Bromo­(dithio­benzoato-κ²S,S′)tris­(tetra­hydro­furan-κO)magnesium(II): a redetermination

The crystal structure of the title compound, [MgBr(C₆H₅CS₂)(C₄H₈O)₃], has been reported previously by Chang, Yang, Guo, Huang, Wang, Lee & Peng [J. Chin. Chem. Soc. (Taipei) (2003), 50, 965–971] using intensity data collected at room temperature. However, no coordinates are available. We present here a redetermination of this structure using new intensity data collected at 120 K. The Mg^II atom is six-coordinate in an octa­hedral geometry.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.070
• wR factor = 0.181
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.110
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bromo(dithiobenzoato-κ²S,S')tris(tetrahydrofuran-κO)magnesium(II)

Crystal data

[MgBr(C7H5S2)(C4H8O)3]	F(000) = 984
Mr = 473.76	Dx = 1.427 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4135 reflections
a = 11.901 (4) Å	θ = 2.7–32.6°
b = 14.720 (3) Å	µ = 2.10 mm^−1
c = 13.0391 (17) Å	T = 120 K
β = 105.154 (18)°	Plate, red
V = 2204.8 (9) Å^3	0.38 × 0.22 × 0.06 mm
Z = 4

Data collection

4-axis κ geometry diffractometer	3418 reflections with I > 2σ(I)
ω scans	Rint = 0.110
Absorption correction: numerical (CrysAlis RED; Oxford Diffraction, 2005)	θmax = 25.1°, θmin = 3.0°
Tmin = 0.432, Tmax = 0.796	h = −9→14
14329 measured reflections	k = −17→17
3932 independent reflections	l = −15→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.070	w = 1/[σ^2(Fo^2) + (0.0913P)^2 + 8.1437P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.181	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 1.08 e Å^−3
3932 reflections	Δρmin = −0.69 e Å^−3
235 parameters

Special details

Experimental. ¹H NMR. (500 MHz, CDCl₃, 298 K) ABB'CC' spin system. 7.35 p.p.m. (pst. 7.7 Hz, m - H), 7.50 p.p.m. (pst. 7.3 Hz, p - H), 8.50 p.p.m. (psd. 7.8 Hz, o - H), 4.03 p.p.m. (m, THF) and 1.93 p.p.m. (m, THF).

