The molecule of the title compound, [Sn(C2H5)2(C11H12N3O2S2)Cl], features an asymmetrically chelating thiocarboxylate ligand. The Sn atom is five-coordinate within a C2ClS2 donor set that is best described as trigonal bipyramidal with S and Cl atoms in axial positions, defining a bond angle of 156.58 (2)°.
Supporting information
CCDC reference: 630188
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.024
- wR factor = 0.062
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 7.27 Ratio
There are some methyl-hydrogen which show larger displacement
factors than the averge of the hydrogen Ueq, but one (H14') shows
a bigger value, and is the one who make the high ratio.
For us this is still reasonable.
Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Sn - Cl .. 16.15 su
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.20
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 22
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.84 Ratio
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: XPREP (Bruker, 2000); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Chlorodiethyl[4-(4-nitrophenyl)piperazine-1-carbodithioato]tin(IV)
top
Crystal data top
[Sn(C2H5)2(C11H12N3O2S2)Cl] | F(000) = 992 |
Mr = 494.65 | The final unit cell was obtained from the xyz centroids of
5242 reflections after integration using the SAINTPLUS
software package (Bruker, 2000). Reduced cell calculations did not indicate any higher metric lattice symmetry
and examination of the finalatomic coordinates of the structure did not
yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988) |
Monoclinic, P21/c | Dx = 1.735 Mg m−3 |
Hall symbol: -P 2y b c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.1638 (9) Å | Cell parameters from 5242 reflections |
b = 10.5851 (7) Å | θ = 2.5–29.6° |
c = 14.0247 (9) Å | µ = 1.73 mm−1 |
β = 115.799 (1)° | T = 100 K |
V = 1893.1 (2) Å3 | Trianglar block, yellow |
Z = 4 | 0.49 × 0.42 × 0.35 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4661 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 4332 reflections with I > 2σ(I) |
Parallel mounted graphite monochromator | Rint = 0.021 |
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1 | θmax = 28.3°, θmin = 2.5° |
φ and ω scans | h = −18→16 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | k = −14→14 |
