Distinct coordination geometries in bis­[N,N-bis­(2-meth­oxy­eth­yl)di­thio­carbamato-κ²S,S′]di­phenyltin(IV) and bis­[N-(2-meth­oxy­eth­yl)-N-methyl­dithio­carbamato-κ²S,S′]di­phenyl­tin(IV): crystal structures and Hirshfeld surface analysis

Two distinct coordination geometries, each based on a C₂S₄ donor set, are found in the title compounds, being based on an octa­hedron in (C₆H₅)₂Sn(S₂CN(Me)CH₂CH₂OMe)₂ and a skew trapezoidal bipyramid in (C₆H₅)₂Sn[S₂CN(CH₂CH₂OMe)₂]₂.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.026
• wR factor = 0.063
• Data-to-parameter ratio = 23.7

Structure: II

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.031
• wR factor = 0.078
• Data-to-parameter ratio = 24.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           7 Note

Alert level G
PLAT069_ALERT_1_G Atom Label without Numerical Part ..............         Sn Do !
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Sn     --  S1      ..       10.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Sn     --  S2      ..       23.3 s.u.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        479 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           5 Note

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

   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


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

Author Response: The theta range for the data collection was 3.3 to 30.4 \deg, presumably set by CrysAlis PRO. While a little high, this is unlikely to be detrimental to the model.

Alert level C
PLAT220_ALERT_2_C Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        3.6 Ratio
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C23 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C21 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C31 Check
PLAT331_ALERT_2_C Small Average Phenyl   C-C Dist. C21    -C26           1.37 Ang.

Alert level G
PLAT069_ALERT_1_G Atom Label without Numerical Part ..............         Sn Do !
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Sn     --  S2      ..        7.7 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Sn     --  S4      ..        7.3 s.u.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600       1301 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           1 Note

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

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

---

Computing details

For both compounds, data collection: CrysAlis PRO (Agilent, 2015); cell refinement: CrysAlis PRO (Agilent, 2015); data reduction: CrysAlis PRO (Agilent, 2015); program(s) used to solve structure: SHELXL97 (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) for (I); SHELXL2014 (Sheldrick, 2015) for (II).

(I) Bis[N,N-bis(2-methoxyethyl)dithiocarbamato-κ²S,S']diphenyltin(IV)

