data_2013376
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o254
_journal_page_last  o256
_publ_section_title
;
The sesquiterpenoid nootkatone and the absolute configuration of a
dibromo derivative
;
loop_
_publ_author_name
  'Sauer, Anne M.'
  'Fronczek, Frank R.'
  'Zhu, Betty C. R.'
  'Crowe, William E.'
  'Henderson, Gregg'
  'Laine, Roger A.'
_chemical_formula_moiety  'C15 H24 Br2 O'
_chemical_formula_sum  'C15 H24 Br2 O'
_chemical_formula_iupac  'C15 H24 Br2 O'
_chemical_formula_weight  380.16
_chemical_melting_point  '406-408K'
_symmetry_cell_setting  'Monoclinic'
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  13.500(3)
_cell_length_b  6.1403(10)
_cell_length_c  18.909(5)
_cell_angle_alpha  90
_cell_angle_beta  92.145(7)
_cell_angle_gamma  90
_cell_volume  1566.3(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  100
_exptl_crystal_density_diffrn  1.612
_diffrn_ambient_temperature  100
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  Br1A 0.31947(3) 0.63431(9) 0.38734(3) 0.02530(12) Uani d . 1 . . Br
  Br2A 0.71950(3) 0.65096(9) 0.46932(3) 0.02331(11) Uani d . 1 . . Br
  O1A 0.5042(3) 0.7030(5) 0.47129(19) 0.0210(8) Uani d . 1 . . O
  C1A 0.4379(3) 0.4506(7) 0.3845(3) 0.0161(10) Uani d . 1 . . C
  H1A 0.4218 0.3072 0.4064 0.019 Uiso calc R 1 . . H
  C2A 0.5197(3) 0.5570(7) 0.4304(3) 0.0155(9) Uani d . 1 . . C
  C3A 0.6222(3) 0.4556(7) 0.4236(2) 0.0145(9) Uani d . 1 . . C
  H3A 0.6229 0.3180 0.4519 0.017 Uiso calc R 1 . . H
  C4A 0.6501(3) 0.3935(9) 0.3483(2) 0.0153(8) Uani d . 1 . . C
  H4A 0.6590 0.5318 0.3213 0.018 Uiso calc R 1 . . H
  C5A 0.5647(3) 0.2638(7) 0.3104(3) 0.0135(9) Uani d . 1 . . C
  C6A 0.5925(4) 0.2194(8) 0.2334(3) 0.0196(10) Uani d . 1 . . C
  H6A1 0.6124 0.3587 0.2117 0.024 Uiso calc R 1 . . H
  H6A2 0.6508 0.1216 0.2339 0.024 Uiso calc R 1 . . H
  C7A 0.5095(3) 0.1164(8) 0.1864(2) 0.0190(10) Uani d . 1 . . C
  H7A 0.4912 -0.0249 0.2087 0.023 Uiso calc R 1 . . H
  C8A 0.4182(4) 0.2649(8) 0.1875(3) 0.0233(11) Uani d . 1 . . C
  H8A1 0.4337 0.4055 0.1648 0.028 Uiso calc R 1 . . H
  H8A2 0.3630 0.1963 0.1597 0.028 Uiso calc R 1 . . H
  C9A 0.3859(3) 0.3066(8) 0.2625(3) 0.0186(10) Uani d . 1 . . C
  H9A1 0.3650 0.1674 0.2837 0.022 Uiso calc R 1 . . H
  H9A2 0.3281 0.4060 0.2609 0.022 Uiso calc R 1 . . H
  C10A 0.4695(3) 0.4077(9) 0.3095(2) 0.0148(8) Uani d . 1 . . C
  H10A 0.4868 0.5513 0.2882 0.018 Uiso calc R 1 . . H
  C11A 0.5450(4) 0.0648(9) 0.1117(3) 0.0241(11) Uani d . 1 . . C
  H11A 0.5755 0.2002 0.0928 0.029 Uiso calc R 1 . . H
  C12A 0.6244(4) -0.1118(13) 0.1140(3) 0.0372(14) Uani d . 1 . . C
  H12A 0.5987 -0.2422 0.1369 0.056 Uiso calc R 1 . . H
  H12B 0.6830 -0.0591 0.1409 0.056 Uiso calc R 1 . . H
  H12C 0.6425 -0.1477 0.0657 0.056 Uiso calc R 1 . . H
  C13A 0.4611(4) -0.0035(11) 0.0597(3) 0.0337(14) Uani d . 1 . . C
