Redetermination of L-(–)-di­chloro(N,N-diethyl­di­thio­carbamato)(β-menthoxy­carbonyl­ethyl)­tin(IV)

The crystal structure of the chiral title compound, [Sn(C₅H₁₀NS₂)(C₁₃H₂₃O₂)Cl₂], has been determined in space group P2₁2₁2₁. The Sn atom is in a distorted octahedral geometry within a CCl₂OS₂ donor set.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.035
• wR factor = 0.079
• Data-to-parameter ratio = 24.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.88 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Sn1    -   S2      ..       6.12 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Sn1

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               5665
           Count of symmetry unique reflns         3278
           Completeness (_total/calc)            172.82%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2387
           Fraction of Friedel pairs measured     0.728
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: averaging the two molecules described in P2₁ (Lai et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97.

L-(-)-dichloro(N,N-diethyldithiocarbamato)(β-menthoxycarbonylethyl)tin(IV)

Crystal data

[Sn(C5H10NS2)(C13H23O2)Cl2]	F(000) = 1120
Mr = 549.16	Dx = 1.440 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5645 reflections
a = 10.305 (1) Å	θ = 2.6–24.7°
b = 12.088 (1) Å	µ = 1.40 mm^−1
c = 20.341 (2) Å	T = 295 K
V = 2533.8 (4) Å^3	Irregular block, colorless
Z = 4	0.27 × 0.12 × 0.09 mm

Data collection

Bruker APEX area-detector diffractometer	5665 independent reflections
Radiation source: fine-focus sealed tube	5005 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −13→12
Tmin = 0.675, Tmax = 0.885	k = −15→14
15820 measured reflections	l = −23→26

