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In the title complex, [Sn(C6H5)2(C10H16NS2)Cl], the Sn atom has a distorted trigonal–bipyramidal geometry, with an axial S—Sn—Cl bond angle of 156.87 (3)°. Intra­molecular hydrogen bonding is present between an S atom and the H atom of the amine group. The mol­ecules are linked by an inter­molecular C—H...Cl hydrogen bond to form chains extending in the c direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052123/ng2173sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052123/ng2173Isup2.hkl
Contains datablock I

CCDC reference: 633970

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.027
  • wR factor = 0.089
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.92
Author Response: ...Using the Stoe IPDS Mark1 machine with a triclinic crystal
 a small fraction of the Ewald sphere is inaccessible.

 However, this does not appear to have a significant effect if one compares

 the bond distances and angles in the complex with those observed in

 similar complexes in the litterature.



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.607 0.812 Tmin(prime) and Tmax expected: 0.489 0.573 RR(prime) = 0.874 Please check that your absorption correction is appropriate. CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 22.51 Cell volume su given = 19.00 PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.70 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 1100 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for C19 - C22 .. 6.48 su
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.705 Tmax scaled 0.573 Tmin scaled 0.428
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: ... This work is done by the collaboration of two groups.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

[2-(Butylamino)cyclopent-1-ene-1-carbodithioato)chlorodiphenyltin(IV) top
Crystal data top
[Sn(C6H5)2(C10H16NS2)Cl]Z = 2
Mr = 522.70F(000) = 528
Triclinic, P1Dx = 1.487 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4881 (9) ÅCell parameters from 7998 reflections
b = 11.0779 (10) Åθ = 2.2–25.9°
c = 12.1896 (12) ŵ = 1.39 mm1
α = 106.457 (11)°T = 173 K
β = 104.555 (11)°Block, yellow
γ = 96.053 (11)°0.50 × 0.40 × 0.40 mm
V = 1167.57 (19) Å3
Data collection top
Stoe IPDS
diffractometer
4133 independent reflections
Radiation source: fine-focus sealed tube3825 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 0.81Å pixels mm-1θmax = 25.9°, θmin = 2.5°
φ scansh = 1110
Absorption correction: multi-scan
(MULABS in PLATON; Spek, 2003)
k = 1313
Tmin = 0.607, Tmax = 0.812l = 1414
8018 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0353P)2 + 2.4792P]
where P = (Fo2 + 2Fc2)/3