  H13A 0.4881 -0.0319 0.0132 0.050 Uiso calc R 1 . . H
  H13B 0.4119 0.1136 0.0556 0.050 Uiso calc R 1 . . H
  H13C 0.4295 -0.1359 0.0770 0.050 Uiso calc R 1 . . H
  C14A 0.5487(4) 0.0440(7) 0.3484(3) 0.0180(10) Uani d . 1 . . C
  H14A 0.4898 -0.0281 0.3275 0.027 Uiso calc R 1 . . H
  H14B 0.5393 0.0702 0.3988 0.027 Uiso calc R 1 . . H
  H14C 0.6068 -0.0493 0.3428 0.027 Uiso calc R 1 . . H
  C15A 0.7499(4) 0.2750(9) 0.3515(3) 0.0220(10) Uani d . 1 . . C
  H15A 0.7428 0.1355 0.3760 0.033 Uiso calc R 1 . . H
  H15B 0.7993 0.3648 0.3772 0.033 Uiso calc R 1 . . H
  H15C 0.7715 0.2487 0.3033 0.033 Uiso calc R 1 . . H
  Br1B -0.18748(3) 0.40480(9) 0.09903(3) 0.02568(11) Uani d . 1 . . Br
  Br2B 0.21533(3) 0.40203(11) 0.04876(3) 0.02671(12) Uani d . 1 . . Br
  O1B 0.0012(3) 0.3464(5) 0.02916(19) 0.0216(8) Uani d . 1 . . O
  C1B -0.0709(3) 0.5932(7) 0.1113(3) 0.0159(10) Uani d . 1 . . C
  H1B -0.0871 0.7364 0.0886 0.019 Uiso calc R 1 . . H
  C2B 0.0140(4) 0.4910(7) 0.0715(3) 0.0161(9) Uani d . 1 . . C
  C3B 0.1152(3) 0.5943(7) 0.0865(2) 0.0145(9) Uani d . 1 . . C
  H3B 0.1167 0.7319 0.0583 0.017 Uiso calc R 1 . . H
  C4B 0.1396(3) 0.6571(9) 0.1641(2) 0.0149(8) Uani d . 1 . . C
  H4B 0.1477 0.5193 0.1919 0.018 Uiso calc R 1 . . H
  C5B 0.0514(3) 0.7868(7) 0.1950(3) 0.0149(9) Uani d . 1 . . C
  C6B 0.0746(3) 0.8319(7) 0.2737(3) 0.0160(9) Uani d . 1 . . C
  H6B1 0.1320 0.9318 0.2780 0.019 Uiso calc R 1 . . H
  H6B2 0.0938 0.6935 0.2973 0.019 Uiso calc R 1 . . H
  C7B -0.0126(3) 0.9326(8) 0.3124(2) 0.0183(10) Uani d . 1 . . C
  H7B -0.0332 1.0662 0.2854 0.022 Uiso calc R 1 . . H
  C8B -0.0995(4) 0.7742(8) 0.3068(3) 0.0216(10) Uani d . 1 . . C
  H8B1 -0.0807 0.6354 0.3304 0.026 Uiso calc R 1 . . H
  H8B2 -0.1566 0.8359 0.3314 0.026 Uiso calc R 1 . . H
  C9B -0.1293(4) 0.7307(8) 0.2297(3) 0.0204(10) Uani d . 1 . . C
  H9B1 -0.1515 0.8684 0.2069 0.024 Uiso calc R 1 . . H
  H9B2 -0.1857 0.6274 0.2273 0.024 Uiso calc R 1 . . H
  C10B -0.0433(3) 0.6359(9) 0.1893(2) 0.0148(8) Uani d . 1 . . C
  H10B -0.0252 0.4930 0.2115 0.018 Uiso calc R 1 . . H
  C11B 0.0138(4) 1.0057(8) 0.3891(3) 0.0213(11) Uani d . 1 . . C
  H11B -0.0490 1.0596 0.4093 0.026 Uiso calc R 1 . . H
  C12B 0.0518(4) 0.8221(8) 0.4373(3) 0.0236(11) Uani d . 1 . . C
  H12D 0.1155 0.7695 0.4208 0.035 Uiso calc R 1 . . H
  H12E 0.0038 0.7023 0.4362 0.035 Uiso calc R 1 . . H
  H12F 0.0606 0.8766 0.4858 0.035 Uiso calc R 1 . . H
  C13B 0.0860(4) 1.1991(9) 0.3898(3) 0.0314(13) Uani d . 1 . . C
  H13D 0.0954 1.2537 0.4383 0.047 Uiso calc R 1 . . H
  H13E 0.0587 1.3153 0.3594 0.047 Uiso calc R 1 . . H
  H13F 0.1499 1.1517 0.3723 0.047 Uiso calc R 1 . . H
  C14B 0.0340(4) 1.0032(7) 0.1551(3) 0.0185(10) Uani d . 1 . . C
  H14D -0.0298 1.0649 0.1678 0.028 Uiso calc R 1 . . H
  H14E 0.0337 0.9765 0.1040 0.028 Uiso calc R 1 . . H
