Remarkable switch of regioselectivity in diels-alder reaction: divergent total synthesis of borreverine, caulindoles, and flinderoles.
Dethe, Dattatraya H.; Erande, Rohan D.; Dherange, Balu D.; Organic letters 16 (2014) 2764–2767; doi:10.1021/ol501078d

data_1515984
_publ_section_title
;
 Remarkable switch of regioselectivity in diels-alder reaction: divergent
 total synthesis of borreverine, caulindoles, and flinderoles.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2764
_journal_page_last               2767
_journal_paper_doi               10.1021/ol501078d
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C40 H38 N2 O4 S2, 4(H2O)'
_chemical_formula_sum            'C40 H46 N2 O8 S2'
_chemical_formula_weight         746.93
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.124(5)
_cell_length_b                   8.811(5)
_cell_length_c                   29.171(5)
_cell_measurement_reflns_used    4343
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.96
_cell_measurement_theta_min      2.51
_cell_volume                     7486(5)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6974
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3168
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.084
_platon_squeeze_details
;
 PLATON/SQUEEZE estimated the solvent-accessible
 region to contain 324 (80+80+82+82) electrons per unit cell. This amounts to 
 nearly 40 electrons per formula unit (Z=8). The electron densities are 
 tentatively modelled as to four H2O molecules per formula unit. 
 These water molecules are included in the formula sum for the 
 calculation of the intensive properties.
;
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         6974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.850
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0705
_refine_ls_shift/su_max          0.073
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1409P)^2^+4.1736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1802
_refine_ls_wR_factor_ref         0.2061
_reflns_number_gt                4303
_reflns_number_total             6974
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501078d_si_010.cif
_cod_data_source_block           ortho
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1515980--1515987.cif.
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1515984