...............    -0.0039 Check
PLAT923_ALERT_1_C S    Values in the CIF and FCF Differ by .......     -0.040 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C15.5 H33 N2 O4.5 S4 Zn1
            Atom count from the _atom_site data:  C14 H30 N2 O4 S4 Zn1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C15.5 H33 N2 O4.5 S4 Zn
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         62.00     56.00    6.00
           H        132.00    120.00   12.00
           N          8.00      8.00    0.00
           O         18.00     16.00    2.00
           S         16.00     16.00    0.00
           Zn         4.00      4.00    0.00
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         17 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         16 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        32% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         16 Note
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        244 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        122 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   4 ALERT level B = A potentially serious problem, consider carefully
  13 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  16 ALERT level G = General information/check it is not something unexpected

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
  10 ALERT type 4 Improvement, methodology, query or suggestion
   2 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: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis(2-methoxyethyl xanthato-κS)(N,N,N',N'-\ tetramethylethylenediamine-κ²N,N')zinc(II) acetone hemisolvate top

Crystal data top

[Zn(C₄H₇O₂S₂)₂(C₆H₁₆N₂)]·0.5C₃H₆O	F(000) = 1016
M_r = 513.05	D_x = 1.346 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.604 (3) Å	Cell parameters from 8223 reflections
b = 22.785 (6) Å	θ = 2.4–27.2°
c = 11.374 (3) Å	µ = 1.40 mm⁻¹
β = 106.304 (12)°	T = 100 K
V = 2389.0 (12) Å³	Plate, colourless
Z = 4	0.56 × 0.52 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	3870 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.054
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θ_max = 27.5°, θ_min = 2.6°
T_min = 0.594, T_max = 0.746	h = −12→12
35197 measured reflections	k = −29→29
5276 independent reflections	l = −13→14

Refinement top

Refinement on F²	244 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.057P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
5276 reflections	Δρ_max = 0.41 e Å⁻³
299 parameters	Δρ_min = −0.68 e Å⁻³