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	0.4846 (5)	0.3471 (3)	0.2665 (4)	0.0176 (11)
C2	0.3639 (5)	0.3401 (3)	0.1922 (5)	0.0209 (12)
C3	0.2653 (5)	0.3439 (4)	0.2325 (6)	0.0303 (14)
H22	0.2746	0.3531	0.3064	0.036*
C4	0.1538 (6)	0.3341 (5)	0.1644 (6)	0.0380 (17)
H23	0.0877	0.3353	0.1924	0.046*
C5	0.1392 (6)	0.3225 (5)	0.0559 (6)	0.0373 (16)
H24	0.0633	0.3167	0.0097	0.045*
C6	0.2356 (5)	0.3196 (4)	0.0156 (5)	0.0313 (14)
H25	0.2258	0.3113	−0.0585	0.038*
C7	0.3469 (5)	0.3287 (4)	0.0831 (5)	0.0246 (13)
H26	0.4124	0.3271	0.0542	0.03*
C8	0.7210 (5)	0.4002 (4)	0.6363 (5)	0.0245 (12)
H27A	0.6766	0.3427	0.6292	0.029*
H27B	0.6657	0.4517	0.6268	0.029*
C9	0.8113 (6)	0.4056 (4)	0.7465 (5)	0.0306 (14)
H28A	0.7918	0.4554	0.7898	0.037*
H28B	0.8142	0.3477	0.7857	0.037*
C10	0.9270 (6)	0.4239 (5)	0.7205 (5)	0.0372 (16)
H29A	0.9723	0.4707	0.7685	0.045*
H29B	0.9741	0.3678	0.727	0.045*
C11	0.8925 (5)	0.4573 (4)	0.6068 (5)	0.0295 (14)
H30A	0.8752	0.5232	0.6034	0.035*
H30B	0.9546	0.4452	0.5708	0.035*
C12	0.8244 (5)	0.1981 (4)	0.5548 (5)	0.0233 (12)
H31A	0.8055	0.2082	0.6235	0.028*
H31B	0.8994	0.228	0.557	0.028*
C13	0.8298 (5)	0.0994 (4)	0.5325 (5)	0.0272 (13)
H32A	0.8649	0.0649	0.5982	0.033*
H32B	0.875	0.0879	0.48	0.033*
C14	0.7013 (5)	0.0743 (4)	0.4874 (5)	0.0258 (13)
H33A	0.6926	0.0238	0.4358	0.031*
H33B	0.6654	0.0564	0.5449	0.031*
C15	0.6463 (5)	0.1614 (4)	0.4329 (5)	0.0257 (13)
H34A	0.6267	0.1546	0.3547	0.031*
H34B	0.5742	0.176	0.454	0.031*
C16	0.6672 (5)	0.5694 (4)	0.4067 (5)	0.0258 (13)
H35A	0.7155	0.6221	0.4386	0.031*
H35B	0.6314	0.5427	0.4603	0.031*
C17	0.5744 (5)	0.5976 (4)	0.3077 (5)	0.0298 (14)
H36A	0.5462	0.6599	0.3149	0.036*
H36B	0.5076	0.5552	0.2929	0.036*
C18	0.6393 (6)	0.5928 (4)	0.2208 (5)	0.0308 (14)
H37A	0.5933	0.5592	0.1581	0.037*
H37B	0.656	0.6545	0.1983	0.037*
C19	0.7519 (5)	0.5425 (4)	0.2730 (5)	0.0289 (13)
H38A	0.767	0.4943	0.2253	0.035*
H38B	0.8187	0.585	0.2893	0.035*
Br1	0.92940 (5)	0.33681 (4)	0.35960 (4)	0.0215 (2)
Mg1	0.73406 (15)	0.36313 (12)	0.40342 (14)	0.0175 (4)
