Di-n-but­yl[N′-(3-meth­oxy-2-oxidobenzyl­idene)-N-phenyl­carbamohydrazono­thio­ato]tin(IV): crystal structure, Hirshfeld surface analysis and computational study

Yusof, E.N.M.; Kwong, H.C.; Karunakaran, T.; Ravoof, T.B.S.A.; Tiekink, E.R.T.

doi:10.1107/S2056989021001870

Di-n-butyl[N′-(3-methoxy-2-oxidobenzylidene)-N-phenylcarbamohydrazonothioato]tin(IV): crystal structure, Hirshfeld surface analysis and computational study

E. N. M. Yusof, H. C. Kwong, T. Karunakaran, T. B. S. A. Ravoof and E. R. T. Tiekink

The C₂NOS donor set about the tin atom in the title compound has a geometry intermediate between trigonal–bipyramidal and square-pyramidal. In the crystal, a helical, supramolecular chain along the b-axis direction features amine-N—H

O(methoxy) hydrogen bonding.

Keywords: crystal structure; organotin; Schiff base; thiosemicarbazone; hydrogen bonding; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021001870/hb7969sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989021001870/hb7969Isup2.hkl Contains datablock I

CCDC reference: 2063179

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R factor = 0.033
wR factor = 0.076
Data-to-parameter ratio = 21.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         13 Note

Author Response: The theta~min~ was set, presumably automatically, by the software at 3.8 deg. While this value is relatively high, it is not excessively so. The "missing" reflections are unlikely to have a detrimental influence upon the refinement/chemical model.


Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.14 Report
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.01A   From Sn              1.59 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        688 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Di-n-butyl[N'-(3-methoxy-2-oxidobenzylidene)-N-phenylcarbamohydrazonothioato]tin(IV) top

Crystal data top

[Sn(C₄H₉)₂(C₁₅H₁₃N₃O₂S)]	F(000) = 1088
M_r = 532.26	D_x = 1.455 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.2720 (3) Å	Cell parameters from 9470 reflections
b = 16.1954 (3) Å	θ = 3.8–28.9°
c = 14.2778 (3) Å	µ = 1.16 mm⁻¹
β = 111.180 (3)°	T = 150 K
V = 2430.41 (10) Å³	Prism, yellow
Z = 4	0.15 × 0.10 × 0.06 mm

Data collection top

Rigaku Oxford Diffraction Xcalibur, Eos, Gemini diffractometer	5967 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	4699 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 16.1952 pixels mm^-1	θ_max = 29.3°, θ_min = 3.8°
ω scans	h = −15→14
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −21→22
T_min = 0.850, T_max = 1.000	l = −19→18
26999 measured reflections