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0407P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
5665 reflections	Δρmax = 0.52 e Å^−3
235 parameters	Δρmin = −0.63 e Å^−3
0 restraints	Absolute structure: Flack parameter from 2417 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (2)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.17309 (2)	0.60715 (2)	0.91989 (1)	0.04835 (8)
Cl1	−0.0354 (1)	0.6951 (1)	0.91492 (6)	0.0790 (4)
Cl2	0.1368 (1)	0.5348 (1)	1.02851 (5)	0.0743 (3)
S1	0.1152 (1)	0.42765 (8)	0.87082 (4)	0.0531 (2)
S2	0.2102 (1)	0.61134 (8)	0.78885 (4)	0.0559 (2)
O1	0.3820 (3)	0.5265 (2)	0.9307 (2)	0.0592 (7)
O2	0.5902 (3)	0.5712 (2)	0.9187 (2)	0.0665 (7)
N1	0.1387 (3)	0.4170 (2)	0.7412 (1)	0.0476 (7)
C1	0.1535 (3)	0.4794 (3)	0.7936 (2)	0.042 (1)
C2	0.0906 (5)	0.3015 (3)	0.7450 (2)	0.068 (1)
C3	0.1971 (6)	0.2185 (4)	0.7435 (3)	0.100 (2)
C4	0.1707 (5)	0.4560 (3)	0.6743 (2)	0.059 (1)
C5	0.0567 (5)	0.5063 (4)	0.6405 (2)	0.080 (1)
C6	0.3003 (4)	0.7448 (3)	0.9329 (2)	0.062 (1)
C7	0.4351 (4)	0.7150 (3)	0.9106 (2)	0.065 (1)
C8	0.4669 (4)	0.5955 (3)	0.9212 (2)	0.052 (1)
C9	0.6284 (4)	0.4552 (3)	0.9292 (2)	0.062 (1)
C10	0.7034 (5)	0.4506 (4)	0.9926 (2)	0.077 (1)
C11	0.7456 (5)	0.3318 (4)	1.0079 (3)	0.084 (2)
C12	0.8224 (5)	0.2860 (4)	0.9492 (3)	0.090 (2)
C13	0.7502 (6)	0.2972 (4)	0.8859 (3)	0.087 (2)
C14	0.7082 (4)	0.4176 (3)	0.8709 (2)	0.065 (1)
C15	0.8250 (7)	0.3278 (6)	1.0708 (3)	0.123 (2)
C16	0.6414 (5)	0.4335 (4)	0.8039 (2)	0.076 (1)
C17	0.7361 (6)	0.4152 (4)	0.7470 (3)	0.106 (2)
C18	0.5197 (6)	0.3659 (4)	0.7937 (3)	0.102 (2)
H2a	0.0414	0.2925	0.7853	0.081*
H2b	0.0324	0.2879	0.7084	0.081*
H3a	0.1610	0.1454	0.7459	0.150*
H3b	0.2538	0.2302	0.7803	0.150*
H3c	0.2454	0.2262	0.7034	0.150*
H4a	0.2021	0.3941	0.6484	0.071*
H4b	0.2398	0.5103	0.6769	0.071*
H5a	0.0816	0.5301	0.5973	0.120*
H5b	0.0264	0.5686	0.6654	0.120*
H5c	−0.0115	0.4524	0.6371	0.120*
H6a	0.2688	0.8074	0.9077	0.075*
H6b	0.3020	0.7660	0.9789	0.075*
H7a	0.4436	0.7321	0.8643	0.078*
H7b	0.4973	0.7600	0.9344	0.078*
H9a	0.5505	0.4091	0.9329	0.074*
H10a	0.6497	0.4782	1.0282	0.092*
H10b	0.7794	0.4976	0.9893	0.092*
H11	0.6677	0.2864	1.0139	0.101*
H12a	0.9043	0.3252	0.9459	0.107*
H12b	0.8416	0.2085	0.9569	0.107*