Crystal data

[Sn(C6H5)2(C5H10NOS2)2]	F(000) = 1224
Mr = 601.41	Dx = 1.559 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.3808 (14) Å	Cell parameters from 3633 reflections
b = 8.2809 (4) Å	θ = 4.2–29.9°
c = 19.083 (3) Å	µ = 1.34 mm^−1
β = 118.071 (8)°	T = 293 K
V = 2562.9 (5) Å^3	Block, colourless
Z = 4	0.25 × 0.25 × 0.20 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	3383 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3051 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 10.4041 pixels mm^-1	θmax = 30.4°, θmin = 4.0°
ω scan	h = −26→18
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2015)	k = −11→11
Tmin = 0.815, Tmax = 1.000	l = −25→26
7357 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.063	w = 1/[σ^2(Fo^2) + (0.0284P)^2 + 0.8262P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3383 reflections	Δρmax = 0.47 e Å^−3
143 parameters	Δρmin = −0.30 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Sn	0.5000	0.56549 (2)	0.7500	0.03252 (7)
S1	0.65567 (3)	0.64166 (6)	0.82876 (3)	0.04210 (12)
S2	0.52661 (3)	0.81055 (7)	0.84973 (4)	0.04728 (13)
O1	0.77790 (11)	1.16594 (19)	0.88988 (10)	0.0563 (4)
N1	0.68188 (11)	0.90857 (19)	0.91561 (10)	0.0391 (4)
C1	0.62737 (11)	0.8001 (2)	0.87001 (11)	0.0350 (4)
C2	0.65719 (17)	1.0454 (3)	0.94849 (16)	0.0568 (6)
H2A	0.6227	1.1170	0.9063	0.068*
H2B	0.7054	1.1024	0.9858	0.068*
H2C	0.6273	1.0063	0.9749	0.068*
C3	0.76876 (13)	0.9020 (3)	0.93400 (13)	0.0458 (5)
H3A	0.7836	0.7905	0.9316	0.055*
H3B	0.8025	0.9398	0.9879	0.055*
C4	0.78779 (13)	1.0011 (3)	0.87883 (13)	0.0464 (5)
H4A	0.8440	0.9808	0.8893	0.056*
H4B	0.7511	0.9709	0.8243	0.056*
C5	0.80091 (16)	1.2685 (3)	0.84467 (16)	0.0630 (7)
H5A	0.8589	1.2570	0.8620	0.095*
H5B	0.7890	1.3784	0.8516	0.095*
H5C	0.7705	1.2398	0.7896	0.095*
C11	0.52133 (11)	0.3974 (2)	0.67451 (11)	0.0337 (4)
C12	0.57526 (14)	0.2710 (3)	0.71091 (13)	0.0470 (5)
H12	0.6002	0.2605	0.7659	0.056*
C13	0.59275 (15)	0.1597 (3)	0.66667 (15)	0.0552 (6)
H13	0.6294	0.0758	0.6920	0.066*
C14	0.55615 (14)	0.1732 (3)	0.58582 (15)	0.0525 (6)
H14	0.5679	0.0986	0.5561	0.063*
C15	0.50225 (14)	0.2964 (3)	0.54873 (13)	0.0512 (5)
H15	0.4771	0.3052	0.4937	0.061*
C16	0.48494 (13)	0.4085 (3)	0.59275 (12)	0.0425 (4)
H16	0.4483	0.4923	0.5669	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn	0.03241 (10)	0.03268 (10)	0.03421 (10)	0.000	0.01712 (7)	0.000
S1	0.0349 (2)	0.0430 (3)	0.0492 (3)	0.0002 (2)	0.0205 (2)	−0.0098 (2)
S2	0.0413 (3)	0.0423 (3)	0.0667 (4)	−0.0031 (2)	0.0324 (3)	−0.0114 (2)
O1	0.0732 (11)	0.0438 (8)	0.0706 (11)	−0.0030 (8)	0.0492 (9)	0.0028 (7)
N1	0.0423 (9)	0.0359 (8)	0.0404 (9)	−0.0064 (7)	0.0205 (7)	−0.0038 (7)
C1	0.0380 (9)	0.0340 (9)	0.0363 (9)	−0.0004 (8)	0.0202 (8)	0.0018 (7)
C2	0.0753 (17)	0.0458 (12)	0.0653 (15)	−0.0149 (12)	0.0464 (14)	−0.0188 (11)
C3	0.0362 (10)	0.0428 (11)	0.0470 (12)	−0.0037 (9)	0.0102 (8)	0.0021 (9)
C4	0.0399 (10)	0.0475 (11)	0.0539 (12)	−0.0014 (10)	0.0238 (9)	−0.0044 (10)
C5	0.0649 (16)	0.0613 (15)	0.0704 (17)	−0.0060 (13)	0.0381 (13)	0.0137 (13)
C11	0.0331 (9)	0.0349 (9)	0.0345 (9)	−0.0020 (8)	0.0171 (7)	−0.0019 (7)
C12	0.0529 (12)	0.0457 (11)	0.0374 (10)	0.0098 (10)	0.0169 (9)	0.0000 (9)
C13	0.0552 (13)	0.0432 (12)	0.0634 (15)	0.0122 (11)	0.0248 (11)	−0.0053 (10)
C14	0.0552 (13)	0.0515 (13)	0.0627 (14)	−0.0112 (11)	0.0377 (11)	−0.0230 (11)
C15	0.0549 (13)	0.0636 (14)	0.0371 (11)	−0.0127 (12)	0.0234 (9)	−0.0111 (10)
C16	0.0391 (10)	0.0483 (11)	0.0371 (10)	0.0014 (9)	0.0153 (8)	0.0016 (8)

Geometric parameters (Å, º)

