Chiral Brønsted acid-catalyzed dynamic kinetic resolution of atropisomeric ortho-formyl naphthamides.
Gao, Zeng; Qian, Jinlong; Yang, Huameng; Hang, Xiao-Chun; Zhang, Jinlong; Jiang, Gaoxi; Chemical communications (Cambridge, England) 56 (2020) 7265–7268; doi:10.1039/d0cc02380a

data_7126565
_publ_section_title
;
 Chiral Br\/onsted acid-catalyzed dynamic kinetic resolution of
 atropisomeric ortho-formyl naphthamides.
;
_journal_issue                   53
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7265
_journal_page_last               7268
_journal_paper_doi               10.1039/d0cc02380a
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H28 Br N3 O'
_chemical_formula_sum            'C28 H28 Br N3 O'
_chemical_formula_weight         502.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc255jjf
_audit_creation_date             2020-05-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-05-08 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.897(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3631(6)
_cell_length_b                   20.5225(9)
_cell_length_c                   11.9630(5)
_cell_measurement_reflns_used    8352
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.77
_cell_volume                     2465.6(2)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.805
_diffrn_measured_fraction_theta_max 0.822
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.1477
_diffrn_reflns_Laue_measured_fraction_full 0.805
_diffrn_reflns_Laue_measured_fraction_max 0.822
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17123
_diffrn_reflns_point_group_measured_fraction_full 0.751
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         2.258
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.692
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1927 before and 0.0748 after correction.
The Ratio of minimum to maximum transmission is 0.4619.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 1781 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.087(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     603
_refine_ls_number_reflns         8566
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0618
_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^)+(0.0762P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1632
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.693
_reflns_Friedel_fraction_max     0.687
_reflns_number_gt                5558
_reflns_number_total             8566
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02380a2.cif
_cod_data_source_block           b200427a_0m_a
_cod_depositor_comments
'Adding full bibliography for 7126565--7126566.cif.'
_cod_database_code               7126565
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.728
_shelx_estimated_absorpt_t_min   0.631
_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:
 C00G(H00G), C00O(H00O), C00P(H00P), C00T(H00T), C00Z(H00Z), C01C(H01C)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), N00A(H00A), C00F(H00F), N00H(H00H), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00U(H00U), C00V(H00V), C010(H010),
 C012(H012), C015(H015), C016(H016), C018(H018), C019(H019), C01B(H01T),
 C01F(H01F), C01H(H01V), C01I(H01I), C01J(H01J), C01N(H01N), C01Q(H01Q),
 C01R(H01R), C01U(H01U)
2.c Idealised Me refined as rotating group:
 C00X(H00B,H00C,H00D), C01K(H01A,H01B,H01D), C01L(H01W,H01X,H01Y), C01M(H01Z,H,
 HA), C01O(H01E,H01G,H01H), C01P(H01,HB,HC), C01S(H01K,H01L,H01M), C01T(H01O,
 H01P,H01S)
;
_shelx_res_checksum              70179
_olex2_submission_special_instructions 'No special instructions were received'