O1	0.7887 (3)	0.4045 (3)	0.5596 (3)	0.0220 (8)
O2	0.7330 (3)	0.2324 (3)	0.4678 (3)	0.0225 (8)
O3	0.7353 (3)	0.5034 (3)	0.3695 (3)	0.0217 (8)
S1	0.60115 (12)	0.32821 (9)	0.21733 (11)	0.0201 (3)
S2	0.50381 (12)	0.37192 (10)	0.39607 (11)	0.0230 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.025 (3)	0.011 (2)	0.019 (3)	0.000 (2)	0.011 (2)	−0.001 (2)
C2	0.022 (3)	0.014 (3)	0.029 (3)	−0.001 (2)	0.010 (2)	−0.003 (2)
C3	0.026 (3)	0.030 (3)	0.038 (4)	0.000 (2)	0.013 (3)	−0.003 (3)
C4	0.023 (3)	0.043 (4)	0.048 (4)	−0.005 (3)	0.009 (3)	−0.008 (3)
C5	0.021 (3)	0.039 (4)	0.048 (4)	0.002 (3)	0.001 (3)	−0.008 (3)
C6	0.028 (3)	0.038 (4)	0.029 (3)	−0.004 (3)	0.009 (3)	−0.004 (3)
C7	0.029 (3)	0.021 (3)	0.024 (3)	0.003 (2)	0.007 (3)	0.000 (2)
C8	0.039 (3)	0.019 (3)	0.021 (3)	−0.005 (2)	0.019 (3)	0.000 (2)
C9	0.045 (4)	0.032 (3)	0.018 (3)	0.002 (3)	0.014 (3)	0.000 (3)
C10	0.039 (4)	0.048 (4)	0.021 (3)	−0.012 (3)	0.001 (3)	−0.012 (3)
C11	0.030 (3)	0.034 (3)	0.026 (3)	−0.015 (3)	0.009 (3)	−0.006 (3)
C12	0.022 (3)	0.024 (3)	0.021 (3)	0.002 (2)	0.000 (2)	0.004 (2)
C13	0.035 (3)	0.025 (3)	0.021 (3)	0.006 (3)	0.007 (3)	0.006 (2)
C14	0.038 (3)	0.016 (3)	0.024 (3)	−0.004 (2)	0.010 (3)	0.001 (2)
C15	0.028 (3)	0.022 (3)	0.024 (3)	−0.007 (2)	0.002 (3)	0.001 (2)
C16	0.042 (3)	0.015 (3)	0.025 (3)	0.004 (2)	0.017 (3)	−0.004 (2)
C17	0.036 (3)	0.022 (3)	0.035 (4)	0.004 (2)	0.015 (3)	0.007 (3)
C18	0.039 (3)	0.024 (3)	0.032 (3)	0.008 (3)	0.014 (3)	0.007 (3)
C19	0.037 (3)	0.026 (3)	0.027 (3)	0.004 (3)	0.014 (3)	0.006 (3)
Br1	0.0224 (3)	0.0219 (3)	0.0219 (3)	0.0003 (2)	0.0086 (2)	−0.0009 (2)
Mg1	0.0211 (9)	0.0151 (9)	0.0169 (9)	0.0004 (7)	0.0062 (7)	−0.0003 (7)
O1	0.028 (2)	0.021 (2)	0.019 (2)	−0.0064 (16)	0.0099 (17)	−0.0059 (16)
O2	0.023 (2)	0.0196 (19)	0.023 (2)	−0.0024 (16)	0.0018 (16)	0.0042 (16)
O3	0.030 (2)	0.0179 (19)	0.0190 (19)	0.0026 (16)	0.0091 (17)	0.0006 (16)
S1	0.0203 (7)	0.0229 (7)	0.0182 (7)	−0.0013 (5)	0.0069 (6)	−0.0021 (5)
S2	0.0248 (7)	0.0260 (7)	0.0195 (7)	0.0020 (6)	0.0079 (6)	−0.0014 (6)