Sn—C11	2.1677 (18)	C3—H3B	0.9700
Sn—C11^i	2.1678 (18)	C4—H4A	0.9700
Sn—S1	2.6071 (6)	C4—H4B	0.9700
Sn—S1^i	2.6071 (6)	C5—H5A	0.9600
Sn—S2^i	2.6653 (6)	C5—H5B	0.9600
Sn—S2	2.6653 (6)	C5—H5C	0.9600
S1—C1	1.7311 (19)	C11—C16	1.381 (3)
S2—C1	1.7067 (19)	C11—C12	1.383 (3)
O1—C4	1.406 (3)	C12—C13	1.386 (3)
O1—C5	1.410 (3)	C12—H12	0.9300
N1—C1	1.322 (2)	C13—C14	1.367 (3)
N1—C3	1.466 (3)	C13—H13	0.9300
N1—C2	1.467 (3)	C14—C15	1.365 (3)
C2—H2A	0.9600	C14—H14	0.9300
C2—H2B	0.9600	C15—C16	1.386 (3)
C2—H2C	0.9600	C15—H15	0.9300
C3—C4	1.500 (3)	C16—H16	0.9300
C3—H3A	0.9700
C11—Sn—C11^i	100.07 (10)	N1—C3—H3B	108.9
C11—Sn—S1	92.63 (5)	C4—C3—H3B	108.9
C11^i—Sn—S1	105.36 (5)	H3A—C3—H3B	107.7
C11—Sn—S1^i	105.36 (5)	O1—C4—C3	109.68 (18)
C11^i—Sn—S1^i	92.63 (5)	O1—C4—H4A	109.7
S1—Sn—S1^i	152.00 (2)	C3—C4—H4A	109.7
C11—Sn—S2^i	92.54 (5)	O1—C4—H4B	109.7
C11^i—Sn—S2^i	159.03 (5)	C3—C4—H4B	109.7
S1—Sn—S2^i	90.591 (19)	H4A—C4—H4B	108.2
S1^i—Sn—S2^i	67.742 (17)	O1—C5—H5A	109.5
C11—Sn—S2	159.03 (5)	O1—C5—H5B	109.5
C11^i—Sn—S2	92.54 (5)	H5A—C5—H5B	109.5
S1—Sn—S2	67.744 (17)	O1—C5—H5C	109.5
S1^i—Sn—S2	90.590 (19)	H5A—C5—H5C	109.5
S2^i—Sn—S2	80.82 (3)	H5B—C5—H5C	109.5
C1—S1—Sn	87.84 (6)	C16—C11—C12	118.01 (18)
C1—S2—Sn	86.46 (7)	C16—C11—Sn	124.38 (14)
C4—O1—C5	113.31 (18)	C12—C11—Sn	117.61 (14)
C1—N1—C3	122.35 (17)	C11—C12—C13	120.9 (2)
C1—N1—C2	121.01 (18)	C11—C12—H12	119.5
C3—N1—C2	116.62 (18)	C13—C12—H12	119.5
N1—C1—S2	121.35 (15)	C14—C13—C12	120.1 (2)
N1—C1—S1	121.16 (14)	C14—C13—H13	120.0
S2—C1—S1	117.49 (11)	C12—C13—H13	120.0
N1—C2—H2A	109.5	C15—C14—C13	119.87 (19)
N1—C2—H2B	109.5	C15—C14—H14	120.1
H2A—C2—H2B	109.5	C13—C14—H14	120.1
N1—C2—H2C	109.5	C14—C15—C16	120.3 (2)
H2A—C2—H2C	109.5	C14—C15—H15	119.9
H2B—C2—H2C	109.5	C16—C15—H15	119.9
N1—C3—C4	113.51 (17)	C11—C16—C15	120.8 (2)
N1—C3—H3A	108.9	C11—C16—H16	119.6
C4—C3—H3A	108.9	C15—C16—H16	119.6
C3—N1—C1—S2	179.88 (15)	C5—O1—C4—C3	175.27 (19)
C2—N1—C1—S2	−2.0 (3)	N1—C3—C4—O1	67.0 (2)
C3—N1—C1—S1	0.0 (3)	C16—C11—C12—C13	0.5 (3)
C2—N1—C1—S1	178.13 (16)	Sn—C11—C12—C13	−179.24 (17)
Sn—S2—C1—N1	173.67 (16)	C11—C12—C13—C14	−0.4 (4)
Sn—S2—C1—S1	−6.47 (10)	C12—C13—C14—C15	−0.1 (3)
Sn—S1—C1—N1	−173.53 (16)	C13—C14—C15—C16	0.4 (3)
Sn—S1—C1—S2	6.60 (10)	C12—C11—C16—C15	−0.2 (3)
C1—N1—C3—C4	93.8 (2)	Sn—C11—C16—C15	179.59 (16)
C2—N1—C3—C4	−84.4 (2)	C14—C15—C16—C11	−0.3 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C11–C16 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Cg1^ii	0.97	2.86	3.730 (3)	150

Symmetry code: (ii) x+1, −y, z+1/2.

