Bis(4-meth­oxy­chalcone 4-ethyl­thio­semi­carbazon­ato-κ2N1,S)zinc(II): crystal structure and Hirshfeld surface analysis

Tan, M.Y.; Crouse, K.A.; Ravoof, T.B.S.A.; Jotani, M.M.; Tiekink, E.R.T.

doi:10.1107/S2056989018000282

Bis(4-methoxychalcone 4-ethylthiosemicarbazonato-κ²N¹,S)zinc(II): crystal structure and Hirshfeld surface analysis

M. Y. Tan, K. A. Crouse, T. B. S. A. Ravoof, M. M. Jotani and E. R. T. Tiekink

The title thiosemicarbazone compound features tetrahedrally coordinated Zn^II atoms within N₂S₂ donor sets because of the presence of chelating thiosemicarbazone anions. Supramolecular chains are found in the crystal owing to the formation of thioamide-N—H

S(thione) hydrogen bonds and eight-membered thioamide {

HNCS}₂ synthons.

Keywords: crystal structure; zinc; hydrogen bonding; thiosemicarbazone; Hirshfeld surface analysis.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018000282/hb7725sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989018000282/hb7725Isup2.hkl Contains datablock I

CCDC reference: 1814817

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.007 Å
R factor = 0.065
wR factor = 0.171
Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.3 Ratio
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00662 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          9 Note
PLAT973_ALERT_2_C Check Calcd Positive Resid. Density on        Zn       1.35 eA-3

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.005 Degree
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis[(N-ethyl-N'-{(Z)-[(2E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-ylidene]amino}carbamimidoyl)sulfanido]zinc(II) top

Crystal data top

[Zn(C₁₉H₂₀N₃OS)₂]	Z = 2
M_r = 742.25	F(000) = 776
Triclinic, P1	D_x = 1.338 Mg m⁻³
a = 10.5013 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.2836 (8) Å	Cell parameters from 4004 reflections
c = 14.8282 (9) Å	θ = 2.8–27.5°
α = 107.173 (5)°	µ = 0.82 mm⁻¹
β = 108.152 (5)°	T = 100 K
γ = 106.259 (5)°	Prism, yellow
V = 1842.0 (2) Å³	0.25 × 0.15 × 0.05 mm

Data collection top

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	8464 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5619 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.071
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ω scan	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −18→18
T_min = 0.887, T_max = 1.000	l = −19→19
19299 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.065	w = 1/[σ²(F_o²) + (0.066P)² + 1.1328P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.171	(Δ/σ)_max = 0.001
S = 1.01	Δρ_max = 1.10 e Å⁻³
8464 reflections	Δρ_min = −0.59 e Å⁻³
452 parameters

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.

