Highly efficient and stereocontrolled oxidative coupling of tetrahydropyrroloindoles: synthesis of chimonanthines, (+)-WIN 64821 and (+)-WIN 64745
Sun, Deqian; Xing, Changyu; Wang, Xiaoqing; Su, Zhongquan; Li, Chaozhong; Org. Chem. Front. 1 (2014) 956–; doi:10.1039/C4QO00165F

data_1553020
_publ_section_title
;
 Highly efficient and stereocontrolled oxidative coupling of
 tetrahydropyrroloindoles: synthesis of chimonanthines, (+)-WIN 64821 and
 (+)-WIN 64745
;
_journal_issue                   8
_journal_name_full               'Org. Chem. Front.'
_journal_page_first              956
_journal_paper_doi               10.1039/C4QO00165F
_journal_volume                  1
_journal_year                    2014
_chemical_formula_sum            'C34 H28 Cl4 N6 O8 S2'
_chemical_formula_weight         854.54
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.383(2)
_cell_angle_beta                 69.786(2)
_cell_angle_gamma                66.9080(10)
_cell_formula_units_Z            2
_cell_length_a                   11.2563(3)
_cell_length_b                   13.0650(3)
_cell_length_c                   14.4176(4)
_cell_measurement_reflns_used    4162
_cell_measurement_temperature    132(2)
_cell_measurement_theta_max      65.51
_cell_measurement_theta_min      4.57
_cell_volume                     1820.34(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      132(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11661
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         65.00
_diffrn_reflns_theta_min         4.57
_exptl_absorpt_coefficient_mu    4.554
_exptl_absorpt_correction_T_max  0.9144
_exptl_absorpt_correction_T_min  0.5483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         5898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0838P)^2^+0.4413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1399
_reflns_number_gt                5060
_reflns_number_total             5898
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4qo00165f2.cif
_cod_data_source_block           cu_dm11686_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1820.34(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1553020