NIS-mediated oxidative arene C(sp<sup>2</sup>)-H amidation toward 3,4-dihydro-2(1H)-quinolinone, phenanthridone, and N-fused spirolactam derivatives.
Wu, Lingang; Hao, Yanan; Liu, Yuxiu; Wang, Qingmin; Organic & biomolecular chemistry 17 (2019) 6762–6770; doi:10.1039/c9ob01277j

data_7156923
_publ_section_title
;
 NIS-mediated oxidative arene C(sp<sup>2</sup>)-H amidation toward
 3,4-dihydro-2(1H)-quinolinone, phenanthridone, and N-fused spirolactam
 derivatives.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6762
_journal_page_last               6770
_journal_paper_doi               10.1039/c9ob01277j
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C16 H15 N O'
_chemical_formula_sum            'C16 H15 N O'
_chemical_formula_weight         237.29
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-04-01 deposited with the CCDC.    2019-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.141(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7435(14)
_cell_length_b                   7.1127(9)
_cell_length_c                   15.6205(15)
_cell_measurement_reflns_used    2897
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      28.7080
_cell_measurement_theta_min      3.8770
_cell_volume                     1299.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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_temperature      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.998
_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 -84.00 94.00 0.50 40.00 -- 5.00 45.00 150.00 356 2 \w -97.00 81.00 0.50 40.00 -- -8.10 45.00 0.00 356 3 \w -78.00 -53.00 0.50 40.00 -- -8.10 45.00 90.00 50 4 \w -5.00 43.00 0.50 40.00 -- -8.10 45.00 90.00 96 5 \w -97.00 -84.50 0.50 40.00 -- -8.10 45.00 171.65 25'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0058045000
_diffrn_orient_matrix_UB_12      0.0892697000
_diffrn_orient_matrix_UB_13      0.0201569000
_diffrn_orient_matrix_UB_21      0.0411275000
_diffrn_orient_matrix_UB_22      0.0259929000
_diffrn_orient_matrix_UB_23      -0.0284243000
_diffrn_orient_matrix_UB_31      -0.0441749000
_diffrn_orient_matrix_UB_32      0.0360414000
_diffrn_orient_matrix_UB_33      -0.0294119000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19218
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         3.352
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0594P)^2^+0.2324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1472
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1791
_reflns_number_total             3232
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01277j2.cif
_cod_data_source_block           m20190311c
_cod_depositor_comments          'Adding full bibliography for 7156923.cif.'
_cod_database_code               7156923
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H15NO
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              68453
_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 2.065
_oxdiff_exptl_absorpt_empirical_full_min 0.379