Refinement. The maximum and minimum residual electron density peaks of 1.10 and 0.59 eÅ^-3, respectively, were located 1.04 Å and 0.71 Å from the Zn atom.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn	0.61283 (5)	0.39864 (3)	0.26017 (3)	0.01731 (14)
S1	0.53424 (11)	0.44366 (8)	0.12335 (8)	0.0199 (2)
S2	0.63421 (11)	0.47815 (8)	0.42482 (7)	0.0209 (2)
O1	1.0784 (3)	0.3417 (2)	0.8198 (2)	0.0285 (7)
O2	0.2660 (4)	0.0652 (2)	−0.4057 (2)	0.0383 (8)
N1	0.6593 (4)	0.4265 (3)	−0.0084 (2)	0.0211 (8)
H1N	0.615 (5)	0.463 (3)	−0.029 (3)	0.025*
N2	0.7664 (4)	0.3874 (2)	0.1248 (2)	0.0192 (7)
N3	0.7733 (3)	0.3790 (2)	0.2167 (2)	0.0162 (7)
N4	0.5490 (4)	0.3597 (3)	0.5203 (2)	0.0221 (8)
H4N	0.556 (5)	0.420 (3)	0.556 (3)	0.027*
N5	0.4901 (4)	0.2575 (3)	0.3512 (2)	0.0201 (7)
N6	0.4944 (4)	0.2545 (2)	0.2579 (2)	0.0186 (7)
C1	0.6656 (4)	0.4179 (3)	0.0811 (3)	0.0163 (8)
C2	0.7722 (5)	0.4190 (4)	−0.0435 (3)	0.0346 (11)
H2A	0.7767	0.3485	−0.0534	0.042*
H2B	0.8689	0.4758	0.0106	0.042*
C3	0.7415 (7)	0.4310 (5)	−0.1443 (4)	0.0499 (14)
H3A	0.6472	0.3735	−0.1986	0.075*
H3B	0.8198	0.4266	−0.1657	0.075*
H3C	0.7373	0.5008	−0.1347	0.075*
C4	0.8760 (4)	0.3507 (3)	0.2610 (3)	0.0160 (8)
C5	0.8940 (4)	0.3512 (3)	0.3620 (3)	0.0188 (8)
H5	0.8345	0.3757	0.3913	0.023*
C6	0.9879 (4)	0.3199 (3)	0.4181 (3)	0.0183 (8)
H6	1.0445	0.2925	0.3877	0.022*
C7	1.0097 (4)	0.3247 (3)	0.5222 (3)	0.0203 (9)
C8	1.1094 (5)	0.2881 (3)	0.5709 (3)	0.0246 (9)
H8	1.1610	0.2602	0.5355	0.030*
C9	1.1352 (4)	0.2915 (3)	0.6701 (3)	0.0241 (9)
H9	1.2025	0.2653	0.7015	0.029*
C10	1.0617 (5)	0.3334 (3)	0.7223 (3)	0.0233 (9)
C11	0.9624 (5)	0.3715 (3)	0.6745 (3)	0.0238 (9)
H11	0.9126	0.4012	0.7105	0.029*
C12	0.9368 (4)	0.3663 (3)	0.5766 (3)	0.0223 (9)
H12	0.8681	0.3915	0.5450	0.027*
C13	1.1781 (5)	0.3025 (3)	0.8702 (3)	0.0309 (11)
H13A	1.1450	0.2258	0.8276	0.046*
H13B	1.1807	0.3128	0.9392	0.046*
H13C	1.2766	0.3420	0.8782	0.046*
C14	0.9722 (4)	0.3227 (3)	0.2124 (3)	0.0186 (8)
C15	0.9112 (5)	0.2427 (3)	0.1112 (3)	0.0228 (9)
H15	0.8075	0.2064	0.0726	0.027*
C16	1.0016 (5)	0.2162 (3)	0.0672 (3)	0.0266 (10)
H16	0.9595	0.1606	−0.0011	0.032*
C17	1.1524 (5)	0.2698 (3)	0.1217 (3)	0.0275 (10)
H17	1.2137	0.2525	0.0902	0.033*
C18	1.2141 (5)	0.3488 (3)	0.2223 (3)	0.0280 (10)
H18	1.3179	0.3849	0.2603	0.034*
C19	1.1250 (4)	0.3755 (3)	0.2677 (3)	0.0224 (9)
H19	1.1679	0.4299	0.3368	0.027*
C20	0.5495 (4)	0.3535 (3)	0.4270 (3)	0.0184 (8)
C21	0.4684 (5)	0.2645 (3)	0.5309 (3)	0.0299 (10)
H21A	0.3728	0.2218	0.4686	0.036*
