Bromidobis(pyrrolidine-1-dithio­carboxyl­ato-κ²S,S′)anti­mony(III)

In the title compound, [SbBr(C₅H₈NS₂)₂], the Sb^III ion is coordinated by the four S atoms [Sb—S = 2.4616 (11)–2.9194 (13) Å] from two pyrrolidine-1-dithio­carboxyl­ate ligands and a Br atom [Sb—Br = 2.8159 (7) Å] in a distorted trigonal–bipyramidal geometry. In the crystal structure, the mol­ecules are associated into dimers with short inter­molecular Sb...S contacts of 3.7350 (13) Å.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.027
• wR factor = 0.073
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Sb1    -   Br1     ..       5.00 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bromidobis(pyrrolidine-1-dithiocarboxylato-κ²S,S')antimony(III)

Crystal data

[SbBr(C5H8NS2)2]	Z = 2
Mr = 494.19	F(000) = 480
Triclinic, P1	Dx = 2.002 Mg m^−3
a = 6.4655 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.471 (2) Å	Cell parameters from 2564 reflections
c = 13.394 (3) Å	θ = 3.2–27.3°
α = 110.716 (3)°	µ = 4.62 mm^−1
β = 92.361 (4)°	T = 298 K
γ = 102.869 (3)°	Prism, yellow
V = 819.6 (3) Å^3	0.30 × 0.13 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2846 independent reflections
Radiation source: fine-focus sealed tube	2398 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.338, Tmax = 0.738	k = −12→12
4258 measured reflections	l = −13→15

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0411P)^2 + 0.1634P] where P = (Fo^2 + 2Fc^2)/3
2846 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Experimental. Anal. Calcd (%) for C₁₀H₁₆N₂S₄SbBr (Mr=499.15): C,24.30 H,3.26 N 5.67 Found: C, 24.41; H, 3.34; N, 5.52.