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)] = 0.033	Hydrogen site location: mixed
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0297P)² + 1.1545P] where P = (F_o² + 2F_c²)/3
5967 reflections	(Δ/σ)_max = 0.001
277 parameters	Δρ_max = 1.63 e Å⁻³
1 restraint	Δρ_min = −0.52 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
Sn	0.30782 (2)	0.63922 (2)	0.20843 (2)	0.02658 (7)
S1	0.17922 (7)	0.76839 (5)	0.21316 (5)	0.03737 (18)
O1	0.41536 (16)	0.53123 (10)	0.26242 (13)	0.0299 (4)
O2	0.55992 (16)	0.40842 (10)	0.25269 (13)	0.0279 (4)
N1	0.3367 (2)	0.74015 (12)	0.40760 (15)	0.0271 (5)
N2	0.38235 (19)	0.67314 (12)	0.36939 (15)	0.0245 (5)
N3	0.1999 (2)	0.85096 (13)	0.37649 (16)	0.0278 (5)
H3N	0.142 (2)	0.8768 (15)	0.3282 (15)	0.033*
C1	0.2476 (2)	0.78406 (15)	0.34279 (18)	0.0267 (6)
C2	0.4807 (2)	0.63876 (15)	0.43827 (19)	0.0266 (5)
H2	0.507201	0.663195	0.503089	0.032*
C3	0.5533 (2)	0.56903 (15)	0.42817 (18)	0.0253 (5)
C4	0.5195 (2)	0.51976 (14)	0.34156 (18)	0.0231 (5)
C5	0.5993 (2)	0.45193 (15)	0.34154 (18)	0.0240 (5)
C6	0.7057 (2)	0.43422 (16)	0.4235 (2)	0.0315 (6)
H6	0.758465	0.388936	0.421749	0.038*
C7	0.7367 (3)	0.48344 (17)	0.5104 (2)	0.0373 (7)
H7	0.809490	0.470558	0.567769	0.045*
C8	0.6629 (2)	0.54928 (16)	0.51260 (19)	0.0320 (6)
H8	0.685130	0.582370	0.571384	0.038*
C9	0.6339 (3)	0.33893 (18)	0.2478 (2)	0.0414 (7)
H9A	0.720214	0.356915	0.256299	0.062*
H9B	0.595020	0.311870	0.182395	0.062*
H9C	0.637687	0.299962	0.301309	0.062*
C10	0.2229 (2)	0.87931 (15)	0.47493 (19)	0.0246 (5)
C11	0.3071 (3)	0.84289 (16)	0.5628 (2)	0.0321 (6)
H11	0.356486	0.796350	0.559100	0.039*
C12	0.3174 (3)	0.87544 (17)	0.6549 (2)	0.0355 (7)
H12	0.374328	0.850489	0.714380	0.043*
C13	0.2475 (3)	0.94306 (17)	0.6629 (2)	0.0353 (6)
H13	0.254424	0.963702	0.726972	0.042*
C14	0.1671 (3)	0.98029 (17)	0.5762 (2)	0.0331 (6)
H14	0.119945	1.027809	0.580593	0.040*
C15	0.1547 (2)	0.94894 (16)	0.4831 (2)	0.0286 (6)
H15	0.099062	0.975153	0.424064	0.034*
C16	0.1475 (2)	0.56202 (17)	0.13464 (19)	0.0320 (6)
H16A	0.073373	0.597705	0.099569	0.038*
H16B	0.165615	0.529157	0.082891	0.038*
C17	0.1111 (3)	0.50319 (18)	0.2027 (2)	0.0368 (7)
H17A	0.078865	0.535372	0.247468	0.044*
H17B	0.187726	0.472697	0.245367	0.044*
C18	0.0095 (3)	0.44156 (18)	0.1427 (2)	0.0408 (7)
H18A	−0.067397	0.472273	0.101010	0.049*
H18B	0.041312	0.410471	0.096902	0.049*
C19	−0.0267 (3)	0.3812 (2)	0.2085 (3)	0.0630 (11)
H19A	0.046823	0.346452	0.244721	0.095*
H19B	−0.096854	0.346334	0.166641	0.095*
H19C	−0.053386	0.411610	0.256866	0.095*
C20	0.4355 (3)	0.68370 (17)	0.1396 (2)	0.0348 (6)
H20A	0.510109	0.708354	0.192719	0.042*
H20B	0.466511	0.635693	0.112094	0.042*
C21	0.3833 (3)	0.74679 (18)	0.0563 (2)	0.0385 (7)
