Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030995/cv6419sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030995/cv6419Isup2.hkl |
CCDC reference: 262426
Data collection: CAD-4 Diffractometer Control Software (Enraf–Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: CAD-4 Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C13H17BrO | Dx = 1.462 Mg m−3 |
Mr = 269.18 | Melting point: 337 K |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.269 (2) Å | Cell parameters from 25 reflections |
b = 16.085 (2) Å | θ = 10–15° |
c = 5.7278 (4) Å | µ = 3.34 mm−1 |
V = 1222.5 (3) Å3 | T = 173 K |
Z = 4 | Block, colourless |
F(000) = 552 | 0.30 × 0.20 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | 1360 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 22.5°, θmin = 3.1° |
ω/2θ scans | h = −14→8 |
Absorption correction: empirical from ψ scan (North et al., 1968) | k = 0→17 |
Tmin = 0.402, Tmax = 0.513 | l = −6→6 |
2915 measured reflections | 3 standard reflections every 100 reflections |
1598 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.073 | w = 1/[σ2(Fo2) + (0.0348P)2 + 0.2533P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
1598 reflections | Δρmax = 0.39 e Å−3 |
146 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 628 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.009 (19) |
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. |
x | y | z | Uiso*/Ueq | ||
C2 | 0.0188 (3) | 0.1919 (3) | 0.1890 (8) | 0.0314 (12) | |
C3 | 0.0766 (3) | 0.2727 (3) | 0.2293 (9) | 0.0365 (13) | |
H3 | 0.118 (3) | 0.281 (2) | 0.080 (8) | 0.030 (12)* | |
C4 | 0.0119 (4) | 0.3481 (3) | 0.2745 (8) | 0.0304 (12) | |
H4A | 0.0548 | 0.3980 | 0.2937 | 0.037* | |
H4B | −0.0277 | 0.3402 | 0.4193 | 0.037* | |
C5 | −0.0595 (4) | 0.3594 (3) | 0.0641 (9) | 0.0360 (14) | |
H5 | −0.014 (3) | 0.374 (2) | −0.081 (8) | 0.026 (12)* | |
C6 | −0.1159 (3) | 0.2776 (2) | 0.0271 (11) | 0.0384 (12) | |
H6A | −0.1582 | 0.2657 | 0.1656 | 0.046* | |
H6B | −0.1611 | 0.2829 | −0.1098 | 0.046* | |
C7 | −0.0418 (4) | 0.1617 (3) | 0.3955 (10) | 0.0478 (14) | |
H7A | −0.0760 | 0.2090 | 0.4691 | 0.072* | |
H7B | 0.0033 | 0.1353 | 0.5090 | 0.072* | |
H7C | −0.0921 | 0.1213 | 0.3425 | 0.072* | |
C8 | 0.0859 (4) | 0.1246 (3) | 0.0938 (10) | 0.0488 (15) | |
H8A | 0.0453 | 0.0753 | 0.0579 | 0.073* | |
H8B | 0.1371 | 0.1102 | 0.2102 | 0.073* | |
