Step-Economical Synthesis of the Marine Ascidian Antibiotics Cadiolide A, B, and D.
Boukouvalas, John; Thibault, Charles; The Journal of organic chemistry 80 (2014) 681–; doi:10.1021/jo502503w

data_4030320
_publ_section_title
;
 Step-Economical Synthesis of the Marine Ascidian Antibiotics Cadiolide A,
 B, and D.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              681
_journal_paper_doi               10.1021/jo502503w
_journal_volume                  80
_journal_year                    2014
_chemical_formula_moiety         'C24 H12 Br4 O6, 2(H2 O)'
_chemical_formula_sum            'C24 H16 Br4 O8'
_chemical_formula_weight         752.01
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 99.394(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.574(3)
_cell_length_b                   13.462(4)
_cell_length_c                   21.063(6)
_cell_measurement_reflns_used    3295
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      22.68
_cell_measurement_theta_min      2.48
_cell_volume                     2398.6(13)
_computing_cell_refinement       'APEX 2 (Bruker, 2005b)'
_computing_data_collection       'APEX 2 (Bruker, 2005b)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEX II CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23445
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    6.762
_exptl_absorpt_correction_T_max  0.7737
_exptl_absorpt_correction_T_min  0.3178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.082
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         4213
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_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                2762
_reflns_number_total             4213
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502503w_si_003.cif
_cod_data_source_block           jbk003
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030320.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4030320