H21B	0.4480	0.2881	0.5928	0.036*
C22	0.5510 (6)	0.1933 (4)	0.5426 (4)	0.0411 (12)
H22A	0.5634	0.1641	0.4788	0.062*
H22B	0.4950	0.1342	0.5543	0.062*
H22C	0.6477	0.2359	0.6023	0.062*
C23	0.4179 (4)	0.1593 (3)	0.1782 (3)	0.0200 (9)
C24	0.4155 (4)	0.1516 (3)	0.0785 (3)	0.0216 (9)
H24	0.4833	0.2114	0.0780	0.026*
C25	0.3253 (5)	0.0669 (3)	−0.0139 (3)	0.0248 (9)
H25	0.2647	0.0039	−0.0132	0.030*
C26	0.3140 (5)	0.0651 (3)	−0.1153 (3)	0.0249 (10)
C27	0.2184 (5)	−0.0286 (3)	−0.2070 (3)	0.0295 (10)
H27	0.1651	−0.0911	−0.2018	0.035*
C28	0.1998 (5)	−0.0322 (3)	−0.3052 (3)	0.0318 (11)
H28	0.1346	−0.0966	−0.3661	0.038*
C29	0.2763 (5)	0.0582 (3)	−0.3139 (3)	0.0299 (10)
C30	0.3721 (5)	0.1522 (3)	−0.2241 (3)	0.0282 (10)
H30	0.4247	0.2148	−0.2295	0.034*
C31	0.3900 (5)	0.1540 (3)	−0.1278 (3)	0.0259 (10)
H31	0.4567	0.2184	−0.0673	0.031*
C32	0.1792 (7)	−0.0321 (4)	−0.5000 (3)	0.0525 (16)
H32A	0.2138	−0.0877	−0.4931	0.079*
H32B	0.1885	−0.0185	−0.5591	0.079*
H32C	0.0759	−0.0563	−0.5120	0.079*
C33	0.3334 (5)	0.0649 (3)	0.1917 (3)	0.0218 (9)
C34	0.3828 (5)	−0.0154 (3)	0.1916 (4)	0.0319 (11)
H34	0.4668	−0.0129	0.1790	0.038*
C35	0.3087 (5)	−0.0999 (4)	0.2103 (4)	0.0385 (12)
H35	0.3436	−0.1544	0.2112	0.046*
C36	0.1864 (5)	−0.1056 (3)	0.2271 (3)	0.0327 (11)
H36	0.1371	−0.1633	0.2401	0.039*
C37	0.1351 (5)	−0.0266 (3)	0.2251 (3)	0.0317 (11)
H37	0.0494	−0.0306	0.2357	0.038*
C38	0.2088 (5)	0.0584 (3)	0.2076 (3)	0.0274 (10)
H38	0.1733	0.1125	0.2065	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.0161 (2)	0.0230 (2)	0.0138 (2)	0.00749 (18)	0.00647 (18)	0.00934 (18)
S1	0.0182 (5)	0.0282 (5)	0.0191 (5)	0.0120 (4)	0.0084 (4)	0.0146 (4)
S2	0.0217 (5)	0.0230 (5)	0.0160 (5)	0.0072 (4)	0.0089 (4)	0.0068 (4)
O1	0.0313 (17)	0.0351 (16)	0.0156 (14)	0.0077 (13)	0.0071 (13)	0.0147 (13)
O2	0.050 (2)	0.0385 (17)	0.0188 (16)	0.0078 (16)	0.0142 (15)	0.0127 (14)
N1	0.0229 (19)	0.0325 (19)	0.0167 (17)	0.0154 (15)	0.0089 (14)	0.0173 (15)
N2	0.0205 (18)	0.0293 (17)	0.0120 (16)	0.0113 (14)	0.0083 (13)	0.0117 (14)
N3	0.0156 (16)	0.0206 (16)	0.0112 (15)	0.0069 (13)	0.0046 (13)	0.0068 (13)
N4	0.0245 (19)	0.0297 (18)	0.0118 (16)	0.0102 (16)	0.0098 (14)	0.0070 (14)
N5	0.0214 (18)	0.0260 (17)	0.0140 (16)	0.0093 (14)	0.0083 (14)	0.0095 (14)
N6	0.0195 (17)	0.0263 (17)	0.0159 (16)	0.0117 (14)	0.0096 (13)	0.0121 (14)
C1	0.018 (2)	0.0170 (18)	0.0117 (18)	0.0046 (15)	0.0047 (15)	0.0066 (15)
C2	0.039 (3)	0.054 (3)	0.024 (2)	0.027 (2)	0.018 (2)	0.024 (2)
