Visible-Light-Mediated Aerobic Selenation of (Hetero)Arenes with Diselenides
Zhang, Qing-Bao; Ban, Yong-Liang; Yuan, Pan-Feng; Peng, Shoujiao; Fang, Jianguo; Wu, Li-Zhu; Liu, Qiang; Green Chem.  (2017) –; doi:10.1039/C7GC02803B

data_7229455
_publ_section_title
;
 Visible-Light-Mediated Aerobic Selenation of (Hetero)Arenes with
 Diselenides
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC02803B
_journal_year                    2017
_chemical_formula_moiety         'C16 H13 N O3 Se'
_chemical_formula_sum            'C16 H13 N O3 Se'
_chemical_formula_weight         346.23
_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_block_doi                 10.5517/ccdc.csd.cc1pvh12
_audit_creation_date             2016-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2017-09-14 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.2923(5)
_cell_length_b                   11.1395(5)
_cell_length_c                   22.6048(7)
_cell_measurement_reflns_used    1506
_cell_measurement_temperature    292.87(10)
_cell_measurement_theta_max      26.1310
_cell_measurement_theta_min      3.6130
_cell_volume                     2843.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.87(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   23.00   79.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  -30.0000 56

  2 omega    7.00   95.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -150.0000 88

  3 omega   30.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  120.0000 28
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0228091000
_diffrn_orient_matrix_UB_12      -0.0238416000
_diffrn_orient_matrix_UB_13      -0.0267902000
_diffrn_orient_matrix_UB_21      -0.0231142000
_diffrn_orient_matrix_UB_22      0.0572697000
_diffrn_orient_matrix_UB_23      -0.0074516000
_diffrn_orient_matrix_UB_31      0.0538183000
_diffrn_orient_matrix_UB_32      0.0144652000
_diffrn_orient_matrix_UB_33      -0.0144916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7581
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         3.605
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0252P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0851
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1890
_reflns_number_total             2791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7gc02803b2.cif
_cod_data_source_block           zhangqb_1114
_cod_database_code               7229455
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-11-15
_olex2_submission_special_instructions 'No special instructions were received'