Regioselective copper-catalyzed direct arylation of benzodithiophene-S,S-tetraoxide.
Khambhati, D. P.; Sachinthani, K. A. N.; Rheingold, A. L.; Nelson, T. L.; Chemical communications (Cambridge, England) 53 (2017) 5107–5109; doi:10.1039/c7cc01781b

data_7119934
_publ_section_title
;
 Regioselective copper-catalyzed direct arylation of
 benzodithiophene-S,S-tetraoxide.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5107
_journal_page_last               5109
_journal_paper_doi               10.1039/c7cc01781b
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C46 H62 O6 S2'
_chemical_formula_sum            'C46 H62 O6 S2'
_chemical_formula_weight         775.07
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-01
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_audit_update_record
;
2017-03-07 deposited with the CCDC.
2017-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.5930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.9364(3)
_cell_length_b                   7.6637(2)
_cell_length_c                   18.4671(4)
_cell_measurement_reflns_used    7833
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.61
_cell_measurement_theta_min      2.985
_cell_volume                     2095.36(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17378
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.609
_diffrn_reflns_theta_min         2.985
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.521
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0853 before and 0.0641 after correction.
The Ratio of minimum to maximum transmission is 0.8019.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       plate
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0404P)^2^+1.1774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3356
_reflns_number_total             3784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc01781b2.cif
_cod_data_source_block           nelson12_0m_a
_cod_depositor_comments          'Adding full bibliography for 7119934.cif.'
_cod_database_code               7119934
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.658
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C8(H8A,H8B), C10(H10A,H10B), C6(H6A,H6B),
 C7(H7A,H7B), C5(H5A,H5B), C9(H9A,H9B), C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C23(H23), C21(H21), C20(H20), C22(H22)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'