C3	0.055 (4)	0.076 (4)	0.040 (3)	0.032 (3)	0.032 (3)	0.035 (3)
C4	0.0141 (19)	0.0165 (17)	0.0130 (18)	0.0033 (15)	0.0031 (15)	0.0064 (15)
C5	0.017 (2)	0.027 (2)	0.0177 (19)	0.0095 (16)	0.0106 (16)	0.0125 (16)
C6	0.020 (2)	0.0224 (19)	0.0132 (18)	0.0077 (16)	0.0076 (15)	0.0081 (16)
C7	0.021 (2)	0.0204 (19)	0.0145 (19)	0.0067 (16)	0.0039 (16)	0.0062 (16)
C8	0.026 (2)	0.032 (2)	0.019 (2)	0.0132 (18)	0.0099 (17)	0.0130 (18)
C9	0.021 (2)	0.033 (2)	0.020 (2)	0.0128 (18)	0.0040 (17)	0.0171 (18)
C10	0.025 (2)	0.023 (2)	0.0137 (19)	0.0021 (17)	0.0042 (17)	0.0087 (16)
C11	0.026 (2)	0.027 (2)	0.018 (2)	0.0089 (18)	0.0097 (17)	0.0090 (17)
C12	0.023 (2)	0.025 (2)	0.016 (2)	0.0109 (17)	0.0050 (16)	0.0077 (16)
C13	0.034 (3)	0.037 (2)	0.017 (2)	0.009 (2)	0.0023 (18)	0.0198 (19)
C14	0.020 (2)	0.0241 (19)	0.0157 (19)	0.0098 (16)	0.0079 (16)	0.0120 (16)
C15	0.029 (2)	0.026 (2)	0.0137 (19)	0.0125 (18)	0.0060 (17)	0.0097 (16)
C16	0.036 (3)	0.032 (2)	0.017 (2)	0.023 (2)	0.0105 (18)	0.0102 (18)
C17	0.036 (3)	0.042 (2)	0.022 (2)	0.026 (2)	0.0203 (19)	0.0186 (19)
C18	0.021 (2)	0.039 (2)	0.025 (2)	0.0130 (19)	0.0080 (18)	0.018 (2)
C19	0.024 (2)	0.028 (2)	0.0142 (19)	0.0108 (17)	0.0063 (16)	0.0094 (17)
C20	0.0149 (19)	0.027 (2)	0.0157 (19)	0.0104 (16)	0.0064 (15)	0.0104 (16)
C21	0.026 (2)	0.042 (3)	0.022 (2)	0.008 (2)	0.0134 (18)	0.016 (2)
C22	0.036 (3)	0.047 (3)	0.046 (3)	0.013 (2)	0.019 (2)	0.030 (2)
C23	0.021 (2)	0.025 (2)	0.0168 (19)	0.0100 (17)	0.0095 (16)	0.0090 (16)
C24	0.025 (2)	0.0185 (18)	0.022 (2)	0.0072 (16)	0.0106 (17)	0.0106 (16)
C25	0.032 (2)	0.021 (2)	0.019 (2)	0.0095 (18)	0.0115 (18)	0.0070 (17)
C26	0.028 (2)	0.022 (2)	0.016 (2)	0.0072 (18)	0.0065 (17)	0.0037 (17)
C27	0.032 (3)	0.029 (2)	0.020 (2)	0.0041 (19)	0.0109 (19)	0.0103 (18)
C28	0.042 (3)	0.027 (2)	0.014 (2)	0.006 (2)	0.0066 (19)	0.0063 (17)
C29	0.037 (3)	0.036 (2)	0.019 (2)	0.015 (2)	0.0140 (19)	0.0139 (19)
C30	0.036 (3)	0.026 (2)	0.023 (2)	0.0109 (19)	0.0135 (19)	0.0120 (18)
C31	0.032 (2)	0.025 (2)	0.018 (2)	0.0076 (18)	0.0114 (18)	0.0096 (17)
C32	0.073 (4)	0.047 (3)	0.015 (2)	0.004 (3)	0.014 (2)	0.008 (2)
C33	0.025 (2)	0.024 (2)	0.0129 (19)	0.0068 (17)	0.0072 (16)	0.0075 (16)
C34	0.030 (3)	0.032 (2)	0.037 (3)	0.012 (2)	0.016 (2)	0.017 (2)
C35	0.037 (3)	0.033 (2)	0.046 (3)	0.014 (2)	0.010 (2)	0.025 (2)
C36	0.036 (3)	0.027 (2)	0.027 (2)	0.0022 (19)	0.009 (2)	0.0163 (19)
C37	0.030 (3)	0.034 (2)	0.026 (2)	0.005 (2)	0.012 (2)	0.013 (2)
C38	0.031 (3)	0.026 (2)	0.028 (2)	0.0095 (18)	0.0146 (19)	0.0142 (18)

