Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031606/ez2019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031606/ez2019Isup2.hkl |
CCDC reference: 620960
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- R factor = 0.038
- wR factor = 0.096
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C7
Alert level C ABSTM02_ALERT_3_C The ratio of Tmax/Tmin expected RT(exp) is > 1.10 Absorption corrections should be applied. Tmin and Tmax expected: 0.459 0.525 RT(exp) = 1.146 PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.16 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.68 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 5.72 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT410_ALERT_2_C Short Intra H...H Contact H12B .. H18B .. 1.91 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.51 From the CIF: _reflns_number_total 3480 Count of symmetry unique reflns 2040 Completeness (_total/calc) 170.59% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1440 Fraction of Friedel pairs measured 0.706 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C18H25BrO | F(000) = 352 |
Mr = 337.29 | Dx = 1.352 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1721 (3) Å | Cell parameters from 1962 reflections |
b = 7.9624 (3) Å | θ = 2.6–23.6° |
c = 14.5849 (6) Å | µ = 2.48 mm−1 |
β = 95.719 (2)° | T = 294 K |
V = 828.76 (6) Å3 | Block, colorless |
Z = 2 | 0.43 × 0.27 × 0.26 mm |
Bruker APEX CCD area-detector diffractometer | 2336 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 27.5°, θmin = 2.8° |
φ and ω scans | h = −7→9 |
5095 measured reflections | k = −10→10 |
3480 independent reflections | l = −18→18 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0411P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.096 | (Δ/σ)max < 0.001 |
S = 0.97 | Δρmax = 0.32 e Å−3 |
3480 reflections | Δρmin = −0.37 e Å−3 |
185 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
7 restraints | Extinction coefficient: 0.060 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.030 (12) |
Experimental. [α]D20 -33 (c 1.7, CHCl3); IR (film): 3006, 2956, 2874, 1605, 1455, 1384, 1312, 1250, 1120, 1081, 734, 696 cm-1; 1H NMR (300 MHz, CDCl3): δ 7.33 (d, 4H, J = 4.2 Hz), 7.28–7.24 (m, 1H), 4.45 (d, 2H, J = 3.0 Hz), 3.78 (d, 1H, J = 9.9 Hz), 3.21 (d, 1H, J = 9.9 Hz), 2.62–2.55 (m, 1H), 2.03 (t, 1H, J = 4.5 Hz), 1.82–1.74 (m, 2H), 1.65–1.53 (m, 1H), 1.40 (s, 3H), 1.40–1.22 (m, 2H), 1.16 (s, 3H), 0.93 (s, 3H); 13C NMR (75 MHz, CDCl3): δ 140.1, 128.2 (2 C), 127.0, 126.7 (2 C), 83.6, 64.8, 54.5, 53.5, 43.3, 42.8, 41.1, 28.8, 26.4, 23.9, 17.5, 12.3. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.33807 (6) | 0.24169 (6) | 1.08282 (2) | 0.0830 (2) | |
C1 | 0.2296 (6) | 0.2012 (6) | 0.4937 (3) | 0.0780 (14) | |
