Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017296/jh2017sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017296/jh2017Isup2.hkl |
CCDC reference: 613744
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); 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) and PLATON (Spek, 2003).
C20H26BrNO3 | F(000) = 848 |
Mr = 408.33 | Dx = 1.389 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 19890 reflections |
a = 8.7388 (3) Å | θ = 1.5–27.5° |
b = 14.0200 (8) Å | µ = 2.12 mm−1 |
c = 15.9341 (7) Å | T = 295 K |
V = 1952.21 (16) Å3 | Block, colorless |
Z = 4 | 0.36 × 0.30 × 0.26 mm |
Rigaku RAXIS-RAPID diffractometer | 3817 reflections with I > 2σ(I) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.036 |
ω scans | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→11 |
Tmin = 0.438, Tmax = 0.575 | k = −18→18 |
18127 measured reflections | l = −20→20 |
4380 independent reflections |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0369P)2 + 0.3642P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.032 | (Δ/σ)max = 0.001 |
wR(F2) = 0.069 | Δρmax = 0.25 e Å−3 |
S = 1.04 | Δρmin = −0.46 e Å−3 |
4380 reflections | Absolute structure: Flack (1983) |
230 parameters | Absolute structure parameter: 0.001 (7) |
0 restraints |
Experimental. 1H NMR (500 MHz, CDCl3): δ 0.78–1.10 (m, 11H), 1.56 (m, 3H),1.60–1.82 (m,5H), 1.91 (m, 3H), 2.25 (m, 1H), 2.57 (m, 1H), 5.25 (dd, 1H), 6.95 (m, 1H), 7.12 (m, 1H), 7.53 (m, 1H), 7.98 (m, 1H); ESI-MS: m/z = 430 [M + Na]+. |
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 | ||
Br1 | 0.77307 (3) | 0.141459 (17) | 0.533053 (19) | 0.05205 (9) | |
O1 | 0.6407 (3) | 0.23318 (11) | 0.35334 (10) | 0.0493 (5) | |
O2 | 0.62001 (18) | 0.51921 (10) | 0.33761 (9) | 0.0335 (3) | |
O3 | 0.85457 (17) | 0.36674 (12) | 0.52246 (10) | 0.0418 (4) | |
N1 | 0.6868 (2) | 0.37838 (11) | 0.41284 (11) | 0.0282 (4) | |
C1 | 0.6001 (4) | 0.2850 (2) | 0.61486 (16) | 0.0545 (7) | |
H1A | 0.5329 | 0.3391 | 0.6123 | 0.082* | |
H1B | 0.6894 | 0.3012 | 0.6469 | 0.082* | |
H1C | 0.5481 | 0.2327 | 0.6411 | 0.082* | |
C2 | 0.6476 (2) | 0.25668 (14) | 0.52625 (14) | 0.0330 (4) | |
H2 | 0.5567 | 0.2446 | 0.4918 | 0.040* | |
C3 | 0.7436 (2) | 0.33582 (13) | 0.48726 (13) | 0.0305 (4) | |
C4 | 0.6345 (3) | 0.31904 (15) | 0.34816 (14) | 0.0338 (5) | |
C5 | 0.5733 (3) | 0.36866 (16) | 0.27397 (13) | 0.0346 (5) | |
C6 | 0.5134 (4) | 0.31716 (18) | 0.20665 (16) | 0.0481 (7) | |
H6 | 0.5176 | 0.2509 | 0.2069 | 0.058* | |
C7 | 0.4483 (3) | 0.3643 (2) | 0.13996 (16) | 0.0554 (7) | |
