[2-(Butyl­amino)cyclo­pent-1-ene-1-carbodithio­ato]chloro­diphenyl­tin(IV)

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.

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

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)

Crystal data

[Sn(C6H5)2(C10H16NS2)Cl]	Z = 2
Mr = 522.70	F(000) = 528
Triclinic, P1	Dx = 1.487 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4881 (9) Å	Cell parameters from 7998 reflections
b = 11.0779 (10) Å	θ = 2.2–25.9°
c = 12.1896 (12) Å	µ = 1.39 mm^−1
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) Å^3

Data collection

Stoe IPDS diffractometer	4133 independent reflections
Radiation source: fine-focus sealed tube	3825 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 0.81Å pixels mm^-1	θmax = 25.9°, θmin = 2.5°
φ scans	h = −11→10
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2003)	k = −13→13
Tmin = 0.607, Tmax = 0.812	l = −14→14
8018 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0353P)^2 + 2.4792P] where P = (Fo^2 + 2Fc^2)/3
4133 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.98 e Å^−3
0 restraints	Δρmin = −1.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.1014 (4)	0.7518 (4)	0.6905 (3)	0.0296 (6)
C2	−0.1691 (4)	0.6598 (4)	0.5802 (4)	0.0369 (9)
H2A	−0.1107	0.6093	0.5403	0.044*
C3	−0.3212 (5)	0.6396 (5)	0.5266 (5)	0.0535 (12)
H3A	−0.3661	0.5755	0.4511	0.064*
C4	−0.4061 (5)	0.7130 (6)	0.5834 (5)	0.0621 (15)
H4A	−0.5101	0.6990	0.5474	0.074*
C5	−0.3407 (6)	0.8066 (6)	0.6924 (5)	0.0629 (16)
H5A	−0.4000	0.8572	0.7310	0.075*
C6	−0.1882 (5)	0.8278 (5)	0.7468 (4)	0.0448 (11)
H6A	−0.1436	0.8934	0.8215	0.054*
C7	0.2741 (4)	0.9572 (4)	0.8403 (3)	0.0296 (6)
C8	0.2875 (6)	1.0486 (5)	0.9486 (4)	0.0570 (13)
H8A	0.2334	1.0293	0.9993	0.068*
C9	0.3783 (7)	1.1676 (5)	0.9844 (5)	0.0642 (15)
H9A	0.3860	1.2291	1.0591	0.077*
C10	0.4570 (5)	1.1967 (5)	0.9126 (5)	0.0510 (12)
H10A	0.5192	1.2784	0.9370	0.061*
C11	0.4456 (5)	1.1073 (5)	0.8050 (5)	0.0543 (12)
H11A	0.5001	1.1272	0.7548	0.065*
C12	0.3546 (5)	0.9878 (5)	0.7692 (4)	0.0424 (10)
H12A	0.3480	0.9264	0.6948	0.051*
C13	0.1570 (4)	0.6669 (4)	0.9878 (3)	0.0288 (8)
C14	0.1887 (4)	0.6103 (4)	1.0764 (3)	0.0288 (8)
C15	0.1612 (4)	0.6504 (4)	1.1891 (3)	0.0358 (9)
C16	0.2188 (5)	0.5675 (5)	1.2626 (4)	0.0453 (11)
H16B	0.1366	0.5052	1.2635	0.054*
H16A	0.2739	0.6203	1.3459	0.054*
C17	0.3212 (6)	0.4992 (6)	1.1991 (4)	0.0568 (13)
H17B	0.3188	0.4117	1.2051	0.068*
H17A	0.4246	0.5475	1.2345	0.068*
C18	0.2615 (5)	0.4935 (4)	1.0684 (4)	0.0390 (9)
H18B	0.3430	0.4986	1.0317	0.047*
H18A	0.1884	0.4135	1.0209	0.047*
C19	0.0545 (7)	0.7843 (5)	1.3418 (4)	0.0581 (14)
H19A	0.0866	0.7246	1.3872	0.070*