4133 reflections(Δ/σ)max = 0.001
240 parametersΔρmax = 0.98 e Å3
0 restraintsΔρmin = 1.17 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
xyzUiso*/Ueq
C10.1014 (4)0.7518 (4)0.6905 (3)0.0296 (6)
C20.1691 (4)0.6598 (4)0.5802 (4)0.0369 (9)
H2A0.11070.60930.54030.044*
C30.3212 (5)0.6396 (5)0.5266 (5)0.0535 (12)
H3A0.36610.57550.45110.064*
C40.4061 (5)0.7130 (6)0.5834 (5)0.0621 (15)
H4A0.51010.69900.54740.074*
C50.3407 (6)0.8066 (6)0.6924 (5)0.0629 (16)
H5A0.40000.85720.73100.075*
C60.1882 (5)0.8278 (5)0.7468 (4)0.0448 (11)
H6A0.14360.89340.82150.054*
C70.2741 (4)0.9572 (4)0.8403 (3)0.0296 (6)
C80.2875 (6)1.0486 (5)0.9486 (4)0.0570 (13)
H8A0.23341.02930.99930.068*
C90.3783 (7)1.1676 (5)0.9844 (5)0.0642 (15)
H9A0.38601.22911.05910.077*
C100.4570 (5)1.1967 (5)0.9126 (5)0.0510 (12)
H10A0.51921.27840.93700.061*
C110.4456 (5)1.1073 (5)0.8050 (5)0.0543 (12)
H11A0.50011.12720.75480.065*
C120.3546 (5)0.9878 (5)0.7692 (4)0.0424 (10)
H12A0.34800.92640.69480.051*
C130.1570 (4)0.6669 (4)0.9878 (3)0.0288 (8)
C140.1887 (4)0.6103 (4)1.0764 (3)0.0288 (8)
C150.1612 (4)0.6504 (4)1.1891 (3)0.0358 (9)
C160.2188 (5)0.5675 (5)1.2626 (4)0.0453 (11)
H16B0.13660.50521.26350.054*
H16A0.27390.62031.34590.054*
C170.3212 (6)0.4992 (6)1.1991 (4)0.0568 (13)
H17B0.31880.41171.20510.068*
H17A0.42460.54751.23450.068*
C180.2615 (5)0.4935 (4)1.0684 (4)0.0390 (9)
H18B0.34300.49861.03170.047*
H18A0.18840.41351.02090.047*
C190.0545 (7)0.7843 (5)1.3418 (4)0.0581 (14)
H19A0.08660.72461.38720.070*
C200.1367 (7)0.9137 (6)1.4133 (5)0.0670 (16)
H20B0.11470.93781.49110.080*
H20A0.10090.97431.37150.080*
C210.3002 (7)0.9282 (7)1.4364 (5)0.0712 (16)
H21A0.32390.91271.36040.107*
H21B0.33640.86621.47480.107*
H21C0.34811.01531.48910.107*
C220.1182 (6)0.7713 (6)1.3140 (5)0.0609 (14)
H22C0.14360.79891.38920.091*
H22B0.16600.68171.27000.091*
H22A0.15280.82521.26540.091*
N10.0919 (5)0.7438 (4)1.2269 (3)0.0492 (10)
H10.06430.78771.17800.059*
S10.07650 (11)0.80017 (10)0.99417 (8)0.0340 (2)
S20.20321 (10)0.60052 (10)0.85539 (8)0.0314 (2)
Cl10.20539 (11)0.67447 (10)0.60336 (8)0.0372 (2)
Sn10.12866 (2)0.77481 (2)0.780576 (19)0.02534 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0317 (13)0.0330 (17)0.0281 (12)0.0090 (10)0.0101 (10)0.0137 (11)
C20.037 (2)0.037 (3)0.037 (2)0.0078 (16)0.0072 (16)0.0140 (17)
C30.038 (2)0.064 (4)0.052 (3)0.002 (2)0.000 (2)0.022 (2)
C40.031 (2)0.095 (5)0.075 (4)0.014 (2)0.010 (2)0.053 (3)
C50.048 (3)0.101 (5)0.071 (3)0.045 (3)0.032 (3)0.052 (3)
C60.050 (2)0.056 (3)0.039 (2)0.028 (2)0.0208 (19)0.021 (2)
C70.0317 (13)0.0330 (17)0.0281 (12)0.0090 (10)0.0101 (10)0.0137 (11)
C80.088 (4)0.044 (3)0.037 (2)0.006 (2)0.031 (2)0.005 (2)
C90.094 (4)0.041 (3)0.042 (3)0.008 (3)0.019 (3)0.001 (2)