H7 | 0.4088 | 0.3300 | 0.0950 | 0.066* | |
C8 | 0.4416 (3) | 0.4631 (2) | 0.13990 (16) | 0.0494 (7) | |
H8 | 0.3963 | 0.4946 | 0.0950 | 0.059* | |
C9 | 0.5013 (3) | 0.51518 (18) | 0.20561 (14) | 0.0410 (6) | |
H9 | 0.4975 | 0.5815 | 0.2052 | 0.049* | |
C10 | 0.5668 (3) | 0.46687 (16) | 0.27180 (13) | 0.0314 (5) | |
C11 | 0.7348 (3) | 0.47884 (13) | 0.39153 (12) | 0.0293 (4) | |
C12 | 0.7333 (3) | 0.54652 (13) | 0.46800 (13) | 0.0328 (4) | |
H12 | 0.8121 | 0.5231 | 0.5066 | 0.039* | |
C13 | 0.5820 (3) | 0.54761 (16) | 0.51779 (15) | 0.0395 (5) | |
H13 | 0.5445 | 0.4818 | 0.5196 | 0.047* | |
C14 | 0.4536 (3) | 0.6085 (2) | 0.48171 (19) | 0.0577 (7) | |
H14A | 0.4842 | 0.6742 | 0.4816 | 0.087* | |
H14B | 0.3634 | 0.6011 | 0.5155 | 0.087* | |
H14C | 0.4322 | 0.5884 | 0.4253 | 0.087* | |
C15 | 0.6134 (4) | 0.5779 (2) | 0.60842 (17) | 0.0620 (8) | |
H15A | 0.5186 | 0.5807 | 0.6388 | 0.093* | |
H15B | 0.6610 | 0.6396 | 0.6088 | 0.093* | |
H15C | 0.6802 | 0.5323 | 0.6345 | 0.093* | |
C16 | 0.7868 (3) | 0.64563 (16) | 0.43793 (15) | 0.0432 (5) | |
H16A | 0.7140 | 0.6703 | 0.3974 | 0.052* | |
H16B | 0.7889 | 0.6891 | 0.4853 | 0.052* | |
C17 | 0.9437 (3) | 0.6418 (2) | 0.39838 (17) | 0.0533 (6) | |
H17A | 1.0172 | 0.6204 | 0.4399 | 0.064* | |
H17B | 0.9730 | 0.7054 | 0.3808 | 0.064* | |
C18 | 0.9491 (3) | 0.57510 (19) | 0.32293 (15) | 0.0438 (6) | |
H18 | 0.8812 | 0.6008 | 0.2795 | 0.053* | |
C19 | 1.1096 (4) | 0.5688 (3) | 0.2868 (2) | 0.0637 (8) | |
H19A | 1.1777 | 0.5430 | 0.3283 | 0.096* | |
H19B | 1.1437 | 0.6313 | 0.2709 | 0.096* | |
H19C | 1.1089 | 0.5281 | 0.2384 | 0.096* | |
C20 | 0.8894 (3) | 0.47709 (16) | 0.34841 (14) | 0.0355 (5) | |
H20A | 0.8821 | 0.4375 | 0.2986 | 0.043* | |
H20B | 0.9632 | 0.4476 | 0.3858 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.04328 (12) | 0.03013 (11) | 0.08274 (19) | 0.00304 (10) | −0.00087 (13) | 0.01514 (12) |
O1 | 0.0839 (13) | 0.0233 (8) | 0.0408 (9) | −0.0030 (8) | −0.0065 (9) | −0.0022 (7) |
O2 | 0.0435 (9) | 0.0231 (7) | 0.0341 (8) | 0.0038 (6) | −0.0097 (7) | −0.0003 (6) |
O3 | 0.0398 (8) | 0.0330 (8) | 0.0526 (9) | −0.0046 (7) | −0.0137 (8) | 0.0065 (8) |
N1 | 0.0340 (9) | 0.0209 (9) | 0.0296 (9) | −0.0019 (6) | −0.0002 (8) | −0.0003 (6) |
C1 | 0.073 (2) | 0.0496 (16) | 0.0411 (14) | −0.0056 (14) | 0.0101 (14) | 0.0024 (12) |
C2 | 0.0315 (10) | 0.0284 (10) | 0.0392 (11) | 0.0012 (8) | −0.0005 (11) | 0.0068 (10) |
C3 | 0.0326 (11) | 0.0229 (9) | 0.0360 (11) | 0.0047 (8) | 0.0018 (10) | −0.0006 (7) |
C4 | 0.0419 (12) | 0.0268 (11) | 0.0327 (11) | −0.0029 (9) | 0.0019 (11) | −0.0007 (9) |