C2 | 0.1800 (6) | 0.2745 (8) | 0.4120 (2) | 0.0780 (16) | |
H2 | 0.0609 | 0.3208 | 0.4009 | 0.094* | |
C3 | 0.2991 (8) | 0.2832 (7) | 0.3447 (3) | 0.0879 (17) | |
H3 | 0.2608 | 0.3360 | 0.2891 | 0.106* | |
C4 | 0.4716 (8) | 0.2156 (9) | 0.3585 (3) | 0.0983 (17) | |
H4 | 0.5545 | 0.2241 | 0.3136 | 0.118* | |
C6 | 0.4004 (10) | 0.1289 (8) | 0.5077 (4) | 0.1098 (18) | |
H6 | 0.4364 | 0.0752 | 0.5633 | 0.132* | |
C7 | 0.0995 (8) | 0.1880 (9) | 0.5670 (3) | 0.128 (3) | |
H7A | −0.0225 | 0.2319 | 0.5441 | 0.153* | |
H7B | 0.0844 | 0.0710 | 0.5832 | 0.153* | |
C18 | 0.2898 (6) | 0.3760 (5) | 0.9689 (2) | 0.0603 (9) | |
H18A | 0.2289 | 0.4802 | 0.9832 | 0.072* | |
H18B | 0.4084 | 0.4041 | 0.9461 | 0.072* | |
C5 | 0.5228 (9) | 0.1344 (8) | 0.4393 (5) | 0.120 (2) | |
H5 | 0.6394 | 0.0827 | 0.4489 | 0.144* | |
C8 | 0.0788 (5) | 0.2510 (9) | 0.7278 (2) | 0.0699 (10) | |
C15 | −0.0299 (5) | 0.2747 (6) | 0.9255 (3) | 0.0707 (12) | |
H15A | −0.0226 | 0.2281 | 0.9864 | 0.106* | |
H15B | −0.1079 | 0.2047 | 0.8840 | 0.106* | |
H15C | −0.0825 | 0.3855 | 0.9260 | 0.106* | |
C14 | 0.1671 (4) | 0.2839 (4) | 0.8935 (2) | 0.0487 (9) | |
C13 | 0.1869 (5) | 0.3763 (5) | 0.7982 (3) | 0.0475 (8) | |
C12 | 0.3983 (5) | 0.3471 (5) | 0.7893 (3) | 0.0530 (9) | |
H12A | 0.4237 | 0.3495 | 0.7252 | 0.064* | |
H12B | 0.4742 | 0.4320 | 0.8230 | 0.064* | |
C10 | 0.2460 (5) | 0.1195 (4) | 0.8614 (3) | 0.0561 (9) | |
H10 | 0.2521 | 0.0296 | 0.9074 | 0.067* | |
C9 | 0.1186 (7) | 0.0822 (7) | 0.7745 (3) | 0.0775 (14) | |
H9A | 0.0032 | 0.0304 | 0.7896 | 0.093* | |
H9B | 0.1798 | 0.0071 | 0.7346 | 0.093* | |
C17 | −0.1310 (5) | 0.2947 (8) | 0.7052 (3) | 0.097 (2) | |
H17A | −0.1429 | 0.3895 | 0.6644 | 0.146* | |
H17B | −0.1847 | 0.3216 | 0.7612 | 0.146* | |
H17C | −0.1956 | 0.2002 | 0.6762 | 0.146* | |
C11 | 0.4384 (5) | 0.1720 (5) | 0.8314 (3) | 0.0597 (10) | |
H11A | 0.5328 | 0.1774 | 0.8837 | 0.072* | |
H11B | 0.4796 | 0.0946 | 0.7861 | 0.072* | |
C16 | 0.1283 (6) | 0.5578 (5) | 0.7904 (3) | 0.0730 (12) | |
H16A | 0.1466 | 0.5988 | 0.7301 | 0.110* | |
H16B | 0.2025 | 0.6227 | 0.8359 | 0.110* | |
H16C | −0.0017 | 0.5674 | 0.8002 | 0.110* | |
O1 | 0.1688 (4) | 0.2767 (5) | 0.64360 (16) | 0.0847 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1108 (4) | 0.0852 (3) | 0.0521 (2) | −0.0089 (3) | 0.00362 (19) | 0.0109 (3) |
C1 | 0.080 (3) | 0.097 (4) | 0.055 (2) | −0.025 (3) | −0.005 (2) | −0.001 (2) |
C2 | 0.086 (3) | 0.084 (5) | 0.062 (2) | 0.007 (2) | −0.005 (2) | −0.014 (2) |
C3 | 0.118 (4) | 0.100 (5) | 0.0464 (18) | 0.014 (3) | 0.007 (2) | −0.003 (2) |
C4 | 0.105 (4) | 0.117 (5) | 0.075 (3) | 0.015 (4) | 0.019 (3) | −0.038 (4) |
C6 | 0.133 (5) | 0.110 (4) | 0.079 (3) | −0.003 (4) | −0.027 (4) | 0.030 (3) |
C7 | 0.112 (3) | 0.196 (7) | 0.074 (3) | −0.081 (4) | 0.005 (3) | −0.015 (3) |
