Construction of 3,4-Dihydroisoquinolinones and Indanones via DTBP-Promoted Oxidative Coupling of N-Allylbenzamides with Aromatic Aldehydes.
Xu, Zhong-Qi; Wang, Chao; Li, Lin; Duan, Lili; Li, Yue-Ming; The Journal of organic chemistry 83 (2018) 9718–9728; doi:10.1021/acs.joc.8b01242

data_4035132
_publ_section_title
;
 Construction of 3,4-Dihydroisoquinolinones and Indanones via
 DTBP-Promoted Oxidative Coupling of N-Allylbenzamides with Aromatic
 Aldehydes.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9718
_journal_page_last               9728
_journal_paper_doi               10.1021/acs.joc.8b01242
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H19 N O2'
_chemical_formula_sum            'C22 H19 N O2'
_chemical_formula_weight         329.38
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.191(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4405(3)
_cell_length_b                   7.18600(10)
_cell_length_c                   18.7293(4)
_cell_measurement_reflns_used    6838
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      74.4000
_cell_measurement_theta_min      5.6210
_cell_volume                     1661.18(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9d (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      99.98(11)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_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     12.00  43.00   0.50    0.50    --    0.00  77.00-150.00   62
  2  \w    -25.00  39.00   0.50    0.50    --    0.00  82.00   0.00  128
  3  \w    -30.00  32.00   0.50    0.50    --    0.00  82.00 -90.00  124
  4  \w    -29.00  13.00   0.50    0.50    --    0.00  77.00 150.00   84
  5  \w    100.00 175.00   0.50    0.81    --   94.90  45.00-120.00  150
  6  \w    155.00 184.00   0.50    0.81    --   94.90  82.00 -60.00   58
  7  \w    134.00 167.00   0.50    0.81    --   94.90  82.00  90.00   66
  8  \w    111.00 139.00   0.50    0.81    --   94.90  82.00 -60.00   56
  9  \w     72.00 180.00   0.50    0.81    --   94.90  15.00-180.00  216
 10  \w     44.00 119.00   0.50    0.81    --   94.90 -61.00 -90.00  150
 11  \w     30.00 125.00   0.50    0.81    --   94.90 -77.00 -60.00  190
 12  \w      8.00 113.00   0.50    0.81    --   94.90 -45.00   0.00  210
;
_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      -0.0552519000
_diffrn_orient_matrix_UB_12      -0.0487944000
_diffrn_orient_matrix_UB_13      0.0667310000
_diffrn_orient_matrix_UB_21      -0.1111136000
_diffrn_orient_matrix_UB_22      0.0486810000
_diffrn_orient_matrix_UB_23      -0.0416832000
_diffrn_orient_matrix_UB_31      -0.0134204000
_diffrn_orient_matrix_UB_32      -0.2030008000
_diffrn_orient_matrix_UB_33      -0.0261328000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8882
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.581
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9d (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    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0573P)^2^+1.1237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2867
_reflns_number_total             3038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01242_si_002.cif
_cod_data_source_block           x170315-01
_cod_database_code               4035132
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.830
_reflns_odcompleteness_completeness 99.91
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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 1.288
_oxdiff_exptl_absorpt_empirical_full_min 0.824