C5 | 0.0422 (12) | 0.0290 (11) | 0.0326 (11) | −0.0040 (10) | −0.0015 (9) | −0.0018 (9) |
C6 | 0.0739 (19) | 0.0321 (13) | 0.0382 (13) | −0.0113 (12) | −0.0091 (14) | −0.0037 (10) |
C7 | 0.0766 (19) | 0.0526 (16) | 0.0370 (12) | −0.0165 (16) | −0.0143 (13) | −0.0019 (12) |
C8 | 0.0587 (17) | 0.0537 (16) | 0.0358 (13) | −0.0032 (13) | −0.0140 (13) | 0.0058 (11) |
C9 | 0.0469 (14) | 0.0360 (13) | 0.0402 (12) | 0.0020 (10) | −0.0067 (11) | 0.0044 (10) |
C10 | 0.0313 (11) | 0.0314 (11) | 0.0317 (11) | −0.0017 (9) | 0.0008 (9) | −0.0024 (8) |
C11 | 0.0356 (11) | 0.0206 (8) | 0.0317 (10) | −0.0008 (9) | −0.0055 (10) | 0.0009 (7) |
C12 | 0.0418 (11) | 0.0230 (8) | 0.0336 (10) | −0.0007 (8) | −0.0063 (12) | −0.0036 (8) |
C13 | 0.0464 (13) | 0.0297 (11) | 0.0422 (13) | 0.0010 (9) | 0.0029 (11) | −0.0044 (9) |
C14 | 0.0508 (15) | 0.0614 (17) | 0.0610 (17) | 0.0179 (12) | 0.0001 (15) | −0.0080 (14) |
C15 | 0.072 (2) | 0.072 (2) | 0.0418 (15) | 0.0092 (17) | 0.0046 (15) | −0.0091 (14) |
C16 | 0.0611 (14) | 0.0225 (10) | 0.0461 (12) | −0.0091 (12) | −0.0031 (11) | −0.0036 (9) |
C17 | 0.0679 (16) | 0.0392 (13) | 0.0528 (15) | −0.0271 (14) | 0.0002 (13) | −0.0012 (13) |
C18 | 0.0491 (14) | 0.0417 (14) | 0.0406 (13) | −0.0128 (12) | −0.0001 (12) | 0.0063 (11) |
C19 | 0.0554 (17) | 0.073 (2) | 0.0629 (18) | −0.0212 (16) | 0.0105 (15) | 0.0048 (16) |
C20 | 0.0388 (12) | 0.0336 (12) | 0.0340 (11) | −0.0040 (9) | −0.0010 (10) | 0.0020 (9) |
Br1—C2 | 1.956 (2) | C12—C13 | 1.542 (3) |
O1—C4 | 1.208 (3) | C12—C16 | 1.542 (3) |
O2—C10 | 1.362 (3) | C12—H12 | 0.9800 |
O2—C11 | 1.437 (3) | C13—C14 | 1.522 (3) |
O3—C3 | 1.201 (3) | C13—C15 | 1.530 (4) |
N1—C4 | 1.401 (3) | C13—H13 | 0.9800 |
N1—C3 | 1.417 (3) | C14—H14A | 0.9600 |
N1—C11 | 1.508 (2) | C14—H14B | 0.9600 |
C1—C2 | 1.524 (4) | C14—H14C | 0.9600 |
C1—H1A | 0.9600 | C15—H15A | 0.9600 |
C1—H1B | 0.9600 | C15—H15B | 0.9600 |
C1—H1C | 0.9600 | C15—H15C | 0.9600 |
C2—C3 | 1.524 (3) | C16—C17 | 1.510 (4) |
C2—H2 | 0.9800 | C16—H16A | 0.9700 |
C4—C5 | 1.472 (3) | C16—H16B | 0.9700 |
C5—C10 | 1.378 (3) | C17—C18 | 1.524 (4) |
C5—C6 | 1.395 (3) | C17—H17A | 0.9700 |
C6—C7 | 1.375 (4) | C17—H17B | 0.9700 |
C6—H6 | 0.9300 | C18—C19 | 1.519 (4) |
C7—C8 | 1.385 (4) | C18—C20 | 1.525 (3) |
C7—H7 | 0.9300 | C18—H18 | 0.9800 |
C8—C9 | 1.379 (4) | C19—H19A | 0.9600 |
C8—H8 | 0.9300 | C19—H19B | 0.9600 |
C9—C10 | 1.378 (3) | C19—H19C | 0.9600 |
C9—H9 | 0.9300 | C20—H20A | 0.9700 |
C11—C20 | 1.516 (3) | C20—H20B | 0.9700 |
C11—C12 | 1.545 (3) | ||
