Fast construction of isoquinolin-1(2H)-ones by direct intramolecular C-H/N-H functionalization under metal-free conditions.
Wen, Li-Rong; Ren, Guang-Yi; Geng, Rui-Sen; Zhang, Lin-Bao; Li, Ming; Organic & biomolecular chemistry 18 (2020) 225–229; doi:10.1039/c9ob02430a

data_7157295
_publ_section_title
;
 Fast construction of isoquinolin-1(2H)-ones by direct intramolecular
 C-H/N-H functionalization under metal-free conditions.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              225
_journal_page_last               229
_journal_paper_doi               10.1039/c9ob02430a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C19 H17 N O2'
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-02 deposited with the CCDC.	2019-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.0080(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.07170(10)
_cell_length_b                   15.9713(2)
_cell_length_c                   9.99690(10)
_cell_measurement_reflns_used    11161
_cell_measurement_temperature    170.01(10)
_cell_measurement_theta_max      66.4800
_cell_measurement_theta_min      2.7480
_cell_volume                     1430.56(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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      170.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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   -119.00 -34.00   0.50    0.10    --  -47.32 -51.00  15.00  170
  2  \w    -24.00  61.00   0.50    0.10    --   47.32 -51.00  15.00  170
  3  \w     34.00 119.00   0.50    0.10    --   47.32  51.00 161.00  170
  4  \w   -168.00 -85.00   0.50    0.10    --  -99.00 -51.00  15.00  166
  5  \w   -113.00 -26.00   0.50    0.10    --  -99.00  51.00 161.00  174
  6  \w     31.00 117.00   0.50    0.10    --  103.25 -51.00  15.00  172
  7  \w     90.00 169.00   0.50    0.10    --  103.25  51.00 161.00  158
  8  \w   -119.00 -71.00   0.50    0.10    --  -47.32-125.00-180.00   96
  9  \w    -61.00  25.00   0.50    0.10    --  -47.32  51.00 161.00  172
 10  \w   -119.00 -71.00   0.50    0.10    --  -47.32-125.00 150.00   96
 11  \w   -115.00 -26.00   0.50    0.10    --  -99.00  61.00-120.00  178
 12  \w   -113.00 -24.00   0.50    0.10    --  -99.00  15.00   0.00  178
 13  \w   -115.00 -26.00   0.50    0.10    --  -99.00  61.00  30.00  178
 14  \w     31.00 109.00   0.50    0.10    --  103.25 -94.00-150.00  156
 15  \w     33.00  58.00   0.50    0.10    --  103.25 -94.00-120.00   50
 16  \w     81.00 167.00   0.50    0.10    --  103.25  77.00 150.00  172
 17  \w     67.00  98.00   0.50    0.10    --  103.25 -94.00-120.00   62
 18  \w     90.00 168.00   0.50    0.10    --  103.25  15.00 -90.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1700357000
_diffrn_orient_matrix_UB_12      -0.0009490000
_diffrn_orient_matrix_UB_13      0.0469959000
_diffrn_orient_matrix_UB_21      0.0188604000
_diffrn_orient_matrix_UB_22      -0.0601886000
_diffrn_orient_matrix_UB_23      -0.1165305000
_diffrn_orient_matrix_UB_31      0.0171745000
_diffrn_orient_matrix_UB_32      0.0753683000
_diffrn_orient_matrix_UB_33      -0.0925163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12432
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.542
_diffrn_reflns_theta_max         66.542
_diffrn_reflns_theta_min         5.267
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.472
_exptl_crystal_size_min          0.345
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0566P)^2^+0.9994P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2432
_reflns_number_total             2497
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02430a2.cif
_cod_data_source_block           tx70
_cod_depositor_comments          'Adding full bibliography for 7157295.cif.'
_cod_original_cell_volume        1430.55(3)
_cod_database_code               7157295
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHNO
_shelx_estimated_absorpt_t_max   0.794
_shelx_estimated_absorpt_t_min   0.732
_reflns_odcompleteness_completeness 98.05
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
;
_shelx_res_checksum              79793
_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 1.567
_oxdiff_exptl_absorpt_empirical_full_min 0.605