#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/87/1508726.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_1508726
loop_
_publ_author_name
'Feldman, Ken S.'
'Selfridge, Brandon R.'
_publ_section_title
;
 Enantioselective synthesis of the ent-lomaiviticin A bicyclic core.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5484
_journal_page_last               5487
_journal_paper_doi               10.1021/ol302567f
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C46 H54 O6'
_chemical_formula_sum            'C48 H54 O6'
_chemical_formula_weight         726.91
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.966(2)
_cell_length_b                   8.966(2)
_cell_length_c                   53.26(2)
_cell_measurement_reflns_used    1195
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      15.811
_cell_measurement_theta_min      1.886
_cell_volume                     4282(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0795
_diffrn_reflns_av_sigmaI/netI    0.1063
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       71
_diffrn_reflns_limit_l_min       -71
_diffrn_reflns_number            21947
_diffrn_reflns_theta_full        28.42
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pyramid
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         5331
_refine_ls_number_restraints     232
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.2779
_refine_ls_R_factor_gt           0.1400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3556
_refine_ls_wR_factor_ref         0.4275
_reflns_number_gt                1917
_reflns_number_total             5331
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302567f_si_003.cif
_cod_data_source_block           brs9s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P4(3)2(1)2
_cod_database_code               1508726
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'
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
C1 C 0.9221(15) 0.7200(14) 0.3682(2) 0.208(6) Uani 1 1 d U
H1A H 0.9946 0.6413 0.3676 0.312 Uiso 1 1 calc R
H1B H 0.9487 0.7961 0.3563 0.312 Uiso 1 1 calc R
H1C H 0.8256 0.6807 0.3640 0.312 Uiso 1 1 calc R
C2 C 0.8587(17) 0.7020(13) 0.4114(2) 0.179(4) Uani 1 1 d U
C3 C 0.9092(16) 0.7552(14) 0.4349(2) 0.197(5) Uani 1 1 d U
H3 H 0.9777 0.8327 0.4361 0.237 Uiso 1 1 calc R
C4 C 0.8503(14) 0.6844(14) 0.45634(19) 0.180(4) Uani 1 1 d U
H4 H 0.8631 0.7271 0.4721 0.216 Uiso 1 1 calc R
C5 C 0.7702(7) 0.5462(9) 0.45382(11) 0.0995(18) Uani 1 1 d U
C6 C 0.7540(13) 0.4883(11) 0.43027(15) 0.165(4) Uani 1 1 d U
H6 H 0.7016 0.3999 0.4279 0.198 Uiso 1 1 calc R
C7 C 0.8191(13) 0.5657(13) 0.40871(15) 0.155(3) Uani 1 1 d U
H7 H 0.8314 0.5170 0.3934 0.186 Uiso 1 1 calc R
C8 C 0.7291(7) 0.4602(9) 0.47613(12) 0.1022(19) Uani 1 1 d U
H8A H 0.8176 0.4138 0.4831 0.123 Uiso 1 1 calc R
H8B H 0.6884 0.5269 0.4887 0.123 Uiso 1 1 calc R
C9 C 0.5623(6) 0.2615(6) 0.49061(9) 0.0781(14) Uani 1 1 d U
C21 C 0.4867(9) 0.1263(8) 0.47854(12) 0.0998(19) Uani 1 1 d U
C22 C 0.5082(10) 0.1029(8) 0.45015(11) 0.123(3) Uani 1 1 d U
H22A H 0.4715 0.1900 0.4413 0.148 Uiso 1 1 calc R
H22B H 0.6139 0.0934 0.4466 0.148 Uiso 1 1 calc R
C23 C 0.4273(17) -0.0350(12) 0.44051(16) 0.180(5) Uani 1 1 d U
H23 H 0.3241 -0.0295 0.4420 0.216 Uiso 1 1 calc R