Tmin = 0.430, Tmax = 0.549 | l = −18→18 |
16982 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.024 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.062 | All H-atom parameters refined |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0298P)2 + 2.2398P] where P = (Fo2 + 2Fc2)/3 |
4661 reflections | (Δ/σ)max < 0.001 |
305 parameters | Δρmax = 1.25 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
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 | x | y | z | Uiso*/Ueq | |
Sn | 0.06969 (1) | 0.23293 (1) | 0.29408 (1) | 0.0143 (1) | |
Cl | −0.11109 (4) | 0.19507 (5) | 0.28215 (4) | 0.0170 (1) | |
S1 | 0.08452 (4) | 0.41066 (5) | 0.41456 (4) | 0.0168 (2) | |
S2 | 0.25528 (4) | 0.35152 (5) | 0.35415 (4) | 0.0168 (2) | |
O1 | 0.36114 (14) | 1.29089 (15) | 0.64523 (14) | 0.0231 (5) | |
O2 | 0.48872 (14) | 1.27462 (15) | 0.59962 (14) | 0.0224 (5) | |
N1 | 0.42322 (16) | 1.22714 (17) | 0.62536 (14) | 0.0168 (5) | |
N2 | 0.40698 (14) | 0.69539 (17) | 0.64976 (14) | 0.0135 (5) | |
N3 | 0.26164 (14) | 0.54391 (17) | 0.48052 (14) | 0.0142 (5) | |
C1 | 0.41949 (17) | 1.09049 (19) | 0.63219 (16) | 0.0146 (5) | |
C2 | 0.49031 (17) | 1.0166 (2) | 0.61263 (16) | 0.0150 (6) | |
C3 | 0.48520 (17) | 0.8863 (2) | 0.61714 (17) | 0.0149 (6) | |
C4 | 0.40907 (16) | 0.82616 (19) | 0.64143 (15) | 0.0127 (5) | |
C5 | 0.33951 (17) | 0.9046 (2) | 0.66236 (17) | 0.0162 (6) | |
C6 | 0.34489 (17) | 1.0344 (2) | 0.65790 (17) | 0.0165 (6) | |
C7 | 0.44451 (17) | 0.6135 (2) | 0.58890 (17) | 0.0152 (6) | |
C8 | 0.35810 (17) | 0.5924 (2) | 0.47702 (17) | 0.0166 (6) | |
C9 | 0.22677 (17) | 0.6194 (2) | 0.54797 (17) | 0.0154 (6) | |
C10 | 0.31822 (17) | 0.6341 (2) | 0.65770 (16) | 0.0144 (6) | |
C11 | 0.20862 (16) | 0.4468 (2) | 0.42303 (16) | 0.0144 (6) | |
C12 | 0.0106 (2) | 0.2682 (2) | 0.12730 (19) | 0.0205 (6) | |
C13 | 0.0752 (2) | 0.3504 (3) | 0.08976 (19) | 0.0250 (7) | |
C14 | 0.1402 (2) | 0.0587 (3) | 0.3675 (2) | 0.0274 (8) | |
C15 | 0.2238 (3) | 0.0120 (3) | 0.3377 (3) | 0.0360 (10) | |
H2 | 0.540 (2) | 1.056 (3) | 0.596 (2) | 0.019 (7)* | |
H3 | 0.533 (2) | 0.842 (3) | 0.608 (2) | 0.015 (6)* | |
H5 | 0.289 (2) | 0.874 (3) | 0.677 (2) | 0.027 (8)* | |
H6 | 0.302 (2) | 1.083 (3) | 0.670 (2) | 0.015 (6)* | |