  H14F 0.0873 1.1056 0.1683 0.028 Uiso calc R 1 . . H
  C15B 0.2377(4) 0.7796(9) 0.1696(3) 0.0207(10) Uani d . 1 . . C
  H15D 0.2895 0.6921 0.1483 0.031 Uiso calc R 1 . . H
  H15E 0.2558 0.8065 0.2195 0.031 Uiso calc R 1 . . H
  H15F 0.2310 0.9188 0.1446 0.031 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  Br1A 0.0172(2) 0.0302(3) 0.0285(3) 0.0093(2) 0.00145(18) -0.0048(3)
  Br2A 0.0201(2) 0.0270(2) 0.0225(2) -0.0045(2) -0.00245(18) -0.0052(2)
  O1A 0.0268(18) 0.0178(17) 0.0185(18) 0.0024(14) 0.0034(15) -0.0039(14)
  C1A 0.012(2) 0.016(2) 0.020(2) 0.0058(17) 0.0015(17) 0.0010(18)
  C2A 0.014(2) 0.016(2) 0.017(2) -0.0019(18) 0.0002(18) 0.0055(19)
  C3A 0.014(2) 0.013(2) 0.016(2) -0.0021(16) -0.0011(17) 0.0004(17)
  C4A 0.0152(19) 0.015(2) 0.015(2) -0.002(2) -0.0006(15) 0.002(2)
  C5A 0.014(2) 0.013(2) 0.014(2) 0.0001(17) -0.0005(17) -0.0006(18)
  C6A 0.018(2) 0.024(2) 0.017(3) 0.0019(19) 0.0055(18) -0.001(2)
  C7A 0.021(2) 0.018(2) 0.017(2) 0.002(2) -0.0017(17) -0.002(2)
  C8A 0.024(3) 0.022(3) 0.023(3) 0.000(2) -0.005(2) 0.001(2)
  C9A 0.014(2) 0.024(2) 0.017(3) 0.0033(19) -0.0012(18) -0.004(2)
  C10A 0.0175(19) 0.0141(19) 0.013(2) 0.004(2) -0.0015(15) -0.002(2)
  C11A 0.028(3) 0.029(3) 0.016(3) -0.001(2) 0.002(2) 0.000(2)
  C12A 0.032(3) 0.054(4) 0.026(3) 0.009(3) 0.001(2) -0.011(3)
  C13A 0.035(3) 0.047(3) 0.019(3) 0.000(3) 0.001(2) -0.003(3)
  C14A 0.020(2) 0.014(2) 0.021(3) 0.0016(18) 0.001(2) -0.0021(19)
  C15A 0.019(2) 0.022(2) 0.025(3) 0.0008(19) 0.0008(19) -0.007(2)
  Br1B 0.0182(2) 0.0256(2) 0.0330(3) -0.0054(2) -0.00305(19) -0.0070(3)
  Br2B 0.0232(2) 0.0346(3) 0.0224(3) 0.0103(3) 0.00155(18) -0.0071(3)
  O1B 0.0277(18) 0.0182(18) 0.0187(19) 0.0012(14) -0.0019(15) -0.0008(14)
  C1B 0.016(2) 0.012(2) 0.020(2) -0.0019(16) -0.0022(17) -0.0010(17)
  C2B 0.021(2) 0.015(2) 0.012(2) 0.0007(19) -0.0023(18) 0.0026(19)
  C3B 0.016(2) 0.016(2) 0.011(2) 0.0092(17) 0.0034(16) -0.0021(17)
  C4B 0.0157(19) 0.016(2) 0.012(2) 0.004(2) -0.0034(15) -0.003(2)
  C5B 0.014(2) 0.015(2) 0.016(2) 0.0008(17) -0.0009(18) 0.0015(19)
  C6B 0.015(2) 0.014(2) 0.018(2) -0.0014(17) 0.0008(18) -0.0011(18)
  C7B 0.024(2) 0.019(2) 0.012(2) 0.000(2) 0.0018(17) -0.0029(19)
  C8B 0.019(2) 0.024(3) 0.022(3) -0.001(2) 0.003(2) -0.003(2)
  C9B 0.015(2) 0.022(2) 0.025(3) 0.0034(19) 0.0018(19) -0.002(2)
  C10B 0.0153(19) 0.0134(19) 0.015(2) 0.000(2) 0.0000(15) 0.000(2)
  C11B 0.020(2) 0.023(2) 0.021(3) 0.003(2) 0.001(2) -0.006(2)
  C12B 0.030(3) 0.026(3) 0.015(3) 0.004(2) 0.003(2) 0.002(2)
  C13B 0.042(3) 0.027(3) 0.025(3) -0.004(2) -0.006(2) 0.000(2)
  C14B 0.023(2) 0.012(2) 0.020(3) -0.0002(18) 0.002(2) -0.0004(19)
  C15B 0.018(2) 0.027(3) 0.017(3) 0.001(2) 0.0010(19) 0.001(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  Br1A C1A . 1.959(4) y
  Br2A C3A . 1.956(4) y
  O1A C2A . 1.207(6) y
  C1A C10A . 1.520(6) ?