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	U_iso*/U_eq	Occ. (<1)
Zn1	0.94679 (3)	0.20615 (2)	0.25390 (3)	0.01743 (10)
S1	0.77332 (8)	0.16292 (3)	0.09443 (7)	0.02362 (17)
S2	0.81448 (9)	0.08333 (3)	−0.10110 (7)	0.02709 (19)
S3	1.11500 (8)	0.15676 (3)	0.40643 (6)	0.02205 (17)
S4	0.82433 (9)	0.13279 (3)	0.44905 (8)	0.0312 (2)
N1	1.0669 (9)	0.2630 (3)	0.1684 (7)	0.0187 (17)	0.538 (6)
N2	0.8649 (9)	0.2832 (2)	0.3157 (8)	0.0199 (19)	0.538 (6)
C1	1.0675 (9)	0.2455 (3)	0.0430 (7)	0.0234 (15)	0.538 (6)
H1A	0.9674	0.2412	−0.0084	0.035*	0.538 (6)
H1B	1.1167	0.2757	0.0081	0.035*	0.538 (6)
H1C	1.1187	0.2081	0.0465	0.035*	0.538 (6)
C2	1.2174 (11)	0.2697 (6)	0.2467 (12)	0.022 (2)	0.538 (6)
H2A	1.2162	0.2813	0.3294	0.034*	0.538 (6)
H2B	1.2689	0.2323	0.2505	0.034*	0.538 (6)
H2C	1.2669	0.3000	0.2121	0.034*	0.538 (6)
C3	0.9856 (7)	0.3192 (2)	0.1604 (6)	0.0229 (13)	0.538 (6)
H3A	0.8955	0.3170	0.0919	0.027*	0.538 (6)
H3B	1.0453	0.3517	0.1431	0.027*	0.538 (6)
C4	0.9477 (7)	0.3317 (2)	0.2780 (5)	0.0245 (13)	0.538 (6)
H4A	1.0384	0.3385	0.3442	0.029*	0.538 (6)
H4B	0.8894	0.3681	0.2679	0.029*	0.538 (6)
C5	0.7089 (10)	0.2896 (4)	0.2515 (12)	0.022 (2)	0.538 (6)
H5A	0.6950	0.2885	0.1628	0.033*	0.538 (6)
H5B	0.6548	0.2573	0.2750	0.033*	0.538 (6)
H5C	0.6736	0.3271	0.2740	0.033*	0.538 (6)
C6	0.883 (2)	0.2849 (6)	0.4502 (9)	0.029 (3)	0.538 (6)
H6A	0.9861	0.2808	0.4943	0.044*	0.538 (6)
H6B	0.8470	0.3225	0.4719	0.044*	0.538 (6)
H6C	0.8282	0.2527	0.4729	0.044*	0.538 (6)
N1A	1.0736 (10)	0.2669 (3)	0.1831 (8)	0.019 (2)	0.462 (6)
N2A	0.8391 (10)	0.2822 (3)	0.2930 (9)	0.020 (2)	0.462 (6)
C1A	1.0349 (10)	0.2672 (4)	0.0475 (7)	0.0209 (17)	0.462 (6)
H1AA	0.9303	0.2736	0.0142	0.031*	0.462 (6)
H1AB	1.0877	0.2988	0.0201	0.031*	0.462 (6)
H1AC	1.0611	0.2294	0.0184	0.031*	0.462 (6)
C2A	1.2323 (12)	0.2571 (7)	0.2278 (15)	0.026 (3)	0.462 (6)
H2AA	1.2624	0.2566	0.3175	0.039*	0.462 (6)
H2AB	1.2564	0.2194	0.1968	0.039*	0.462 (6)
H2AC	1.2830	0.2888	0.1985	0.039*	0.462 (6)
C3A	1.0409 (7)	0.3254 (3)	0.2283 (8)	0.0261 (15)	0.462 (6)
H3AA	1.0678	0.3568	0.1787	0.031*	0.462 (6)
H3AB	1.0991	0.3307	0.3145	0.031*	0.462 (6)
C4A	0.8818 (7)	0.3300 (3)	0.2199 (7)	0.0258 (15)	0.462 (6)
H4AA	0.8618	0.3687	0.2514	0.031*	0.462 (6)
H4AB	0.8237	0.3269	0.1332	0.031*	0.462 (6)
C5A	0.6793 (11)	0.2766 (5)	0.2581 (15)	0.022 (2)	0.462 (6)
H5AA	0.6435	0.2671	0.1708	0.033*	0.462 (6)
H5AB	0.6520	0.2452	0.3063	0.033*	0.462 (6)
H5AC	0.6365	0.3137	0.2741	0.033*	0.462 (6)
C6A	0.889 (2)	0.2966 (7)	0.4260 (10)	0.023 (3)	0.462 (6)
H6AA	0.9949	0.3006	0.4516	0.035*	0.462 (6)
H6AB	0.8448	0.3336	0.4409	0.035*	0.462 (6)
H6AC	0.8603	0.2651	0.4731	0.035*	0.462 (6)
C7	0.8778 (3)	0.11821 (10)	0.0299 (3)	0.0221 (6)
O8	1.0160 (2)	0.11540 (7)	0.09989 (17)	0.0220 (4)
C9	1.1153 (3)	0.07649 (11)	0.0618 (3)	0.0262 (7)
H9A	1.1345	0.0914	−0.0139	0.031*
H9B	1.0731	0.0367	0.0454	0.031*
C10	1.2527 (3)	0.07470 (11)	0.1641 (3)	0.0246 (6)
H10A	1.2301	0.0685	0.2429	0.030*
H10B	1.3139	0.0417	0.1514	0.030*
O11	1.3286 (2)	0.12830 (8)	0.1677 (2)	0.0318 (5)
