Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030431/ci2116sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030431/ci2116Isup2.hkl |
CCDC reference: 620741
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (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
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).
[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) Å3 | 0.38 × 0.22 × 0.06 mm |
Z = 4 |
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 on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.070 | w = 1/[σ2(Fo2) + (0.0913P)2 + 8.1437P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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 |