H8C | 0.1189 | 0.1443 | −0.0489 | 0.073* | |
C9 | −0.1333 (4) | 0.4298 (3) | 0.0936 (9) | 0.0348 (13) | |
C10 | −0.1450 (4) | 0.4883 (4) | −0.0862 (9) | 0.0421 (14) | |
H10 | −0.1042 | 0.4849 | −0.2221 | 0.051* | |
C11 | −0.2169 (5) | 0.5520 (3) | −0.0657 (10) | 0.0484 (16) | |
H11 | −0.2250 | 0.5913 | −0.1881 | 0.058* | |
C12 | −0.2758 (5) | 0.5575 (4) | 0.1322 (12) | 0.0500 (16) | |
H12 | −0.3248 | 0.6003 | 0.1463 | 0.060* | |
C13 | −0.2633 (4) | 0.5009 (3) | 0.3079 (10) | 0.0465 (14) | |
H13 | −0.3037 | 0.5048 | 0.4444 | 0.056* | |
C14 | −0.1935 (4) | 0.4391 (3) | 0.2894 (9) | 0.0391 (13) | |
H14 | −0.1858 | 0.4011 | 0.4152 | 0.047* | |
O1 | −0.0479 (2) | 0.21043 (16) | −0.0097 (7) | 0.0392 (8) | |
Br1 | 0.17155 (3) | 0.25918 (2) | 0.49307 (11) | 0.04250 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.026 (3) | 0.031 (2) | 0.038 (3) | 0.001 (2) | −0.006 (2) | 0.000 (2) |
C3 | 0.028 (3) | 0.049 (3) | 0.032 (3) | 0.000 (3) | −0.003 (2) | 0.001 (3) |
C4 | 0.034 (3) | 0.026 (2) | 0.032 (3) | −0.004 (2) | −0.006 (2) | −0.002 (2) |
C5 | 0.037 (3) | 0.039 (3) | 0.031 (4) | −0.002 (2) | −0.002 (2) | 0.001 (2) |
C6 | 0.034 (2) | 0.039 (2) | 0.043 (3) | 0.003 (2) | −0.013 (3) | −0.011 (3) |
C7 | 0.049 (4) | 0.051 (3) | 0.043 (3) | −0.008 (3) | 0.007 (3) | 0.000 (3) |
C8 | 0.045 (4) | 0.050 (3) | 0.052 (4) | 0.001 (3) | 0.004 (3) | −0.006 (3) |
C9 | 0.032 (3) | 0.031 (3) | 0.041 (3) | −0.002 (2) | −0.013 (2) | −0.003 (2) |
C10 | 0.035 (3) | 0.053 (3) | 0.038 (3) | −0.016 (3) | −0.007 (2) | −0.001 (3) |
C11 | 0.055 (4) | 0.036 (3) | 0.054 (4) | −0.007 (3) | −0.031 (3) | 0.013 (3) |
C12 | 0.044 (4) | 0.039 (3) | 0.066 (4) | 0.004 (3) | −0.018 (3) | −0.009 (3) |
C13 | 0.043 (4) | 0.045 (3) | 0.052 (4) | 0.005 (3) | −0.003 (3) | −0.008 (3) |
C14 | 0.040 (3) | 0.038 (3) | 0.039 (3) | −0.001 (3) | −0.004 (3) | −0.003 (2) |
O1 | 0.0404 (17) | 0.0384 (15) | 0.0388 (19) | 0.0024 (14) | 0.000 (2) | −0.009 (2) |
Br1 | 0.0336 (3) | 0.0498 (3) | 0.0440 (3) | 0.0010 (2) | −0.0124 (3) | 0.0018 (4) |
C2—O1 | 1.472 (6) | C7—H7B | 0.9800 |
C2—C8 | 1.504 (6) | C7—H7C | 0.9800 |
C2—C7 | 1.511 (7) | C8—H8A | 0.9800 |
C2—C3 | 1.527 (7) | C8—H8B | 0.9800 |
C3—C4 | 1.508 (7) | C8—H8C | 0.9800 |
C3—Br1 | 1.979 (5) | C9—C14 | 1.385 (7) |
C3—H3 | 1.03 (4) | C9—C10 | 1.404 (7) |
C4—C5 | 1.544 (6) | C10—C11 | 1.404 (8) |
C4—H4A | 0.9900 | C10—H10 | 0.9500 |
