An efficient copper-catalyzed synthesis of symmetrical bis(N-arylbenzamide) selenides and their conversion to hypervalent spirodiazaselenuranes and hydroxy congeners.
Kadu, Rahul; Batabyal, Monojit; Kadyan, Heena; Koner, Apurba Lal; Kumar, Sangit; Dalton transactions (Cambridge, England : 2003) 48 (2019) 7249–7260; doi:10.1039/c8dt04832k

data_7048787
_publ_section_title
;
 An efficient copper-catalyzed synthesis of symmetrical
 bis(N-arylbenzamide) selenides and their conversion to hypervalent
 spirodiazaselenuranes and hydroxy congeners.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7249
_journal_page_last               7260
_journal_paper_doi               10.1039/c8dt04832k
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C34 H22 N2 O2 Se'
_chemical_formula_sum            'C34 H22 N2 O2 Se'
_chemical_formula_weight         569.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2018-11-30 deposited with the CCDC.
2019-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.073(3)
_cell_length_b                   14.264(2)
_cell_length_c                   16.949(3)
_cell_measurement_reflns_used    1823
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.09
_cell_measurement_theta_min      2.40
_cell_volume                     5094.6(14)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0870
_diffrn_reflns_av_unetI/netI     0.1240
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18263
_diffrn_reflns_point_group_measured_fraction_full 0.853
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.100
_diffrn_reflns_theta_max         25.100
_diffrn_reflns_theta_min         1.428
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.510
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0759 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.8241.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             2320
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 1476 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         7747
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0330P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    0.698
_reflns_Friedel_fraction_max     0.698
_reflns_number_gt                5103
_reflns_number_total             7747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt04832k2.cif
_cod_data_source_block           final1_a
_cod_depositor_comments          'Adding full bibliography for 7048787.cif.'
_cod_original_cell_volume        5094.7(14)
_cod_database_code               7048787
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C32(H32), C56(H56), C67(H67), C26(H26), C44(H44), C33(H33), C50(H50),
 C20(H20), C11(H11), C2(H2), C27(H27), C43(H43), C19(H19), C53(H53), C14(H14),
 C60(H60), C5(H5), C28(H28), C49(H49), C4(H4), C36(H36), C15(H15), C64(H64),
 C31(H31), C16(H16), C55(H55), C21(H21), C39(H39), C37(H37), C61(H61), C30(H30),
  C13(H13), C22(H22), C66(H66), C3(H3), C38(H38), C65(H65), C62(H62), C54(H54),
 C45(H45), C48(H48), C47(H47), C9(H9), C10(H10)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'