(II) Bis[N-(2-methoxyethyl)-N-methyldithiocarbamato-κ²S,S']diphenyltin(IV)

Crystal data

[Sn(C6H5)2(C7H14NO2S2)2]	Z = 2
Mr = 689.51	F(000) = 708
Triclinic, P1	Dx = 1.422 Mg m^−3
a = 7.4386 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.3334 (8) Å	Cell parameters from 6877 reflections
c = 16.5398 (10) Å	θ = 3.8–29.7°
α = 110.320 (5)°	µ = 1.09 mm^−1
β = 91.282 (5)°	T = 293 K
γ = 101.865 (4)°	Block, colourless
V = 1609.93 (17) Å^3	0.30 × 0.25 × 0.25 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	8354 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	6973 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.035
Detector resolution: 10.4041 pixels mm^-1	θmax = 30.4°, θmin = 3.3°
ω scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2015)	k = −19→19
Tmin = 0.756, Tmax = 1.000	l = −22→18
17063 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0316P)^2 + 0.0774P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
8354 reflections	Δρmax = 0.66 e Å^−3
338 parameters	Δρmin = −0.56 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Sn	0.53321 (2)	0.25616 (2)	0.25381 (2)	0.04036 (6)
S1	0.34463 (8)	0.37273 (4)	0.23099 (4)	0.05095 (14)
S2	0.75066 (8)	0.44734 (5)	0.23709 (5)	0.05550 (15)
S3	0.22105 (8)	0.15139 (4)	0.26109 (4)	0.04817 (14)
S4	0.53671 (8)	0.06041 (4)	0.27883 (4)	0.04702 (13)
O1	0.3430 (3)	0.61622 (18)	0.10117 (16)	0.1049 (8)
O2	0.6103 (3)	0.75288 (15)	0.38247 (15)	0.0899 (7)
O3	−0.0963 (3)	−0.19679 (12)	0.15238 (12)	0.0705 (5)
O4	0.1455 (3)	−0.09606 (15)	0.42343 (13)	0.0737 (5)
N1	0.5046 (3)	0.55831 (13)	0.23494 (13)	0.0504 (4)
N2	0.1846 (2)	−0.03099 (12)	0.27492 (12)	0.0426 (4)
C1	0.5361 (3)	0.46932 (15)	0.23417 (14)	0.0437 (5)
C2	0.3173 (4)	0.57560 (18)	0.22800 (18)	0.0601 (6)
H2A	0.3202	0.6469	0.2604	0.072*
H2B	0.2358	0.5348	0.2542	0.072*
C3	0.2400 (4)	0.5493 (2)	0.1363 (2)	0.0750 (8)
H3A	0.2446	0.4796	0.1022	0.090*
H3B	0.1121	0.5544	0.1349	0.090*
C4	0.2821 (6)	0.5939 (3)	0.0126 (3)	0.1359 (18)
H4A	0.2869	0.5249	−0.0211	0.204*
H4B	0.3609	0.6400	−0.0090	0.204*
H4C	0.1575	0.6016	0.0082	0.204*
C5	0.6601 (4)	0.64484 (18)	0.24329 (19)	0.0653 (7)
H5A	0.6178	0.6911	0.2202	0.078*
H5B	0.7560	0.6194	0.2093	0.078*
C6	0.7398 (4)	0.70258 (18)	0.3363 (2)	0.0707 (8)
H6A	0.7695	0.6555	0.3620	0.085*
H6B	0.8526	0.7520	0.3387	0.085*
