Synthesis and Properties of Tribenzocarbazoles via an Acid-Promoted Retro (2+2)-Cycloaddition of Azapropellanes.
Ogawa, Naoki; Yamaoka, Yousuke; Takikawa, Hiroshi; Tsubaki, Kazunori; Takasu, Kiyosei; The Journal of organic chemistry 83 (2018) 7994–8002; doi:10.1021/acs.joc.8b00870

data_4035537
_publ_section_title
;
 Synthesis and Properties of Tribenzocarbazoles via an Acid-Promoted Retro
 (2+2)-Cycloaddition of Azapropellanes.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7994
_journal_page_last               8002
_journal_paper_doi               10.1021/acs.joc.8b00870
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C30 H19 N'
_chemical_formula_sum            'C30 H19 N'
_chemical_formula_weight         393.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-02
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.283(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.9190(10)
_cell_length_b                   5.9148(2)
_cell_length_c                   26.2477(9)
_cell_measurement_reflns_used    9498
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8400
_cell_measurement_theta_min      5.7070
_cell_volume                     3842.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_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_measured_fraction_theta_full 1.000
_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    -89.00  89.00   0.50    0.91    --    0.00  29.00  60.00  356
  2  \w    -89.00 -38.00   0.50    0.91    --    0.00  60.00   0.00  102
  3  \w    -89.00 -38.00   0.50    0.91    --    0.00  60.00 150.00  102
  4  \w   -187.00  -8.00   0.50    3.63    --  -97.80   0.00   0.00  358
  5  \w   -187.00  -8.00   0.50    3.63    --  -97.80  14.00 120.00  358
  6  \w   -187.00  -8.00   0.50    3.63    --  -97.80  43.00   0.00  358
  7  \w   -187.00 -37.00   0.50    3.63    --  -97.80  60.00 150.00  300
  8  \w   -187.00 -37.00   0.50    3.63    --  -97.80  60.00   0.00  300
  9  \w   -187.00 -48.00   0.50    3.63    --  -97.80  58.00 174.07  278
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0201750000
_diffrn_orient_matrix_UB_12      -0.0931033000
_diffrn_orient_matrix_UB_13      -0.0573146000
_diffrn_orient_matrix_UB_21      0.0559113000
_diffrn_orient_matrix_UB_22      0.0459025000
_diffrn_orient_matrix_UB_23      -0.0073067000
_diffrn_orient_matrix_UB_31      0.0185413000
_diffrn_orient_matrix_UB_32      -0.2388717000
_diffrn_orient_matrix_UB_33      0.0209187000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14633
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.468
_diffrn_reflns_theta_min         3.527
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       prism
_exptl_crystal_F_000             1648
_exptl_crystal_recrystallization_method 'resrystalizzations from EtOAc'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0892P)^2^+2.9161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3429
_reflns_number_total             3780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00870_si_003.cif
_cod_data_source_block           180302no
_cod_database_code               4035537
_chemical_oxdiff_formula         'C107 H107 N107 '
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C5(H5), C10(H10), C13(H13), C31(H31), C11(H11), C4(H4), C12(H12),
 C7(H7), C23(H23), C29(H29), C19(H19), C26(H26), C6(H6), C27(H27), C21(H21),
 C22(H22), C28(H28), C20(H20)
;
_shelx_res_checksum              89792
_shelx_hkl_checksum              59855
_shelx_shelxl_version_number     2016/6
_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 1.487
_oxdiff_exptl_absorpt_empirical_full_min 0.509