Enantioselective photoredox dehalogenative protonation
Hou, Meimei; Lin, Lu; Chai, Xiangpei; Zhao, Xiaowei; Qiao, Baokun; Jiang, Zhiyong; Chemical Science  (2019) –; doi:10.1039/C9SC02000D

data_1551280
_publ_section_title
;
 Enantioselective photoredox dehalogenative protonation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC02000D
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H10 Cl2 O'
_chemical_formula_sum            'C10 H10 Cl2 O'
_chemical_formula_weight         217.08
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_audit_update_record
;
2018-04-29 deposited with the CCDC.    2019-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.04728(18)
_cell_length_b                   19.5159(6)
_cell_length_c                   20.2528(8)
_cell_measurement_reflns_used    3155
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6540
_cell_measurement_theta_min      4.3940
_cell_volume                     1994.95(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -101.00  -26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000  -90.0000 75

  2 omega  -98.00  -42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -180.0000 56

  3 omega   26.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   57.0000  -90.0000 60

  4 omega   18.00   65.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -77.0000  150.0000 47

  5 omega   14.00   68.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -19.0000  -60.0000 54

  6 omega  -35.00  -10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -19.0000  -60.0000 25

  7 omega   58.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  178.0000 -180.0000 48

  8 omega   63.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   77.0000  -90.0000 42

  9 omega   16.00   43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   77.0000  -90.0000 27

 10 omega   58.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  178.0000   60.0000 50

 11 omega   53.00   80.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -130.0000  -26.0000 27

 12 omega   69.00  107.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 38

 13 omega  123.00  177.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 54

 14 omega   42.00   90.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 48

 15 omega   39.00   91.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 52

 16 omega  128.00  163.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 35

 17 omega   83.00  109.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 26

 18 omega   38.00  152.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  120.0000 114

 19 omega   43.00   77.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 34

 20 omega   47.00   97.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 50

 21 omega   38.00   99.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 61

 22 omega   26.00   52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   90.0000 26

 23 omega  -29.00   -3.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   90.0000 26

 24 omega  142.00  151.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 9
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0040301000
_diffrn_orient_matrix_UB_12      -0.0133649000
_diffrn_orient_matrix_UB_13      0.0749899000
_diffrn_orient_matrix_UB_21      -0.0899339000
_diffrn_orient_matrix_UB_22      0.0742855000
_diffrn_orient_matrix_UB_23      0.0124077000
_diffrn_orient_matrix_UB_31      -0.2916829000
_diffrn_orient_matrix_UB_32      -0.0231149000
_diffrn_orient_matrix_UB_33      -0.0027569000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8713
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.366
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.490
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.446
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0670P)^2^+0.1539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3017
_reflns_number_total             3534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc02000d2.cif
_cod_data_source_block           hm23026
_cod_original_cell_volume        1994.94(12)
_cod_database_code               1551280
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2Cl2
_shelx_estimated_absorpt_t_max   0.610
_shelx_estimated_absorpt_t_min   0.474
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C1'(H1'), C2'(H2')
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C3'(H3'A,H3'B), C4'(H4'A,H4'B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C7'(H7'), C8'(H8'), C10'(H10')
;
_olex2_submission_special_instructions 'No special instructions were received'