C12	1.4621 (3)	0.12837 (14)	0.2611 (3)	0.0380 (8)
H12A	1.5113	0.1660	0.2607	0.057*
H12B	1.4437	0.1226	0.3408	0.057*
H12C	1.5237	0.0965	0.2463	0.057*
C13	1.0016 (3)	0.12252 (11)	0.4785 (3)	0.0208 (6)
O14	1.0774 (2)	0.08476 (8)	0.56361 (18)	0.0248 (4)
C15	1.0045 (4)	0.05469 (13)	0.6430 (3)	0.0303 (7)
H15A	0.9223	0.0311	0.5933	0.036*
H15B	0.9664	0.0836	0.6911	0.036*
C16	1.1136 (4)	0.01571 (12)	0.7265 (3)	0.0330 (8)
H16A	1.0658	−0.0086	0.7762	0.040*
H16B	1.1574	−0.0109	0.6779	0.040*
O17	1.2226 (2)	0.05108 (8)	0.80437 (19)	0.0278 (5)
C18	1.3393 (4)	0.01777 (13)	0.8787 (3)	0.0378 (8)
H18A	1.4112	0.0443	0.9305	0.057*
H18B	1.3026	−0.0089	0.9307	0.057*
H18C	1.3847	−0.0050	0.8264	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01874 (19)	0.01410 (15)	0.01842 (19)	0.00001 (12)	0.00353 (13)	−0.00176 (11)
S1	0.0204 (4)	0.0212 (3)	0.0258 (4)	0.0008 (3)	0.0008 (3)	−0.0072 (3)
S2	0.0331 (5)	0.0199 (3)	0.0239 (4)	−0.0004 (3)	0.0008 (3)	−0.0061 (3)
S3	0.0203 (4)	0.0247 (3)	0.0203 (4)	0.0006 (3)	0.0042 (3)	0.0036 (3)
S4	0.0221 (4)	0.0326 (4)	0.0391 (5)	−0.0011 (3)	0.0089 (4)	−0.0034 (3)
N1	0.019 (3)	0.014 (3)	0.024 (3)	0.004 (2)	0.006 (3)	0.002 (2)
N2	0.023 (3)	0.016 (2)	0.018 (4)	−0.002 (2)	0.002 (3)	−0.003 (2)
C1	0.029 (4)	0.022 (4)	0.023 (3)	0.001 (3)	0.012 (3)	−0.003 (3)
C2	0.023 (4)	0.022 (5)	0.024 (5)	0.001 (3)	0.009 (3)	0.001 (3)
C3	0.027 (3)	0.013 (2)	0.029 (3)	0.003 (2)	0.009 (2)	0.003 (2)
C4	0.028 (3)	0.016 (2)	0.030 (3)	−0.002 (2)	0.009 (3)	−0.005 (2)
C5	0.019 (4)	0.011 (4)	0.034 (4)	−0.006 (3)	0.006 (3)	−0.003 (3)
C6	0.045 (5)	0.028 (5)	0.014 (4)	0.002 (4)	0.008 (4)	−0.008 (4)
N1A	0.022 (3)	0.016 (3)	0.020 (3)	−0.001 (3)	0.004 (3)	−0.001 (3)
N2A	0.025 (4)	0.016 (3)	0.016 (4)	−0.002 (2)	0.002 (3)	−0.009 (2)
C1A	0.024 (4)	0.024 (4)	0.016 (3)	−0.001 (3)	0.008 (3)	−0.005 (3)
C2A	0.013 (4)	0.033 (7)	0.030 (6)	−0.004 (4)	0.001 (4)	0.002 (4)
C3A	0.034 (3)	0.015 (2)	0.031 (3)	−0.002 (2)	0.010 (3)	−0.005 (2)
C4A	0.033 (3)	0.017 (2)	0.025 (3)	0.005 (3)	0.004 (3)	−0.002 (2)
C5A	0.016 (5)	0.013 (5)	0.033 (5)	−0.004 (3)	0.000 (4)	−0.006 (3)
C6A	0.023 (4)	0.033 (6)	0.014 (5)	−0.001 (4)	0.003 (4)	−0.005 (4)
C7	0.0281 (17)	0.0105 (11)	0.0239 (16)	−0.0027 (11)	0.0008 (13)	0.0009 (10)
O8	0.0218 (11)	0.0173 (9)	0.0240 (11)	0.0031 (7)	0.0019 (9)	−0.0058 (7)
C9	0.0274 (17)	0.0213 (13)	0.0292 (17)	0.0043 (12)	0.0070 (13)	−0.0070 (11)
C10	0.0270 (17)	0.0133 (12)	0.0343 (18)	0.0000 (11)	0.0097 (13)	−0.0023 (11)
O11	0.0291 (13)	0.0238 (10)	0.0375 (13)	−0.0099 (9)	0.0012 (10)	0.0063 (9)
C12	0.0253 (19)	0.0333 (17)	0.049 (2)	−0.0047 (13)	−0.0001 (16)	−0.0026 (14)
C13	0.0247 (16)	0.0187 (12)	0.0174 (15)	−0.0010 (11)	0.0033 (12)	−0.0016 (10)
O14	0.0255 (12)	0.0254 (10)	0.0253 (12)	−0.0016 (8)	0.0100 (9)	0.0046 (8)
C15	0.037 (2)	0.0319 (15)	0.0236 (18)	−0.0143 (13)	0.0105 (14)	0.0024 (12)
C16	0.052 (2)	0.0203 (14)	0.0284 (18)	−0.0091 (14)	0.0133 (15)	0.0034 (12)
O17	0.0337 (13)	0.0198 (9)	0.0277 (12)	0.0002 (8)	0.0051 (10)	0.0041 (8)
C18	0.044 (2)	0.0318 (16)	0.037 (2)	0.0101 (14)	0.0098 (16)	0.0124 (14)