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
Sb1	0.52221 (4)	0.30318 (3)	0.33026 (2)	0.04874 (11)
Br1	0.43771 (8)	0.49518 (5)	0.24053 (4)	0.06770 (16)
N1	0.3437 (5)	−0.1226 (3)	0.0798 (2)	0.0471 (8)
N2	0.1383 (5)	0.2405 (3)	0.5726 (3)	0.0485 (8)
S1	0.26887 (16)	0.12525 (10)	0.17604 (8)	0.0517 (3)
S2	0.67472 (16)	0.05348 (11)	0.22020 (9)	0.0562 (3)
S3	0.42675 (18)	0.15338 (11)	0.44839 (9)	0.0565 (3)
S4	0.21326 (18)	0.36920 (11)	0.43382 (9)	0.0546 (3)
C1	0.4265 (6)	0.0043 (4)	0.1517 (3)	0.0418 (8)
C2	0.1337 (7)	−0.1668 (4)	0.0134 (3)	0.0592 (11)
H2A	0.1256	−0.1057	−0.0260	0.071*
H2B	0.0183	−0.1660	0.0575	0.071*
C3	0.1247 (9)	−0.3154 (5)	−0.0625 (4)	0.0859 (17)
H3A	−0.0210	−0.3738	−0.0797	0.103*
H3B	0.1790	−0.3148	−0.1288	0.103*
C4	0.2615 (9)	−0.3680 (5)	−0.0034 (4)	0.0815 (15)
H4A	0.3122	−0.4442	−0.0526	0.098*
H4B	0.1842	−0.4015	0.0468	0.098*
C5	0.4443 (7)	−0.2415 (4)	0.0553 (4)	0.0622 (11)
H5A	0.5048	−0.2469	0.1207	0.075*
H5B	0.5561	−0.2330	0.0102	0.075*
C6	0.2459 (6)	0.2520 (4)	0.4948 (3)	0.0486 (9)
C7	−0.0181 (7)	0.3203 (4)	0.6177 (4)	0.0583 (11)
H7A	−0.1223	0.3153	0.5613	0.070*
H7B	0.0519	0.4186	0.6596	0.070*
C8	−0.1218 (9)	0.2467 (6)	0.6883 (5)	0.0812 (15)
H8A	−0.1678	0.3123	0.7491	0.097*
H8B	−0.2449	0.1703	0.6478	0.097*
C9	0.0453 (8)	0.1916 (6)	0.7248 (4)	0.0727 (13)
H9A	−0.0188	0.1107	0.7427	0.087*
H9B	0.1365	0.2636	0.7879	0.087*
C10	0.1725 (7)	0.1493 (4)	0.6318 (3)	0.0541 (10)
H10A	0.3230	0.1678	0.6570	0.065*
H10B	0.1188	0.0501	0.5869	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sb1	0.04904 (18)	0.04313 (17)	0.05149 (18)	0.00816 (12)	−0.00045 (12)	0.01751 (12)
Br1	0.0777 (3)	0.0505 (3)	0.0797 (3)	0.0148 (2)	0.0020 (3)	0.0318 (2)
N1	0.0466 (19)	0.0465 (18)	0.0462 (18)	0.0085 (14)	0.0047 (15)	0.0171 (15)
N2	0.0493 (19)	0.0482 (18)	0.0522 (19)	0.0138 (15)	0.0048 (16)	0.0231 (16)
S1	0.0478 (6)	0.0480 (6)	0.0562 (6)	0.0148 (4)	−0.0059 (5)	0.0156 (5)
S2	0.0397 (5)	0.0571 (6)	0.0681 (7)	0.0127 (4)	−0.0013 (5)	0.0195 (5)
S3	0.0686 (7)	0.0548 (6)	0.0552 (6)	0.0267 (5)	0.0090 (5)	0.0246 (5)
S4	0.0655 (7)	0.0513 (6)	0.0562 (6)	0.0234 (5)	0.0080 (5)	0.0257 (5)
C1	0.0374 (19)	0.045 (2)	0.048 (2)	0.0086 (16)	0.0072 (16)	0.0237 (18)
C2	0.054 (3)	0.065 (3)	0.049 (2)	0.005 (2)	−0.006 (2)	0.019 (2)
C3	0.095 (4)	0.060 (3)	0.077 (4)	−0.007 (3)	−0.016 (3)	0.015 (3)
C4	0.106 (4)	0.051 (3)	0.074 (3)	0.011 (3)	0.008 (3)	0.013 (2)
C5	0.069 (3)	0.051 (2)	0.066 (3)	0.021 (2)	0.014 (2)	0.017 (2)
C6	0.049 (2)	0.042 (2)	0.050 (2)	0.0102 (17)	−0.0050 (19)	0.0152 (18)
C7	0.054 (3)	0.056 (2)	0.071 (3)	0.020 (2)	0.010 (2)	0.027 (2)
C8	0.080 (4)	0.091 (4)	0.102 (4)	0.038 (3)	0.042 (3)	0.058 (3)
C9	0.077 (3)	0.084 (3)	0.080 (3)	0.031 (3)	0.025 (3)	0.050 (3)
C10	0.057 (3)	0.052 (2)	0.063 (3)	0.0173 (19)	0.008 (2)	0.031 (2)

Geometric parameters (Å, º)

