Synthesis of phenanthridines by I<sub>2</sub>-mediated sp<sup>3</sup> C-H amination.
Fang, Benyao; Hou, Jiao; Tian, Jinyue; Yu, Wenquan; Chang, Junbiao; Organic & biomolecular chemistry 18 (2020) 3312–3323; doi:10.1039/d0ob00433b

data_7157462
_publ_section_title
;
 Synthesis of phenanthridines by I<sub>2</sub>-mediated sp<sup>3</sup> C-H
 amination.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3312
_journal_page_last               3323
_journal_paper_doi               10.1039/d0ob00433b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H14 Cl N'
_chemical_formula_sum            'C20 H14 Cl N'
_chemical_formula_weight         303.77
_chemical_melting_point          445.0(10)
_chemical_name_systematic        2-chloro-6-(p-tolyl)phenanthridine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-28 deposited with the CCDC.	2020-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                105.531(8)
_cell_angle_beta                 91.027(9)
_cell_angle_gamma                101.719(10)
_cell_formula_units_Z            2
_cell_length_a                   5.5878(7)
_cell_length_b                   10.8004(11)
_cell_length_c                   13.7039(12)
_cell_measurement_reflns_used    1265
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4740
_cell_measurement_theta_min      4.3670
_cell_volume                     777.93(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_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    -62.00  36.00   1.00    1.00    --  -33.50  77.00   0.00   98
  2  \w    -36.00  74.00   1.00    1.00    --   36.54 -19.00 -30.00  110
  3  \w     29.00 102.00   1.00    1.00    --   36.54-142.00 106.00   73
  4  \w     -4.00  77.00   1.00    1.00    --   36.54 -99.00-120.00   81
  5  \w     -4.00  77.00   1.00    1.00    --   36.54 -99.00   0.00   81
  6  \w     18.00 105.00   1.00    1.00    --   36.54  57.00-180.00   87
  7  \w     57.00 111.00   1.00    1.00    --   36.54 178.00-180.00   54
  8  \w      8.00 106.00   1.00    1.00    --   36.54  77.00  30.00   98
  9  \w      8.00 106.00   1.00    1.00    --   36.54  77.00 120.00   98
 10  \w     18.00 105.00   1.00    1.00    --   36.54  57.00 150.00   87
 11  \w    -31.00  31.00   1.00    1.00    --   36.54 -57.00 -90.00   62
 12  \w     61.00  86.00   1.00    1.00    --   36.54 178.00 -30.00   25
 13  \w     37.00 148.00   1.00    2.50    --  108.00 -15.00  60.00  111
 14  \w     37.00 129.00   1.00    2.50    --  108.00 -30.00-120.00   92
 15  \w     40.00 124.00   1.00    2.50    --  108.00 -45.00   0.00   84
 16  \w     38.00  99.00   1.00    2.50    --  108.00 -94.00 150.00   61
 17  \w     46.00 109.00   1.00    2.50    --  108.00 -94.00  30.00   63
 18  \w    111.00 138.00   1.00    2.50    --  108.00 111.00-120.00   27
 19  \w     40.00 108.00   1.00    2.50    --  108.00 -77.00 -60.00   68
 20  \w     79.00 110.00   1.00    2.50    --  108.00 -94.00-180.00   31
 21  \w     39.00 128.00   1.00    2.50    --  108.00 -45.00 120.00   89
 22  \w     89.00 116.00   1.00    2.50    --  108.00 -77.00  30.00   27
 23  \w     88.00 177.00   1.00    2.50    --  108.00  30.00  60.00   89
 24  \w     38.00 109.00   1.00    2.50    --  108.00-111.00 -60.00   71
 25  \w     80.00 107.00   1.00    2.50    --  108.00 -15.00-180.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1028395000
_diffrn_orient_matrix_UB_12      -0.1277592000
_diffrn_orient_matrix_UB_13      -0.0845308000
_diffrn_orient_matrix_UB_21      -0.0653036000
_diffrn_orient_matrix_UB_22      -0.0741416000
_diffrn_orient_matrix_UB_23      0.0808538000
_diffrn_orient_matrix_UB_31      -0.2547576000
_diffrn_orient_matrix_UB_32      0.0342929000
_diffrn_orient_matrix_UB_33      0.0034053000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5607
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         4.351
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.297
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0559
_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^)+(0.1092P)^2^+0.0003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.1918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1915
_reflns_number_total             2778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00433b2.cif
_cod_data_source_block           201910251
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '444-446' was changed to
'445.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157462.cif.
;
_cod_original_cell_volume        777.92(15)
_cod_database_code               7157462
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20O4N1
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.677
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 1.877
_oxdiff_exptl_absorpt_empirical_full_min 0.739