Homocoupling of 3-Halooxindole via Visible-Light Photocatalysis: A Mild Access to 3,3'-Bioxindoles.
Jia, Wen-Liang; He, Jian; Yang, Jia-Jing; Gao, Xue-Wang; Liu, Qiang; Wu, Li-Zhu; The Journal of organic chemistry 81 (2016) 7172–7181; doi:10.1021/acs.joc.6b01045

data_4036946
_publ_section_title
;
 Homocoupling of 3-Halooxindole via Visible-Light Photocatalysis: A Mild
 Access to 3,3'-Bioxindoles.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7172
_journal_page_last               7181
_journal_paper_doi               10.1021/acs.joc.6b01045
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C22 H24 N2 O2'
_chemical_formula_sum            'C22 H24 N2 O2'
_chemical_formula_weight         348.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_Hall           '-F 2uv 2vw'
_space_group_name_H-M_alt        'F d d d :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   14.4383(4)
_cell_length_b                   16.5487(6)
_cell_length_c                   31.6999(8)
_cell_measurement_reflns_used    2242
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6970
_cell_measurement_theta_min      3.9930
_cell_volume                     7574.2(4)
_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
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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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_details
;
  1 omega  -28.00   14.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571   57.0000   90.0000 42

  2 omega   43.00   90.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946 -178.0000   90.0000 47

  3 omega   -1.00   58.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   57.0000  -60.0000 59

  4 omega  -44.00  -18.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -75.0000  -85.0000 26

  5 omega  -51.00   -1.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -38.0000  150.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0160238500
_diffrn_orient_matrix_UB_12      0.0328755000
_diffrn_orient_matrix_UB_13      0.0123567500
_diffrn_orient_matrix_UB_21      -0.0285900000
_diffrn_orient_matrix_UB_22      -0.0127327000
_diffrn_orient_matrix_UB_23      0.0169369000
_diffrn_orient_matrix_UB_31      0.0365963000
_diffrn_orient_matrix_UB_32      -0.0243633000
_diffrn_orient_matrix_UB_33      0.0078274000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            8105
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.895
_diffrn_reflns_theta_min         3.720
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72637
_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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       block
_exptl_crystal_F_000             2976
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0594P)^2^+6.6164P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1488
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1655
_reflns_number_total             2233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01045_si_003.cif
_cod_data_source_block           jiawl1124
_cod_original_sg_symbol_H-M      'F d d d'
_cod_database_code               4036946
_reflns_odcompleteness_completeness 98.41
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              46562
_shelx_hkl_checksum              41027
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 1416812118.23
_olex2_submission_special_instructions 'No special instructions were received'