H13a	0.6736	0.2506	0.8875	0.105*
H13b	0.8047	0.2707	0.8503	0.105*
H14	0.7872	0.4627	0.8703	0.077*
H15a	0.8510	0.2529	1.0794	0.185*
H15b	0.7734	0.3545	1.1068	0.185*
H15c	0.9006	0.3734	1.0660	0.185*
H16	0.6150	0.5113	0.8018	0.091*
H17a	0.6914	0.4251	0.7060	0.159*
H17b	0.7704	0.3414	0.7492	0.159*
H17c	0.8059	0.4675	0.7500	0.159*
H18a	0.4611	0.3781	0.8297	0.153*
H18b	0.5418	0.2888	0.7916	0.153*
H18c	0.4788	0.3877	0.7533	0.153*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0547 (1)	0.0534 (1)	0.0370 (1)	0.0130 (1)	−0.0051 (1)	−0.0067 (1)
Cl1	0.0731 (7)	0.1109 (9)	0.0532 (6)	0.0450 (7)	0.0044 (6)	0.0135 (7)
Cl2	0.0935 (9)	0.0908 (8)	0.0387 (5)	0.0229 (7)	−0.0050 (5)	0.0052 (5)
S1	0.0627 (6)	0.0578 (6)	0.0389 (5)	−0.0100 (5)	0.0045 (4)	0.0016 (4)
S2	0.0809 (7)	0.0443 (4)	0.0426 (5)	−0.0103 (5)	0.0046 (4)	−0.0040 (4)
O1	0.048 (1)	0.047 (1)	0.082 (2)	0.001 (1)	−0.002 (1)	−0.001 (1)
O2	0.052 (2)	0.050 (1)	0.098 (2)	−0.003 (1)	0.014 (2)	−0.007 (2)
N1	0.058 (2)	0.045 (2)	0.039 (2)	−0.010 (1)	0.004 (1)	−0.005 (1)
C1	0.041 (2)	0.048 (2)	0.039 (2)	−0.001 (2)	0.001 (1)	−0.003 (1)
C2	0.090 (3)	0.059 (3)	0.055 (2)	−0.025 (2)	−0.002 (2)	−0.010 (2)
C3	0.132 (6)	0.059 (3)	0.110 (4)	0.017 (3)	−0.033 (4)	−0.007 (3)
C4	0.078 (3)	0.062 (2)	0.037 (2)	−0.007 (2)	0.009 (2)	−0.004 (2)
C5	0.099 (4)	0.086 (3)	0.055 (3)	0.001 (3)	−0.005 (3)	0.011 (2)
C6	0.084 (3)	0.041 (2)	0.062 (2)	0.012 (2)	−0.020 (2)	−0.019 (2)
C7	0.079 (3)	0.043 (2)	0.074 (3)	−0.005 (2)	−0.010 (3)	−0.012 (2)
C8	0.055 (2)	0.049 (2)	0.053 (2)	0.005 (2)	0.000 (2)	−0.012 (2)
C9	0.050 (2)	0.047 (2)	0.088 (3)	0.000 (2)	0.017 (2)	−0.001 (2)
C10	0.077 (4)	0.078 (3)	0.076 (3)	0.000 (3)	0.020 (3)	−0.001 (2)
C11	0.070 (3)	0.079 (3)	0.104 (4)	−0.002 (3)	0.020 (3)	0.024 (3)
C12	0.074 (3)	0.079 (3)	0.116 (4)	0.017 (3)	0.022 (3)	0.024 (3)
C13	0.085 (4)	0.064 (3)	0.113 (4)	0.017 (3)	0.028 (3)	0.001 (3)
C14	0.052 (2)	0.055 (2)	0.086 (3)	0.002 (2)	0.016 (2)	−0.002 (2)
C15	0.120 (5)	0.141 (5)	0.108 (5)	0.002 (5)	−0.003 (5)	0.043 (4)
C16	0.089 (4)	0.053 (2)	0.086 (3)	0.002 (2)	0.012 (3)	−0.007 (2)
C17	0.156 (6)	0.063 (3)	0.098 (4)	0.002 (3)	0.038 (4)	−0.007 (3)
C18	0.104 (4)	0.101 (4)	0.101 (4)	−0.012 (4)	−0.006 (3)	−0.019 (3)