Geometric parameters (Å, º) top

Zn1—S1	2.3107 (9)	C1A—H1AB	0.9800
Zn1—S3	2.3050 (9)	C1A—H1AC	0.9800
Zn1—N1	2.141 (5)	C2A—H2AA	0.9800
Zn1—N2	2.123 (5)	C2A—H2AB	0.9800
Zn1—N1A	2.144 (6)	C2A—H2AC	0.9800
Zn1—N2A	2.128 (6)	C3A—H3AA	0.9900
S1—C7	1.731 (3)	C3A—H3AB	0.9900
S2—C7	1.647 (3)	C3A—C4A	1.508 (7)
S3—C13	1.723 (3)	C4A—H4AA	0.9900
S4—C13	1.657 (3)	C4A—H4AB	0.9900
N1—C1	1.482 (6)	C5A—H5AA	0.9800
N1—C2	1.477 (7)	C5A—H5AB	0.9800
N1—C3	1.489 (6)	C5A—H5AC	0.9800
N2—C4	1.492 (6)	C6A—H6AA	0.9800
N2—C5	1.478 (7)	C6A—H6AB	0.9800
N2—C6	1.491 (7)	C6A—H6AC	0.9800
C1—H1A	0.9800	C7—O8	1.344 (3)
C1—H1B	0.9800	O8—C9	1.454 (3)
C1—H1C	0.9800	C9—H9A	0.9900
C2—H2A	0.9800	C9—H9B	0.9900
C2—H2B	0.9800	C9—C10	1.495 (4)
C2—H2C	0.9800	C10—H10A	0.9900
C3—H3A	0.9900	C10—H10B	0.9900
C3—H3B	0.9900	C10—O11	1.417 (3)
C3—C4	1.509 (6)	O11—C12	1.417 (4)
C4—H4A	0.9900	C12—H12A	0.9800
C4—H4B	0.9900	C12—H12B	0.9800
C5—H5A	0.9800	C12—H12C	0.9800
C5—H5B	0.9800	C13—O14	1.346 (3)
C5—H5C	0.9800	O14—C15	1.459 (3)
C6—H6A	0.9800	C15—H15A	0.9900
C6—H6B	0.9800	C15—H15B	0.9900
C6—H6C	0.9800	C15—C16	1.494 (4)
N1A—C1A	1.482 (7)	C16—H16A	0.9900
N1A—C2A	1.482 (7)	C16—H16B	0.9900
N1A—C3A	1.494 (7)	C16—O17	1.418 (4)
N2A—C4A	1.496 (7)	O17—C18	1.420 (4)
N2A—C5A	1.479 (7)	C18—H18A	0.9800
N2A—C6A	1.490 (7)	C18—H18B	0.9800
C1A—H1AA	0.9800	C18—H18C	0.9800