C7	0.6699 (6)	0.8058 (3)	0.4717 (3)	0.1109 (13)
H7A	0.7157	0.7615	0.4951	0.166*
H7B	0.5680	0.8271	0.5018	0.166*
H7C	0.7665	0.8647	0.4787	0.166*
C8	0.3058 (3)	0.05076 (14)	0.27243 (13)	0.0379 (4)
C9	−0.0177 (3)	−0.03932 (16)	0.27130 (16)	0.0485 (5)
H9A	−0.0407	0.0288	0.2931	0.058*
H9B	−0.0687	−0.0744	0.3092	0.058*
C10	−0.1160 (3)	−0.09513 (17)	0.18215 (17)	0.0562 (6)
H10A	−0.2459	−0.0940	0.1833	0.067*
H10B	−0.0646	−0.0617	0.1432	0.067*
C11	−0.1881 (5)	−0.2554 (2)	0.0696 (2)	0.0932 (10)
H11A	−0.3185	−0.2603	0.0715	0.140*
H11B	−0.1642	−0.3226	0.0516	0.140*
H11C	−0.1445	−0.2235	0.0293	0.140*
C12	0.2468 (3)	−0.11869 (16)	0.28315 (16)	0.0517 (6)
H12A	0.3521	−0.1291	0.2503	0.062*
H12B	0.1485	−0.1796	0.2581	0.062*
C13	0.3001 (4)	−0.10467 (19)	0.37586 (18)	0.0602 (6)
H13A	0.3463	−0.1626	0.3775	0.072*
H13B	0.3977	−0.0436	0.4017	0.072*
C14	0.1853 (5)	−0.0891 (3)	0.5099 (2)	0.0997 (11)
H14A	0.2197	−0.1503	0.5095	0.150*
H14B	0.0779	−0.0812	0.5404	0.150*
H14C	0.2852	−0.0313	0.5383	0.150*
C21	0.6777 (3)	0.32313 (15)	0.38043 (14)	0.0465 (5)
C22	0.5984 (5)	0.3759 (3)	0.4491 (2)	0.0928 (11)
H22	0.4791	0.3839	0.4411	0.111*
C23	0.6951 (7)	0.4189 (3)	0.5326 (2)	0.1190 (14)
H23	0.6389	0.4546	0.5795	0.143*
C24	0.8694 (6)	0.4084 (3)	0.5450 (2)	0.0970 (11)
H24	0.9330	0.4362	0.6001	0.116*
C25	0.9485 (5)	0.3575 (3)	0.4769 (2)	0.0938 (10)
H25	1.0692	0.3514	0.4846	0.113*
C26	0.8533 (4)	0.3138 (2)	0.3950 (2)	0.0783 (8)
H26	0.9102	0.2773	0.3489	0.094*
C31	0.6273 (3)	0.18363 (15)	0.13244 (14)	0.0434 (5)
C32	0.7940 (4)	0.1564 (2)	0.12717 (18)	0.0705 (7)
H32	0.8682	0.1699	0.1777	0.085*
C33	0.8533 (5)	0.1092 (2)	0.0478 (2)	0.0849 (9)
H33	0.9680	0.0926	0.0452	0.102*
C34	0.7435 (5)	0.0869 (2)	−0.0269 (2)	0.0854 (10)
H34	0.7827	0.0541	−0.0802	0.102*
C35	0.5772 (5)	0.1128 (3)	−0.02322 (19)	0.0885 (9)
H35	0.5030	0.0979	−0.0741	0.106*
C36	0.5176 (4)	0.1613 (2)	0.05655 (17)	0.0679 (7)
H36	0.4037	0.1788	0.0588	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn	0.04240 (9)	0.04311 (9)	0.03293 (9)	0.01125 (6)	0.00010 (6)	0.00979 (6)
S1	0.0453 (3)	0.0431 (3)	0.0648 (4)	0.0074 (2)	−0.0022 (3)	0.0219 (3)
S2	0.0474 (3)	0.0555 (3)	0.0646 (4)	0.0082 (3)	0.0016 (3)	0.0251 (3)
S3	0.0418 (3)	0.0453 (3)	0.0620 (4)	0.0144 (2)	0.0033 (3)	0.0225 (3)
S4	0.0401 (3)	0.0506 (3)	0.0527 (3)	0.0140 (2)	0.0016 (2)	0.0195 (3)
