A sustainable synthesis of 2-aryl-3-carboxylate indolines from N-aryl enamines under visible light irradiation
Wu, Cheng-Juan; Cao, Wen-Xiao; Lei, Tao; Li, Zhi-Hua; Meng, Qing-Yuan; Yang, Xiu-Long; Chen, Bin; Ramamurthy, Vaidhyanathan; Tung, Chen-Ho; Wu, Li-Zhu; Chemical Communications 53 (2017) 8320–8323; doi:10.1039/C7CC04358A

data_1546435
_publ_section_title
;
 A sustainable synthesis of 2-aryl-3-carboxylate indolines from N-aryl
 enamines under visible light irradiation
;
_journal_issue                   59
_journal_name_full               'Chemical Communications'
_journal_page_first              8320
_journal_page_last               8323
_journal_paper_doi               10.1039/C7CC04358A
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C24 H21 N O3'
_chemical_formula_sum            'C24 H21 N O3'
_chemical_formula_weight         371.42
_chemical_name_systematic
'(trans)-Ethyl 1-benzoyl-2-phenylindoline-3-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     iterative
_audit_creation_date             2016-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-04-05 deposited with the CCDC.
2017-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.272(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0796(14)
_cell_length_b                   13.6704(8)
_cell_length_c                   18.9052(13)
_cell_measurement_reflns_used    13887
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      28.8380
_cell_measurement_theta_min      3.8720
_cell_volume                     3958.1(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9953
_diffrn_measured_fraction_theta_max 0.8884
_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      8.00  87.00   0.50    1.09    --    0.10  38.00  60.00  158
  2  \w     -3.00  22.00   0.50    1.09    --    0.10 -38.00-180.00   50
  3  \w    -33.00   0.00   0.50    1.09    --    0.10 -82.00-150.00   66
  4  \w    -33.00  26.00   0.50    1.09    --    0.10 -82.00 -60.00  118
  5  \w    -34.00  19.00   0.50    1.09    --    0.10 -57.00  60.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0254596000
_diffrn_orient_matrix_UB_12      0.0114697000
_diffrn_orient_matrix_UB_13      0.0200448000
_diffrn_orient_matrix_UB_21      0.0378067000
_diffrn_orient_matrix_UB_22      -0.0033575000
_diffrn_orient_matrix_UB_23      0.0366846000
_diffrn_orient_matrix_UB_31      0.0084033000
_diffrn_orient_matrix_UB_32      0.0504468000
_diffrn_orient_matrix_UB_33      -0.0021246000
_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  0.0437
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32710
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.550
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/n-hexane'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         7752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0592
_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^)+(0.0922P)^2^+1.5264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1610
_refine_ls_wR_factor_ref         0.1741
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6015
_reflns_number_total             7752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc04358a2.cif
_cod_data_source_block           exp_53
_cod_database_code               1546435
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         C24H21N1O3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.988
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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:
 C1(H1), C2(H2), C25(H25), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C47(H47A,H47B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C28(H28), C29(H29),
  C30(H30), C31(H31), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39),
 C41(H41), C42(H42), C43(H43), C44(H44), C45(H45)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C48(H48A,H48B,H48C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.574