Transition-Metal-Free Diarylannulated Sulfide and Selenide Construction via Radical/Anion-Mediated Sulfur-Iodine and Selenium-Iodine Exchange.
Wang, Ming; Fan, Qiaoling; Jiang, Xuefeng; Organic letters 18 (2016) 5756–5759; doi:10.1021/acs.orglett.6b03078

data_1544366
_publ_section_title
;
 Transition-Metal-Free Diarylannulated Sulfide and Selenide Construction
 via Radical/Anion-Mediated Sulfur-Iodine and Selenium-Iodine Exchange.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5756
_journal_page_last               5759
_journal_paper_doi               10.1021/acs.orglett.6b03078
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C26 H19 I'
_chemical_formula_sum            'C26 H19 I'
_chemical_formula_weight         458.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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
_audit_creation_date             2016-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.0575(12)
_cell_length_b                   11.4137(9)
_cell_length_c                   21.6746(17)
_cell_measurement_reflns_used    5578
_cell_measurement_temperature    130
_cell_measurement_theta_max      24.422
_cell_measurement_theta_min      2.27
_cell_volume                     3972.4(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26260
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.879
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.619
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0587 before and 0.0502 after correction.
The Ratio of minimum to maximum transmission is 0.9129.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.103
_refine_diff_density_min         -1.496
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3694
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.202
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+17.7696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3170
_reflns_number_total             3694
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03078_si_003.cif
_cod_data_source_block           dm16386
_cod_depositor_comments
'Adding full bibliography for 1544365--1544366.cif.'
_cod_database_code               1544366
_shelx_estimated_absorpt_t_max   0.793
_shelx_estimated_absorpt_t_min   0.688
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C27 \\sim C28 \\sim C29 \\sim C30 \\sim C23 \\sim C32: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C28) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C28) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C28) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3. Others
 Fixed Sof: I1(0.6) I2(0.4) C21(0.6) C22(0.6) C23(0.6) H23(0.6) C24(0.6)
 H24(0.6) C25(0.6) H25(0.6) C26(0.6) H26(0.6) C27(0.4) C28(0.4) H28(0.4)
 C29(0.4) H29(0.4) C30(0.4) H30(0.4) C31(0.4) H31(0.4) C32(0.4)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C5(H5), C18(H18), C3(H3), C4(H4), C14(H14), C2(H2), C8(H8),
 C13(H13), C16(H16), C17(H17), C11(H11), C12(H12), C19(H19), C23(H23), C24(H24),
  C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31)
4.b Fitted hexagon refined as free rotating group:
 C21(C22,C23,C24,C25,C26), C27(C28,C29,C30,C31,C32)
;
_shelx_res_checksum              58859
_shelx_hkl_checksum              39619
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'