O1	0.1032 (17)	0.1125 (17)	0.1005 (19)	−0.0200 (14)	−0.0375 (14)	0.0683 (15)
O2	0.0898 (15)	0.0732 (12)	0.0901 (16)	0.0321 (12)	−0.0235 (13)	0.0031 (11)
O3	0.0802 (13)	0.0559 (9)	0.0617 (12)	0.0067 (9)	−0.0153 (10)	0.0105 (8)
O4	0.0601 (11)	0.1001 (13)	0.0594 (12)	0.0032 (10)	−0.0044 (9)	0.0357 (11)
N1	0.0556 (11)	0.0430 (9)	0.0524 (12)	0.0066 (9)	−0.0052 (9)	0.0202 (8)
N2	0.0421 (9)	0.0402 (8)	0.0448 (11)	0.0111 (8)	0.0011 (8)	0.0136 (7)
C1	0.0486 (12)	0.0456 (11)	0.0344 (11)	0.0073 (10)	−0.0027 (9)	0.0136 (9)
C2	0.0646 (16)	0.0489 (12)	0.0689 (18)	0.0157 (12)	−0.0036 (13)	0.0227 (12)
C3	0.0669 (17)	0.0748 (17)	0.086 (2)	0.0054 (15)	−0.0199 (16)	0.0403 (16)
C4	0.133 (4)	0.164 (4)	0.107 (3)	−0.033 (3)	−0.053 (3)	0.087 (3)
C5	0.0717 (17)	0.0493 (13)	0.077 (2)	0.0013 (12)	−0.0020 (15)	0.0326 (13)
C6	0.0644 (16)	0.0480 (13)	0.090 (2)	−0.0012 (13)	−0.0163 (16)	0.0221 (13)
C7	0.108 (3)	0.094 (2)	0.100 (3)	0.030 (2)	−0.032 (2)	−0.003 (2)
C8	0.0403 (10)	0.0401 (10)	0.0314 (10)	0.0118 (9)	0.0005 (8)	0.0090 (8)
C9	0.0394 (11)	0.0484 (11)	0.0567 (15)	0.0088 (10)	0.0086 (10)	0.0182 (10)
C10	0.0425 (12)	0.0621 (14)	0.0610 (16)	0.0094 (11)	−0.0017 (11)	0.0205 (12)
C11	0.112 (3)	0.0767 (19)	0.065 (2)	−0.0041 (19)	−0.0185 (19)	0.0101 (15)
C12	0.0549 (13)	0.0387 (11)	0.0620 (16)	0.0134 (10)	0.0037 (12)	0.0172 (10)
C13	0.0572 (15)	0.0578 (13)	0.0698 (18)	0.0119 (12)	−0.0072 (13)	0.0296 (13)
C14	0.091 (2)	0.139 (3)	0.065 (2)	−0.006 (2)	−0.0112 (18)	0.051 (2)
C21	0.0552 (13)	0.0422 (10)	0.0364 (12)	0.0048 (10)	−0.0065 (10)	0.0113 (9)
C22	0.078 (2)	0.129 (3)	0.0483 (18)	0.027 (2)	−0.0008 (16)	0.0015 (18)
C23	0.134 (4)	0.152 (4)	0.0401 (19)	0.031 (3)	0.005 (2)	−0.002 (2)
C24	0.120 (3)	0.095 (2)	0.053 (2)	−0.011 (2)	−0.034 (2)	0.0211 (17)
C25	0.085 (2)	0.103 (2)	0.083 (3)	0.008 (2)	−0.038 (2)	0.032 (2)
C26	0.0730 (18)	0.093 (2)	0.0608 (19)	0.0302 (17)	−0.0145 (15)	0.0118 (15)
C31	0.0480 (12)	0.0468 (11)	0.0353 (11)	0.0125 (10)	0.0057 (9)	0.0135 (9)
C32	0.0602 (16)	0.102 (2)	0.0458 (16)	0.0309 (16)	0.0052 (13)	0.0150 (14)
C33	0.0707 (19)	0.113 (2)	0.070 (2)	0.0390 (19)	0.0278 (18)	0.0204 (18)
C34	0.099 (2)	0.102 (2)	0.0453 (18)	0.026 (2)	0.0291 (18)	0.0118 (16)
C35	0.097 (2)	0.124 (3)	0.0359 (16)	0.029 (2)	0.0013 (16)	0.0161 (16)
C36	0.0669 (16)	0.0914 (19)	0.0438 (15)	0.0282 (15)	−0.0009 (13)	0.0169 (13)