H7 | 0.4639 (19) | 0.536 (2) | 0.6239 (19) | 0.011 (6)* | |
H7' | 0.508 (2) | 0.647 (3) | 0.586 (2) | 0.025 (7)* | |
H8 | 0.341 (2) | 0.669 (3) | 0.439 (2) | 0.016 (6)* | |
H8' | 0.378 (2) | 0.534 (3) | 0.438 (2) | 0.023 (7)* | |
H9 | 0.171 (2) | 0.580 (2) | 0.555 (2) | 0.015 (6)* | |
H9' | 0.208 (2) | 0.705 (3) | 0.516 (2) | 0.018 (7)* | |
H10 | 0.297 (2) | 0.681 (3) | 0.704 (2) | 0.019 (7)* | |
H10' | 0.344 (2) | 0.549 (3) | 0.689 (2) | 0.015 (6)* | |
H12 | 0.008 (2) | 0.184 (3) | 0.101 (2) | 0.027 (7)* | |
H12' | −0.061 (3) | 0.303 (3) | 0.111 (2) | 0.032 (8)* | |
H13 | 0.089 (2) | 0.436 (3) | 0.123 (2) | 0.030 (8)* | |
H13' | 0.139 (2) | 0.306 (3) | 0.099 (2) | 0.026 (7)* | |
H13" | 0.034 (2) | 0.365 (3) | 0.012 (2) | 0.028 (8)* | |
H14 | 0.157 (3) | 0.067 (4) | 0.436 (3) | 0.051 (11)* | |
H14' | 0.089 (4) | 0.002 (4) | 0.347 (4) | 0.080 (15)* | |
H15 | 0.193 (4) | 0.002 (4) | 0.263 (4) | 0.080 (15)* | |
H15' | 0.251 (3) | −0.068 (4) | 0.368 (3) | 0.058 (11)* | |
H15" | 0.273 (3) | 0.076 (4) | 0.351 (3) | 0.059 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn | 0.0125 (1) | 0.0134 (1) | 0.0166 (1) | −0.0018 (1) | 0.0060 (1) | −0.0014 (1) |
Cl | 0.0100 (2) | 0.0165 (2) | 0.0264 (3) | −0.0034 (2) | 0.0096 (2) | −0.0030 (2) |
S1 | 0.0134 (3) | 0.0156 (3) | 0.0229 (3) | −0.0031 (2) | 0.0092 (2) | −0.0043 (2) |
S2 | 0.0145 (3) | 0.0196 (3) | 0.0177 (2) | −0.0043 (2) | 0.0083 (2) | −0.0057 (2) |
O1 | 0.0277 (9) | 0.0153 (8) | 0.0267 (9) | 0.0041 (7) | 0.0121 (8) | −0.0005 (6) |
O2 | 0.0290 (10) | 0.0164 (8) | 0.0240 (8) | −0.0055 (7) | 0.0135 (7) | 0.0008 (6) |
N1 | 0.0210 (10) | 0.0122 (9) | 0.0147 (8) | −0.0010 (7) | 0.0055 (8) | −0.0002 (7) |
N2 | 0.0134 (9) | 0.0120 (8) | 0.0154 (8) | −0.0012 (6) | 0.0067 (7) | −0.0012 (6) |
N3 | 0.0123 (8) | 0.0163 (9) | 0.0147 (8) | −0.0021 (7) | 0.0065 (7) | −0.0016 (7) |
C1 | 0.0172 (10) | 0.0116 (9) | 0.0135 (9) | −0.0006 (8) | 0.0053 (8) | −0.0006 (7) |
C2 | 0.0159 (10) | 0.0166 (10) | 0.0143 (9) | −0.0025 (8) | 0.0082 (8) | −0.0011 (7) |
C3 | 0.0141 (10) | 0.0155 (10) | 0.0168 (9) | 0.0005 (8) | 0.0084 (8) | −0.0014 (8) |
C4 | 0.0125 (10) | 0.0123 (9) | 0.0114 (9) | −0.0001 (7) | 0.0035 (8) | −0.0002 (7) |
C5 | 0.0152 (10) | 0.0170 (10) | 0.0196 (10) | −0.0006 (8) | 0.0107 (9) | −0.0001 (8) |
