data_2012113
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  958
_journal_page_last  960
_publ_section_title
;
 Hamigerin A and a Hamigerin D decomposition product
;
loop_
_publ_author_name
  'Cambie, Richard C.'
  'Rickard, Clifton E. F.'
  'Rutledge, P. Stewart'
  'Wellington, Keri D.'
_chemical_formula_moiety  'C20 H25 Br O5'
_chemical_formula_sum  'C20 H25 Br O5'
_chemical_formula_weight  425.31
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  7.0958(13)
_cell_length_b  16.050(3)
_cell_length_c  16.856(4)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1919.7(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  203(2)
_exptl_crystal_density_diffrn  1.472
_diffrn_ambient_temperature  203(2)
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
  Br1  .17413(10)  .12957(4)  .49179(3)  .0873(3) Uani d . 1 . . Br
  O1  .0612(5)  -.2713(2)  .25439(19)  .0661(10) Uani d . 1 . . O
  H1  -.0136  -.3074  .2387  .099 Uiso calc R 1 . . H
  O2  .2661(6)  -.1571(2)  .3248(2)  .0694(11) Uani d . 1 . . O
  O3  .3027(5)  -.0233(2)  .4081(2)  .0673(10) Uani d . 1 . . O
  H3A  .335(10)  -.068(4)  .378(4)  .101 Uiso d . 1 . . H
  O4  -.3056(6)  -.2094(2)  .3777(2)  .0784(12) Uani d . 1 . . O
  O5  -.0482(5)  -.2816(2)  .40302(19)  .0649(10) Uani d . 1 . . O
  C1  .1220(7)  -.0049(3)  .3868(2)  .0472(12) Uani d . 1 . . C
  C2  .0338(8)  .0645(3)  .4183(2)  .0515(13) Uani d . 1 . . C
  C3  -.1486(8)  .0843(2)  .3992(2)  .0462(11) Uani d . 1 . . C
  C4  -.2463(7)  .0330(2)  .3462(2)  .0402(10) Uani d . 1 . . C
  H4A  -.3722  .0460  .3339  .048 Uiso calc R 1 . . H
  C4A  -.1646(6)  -.0360(2)  .31115(19)  .0341(9) Uani d . 1 . . C
  C5  -.2706(6)  -.0850(2)  .2487(2)  .0330(9) Uani d . 1 . . C
  H5A  -.3968  -.0998  .2694  .040 Uiso calc R 1 . . H
  C6  -.2935(6)  -.0378(2)  .1681(2)  .0368(10) Uani d . 1 . . C
  H6A  -.3774  -.0726  .1349  .044 Uiso calc R 1 . . H
  C7  -.0964(7)  -.0467(3)  .1329(2)  .0486(11) Uani d . 1 . . C
  H7A  -.0989  -.0374  .0754  .058 Uiso calc R 1 . . H
  H7B  -.0095  -.0066  .1570  .058 Uiso calc R 1 . . H
  C8  -.0366(7)  -.1351(3)  .1514(2)  .0519(12) Uani d . 1 . . C
  H8A  .0958  -.1366  .1678  .062 Uiso calc R 1 . . H
  H8B  -.0520  -.1707  .1047  .062 Uiso calc R 1 . . H
  C9  -.1677(7)  -.1659(2)  .2209(2)  .0396(9) Uani d . 1 . . C
  C10  -.0399(7)  -.2038(2)  .2861(2)  .0425(10) Uani d . 1 . . C
  C11  .0993(7)  -.1377(3)  .3147(2)  .0467(11) Uani d . 1 . . C
  C11A  .0203(7)  -.0568(3)  .3343(2)  .0401(10) Uani d . 1 . . C
  C12  -.3795(7)  .0495(2)  .1681(2)  .0429(11) Uani d . 1 . . C
  H12A  -.3099  .0845  .2066  .051 Uiso calc R 1 . . H
  C13  -.3655(8)  .0897(3)  .0862(3)  .0624(14) Uani d . 1 . . C
  H13A  -.4208  .1449  .0878  .094 Uiso calc R 1 . . H
  H13B  -.4328  .0558  .0479  .094 Uiso calc R 1 . . H
  H13C  -.2342  .0938  .0708  .094 Uiso calc R 1 . . H
  C14  -.5874(8)  .0467(3)  .1926(3)  .0598(13) Uani d . 1 . . C
  H14A  -.5984  .0213  .2446  .090 Uiso calc R 1 . . H
  H14B  -.6580  .0142  .1543  .090 Uiso calc R 1 . . H
  H14C  -.6373  .1030  .1945  .090 Uiso calc R 1 . . H
  C15  -.3108(9)  -.2304(3)  .1928(3)  .0589(13) Uani d . 1 . . C
