Mn(III)-mediated reactions of 2-isocyanobiaryl with 1,3-dicarbonyl compounds: efficient synthesis of 6-alkylated and 6-monofluoro-alkylated phenanthridines
Jia-Jia Cao; Xiang Wang; Shun-Yi Wang; Shun-Jun Ji; Chem.Commun. 50 (2014) 12892–; doi:10.1039/C4cc05324A

data_7115810
_publ_section_title
;
 Mn(III)-mediated reactions of 2-isocyanobiaryl with 1,3-dicarbonyl
 compounds: efficient synthesis of 6-alkylated and 6-monofluoro-alkylated
 phenanthridines
;
_journal_name_full               Chem.Commun.
_journal_page_first              12892
_journal_paper_doi               10.1039/C4cc05324A
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C18 H16 F N O3'
_chemical_formula_sum            'C18 H16 F N O3'
_chemical_formula_weight         313.32
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.765(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2895(6)
_cell_length_b                   10.3789(5)
_cell_length_c                   13.6515(8)
_cell_measurement_reflns_used    5237
_cell_measurement_temperature    294.1(2)
_cell_measurement_theta_max      30.1360
_cell_measurement_theta_min      3.5760
_cell_volume                     1474.97(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      294.1(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   39.00   66.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  178.0000  -30.0000 27

  2 omega  -19.00   24.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -99.0000 -180.0000 43

  3 omega -101.00  -61.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889 -178.0000    0.0000 40

  4 omega  -79.00  -48.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -57.0000 -180.0000 31

  5 omega  -85.00   25.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -19.0000 -120.0000 110

  6 omega  -41.00   -4.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889   37.0000 -120.0000 37

  7 omega  -43.00   60.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889   49.0000  -30.0000 103
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0466894000
_diffrn_orient_matrix_UB_12      0.0101821000
_diffrn_orient_matrix_UB_13      0.0221129000
_diffrn_orient_matrix_UB_21      0.0433892000
_diffrn_orient_matrix_UB_22      0.0407987000
_diffrn_orient_matrix_UB_23      0.0392048000
_diffrn_orient_matrix_UB_31      -0.0240692000
_diffrn_orient_matrix_UB_32      0.0538921000
_diffrn_orient_matrix_UB_33      -0.0338679000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12936
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.80
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0608
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0871P)^2^+0.8771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.1904
_reflns_number_gt                2392
_reflns_number_total             3005
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc05324a2.cif
_cod_data_source_block           g140610b
_cod_original_cell_volume        1474.98(13)
_cod_database_code               7115810
_chemical_oxdiff_formula         CHNOPd
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'