H21A	0.345417	0.793150	0.081061	0.046*
H21B	0.314902	0.720923	−0.000729	0.046*
C22	0.4850 (3)	0.7805 (2)	0.0194 (2)	0.0487 (8)
H22A	0.555087	0.804035	0.077308	0.058*
H22B	0.520427	0.734251	−0.007521	0.058*
C23	0.4367 (5)	0.8464 (2)	−0.0612 (3)	0.0684 (11)
H23A	0.360725	0.826100	−0.115308	0.103*
H23B	0.502935	0.859307	−0.088338	0.103*
H23C	0.415227	0.896385	−0.031958	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.02994 (10)	0.02799 (11)	0.01860 (10)	0.00565 (7)	0.00492 (7)	−0.00006 (7)
S1	0.0463 (4)	0.0399 (4)	0.0204 (3)	0.0194 (3)	0.0054 (3)	0.0010 (3)
O1	0.0297 (9)	0.0269 (9)	0.0246 (9)	0.0067 (7)	−0.0003 (7)	−0.0032 (7)
O2	0.0323 (9)	0.0233 (9)	0.0253 (9)	0.0031 (7)	0.0069 (8)	−0.0037 (7)
N1	0.0342 (12)	0.0242 (11)	0.0205 (11)	0.0081 (9)	0.0068 (9)	−0.0008 (9)
N2	0.0308 (11)	0.0213 (10)	0.0201 (11)	0.0058 (9)	0.0076 (9)	−0.0001 (8)
N3	0.0339 (12)	0.0270 (12)	0.0213 (11)	0.0122 (9)	0.0086 (9)	0.0040 (9)
C1	0.0315 (13)	0.0262 (13)	0.0229 (13)	0.0041 (11)	0.0104 (11)	0.0024 (10)
C2	0.0313 (13)	0.0267 (13)	0.0191 (12)	0.0018 (11)	0.0059 (10)	−0.0007 (10)
C3	0.0277 (12)	0.0239 (13)	0.0221 (13)	0.0028 (10)	0.0065 (10)	0.0027 (10)
C4	0.0235 (12)	0.0219 (12)	0.0223 (13)	0.0006 (10)	0.0062 (10)	0.0014 (10)
C5	0.0275 (12)	0.0211 (12)	0.0225 (13)	−0.0022 (10)	0.0079 (10)	−0.0009 (10)
C6	0.0323 (14)	0.0263 (14)	0.0337 (15)	0.0081 (11)	0.0093 (12)	0.0002 (11)
C7	0.0353 (15)	0.0399 (16)	0.0259 (15)	0.0094 (12)	−0.0019 (12)	−0.0005 (12)
C8	0.0353 (14)	0.0299 (14)	0.0224 (13)	0.0051 (11)	0.0004 (11)	−0.0045 (11)
C9	0.0522 (18)	0.0321 (15)	0.0359 (17)	0.0140 (13)	0.0109 (14)	−0.0065 (13)
C10	0.0283 (12)	0.0249 (13)	0.0225 (13)	0.0001 (10)	0.0114 (10)	0.0011 (10)
C11	0.0428 (16)	0.0264 (14)	0.0266 (14)	0.0062 (11)	0.0119 (12)	0.0015 (11)
C12	0.0498 (17)	0.0332 (15)	0.0219 (14)	0.0005 (13)	0.0108 (12)	0.0007 (11)
C13	0.0468 (17)	0.0341 (15)	0.0292 (15)	−0.0028 (13)	0.0187 (13)	−0.0071 (12)
C14	0.0334 (14)	0.0320 (14)	0.0391 (16)	0.0016 (12)	0.0193 (13)	−0.0049 (12)
C15	0.0268 (13)	0.0303 (14)	0.0295 (14)	0.0034 (11)	0.0111 (11)	0.0024 (11)
C16	0.0296 (13)	0.0392 (15)	0.0215 (13)	0.0030 (12)	0.0024 (11)	0.0001 (12)
C17	0.0366 (15)	0.0454 (17)	0.0230 (14)	0.0027 (13)	0.0041 (11)	0.0043 (12)
C18	0.0341 (15)	0.0447 (17)	0.0377 (17)	0.0015 (13)	0.0059 (13)	0.0018 (14)
C19	0.048 (2)	0.059 (2)	0.071 (3)	−0.0058 (17)	0.0099 (19)	0.0203 (19)
C20	0.0392 (15)	0.0353 (15)	0.0329 (16)	0.0039 (12)	0.0168 (13)	−0.0008 (12)
C21	0.0435 (16)	0.0439 (17)	0.0300 (15)	0.0005 (13)	0.0155 (13)	−0.0009 (13)
C22	0.059 (2)	0.056 (2)	0.0358 (17)	−0.0094 (17)	0.0237 (16)	−0.0045 (15)
C23	0.106 (3)	0.060 (2)	0.055 (2)	−0.008 (2)	0.048 (2)	0.0049 (19)