  H15A  -.2453  -.2803  .1758  .088 Uiso calc R 1 . . H
  H15B  -.3825  -.2078  .1488  .088 Uiso calc R 1 . . H
  H15C  -.3956  -.2440  .2360  .088 Uiso calc R 1 . . H
  C16  -.2478(9)  .1595(3)  .4321(3)  .0699(16) Uani d . 1 . . C
  H16A  -.3742  .1625  .4104  .105 Uiso calc R 1 . . H
  H16B  -.1786  .2094  .4177  .105 Uiso calc R 1 . . H
  H16C  -.2546  .1552  .4895  .105 Uiso calc R 1 . . H
  C17  -.1532(8)  -.2308(2)  .3603(2)  .0423(10) Uani d . 1 . . C
  C18  -.1335(8)  -.3129(3)  .4761(3)  .0671(15) Uani d . 1 . . C
  H18A  -.0456  -.3498  .5027  .101 Uiso calc R 1 . . H
  H18B  -.2478  -.3433  .4634  .101 Uiso calc R 1 . . H
  H18C  -.1638  -.2665  .5106  .101 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
  Br1  .1108(6)  .1028(4)  .0483(2)  -.0569(4)  -.0195(3)  -.0002(3)
  O1  .088(3)  .0558(18)  .0547(18)  .0325(18)  .0157(17)  .0008(15)
  O2  .038(3)  .092(3)  .078(2)  .015(2)  .0069(17)  .0266(19)
  O3  .041(3)  .101(3)  .0596(19)  -.017(2)  -.0155(17)  .0249(18)
  O4  .065(3)  .103(3)  .067(2)  .032(2)  .026(2)  .0431(19)
  O5  .054(2)  .087(2)  .0540(18)  .0143(19)  .0068(16)  .0330(17)
  C1  .033(3)  .073(3)  .0362(19)  -.018(2)  -.0047(17)  .0193(19)
  C2  .066(4)  .060(3)  .0286(18)  -.028(2)  -.008(2)  .0046(17)
  C3  .063(4)  .048(2)  .0274(16)  -.013(2)  -.001(2)  .0023(15)
  C4  .035(3)  .047(2)  .0381(19)  .002(2)  .0006(16)  -.0007(16)
  C4A  .030(3)  .0406(19)  .0314(15)  -.0031(18)  .0000(16)  .0055(14)
  C5  .030(3)  .0357(17)  .0330(16)  -.0013(16)  .0012(15)  .0010(14)
  C6  .036(3)  .0387(19)  .0354(17)  -.0042(19)  -.0061(16)  .0038(15)
  C7  .048(3)  .059(3)  .038(2)  .004(2)  .0033(19)  .0110(19)
  C8  .051(3)  .071(3)  .0339(18)  .013(3)  .0086(18)  .002(2)
  C9  .047(3)  .0394(19)  .0322(16)  .008(2)  .0044(18)  .0005(14)
  C10  .040(3)  .049(2)  .0387(19)  .014(2)  .0067(17)  .0028(17)
  C11  .032(3)  .068(3)  .0398(19)  .007(2)  .0073(17)  .019(2)
  C11A  .034(3)  .051(2)  .0354(19)  -.003(2)  .0009(17)  .0109(17)
  C12  .044(3)  .039(2)  .046(2)  -.0029(19)  -.0098(18)  .0038(17)
  C13  .073(4)  .057(3)  .058(3)  -.001(3)  -.008(3)  .017(2)
  C14  .049(4)  .058(3)  .072(3)  .010(2)  -.005(2)  .010(2)
  C15  .083(4)  .041(2)  .053(2)  .001(3)  -.009(3)  -.0059(18)
  C16  .101(5)  .059(3)  .049(2)  -.009(3)  .008(3)  -.018(2)
  C17  .045(3)  .042(2)  .0395(19)  .003(2)  -.001(2)  .0037(15)
  C18  .071(4)  .082(3)  .049(2)  -.012(3)  -.003(2)  .029(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
  Br1 C2 . 1.902(4) y
  O1 C10 . 1.404(5) y
  O2 C11 . 1.235(5) y
  O3 C1 . 1.364(6) y
  O4 C17 . 1.172(6) y
  O5 C17 . 1.318(5) y
  O5 C18 . 1.462(5) y
  C1 C2 . 1.384(7) ?
  C1 C11A . 1.413(6) ?
  C2 C3 . 1.371(7) ?
  C3 C4 . 1.399(6) ?
  C3 C16 . 1.504(7) ?
  C4 C4A . 1.382(5) ?
  C4A C11A . 1.409(6) ?
  C4A C5 . 1.514(5) ?
  C5 C9 . 1.562(5) y
  C5 C6 . 1.565(5) y
  C6 C7 . 1.526(6) y
  C6 C12 . 1.528(5) y
  C7 C8 . 1.513(6) y
  C8 C9 . 1.575(6) y
  C9 C15 . 1.525(6) y
  C9 C10 . 1.549(5) y
  C10 C11 . 1.527(7) ?
  C10 C17 . 1.549(6) ?
  C11 C11A . 1.453(6) ?
  C12 C13 . 1.527(6) ?
  C12 C14 . 1.532(7) ?