C18 | 0.083 (3) | 0.053 (2) | 0.0474 (17) | −0.0022 (19) | 0.0206 (18) | 0.0045 (15) |
C5 | 0.100 (4) | 0.121 (4) | 0.132 (5) | 0.043 (4) | −0.017 (4) | −0.020 (4) |
C8 | 0.0567 (19) | 0.093 (3) | 0.0581 (17) | −0.014 (3) | −0.0028 (15) | 0.014 (3) |
C15 | 0.057 (2) | 0.084 (3) | 0.075 (2) | 0.000 (2) | 0.0306 (18) | 0.020 (2) |
C14 | 0.0442 (17) | 0.051 (3) | 0.0526 (16) | −0.0011 (14) | 0.0128 (15) | 0.0092 (13) |
C13 | 0.0381 (18) | 0.055 (2) | 0.052 (2) | −0.0026 (16) | 0.0143 (17) | 0.0082 (16) |
C12 | 0.0419 (19) | 0.067 (2) | 0.052 (2) | −0.0018 (17) | 0.0123 (17) | 0.0003 (17) |
C10 | 0.060 (2) | 0.047 (2) | 0.061 (2) | −0.0096 (17) | 0.0063 (19) | 0.0069 (17) |
C9 | 0.065 (3) | 0.093 (4) | 0.074 (3) | −0.024 (2) | 0.007 (2) | −0.007 (3) |
C17 | 0.048 (2) | 0.157 (6) | 0.086 (3) | −0.012 (2) | −0.003 (2) | 0.027 (3) |
C11 | 0.047 (2) | 0.069 (2) | 0.065 (2) | 0.0114 (17) | 0.0132 (19) | −0.0034 (18) |
C16 | 0.072 (3) | 0.066 (3) | 0.085 (3) | 0.023 (2) | 0.030 (2) | 0.025 (2) |
O1 | 0.0752 (16) | 0.130 (3) | 0.0482 (12) | −0.036 (2) | 0.0044 (12) | −0.0023 (16) |
Br1—C18 | 1.978 (3) | C15—H15A | 0.9600 |
C1—C2 | 1.342 (6) | C15—H15B | 0.9600 |
C1—C6 | 1.350 (7) | C15—H15C | 0.9600 |
C1—C7 | 1.491 (6) | C14—C10 | 1.519 (5) |
C2—C3 | 1.366 (6) | C14—C13 | 1.591 (5) |
C2—H2 | 0.9300 | C13—C16 | 1.506 (6) |
C3—C4 | 1.346 (7) | C13—C12 | 1.552 (5) |
C3—H3 | 0.9300 | C12—C11 | 1.539 (5) |
C4—C5 | 1.362 (8) | C12—H12A | 0.9700 |
C4—H4 | 0.9300 | C12—H12B | 0.9700 |
C6—C5 | 1.394 (8) | C10—C9 | 1.515 (6) |
C6—H6 | 0.9300 | C10—C11 | 1.546 (5) |
C7—O1 | 1.373 (6) | C10—H10 | 0.9800 |
C7—H7A | 0.9700 | C9—H9A | 0.9700 |
C7—H7B | 0.9700 | C9—H9B | 0.9700 |
C18—C14 | 1.526 (5) | C17—H17A | 0.9600 |
C18—H18A | 0.9700 | C17—H17B | 0.9600 |
C18—H18B | 0.9700 | C17—H17C | 0.9600 |
C5—H5 | 0.9300 | C11—H11A | 0.9700 |
C8—O1 | 1.457 (4) | C11—H11B | 0.9700 |
C8—C9 | 1.521 (8) | C16—H16A | 0.9600 |
C8—C17 | 1.547 (6) | C16—H16B | 0.9600 |
C8—C13 | 1.579 (6) | C16—H16C | 0.9600 |
C15—C14 | 1.533 (4) | ||
C2—C1—C6 | 118.4 (4) | C18—C14—C13 | 108.2 (3) |
C2—C1—C7 | 122.5 (5) | C15—C14—C13 | 116.9 (3) |
C6—C1—C7 | 119.0 (5) | C16—C13—C12 | 113.9 (3) |
C1—C2—C3 | 122.1 (5) | C16—C13—C8 | 116.2 (4) |
C1—C2—H2 | 119.0 | C12—C13—C8 | 105.7 (3) |
C3—C2—H2 | 119.0 | C16—C13—C14 | 117.5 (3) |
C4—C3—C2 | 120.2 (5) | C12—C13—C14 | 100.2 (3) |
C4—C3—H3 | 119.9 | C8—C13—C14 | 101.3 (3) |
C2—C3—H3 | 119.9 | C11—C12—C13 | 104.3 (3) |
C3—C4—C5 | 119.0 (5) | C11—C12—H12A | 110.9 |
C3—C4—H4 | 120.5 | C13—C12—H12A | 110.9 |
C5—C4—H4 | 120.5 | C11—C12—H12B | 110.9 |
C1—C6—C5 | 120.3 (5) | C13—C12—H12B | 110.9 |
C1—C6—H6 | 119.8 | H12A—C12—H12B | 108.9 |
C5—C6—H6 | 119.8 | C9—C10—C14 | 102.4 (3) |
O1—C7—C1 | 110.2 (4) | C9—C10—C11 | 107.3 (3) |
O1—C7—H7A | 109.6 | C14—C10—C11 | 103.0 (3) |
C1—C7—H7A | 109.6 | C9—C10—H10 | 114.3 |
