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_4036945
_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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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)
;
_cell_angle_alpha                107.369(11)
_cell_angle_beta                 102.785(11)
_cell_angle_gamma                92.675(10)
_cell_formula_units_Z            4
_cell_length_a                   9.4924(12)
_cell_length_b                   13.7707(16)
_cell_length_c                   15.835(2)
_cell_measurement_reflns_used    1939
_cell_measurement_temperature    220.60(10)
_cell_measurement_theta_max      20.8450
_cell_measurement_theta_min      3.7310
_cell_volume                     1912.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_environment      N~2~
_diffrn_ambient_temperature      220.60(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -4.00   86.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   38.0000 -120.0000 60

  2 omega   -5.00   22.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916  -99.0000   60.0000 18

  3 omega    8.00   62.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291  -99.0000  -90.0000 36

  4 omega  -18.00   13.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916  -99.0000   30.0000 21

  5 omega  -43.00   65.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291  -19.0000   30.0000 72

  6 omega  -20.00    5.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916  -99.0000 -150.0000 17

  7 omega   36.00   96.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291  178.0000   90.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0305157000
_diffrn_orient_matrix_UB_12      -0.0316500000
_diffrn_orient_matrix_UB_13      -0.0339106000
_diffrn_orient_matrix_UB_21      -0.0564461000
_diffrn_orient_matrix_UB_22      0.0070569000
_diffrn_orient_matrix_UB_23      -0.0345767000
_diffrn_orient_matrix_UB_31      0.0429068000
_diffrn_orient_matrix_UB_32      0.0436403000
_diffrn_orient_matrix_UB_33      0.0001270000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.1311
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13474
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.462
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         7509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.0738
_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^)+(0.0592P)^2^+0.0386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.2150
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3283
_reflns_number_total             7509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01045_si_002.cif
_cod_data_source_block           jiawl0310
_cod_database_code               4036945
_reflns_odcompleteness_completeness 99.74
_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), C20(H20A,H20B), C31(H31A,H31B), C42(H42A,H42B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C24(H24), C25(H25), C26(H26), C27(H27), C35(H35), C36(H36), C37(H37), C38(H38)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C43(H43A,H43B,H43C), C44(H44A,
 H44B,H44C)
;
_shelx_res_checksum              78632
_shelx_hkl_checksum              47284
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-03-11
_olex2_submission_special_instructions 'No special instructions were received'