A Facile Access to Substituted Cationic 12-Azapyrene Salts by Rhodium(III)-Catalyzed C–H Annulation of N-Arylpyridinium Salts
Feng, Boya; Wan, Danyang; Yan, Lipeng; Kadam, Vilas D.; You, Jingsong; Gao, Ge; RSC Adv.  (2016) –; doi:10.1039/C6RA15464F

data_7225876
_publ_section_title
;
 A Facile Access to Substituted Cationic 12-Azapyrene Salts by
 Rhodium(III)-Catalyzed C--H Annulation of N-Arylpyridinium Salts
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA15464F
_journal_year                    2016
_chemical_formula_moiety         'C91 H70 N5, B F4'
_chemical_formula_sum            'C91 H70 B F4 N5'
_chemical_formula_weight         1320.33
_chemical_name_systematic
'2-(tert-Butyl)-4,5,9,10-tetrakis(4-(diphenylamino)phenyl)quinolizino[3,4,5,6-ija]quinolin-11-ium tetrafluoroborate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_Hall           '-P 2c 2b'
_space_group_name_H-M_alt        'P b c m'
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-09 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9314(5)
_cell_length_b                   15.0022(4)
_cell_length_c                   44.7410(12)
_cell_measurement_reflns_used    6258
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6080
_cell_measurement_theta_min      4.2020
_cell_volume                     8679.7(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega    1.00   74.50   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -150.0000 98

  2 omega    1.00   74.50   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000   30.0000 98

  3 omega  -31.00   62.00   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000 -150.0000 124

  4 omega   23.00   89.00   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000    0.0000 88

  5 omega   20.00  104.00   0.7500    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -90.0000 112

  6 omega   40.00   97.00   0.7500   47.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 76

  7 omega   38.00   90.50   0.7500   47.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 70

  8 omega   38.00   83.00   0.7500   47.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 60

  9 omega   43.00   85.00   0.7500   47.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 56

 10 omega   54.00   94.50   0.7500   47.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 54

 11 omega   48.00   75.00   0.7500   47.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 36

 12 omega   91.00  127.00   0.7500   47.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0392356000
_diffrn_orient_matrix_UB_12      0.0607397000
_diffrn_orient_matrix_UB_13      -0.0253634000
_diffrn_orient_matrix_UB_21      0.1015376000
_diffrn_orient_matrix_UB_22      -0.0152192000
_diffrn_orient_matrix_UB_23      -0.0172527000
_diffrn_orient_matrix_UB_31      -0.0482398000
_diffrn_orient_matrix_UB_32      -0.0814129000
_diffrn_orient_matrix_UB_33      -0.0156714000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            26234
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.621
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.010
_exptl_crystal_description       plate
_exptl_crystal_F_000             2768
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0733
_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^)+(0.1600P)^2^+0.1670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2271
_refine_ls_wR_factor_ref         0.2447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5247
_reflns_number_total             7850
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra15464f2.cif
_cod_data_source_block           fby1208
_cod_database_code               7225876
_reflns_odcompleteness_completeness 99.66
_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. Others
 Fixed Sof: H01G(0.5) H01H(0.5) H01I(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C010(H010), C011(H011), C012(H012), C013(H013), C014(H014), C015(H015),
 C016(H016), C017(H017), C018(H018), C019(H019), C01A(H01A), C01B(H01B),
 C01D(H01D)
3.b Idealised Me refined as rotating group:
 C01H(H01C,H01E,H01F), C01J(H01G,H01H,H01I)
;
_shelx_res_checksum              29402
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-08
_olex2_submission_special_instructions 'No special instructions were received'