Geometric parameters (Å, º) top

Zn—N3	2.041 (3)	C14—C15	1.395 (5)
Zn—N6	2.071 (3)	C14—C19	1.397 (5)
Zn—S1	2.2879 (11)	C15—C16	1.382 (6)
Zn—S2	2.2757 (11)	C15—H15	0.9500
C1—N2	1.314 (5)	C16—C17	1.381 (6)
C4—N3	1.310 (5)	C16—H16	0.9500
C5—C6	1.349 (5)	C17—C18	1.383 (6)
C20—N5	1.307 (5)	C17—H17	0.9500
C23—N6	1.319 (5)	C18—C19	1.384 (6)
C24—C25	1.344 (5)	C18—H18	0.9500
S2—C20	1.768 (4)	C19—H19	0.9500
O1—C10	1.365 (5)	C21—C22	1.524 (6)
O1—C13	1.433 (5)	C21—H21A	0.9900
O2—C29	1.366 (5)	C21—H21B	0.9900
O2—C32	1.438 (5)	C22—H22A	0.9800
N1—C1	1.352 (5)	C22—H22B	0.9800
N1—C2	1.453 (6)	C22—H22C	0.9800
N1—H1N	0.85 (4)	C23—C24	1.441 (6)
N2—N3	1.385 (4)	C23—C33	1.499 (6)
N4—C20	1.361 (5)	C24—H24	0.9500
N4—C21	1.467 (6)	C25—C26	1.463 (6)
N4—H4N	0.83 (4)	C25—H25	0.9500
N5—N6	1.386 (5)	C26—C31	1.396 (6)
C2—C3	1.500 (7)	C26—C27	1.403 (5)
C2—H2A	0.9900	C27—C28	1.391 (6)
C2—H2B	0.9900	C27—H27	0.9500
C3—H3A	0.9800	C28—C29	1.382 (6)
C3—H3B	0.9800	C28—H28	0.9500
C3—H3C	0.9800	C29—C30	1.394 (6)
C4—C5	1.449 (5)	C30—C31	1.373 (6)
C4—C14	1.486 (5)	C30—H30	0.9500
C5—H5	0.9500	C31—H31	0.9500
C6—C7	1.465 (5)	C32—H32A	0.9800
C6—H6	0.9500	C32—H32B	0.9800
C7—C8	1.396 (6)	C32—H32C	0.9800
C7—C12	1.396 (6)	C33—C38	1.383 (6)
C8—C9	1.394 (6)	C33—C34	1.385 (6)
C8—H8	0.9500	C34—C35	1.394 (7)
C9—C10	1.382 (6)	C34—H34	0.9500
C9—H9	0.9500	C35—C36	1.368 (7)
C10—C11	1.404 (6)	C35—H35	0.9500
C11—C12	1.367 (6)	C36—C37	1.382 (6)
C11—H11	0.9500	C36—H36	0.9500
C12—H12	0.9500	C37—C38	1.388 (6)
C13—H13A	0.9800	C37—H37	0.9500
C13—H13B	0.9800	C38—H38	0.9500
C13—H13C	0.9800

