#------------------------------------------------------------------------------
#$Date: 2017-03-27 21:27:41 +0300 (Mon, 27 Mar 2017) $
#$Revision: 194547 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/75/1507512.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_1507512
loop_
_publ_author_name
'Hu, Yongbo'
'Li, Chaomin'
'Kulkarni, Bheemashankar A.'
'Strobel, Gary'
'Lobkovsky, Emil'
'Torczynski, Richard M.'
'Porco, John A.'
_publ_section_title
;
 Exploring Chemical Diversity of Epoxyquinoid Natural Products: 
 Synthesis and Biological Activity of (−)-Jesterone and Related
 Molecules
;
_journal_issue                   11
_journal_name_full               'Organic Letters'
_journal_page_first              1649
_journal_paper_doi               10.1021/ol0159367
_journal_volume                  3
_journal_year                    2001
_chemical_formula_sum            'C24 H25 Br2 O6'
_chemical_formula_weight         569.46
_chemical_name_systematic
; 
 ? 
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.642(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.8354(10)
_cell_length_b                   9.7459(9)
_cell_length_c                   12.7953(13)
_cell_measurement_temperature    223(2)
_cell_volume                     1225.2(2)
_computing_cell_refinement       SAINT+
_computing_data_collection       SMART
_computing_data_reduction        SAINT+
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker 1K CCD '
_diffrn_measurement_method       '0.3 deg. 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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8044
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    3.347
_exptl_absorpt_correction_T_max  0.5541
_exptl_absorpt_correction_T_min  0.495742
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4610
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.867
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.243
_refine_ls_shift/su_mean         0.021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0448P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                3559
_reflns_number_total             4610
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0159367_s2.cif
_cod_data_source_block           porco7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1715 2011-07-08 13:25:40Z adriana 

2017-03-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H100 Br4 O12'
_cod_original_formula_weight         1188.92
_cod_original_formula_units_Z            1
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1507512
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
Br1 Br 0.26070(4) 0.92741(6) 0.26122(4) 0.05254(16) Uani 1 1 d .
Br2 Br -0.29644(6) 0.13339(5) 0.46807(5) 0.06547(19) Uani 1 1 d .
O1 O -0.0220(3) 0.7164(4) 0.0088(3) 0.0467(8) Uani 1 1 d .
O2 O 0.2483(3) 0.9358(5) 0.0276(2) 0.0629(10) Uani 1 1 d .
O3 O -0.0714(3) 0.7714(3) 0.3627(2) 0.0390(7) Uani 1 1 d .
O4 O -0.2834(4) 0.8307(4) 0.4095(3) 0.0509(9) Uani 1 1 d .
O5 O -0.2122(3) 0.9971(3) 0.1268(3) 0.0421(8) Uani 1 1 d .
O6 O -0.2186(3) 0.7646(3) 0.1721(2) 0.0363(7) Uani 1 1 d .
C1 C 0.1064(4) 0.9008(4) 0.1688(3) 0.0353(10) Uani 1 1 d .
C2 C 0.1394(4) 0.8991(5) 0.0563(3) 0.0403(11) Uani 1 1 d .
C3 C 0.0303(4) 0.8501(5) -0.0191(3) 0.0379(10) Uani 1 1 d .
C4 C -0.1061(4) 0.8342(5) 0.0187(3) 0.0368(10) Uani 1 1 d .
C5 C -0.1413(4) 0.8699(4) 0.1297(3) 0.0339(10) Uani 1 1 d .
C6 C -0.0186(4) 0.8891(4) 0.2051(3) 0.0315(10) Uani 1 1 d .
C7 C -0.0516(5) 0.9059(5) 0.3176(3) 0.0395(10) Uani 1 1 d .
C8 C -0.1967(5) 0.7448(5) 0.3997(3) 0.0383(11) Uani 1 1 d .
C9 C -0.2128(5) 0.5980(4) 0.4226(3) 0.0365(11) Uani 1 1 d .
