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_4035536
_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
_chemical_name_systematic        ON-892a
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-07
_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                 95.5130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.0047(2)
_cell_length_b                   12.1799(2)
_cell_length_c                   21.4763(3)
_cell_measurement_reflns_used    7493
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.5000
_cell_measurement_theta_min      3.4920
_cell_volume                     3906.76(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_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     18.00  44.00   0.50    0.72    --    0.00  43.00  60.00   52
  2  \w    -88.00 -35.00   0.50    0.72    --    0.00  57.00  90.00  106
  3  \w    -17.00  14.00   0.50    0.72    --    0.00  43.00  60.00   62
  4  \w     50.00  84.00   0.50    0.72    --    0.00  57.00 150.00   68
  5  \w    -54.00 -28.00   0.50    2.89    --  -97.80  29.00  30.00   52
  6  \w    -38.00 -10.00   0.50    2.89    --  -97.80  43.00   0.00   56
  7  \w   -116.00 -90.00   0.50    2.89    --  -97.80  60.00  90.00   52
  8  \w   -186.00-102.00   0.50    2.89    --  -97.80   0.00   0.00  168
  9  \w   -186.00 -71.00   0.50    2.89    --  -97.80  60.00   0.00  230
 10  \w   -187.00 -42.00   0.50    2.89    --  -97.80  43.00   0.00  290
 11  \w   -184.00 -34.00   0.50    2.89    --  -97.80  14.00 150.00  300
 12  \w    -47.00  -8.00   0.50    2.89    --  -97.80  29.00   0.00   78
 13  \w   -186.00-133.00   0.50    2.89    --  -97.80  29.00   0.00  106
;
_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      -0.0384600000
_diffrn_orient_matrix_UB_12      0.0285958000
_diffrn_orient_matrix_UB_13      0.0619481000
_diffrn_orient_matrix_UB_21      -0.0478902000
_diffrn_orient_matrix_UB_22      -0.1119891000
_diffrn_orient_matrix_UB_23      -0.0011055000
_diffrn_orient_matrix_UB_31      0.0828850000
_diffrn_orient_matrix_UB_32      -0.0514140000
_diffrn_orient_matrix_UB_33      0.0367776000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9925
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.056
_diffrn_reflns_theta_min         4.136
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
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    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_preparation       'KHMDS-promoted reaction'
_exptl_crystal_recrystallization_method 'Recrystallisation from CHCl3'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0949P)^2^+2.6285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1389
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3598
_reflns_number_total             3806
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00870_si_002.cif
_cod_data_source_block           170707no
_cod_database_code               4035536
_chemical_oxdiff_formula         'C30 H19 N1'
_reflns_odcompleteness_completeness 99.56
_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:
 C30(H30), C6(H6), C12(H12), C24(H24), C28(H28), C22(H22), C21(H21), C29(H29),
 C7(H7), C27(H27), C8(H8), C23(H23), C9(H9), C11(H11), C19(H19), C18(H18),
 C15(H15), C17(H17), C16(H16)
;
_shelx_res_checksum              58330
_shelx_hkl_checksum              91653
_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 3.035
_oxdiff_exptl_absorpt_empirical_full_min 0.568