Geometric parameters (Å, º)

Sn—C31	2.124 (2)	C7—H7C	0.9600
Sn—C21	2.131 (2)	C9—C10	1.497 (3)
Sn—S1	2.5060 (6)	C9—H9A	0.9700
Sn—S3	2.5230 (6)	C9—H9B	0.9700
Sn—S4	2.9800 (6)	C10—H10A	0.9700
Sn—S2	2.9875 (6)	C10—H10B	0.9700
S1—C1	1.756 (2)	C11—H11A	0.9600
S2—C1	1.692 (2)	C11—H11B	0.9600
S3—C8	1.752 (2)	C11—H11C	0.9600
S4—C8	1.692 (2)	C12—C13	1.508 (4)
O1—C3	1.396 (3)	C12—H12A	0.9700
O1—C4	1.428 (4)	C12—H12B	0.9700
O2—C6	1.403 (3)	C13—H13A	0.9700
O2—C7	1.416 (4)	C13—H13B	0.9700
O3—C11	1.403 (3)	C14—H14A	0.9600
O3—C10	1.407 (3)	C14—H14B	0.9600
O4—C13	1.410 (3)	C14—H14C	0.9600
O4—C14	1.419 (3)	C21—C22	1.351 (4)
N1—C1	1.339 (3)	C21—C26	1.364 (4)
N1—C2	1.474 (3)	C22—C23	1.410 (5)
N1—C5	1.476 (3)	C22—H22	0.9300
N2—C8	1.337 (2)	C23—C24	1.355 (5)
N2—C12	1.472 (3)	C23—H23	0.9300
N2—C9	1.483 (3)	C24—C25	1.335 (5)
C2—C3	1.499 (4)	C24—H24	0.9300
C2—H2A	0.9700	C25—C26	1.383 (4)
C2—H2B	0.9700	C25—H25	0.9300
C3—H3A	0.9700	C26—H26	0.9300
C3—H3B	0.9700	C31—C32	1.370 (3)
C4—H4A	0.9600	C31—C36	1.383 (3)
C4—H4B	0.9600	C32—C33	1.381 (4)
C4—H4C	0.9600	C32—H32	0.9300
C5—C6	1.509 (4)	C33—C34	1.367 (5)
C5—H5A	0.9700	C33—H33	0.9300
C5—H5B	0.9700	C34—C35	1.359 (5)
C6—H6A	0.9700	C34—H34	0.9300
C6—H6B	0.9700	C35—C36	1.392 (4)
C7—H7A	0.9600	C35—H35	0.9300
C7—H7B	0.9600	C36—H36	0.9300
C31—Sn—C21	130.12 (9)	N2—C9—H9A	108.8
C31—Sn—S1	106.70 (6)	C10—C9—H9A	108.8
C21—Sn—S1	109.72 (6)	N2—C9—H9B	108.8
C31—Sn—S3	108.44 (6)	C10—C9—H9B	108.8
C21—Sn—S3	108.85 (6)	H9A—C9—H9B	107.7
S1—Sn—S3	82.873 (18)	O3—C10—C9	109.5 (2)
C31—Sn—S4	83.63 (5)	O3—C10—H10A	109.8
C21—Sn—S4	83.60 (6)	C9—C10—H10A	109.8
S1—Sn—S4	147.433 (18)	O3—C10—H10B	109.8
S3—Sn—S4	64.591 (16)	C9—C10—H10B	109.8
C31—Sn—S2	83.87 (5)	H10A—C10—H10B	108.2
C21—Sn—S2	81.92 (6)	O3—C11—H11A	109.5
S1—Sn—S2	64.922 (18)	O3—C11—H11B	109.5
S3—Sn—S2	147.742 (18)	H11A—C11—H11B	109.5
S4—Sn—S2	147.642 (17)	O3—C11—H11C	109.5
C1—S1—Sn	94.83 (7)	H11A—C11—H11C	109.5
C1—S2—Sn	80.40 (7)	H11B—C11—H11C	109.5
C8—S3—Sn	95.15 (7)	N2—C12—C13	112.95 (19)
C8—S4—Sn	81.36 (7)	N2—C12—H12A	109.0
C3—O1—C4	113.0 (3)	C13—C12—H12A	109.0
C6—O2—C7	113.3 (2)	N2—C12—H12B	109.0
C11—O3—C10	113.3 (2)	C13—C12—H12B	109.0
C13—O4—C14	112.2 (2)	H12A—C12—H12B	107.8
C1—N1—C2	122.75 (19)	O4—C13—C12	109.9 (2)
C1—N1—C5	120.5 (2)	O4—C13—H13A	109.7
C2—N1—C5	116.75 (18)	C12—C13—H13A	109.7
C8—N2—C12	121.08 (17)	O4—C13—H13B	109.7
C8—N2—C9	123.23 (17)	C12—C13—H13B	109.7
C12—N2—C9	115.69 (17)	H13A—C13—H13B	108.2
N1—C1—S2	122.83 (17)	O4—C14—H14A	109.5
N1—C1—S1	117.81 (17)	O4—C14—H14B	109.5
S2—C1—S1	119.36 (12)	H14A—C14—H14B	109.5
N1—C2—C3	113.2 (2)	O4—C14—H14C	109.5
N1—C2—H2A	108.9	H14A—C14—H14C	109.5
