Visible-light-induced intermolecular aminoselenation of alkenes
Liu, Gong-Qing; Zhou, Chen-Fan; Zhang, Yun-Qian; Yi, Wei; Wang, Peng-Fei; Liu, Ji; Ling, Yong; Green Chemistry 23 (2021) 9968–9973; doi:10.1039/D1GC03195C

data_7243857
_publ_section_title
;
 Visible-light-induced intermolecular aminoselenation of alkenes
;
_journal_issue                   24
_journal_name_full               'Green Chemistry'
_journal_page_first              9968
_journal_page_last               9973
_journal_paper_doi               10.1039/D1GC03195C
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H29 N O2 S Se'
_chemical_formula_sum            'C24 H29 N O2 S Se'
_chemical_formula_weight         474.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-31
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-08-09 deposited with the CCDC.	2021-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.968(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8465(7)
_cell_length_b                   23.1935(15)
_cell_length_c                   10.1145(8)
_cell_measurement_reflns_used    3914
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.4870
_cell_measurement_theta_min      2.3520
_cell_volume                     2184.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     42.00  92.00   1.00    5.00    --   11.90 178.00  30.00   50
  2  \w    -12.00  84.00   1.00    5.00    --   11.90  38.00  90.00   96
  3  \w     34.00  84.00   1.00    5.00    --   11.90-178.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0141586000
_diffrn_orient_matrix_UB_12      0.0281589000
_diffrn_orient_matrix_UB_13      -0.0198256000
_diffrn_orient_matrix_UB_21      0.0748022000
_diffrn_orient_matrix_UB_22      -0.0057246000
_diffrn_orient_matrix_UB_23      0.0259134000
_diffrn_orient_matrix_UB_31      -0.0026062000
_diffrn_orient_matrix_UB_32      -0.0105370000
_diffrn_orient_matrix_UB_33      -0.0665358000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11701
_diffrn_reflns_point_group_measured_fraction_full 0.817
_diffrn_reflns_point_group_measured_fraction_max 0.642
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.672
_diffrn_reflns_theta_min         2.129
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         7934
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0237P)^2^+0.0964P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.500
_reflns_Friedel_fraction_full    0.623
_reflns_Friedel_fraction_max     0.438
_reflns_number_gt                7061
_reflns_number_total             7934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03195c2.cif
_cod_data_source_block           se1
_cod_depositor_comments
'Adding full bibliography for 7243855--7243857.cif.'
_cod_database_code               7243857
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.011(9)
 -0.011(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C32(H32), C37(H37), C42(H42), C4(H4), C6(H6), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C33(H33A,H33B), C35(H35A,H35B), C36(H36A,H36B), C41(H41A,
 H41B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C10(H10A,H10B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C44(H44), C45(H45),
 C46(H46), C47(H47), C48(H48), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
  C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
3.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              85259
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.160
_oxdiff_exptl_absorpt_empirical_full_min 0.890