Sequential Carbon-Carbon/Carbon-Selenium Bond Formation Mediated by Iron(III) Chloride and Diorganyl Diselenides: Synthesis and Reactivity of 2-Organoselenyl-Naphthalenes.
Recchi, Ana M. S.; Back, Davi F.; Zeni, Gilson; The Journal of organic chemistry 82 (2017) 2713–2723; doi:10.1021/acs.joc.7b00050

data_4032201
_publ_section_title
;
 Sequential Carbon-Carbon/Carbon-Selenium Bond Formation Mediated by
 Iron(III) Chloride and Diorganyl Diselenides: Synthesis and Reactivity of
 2-Organoselenyl-Naphthalenes.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2713
_journal_page_last               2723
_journal_paper_doi               10.1021/acs.joc.7b00050
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C22 H16 Se'
_chemical_formula_sum            'C22 H16 Se'
_chemical_formula_weight         359.31
_chemical_melting_point          373.5
_chemical_name_common            phenyl(1-phenylnaphtalen-2-yl)selane
_chemical_name_systematic
;
 phenyl(1-phenylnaphtalen-2-yl)selane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2017-01-02T16:11:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.354(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2573(8)
_cell_length_b                   14.6575(16)
_cell_length_c                   18.162(2)
_cell_measurement_reflns_used    9179
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      29.546
_cell_measurement_theta_min      2.64
_cell_volume                     1664.3(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics
'Diamond (version 3.2i; Crystal Impact GbR, Bonn'
_computing_structure_refinement  'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2\% \f & \w scans'
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            45865
_diffrn_reflns_theta_full        29.22
_diffrn_reflns_theta_max         29.22
_diffrn_reflns_theta_min         2.64
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    2.253
_exptl_absorpt_correction_T_max  0.5061
_exptl_absorpt_correction_T_min  0.3814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.087
_refine_diff_density_min         -0.094
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0731P)^2^+0.7571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                3675
_reflns_number_total             4516
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo7b00050_si_002.cif
_cod_data_source_block           mo_dfbgz1016_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '373.5K' was changed to '373.5' - the
value should be numeric and without a unit designator.

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032201.cif.
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4032201