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#$Date: 2016-03-22 11:56:50 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178925 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/54/4115422.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4115422
loop_
_publ_author_name
'Sergey N. Fedorov'
'Oleg S. Radchenko'
'Larisa K. Shubina'
'Anatoly I. Kalinovsky'
'Andrey V. Gerasimenko'
'Dmitry Y. Popov'
'Valentin A. Stonik'
_publ_section_title
;
 Aplydactone, a New Sesquiterpenoid with an Unprecedented Carbon Skeleton
 from the Sea Hare Aplysia dactylomela, and Its Cargill-Like Rearrangement
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              504
_journal_page_last               505
_journal_paper_doi               10.1021/ja003254t
_journal_volume                  123
_journal_year                    2001
_chemical_formula_moiety         C15H21BrO
_chemical_formula_sum            'C15 H21 Br O'
_chemical_formula_weight         297.23
_chemical_melting_point          468(1)
_chemical_name_common            aplydactone
_chemical_name_systematic
; 
 (1R,3S,6S,8R,11S)-8-bromo-3,7,7-trimethyltetracyclo[4.4.2.01,6.03,11]
  dodecan-4-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.202(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.1894(11)
_cell_length_b                   12.3968(19)
_cell_length_c                   7.6376(11)
_cell_measurement_reflns_used    698
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.4
_cell_measurement_theta_min      5.3
_cell_volume                     679.64(18)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1998)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL/PC (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker SMART CCD area detector diffractometer'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3199
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    3.007
_exptl_absorpt_correction_T_max  0.801
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       'Transparent crystals'
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.064(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1837
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.610
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0425P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0670
_reflns_number_gt                1737
_reflns_number_total             1837
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja003254t.cif
_cod_data_source_block           tibox01j
_cod_database_code               4115422
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br Br 0.77414(5) 0.23330(4) 0.47844(5) 0.05743(16) Uani 1 1 d .
O O -0.1204(4) -0.0984(3) 0.2027(4) 0.0700(9) Uani 1 1 d .
C10 C 0.4142(6) 0.1992(3) 0.0230(5) 0.0477(10) Uani 1 1 d .
H10A H 0.3538 0.2554 -0.0477 0.057 Uiso 1 1 calc R
H10B H 0.5021 0.1632 -0.0491 0.057 Uiso 1 1 calc R
C9 C 0.5231(5) 0.2523(3) 0.1781(5) 0.0460(10) Uani 1 1 d .
H9A H 0.6291 0.2912 0.1368 0.055 Uiso 1 1 calc R
H9B H 0.4438 0.3032 0.2351 0.055 Uiso 1 1 calc R
C8 C 0.5891(5) 0.1658(3) 0.3069(5) 0.0382(9) Uani 1 1 d .
H8 H 0.6554 0.1114 0.2413 0.046 Uiso 1 1 calc R
C7 C 0.4344(5) 0.1082(3) 0.3975(4) 0.0355(8) Uani 1 1 d .
C6 C 0.3044(5) 0.0555(3) 0.2536(4) 0.0297(7) Uani 1 1 d .
C5 C 0.1184(5) 0.0187(3) 0.3219(5) 0.0402(9) Uani 1 1 d .
H5A H 0.1410 -0.0327 0.4164 0.048 Uiso 1 1 calc R
H5B H 0.0535 0.0802 0.3679 0.048 Uiso 1 1 calc R
C4 C -0.0006(6) -0.0327(3) 0.1765(6) 0.0438(10) Uani 1 1 d .
C3 C 0.0426(6) 0.0083(3) 0.0007(6) 0.0462(10) Uani 1 1 d .
C2 C 0.0612(6) 0.1342(3) 0.0171(5) 0.0485(10) Uani 1 1 d .
H2A H 0.0388 0.1723 -0.0930 0.058 Uiso 1 1 calc R
H2B H -0.0105 0.1653 0.1084 0.058 Uiso 1 1 calc R
C1 C 0.2683(5) 0.1184(3) 0.0707(4) 0.0354(8) Uani 1 1 d .