Geometric parameters (Å, º) top

Sn—S1	2.5598 (7)	C11—H11	0.9500
Sn—O1	2.1089 (16)	C12—C13	1.378 (4)
Sn—N2	2.212 (2)	C12—H12	0.9500
Sn—C16	2.136 (3)	C13—C14	1.381 (4)
Sn—C20	2.140 (3)	C13—H13	0.9500
S1—C1	1.747 (3)	C14—C15	1.382 (4)
O1—C4	1.316 (3)	C14—H14	0.9500
O2—C5	1.377 (3)	C15—H15	0.9500
O2—C9	1.417 (3)	C16—C17	1.519 (4)
N1—C1	1.304 (3)	C16—H16A	0.9900
N1—N2	1.394 (3)	C16—H16B	0.9900
N2—C2	1.311 (3)	C17—C18	1.528 (4)
N3—C1	1.371 (3)	C17—H17A	0.9900
N3—C10	1.411 (3)	C17—H17B	0.9900
N3—H3N	0.866 (10)	C18—C19	1.510 (4)
C2—C3	1.432 (3)	C18—H18A	0.9900
C2—H2	0.9500	C18—H18B	0.9900
C3—C4	1.404 (3)	C19—H19A	0.9800
C3—C8	1.416 (3)	C19—H19B	0.9800
C4—C5	1.420 (3)	C19—H19C	0.9800
C5—C6	1.370 (3)	C20—C21	1.516 (4)
C6—C7	1.408 (4)	C20—H20A	0.9900
C6—H6	0.9500	C20—H20B	0.9900
C7—C8	1.359 (4)	C21—C22	1.525 (4)
C7—H7	0.9500	C21—H21A	0.9900
C8—H8	0.9500	C21—H21B	0.9900
C9—H9A	0.9800	C22—C23	1.519 (5)
C9—H9B	0.9800	C22—H22A	0.9900
C9—H9C	0.9800	C22—H22B	0.9900
C10—C15	1.393 (3)	C23—H23A	0.9800
C10—C11	1.400 (4)	C23—H23B	0.9800
C11—C12	1.382 (4)	C23—H23C	0.9800

S1—Sn—O1	157.56 (5)	C11—C12—H12	119.1
S1—Sn—N2	77.04 (5)	C12—C13—C14	118.8 (3)
S1—Sn—C16	96.03 (8)	C12—C13—H13	120.6
S1—Sn—C20	102.61 (8)	C14—C13—H13	120.6
O1—Sn—N2	82.75 (7)	C13—C14—C15	120.5 (3)
O1—Sn—C16	88.11 (8)	C13—C14—H14	119.8
O1—Sn—C20	93.08 (9)	C15—C14—H14	119.8
N2—Sn—C16	126.42 (9)	C14—C15—C10	120.7 (2)
N2—Sn—C20	109.11 (10)	C14—C15—H15	119.6
C16—Sn—C20	124.08 (11)	C10—C15—H15	119.6
C1—S1—Sn	96.29 (8)	C17—C16—Sn	115.28 (17)
C4—O1—Sn	130.37 (15)	C17—C16—H16A	108.5
C5—O2—C9	116.9 (2)	Sn—C16—H16A	108.5
C1—N1—N2	116.5 (2)	C17—C16—H16B	108.5
C2—N2—N1	111.6 (2)	Sn—C16—H16B	108.5
C2—N2—Sn	125.07 (17)	H16A—C16—H16B	107.5
N1—N2—Sn	123.00 (14)	C16—C17—C18	111.8 (2)
C1—N3—C10	130.7 (2)	C16—C17—H17A	109.2
C1—N3—H3N	112.2 (19)	C18—C17—H17A	109.2
C10—N3—H3N	116.8 (19)	C16—C17—H17B	109.2
N1—C1—N3	118.8 (2)	C18—C17—H17B	109.2
N1—C1—S1	127.2 (2)	H17A—C17—H17B	107.9
N3—C1—S1	114.06 (17)	C19—C18—C17	113.0 (3)
N2—C2—C3	128.2 (2)	C19—C18—H18A	109.0
N2—C2—H2	115.9	C17—C18—H18A	109.0
C3—C2—H2	115.9	C19—C18—H18B	109.0
C4—C3—C8	119.8 (2)	C17—C18—H18B	109.0
C4—C3—C2	123.6 (2)	H18A—C18—H18B	107.8
C8—C3—C2	116.5 (2)	C18—C19—H19A	109.5
O1—C4—C3	123.4 (2)	C18—C19—H19B	109.5
O1—C4—C5	118.6 (2)	H19A—C19—H19B	109.5
C3—C4—C5	118.0 (2)	C18—C19—H19C	109.5
C6—C5—O2	124.8 (2)	H19A—C19—H19C	109.5
C6—C5—C4	121.4 (2)	H19B—C19—H19C	109.5
O2—C5—C4	113.7 (2)	C21—C20—Sn	116.88 (19)
C5—C6—C7	119.7 (2)	C21—C20—H20A	108.1
C5—C6—H6	120.1	Sn—C20—H20A	108.1
C7—C6—H6	120.1	C21—C20—H20B	108.1
C8—C7—C6	120.4 (2)	Sn—C20—H20B	108.1
C8—C7—H7	119.8	H20A—C20—H20B	107.3
C6—C7—H7	119.8	C20—C21—C22	112.7 (3)
C7—C8—C3	120.7 (2)	C20—C21—H21A	109.1
C7—C8—H8	119.7	C22—C21—H21A	109.1
C3—C8—H8	119.7	C20—C21—H21B	109.1
O2—C9—H9A	109.5	C22—C21—H21B	109.1
O2—C9—H9B	109.5	H21A—C21—H21B	107.8
H9A—C9—H9B	109.5	C23—C22—C21	113.9 (3)
O2—C9—H9C	109.5	C23—C22—H22A	108.8
H9A—C9—H9C	109.5	C21—C22—H22A	108.8
H9B—C9—H9C	109.5	C23—C22—H22B	108.8
C15—C10—C11	118.8 (2)	C21—C22—H22B	108.8
C15—C10—N3	116.0 (2)	H22A—C22—H22B	107.7
C11—C10—N3	125.2 (2)	C22—C23—H23A	109.5
C12—C11—C10	119.2 (3)	C22—C23—H23B	109.5
C12—C11—H11	120.4	H23A—C23—H23B	109.5
C10—C11—H11	120.4	C22—C23—H23C	109.5
C13—C12—C11	121.9 (3)	H23A—C23—H23C	109.5
C13—C12—H12	119.1	H23B—C23—H23C	109.5