C100.040 (2)0.037 (3)0.064 (3)0.0038 (18)0.002 (2)0.014 (2)
C110.043 (2)0.052 (3)0.072 (3)0.000 (2)0.031 (2)0.017 (3)
C120.040 (2)0.044 (3)0.044 (2)0.0045 (18)0.0217 (18)0.0093 (19)
C130.0279 (17)0.033 (2)0.0237 (16)0.0014 (14)0.0059 (13)0.0089 (15)
C140.0341 (18)0.024 (2)0.0278 (17)0.0035 (14)0.0067 (14)0.0111 (15)
C150.044 (2)0.038 (3)0.0284 (18)0.0067 (17)0.0086 (16)0.0175 (17)
C160.062 (3)0.047 (3)0.036 (2)0.014 (2)0.0121 (19)0.027 (2)
C170.070 (3)0.067 (4)0.047 (3)0.034 (3)0.015 (2)0.034 (3)
C180.046 (2)0.035 (3)0.040 (2)0.0121 (17)0.0111 (17)0.0189 (18)
C190.100 (4)0.056 (4)0.040 (2)0.032 (3)0.037 (3)0.026 (2)
C200.102 (5)0.061 (4)0.050 (3)0.030 (3)0.036 (3)0.019 (3)
C210.075 (4)0.081 (5)0.051 (3)0.001 (3)0.020 (3)0.015 (3)
C220.071 (3)0.072 (4)0.058 (3)0.033 (3)0.035 (3)0.028 (3)
N10.087 (3)0.050 (3)0.0316 (18)0.033 (2)0.0301 (19)0.0265 (17)
S10.0511 (6)0.0366 (6)0.0260 (4)0.0197 (4)0.0197 (4)0.0165 (4)
S20.0397 (5)0.0307 (6)0.0246 (4)0.0109 (4)0.0103 (4)0.0081 (4)
Cl10.0433 (5)0.0439 (6)0.0251 (4)0.0102 (4)0.0174 (4)0.0052 (4)
Sn10.02990 (14)0.02902 (18)0.01925 (13)0.00717 (9)0.00978 (9)0.00827 (10)
Geometric parameters (Å, º) top
C1—C21.382 (6)C14—C181.521 (6)
C1—C61.401 (6)C15—N11.318 (6)
C1—Sn12.134 (4)C15—C161.507 (5)
C2—C31.391 (6)C16—C171.523 (7)
C2—H2A0.9500C16—H16B0.9900
C3—C41.374 (8)C16—H16A0.9900
C3—H3A0.9500C17—C181.531 (6)
C4—C51.376 (9)C17—H17B0.9900
C4—H4A0.9500C17—H17A0.9900
C5—C61.395 (7)C18—H18B0.9900
C5—H5A0.9500C18—H18A0.9900
C6—H6A0.9500C19—C201.462 (8)
C7—C121.376 (5)C19—N11.489 (5)
C7—C81.384 (6)C19—C221.569 (8)
C7—Sn12.143 (4)C19—H19A1.0000
C8—C91.385 (7)C20—C211.489 (8)
C8—H8A0.9500C20—H20B0.9900
C9—C101.366 (7)C20—H20A0.9900
C9—H9A0.9500C21—H21A0.9800
C10—C111.372 (7)C21—H21B0.9800
C10—H10A0.9500C21—H21C0.9800
C11—C121.389 (7)C22—H22C0.9800
C11—H11A0.9500C22—H22B0.9800
C12—H12A0.9500C22—H22A0.9800
C13—C141.383 (5)N1—H10.8800
C13—S11.724 (4)S1—Sn12.7139 (9)
C13—S21.757 (4)S2—Sn12.4538 (10)
C14—C151.418 (5)Cl1—Sn12.4562 (9)
C2—C1—C6118.8 (4)C16—C17—C18105.3 (4)
C2—C1—Sn1121.9 (3)C16—C17—H17B110.7
C6—C1—Sn1119.3 (3)C18—C17—H17B110.7
C1—C2—C3121.2 (4)C16—C17—H17A110.7
C1—C2—H2A119.4C18—C17—H17A110.7
C3—C2—H2A119.4H17B—C17—H17A108.8
C4—C3—C2119.7 (5)C14—C18—C17103.7 (4)
C4—C3—H3A120.2C14—C18—H18B111.0
C2—C3—H3A120.2C17—C18—H18B111.0
C3—C4—C5120.1 (4)C14—C18—H18A111.0
C3—C4—H4A119.9C17—C18—H18A111.0
C5—C4—H4A119.9H18B—C18—H18A109.0
C4—C5—C6120.7 (5)C20—C19—N1109.5 (4)
C4—C5—H5A119.7C20—C19—C22113.7 (5)
C6—C5—H5A119.7N1—C19—C22109.0 (4)
C5—C6—C1119.5 (5)C20—C19—H19A108.2
C5—C6—H6A120.2N1—C19—H19A108.2
C1—C6—H6A120.2C22—C19—H19A108.2
C12—C7—C8118.0 (4)C19—C20—C21114.1 (5)
C12—C7—Sn1120.2 (3)C19—C20—H20B108.7
C8—C7—Sn1121.8 (3)C21—C20—H20B108.7