C6 | 0.0157 (10) | 0.0170 (10) | 0.0183 (10) | 0.0021 (8) | 0.0088 (9) | −0.0011 (8) |
C7 | 0.0115 (10) | 0.0133 (10) | 0.0200 (10) | 0.0000 (8) | 0.0060 (8) | −0.0028 (8) |
C8 | 0.0153 (10) | 0.0173 (10) | 0.0189 (10) | −0.0048 (8) | 0.0091 (9) | −0.0034 (8) |
C9 | 0.0122 (10) | 0.0156 (10) | 0.0185 (10) | −0.0012 (8) | 0.0067 (8) | −0.0028 (8) |
C10 | 0.0149 (10) | 0.0140 (10) | 0.0155 (9) | −0.0030 (8) | 0.0077 (8) | −0.0009 (7) |
C11 | 0.0124 (10) | 0.0165 (10) | 0.0129 (9) | −0.0001 (8) | 0.0043 (8) | 0.0026 (7) |
C12 | 0.0196 (12) | 0.0204 (11) | 0.0194 (10) | −0.0023 (9) | 0.0065 (9) | −0.0036 (9) |
C13 | 0.0273 (13) | 0.0284 (13) | 0.0189 (11) | −0.0049 (10) | 0.0096 (10) | −0.0021 (9) |
C14 | 0.0281 (14) | 0.0227 (12) | 0.0379 (14) | 0.0073 (10) | 0.0204 (12) | 0.0082 (10) |
C15 | 0.0340 (16) | 0.0243 (14) | 0.058 (2) | 0.0075 (12) | 0.0278 (15) | −0.0017 (13) |
Geometric parameters (Å, º) top
Sn—Cl | 2.5243 (7) | C12—C13 | 1.514 (4) |
Sn—S1 | 2.4758 (6) | C14—C15 | 1.501 (5) |
Sn—S2 | 2.6959 (6) | C2—H2 | 0.93 (3) |
Sn—C12 | 2.146 (2) | C3—H3 | 0.88 (3) |
Sn—C14 | 2.136 (3) | C5—H5 | 0.89 (3) |
S1—C11 | 1.752 (3) | C6—H6 | 0.87 (3) |
S2—C11 | 1.716 (2) | C7—H7 | 0.93 (2) |
O1—N1 | 1.233 (3) | C7—H7' | 0.98 (3) |
O2—N1 | 1.239 (3) | C8—H8 | 0.94 (3) |
N1—C1 | 1.452 (3) | C8—H8' | 0.95 (3) |
N2—C4 | 1.391 (3) | C9—H9 | 0.94 (3) |
N2—C7 | 1.469 (3) | C9—H9' | 0.99 (3) |
N2—C10 | 1.461 (3) | C10—H10 | 0.96 (3) |
N3—C8 | 1.480 (3) | C10—H10' | 1.00 (3) |
N3—C9 | 1.478 (3) | C12—H12 | 0.96 (3) |
N3—C11 | 1.321 (3) | C12—H12' | 1.01 (4) |
C1—C2 | 1.390 (3) | C13—H13 | 1.00 (3) |
C1—C6 | 1.390 (4) | C13—H13' | 0.98 (3) |
C2—C3 | 1.384 (3) | C13—H13" | 1.00 (3) |
C3—C4 | 1.416 (3) | C14—H14 | 0.89 (4) |
C4—C5 | 1.414 (3) | C14—H14' | 0.89 (5) |
C5—C6 | 1.379 (3) | C15—H15 | 0.95 (5) |
C7—C8 | 1.529 (3) | C15—H15' | 0.95 (4) |
C9—C10 | 1.528 (3) | C15—H15" | 0.93 (5) |
| | | |
Sn···H14'i | 3.63 (5) | C2···H2ix | 2.87 (3) |
Sn···H13"ii | 3.47 (3) | C3···H2ix | 2.92 (3) |
Cl···S1 | 3.4430 (8) | C3···H7' | 2.61 (3) |
Cl···C12 | 3.398 (3) | C4···H9' | 2.91 (3) |
Cl···C14 | 3.532 (3) | C4···H8 | 3.06 (3) |
Cl···H12' | 3.01 (3) | C5···H10 | 2.57 (3) |
Cl···H13iii | 3.00 (3) | C5···H9' | 2.97 (3) |
Cl···H5iv | 2.91 (3) | C6···H7viii | 3.08 (3) |
Cl···H10iv | 3.02 (3) | C7···H3 | 2.68 (3) |
