Intermolecular oxidative dehydrogenative 3,3′-coupling of benzo[b]furans and benzo[b]thiophenes promoted by DDQ/H+: total synthesis of shandougenine B
Wirtanen, T.; Muuronen, M.; Hurmalainen, J.; Tuononen, H. M.; Nieger, M.; Helaja, J.; Organic Chemistry Frontiers 3 (2016) 1738–; doi:10.1039/C6QO00331A

data_1553495
_publ_section_title
;
 Intermolecular oxidative dehydrogenative 3,3&#x2032;-coupling of
 benzo[b]furans and benzo[b]thiophenes promoted by DDQ/H+: total synthesis
 of shandougenine B
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1738
_journal_paper_doi               10.1039/C6QO00331A
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         '2(C15 H12 O2), C8 Cl2 N2 O2'
_chemical_formula_sum            'C38 H24 Cl2 N2 O6'
_chemical_formula_weight         675.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-05-02 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.3580(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2296(4)
_cell_length_b                   6.2823(2)
_cell_length_c                   33.8457(10)
_cell_measurement_reflns_used    9136
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.16
_cell_measurement_theta_min      2.61
_cell_volume                     3025.56(16)
_computing_cell_refinement       SAINT
_computing_data_collection       APEX2
_computing_data_reduction        SAINT
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture with Photon100 detector'
_diffrn_measurement_method       'rotation in \f and \w, 0.5\%, shutterless'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            30717
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.174
_diffrn_reflns_theta_min         2.611
_diffrn_source                   'I\mS microfocus'
_exptl_absorpt_coefficient_mu    2.391
_exptl_absorpt_correction_T_max  0.8644
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2015)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       plates
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+3.4200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1571
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5279
_reflns_number_total             5937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00331a2.cif
_cod_data_source_block           mnhy056
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1553495
_shelx_estimated_absorpt_t_min   0.480
_shelx_estimated_absorpt_t_max   0.870
_shelxl_version_number           2014-3
_shelx_res_checksum              20623
_shelx_hkl_checksum              75694