C10 C -0.3384(5) 0.5549(5) 0.4569(4) 0.0418(12) Uani 1 1 d .
C11 C -0.3640(5) 0.4169(6) 0.4718(3) 0.0444(11) Uani 1 1 d .
C12 C -0.2632(5) 0.3229(5) 0.4533(4) 0.0421(11) Uani 1 1 d .
C13 C -0.1372(5) 0.3647(5) 0.4229(4) 0.0445(13) Uani 1 1 d .
C14 C -0.1120(5) 0.5022(5) 0.4081(4) 0.0414(11) Uani 1 1 d .
C15 C -0.3557(4) 0.9865(5) 0.1473(4) 0.0433(12) Uani 1 1 d .
C16 C -0.4168(5) 0.8700(6) 0.0832(5) 0.0513(14) Uani 1 1 d .
C17 C -0.3451(4) 0.7341(6) 0.1110(4) 0.0451(12) Uani 1 1 d .
C18 C -0.4237(6) 0.6423(9) 0.1814(5) 0.0609(15) Uani 1 1 d .
C19 C -0.4161(6) 1.1250(9) 0.1219(6) 0.0663(16) Uani 1 1 d .
C20 C 0.0547(6) 0.8683(8) -0.1350(4) 0.0523(13) Uani 1 1 d .
C21 C -0.0612(5) 0.8203(6) -0.2047(4) 0.0488(12) Uani 1 1 d .
C22 C -0.1645(5) 0.8939(5) -0.2404(3) 0.0431(11) Uani 1 1 d .
C23 C -0.1850(6) 1.0421(6) -0.2162(5) 0.0617(16) Uani 1 1 d .
H23A H -0.255(3) 1.0511(7) -0.1694(17) 0.093 Uiso 1 1 calc R
H23B H -0.2086(10) 1.0895(18) -0.278(2) 0.093 Uiso 1 1 calc R
H23C H -0.104(3) 1.0785(15) -0.1860(12) 0.093 Uiso 1 1 calc R
C24 C -0.2785(7) 0.8313(7) -0.3110(5) 0.078(2) Uani 1 1 d .
H24A H -0.2697(8) 0.8612(14) -0.380(3) 0.117 Uiso 1 1 calc R
H24B H -0.363(4) 0.8589(13) -0.2875(11) 0.117 Uiso 1 1 calc R
H24C H -0.2723(7) 0.735(4) -0.3086(5) 0.117 Uiso 1 1 calc R
H16B H -0.508(4) 0.867(4) 0.088(3) 0.023(10) Uiso 1 1 d .
H15 H -0.359(4) 0.962(5) 0.217(3) 0.034(12) Uiso 1 1 d .
H14 H -0.034(5) 0.535(5) 0.383(4) 0.038(12) Uiso 1 1 d .
H7B H -0.133(4) 0.953(5) 0.320(3) 0.039(12) Uiso 1 1 d .
H13 H -0.078(5) 0.305(6) 0.411(4) 0.053(16) Uiso 1 1 d .
H7A H 0.023(4) 0.950(5) 0.357(3) 0.028(10) Uiso 1 1 d .
H20B H 0.070(3) 0.950(4) -0.144(3) 0.000(9) Uiso 1 1 d .
H19C H -0.374(5) 1.187(5) 0.163(4) 0.036(14) Uiso 1 1 d .
H11 H -0.450(5) 0.392(6) 0.485(4) 0.061(16) Uiso 1 1 d .
H10 H -0.421(5) 0.615(6) 0.467(4) 0.054(14) Uiso 1 1 d .
H20A H 0.141(6) 0.820(6) -0.147(4) 0.060(15) Uiso 1 1 d .
H19B H -0.507(6) 1.126(7) 0.136(4) 0.067(16) Uiso 1 1 d .
H19A H -0.385(5) 1.163(6) 0.049(5) 0.063(16) Uiso 1 1 d .