C20	0.1367 (7)	0.9137 (6)	1.4133 (5)	0.0670 (16)
H20B	0.1147	0.9378	1.4911	0.080*
H20A	0.1009	0.9743	1.3715	0.080*
C21	0.3002 (7)	0.9282 (7)	1.4364 (5)	0.0712 (16)
H21A	0.3239	0.9127	1.3604	0.107*
H21B	0.3364	0.8662	1.4748	0.107*
H21C	0.3481	1.0153	1.4891	0.107*
C22	−0.1182 (6)	0.7713 (6)	1.3140 (5)	0.0609 (14)
H22C	−0.1436	0.7989	1.3892	0.091*
H22B	−0.1660	0.6817	1.2700	0.091*
H22A	−0.1528	0.8252	1.2654	0.091*
N1	0.0919 (5)	0.7438 (4)	1.2269 (3)	0.0492 (10)
H1	0.0643	0.7877	1.1780	0.059*
S1	0.07650 (11)	0.80017 (10)	0.99417 (8)	0.0340 (2)
S2	0.20321 (10)	0.60052 (10)	0.85539 (8)	0.0314 (2)
Cl1	0.20539 (11)	0.67447 (10)	0.60336 (8)	0.0372 (2)
Sn1	0.12866 (2)	0.77481 (2)	0.780576 (19)	0.02534 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0317 (13)	0.0330 (17)	0.0281 (12)	0.0090 (10)	0.0101 (10)	0.0137 (11)
C2	0.037 (2)	0.037 (3)	0.037 (2)	0.0078 (16)	0.0072 (16)	0.0140 (17)
C3	0.038 (2)	0.064 (4)	0.052 (3)	0.002 (2)	0.000 (2)	0.022 (2)
C4	0.031 (2)	0.095 (5)	0.075 (4)	0.014 (2)	0.010 (2)	0.053 (3)
C5	0.048 (3)	0.101 (5)	0.071 (3)	0.045 (3)	0.032 (3)	0.052 (3)
C6	0.050 (2)	0.056 (3)	0.039 (2)	0.028 (2)	0.0208 (19)	0.021 (2)
C7	0.0317 (13)	0.0330 (17)	0.0281 (12)	0.0090 (10)	0.0101 (10)	0.0137 (11)
C8	0.088 (4)	0.044 (3)	0.037 (2)	−0.006 (2)	0.031 (2)	0.005 (2)
C9	0.094 (4)	0.041 (3)	0.042 (3)	−0.008 (3)	0.019 (3)	−0.001 (2)
C10	0.040 (2)	0.037 (3)	0.064 (3)	−0.0038 (18)	0.002 (2)	0.014 (2)
C11	0.043 (2)	0.052 (3)	0.072 (3)	0.000 (2)	0.031 (2)	0.017 (3)
C12	0.040 (2)	0.044 (3)	0.044 (2)	0.0045 (18)	0.0217 (18)	0.0093 (19)
C13	0.0279 (17)	0.033 (2)	0.0237 (16)	0.0014 (14)	0.0059 (13)	0.0089 (15)
C14	0.0341 (18)	0.024 (2)	0.0278 (17)	0.0035 (14)	0.0067 (14)	0.0111 (15)
C15	0.044 (2)	0.038 (3)	0.0284 (18)	0.0067 (17)	0.0086 (16)	0.0175 (17)
C16	0.062 (3)	0.047 (3)	0.036 (2)	0.014 (2)	0.0121 (19)	0.027 (2)
C17	0.070 (3)	0.067 (4)	0.047 (3)	0.034 (3)	0.015 (2)	0.034 (3)
C18	0.046 (2)	0.035 (3)	0.040 (2)	0.0121 (17)	0.0111 (17)	0.0189 (18)
C19	0.100 (4)	0.056 (4)	0.040 (2)	0.032 (3)	0.037 (3)	0.026 (2)
C20	0.102 (5)	0.061 (4)	0.050 (3)	0.030 (3)	0.036 (3)	0.019 (3)
C21	0.075 (4)	0.081 (5)	0.051 (3)	−0.001 (3)	0.020 (3)	0.015 (3)
C22	0.071 (3)	0.072 (4)	0.058 (3)	0.033 (3)	0.035 (3)	0.028 (3)
N1	0.087 (3)	0.050 (3)	0.0316 (18)	0.033 (2)	0.0301 (19)	0.0265 (17)
S1	0.0511 (6)	0.0366 (6)	0.0260 (4)	0.0197 (4)	0.0197 (4)	0.0165 (4)
S2	0.0397 (5)	0.0307 (6)	0.0246 (4)	0.0109 (4)	0.0103 (4)	0.0081 (4)
Cl1	0.0433 (5)	0.0439 (6)	0.0251 (4)	0.0102 (4)	0.0174 (4)	0.0052 (4)
Sn1	0.02990 (14)	0.02902 (18)	0.01925 (13)	0.00717 (9)	0.00978 (9)	0.00827 (10)

Geometric parameters (Å, º)

