Water enables the tunable electrochemical synthesis of heterocyclic 3a- or 5a-bromoindolines
Wu, Ying-Ai; Wang, Rui-An; Jiang, Shu-Yun; Jiang, Tai-Bai; Song, Jun-Rong; Shi, Jun; Wu, Wei; Pan, Wei-Dong; Ren, Hai; Green Chemistry 24 (2022) 6720–6726; doi:10.1039/D2GC02086F

data_7245329
_publ_section_title
;
 Water enables the tunable electrochemical synthesis of heterocyclic 3a-
 or 5a-bromoindolines
;
_journal_issue                   17
_journal_name_full               'Green Chemistry'
_journal_page_first              6720
_journal_page_last               6726
_journal_paper_doi               10.1039/D2GC02086F
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C17 H16 Br N O3 S'
_chemical_formula_sum            'C17 H16 Br N O3 S'
_chemical_formula_weight         394.28
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2bybh4
_audit_creation_date             2022-01-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-05-17 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                95.863(10)
_cell_angle_beta                 90.752(10)
_cell_angle_gamma                116.824(12)
_cell_formula_units_Z            2
_cell_length_a                   8.2932(10)
_cell_length_b                   8.8298(11)
_cell_length_c                   12.4718(14)
_cell_measurement_reflns_used    1731
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.0970
_cell_measurement_theta_min      2.9300
_cell_volume                     808.94(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -11.00  50.00   1.00    2.50    --   15.65 -99.00   0.00   61
  2  \w    -25.00  22.00   1.00    2.50    --  -16.43 -99.00 120.00   47
  3  \w    -53.00  20.00   1.00    2.50    --   15.65 -38.00 150.00   73
  4  \w    -50.00 -23.00   1.00    2.50    --  -16.43 121.00  30.00   27
  5  \w    -39.00  82.00   1.00    2.50    --   15.65   0.00-180.00  121
  6  \w    -86.00 -44.00   1.00    2.50    --  -16.43 152.00-169.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0221891000
_diffrn_orient_matrix_UB_12      -0.0288493000
_diffrn_orient_matrix_UB_13      -0.0559155000
_diffrn_orient_matrix_UB_21      -0.0333613000
_diffrn_orient_matrix_UB_22      -0.0858102000
_diffrn_orient_matrix_UB_23      0.0111105000
_diffrn_orient_matrix_UB_31      -0.0872983000
_diffrn_orient_matrix_UB_32      -0.0052742000
_diffrn_orient_matrix_UB_33      0.0057605000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5512
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.497
_diffrn_reflns_theta_max         24.497
_diffrn_reflns_theta_min         2.604
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.619
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0572
_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^)+(0.0595P)^2^+1.7408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1524
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2022
_reflns_number_total             2687
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02086f2.cif
_cod_data_source_block           exp_10608
_cod_depositor_comments          'Adding full bibliography for 7245329.cif.'
_cod_original_cell_volume        808.94(18)
_cod_database_code               7245329
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.794
_shelx_estimated_absorpt_t_min   0.590
_reflns_odcompleteness_completeness 99.94
_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 Ternary CH refined with riding coordinates:
 C10(H10), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C2(H2), C16(H16), C15(H15), C3(H3), C13(H13)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 1.789
_oxdiff_exptl_absorpt_empirical_full_min 0.673