H21 H -0.074(5) 0.711(7) -0.222(4) 0.066(15) Uiso 1 1 d .
H4 H -0.184(4) 0.840(4) -0.031(3) 0.026(10) Uiso 1 1 d .
H16A H -0.413(4) 0.881(4) 0.006(4) 0.040(13) Uiso 1 1 d .
H18C H -0.439(4) 0.692(4) 0.232(3) 0.019(11) Uiso 1 1 d .
H18B H -0.522(6) 0.620(7) 0.150(4) 0.078(17) Uiso 1 1 d .
H18A H -0.378(6) 0.553(7) 0.201(5) 0.08(2) Uiso 1 1 d .
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
C4 O1 C3 60.8(3)
C8 O3 C7 116.7(4)
C5 O5 C15 114.4(3)
C5 O6 C17 113.8(3)
C6 C1 C2 125.3(3)
C6 C1 Br1 121.1(3)
C2 C1 Br1 113.6(3)
O2 C2 C1 121.9(4)
O2 C2 C3 121.6(4)
C1 C2 C3 116.5(3)
O1 C3 C4 58.7(3)
O1 C3 C2 112.5(3)
C4 C3 C2 117.9(4)
O1 C3 C20 114.7(4)
C4 C3 C20 121.6(4)
C2 C3 C20 116.9(4)
O1 C4 C3 60.5(3)
O1 C4 C5 115.2(4)
C3 C4 C5 122.7(4)
O6 C5 O5 112.0(3)
O6 C5 C4 110.2(4)
O5 C5 C4 107.9(3)
O6 C5 C6 105.9(3)
O5 C5 C6 106.4(3)
C4 C5 C6 114.4(3)
C1 C6 C7 124.5(4)
C1 C6 C5 120.4(4)
C7 C6 C5 114.9(3)
O3 C7 C6 108.8(4)
O4 C8 O3 123.9(4)
O4 C8 C9 124.9(4)
O3 C8 C9 111.2(4)
C14 C9 C10 119.4(4)
C14 C9 C8 123.1(4)
C10 C9 C8 117.4(4)
C11 C10 C9 120.3(4)
C12 C11 C10 119.1(5)
C13 C12 C11 121.0(5)
C13 C12 Br2 118.7(4)
C11 C12 Br2 120.3(4)
C12 C13 C14 119.8(5)
C9 C14 C13 120.3(5)
O5 C15 C16 108.8(4)
O5 C15 C19 106.0(4)
C16 C15 C19 114.5(5)
C15 C16 C17 110.9(4)
O6 C17 C18 104.3(4)
O6 C17 C16 108.5(4)
C18 C17 C16 114.0(5)
C21 C20 C3 113.3(4)
C22 C21 C20 126.6(5)
C21 C22 C23 124.6(5)
C21 C22 C24 121.5(5)
C23 C22 C24 113.9(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.898(4)
Br2 C12 1.887(5)
O1 C4 1.424(6)
O1 C3 1.452(6)
O2 C2 1.202(5)
O3 C8 1.365(5)
O3 C7 1.449(6)
O4 C8 1.206(6)
O5 C5 1.422(5)
O5 C15 1.452(5)
O6 C5 1.402(5)
O6 C17 1.468(5)
C1 C6 1.339(6)
C1 C2 1.491(6)
C2 C3 1.487(6)
C3 C4 1.455(6)
C3 C20 1.523(7)
C4 C5 1.518(6)
C5 C6 1.521(5)
C6 C7 1.500(6)
C8 C9 1.471(7)
C9 C14 1.380(7)
C9 C10 1.395(7)
C10 C11 1.383(8)
C11 C12 1.378(7)
C12 C13 1.377(7)
C13 C14 1.378(7)
C15 C16 1.509(7)
C15 C19 1.504(9)
C16 C17 1.534(8)
C17 C18 1.508(8)
C20 C21 1.490(8)
C21 C22 1.309(7)
C22 C23 1.493(8)
C22 C24 1.533(7)