Geometric parameters (Å, º)

Sn1—C6	2.135 (4)	C3—H3b	0.96
Sn1—O1	2.374 (3)	C3—H3c	0.96
Sn1—S1	2.462 (1)	C4—H4a	0.97
Sn1—S2	2.693 (1)	C4—H4b	0.97
Sn1—Cl1	2.399 (1)	C5—H5a	0.96
Sn1—Cl2	2.405 (1)	C5—H5b	0.96
S1—C1	1.736 (3)	C5—H5c	0.96
S2—C1	1.701 (3)	C6—H6a	0.97
O1—C8	1.224 (4)	C6—H6b	0.97
O2—C8	1.305 (5)	C7—H7a	0.97
O2—C9	1.472 (5)	C7—H7b	0.97
N1—C1	1.315 (4)	C9—H9a	0.98
N1—C4	1.478 (4)	C10—H10a	0.97
N1—C2	1.483 (5)	C10—H10b	0.97
C2—C3	1.488 (7)	C11—H11	0.98
C4—C5	1.490 (6)	C12—H12a	0.97
C6—C7	1.505 (6)	C12—H12b	0.97
C7—C8	1.496 (5)	C13—H13a	0.97
C9—C10	1.504 (6)	C13—H13b	0.97
C9—C14	1.514 (6)	C14—H14	0.98
C10—C11	1.532 (7)	C15—H15a	0.96
C11—C15	1.520 (7)	C15—H15b	0.96
C11—C12	1.534 (7)	C15—H15c	0.96
C12—C13	1.495 (7)	C16—H16	0.98
C13—C14	1.550 (6)	C17—H17a	0.96
C14—C16	1.538 (7)	C17—H17b	0.96
C16—C18	1.511 (7)	C17—H17c	0.96
C16—C17	1.531 (7)	C18—H18a	0.96
C2—H2a	0.97	C18—H18b	0.96
C2—H2b	0.97	C18—H18c	0.96
C3—H3a	0.96
C6—Sn1—O1	75.6 (1)	H4a—C4—H4b	107.9
C6—Sn1—S1	152.4 (1)	C4—C5—H5a	109.5
C6—Sn1—S2	91.2 (1)	C4—C5—H5b	109.5
C6—Sn1—Cl1	102.1 (1)	H5a—C5—H5b	109.5
C6—Sn1—Cl2	105.3 (1)	C4—C5—H5c	109.5
O1—Sn1—S1	84.02 (7)	H5a—C5—H5c	109.5
O1—Sn1—S2	88.32 (8)	H5b—C5—H5c	109.5
O1—Sn1—Cl1	176.49 (8)	C7—C6—H6a	109.7
O1—Sn1—Cl2	84.63 (8)	Sn1—C6—H6a	109.7
S1—Sn1—S2	69.50 (3)	C7—C6—H6b	109.7
S1—Sn1—Cl1	98.98 (4)	Sn1—C6—H6b	109.7
S1—Sn1—Cl2	90.83 (4)	H6a—C6—H6b	108.2
S2—Sn1—Cl1	94.43 (4)	C8—C7—H7a	109.0
S2—Sn1—Cl2	159.72 (4)	C6—C7—H7a	109.0
Cl1—Sn1—Cl2	93.47 (4)	C8—C7—H7b	109.0
C1—S1—Sn1	89.7 (1)	C6—C7—H7b	109.0
C1—S2—Sn1	83.0 (1)	H7a—C7—H7b	107.8
C8—O1—Sn1	110.7 (2)	O2—C9—H9a	109.5
C8—O2—C9	118.0 (3)	C10—C9—H9a	109.5
C1—N1—C4	122.6 (3)	C14—C9—H9a	109.5
C1—N1—C2	122.4 (3)	C9—C10—H10a	109.5
C4—N1—C2	115.0 (3)	C11—C10—H10a	109.5
N1—C1—S2	122.1 (3)	C9—C10—H10b	109.5
N1—C1—S1	120.0 (3)	C11—C10—H10b	109.5
S2—C1—S1	117.9 (2)	H10a—C10—H10b	108.1
C3—C2—N1	112.8 (4)	C15—C11—H11	108.5
N1—C4—C5	112.2 (4)	C10—C11—H11	108.5
C7—C6—Sn1	110.0 (2)	C12—C11—H11	108.5
C8—C7—C6	113.0 (4)	C13—C12—H12a	109.1
O1—C8—O2	123.3 (3)	C11—C12—H12a	109.1
O1—C8—C7	121.6 (3)	C13—C12—H12b	109.1
O2—C8—C7	115.1 (4)	C11—C12—H12b	109.1
O2—C9—C10	107.3 (3)	H12a—C12—H12b	107.9
O2—C9—C14	108.5 (3)	C12—C13—H13a	108.9
C10—C9—C14	112.5 (4)	C14—C13—H13a	108.9
C9—C10—C11	110.8 (4)	C12—C13—H13b	108.9
