Copper-Mediated Selective Mono- and Sequential Organochalcogenation of C-H Bonds: Synthesis of Hybrid Unsymmetrical Aryl Ferrocene Chalcogenides.
Sattar, Moh; Patidar, Krishna; Thorat, Raviraj Ananda; Kumar, Sangit; The Journal of organic chemistry 84 (2019) 6669–6678; doi:10.1021/acs.joc.9b00311

data_4034599
_publ_section_title
;
 Copper-Mediated Selective Mono- and Sequential Organochalcogenation of
 C-H Bonds: Synthesis of Hybrid Unsymmetrical Aryl Ferrocene
 Chalcogenides.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6669
_journal_page_last               6678
_journal_paper_doi               10.1021/acs.joc.9b00311
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C37.5 H29 Cl Fe N2 O2 S Se'
_chemical_formula_weight         741.44
_space_group_crystal_system      triclinic
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_space_group_name_Hall           '-P 1'
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_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
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_cell_angle_beta                 94.472(2)
_cell_angle_gamma                94.362(2)
_cell_formula_units_Z            4
_cell_length_a                   10.1429(5)
_cell_length_b                   11.3255(6)
_cell_length_c                   28.5157(15)
_cell_measurement_reflns_used    9074
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      2.56
_cell_volume                     3189.3(3)
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_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1002
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.798
_diffrn_reflns_theta_min         2.194
_exptl_absorpt_coefficient_mu    1.801
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             1506
_exptl_crystal_size_max          0.7
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_refine_diff_density_max         1.058
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     816
_refine_ls_number_reflns         12253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0258P)^2^+7.6616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8419
_reflns_number_total             12253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00311_si_004.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;

2020-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C75 H57 Cl2 Fe2 N4 O4 S2 Se2'
_cod_original_formula_weight         1482.88
_cod_original_formula_units_Z            2
_cod_database_code               4034599
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              50123
_shelx_hkl_checksum              70612