C10—O2—C11 | 119.12 (16) | C16—C12—H12 | 106.5 |
C4—N1—C3 | 118.67 (16) | C11—C12—H12 | 106.5 |
C4—N1—C11 | 118.66 (16) | C14—C13—C15 | 109.5 (2) |
C3—N1—C11 | 118.96 (16) | C14—C13—C12 | 116.3 (2) |
C2—C1—H1A | 109.5 | C15—C13—C12 | 109.6 (2) |
C2—C1—H1B | 109.5 | C14—C13—H13 | 107.0 |
H1A—C1—H1B | 109.5 | C15—C13—H13 | 107.0 |
C2—C1—H1C | 109.5 | C12—C13—H13 | 107.0 |
H1A—C1—H1C | 109.5 | C13—C14—H14A | 109.5 |
H1B—C1—H1C | 109.5 | C13—C14—H14B | 109.5 |
C3—C2—C1 | 109.73 (18) | H14A—C14—H14B | 109.5 |
C3—C2—Br1 | 108.37 (13) | C13—C14—H14C | 109.5 |
C1—C2—Br1 | 108.47 (16) | H14A—C14—H14C | 109.5 |
C3—C2—H2 | 110.1 | H14B—C14—H14C | 109.5 |
C1—C2—H2 | 110.1 | C13—C15—H15A | 109.5 |
Br1—C2—H2 | 110.1 | C13—C15—H15B | 109.5 |
O3—C3—N1 | 121.4 (2) | H15A—C15—H15B | 109.5 |
O3—C3—C2 | 121.13 (19) | C13—C15—H15C | 109.5 |
N1—C3—C2 | 117.06 (18) | H15A—C15—H15C | 109.5 |
O1—C4—N1 | 121.8 (2) | H15B—C15—H15C | 109.5 |
O1—C4—C5 | 122.8 (2) | C17—C16—C12 | 111.9 (2) |
N1—C4—C5 | 115.38 (18) | C17—C16—H16A | 109.2 |
C10—C5—C6 | 118.8 (2) | C12—C16—H16A | 109.2 |
C10—C5—C4 | 120.48 (19) | C17—C16—H16B | 109.2 |
C6—C5—C4 | 120.6 (2) | C12—C16—H16B | 109.2 |
C7—C6—C5 | 120.0 (2) | H16A—C16—H16B | 107.9 |
C7—C6—H6 | 120.0 | C16—C17—C18 | 112.3 (2) |
C5—C6—H6 | 120.0 | C16—C17—H17A | 109.1 |
C6—C7—C8 | 119.9 (2) | C18—C17—H17A | 109.1 |
C6—C7—H7 | 120.1 | C16—C17—H17B | 109.1 |
C8—C7—H7 | 120.1 | C18—C17—H17B | 109.1 |
C9—C8—C7 | 120.9 (2) | H17A—C17—H17B | 107.9 |
C9—C8—H8 | 119.6 | C19—C18—C17 | 111.3 (2) |
C7—C8—H8 | 119.6 | C19—C18—C20 | 111.4 (2) |
C10—C9—C8 | 118.5 (2) | C17—C18—C20 | 109.4 (2) |
C10—C9—H9 | 120.7 | C19—C18—H18 | 108.2 |
C8—C9—H9 | 120.7 | C17—C18—H18 | 108.2 |
O2—C10—C9 | 117.8 (2) | C20—C18—H18 | 108.2 |
O2—C10—C5 | 120.3 (2) | C18—C19—H19A | 109.5 |
C9—C10—C5 | 121.8 (2) | C18—C19—H19B | 109.5 |
O2—C11—N1 | 107.96 (16) | H19A—C19—H19B | 109.5 |
O2—C11—C20 | 110.95 (16) | C18—C19—H19C | 109.5 |
N1—C11—C20 | 109.56 (17) | H19A—C19—H19C | 109.5 |
O2—C11—C12 | 102.93 (15) | H19B—C19—H19C | 109.5 |
N1—C11—C12 | 113.18 (16) | C11—C20—C18 | 114.3 (2) |
C20—C11—C12 | 112.02 (18) | C11—C20—H20A | 108.7 |
C13—C12—C16 | 114.24 (18) | C18—C20—H20A | 108.7 |
C13—C12—C11 | 114.79 (17) | C11—C20—H20B | 108.7 |
C16—C12—C11 | 107.81 (17) | C18—C20—H20B | 108.7 |
C13—C12—H12 | 106.5 | H20A—C20—H20B | 107.6 |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O3i | 0.98 | 2.37 | 3.187 (2) | 141 |
C9—H9···O1ii | 0.93 | 2.62 | 3.430 (3) | 146 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+1, y+1/2, −z+1/2. |