Photocatalytic intermolecular carboarylation of alkenes by selective C-O bond cleavage of diarylethers.
Ji, Meishan; Chang, Chenyang; Wu, Xinxin; Zhu, Chen; Chemical communications (Cambridge, England) 57 (2021) 9240–9243; doi:10.1039/d1cc04038c

data_7128761
_publ_section_title
;
 Photocatalytic intermolecular carboarylation of alkenes by selective C-O
 bond cleavage of diarylethers.
;
_journal_issue                   73
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9240
_journal_page_last               9243
_journal_paper_doi               10.1039/d1cc04038c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C21 H15 N O S'
_chemical_formula_sum            'C21 H15 N O S'
_chemical_formula_weight         329.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-14 deposited with the CCDC.	2021-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.929(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0086(7)
_cell_length_b                   8.6711(5)
_cell_length_c                   21.5443(16)
_cell_measurement_reflns_used    3143
_cell_measurement_temperature    294.18(10)
_cell_measurement_theta_max      27.7190
_cell_measurement_theta_min      4.0070
_cell_volume                     1652.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.18(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   -1.00   27.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7452  -99.0000   30.0000 28

  2 omega  -25.00    4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7452  -99.0000 -120.0000 29

  3 omega  -50.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7452    0.0000  -30.0000 124

  4 omega  -13.00   25.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7452   38.0000 -150.0000 38

  5 omega  -30.00   54.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8077  -95.0000   99.0000 84

  6 omega  -91.00   -4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7452  -38.0000  -60.0000 87
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0070745000
_diffrn_orient_matrix_UB_12      -0.0689267000
_diffrn_orient_matrix_UB_13      0.0169236000
_diffrn_orient_matrix_UB_21      -0.0614346000
_diffrn_orient_matrix_UB_22      0.0325760000
_diffrn_orient_matrix_UB_23      0.0117377000
_diffrn_orient_matrix_UB_31      -0.0510853000
_diffrn_orient_matrix_UB_32      -0.0296278000
_diffrn_orient_matrix_UB_33      -0.0264559000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14216
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.815
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3380
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.1216
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1432P)^2^+7.9667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3118
_refine_ls_wR_factor_ref         0.3322
_reflns_number_gt                2511
_reflns_number_total             3380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc04038c2.cif
_cod_data_source_block           g101105a
_cod_depositor_comments          'Adding full bibliography for 7128761.cif.'
_cod_database_code               7128761
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.75
_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
2. Rigid bond restraints
 O1, C21
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.002
 C9, C14
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.002
 C15, C16
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.002
 C16, C21
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C5(H5), C12(H12), C13(H13), C14(H14), C11(H11),
 C18(H18), C17(H17), C10(H10), C19(H19), C20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'