Sb1—S1	2.4616 (11)	C3—C4	1.477 (7)
Sb1—S4	2.5606 (12)	C3—H3A	0.9700
Sb1—S3	2.5980 (11)	C3—H3B	0.9700
Sb1—Br1	2.8159 (7)	C4—C5	1.503 (6)
Sb1—S2	2.9194 (13)	C4—H4A	0.9700
Sb1—S4^i	3.7350 (13)	C4—H4B	0.9700
N1—C1	1.310 (5)	C5—H5A	0.9700
N1—C5	1.473 (5)	C5—H5B	0.9700
N1—C2	1.476 (5)	C7—C8	1.508 (6)
N2—C6	1.301 (5)	C7—H7A	0.9700
N2—C7	1.469 (5)	C7—H7B	0.9700
N2—C10	1.485 (5)	C8—C9	1.474 (7)
S1—C1	1.749 (4)	C8—H8A	0.9700
S2—C1	1.690 (4)	C8—H8B	0.9700
S3—C6	1.721 (4)	C9—C10	1.511 (6)
S4—C6	1.740 (4)	C9—H9A	0.9700
C2—C3	1.514 (6)	C9—H9B	0.9700
C2—H2A	0.9700	C10—H10A	0.9700
C2—H2B	0.9700	C10—H10B	0.9700
S1—Sb1—S4	91.05 (4)	C3—C4—C5	104.0 (4)
S1—Sb1—S3	91.90 (4)	C3—C4—H4A	111.0
S4—Sb1—S3	69.88 (4)	C5—C4—H4A	111.0
S1—Sb1—Br1	84.31 (3)	C3—C4—H4B	111.0
S4—Sb1—Br1	81.77 (3)	C5—C4—H4B	111.0
S3—Sb1—Br1	151.34 (3)	H4A—C4—H4B	109.0
S1—Sb1—S2	66.56 (3)	N1—C5—C4	103.2 (4)
S4—Sb1—S2	139.34 (3)	N1—C5—H5A	111.1
S3—Sb1—S2	77.13 (4)	C4—C5—H5A	111.1
Br1—Sb1—S2	125.99 (3)	N1—C5—H5B	111.1
S1—Sb1—S4^i	163.39 (3)	C4—C5—H5B	111.1
S4—Sb1—S4^i	76.04 (4)	H5A—C5—H5B	109.1
S3—Sb1—S4^i	93.34 (4)	N2—C6—S3	121.8 (3)
Br1—Sb1—S4^i	83.54 (3)	N2—C6—S4	121.0 (3)
S2—Sb1—S4^i	130.02 (3)	S3—C6—S4	117.2 (2)
C1—N1—C5	125.0 (3)	N2—C7—C8	103.0 (3)
C1—N1—C2	124.4 (3)	N2—C7—H7A	111.2
C5—N1—C2	110.6 (3)	C8—C7—H7A	111.2
C6—N2—C7	125.6 (3)	N2—C7—H7B	111.2
C6—N2—C10	122.7 (3)	C8—C7—H7B	111.2
C7—N2—C10	111.6 (3)	H7A—C7—H7B	109.1
C1—S1—Sb1	93.30 (13)	C9—C8—C7	105.2 (4)
C1—S2—Sb1	79.71 (13)	C9—C8—H8A	110.7
C6—S3—Sb1	85.88 (14)	C7—C8—H8A	110.7
C6—S4—Sb1	86.68 (15)	C9—C8—H8B	110.7
N1—C1—S2	122.8 (3)	C7—C8—H8B	110.7
N1—C1—S1	117.3 (3)	H8A—C8—H8B	108.8
S2—C1—S1	119.9 (2)	C8—C9—C10	105.8 (4)
N1—C2—C3	103.2 (4)	C8—C9—H9A	110.6
N1—C2—H2A	111.1	C10—C9—H9A	110.6
C3—C2—H2A	111.1	C8—C9—H9B	110.6
N1—C2—H2B	111.1	C10—C9—H9B	110.6
C3—C2—H2B	111.1	H9A—C9—H9B	108.7
H2A—C2—H2B	109.1	N2—C10—C9	102.8 (3)
C4—C3—C2	105.0 (4)	N2—C10—H10A	111.2
C4—C3—H3A	110.8	C9—C10—H10A	111.2
C2—C3—H3A	110.8	N2—C10—H10B	111.2
C4—C3—H3B	110.8	C9—C10—H10B	111.2
C2—C3—H3B	110.8	H10A—C10—H10B	109.1
H3A—C3—H3B	108.8

Symmetry code: (i) −x+1, −y+1, −z+1.