C19 C 0.6875(10) 0.1922(9) 0.50751(12) 0.122(2) Uani 1 1 d U
H19A H 0.7388 0.2720 0.5163 0.147 Uiso 1 1 calc R
H19B H 0.6414 0.1287 0.5200 0.147 Uiso 1 1 calc R
C20 C 0.8019(10) 0.1007(12) 0.49284(15) 0.163(4) Uani 1 1 d U
H20A H 0.7517 0.0417 0.4804 0.244 Uiso 1 1 calc R
H20B H 0.8547 0.0362 0.5042 0.244 Uiso 1 1 calc R
H20C H 0.8713 0.1666 0.4848 0.244 Uiso 1 1 calc R
C10 C 0.4548(7) 0.3509(5) 0.50774(8) 0.0691(13) Uani 1 1 d U
H10 H 0.5192 0.4185 0.5173 0.083 Uiso 1 1 calc R
C11 C 0.3791(7) 0.2606(6) 0.52666(8) 0.0771(15) Uani 1 1 d U
H11 H 0.3046 0.1965 0.5211 0.093 Uiso 1 1 calc R
C12 C 0.4071(9) 0.2617(7) 0.55110(9) 0.103(2) Uani 1 1 d U
H12 H 0.4861 0.3226 0.5558 0.124 Uiso 1 1 calc R
C13 C 0.3374(12) 0.1864(9) 0.57106(10) 0.124(3) Uani 1 1 d U
C14 C 0.3852(16) 0.2053(13) 0.59557(11) 0.184(4) Uani 1 1 d U
H14 H 0.4670 0.2680 0.5975 0.221 Uiso 1 1 calc R
C15 C 0.334(2) 0.1492(19) 0.61608(18) 0.247(6) Uani 1 1 d U
H15 H 0.3725 0.1714 0.6318 0.297 Uiso 1 1 calc R
C16 C 0.211(2) 0.0498(16) 0.6124(2) 0.239(6) Uani 1 1 d U
H16 H 0.1628 0.0078 0.6261 0.286 Uiso 1 1 calc R
C17 C 0.163(2) 0.0156(13) 0.5880(2) 0.244(6) Uani 1 1 d U
H17 H 0.0916 -0.0578 0.5855 0.293 Uiso 1 1 calc R
C18 C 0.2223(15) 0.0899(13) 0.56753(16) 0.178(4) Uani 1 1 d U
H18 H 0.1837 0.0741 0.5515 0.214 Uiso 1 1 calc R
O1 O 0.6227(4) 0.3486(5) 0.47039(6) 0.0850(12) Uani 1 1 d U
O2 O 0.9181(16) 0.7822(10) 0.39273(17) 0.268(5) Uani 1 1 d U
O3 O 0.4139(7) 0.0419(5) 0.49019(8) 0.1185(17) Uani 1 1 d U
C24 C 0.467(2) -0.1404(14) 0.4321(2) 0.233(7) Uani 1 1 d U
H24A H 0.5688 -0.1563 0.4299 0.280 Uiso 1 1 calc R
H24B H 0.3991 -0.2132 0.4273 0.280 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 C1 H1A 109.5 . .
O2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
O2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C7 C2 O2 122.8(11) . .
C7 C2 C3 120.5(11) . .
O2 C2 C3 110.4(13) . .
C4 C3 C2 116.5(12) . .
C4 C3 H3 121.7 . .
C2 C3 H3 121.7 . .
C3 C4 C5 119.9(9) . .
C3 C4 H4 120.0 . .
C5 C4 H4 120.0 . .
C6 C5 C4 117.8(8) . .
C6 C5 C8 121.3(7) . .
C4 C5 C8 120.2(7) . .
C5 C6 C7 119.9(9) . .
C5 C6 H6 120.0 . .
C7 C6 H6 120.0 . .
C2 C7 C6 118.5(9) . .
C2 C7 H7 120.8 . .
C6 C7 H7 120.8 . .
O1 C8 C5 111.5(5) . .
O1 C8 H8A 109.3 . .
C5 C8 H8A 109.3 . .
O1 C8 H8B 109.3 . .
C5 C8 H8B 109.3 . .
H8A C8 H8B 108.0 . .
O1 C9 C21 106.4(4) . .
O1 C9 C10 113.3(4) . .
C21 C9 C10 112.4(5) . .
O1 C9 C19 112.1(5) . .
C21 C9 C19 104.1(5) . .
C10 C9 C19 108.2(4) . .
O3 C21 C9 122.2(6) . .
O3 C21 C22 120.0(6) . .
C9 C21 C22 117.7(6) . .
C23 C22 C21 112.5(7) . .
C23 C22 H22A 109.1 . .
C21 C22 H22A 109.1 . .
C23 C22 H22B 109.1 . .
C21 C22 H22B 109.1 . .
H22A C22 H22B 107.8 . .
C24 C23 C22 132.6(17) . .
C24 C23 H23 113.7 . .
C22 C23 H23 113.7 . .
C20 C19 C9 113.6(5) . .
C20 C19 H19A 108.8 . .
C9 C19 H19A 108.8 . .
C20 C19 H19B 108.8 . .
C9 C19 H19B 108.8 . .
H19A C19 H19B 107.7 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C11 C10 C9 114.1(4) . .
C11 C10 C10 114.8(4) . 7_556
C9 C10 C10 111.7(4) . 7_556
C11 C10 H10 105.0 . .
C9 C10 H10 105.0 . .
C10 C10 H10 105.0 7_556 .
C12 C11 C10 125.8(6) . .
C12 C11 H11 117.1 . .
C10 C11 H11 117.1 . .
C11 C12 C13 130.9(8) . .
C11 C12 H12 114.5 . .
C13 C12 H12 114.5 . .
C18 C13 C14 116.3(9) . .
C18 C13 C12 122.6(7) . .