C3—C2—H2A	108.9	H14B—C14—H14C	109.5
N1—C2—H2B	108.9	C22—C21—C26	117.7 (3)
C3—C2—H2B	108.9	C22—C21—Sn	121.2 (2)
H2A—C2—H2B	107.8	C26—C21—Sn	121.12 (19)
O1—C3—C2	109.5 (2)	C21—C22—C23	120.5 (3)
O1—C3—H3A	109.8	C21—C22—H22	119.7
C2—C3—H3A	109.8	C23—C22—H22	119.7
O1—C3—H3B	109.8	C24—C23—C22	120.3 (3)
C2—C3—H3B	109.8	C24—C23—H23	119.8
H3A—C3—H3B	108.2	C22—C23—H23	119.8
O1—C4—H4A	109.5	C25—C24—C23	119.1 (3)
O1—C4—H4B	109.5	C25—C24—H24	120.5
H4A—C4—H4B	109.5	C23—C24—H24	120.5
O1—C4—H4C	109.5	C24—C25—C26	120.8 (3)
H4A—C4—H4C	109.5	C24—C25—H25	119.6
H4B—C4—H4C	109.5	C26—C25—H25	119.6
N1—C5—C6	112.0 (2)	C21—C26—C25	121.5 (3)
N1—C5—H5A	109.2	C21—C26—H26	119.2
C6—C5—H5A	109.2	C25—C26—H26	119.2
N1—C5—H5B	109.2	C32—C31—C36	118.6 (2)
C6—C5—H5B	109.2	C32—C31—Sn	121.56 (18)
H5A—C5—H5B	107.9	C36—C31—Sn	119.81 (17)
O2—C6—C5	109.2 (2)	C31—C32—C33	120.9 (3)
O2—C6—H6A	109.8	C31—C32—H32	119.5
C5—C6—H6A	109.8	C33—C32—H32	119.5
O2—C6—H6B	109.8	C34—C33—C32	120.0 (3)
C5—C6—H6B	109.8	C34—C33—H33	120.0
H6A—C6—H6B	108.3	C32—C33—H33	120.0
O2—C7—H7A	109.5	C35—C34—C33	120.1 (3)
O2—C7—H7B	109.5	C35—C34—H34	120.0
H7A—C7—H7B	109.5	C33—C34—H34	120.0
O2—C7—H7C	109.5	C34—C35—C36	120.1 (3)
H7A—C7—H7C	109.5	C34—C35—H35	119.9
H7B—C7—H7C	109.5	C36—C35—H35	119.9
N2—C8—S4	122.77 (15)	C31—C36—C35	120.2 (3)
N2—C8—S3	118.40 (15)	C31—C36—H36	119.9
S4—C8—S3	118.83 (11)	C35—C36—H36	119.9
N2—C9—C10	113.64 (18)
C2—N1—C1—S2	176.85 (18)	C8—N2—C9—C10	95.7 (2)
C5—N1—C1—S2	−3.4 (3)	C12—N2—C9—C10	−85.3 (2)
C2—N1—C1—S1	−3.7 (3)	C11—O3—C10—C9	178.7 (2)
C5—N1—C1—S1	176.03 (18)	N2—C9—C10—O3	63.3 (2)
Sn—S2—C1—N1	173.13 (19)	C8—N2—C12—C13	84.5 (3)
Sn—S2—C1—S1	−6.27 (11)	C9—N2—C12—C13	−94.4 (2)
Sn—S1—C1—N1	−172.02 (16)	C14—O4—C13—C12	176.3 (2)
Sn—S1—C1—S2	7.40 (13)	N2—C12—C13—O4	62.5 (3)
C1—N1—C2—C3	−90.2 (3)	C26—C21—C22—C23	−0.4 (5)
C5—N1—C2—C3	90.0 (3)	Sn—C21—C22—C23	179.4 (3)
C4—O1—C3—C2	177.9 (3)	C21—C22—C23—C24	0.4 (6)
N1—C2—C3—O1	−66.0 (3)	C22—C23—C24—C25	0.6 (7)
C1—N1—C5—C6	−81.5 (3)	C23—C24—C25—C26	−1.6 (6)
C2—N1—C5—C6	98.3 (3)	C22—C21—C26—C25	−0.6 (5)
C7—O2—C6—C5	177.4 (2)	Sn—C21—C26—C25	179.6 (2)
N1—C5—C6—O2	−68.2 (3)	C24—C25—C26—C21	1.7 (5)
C12—N2—C8—S4	−0.3 (3)	C36—C31—C32—C33	1.1 (4)
C9—N2—C8—S4	178.62 (16)	Sn—C31—C32—C33	179.9 (2)
C12—N2—C8—S3	179.16 (16)	C31—C32—C33—C34	−1.5 (5)
C9—N2—C8—S3	−2.0 (3)	C32—C33—C34—C35	1.1 (5)
Sn—S4—C8—N2	177.09 (18)	C33—C34—C35—C36	−0.4 (5)
Sn—S4—C8—S3	−2.32 (11)	C32—C31—C36—C35	−0.4 (4)
Sn—S3—C8—N2	−176.72 (15)	Sn—C31—C36—C35	−179.3 (2)
Sn—S3—C8—S4	2.72 (13)	C34—C35—C36—C31	0.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O2^i	0.97	2.52	3.404 (4)	151

Symmetry code: (i) x, y−1, z.