N3—Zn—N6	107.16 (12)	C15—C16—C17	120.6 (4)
N3—Zn—S2	127.83 (9)	C15—C16—H16	119.7
N6—Zn—S2	86.73 (9)	C17—C16—H16	119.7
N3—Zn—S1	87.29 (9)	C16—C17—C18	119.8 (4)
N6—Zn—S1	121.90 (9)	C16—C17—H17	120.1
S2—Zn—S1	127.92 (4)	C18—C17—H17	120.1
C1—S1—Zn	92.45 (13)	C17—C18—C19	120.2 (4)
C20—S2—Zn	92.86 (13)	C17—C18—H18	119.9
C10—O1—C13	117.1 (3)	C19—C18—H18	119.9
C29—O2—C32	117.1 (4)	C18—C19—C14	120.3 (4)
C1—N1—C2	121.0 (3)	C18—C19—H19	119.9
C1—N1—H1N	118 (3)	C14—C19—H19	119.9
C2—N1—H1N	115 (3)	N5—C20—N4	116.9 (4)
C1—N2—N3	115.8 (3)	N5—C20—S2	128.0 (3)
C4—N3—N2	115.4 (3)	N4—C20—S2	115.1 (3)
C4—N3—Zn	127.7 (3)	N4—C21—C22	113.3 (4)
N2—N3—Zn	116.7 (2)	N4—C21—H21A	108.9
C20—N4—C21	121.3 (3)	C22—C21—H21A	108.9
C20—N4—H4N	111 (3)	N4—C21—H21B	108.9
C21—N4—H4N	120 (3)	C22—C21—H21B	108.9
C20—N5—N6	115.2 (3)	H21A—C21—H21B	107.7
C23—N6—N5	114.8 (3)	C21—C22—H22A	109.5
C23—N6—Zn	128.6 (3)	C21—C22—H22B	109.5
N5—N6—Zn	116.6 (2)	H22A—C22—H22B	109.5
N2—C1—N1	115.8 (4)	C21—C22—H22C	109.5
N2—C1—S1	127.4 (3)	H22A—C22—H22C	109.5
N1—C1—S1	116.8 (3)	H22B—C22—H22C	109.5
N1—C2—C3	111.2 (4)	N6—C23—C24	117.3 (4)
N1—C2—H2A	109.4	N6—C23—C33	120.4 (3)
C3—C2—H2A	109.4	C24—C23—C33	122.3 (3)
N1—C2—H2B	109.4	C25—C24—C23	125.5 (4)
C3—C2—H2B	109.4	C25—C24—H24	117.3
H2A—C2—H2B	108.0	C23—C24—H24	117.3
C2—C3—H3A	109.5	C24—C25—C26	124.5 (4)
C2—C3—H3B	109.5	C24—C25—H25	117.7
H3A—C3—H3B	109.5	C26—C25—H25	117.7
C2—C3—H3C	109.5	C31—C26—C27	116.6 (4)
H3A—C3—H3C	109.5	C31—C26—C25	123.6 (3)
H3B—C3—H3C	109.5	C27—C26—C25	119.8 (4)
N3—C4—C5	116.2 (3)	C28—C27—C26	121.6 (4)
N3—C4—C14	122.3 (3)	C28—C27—H27	119.2
C5—C4—C14	121.4 (3)	C26—C27—H27	119.2
C6—C5—C4	125.7 (4)	C29—C28—C27	119.9 (4)
C6—C5—H5	117.2	C29—C28—H28	120.1
C4—C5—H5	117.2	C27—C28—H28	120.1
C5—C6—C7	125.3 (4)	O2—C29—C28	125.4 (4)
C5—C6—H6	117.4	O2—C29—C30	114.9 (4)
C7—C6—H6	117.4	C28—C29—C30	119.7 (4)
C8—C7—C12	117.8 (4)	C31—C30—C29	119.6 (4)
C8—C7—C6	119.3 (4)	C31—C30—H30	120.2
C12—C7—C6	122.9 (4)	C29—C30—H30	120.2
C7—C8—C9	121.7 (4)	C30—C31—C26	122.7 (4)
C7—C8—H8	119.1	C30—C31—H31	118.7
C9—C8—H8	119.1	C26—C31—H31	118.7
C10—C9—C8	119.2 (4)	O2—C32—H32A	109.5
C10—C9—H9	120.4	O2—C32—H32B	109.5
C8—C9—H9	120.4	H32A—C32—H32B	109.5
O1—C10—C9	124.7 (4)	O2—C32—H32C	109.5
O1—C10—C11	115.8 (4)	H32A—C32—H32C	109.5
C9—C10—C11	119.5 (4)	H32B—C32—H32C	109.5
C12—C11—C10	120.6 (4)	C38—C33—C34	119.4 (4)
C12—C11—H11	119.7	C38—C33—C23	120.9 (4)
C10—C11—H11	119.7	C34—C33—C23	119.7 (4)
C11—C12—C7	121.1 (4)	C33—C34—C35	119.6 (5)
C11—C12—H12	119.4	C33—C34—H34	120.2
C7—C12—H12	119.4	C35—C34—H34	120.2
O1—C13—H13A	109.5	C36—C35—C34	121.0 (4)
O1—C13—H13B	109.5	C36—C35—H35	119.5
H13A—C13—H13B	109.5	C34—C35—H35	119.5
O1—C13—H13C	109.5	C35—C36—C37	119.5 (4)
H13A—C13—H13C	109.5	C35—C36—H36	120.2
H13B—C13—H13C	109.5	C37—C36—H36	120.2
C15—C14—C19	119.1 (4)	C38—C37—C36	120.0 (4)
C15—C14—C4	120.4 (3)	C38—C37—H37	120.0
C19—C14—C4	120.5 (3)	C36—C37—H37	120.0
C16—C15—C14	120.0 (4)	C33—C38—C37	120.5 (4)
C16—C15—H15	120.0	C33—C38—H38	119.7
C14—C15—H15	120.0	C37—C38—H38	119.7

