Tandem cyclisation of vinyl radicals: a sustainable approach to indolines utilizing visible-light photoredox catalysis
Pagire, Santosh K.; Reiser, Oliver; Green Chem. 19 (2017) 1721–; doi:10.1039/C7GC00445A

data_7227831
_publ_section_title
;
 Tandem cyclisation of vinyl radicals: a sustainable approach to indolines
 utilizing visible-light photoredox catalysis
;
_journal_issue                   7
_journal_name_full               'Green Chem.'
_journal_page_first              1721
_journal_paper_doi               10.1039/C7GC00445A
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C21 H23 N O4'
_chemical_formula_sum            'C21 H23 N O4'
_chemical_formula_weight         353.40
_chemical_melting_point          325
_chemical_name_systematic
'methyl (2S*,3R*)-3-(2-ethoxy-2-oxoethyl)-2-(o-tolyl)indoline-1-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-03
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-02-09 deposited with the CCDC.
2017-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.8249(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2857(2)
_cell_length_b                   22.5658(4)
_cell_length_c                   7.71479(14)
_cell_measurement_reflns_used    7105
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      76.1110
_cell_measurement_theta_min      3.8800
_cell_volume                     1773.97(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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    -98.00  -2.00   1.00    1.00    --  -40.71 125.00  30.00   96
  2  \w    -20.00  83.00   1.00    1.00    --   40.71 -99.00  60.00  103
  3  \w     14.00 117.00   1.00    1.00    --   40.71  37.00 -90.00  103
  4  \w     35.00 116.00   1.00    3.50    --  113.00-111.00 120.00   81
  5  \w     35.00  69.00   1.00    3.50    --  113.00 -30.00  60.00   34
  6  \w     52.00 158.00   1.00    3.50    --  113.00  15.00-120.00  106
  7  \w     35.00  69.00   1.00    3.50    --  113.00 -30.00   0.00   34
  8  \w     29.00 109.00   1.00    3.50    --  113.00 -94.00-150.00   80
  9  \w     35.00  69.00   1.00    3.50    --  113.00 -30.00 -30.00   34
 10  \w     35.00  69.00   1.00    3.50    --  113.00 -30.00 120.00   34
 11  \w     83.00 158.00   1.00    3.50    --  113.00  61.00 -60.00   75
 12  \w     38.00  77.00   1.00    3.50    --  113.00 -45.00 120.00   39
 13  \w     38.00  77.00   1.00    3.50    --  113.00 -45.00-180.00   39
 14  \w     35.00  69.00   1.00    3.50    --  113.00 -30.00-180.00   34
 15  \w     29.00 109.00   1.00    3.50    --  113.00 -94.00 -90.00   80
 16  \w     29.00 109.00   1.00    3.50    --  113.00 -94.00 150.00   80
 17  \w     39.00 143.00   1.00    3.50    --  113.00 -61.00  90.00  104
 18  \w     35.00  69.00   1.00    3.50    --  113.00 -30.00 -90.00   34
 19  \w     25.00 158.00   1.00    3.50    --  113.00   6.00  94.55  133
 20  \w     83.00 158.00   1.00    3.50    --  113.00  61.00 -90.00   75
 21  \w     83.00 158.00   1.00    3.50    --  113.00  61.00 -30.00   75
 22  \w   -115.00 -88.00   1.00    1.00    --  -40.71 -57.00 -30.00   27
 23  \w   -119.00  -7.00   1.00    1.00    --  -40.71 -77.00  90.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0236979000
_diffrn_orient_matrix_UB_12      -0.0625457000
_diffrn_orient_matrix_UB_13      -0.0780040000
_diffrn_orient_matrix_UB_21      0.1491298000
_diffrn_orient_matrix_UB_22      -0.0086890000
_diffrn_orient_matrix_UB_23      0.0068266000
_diffrn_orient_matrix_UB_31      0.0068476000
_diffrn_orient_matrix_UB_32      -0.0259477000
_diffrn_orient_matrix_UB_33      0.1857683000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15306
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         76.327
_diffrn_reflns_theta_min         3.918
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       irregular
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane, pentane'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_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^+0.6942P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3222
_reflns_number_total             3706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7gc00445a2.cif
_cod_data_source_block           p069
_cod_depositor_comments          'Adding full bibliography for 7227831.cif.'
_cod_database_code               7227831
_chemical_oxdiff_formula         'C21 H23 N O4'
_chemical_oxdiff_usercomment     Pagire_Reiser_SKP-27
_reflns_odcompleteness_completeness 98.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H2BC)=Sof(H2BD)=Sof(O1A)=1-FVAR(1)
 Sof(O1)=Sof(H2AA)=Sof(H2AB)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C6(H6), C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2AA,H2AB), C2(H2BC,H2BD)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C16(H16), C11(H11), C19(H19), C10(H10), C17(H17), C18(H18)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              32271
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-02
_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 1.617
_oxdiff_exptl_absorpt_empirical_full_min 0.707