Cl···H13"ii | 3.04 (3) | C8···H10' | 3.10 (3) |
S1···Cl | 3.4430 (8) | C10···H5 | 2.61 (3) |
S1···S2 | 2.9569 (9) | C12···H9'iii | 2.94 (3) |
S2···C12 | 3.649 (3) | C12···H14'i | 2.95 (5) |
S2···C13 | 3.467 (3) | C13···H14xiii | 2.99 (4) |
S2···S1 | 2.9569 (9) | C13···H6v | 2.99 (3) |
S2···C15 | 3.616 (3) | C14···H12'iii | 3.00 (3) |
S2···C14 | 3.545 (3) | H2···O2 | 2.43 (3) |
S2···C6v | 3.699 (2) | H2···C2ix | 2.87 (3) |
S1···H12i | 3.14 (3) | H2···C3ix | 2.92 (3) |
S1···H9 | 2.55 (2) | H3···C7 | 2.68 (3) |
S2···H8' | 2.52 (3) | H3···H7' | 2.09 (4) |
S2···H15" | 2.93 (4) | H5···C10 | 2.61 (3) |
S2···H7'vi | 3.08 (3) | H5···H10 | 2.07 (4) |
S2···H13 | 3.20 (3) | H5···Cliv | 2.91 (3) |
S2···H6v | 3.01 (3) | H6···O1 | 2.43 (3) |
O1···C11vii | 3.353 (3) | H6···S2xi | 3.01 (3) |
O1···C4viii | 3.348 (3) | H6···C13xi | 2.99 (3) |
O1···C3viii | 3.248 (3) | H6···H13'xi | 2.39 (4) |
O2···C8ix | 3.142 (3) | H7···O2xii | 2.83 (2) |
O2···C7ix | 3.386 (3) | H7···H10' | 2.26 (4) |
O2···C4viii | 3.318 (3) | H7···C6x | 3.08 (3) |
O1···H6 | 2.43 (3) | H7'···C3 | 2.61 (3) |
O1···H10'vii | 2.83 (3) | H7'···H3 | 2.09 (4) |
O2···H2 | 2.43 (3) | H7'···S2vi | 3.08 (3) |
O2···H7vii | 2.83 (2) | H7'···O2ix | 2.75 (3) |
O2···H7'ix | 2.75 (3) | H8···C4 | 3.06 (3) |
O2···H8ix | 2.76 (3) | H8···H9' | 2.58 (4) |
N1···N2viii | 3.040 (3) | H8···O2ix | 2.76 (3) |
N1···C4viii | 3.267 (3) | H8'···S2 | 2.52 (3) |
N2···N3 | 2.862 (3) | H9···S1 | 2.55 (2) |
N2···N1x | 3.040 (3) | H9'···C4 | 2.91 (3) |
N2···C1x | 3.175 (3) | H9'···C5 | 2.97 (3) |
N3···N2 | 2.862 (3) | H9'···H8 | 2.58 (4) |
C1···N2viii | 3.175 (3) | H9'···C12i | 2.94 (3) |
C1···C7viii | 3.537 (3) | H9'···H12'i | 2.31 (4) |
C2···C10viii | 3.417 (3) | H10···C5 | 2.57 (3) |
C2···C2ix | 3.307 (3) | H10···H5 | 2.07 (4) |
C2···C3ix | 3.540 (3) | H10···Cliv | 3.02 (3) |
C3···C2ix | 3.540 (3) | H10'···O1xii | 2.83 (3) |
C3···O1x | 3.248 (3) | H10'···C8 | 3.10 (3) |
C4···O1x | 3.348 (3) | H10'···H7 | 2.26 (4) |
C4···O2x | 3.318 (3) | H10'···C2x | 2.77 (3) |
C4···N1x | 3.267 (3) | H12···S1iii | 3.14 (3) |
C5···C9 | 3.465 (3) | H12'···C14i | 3.00 (3) |
C6···S2xi | 3.699 (2) | H12'···H9'iii | 2.31 (4) |
C7···C1x | 3.537 (3) | H12'···H14'i | 2.27 (6) |
C7···O2ix | 3.386 (3) | H13···S2 | 3.20 (3) |
C8···O2ix | 3.142 (3) | H13···Cli | 3.00 (3) |
