[2,2-Bis­(chloro­methyl)­propyl­ene]­bis­(di­phenyl­stibine)

The title compound, [Sb₂(C₆H₅)₄(C₅H₈Cl₂)], is the product of a substitution reaction of 2,2-bis­(chloro­methyl)-1,3-di­chloro­propane with sodium di­phenyl­stibide. Adjacent phenyl groups embrace each other in a parallel fashion in order to minimize interaction. The mol­ecule has crystallographic twofold rotation symmetry.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.025
• wR factor = 0.063
• Data-to-parameter ratio = 18.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



ABSTY_01  Extra text has been found in the _exptl_absorpt_correction_type
          field, which should be only a single keyword. A literature
          citation should be included in the _exptl_absorpt_process_details
          field.

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Computing details

Cell refinement: DENZO (Hooft, 1998) and COLLECT (Otwinowski & Minor, 1997); data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

(I)

Crystal data

[Sb2(C6H5)4(C5H8Cl2)]	F(000) = 1352
Mr = 690.91	Dx = 1.702 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.578 (3) Å	Cell parameters from 6922 reflections
b = 12.009 (2) Å	θ = 2.9–26.4°
c = 15.849 (3) Å	µ = 2.22 mm^−1
β = 103.67 (3)°	T = 150 K
V = 2696.2 (9) Å^3	Needle, colourless
Z = 4	0.22 × 0.08 × 0.06 mm

Data collection

Nonius KappaCCD area-detector diffractometer	2458 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.058
Absorption correction: multi-scans (SORTAV; Blessing, 1997)	θmax = 26.4°, θmin = 3.2°
Tmin = 0.641, Tmax = 0.878	h = −18→17
9556 measured reflections	k = −14→14
2739 independent reflections	l = −18→19

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0253P)^2 + 1.756P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.026	(Δ/σ)max = 0.001
wR(F^2) = 0.063	Δρmax = 0.77 e Å^−3
S = 1.07	Δρmin = −0.70 e Å^−3
2739 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
151 parameters	Extinction coefficient: 0.00078 (11)
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
C1	0.19743 (18)	0.9803 (2)	0.09451 (16)	0.0229 (5)
C2	0.24796 (18)	0.8963 (2)	0.06461 (18)	0.0285 (6)
H2	0.2556	0.8263	0.0933	0.034*
C3	0.28708 (19)	0.9129 (2)	−0.00580 (19)	0.0329 (6)
H3	0.3217	0.8549	−0.0247	0.039*
C4	0.27586 (19)	1.0136 (3)	−0.04866 (19)	0.0323 (6)
H4	0.3029	1.0253	−0.0969	0.039*
C5	0.22453 (19)	1.0983 (2)	−0.02071 (18)	0.0322 (6)
H5	0.2151	1.1673	−0.0508	0.039*
C6	0.18742 (19)	1.0814 (2)	0.05103 (18)	0.0297 (6)
H6	0.1544	1.1403	0.0709	0.036*
C7	0.08813 (18)	0.7910 (2)	0.16749 (17)	0.0265 (6)
C8	0.02188 (19)	0.7794 (2)	0.08824 (18)	0.0340 (6)
H8	0.0029	0.8427	0.0525	0.041*
C9	−0.0162 (2)	0.6758 (2)	0.0616 (2)	0.0424 (8)
H9	−0.0616	0.6687	0.0079	0.051*
C10	0.0114 (2)	0.5832 (3)	0.1127 (2)	0.0448 (8)
H10	−0.0149	0.5124	0.0944	0.054*
C11	0.0774 (2)	0.5938 (2)	0.1907 (2)	0.0429 (8)
H11	0.0969	0.53	0.2258	0.052*
C12	0.11514 (19)	0.6970 (2)	0.21784 (19)	0.0316 (6)
H12	0.1602	0.7036	0.2718	0.038*
C13	0.01975 (18)	1.04800 (18)	0.17578 (17)	0.0199 (5)
H13A	0.0232	1.0971	0.1265	0.024*
H13B	−0.0342	0.9967	0.1557	0.024*
C14	0	1.1206 (3)	0.25	0.0190 (7)
C15	0.08448 (17)	1.1935 (2)	0.29216 (16)	0.0239 (5)
H15A	0.1375	1.1449	0.321	0.029*
H15B	0.0672	1.2402	0.3374	0.029*
Sb1	0.149395 (11)	0.949625 (13)	0.210673 (10)	0.02181 (10)
Cl1	0.12339 (5)	1.28256 (6)	0.21571 (5)	0.03507 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0176 (12)	0.0260 (13)	0.0250 (13)	−0.0020 (10)	0.0049 (10)	−0.0041 (11)
C2	0.0244 (13)	0.0252 (14)	0.0365 (15)	0.0044 (11)	0.0081 (12)	−0.0011 (12)
C3	0.0263 (15)	0.0337 (15)	0.0392 (16)	0.0041 (12)	0.0090 (13)	−0.0098 (13)
C4	0.0252 (15)	0.0411 (16)	0.0320 (15)	−0.0011 (13)	0.0092 (12)	−0.0037 (13)
C5	0.0308 (15)	0.0310 (15)	0.0366 (15)	0.0002 (12)	0.0114 (13)	0.0044 (12)
C6	0.0285 (15)	0.0231 (13)	0.0385 (16)	0.0020 (11)	0.0100 (13)	−0.0011 (12)
C7	0.0241 (13)	0.0200 (13)	0.0390 (15)	0.0018 (10)	0.0147 (12)	−0.0002 (11)
C8	0.0304 (15)	0.0283 (15)	0.0423 (16)	0.0011 (12)	0.0069 (13)	−0.0041 (12)
C9	0.0301 (16)	0.0377 (18)	0.058 (2)	−0.0054 (13)	0.0078 (14)	−0.0160 (15)
C10	0.0407 (18)	0.0274 (16)	0.075 (2)	−0.0087 (14)	0.0311 (18)	−0.0164 (17)
C11	0.052 (2)	0.0192 (14)	0.070 (2)	0.0084 (14)	0.0386 (18)	0.0093 (15)
C12	0.0300 (15)	0.0239 (14)	0.0449 (17)	0.0034 (12)	0.0170 (13)	0.0023 (12)
C13	0.0146 (12)	0.0185 (13)	0.0256 (13)	−0.0002 (9)	0.0026 (11)	−0.0014 (9)
C14	0.0157 (16)	0.0149 (16)	0.0265 (18)	0	0.0050 (14)	0
C15	0.0221 (12)	0.0193 (12)	0.0317 (14)	−0.0017 (10)	0.0089 (11)	0.0001 (10)
Sb1	0.01911 (13)	0.01996 (13)	0.02567 (14)	0.00323 (6)	0.00394 (9)	−0.00063 (6)
Cl1	0.0350 (4)	0.0252 (4)	0.0477 (4)	−0.0108 (3)	0.0151 (3)	0.0010 (3)