C1—C2	1.382 (6)	C14—C18	1.521 (6)
C1—C6	1.401 (6)	C15—N1	1.318 (6)
C1—Sn1	2.134 (4)	C15—C16	1.507 (5)
C2—C3	1.391 (6)	C16—C17	1.523 (7)
C2—H2A	0.9500	C16—H16B	0.9900
C3—C4	1.374 (8)	C16—H16A	0.9900
C3—H3A	0.9500	C17—C18	1.531 (6)
C4—C5	1.376 (9)	C17—H17B	0.9900
C4—H4A	0.9500	C17—H17A	0.9900
C5—C6	1.395 (7)	C18—H18B	0.9900
C5—H5A	0.9500	C18—H18A	0.9900
C6—H6A	0.9500	C19—C20	1.462 (8)
C7—C12	1.376 (5)	C19—N1	1.489 (5)
C7—C8	1.384 (6)	C19—C22	1.569 (8)
C7—Sn1	2.143 (4)	C19—H19A	1.0000
C8—C9	1.385 (7)	C20—C21	1.489 (8)
C8—H8A	0.9500	C20—H20B	0.9900
C9—C10	1.366 (7)	C20—H20A	0.9900
C9—H9A	0.9500	C21—H21A	0.9800
C10—C11	1.372 (7)	C21—H21B	0.9800
C10—H10A	0.9500	C21—H21C	0.9800
C11—C12	1.389 (7)	C22—H22C	0.9800
C11—H11A	0.9500	C22—H22B	0.9800
C12—H12A	0.9500	C22—H22A	0.9800
C13—C14	1.383 (5)	N1—H1	0.8800
C13—S1	1.724 (4)	S1—Sn1	2.7139 (9)
C13—S2	1.757 (4)	S2—Sn1	2.4538 (10)
C14—C15	1.418 (5)	Cl1—Sn1	2.4562 (9)
C2—C1—C6	118.8 (4)	C16—C17—C18	105.3 (4)
C2—C1—Sn1	121.9 (3)	C16—C17—H17B	110.7
C6—C1—Sn1	119.3 (3)	C18—C17—H17B	110.7
C1—C2—C3	121.2 (4)	C16—C17—H17A	110.7
C1—C2—H2A	119.4	C18—C17—H17A	110.7
C3—C2—H2A	119.4	H17B—C17—H17A	108.8
C4—C3—C2	119.7 (5)	C14—C18—C17	103.7 (4)
C4—C3—H3A	120.2	C14—C18—H18B	111.0
C2—C3—H3A	120.2	C17—C18—H18B	111.0
C3—C4—C5	120.1 (4)	C14—C18—H18A	111.0
C3—C4—H4A	119.9	C17—C18—H18A	111.0
C5—C4—H4A	119.9	H18B—C18—H18A	109.0
C4—C5—C6	120.7 (5)	C20—C19—N1	109.5 (4)
C4—C5—H5A	119.7	C20—C19—C22	113.7 (5)
C6—C5—H5A	119.7	N1—C19—C22	109.0 (4)
C5—C6—C1	119.5 (5)	C20—C19—H19A	108.2
C5—C6—H6A	120.2	N1—C19—H19A	108.2
C1—C6—H6A	120.2	C22—C19—H19A	108.2
C12—C7—C8	118.0 (4)	C19—C20—C21	114.1 (5)
C12—C7—Sn1	120.2 (3)	C19—C20—H20B	108.7
C8—C7—Sn1	121.8 (3)	C21—C20—H20B	108.7
C7—C8—C9	121.2 (4)	C19—C20—H20A	108.7
C7—C8—H8A	119.4	C21—C20—H20A	108.7
C9—C8—H8A	119.4	H20B—C20—H20A	107.6
C10—C9—C8	120.1 (5)	C20—C21—H21A	109.5
C10—C9—H9A	119.9	C20—C21—H21B	109.5
C8—C9—H9A	119.9	H21A—C21—H21B	109.5
C9—C10—C11	119.6 (5)	C20—C21—H21C	109.5
C9—C10—H10A	120.2	H21A—C21—H21C	109.5
C11—C10—H10A	120.2	H21B—C21—H21C	109.5
C10—C11—C12	120.3 (4)	C19—C22—H22C	109.5
C10—C11—H11A	119.9	C19—C22—H22B	109.5
C12—C11—H11A	119.9	H22C—C22—H22B	109.5
C7—C12—C11	120.8 (4)	C19—C22—H22A	109.5
C7—C12—H12A	119.6	H22C—C22—H22A	109.5
C11—C12—H12A	119.6	H22B—C22—H22A	109.5