C1—N2—N3—C4	−178.6 (3)	C15—C14—C19—C18	0.3 (6)
C1—N2—N3—Zn	6.6 (4)	C4—C14—C19—C18	179.8 (4)
C20—N5—N6—C23	−171.6 (3)	N6—N5—C20—N4	−179.2 (3)
C20—N5—N6—Zn	6.6 (4)	N6—N5—C20—S2	−0.3 (5)
N3—N2—C1—N1	179.8 (3)	C21—N4—C20—N5	−7.9 (5)
N3—N2—C1—S1	−2.8 (5)	C21—N4—C20—S2	173.0 (3)
C2—N1—C1—N2	−9.3 (5)	Zn—S2—C20—N5	−4.9 (4)
C2—N1—C1—S1	173.0 (3)	Zn—S2—C20—N4	174.0 (3)
Zn—S1—C1—N2	−1.7 (3)	C20—N4—C21—C22	80.6 (5)
Zn—S1—C1—N1	175.7 (3)	N5—N6—C23—C24	178.6 (3)
C1—N1—C2—C3	−180.0 (4)	Zn—N6—C23—C24	0.7 (5)
N2—N3—C4—C5	174.4 (3)	N5—N6—C23—C33	0.8 (5)
Zn—N3—C4—C5	−11.5 (5)	Zn—N6—C23—C33	−177.1 (3)
N2—N3—C4—C14	−3.8 (5)	N6—C23—C24—C25	−168.2 (4)
Zn—N3—C4—C14	170.3 (2)	C33—C23—C24—C25	9.6 (6)
N3—C4—C5—C6	176.5 (4)	C23—C24—C25—C26	173.3 (4)
C14—C4—C5—C6	−5.2 (6)	C24—C25—C26—C31	−4.0 (7)
C4—C5—C6—C7	177.4 (4)	C24—C25—C26—C27	178.6 (4)
C5—C6—C7—C8	179.1 (4)	C31—C26—C27—C28	−0.4 (7)
C5—C6—C7—C12	−2.0 (6)	C25—C26—C27—C28	177.2 (4)
C12—C7—C8—C9	0.7 (6)	C26—C27—C28—C29	−0.2 (7)
C6—C7—C8—C9	179.6 (4)	C32—O2—C29—C28	−6.2 (7)
C7—C8—C9—C10	−0.9 (6)	C32—O2—C29—C30	174.5 (4)
C13—O1—C10—C9	−0.9 (6)	C27—C28—C29—O2	−179.1 (4)
C13—O1—C10—C11	179.5 (3)	C27—C28—C29—C30	0.2 (7)
C8—C9—C10—O1	−179.5 (4)	O2—C29—C30—C31	179.7 (4)
C8—C9—C10—C11	0.1 (6)	C28—C29—C30—C31	0.3 (7)
O1—C10—C11—C12	−179.6 (4)	C29—C30—C31—C26	−0.9 (7)
C9—C10—C11—C12	0.8 (6)	C27—C26—C31—C30	1.0 (7)
C10—C11—C12—C7	−1.0 (6)	C25—C26—C31—C30	−176.5 (4)
C8—C7—C12—C11	0.3 (6)	N6—C23—C33—C38	70.3 (5)
C6—C7—C12—C11	−178.6 (4)	C24—C23—C33—C38	−107.4 (5)
N3—C4—C14—C15	−55.3 (5)	N6—C23—C33—C34	−107.7 (4)
C5—C4—C14—C15	126.6 (4)	C24—C23—C33—C34	74.6 (5)
N3—C4—C14—C19	125.3 (4)	C38—C33—C34—C35	−1.7 (6)
C5—C4—C14—C19	−52.9 (5)	C23—C33—C34—C35	176.4 (4)
C19—C14—C15—C16	0.3 (6)	C33—C34—C35—C36	1.0 (7)
C4—C14—C15—C16	−179.1 (4)	C34—C35—C36—C37	0.4 (7)
C14—C15—C16—C17	−1.3 (6)	C35—C36—C37—C38	−1.0 (7)
C15—C16—C17—C18	1.7 (7)	C34—C33—C38—C37	1.1 (6)
C16—C17—C18—C19	−1.1 (7)	C23—C33—C38—C37	−176.9 (4)
C17—C18—C19—C14	0.1 (6)	C36—C37—C38—C33	0.2 (6)

