Cu(OAc)2-Mediated Cascade Annulation of Diarylalkyne Sulfonamides through Dual C-N Bond Formation: Synthesis of 5,10-Dihydroindolo[3,2-b]indoles.
Yu, Junchao; Zhang-Negrerie, Daisy; Du, Yunfei; Organic letters 18 (2016) 3322–3325; doi:10.1021/acs.orglett.6b01343

data_1543599
_publ_section_title
;
 Cu(OAc)2-Mediated Cascade Annulation of Diarylalkyne Sulfonamides through
 Dual C-N Bond Formation: Synthesis of 5,10-Dihydroindolo[3,2-b]indoles.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3322
_journal_page_last               3325
_journal_paper_doi               10.1021/acs.orglett.6b01343
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C28 H20 Br Cl N2 O4 S2'
_chemical_formula_weight         627.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90
_cell_angle_beta                 94.174(3)
_cell_angle_gamma                90
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_cell_length_a                   5.4375(8)
_cell_length_b                   10.0119(15)
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_cell_volume                     1223.9(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-2014/8 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0164
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_diffrn_reflns_limit_h_max       6
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_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12047
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.396
_exptl_absorpt_coefficient_mu    2.001
_exptl_absorpt_correction_T_max  0.7952
_exptl_absorpt_correction_T_min  0.6903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.397
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_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+0.7991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0605
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2447
_reflns_number_total             2764
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01343_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' 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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1543599.cif.
;
_cod_database_code               1543599
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_min   0.690
_shelx_estimated_absorpt_t_max   0.795
_shelx_res_checksum              79327
_shelx_hkl_checksum              95095