Geometric parameters (Å, º)

C1—C2	1.512 (8)	C12—H31B	0.99
C1—S2	1.685 (6)	C13—C14	1.533 (9)
C1—S1	1.697 (5)	C13—H32A	0.99
C2—C7	1.394 (9)	C13—H32B	0.99
C2—C3	1.407 (8)	C14—C15	1.528 (8)
C3—C4	1.398 (9)	C14—H33A	0.99
C3—H22	0.95	C14—H33B	0.99
C4—C5	1.390 (11)	C15—O2	1.456 (7)
C4—H23	0.95	C15—H34A	0.99
C5—C6	1.382 (9)	C15—H34B	0.99
C5—H24	0.95	C16—O3	1.428 (7)
C6—C7	1.392 (9)	C16—C17	1.520 (9)
C6—H25	0.95	C16—H35A	0.99
C7—H26	0.95	C16—H35B	0.99
C8—O1	1.440 (6)	C17—C18	1.531 (8)
C8—C9	1.555 (8)	C17—H36A	0.99
C8—H27A	0.99	C17—H36B	0.99
C8—H27B	0.99	C18—C19	1.527 (8)
C9—C10	1.526 (9)	C18—H37A	0.99
C9—H28A	0.99	C18—H37B	0.99
C9—H28B	0.99	C19—O3	1.444 (7)
C10—C11	1.513 (9)	C19—H38A	0.99
C10—H29A	0.99	C19—H38B	0.99
C10—H29B	0.99	Br1—Mg1	2.5644 (19)
C11—O1	1.454 (7)	Mg1—O1	2.061 (4)
C11—H30A	0.99	Mg1—O2	2.100 (4)
C11—H30B	0.99	Mg1—O3	2.113 (4)
C12—O2	1.443 (6)	Mg1—S1	2.578 (2)
C12—C13	1.487 (8)	Mg1—S2	2.720 (2)
C12—H31A	0.99
C2—C1—S2	121.0 (4)	C15—C14—H33B	111
C2—C1—S1	118.7 (4)	C13—C14—H33B	111
S2—C1—S1	120.3 (3)	H33A—C14—H33B	109
C7—C2—C3	118.3 (6)	O2—C15—C14	106.0 (5)
C7—C2—C1	121.5 (5)	O2—C15—H34A	110.5
C3—C2—C1	120.2 (5)	C14—C15—H34A	110.5
C4—C3—C2	120.3 (6)	O2—C15—H34B	110.5
C4—C3—H22	119.9	C14—C15—H34B	110.5
C2—C3—H22	119.9	H34A—C15—H34B	108.7
C5—C4—C3	120.3 (6)	O3—C16—C17	104.4 (5)
C5—C4—H23	119.9	O3—C16—H35A	110.9
C3—C4—H23	119.9	C17—C16—H35A	110.9
C6—C5—C4	119.8 (6)	O3—C16—H35B	110.9
C6—C5—H24	120.1	C17—C16—H35B	110.9
C4—C5—H24	120.1	H35A—C16—H35B	108.9
C5—C6—C7	120.3 (6)	C16—C17—C18	102.7 (5)
C5—C6—H25	119.9	C16—C17—H36A	111.2
C7—C6—H25	119.9	C18—C17—H36A	111.2
C6—C7—C2	121.1 (6)	C16—C17—H36B	111.2
C6—C7—H26	119.4	C18—C17—H36B	111.2
C2—C7—H26	119.4	H36A—C17—H36B	109.1
O1—C8—C9	105.2 (4)	C19—C18—C17	104.3 (5)
O1—C8—H27A	110.7	C19—C18—H37A	110.9
C9—C8—H27A	110.7	C17—C18—H37A	110.9
O1—C8—H27B	110.7	C19—C18—H37B	110.9
C9—C8—H27B	110.7	C17—C18—H37B	110.9
H27A—C8—H27B	108.8	H37A—C18—H37B	108.9
C10—C9—C8	104.5 (5)	O3—C19—C18	106.1 (5)
C10—C9—H28A	110.9	O3—C19—H38A	110.5
C8—C9—H28A	110.9	C18—C19—H38A	110.5
C10—C9—H28B	110.9	O3—C19—H38B	110.5
C8—C9—H28B	110.9	C18—C19—H38B	110.5
H28A—C9—H28B	108.9	H38A—C19—H38B	108.7
C11—C10—C9	104.2 (5)	O1—Mg1—O2	84.77 (16)
C11—C10—H29A	110.9	O1—Mg1—O3	84.28 (16)
C9—C10—H29A	110.9	O2—Mg1—O3	168.51 (17)
C11—C10—H29B	110.9	O1—Mg1—Br1	101.23 (13)
C9—C10—H29B	110.9	O2—Mg1—Br1	92.95 (12)
H29A—C10—H29B	108.9	O3—Mg1—Br1	92.57 (12)
O1—C11—C10	103.0 (5)	O1—Mg1—S1	161.11 (14)
O1—C11—H30A	111.2	O2—Mg1—S1	97.31 (13)
C10—C11—H30A	111.2	O3—Mg1—S1	91.96 (13)
O1—C11—H30B	111.2	Br1—Mg1—S1	97.42 (7)
C10—C11—H30B	111.2	O1—Mg1—S2	94.32 (13)
H30A—C11—H30B	109.1	O2—Mg1—S2	86.91 (12)
O2—C12—C13	104.5 (4)	O3—Mg1—S2	90.46 (12)
O2—C12—H31A	110.8	Br1—Mg1—S2	164.38 (8)
C13—C12—H31A	110.8	S1—Mg1—S2	67.15 (6)
O2—C12—H31B	110.8	C8—O1—C11	107.3 (4)
C13—C12—H31B	110.8	C8—O1—Mg1	125.8 (3)
H31A—C12—H31B	108.9	C11—O1—Mg1	126.1 (3)
C12—C13—C14	102.8 (5)	C12—O2—C15	108.7 (4)
C12—C13—H32A	111.2	C12—O2—Mg1	123.6 (3)
C14—C13—H32A	111.2	C15—O2—Mg1	127.7 (3)
C12—C13—H32B	111.2	C16—O3—C19	104.1 (4)
C14—C13—H32B	111.2	C16—O3—Mg1	124.0 (3)
H32A—C13—H32B	109.1	C19—O3—Mg1	125.6 (3)
C15—C14—C13	103.8 (5)	C1—S1—Mg1	88.4 (2)
C15—C14—H33A	111	C1—S2—Mg1	84.1 (2)
C13—C14—H33A	111