C9···C12i | 3.554 (4) | H13'···H6v | 2.39 (4) |
C9···C5 | 3.465 (3) | H13"···Snxiii | 3.47 (3) |
C10···C2x | 3.417 (3) | H13"···Clxiii | 3.04 (3) |
C11···O1xii | 3.353 (3) | H13"···H14xiii | 2.51 (5) |
C12···C9iii | 3.554 (4) | H14···C13ii | 2.99 (4) |
C12···S2 | 3.649 (3) | H14···H13"ii | 2.51 (5) |
C12···Cl | 3.398 (3) | H14'···Sniii | 3.63 (5) |
C14···S2 | 3.545 (3) | H14'···C12iii | 2.95 (5) |
C14···Cl | 3.532 (3) | H14'···H12'iii | 2.27 (6) |
C2···H10'viii | 2.77 (3) | H15"···S2 | 2.93 (4) |
| | | |
Cl—Sn—S1 | 87.03 (2) | C6—C5—H5 | 116 (2) |
Cl—Sn—S2 | 156.58 (2) | C1—C6—H6 | 118 (2) |
Cl—Sn—C12 | 92.99 (8) | C5—C6—H6 | 122 (2) |
Cl—Sn—C14 | 98.21 (8) | N2—C7—H7 | 108.1 (16) |
S1—Sn—S2 | 69.59 (2) | N2—C7—H7' | 112.3 (17) |
S1—Sn—C12 | 119.25 (6) | C8—C7—H7 | 109.4 (15) |
S1—Sn—C14 | 116.36 (7) | C8—C7—H7' | 110.4 (15) |
S2—Sn—C12 | 97.14 (8) | H7—C7—H7' | 106 (3) |
S2—Sn—C14 | 93.65 (8) | N3—C8—H8 | 107.7 (19) |
C12—Sn—C14 | 123.66 (9) | N3—C8—H8' | 107.7 (19) |
Sn—S1—C11 | 89.82 (7) | C7—C8—H8 | 110.4 (17) |
Sn—S2—C11 | 83.54 (8) | C7—C8—H8' | 112.5 (17) |
O1—N1—O2 | 122.82 (19) | H8—C8—H8' | 108 (2) |
O1—N1—C1 | 118.7 (2) | N3—C9—H9 | 111.1 (15) |
O2—N1—C1 | 118.5 (2) | N3—C9—H9' | 107.6 (16) |
C4—N2—C7 | 120.82 (19) | C10—C9—H9 | 108.9 (16) |
C4—N2—C10 | 119.9 (2) | C10—C9—H9' | 107.7 (16) |
C7—N2—C10 | 108.86 (17) | H9—C9—H9' | 112 (2) |
C8—N3—C9 | 113.84 (17) | N2—C10—H10 | 110.7 (19) |
C8—N3—C11 | 122.52 (19) | N2—C10—H10' | 105.8 (18) |
C9—N3—C11 | 123.5 (2) | C9—C10—H10 | 110.8 (17) |
N1—C1—C2 | 119.8 (2) | C9—C10—H10' | 109.8 (16) |
N1—C1—C6 | 119.8 (2) | H10—C10—H10' | 109 (2) |
C2—C1—C6 | 120.42 (19) | Sn—C12—H12 | 100.9 (16) |
C1—C2—C3 | 119.7 (2) | Sn—C12—H12' | 100.8 (16) |
C2—C3—C4 | 121.3 (2) | C13—C12—H12 | 109.2 (18) |
N2—C4—C3 | 120.9 (2) | C13—C12—H12' | 114.3 (19) |
N2—C4—C5 | 121.7 (2) | H12—C12—H12' | 113 (3) |
C3—C4—C5 | 117.30 (19) | C12—C13—H13 | 112.6 (17) |
C4—C5—C6 | 121.2 (2) | C12—C13—H13' | 110.0 (18) |
C1—C6—C5 | 120.1 (2) | C12—C13—H13" | 108.3 (18) |
N2—C7—C8 | 110.6 (2) | H13—C13—H13' | 113 (3) |
N3—C8—C7 | 110.78 (18) | H13—C13—H13" | 106 (2) |
N3—C9—C10 | 109.1 (2) | H13'—C13—H13" | 107 (2) |
N2—C10—C9 | 110.41 (18) | Sn—C14—H14 | 107 (3) |
S1—C11—S2 | 117.04 (12) | Sn—C14—H14' | 106 (3) |
S1—C11—N3 | 119.91 (18) | C15—C14—H14 | 118 (3) |