C15—C11—C10	110.7 (5)	C14—C13—H13b	108.9
C15—C11—C12	111.5 (5)	H13a—C13—H13b	107.8
C10—C11—C12	109.1 (4)	C9—C14—H14	107.0
C13—C12—C11	112.4 (4)	C16—C14—H14	107.0
C12—C13—C14	113.2 (4)	C13—C14—H14	107.0
C9—C14—C16	114.4 (4)	C11—C15—H15a	109.5
C9—C14—C13	106.2 (4)	C11—C15—H15b	109.5
C16—C14—C13	114.6 (4)	H15a—C15—H15b	109.5
C18—C16—C17	110.3 (4)	C11—C15—H15c	109.5
C18—C16—C14	115.2 (4)	H15a—C15—H15c	109.5
C17—C16—C14	111.5 (4)	H15b—C15—H15c	109.5
C3—C2—H2a	109.0	C18—C16—H16	106.4
N1—C2—H2a	109.0	C17—C16—H16	106.4
C3—C2—H2b	109.0	C14—C16—H16	106.4
N1—C2—H2b	109.0	C16—C17—H17a	109.5
H2a—C2—H2b	107.8	C16—C17—H17b	109.5
C2—C3—H3a	109.5	H17a—C17—H17b	109.5
C2—C3—H3b	109.5	C16—C17—H17c	109.5
H3a—C3—H3b	109.5	H17a—C17—H17c	109.5
C2—C3—H3c	109.5	H17b—C17—H17c	109.5
H3a—C3—H3c	109.5	C16—C18—H18a	109.5
H3b—C3—H3c	109.5	C16—C18—H18b	109.5
N1—C4—H4a	109.2	H18a—C18—H18b	109.5
C5—C4—H4a	109.2	C16—C18—H18c	109.5
N1—C4—H4b	109.2	H18a—C18—H18c	109.5
C5—C4—H4b	109.2	H18b—C18—H18c	109.5
C6—Sn1—S1—C1	−49.1 (3)	S1—Sn1—C6—C7	−18.4 (5)
O1—Sn1—S1—C1	−91.4 (1)	S2—Sn1—C6—C7	−62.6 (3)
Cl1—Sn1—S1—C1	90.4 (1)	Sn1—C6—C7—C8	−32.0 (5)
Cl2—Sn1—S1—C1	−175.9 (1)	Sn1—O1—C8—O2	−174.1 (3)
S2—Sn1—S1—C1	−1.0 (1)	Sn1—O1—C8—C7	5.2 (5)
C6—Sn1—S2—C1	160.8 (2)	C9—O2—C8—O1	−1.1 (6)
O1—Sn1—S2—C1	85.3 (1)	C9—O2—C8—C7	179.5 (4)
Cl1—Sn1—S2—C1	−96.9 (1)	C6—C7—C8—O1	17.4 (6)
Cl2—Sn1—S2—C1	15.7 (2)	C6—C7—C8—O2	−163.3 (4)
S1—Sn1—S2—C1	1.0 (1)	C8—O2—C9—C10	−113.5 (4)
C6—Sn1—O1—C8	−17.9 (3)	C8—O2—C9—C14	124.7 (4)
Cl2—Sn1—O1—C8	−125.3 (3)	O2—C9—C10—C11	179.3 (4)
S1—Sn1—O1—C8	143.3 (3)	C14—C9—C10—C11	−61.5 (5)
S2—Sn1—O1—C8	73.8 (3)	C9—C10—C11—C15	178.2 (4)
C4—N1—C1—S2	0.3 (5)	C9—C10—C11—C12	55.3 (5)
C2—N1—C1—S2	179.4 (3)	C15—C11—C12—C13	−175.6 (5)
C4—N1—C1—S1	−179.5 (3)	C10—C11—C12—C13	−53.1 (6)
C2—N1—C1—S1	−0.5 (5)	C11—C12—C13—C14	55.7 (6)
Sn1—S2—C1—N1	178.6 (3)	O2—C9—C14—C16	−54.8 (5)
Sn1—S2—C1—S1	−1.5 (2)	C10—C9—C14—C16	−173.3 (3)
Sn1—S1—C1—N1	−178.5 (3)	O2—C9—C14—C13	177.7 (4)
Sn1—S1—C1—S2	1.6 (2)	C10—C9—C14—C13	59.2 (5)
C1—N1—C2—C3	−98.2 (5)	C12—C13—C14—C9	−56.4 (5)
C4—N1—C2—C3	80.9 (5)	C12—C13—C14—C16	176.2 (4)
C1—N1—C4—C5	−92.0 (5)	C9—C14—C16—C18	−64.3 (5)
C2—N1—C4—C5	88.9 (4)	C13—C14—C16—C18	58.7 (5)
O1—Sn1—C6—C7	25.3 (3)	C9—C14—C16—C17	169.0 (4)
Cl1—Sn1—C6—C7	−157.4 (3)	C13—C14—C16—C17	−68.0 (5)
Cl2—Sn1—C6—C7	105.5 (3)