O1—C7—H7B | 109.6 | C14—C10—H10 | 114.3 |
C1—C7—H7B | 109.6 | C11—C10—H10 | 114.3 |
H7A—C7—H7B | 108.1 | C10—C9—C8 | 105.8 (4) |
C14—C18—Br1 | 112.7 (2) | C10—C9—H9A | 110.6 |
C14—C18—H18A | 109.1 | C8—C9—H9A | 110.6 |
Br1—C18—H18A | 109.1 | C10—C9—H9B | 110.6 |
C14—C18—H18B | 109.1 | C8—C9—H9B | 110.6 |
Br1—C18—H18B | 109.1 | H9A—C9—H9B | 108.7 |
H18A—C18—H18B | 107.8 | C8—C17—H17A | 109.5 |
C4—C5—C6 | 119.9 (5) | C8—C17—H17B | 109.5 |
C4—C5—H5 | 120.0 | H17A—C17—H17B | 109.5 |
C6—C5—H5 | 120.0 | C8—C17—H17C | 109.5 |
O1—C8—C9 | 115.0 (5) | H17A—C17—H17C | 109.5 |
O1—C8—C17 | 107.0 (3) | H17B—C17—H17C | 109.5 |
C9—C8—C17 | 115.4 (4) | C12—C11—C10 | 102.8 (3) |
O1—C8—C13 | 103.3 (3) | C12—C11—H11A | 111.2 |
C9—C8—C13 | 102.0 (3) | C10—C11—H11A | 111.2 |
C17—C8—C13 | 113.6 (5) | C12—C11—H11B | 111.2 |
C14—C15—H15A | 109.5 | C10—C11—H11B | 111.2 |
C14—C15—H15B | 109.5 | H11A—C11—H11B | 109.1 |
H15A—C15—H15B | 109.5 | C13—C16—H16A | 109.5 |
C14—C15—H15C | 109.5 | C13—C16—H16B | 109.5 |
H15A—C15—H15C | 109.5 | H16A—C16—H16B | 109.5 |
H15B—C15—H15C | 109.5 | C13—C16—H16C | 109.5 |
C10—C14—C18 | 115.5 (3) | H16A—C16—H16C | 109.5 |
C10—C14—C15 | 115.8 (3) | H16B—C16—H16C | 109.5 |
C18—C14—C15 | 106.6 (3) | C7—O1—C8 | 117.3 (3) |
C10—C14—C13 | 93.5 (3) | ||
C6—C1—C2—C3 | −2.4 (8) | C18—C14—C13—C12 | 63.3 (3) |
C7—C1—C2—C3 | −178.8 (5) | C15—C14—C13—C12 | −176.4 (3) |
C1—C2—C3—C4 | 0.7 (9) | C10—C14—C13—C8 | 53.4 (3) |
C2—C3—C4—C5 | 2.0 (9) | C18—C14—C13—C8 | 171.7 (3) |
C2—C1—C6—C5 | 1.5 (9) | C15—C14—C13—C8 | −67.9 (4) |
C7—C1—C6—C5 | 177.9 (5) | C16—C13—C12—C11 | 161.3 (3) |
C2—C1—C7—O1 | −116.7 (6) | C8—C13—C12—C11 | −69.9 (4) |
C6—C1—C7—O1 | 67.0 (8) | C14—C13—C12—C11 | 35.0 (3) |
C3—C4—C5—C6 | −2.9 (10) | C18—C14—C10—C9 | −167.5 (3) |
C1—C6—C5—C4 | 1.2 (10) | C15—C14—C10—C9 | 66.8 (4) |
Br1—C18—C14—C10 | −60.3 (3) | C13—C14—C10—C9 | −55.4 (3) |
Br1—C18—C14—C15 | 70.0 (3) | C18—C14—C10—C11 | −56.2 (4) |
Br1—C18—C14—C13 | −163.4 (2) | C15—C14—C10—C11 | 178.1 (3) |
O1—C8—C13—C16 | 79.7 (4) | C13—C14—C10—C11 | 55.9 (3) |
C9—C8—C13—C16 | −160.7 (3) | C14—C10—C9—C8 | 38.0 (4) |
C17—C8—C13—C16 | −35.8 (4) | C11—C10—C9—C8 | −70.0 (4) |
O1—C8—C13—C12 | −47.7 (4) | O1—C8—C9—C10 | 108.8 (4) |
C9—C8—C13—C12 | 71.9 (3) | C17—C8—C9—C10 | −125.9 (4) |
C17—C8—C13—C12 | −163.2 (3) | C13—C8—C9—C10 | −2.2 (4) |
O1—C8—C13—C14 | −151.8 (3) | C13—C12—C11—C10 | −0.7 (3) |
C9—C8—C13—C14 | −32.2 (3) | C9—C10—C11—C12 | 71.6 (4) |
C17—C8—C13—C14 | 92.7 (4) | C14—C10—C11—C12 | −36.1 (3) |
C10—C14—C13—C16 | −178.9 (3) | C1—C7—O1—C8 | −168.4 (5) |
C18—C14—C13—C16 | −60.6 (4) | C9—C8—O1—C7 | 72.2 (5) |
C15—C14—C13—C16 | 59.7 (5) | C17—C8—O1—C7 | −57.5 (7) |
C10—C14—C13—C12 | −55.0 (3) | C13—C8—O1—C7 | −177.6 (5) |
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