C11 C 0.2621(5) 0.0047(3) -0.0133(5) 0.0402(9) Uani 1 1 d .
H11 H 0.3111 -0.0040 -0.1296 0.048 Uiso 1 1 calc R
C12 C 0.3752(5) -0.0417(3) 0.1454(4) 0.0368(8) Uani 1 1 d .
H12A H 0.5087 -0.0420 0.1329 0.044 Uiso 1 1 calc R
H12B H 0.3318 -0.1114 0.1837 0.044 Uiso 1 1 calc R
C13 C -0.0750(8) -0.0384(4) -0.1514(7) 0.0715(16) Uani 1 1 d .
H13A H -0.0645 -0.1156 -0.1501 0.107 Uiso 1 1 calc R
H13B H -0.0322 -0.0110 -0.2596 0.107 Uiso 1 1 calc R
H13C H -0.2028 -0.0183 -0.1410 0.107 Uiso 1 1 calc R
C14 C 0.3267(6) 0.1881(3) 0.5074(5) 0.0522(10) Uani 1 1 d .
H14A H 0.4131 0.2299 0.5799 0.078 Uiso 1 1 calc R
H14B H 0.2454 0.1491 0.5802 0.078 Uiso 1 1 calc R
H14C H 0.2543 0.2354 0.4309 0.078 Uiso 1 1 calc R
C15 C 0.5167(7) 0.0187(3) 0.5171(6) 0.0527(11) Uani 1 1 d .
H15A H 0.6001 -0.0247 0.4530 0.079 Uiso 1 1 calc R
H15B H 0.4179 -0.0256 0.5566 0.079 Uiso 1 1 calc R
H15C H 0.5837 0.0505 0.6164 0.079 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 C10 C9 115.5(3)
C8 C9 C10 109.1(3)
C9 C8 C7 114.7(3)
C9 C8 Br 107.6(2)
C7 C8 Br 112.1(2)
C8 C7 C15 110.1(3)
C8 C7 C14 110.5(3)
C15 C7 C14 109.3(3)
C8 C7 C6 107.6(3)
C15 C7 C6 108.4(3)
C14 C7 C6 110.9(3)
C5 C6 C7 112.9(3)
C5 C6 C12 105.4(3)
C7 C6 C12 120.0(3)
C5 C6 C1 109.8(3)
C7 C6 C1 118.3(3)
C12 C6 C1 87.5(2)
C4 C5 C6 110.3(3)
O C4 C3 124.5(4)
O C4 C5 122.9(4)
C3 C4 C5 112.5(3)
C4 C3 C13 115.3(3)
C4 C3 C2 106.8(3)
C13 C3 C2 118.9(4)
C4 C3 C11 108.0(3)
C13 C3 C11 116.9(4)
C2 C3 C11 87.3(3)
C1 C2 C3 88.3(3)
C10 C1 C2 121.8(3)
C10 C1 C11 120.6(3)
C2 C1 C11 90.0(3)
C10 C1 C6 116.8(3)
C2 C1 C6 113.6(3)
C11 C1 C6 85.3(2)
C12 C11 C1 90.7(3)
C12 C11 C3 116.3(3)
C1 C11 C3 87.3(3)
C11 C12 C6 87.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C8 1.998(3)
O C4 1.210(5)
C10 C1 1.509(5)
C10 C9 1.531(5)
C9 C8 1.513(5)
C8 C7 1.520(5)
C7 C15 1.534(5)
C7 C14 1.536(5)
C7 C6 1.547(5)
C6 C5 1.532(5)
C6 C12 1.563(5)
C6 C1 1.608(5)
C5 C4 1.504(5)
C4 C3 1.485(6)
C3 C13 1.513(6)
C3 C2 1.571(5)
C3 C11 1.588(5)
C2 C1 1.535(5)
C1 C11 1.547(5)
C11 C12 1.533(5)