S2—C11—N3 | 123.05 (19) | C15—C14—H14' | 109 (4) |
Sn—C12—C13 | 118.10 (17) | H14—C14—H14' | 102 (4) |
Sn—C14—C15 | 114.2 (2) | C14—C15—H15 | 108 (4) |
C1—C2—H2 | 119.1 (19) | C14—C15—H15' | 113 (3) |
C3—C2—H2 | 121.2 (19) | C14—C15—H15" | 109 (3) |
C2—C3—H3 | 118 (2) | H15—C15—H15' | 107 (4) |
C4—C3—H3 | 121 (2) | H15—C15—H15" | 104 (4) |
C4—C5—H5 | 123 (2) | H15'—C15—H15" | 116 (4) |
| | | |
Cl—Sn—S1—C11 | −177.91 (7) | C10—N2—C4—C3 | −170.05 (18) |
S2—Sn—S1—C11 | 0.63 (7) | C10—N2—C4—C5 | 13.5 (3) |
C12—Sn—S1—C11 | −86.14 (12) | C4—N2—C7—C8 | −84.0 (2) |
C14—Sn—S1—C11 | 84.39 (12) | C10—N2—C7—C8 | 60.9 (2) |
Cl—Sn—S2—C11 | 3.03 (9) | C4—N2—C10—C9 | 81.7 (2) |
S1—Sn—S2—C11 | −0.64 (7) | C7—N2—C10—C9 | −63.5 (2) |
C12—Sn—S2—C11 | 117.96 (10) | C9—N3—C8—C7 | 51.0 (2) |
C14—Sn—S2—C11 | −117.45 (10) | C11—N3—C8—C7 | −133.0 (2) |
Cl—Sn—C12—C13 | 154.18 (19) | C8—N3—C9—C10 | −52.7 (2) |
S1—Sn—C12—C13 | 65.9 (2) | C11—N3—C9—C10 | 131.4 (2) |
S2—Sn—C12—C13 | −4.7 (2) | C8—N3—C11—S1 | −169.60 (15) |
C14—Sn—C12—C13 | −103.9 (2) | C8—N3—C11—S2 | 10.3 (3) |
Cl—Sn—C14—C15 | 148.7 (2) | C9—N3—C11—S1 | 6.0 (3) |
S1—Sn—C14—C15 | −120.6 (2) | C9—N3—C11—S2 | −174.15 (16) |
S2—Sn—C14—C15 | −51.6 (2) | N1—C1—C2—C3 | −178.72 (19) |
C12—Sn—C14—C15 | 49.5 (3) | C6—C1—C2—C3 | 1.1 (3) |
Sn—S1—C11—S2 | −1.04 (11) | N1—C1—C6—C5 | 178.65 (19) |
Sn—S1—C11—N3 | 178.87 (17) | C2—C1—C6—C5 | −1.1 (3) |
Sn—S2—C11—S1 | 0.96 (11) | C1—C2—C3—C4 | 0.0 (3) |
Sn—S2—C11—N3 | −178.95 (18) | C2—C3—C4—N2 | −177.54 (19) |
O1—N1—C1—C2 | −178.47 (19) | C2—C3—C4—C5 | −0.9 (3) |
O1—N1—C1—C6 | 1.7 (3) | N2—C4—C5—C6 | 177.4 (2) |
O2—N1—C1—C2 | 1.6 (3) | C3—C4—C5—C6 | 0.8 (3) |
O2—N1—C1—C6 | −178.2 (2) | C4—C5—C6—C1 | 0.2 (3) |
C7—N2—C4—C3 | −29.0 (3) | N2—C7—C8—N3 | −54.2 (2) |
C7—N2—C4—C5 | 154.5 (2) | N3—C9—C10—N2 | 58.6 (2) |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x, −y+1, −z+1; (v) x, −y+3/2, z−1/2; (vi) −x+1, −y+1, −z+1; (vii) x, y+1, z; (viii) −x+1, y+1/2, −z+3/2; (ix) −x+1, −y+2, −z+1; (x) −x+1, y−1/2, −z+3/2; (xi) x, −y+3/2, z+1/2; (xii) x, y−1, z; (xiii) x, −y+1/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.87 (3) | 2.43 (3) | 2.737 (3) | 101 (2) |
C8—H8′···S2 | 0.95 (3) | 2.52 (3) | 3.067 (2) | 117 (2) |
C9—H9···S1 | 0.94 (3) | 2.55 (2) | 3.027 (2) | 112.1 (19) |