  C1A C2A . 1.526(6) ?
  C1A H1A . 1.0000 ?
  C2A C3A . 1.527(6) ?
  C3A C4A . 1.535(6) ?
  C3A H3A . 1.0000 ?
  C4A C15A . 1.530(6) ?
  C4A C5A . 1.554(6) ?
  C4A H4A . 1.0000 ?
  C5A C6A . 1.543(7) ?
  C5A C14A . 1.547(6) ?
  C5A C10A . 1.560(6) ?
  C6A C7A . 1.540(7) ?
  C6A H6A1 . 0.9900 ?
  C6A H6A2 . 0.9900 ?
  C7A C8A . 1.533(7) ?
  C7A C11A . 1.541(7) ?
  C7A H7A . 1.0000 ?
  C8A C9A . 1.521(7) ?
  C8A H8A1 . 0.9900 ?
  C8A H8A2 . 0.9900 ?
  C9A C10A . 1.540(6) ?
  C9A H9A1 . 0.9900 ?
  C9A H9A2 . 0.9900 ?
  C10A H10A . 1.0000 ?
  C11A C12A . 1.524(8) ?
  C11A C13A . 1.531(8) ?
  C11A H11A . 1.0000 ?
  C12A H12A . 0.9800 ?
  C12A H12B . 0.9800 ?
  C12A H12C . 0.9800 ?
  C13A H13A . 0.9800 ?
  C13A H13B . 0.9800 ?
  C13A H13C . 0.9800 ?
  C14A H14A . 0.9800 ?
  C14A H14B . 0.9800 ?
  C14A H14C . 0.9800 ?
  C15A H15A . 0.9800 ?
  C15A H15B . 0.9800 ?
  C15A H15C . 0.9800 ?
  Br1B C1B . 1.960(4) y
  Br2B C3B . 1.950(4) y
  O1B C2B . 1.203(6) y
  C1B C10B . 1.529(6) ?
  C1B C2B . 1.530(7) ?
  C1B H1B . 1.0000 ?
  C2B C3B . 1.523(6) ?
  C3B C4B . 1.542(6) ?
  C3B H3B . 1.0000 ?
  C4B C15B . 1.523(6) ?
  C4B C5B . 1.564(6) ?
  C4B H4B . 1.0000 ?
  C5B C6B . 1.535(7) ?
  C5B C14B . 1.541(6) ?
  C5B C10B . 1.579(6) ?
  C6B C7B . 1.538(6) ?
  C6B H6B1 . 0.9900 ?
  C6B H6B2 . 0.9900 ?
  C7B C8B . 1.525(7) ?
  C7B C11B . 1.547(7) ?
  C7B H7B . 1.0000 ?
  C8B C9B . 1.522(7) ?
  C8B H8B1 . 0.9900 ?
  C8B H8B2 . 0.9900 ?
  C9B C10B . 1.529(6) ?
  C9B H9B1 . 0.9900 ?
  C9B H9B2 . 0.9900 ?
  C10B H10B . 1.0000 ?
  C11B C12B . 1.527(7) ?
  C11B C13B . 1.536(7) ?
  C11B H11B . 1.0000 ?
  C12B H12D . 0.9800 ?
  C12B H12E . 0.9800 ?
  C12B H12F . 0.9800 ?
  C13B H13D . 0.9800 ?
  C13B H13E . 0.9800 ?
  C13B H13F . 0.9800 ?
  C14B H14D . 0.9800 ?
  C14B H14E . 0.9800 ?
  C14B H14F . 0.9800 ?
  C15B H15D . 0.9800 ?
  C15B H15E . 0.9800 ?
  C15B H15F . 0.9800 ?