Geometric parameters (Å, º)

C1—C6	1.386 (4)	C8—C9	1.386 (4)
C1—C2	1.396 (4)	C9—C10	1.379 (5)
C1—Sb1	2.151 (3)	C10—C11	1.381 (5)
C2—C3	1.383 (4)	C11—C12	1.383 (4)
C3—C4	1.378 (4)	C13—C14	1.545 (3)
C4—C5	1.395 (4)	C13—Sb1	2.186 (2)
C5—C6	1.385 (4)	C14—C15	1.530 (3)
C7—C12	1.384 (4)	C14—C15^i	1.530 (3)
C7—C8	1.399 (4)	C14—C13^i	1.545 (3)
C7—Sb1	2.146 (3)	C15—Cl1	1.805 (2)
C6—C1—C2	117.8 (2)	C10—C11—C12	120.2 (3)
C6—C1—Sb1	123.94 (19)	C11—C12—C7	120.9 (3)
C2—C1—Sb1	118.1 (2)	C14—C13—Sb1	114.70 (15)
C3—C2—C1	121.4 (3)	C15—C14—C15^i	110.2 (3)
C4—C3—C2	120.1 (3)	C15—C14—C13^i	105.43 (13)
C3—C4—C5	119.5 (3)	C15^i—C14—C13^i	112.31 (13)
C6—C5—C4	119.8 (3)	C15—C14—C13	112.31 (13)
C5—C6—C1	121.4 (3)	C15^i—C14—C13	105.43 (13)
C12—C7—C8	118.6 (2)	C13^i—C14—C13	111.3 (3)
C12—C7—Sb1	120.0 (2)	C14—C15—Cl1	113.22 (15)
C8—C7—Sb1	121.45 (19)	C7—Sb1—C1	94.27 (10)
C9—C8—C7	120.3 (3)	C7—Sb1—C13	97.43 (9)
C10—C9—C8	120.3 (3)	C1—Sb1—C13	97.34 (10)
C9—C10—C11	119.7 (3)

Symmetry code: (i) −x, y, −z+1/2.