Hydrogen-bond geometry (Å, º) top

Cg1—Cg4 are the centroids of the (C33–C38), (Zn,S2,C20,N5,N6), (C26—C31) and (Zn,S1,C1,N2,N3) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1ⁱ	0.85 (5)	2.66 (5)	3.506 (4)	171 (3)
N4—H4N···S2ⁱⁱ	0.84 (5)	2.82 (5)	3.477 (5)	137 (4)
C36—H36···O1ⁱⁱⁱ	0.95	2.57	3.428 (6)	151
C16—H16···Cg1^iv	0.95	2.85	3.747 (4)	157
C18—H18···Cg2^v	0.95	2.69	3.485 (5)	141
C34—H34···Cg3^iv	0.95	2.72	3.555 (6)	148
C5—H5···Cg2	0.95	2.67	3.462 (5)	142
C24—H24···Cg4	0.95	2.55	3.421 (5)	153

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

Summary of short inter-atomic contacts (Å) in (I) top

Contact	Distance	Symmetry operation
H3B···H11	2.11	x, y, - 1 + z
Zn···H18	2.93	- 1 + x, y, z
Zn···C18	3.871 (8)	- 1 + x, y, z
O2···H22B	2.56	x, y, - 1 + z
C6···H28	2.74	1 - x, - y, - z
C7···H28	2.85	1 - x, - y, - z
C15···H27	2.80	1 - x, - y, - z
C17···H38	2.79	1 + x, y, z
C24···H17	2.78	- 1 + x, y, z
C26···H34	2.81	1 - x, - y, - z
C30···H35	2.84	1 - x, - y, - z
C31···H34	2.80	1 - x, - y, - z
C36···H16	2.85	1 - x, - y, - z
C37···H16	2.83	1 - x, - y, - z

Percentage contributions of inter-atomic contacts to the Hirshfeld surface for (I) top

Contact	Percentage contribution
H···H	56.1
C···H/H···C	23.1
S···H/H···S	9.0
O···H/H···O	5.4
N···H/H···N	1.6
C···S/S···C	1.3
C···N/N···C	1.1
Zn···H/H···Zn	0.6
Zn···C/C···Zn	0.6
C···C	0.6
C···O/O···C	0.3
N···O/O···N	0.3

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Bis(4-meth­oxy­chalcone 4-ethyl­thio­semi­carbazon­ato-κ2N1,S)zinc(II): crystal structure and Hirshfeld surface analysis

Supporting information

Key indicators

checkCIF/PLATON results

Bis(4-methoxychalcone 4-ethylthiosemicarbazonato-κ²N¹,S)zinc(II): crystal structure and Hirshfeld surface analysis