C1—N1—N2—C2	173.0 (2)	O1—C4—C5—O2	4.0 (3)
C1—N1—N2—Sn	−1.2 (3)	C3—C4—C5—O2	−178.7 (2)
N2—N1—C1—N3	−179.6 (2)	O2—C5—C6—C7	179.8 (2)
N2—N1—C1—S1	−0.2 (4)	C4—C5—C6—C7	0.7 (4)
C10—N3—C1—N1	−6.2 (4)	C5—C6—C7—C8	−1.3 (4)
C10—N3—C1—S1	174.3 (2)	C6—C7—C8—C3	0.6 (5)
Sn—S1—C1—N1	1.1 (3)	C4—C3—C8—C7	0.7 (4)
Sn—S1—C1—N3	−179.43 (18)	C2—C3—C8—C7	179.1 (3)
N1—N2—C2—C3	180.0 (2)	C1—N3—C10—C15	−177.9 (3)
Sn—N2—C2—C3	−6.0 (4)	C1—N3—C10—C11	1.8 (4)
N2—C2—C3—C4	−7.4 (4)	C15—C10—C11—C12	1.8 (4)
N2—C2—C3—C8	174.2 (3)	N3—C10—C11—C12	−177.9 (3)
Sn—O1—C4—C3	26.6 (4)	C10—C11—C12—C13	−0.2 (4)
Sn—O1—C4—C5	−156.24 (18)	C11—C12—C13—C14	−1.5 (4)
C8—C3—C4—O1	175.9 (2)	C12—C13—C14—C15	1.6 (4)
C2—C3—C4—O1	−2.4 (4)	C13—C14—C15—C10	0.0 (4)
C8—C3—C4—C5	−1.2 (4)	C11—C10—C15—C14	−1.7 (4)
C2—C3—C4—C5	−179.5 (2)	N3—C10—C15—C14	178.0 (2)
C9—O2—C5—C6	1.9 (4)	Sn—C16—C17—C18	−171.27 (19)
C9—O2—C5—C4	−179.0 (2)	C16—C17—C18—C19	178.9 (3)
O1—C4—C5—C6	−176.8 (2)	Sn—C20—C21—C22	174.5 (2)
C3—C4—C5—C6	0.5 (4)	C20—C21—C22—C23	−177.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the (C10–C15) ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2ⁱ	0.87 (2)	2.21 (2)	2.990 (3)	150 (2)
C18—H18A···Cg1ⁱⁱ	0.99	2.81	3.730 (3)	154

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x−1/2, −y+3/2, z−1/2.