S3—Zn1—S1	125.54 (3)	H1AB—C1A—H1AC	109.5
N1—Zn1—S1	105.2 (2)	N1A—C2A—H2AA	109.5
N1—Zn1—S3	106.5 (2)	N1A—C2A—H2AB	109.5
N2—Zn1—S1	111.1 (2)	N1A—C2A—H2AC	109.5
N2—Zn1—S3	113.7 (2)	H2AA—C2A—H2AB	109.5
N2—Zn1—N1	86.9 (2)	H2AA—C2A—H2AC	109.5
N1A—Zn1—S1	109.9 (3)	H2AB—C2A—H2AC	109.5
N1A—Zn1—S3	104.2 (3)	N1A—C3A—H3AA	109.6
N2A—Zn1—S1	103.0 (3)	N1A—C3A—H3AB	109.6
N2A—Zn1—S3	121.3 (3)	N1A—C3A—C4A	110.4 (6)
N2A—Zn1—N1A	85.1 (3)	H3AA—C3A—H3AB	108.1
C7—S1—Zn1	101.98 (10)	C4A—C3A—H3AA	109.6
C13—S3—Zn1	100.13 (10)	C4A—C3A—H3AB	109.6
C1—N1—Zn1	115.0 (5)	N2A—C4A—C3A	110.2 (6)
C1—N1—C3	108.4 (5)	N2A—C4A—H4AA	109.6
C2—N1—Zn1	110.4 (8)	N2A—C4A—H4AB	109.6
C2—N1—C1	109.9 (7)	C3A—C4A—H4AA	109.6
C2—N1—C3	110.8 (7)	C3A—C4A—H4AB	109.6
C3—N1—Zn1	102.0 (4)	H4AA—C4A—H4AB	108.1
C4—N2—Zn1	103.9 (4)	N2A—C5A—H5AA	109.5
C5—N2—Zn1	109.6 (7)	N2A—C5A—H5AB	109.5
C5—N2—C4	109.5 (6)	N2A—C5A—H5AC	109.5
C5—N2—C6	108.4 (9)	H5AA—C5A—H5AB	109.5
C6—N2—Zn1	114.5 (7)	H5AA—C5A—H5AC	109.5
C6—N2—C4	110.9 (7)	H5AB—C5A—H5AC	109.5
N1—C1—H1A	109.5	N2A—C6A—H6AA	109.5
N1—C1—H1B	109.5	N2A—C6A—H6AB	109.5
N1—C1—H1C	109.5	N2A—C6A—H6AC	109.5
H1A—C1—H1B	109.5	H6AA—C6A—H6AB	109.5
H1A—C1—H1C	109.5	H6AA—C6A—H6AC	109.5
H1B—C1—H1C	109.5	H6AB—C6A—H6AC	109.5
N1—C2—H2A	109.5	S2—C7—S1	123.82 (18)
N1—C2—H2B	109.5	O8—C7—S1	111.76 (19)
N1—C2—H2C	109.5	O8—C7—S2	124.4 (2)
H2A—C2—H2B	109.5	C7—O8—C9	118.3 (2)
H2A—C2—H2C	109.5	O8—C9—H9A	110.3
H2B—C2—H2C	109.5	O8—C9—H9B	110.3
N1—C3—H3A	109.4	O8—C9—C10	107.1 (2)
N1—C3—H3B	109.4	H9A—C9—H9B	108.5
N1—C3—C4	111.1 (5)	C10—C9—H9A	110.3
H3A—C3—H3B	108.0	C10—C9—H9B	110.3
C4—C3—H3A	109.4	C9—C10—H10A	109.8
C4—C3—H3B	109.4	C9—C10—H10B	109.8
N2—C4—C3	113.3 (5)	H10A—C10—H10B	108.2
N2—C4—H4A	108.9	O11—C10—C9	109.5 (2)
N2—C4—H4B	108.9	O11—C10—H10A	109.8
C3—C4—H4A	108.9	O11—C10—H10B	109.8
C3—C4—H4B	108.9	C12—O11—C10	111.9 (2)
H4A—C4—H4B	107.7	O11—C12—H12A	109.5
N2—C5—H5A	109.5	O11—C12—H12B	109.5
N2—C5—H5B	109.5	O11—C12—H12C	109.5
N2—C5—H5C	109.5	H12A—C12—H12B	109.5
H5A—C5—H5B	109.5	H12A—C12—H12C	109.5
H5A—C5—H5C	109.5	H12B—C12—H12C	109.5
H5B—C5—H5C	109.5	S4—C13—S3	126.24 (16)
N2—C6—H6A	109.5	O14—C13—S3	110.2 (2)
N2—C6—H6B	109.5	O14—C13—S4	123.6 (2)
N2—C6—H6C	109.5	C13—O14—C15	119.2 (2)
H6A—C6—H6B	109.5	O14—C15—H15A	110.2
H6A—C6—H6C	109.5	O14—C15—H15B	110.2
H6B—C6—H6C	109.5	O14—C15—C16	107.5 (3)
C1A—N1A—Zn1	113.0 (6)	H15A—C15—H15B	108.5
C1A—N1A—C3A	109.8 (6)	C16—C15—H15A	110.2
C2A—N1A—Zn1	114.3 (9)	C16—C15—H15B	110.2
C2A—N1A—C1A	106.9 (8)	C15—C16—H16A	109.9
C2A—N1A—C3A	108.2 (7)	C15—C16—H16B	109.9
C3A—N1A—Zn1	104.5 (4)	H16A—C16—H16B	108.3
C4A—N2A—Zn1	104.6 (4)	O17—C16—C15	108.8 (2)
C5A—N2A—Zn1	113.7 (7)	O17—C16—H16A	109.9
C5A—N2A—C4A	109.8 (7)	O17—C16—H16B	109.9
C5A—N2A—C6A	107.8 (9)	C16—O17—C18	112.9 (2)
C6A—N2A—Zn1	110.8 (9)	O17—C18—H18A	109.5
C6A—N2A—C4A	110.1 (8)	O17—C18—H18B	109.5
N1A—C1A—H1AA	109.5	O17—C18—H18C	109.5
N1A—C1A—H1AB	109.5	H18A—C18—H18B	109.5
N1A—C1A—H1AC	109.5	H18A—C18—H18C	109.5
H1AA—C1A—H1AB	109.5	H18B—C18—H18C	109.5
H1AA—C1A—H1AC	109.5

