Chiral Derivatives of 2-Aminotribenzotriquinacene: Synthesis and Optical Resolution.
Li, Zhi-Min; Tan, Yingfei; Ma, You-Ping; Cao, Xiao-Ping; Chow, Hak-Fun; Kuck, Dietmar; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00396

data_4038303
_publ_section_title
;
 Chiral Derivatives of 2-Aminotribenzotriquinacene: Synthesis and Optical
 Resolution.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00396
_journal_year                    2020
_chemical_formula_moiety         'C28 H26 Br N O, C H Cl3'
_chemical_formula_sum            'C29 H27 Br Cl3 N O'
_chemical_formula_weight         591.77
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-03-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.729(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5810(5)
_cell_length_b                   8.4554(4)
_cell_length_c                   25.9438(11)
_cell_measurement_reflns_used    1948
_cell_measurement_temperature    293.7(3)
_cell_measurement_theta_max      23.4670
_cell_measurement_theta_min      3.9910
_cell_volume                     2720.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.7(3)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega -100.00  -64.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000 -120.0000 36

  2 omega  -92.00  -62.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000  150.0000 30

  3 omega  -10.00   23.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000   30.0000 33

  4 omega  -41.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000  -90.0000 140
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0366836000
_diffrn_orient_matrix_UB_12      0.0584524000
_diffrn_orient_matrix_UB_13      -0.0057641000
_diffrn_orient_matrix_UB_21      0.0395633000
_diffrn_orient_matrix_UB_22      -0.0288861000
_diffrn_orient_matrix_UB_23      0.0206066000
_diffrn_orient_matrix_UB_31      0.0189891000
_diffrn_orient_matrix_UB_32      -0.0527563000
_diffrn_orient_matrix_UB_33      -0.0176639000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10129
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.394
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0605
_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^)+(0.0714P)^2^+2.7362P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1681
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3583
_reflns_number_total             5351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00396_si_003.cif
_cod_data_source_block           lizm_1219_2
_cod_original_cell_volume        2720.2(2)
_cod_database_code               4038303
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C19(H19), C22(H22)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              68072
_shelx_hkl_checksum              56591
_olex2_date_sample_data_collection 2016-12-20
_olex2_submission_special_instructions 'No special instructions were received'