C4—H4B | 0.9900 | C11—C12 | 1.380 (8) |
C5—C9 | 1.505 (7) | C11—H11 | 0.9500 |
C5—C6 | 1.529 (7) | C12—C13 | 1.367 (8) |
C5—H5 | 1.06 (4) | C12—H12 | 0.9500 |
C6—O1 | 1.424 (5) | C13—C14 | 1.364 (7) |
C6—H6A | 0.9900 | C13—H13 | 0.9500 |
C6—H6B | 0.9900 | C14—H14 | 0.9500 |
C7—H7A | 0.9800 | ||
O1—C2—C8 | 102.8 (4) | C2—C7—H7B | 109.5 |
O1—C2—C7 | 110.5 (4) | H7A—C7—H7B | 109.5 |
C8—C2—C7 | 111.5 (4) | C2—C7—H7C | 109.5 |
O1—C2—C3 | 104.3 (3) | H7A—C7—H7C | 109.5 |
C8—C2—C3 | 111.8 (4) | H7B—C7—H7C | 109.5 |
C7—C2—C3 | 115.0 (4) | C2—C8—H8A | 109.5 |
C4—C3—C2 | 115.1 (4) | C2—C8—H8B | 109.5 |
C4—C3—Br1 | 108.7 (3) | H8A—C8—H8B | 109.5 |
C2—C3—Br1 | 110.0 (3) | C2—C8—H8C | 109.5 |
C4—C3—H3 | 111 (2) | H8A—C8—H8C | 109.5 |
C2—C3—H3 | 105 (2) | H8B—C8—H8C | 109.5 |
Br1—C3—H3 | 108 (2) | C14—C9—C10 | 117.2 (5) |
C3—C4—C5 | 108.1 (4) | C14—C9—C5 | 123.2 (5) |
C3—C4—H4A | 110.1 | C10—C9—C5 | 119.6 (5) |
C5—C4—H4A | 110.1 | C11—C10—C9 | 120.2 (5) |
C3—C4—H4B | 110.1 | C11—C10—H10 | 119.9 |
C5—C4—H4B | 110.1 | C9—C10—H10 | 119.9 |
H4A—C4—H4B | 108.4 | C12—C11—C10 | 120.0 (5) |
C9—C5—C6 | 110.1 (4) | C12—C11—H11 | 120.0 |
C9—C5—C4 | 113.6 (4) | C10—C11—H11 | 120.0 |
C6—C5—C4 | 107.9 (4) | C13—C12—C11 | 119.5 (5) |
C9—C5—H5 | 107 (2) | C13—C12—H12 | 120.2 |
C6—C5—H5 | 111 (2) | C11—C12—H12 | 120.2 |
C4—C5—H5 | 107 (2) | C14—C13—C12 | 120.7 (6) |
O1—C6—C5 | 111.3 (4) | C14—C13—H13 | 119.6 |
O1—C6—H6A | 109.4 | C12—C13—H13 | 119.6 |
C5—C6—H6A | 109.4 | C13—C14—C9 | 122.3 (5) |
O1—C6—H6B | 109.4 | C13—C14—H14 | 118.9 |
C5—C6—H6B | 109.4 | C9—C14—H14 | 118.9 |
H6A—C6—H6B | 108.0 | C6—O1—C2 | 114.9 (4) |
C2—C7—H7A | 109.5 | ||
O1—C2—C3—C4 | 57.1 (5) | C6—C5—C9—C10 | −107.9 (5) |
C8—C2—C3—C4 | 167.4 (4) | C4—C5—C9—C10 | 130.9 (5) |
C7—C2—C3—C4 | −64.1 (6) | C14—C9—C10—C11 | −1.3 (7) |
O1—C2—C3—Br1 | −179.8 (3) | C5—C9—C10—C11 | 177.0 (5) |
C8—C2—C3—Br1 | −69.5 (5) | C9—C10—C11—C12 | 0.4 (7) |
C7—C2—C3—Br1 | 59.0 (5) | C10—C11—C12—C13 | 0.3 (8) |
C2—C3—C4—C5 | −57.9 (5) | C11—C12—C13—C14 | −0.2 (8) |
Br1—C3—C4—C5 | 178.3 (3) | C12—C13—C14—C9 | −0.8 (8) |
C3—C4—C5—C9 | 176.4 (4) | C10—C9—C14—C13 | 1.5 (7) |
C3—C4—C5—C6 | 54.0 (5) | C5—C9—C14—C13 | −176.7 (5) |
C9—C5—C6—O1 | 177.9 (5) | C5—C6—O1—C2 | 63.3 (5) |
C4—C5—C6—O1 | −57.6 (6) | C8—C2—O1—C6 | −175.7 (4) |
C6—C5—C9—C14 | 70.3 (6) | C7—C2—O1—C6 | 65.2 (5) |
C4—C5—C9—C14 | −50.8 (6) | C3—C2—O1—C6 | −59.0 (5) |