Indium-Mediated Intramolecular Reaction of N-(2-Iodobenzoyl)azabenzonorbornadienes: A General Access to Dihydrobenzo[c]phenanthridinones.
Liu, Yang; Lei, Kang; Liu, Na; Sun, Dong-Wei; Hua, Xue-Wen; Li, Ya-Juan; Xu, Xiao-Hua; The Journal of organic chemistry 81 (2016) 5495–5503; doi:10.1021/acs.joc.6b00839

data_4036892
_publ_section_title
;
 Indium-Mediated Intramolecular Reaction of
 N-(2-Iodobenzoyl)azabenzonorbornadienes: A General Access to
 Dihydrobenzo[c]phenanthridinones.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5495
_journal_page_last               5503
_journal_paper_doi               10.1021/acs.joc.6b00839
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28
_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   mixed
_audit_creation_date             2015-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6275(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.96672(9)
_cell_length_b                   17.5832(2)
_cell_length_c                   9.10756(11)
_cell_measurement_reflns_used    15178
_cell_measurement_temperature    173
_cell_measurement_theta_max      78.9720
_cell_measurement_theta_min      4.8110
_cell_volume                     1275.71(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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_temperature      173
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.971
_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    -50.00  55.00   1.00    5.00    --  -35.00  72.00  72.00  105
  2  \w   -112.00 -21.00   1.00    5.00    --  -35.00 -72.00 144.00   91
  3  \w   -112.00 -21.00   1.00    5.00    --  -35.00 -72.00-180.00   91
  4  \w    -45.00  45.00   1.00    5.00    --  -35.00  43.00-180.00   90
  5  \w   -119.00 -29.00   1.00    5.00    --  -35.00 -44.00  36.00   90
  6  \w   -123.00 -33.00   1.00    5.00    --  -35.00 -44.00 108.00   90
  7  \w    -50.00  40.00   1.00    5.00    --  -35.00  43.00  36.00   90
  8  \w    -50.00  40.00   1.00    5.00    --  -35.00  72.00 144.00   90
  9  \w   -115.00 -22.00   1.00    5.00    --  -35.00 -72.00  72.00   93
 10  \w   -200.00 -96.00   1.00   20.00    -- -110.00 -15.00  72.00  104
 11  \w   -125.00 -25.00   1.00   20.00    -- -110.00  72.00  72.00  100
 12  \w   -125.00 -31.00   1.00   20.00    -- -110.00  72.00-108.00   94
 13  \w   -200.00-110.00   1.00   20.00    -- -110.00 -15.00-108.00   90
 14  \w   -115.00 -25.00   1.00   20.00    -- -110.00  72.00 144.00   90
 15  \w   -125.00 -32.00   1.00   20.00    -- -110.00  72.00   0.00   93
 16  \w   -200.00-105.00   1.00   20.00    -- -110.00 -72.00 -36.00   95
 17  \w   -200.00-110.00   1.00   20.00    -- -110.00 -72.00  36.00   90
 18  \w   -187.00 -96.00   1.00   20.00    -- -110.00 -72.00-180.00   91
 19  \w   -125.00 -33.00   1.00   20.00    -- -110.00  72.00 -72.00   92
 20  \w   -187.00 -96.00   1.00   20.00    -- -110.00 -15.00   0.00   91
 21  \w   -115.00 -25.00   1.00   20.00    -- -110.00  72.00-180.00   90
 22  \w   -187.00 -97.00   1.00   20.00    -- -110.00 -72.00 108.00   90
 23  \w   -119.00 -29.00   1.00   20.00    -- -110.00  72.00 108.00   90
 24  \w   -187.00 -96.00   1.00   20.00    -- -110.00 -72.00   0.00   91
 25  \w   -115.00 -25.00   1.00   20.00    -- -110.00  72.00 -36.00   90
 26  \w   -191.00-101.00   1.00   20.00    -- -110.00 -44.00-108.00   90
 27  \w   -125.00 -33.00   1.00   20.00    -- -110.00  72.00-144.00   92
 28  \w   -200.00-110.00   1.00   20.00    -- -110.00 -72.00  72.00   90
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1801962000
_diffrn_orient_matrix_UB_12      -0.0278656000
_diffrn_orient_matrix_UB_13      -0.0282333000
_diffrn_orient_matrix_UB_21      0.0630069000
_diffrn_orient_matrix_UB_22      0.0828478000
_diffrn_orient_matrix_UB_23      0.0028467000
_diffrn_orient_matrix_UB_31      0.0315005000
_diffrn_orient_matrix_UB_32      -0.0061129000
_diffrn_orient_matrix_UB_33      0.1666718000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            20375
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.210
_diffrn_reflns_theta_min         5.031
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_type              'Rigaku MM007HF (Cu) X-ray Source'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.288
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0111(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0490P)^2^+0.3220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2592
_reflns_number_total             2694
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00839_si_001.cif
_cod_data_source_block           p20151215a
_cod_original_cell_volume        1275.72(3)
_cod_database_code               4036892
_chemical_oxdiff_formula         C17H13NO
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.863
_reflns_odcompleteness_completeness 96.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.96
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_shelx_res_checksum              86062
_shelx_hkl_checksum              65326
_shelx_shelxl_version_number     2014/7
_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 1.539
_oxdiff_exptl_absorpt_empirical_full_min 0.727