A summary of short interatomic contacts (Å) for (I)^a top

Contact	Distance	Symmetry operation
N3—H3N···O2	2.09	-x + 1/2, y + 1/2, -z + 1/2
C18—H18A···Cg1	2.81	x - 1/2, -y - 3/2, z - 1/2
C22—H22B···Cg1	3.28	x + 1/2, -y + 3/2, z - 1/2
H6···H22A	2.32	-x + 3/2, y - 1/2, -z + 1/2
H7···H17A	2.32	-x + 1, -y + 1, -z + 1

Note: (a) The interatomic distances are calculated in Crystal Explorer 17 (Turner et al., 2017) with the X—H bond lengths adjusted to their neutron values.

A summary of interaction energies (kJ mol^-1) calculated for (I) top

Contact	R (Å)	E_ele	E_pol	E_dis	E_rep	E_tot
Intra-layer region
N3—H3N···O2ⁱ	8.36	-51.6	-10.0	-77.3	74.2	-83.4
H7···H17A^iv +
H9C···H11^iv +
H9C···H12^iv	7.54	-30.2	-3.3	-88.0	78.5	-62.5
C18—H18A···Cg1ⁱⁱ+
H8···H21A^v	7.93	-19.5	-2.6	-49.7	43.0	-39.2
H16A···H18B^vi +
H16B···H18A^vi	10.52	-4.3	-0.1	-24.5	18.6	-14.5

Inter-layer region
C22—H22B···Cg1ⁱⁱⁱ	11.00	-6.8	-1.3	-32.0	16.7	-25.7
H9A···H22B^vii+
H9A···H23A^vii	11.46	-2.9	-0.7	-18.7	12.0	-12.6
H14···H15^viii	15.83	-6.7	-0.7	-14.1	18.3	-8.6
H6···H22A^ix+
H7···H23B^ix	12.63	-1.5	-0.4	-11.6	6.0	-8.3
H9A···H19C^x	11.27	-1.3	-0.2	-6.4	3.1	-5.2
H12···H23A^xi	14.28	-2.2	-0.1	-7.2	6.1	-4.9

Symmetry operations: (i) -x + 1/2, y + 1/2, -z + 1/2; (ii) x - 1/2, -y + 3/2, z - 1/2; (iii) x + 1/2, -y + 3/2, z - 1/2; (iv) -x + 1, -y + 1, -z + 1; (v) x + 1/2, -y + 3/2, z + 1/2; (vi) -x, -y + 1, -z; (vii) -x + 1, -y + 1, -z; (viii) -x, -y + 2, -z + 1; (ix) -x + 3/2, y - 1/2, -z + 1/2; (x) x + 1, y, z; (xi) x, y, z + 1.

A comparison of key geometric parameters (Å, °) in structures related to (I). top

Compound	R, R'	Sn—S	Sn—O1	Sn—N2	S1—Sn—O1	C—Sn—C	τ	Ref.
(I)	nBu, nBu	2.5598 (7)	2.1089 (16)	2.212 (2)	157.56 (5)	124.08 (11)	0.52	This work
(II)	Me, Me	2.4982 (12)	2.085 (3)	2.257 (3)	145.67 (9)	114.82 (18)	0.00	Yusof et al. (2020)
(III)	Ph, Ph	2.5475 (8)	2.0853 (19)	2.176 (3)	161.81 (7)	121.46 (12)	0.60	Yusof et al. (2020)
(IV)^a	nBu, CH₂SiM₃	2.485 (5)	2.152 (6)	2.184 (6)	159.4 (2)	121.6 (4)	0.60	Xie et al. (2020)
(IV)^b		2.587 (4)	2.063 (6)	2.218 (7)	157.6 (3)	123.8 (4)	0.56

Notes: (a) major component of the disorder with a site occupancy = 0.527 and (b) minor component with occupancy 0.473.

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Di-n-but­yl[N′-(3-meth­oxy-2-oxidobenzyl­idene)-N-phenyl­carbamohydrazono­thio­ato]tin(IV): crystal structure, Hirshfeld surface analysis and computational study

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Di-n-butyl[N′-(3-methoxy-2-oxidobenzylidene)-N-phenylcarbamohydrazonothioato]tin(IV): crystal structure, Hirshfeld surface analysis and computational study