C14 C13 C12 121.1(10) . .
C15 C14 C13 129.8(14) . .
C15 C14 H14 115.1 . .
C13 C14 H14 115.1 . .
C14 C15 C16 113.7(13) . .
C14 C15 H15 123.2 . .
C16 C15 H15 123.2 . .
C17 C16 C15 120.0(10) . .
C17 C16 H16 120.0 . .
C15 C16 H16 120.0 . .
C18 C17 C16 120.6(14) . .
C18 C17 H17 119.7 . .
C16 C17 H17 119.7 . .
C13 C18 C17 119.2(11) . .
C13 C18 H18 120.4 . .
C17 C18 H18 120.4 . .
C8 O1 C9 118.4(4) . .
C2 O2 C1 118.8(10) . .
C23 C24 H24A 120.0 . .
C23 C24 H24B 120.0 . .
H24A C24 H24B 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.422(13) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C7 1.281(14) .
C2 O2 1.336(12) .
C2 C3 1.414(14) .
C3 C4 1.411(13) .
C3 H3 0.9300 .
C4 C5 1.439(13) .
C4 H4 0.9300 .
C5 C6 1.365(10) .
C5 C8 1.464(9) .
C6 C7 1.463(12) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 O1 1.416(8) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 O1 1.437(6) .
C9 C21 1.531(9) .
C9 C10 1.550(7) .
C9 C19 1.567(8) .
C21 O3 1.176(8) .
C21 C22 1.538(9) .
C22 C23 1.523(13) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 C24 1.105(13) .
C23 H23 0.9300 .
C19 C20 1.529(11) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C10 C11 1.460(7) .
C10 C10 1.554(10) 7_556
C10 H10 0.9800 .
C11 C12 1.326(6) .
C11 H11 0.9300 .
C12 C13 1.406(10) .
C12 H12 0.9300 .
C13 C18 1.359(14) .
C13 C14 1.384(10) .
C14 C15 1.289(14) .
C14 H14 0.9300 .
C15 C16 1.43(2) .
C15 H15 0.9300 .
C16 C17 1.40(2) .
C16 H16 0.9300 .
C17 C18 1.381(12) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C24 H24A 0.9300 .
C24 H24B 0.9300 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C7 C2 C3 C4 -30(2) . .
O2 C2 C3 C4 177.4(12) . .
C2 C3 C4 C5 13.1(19) . .
C3 C4 C5 C6 -0.2(16) . .
C3 C4 C5 C8 170.4(10) . .
C4 C5 C6 C7 0.9(14) . .
C8 C5 C6 C7 -169.5(8) . .
O2 C2 C7 C6 -179.5(13) . .
C3 C2 C7 C6 31(2) . .
C5 C6 C7 C2 -16.4(17) . .
C6 C5 C8 O1 -23.6(10) . .
C4 C5 C8 O1 166.2(7) . .
O1 C9 C21 O3 -172.2(6) . .
C10 C9 C21 O3 -47.7(8) . .
C19 C9 C21 O3 69.2(8) . .
O1 C9 C21 C22 7.6(7) . .
C10 C9 C21 C22 132.2(6) . .
C19 C9 C21 C22 -111.0(7) . .
O3 C21 C22 C23 -0.1(11) . .
C9 C21 C22 C23 -179.9(8) . .
C21 C22 C23 C24 -115.8(14) . .
O1 C9 C19 C20 -54.3(9) . .
C21 C9 C19 C20 60.3(9) . .
C10 C9 C19 C20 -179.9(7) . .
O1 C9 C10 C11 173.4(4) . .
C21 C9 C10 C11 52.7(6) . .
C19 C9 C10 C11 -61.7(7) . .
O1 C9 C10 C10 41.0(5) . 7_556
C21 C9 C10 C10 -79.6(4) . 7_556
C19 C9 C10 C10 165.9(4) . 7_556
C9 C10 C11 C12 107.7(6) . .
C10 C10 C11 C12 -121.5(6) 7_556 .
C10 C11 C12 C13 176.3(7) . .
C11 C12 C13 C18 1.7(14) . .
C11 C12 C13 C14 -179.5(8) . .
C18 C13 C14 C15 -2.9(18) . .
C12 C13 C14 C15 178.2(13) . .
C13 C14 C15 C16 2(2) . .
C14 C15 C16 C17 3(2) . .
C15 C16 C17 C18 -7(2) . .
C14 C13 C18 C17 -1.4(15) . .
C12 C13 C18 C17 177.5(10) . .
C16 C17 C18 C13 6(2) . .
C5 C8 O1 C9 -175.4(5) . .
C21 C9 O1 C8 -164.8(5) . .
C10 C9 O1 C8 71.1(6) . .
C19 C9 O1 C8 -51.6(6) . .
C7 C2 O2 C1 7(2) . .
C3 C2 O2 C1 159.7(12) . .