C7—C8—C9121.2 (4)C19—C20—H20A108.7
C7—C8—H8A119.4C21—C20—H20A108.7
C9—C8—H8A119.4H20B—C20—H20A107.6
C10—C9—C8120.1 (5)C20—C21—H21A109.5
C10—C9—H9A119.9C20—C21—H21B109.5
C8—C9—H9A119.9H21A—C21—H21B109.5
C9—C10—C11119.6 (5)C20—C21—H21C109.5
C9—C10—H10A120.2H21A—C21—H21C109.5
C11—C10—H10A120.2H21B—C21—H21C109.5
C10—C11—C12120.3 (4)C19—C22—H22C109.5
C10—C11—H11A119.9C19—C22—H22B109.5
C12—C11—H11A119.9H22C—C22—H22B109.5
C7—C12—C11120.8 (4)C19—C22—H22A109.5
C7—C12—H12A119.6H22C—C22—H22A109.5
C11—C12—H12A119.6H22B—C22—H22A109.5
C14—C13—S1126.1 (3)C15—N1—C19128.3 (4)
C14—C13—S2118.5 (3)C15—N1—H1115.9
S1—C13—S2115.5 (2)C19—N1—H1115.9
C13—C14—C15126.7 (4)C13—S1—Sn183.73 (12)
C13—C14—C18124.7 (3)C13—S2—Sn191.38 (13)
C15—C14—C18108.5 (3)C1—Sn1—C7121.10 (14)
N1—C15—C14126.8 (3)C1—Sn1—S2116.28 (11)
N1—C15—C16122.9 (4)C7—Sn1—S2120.92 (10)
C14—C15—C16110.3 (4)C1—Sn1—Cl197.18 (10)
C15—C16—C17103.9 (3)C7—Sn1—Cl197.93 (10)
C15—C16—H16B111.0S2—Sn1—Cl187.67 (3)
C17—C16—H16B111.0C1—Sn1—S192.31 (10)
C15—C16—H16A111.0C7—Sn1—S195.10 (10)
C17—C16—H16A111.0S2—Sn1—S169.22 (3)
H16B—C16—H16A109.0Cl1—Sn1—S1156.87 (3)
C6—C1—C2—C31.7 (6)C14—C15—N1—C19176.7 (5)
Sn1—C1—C2—C3175.2 (3)C16—C15—N1—C191.3 (8)
C1—C2—C3—C40.5 (7)C20—C19—N1—C15114.8 (6)
C2—C3—C4—C50.5 (8)C22—C19—N1—C15120.3 (5)
C3—C4—C5—C60.3 (8)C14—C13—S1—Sn1175.1 (3)
C4—C5—C6—C10.9 (8)S2—C13—S1—Sn14.19 (18)
C2—C1—C6—C51.9 (6)C14—C13—S2—Sn1174.8 (3)
Sn1—C1—C6—C5175.2 (4)S1—C13—S2—Sn14.61 (19)
C12—C7—C8—C90.4 (8)C2—C1—Sn1—C7126.1 (3)
Sn1—C7—C8—C9178.0 (4)C6—C1—Sn1—C757.0 (4)
C7—C8—C9—C100.1 (9)C2—C1—Sn1—S268.6 (3)
C8—C9—C10—C110.1 (9)C6—C1—Sn1—S2108.3 (3)
C9—C10—C11—C120.0 (8)C2—C1—Sn1—Cl122.3 (3)
C8—C7—C12—C110.6 (7)C6—C1—Sn1—Cl1160.8 (3)
Sn1—C7—C12—C11177.9 (4)C2—C1—Sn1—S1136.5 (3)
C10—C11—C12—C70.4 (8)C6—C1—Sn1—S140.4 (3)
S1—C13—C14—C150.1 (6)C12—C7—Sn1—C194.3 (3)
S2—C13—C14—C15179.4 (3)C8—C7—Sn1—C184.1 (4)
S1—C13—C14—C18179.3 (3)C12—C7—Sn1—S2101.1 (3)
S2—C13—C14—C180.1 (5)C8—C7—Sn1—S280.5 (4)
C13—C14—C15—N14.7 (7)C12—C7—Sn1—Cl19.1 (3)
C18—C14—C15—N1175.9 (4)C8—C7—Sn1—Cl1172.6 (4)
C13—C14—C15—C16177.1 (4)C12—C7—Sn1—S1169.9 (3)
C18—C14—C15—C162.3 (5)C8—C7—Sn1—S111.7 (4)
N1—C15—C16—C17166.2 (5)C13—S2—Sn1—C184.82 (16)
C14—C15—C16—C1715.5 (5)C13—S2—Sn1—C780.48 (16)
C15—C16—C17—C1826.9 (5)C13—S2—Sn1—Cl1178.32 (12)
C13—C14—C18—C17160.4 (4)C13—S2—Sn1—S12.83 (12)
C15—C14—C18—C1719.0 (5)C13—S1—Sn1—C1120.20 (16)
C16—C17—C18—C1428.2 (5)C13—S1—Sn1—C7118.30 (15)
N1—C19—C20—C2155.6 (6)C13—S1—Sn1—S22.90 (12)
C22—C19—C20—C21177.8 (4)C13—S1—Sn1—Cl15.83 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S10.882.313.045 (3)141
C19—H19A···Cl1i1.002.833.737 (5)152
Symmetry code: (i) x, y, z+1.
 

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