C14—C13—S1	126.1 (3)	C15—N1—C19	128.3 (4)
C14—C13—S2	118.5 (3)	C15—N1—H1	115.9
S1—C13—S2	115.5 (2)	C19—N1—H1	115.9
C13—C14—C15	126.7 (4)	C13—S1—Sn1	83.73 (12)
C13—C14—C18	124.7 (3)	C13—S2—Sn1	91.38 (13)
C15—C14—C18	108.5 (3)	C1—Sn1—C7	121.10 (14)
N1—C15—C14	126.8 (3)	C1—Sn1—S2	116.28 (11)
N1—C15—C16	122.9 (4)	C7—Sn1—S2	120.92 (10)
C14—C15—C16	110.3 (4)	C1—Sn1—Cl1	97.18 (10)
C15—C16—C17	103.9 (3)	C7—Sn1—Cl1	97.93 (10)
C15—C16—H16B	111.0	S2—Sn1—Cl1	87.67 (3)
C17—C16—H16B	111.0	C1—Sn1—S1	92.31 (10)
C15—C16—H16A	111.0	C7—Sn1—S1	95.10 (10)
C17—C16—H16A	111.0	S2—Sn1—S1	69.22 (3)
H16B—C16—H16A	109.0	Cl1—Sn1—S1	156.87 (3)
C6—C1—C2—C3	−1.7 (6)	C14—C15—N1—C19	176.7 (5)
Sn1—C1—C2—C3	175.2 (3)	C16—C15—N1—C19	−1.3 (8)
C1—C2—C3—C4	0.5 (7)	C20—C19—N1—C15	114.8 (6)
C2—C3—C4—C5	0.5 (8)	C22—C19—N1—C15	−120.3 (5)
C3—C4—C5—C6	−0.3 (8)	C14—C13—S1—Sn1	175.1 (3)
C4—C5—C6—C1	−0.9 (8)	S2—C13—S1—Sn1	−4.19 (18)
C2—C1—C6—C5	1.9 (6)	C14—C13—S2—Sn1	−174.8 (3)
Sn1—C1—C6—C5	−175.2 (4)	S1—C13—S2—Sn1	4.61 (19)
C12—C7—C8—C9	0.4 (8)	C2—C1—Sn1—C7	126.1 (3)
Sn1—C7—C8—C9	−178.0 (4)	C6—C1—Sn1—C7	−57.0 (4)
C7—C8—C9—C10	−0.1 (9)	C2—C1—Sn1—S2	−68.6 (3)
C8—C9—C10—C11	−0.1 (9)	C6—C1—Sn1—S2	108.3 (3)
C9—C10—C11—C12	0.0 (8)	C2—C1—Sn1—Cl1	22.3 (3)
C8—C7—C12—C11	−0.6 (7)	C6—C1—Sn1—Cl1	−160.8 (3)
Sn1—C7—C12—C11	177.9 (4)	C2—C1—Sn1—S1	−136.5 (3)
C10—C11—C12—C7	0.4 (8)	C6—C1—Sn1—S1	40.4 (3)
S1—C13—C14—C15	0.1 (6)	C12—C7—Sn1—C1	−94.3 (3)
S2—C13—C14—C15	179.4 (3)	C8—C7—Sn1—C1	84.1 (4)
S1—C13—C14—C18	−179.3 (3)	C12—C7—Sn1—S2	101.1 (3)
S2—C13—C14—C18	0.1 (5)	C8—C7—Sn1—S2	−80.5 (4)
C13—C14—C15—N1	4.7 (7)	C12—C7—Sn1—Cl1	9.1 (3)
C18—C14—C15—N1	−175.9 (4)	C8—C7—Sn1—Cl1	−172.6 (4)
C13—C14—C15—C16	−177.1 (4)	C12—C7—Sn1—S1	169.9 (3)
C18—C14—C15—C16	2.3 (5)	C8—C7—Sn1—S1	−11.7 (4)
N1—C15—C16—C17	−166.2 (5)	C13—S2—Sn1—C1	−84.82 (16)
C14—C15—C16—C17	15.5 (5)	C13—S2—Sn1—C7	80.48 (16)
C15—C16—C17—C18	−26.9 (5)	C13—S2—Sn1—Cl1	178.32 (12)
C13—C14—C18—C17	160.4 (4)	C13—S2—Sn1—S1	−2.83 (12)
C15—C14—C18—C17	−19.0 (5)	C13—S1—Sn1—C1	120.20 (16)
C16—C17—C18—C14	28.2 (5)	C13—S1—Sn1—C7	−118.30 (15)
N1—C19—C20—C21	−55.6 (6)	C13—S1—Sn1—S2	2.90 (12)
C22—C19—C20—C21	−177.8 (4)	C13—S1—Sn1—Cl1	5.83 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1	0.88	2.31	3.045 (3)	141
C19—H19A···Cl1^i	1.00	2.83	3.737 (5)	152

Symmetry code: (i) x, y, z+1.