Enantioselective radical process for synthesis of chiral indolines by metalloradical alkylation of diverse C(sp<sup>3</sup>)-H bonds.
Wen, Xin; Wang, Yong; Zhang, X. Peter; Chemical science 9 (2018) 5082–5086; doi:10.1039/c8sc01476k

data_1549408
_publ_section_title
;
 Enantioselective radical process for synthesis of chiral indolines by
 metalloradical alkylation of diverse C(sp<sup>3</sup>)-H bonds.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              5082
_journal_page_last               5086
_journal_paper_doi               10.1039/c8sc01476k
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C112 H88 Co N8 O8'
_chemical_formula_sum            'C112 H88 Co N8 O8'
_chemical_formula_weight         1732.83
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-03-30 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7206(3)
_cell_length_b                   36.0918(7)
_cell_length_c                   22.8341(4)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.52
_cell_measurement_theta_min      2.45
_cell_volume                     10483.3(4)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34025
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         2.448
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_exptl_absorpt_coefficient_mu    1.730
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2013). TWINABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             3628
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_platon_squeeze_details
;
 Solvents used for crystallization are chloroform and hexane. Both solvents are
 present in the system but are severely disordered and can not be satisfactorily 
 refined. Program SQUEEZE is used to deal with the disordered solvents. there are
 roughly half chloroform molecule and one hexane in the asymmtric unit.
 PART 1 10.25
 C1S   1    0.932062    0.487115    0.584401    10.25000    0.04872
 CL1S  6    1.049426    0.503401    0.618493    10.25000    0.06829
 CL2S  6    0.945660    0.451582    0.540470    10.25000    0.06618
 CL3S  6    0.878596    0.461954    0.653190    10.25000    0.11106
 PART 2 10.25
 C1X   1    0.941035    0.486629    0.610319    10.25000    0.05918
 CL1X  6    1.056545    0.509953    0.598962    10.25000    0.04730
 CL2X  6    0.919338    0.447894    0.575612    10.25000    0.09223
 CL3X  6    0.914775    0.490404    0.680716    10.25000    0.17920
 PART 0
 PART 1 10.50000
 C1X   1    1.074573    0.476711    0.597861    10.50000    0.13978
 C2X   1    0.957514    0.482198    0.513488    10.50000    0.21060
 C3X   1    0.896159    0.460681    0.532634    10.50000    0.09442
 C4X   1    1.046409    0.516453    0.568888    10.50000    0.06461
 C2S   1    0.259529    0.086750    0.289274    10.50000    0.12623
 C3S   1    0.136799    0.089555    0.251317    10.50000    0.10002
 C4S   1    0.015123    0.076565    0.266061    10.50000    0.09003
 C5S   1   -0.078811    0.093205    0.231466    10.50000    0.07068
 C6S   1   -0.196098    0.073396    0.238683    10.50000    0.09114 
 PART 0
;
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.003(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         8791
_refine_ls_number_restraints     562
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0275P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0854
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                7633
_reflns_number_total             8791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01476k2.cif
_cod_data_source_block           C112H88CoN8O8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1549405--1549408.cif.
;
_cod_database_code               1549408
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.544
_shelx_estimated_absorpt_t_max   0.819
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              40659
_shelx_fab_checksum              2879