Zn1—S1—C7—S2	−170.71 (15)	C2—N1—C3—C4	−73.8 (9)
Zn1—S1—C7—O8	9.49 (19)	C5—N2—C4—C3	−84.1 (8)
Zn1—S3—C13—S4	−6.90 (19)	C6—N2—C4—C3	156.4 (9)
Zn1—S3—C13—O14	172.51 (16)	N1A—C3A—C4A—N2A	58.4 (9)
Zn1—N1—C3—C4	43.8 (6)	C1A—N1A—C3A—C4A	81.0 (8)
Zn1—N2—C4—C3	32.9 (7)	C2A—N1A—C3A—C4A	−162.6 (10)
Zn1—N1A—C3A—C4A	−40.5 (8)	C5A—N2A—C4A—C3A	−164.5 (9)
Zn1—N2A—C4A—C3A	−42.1 (8)	C6A—N2A—C4A—C3A	77.0 (10)
S1—C7—O8—C9	176.11 (18)	C7—O8—C9—C10	−171.4 (2)
S2—C7—O8—C9	−3.7 (3)	O8—C9—C10—O11	−73.4 (3)
S3—C13—O14—C15	174.79 (18)	C9—C10—O11—C12	−178.4 (2)
S4—C13—O14—C15	−5.8 (3)	C13—O14—C15—C16	179.5 (2)
N1—C3—C4—N2	−55.6 (8)	O14—C15—C16—O17	65.4 (3)
C1—N1—C3—C4	165.5 (6)	C15—C16—O17—C18	−173.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···O8	0.98	2.48	3.103 (7)	121
C2A—H2AB···O11	0.98	2.24	3.207 (13)	168
C5A—H5AA···S1	0.98	2.92	3.454 (16)	115
C6—H6C···S4	0.98	2.74	3.512 (13)	136
C6—H6B···O11ⁱ	0.98	2.54	3.321 (13)	136
C3A—H3AB···S2ⁱⁱ	0.99	2.81	3.483 (7)	125
C6A—H6AA···S1ⁱⁱ	0.98	2.84	3.764 (16)	158
C4A—H4AA···O17ⁱⁱⁱ	0.99	2.44	3.380 (6)	159
C4A—H4AB···S3ⁱⁱⁱ	0.99	2.81	3.774 (8)	164
C9—H9A···O17^iv	0.99	2.61	3.415 (4)	138
C9—H9B···S2^v	0.99	2.94	3.708 (3)	135
C18—H18B···S2^vi	0.98	3.02	3.998 (3)	176

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) x, y, z−1; (v) −x+2, −y, −z; (vi) −x+2, −y, −z+1.

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