Photoredox-Catalyzed C-H Arylation of Internal Alkenes to Tetrasubstituted Alkenes: Synthesis of Tamoxifen.
Wang, Quannan; Yang, Xiaoge; Wu, Ping; Yu, Zhengkun; Organic letters 19 (2017) 6248–6251; doi:10.1021/acs.orglett.7b03223

data_1548611
_publ_section_title
;
 Photoredox-Catalyzed C-H Arylation of Internal Alkenes to
 Tetrasubstituted Alkenes: Synthesis of Tamoxifen.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6248
_journal_page_last               6251
_journal_paper_doi               10.1021/acs.orglett.7b03223
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C17 H13 N3 O3 S2'
_chemical_formula_weight         371.42
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 94.419(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.0165(7)
_cell_length_b                   23.916(3)
_cell_length_c                   17.104(2)
_cell_measurement_reflns_used    2308
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.747
_cell_measurement_theta_min      4.170
_cell_volume                     1638.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
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_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7687
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
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_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             768
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_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
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_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+1.4637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1751
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_reflns_number_gt                2346
_reflns_number_total             3027
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b03223_si_002.cif
_cod_data_source_block           for_4e_(yxg1494)
_cod_database_code               1548611
_shelx_estimated_absorpt_t_min   0.927
_shelx_estimated_absorpt_t_max   0.956
_shelxl_version_number           2013-4
_shelx_res_checksum              30880
_shelx_hkl_checksum              1266