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_4038302
_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_absolute_configuration ad
_chemical_formula_moiety         'C32 H33 N O4, C2 H6.35 O S'
_chemical_formula_sum            'C34 H39.35 N O5 S'
_chemical_formula_weight         574.07
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 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                71.654(4)
_cell_angle_beta                 88.192(4)
_cell_angle_gamma                88.920(4)
_cell_formula_units_Z            1
_cell_length_a                   6.3532(8)
_cell_length_b                   11.1522(14)
_cell_length_c                   11.6114(15)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.14
_cell_measurement_theta_min      6.97
_cell_volume                     780.45(17)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_unetI/netI     0.1026
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18982
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.089
_diffrn_reflns_theta_min         6.973
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1192 before and 0.0808 after correction.
The Ratio of minimum to maximum transmission is 0.7893.
The \l/2 correction factor is Not present.
;
_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    1.221
_exptl_crystal_description       block
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1795 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.059(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5465
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0422P)^2^+0.1479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    0.835
_reflns_Friedel_fraction_max     0.814
_reflns_number_gt                4490
_reflns_number_total             5465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00396_si_002.cif
_cod_data_source_block           lizhm_0912_0m
_cod_database_code               4038302
_shelx_shelxl_version_number     2018/3
_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, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 C34-S1 \\sim C34A-S1
 with sigma of 0.02
 C34-S1' \\sim C34A-S1'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C34) \\sim Ueq, Uanis(C34A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.005
4. Others
 Fixed Sof: H5A(0.35) H33A(0.65) H33B(0.65) H33C(0.65) H33D(0.35) H33E(0.35)
 H33F(0.35) C34(0.35) H34A(0.35) H34B(0.35) H34C(0.35) S1(0.65) S1'(0.35)
 C34A(0.65) H34D(0.65) H34E(0.65) H34F(0.65)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16),
 C17(H17), C18(H18), C19(H19)
5.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,
 H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,
 H33B,H33C), C33(H33D,H33E,H33F), C34(H34A,H34B,H34C), C34A(H34D,H34E,H34F)
5.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5A)
;
_shelx_res_checksum              39123
_shelx_hkl_checksum              8738
_olex2_submission_special_instructions 'No special instructions were received'