Atroposelective synthesis of configurationally stable nonbiaryl N-C atropisomers through direct asymmetric aminations of 1,3-benzenediamines.
Wang, Donglei; Jiang, Qianwen; Yang, Xiaoyu; Chemical communications (Cambridge, England) 56 (2020) 6201–6204; doi:10.1039/d0cc02368j

data_7126448
_publ_section_title
;
 Atroposelective synthesis of configurationally stable nonbiaryl N-C
 atropisomers through direct asymmetric aminations of 1,3-benzenediamines.
;
_journal_issue                   46
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6201
_journal_page_last               6204
_journal_paper_doi               10.1039/d0cc02368j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C31 H38 N4 O5'
_chemical_formula_sum            'C31 H38 N4 O5'
_chemical_formula_weight         546.65
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-06
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-03-07 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1246(3)
_cell_length_b                   16.0039(5)
_cell_length_c                   18.3736(6)
_cell_measurement_reflns_used    9548
_cell_measurement_temperature    149.99
_cell_measurement_theta_max      78.80
_cell_measurement_theta_min      5.17
_cell_volume                     2977.13(16)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      149.99
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            61146
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.180
_diffrn_reflns_theta_min         3.663
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.6297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1259 before and 0.0786 after correction.
The Ratio of minimum to maximum transmission is 0.8349.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2437 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         6406
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0496P)^2^+0.9135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                5918
_reflns_number_total             6406
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02368j2.cif
_cod_data_source_block           cu_wdl6_55_0m
_cod_depositor_comments          'Adding full bibliography for 7126448.cif.'
_cod_database_code               7126448
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.936
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
3.a Rotating group:
 N00B(H00A,H00B)
3.b Secondary CH2 refined with riding coordinates:
 C00Z(H00X,H00Z), C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 N007(H007), N008(H008), C00I(H00I), C00J(H00J), C00O(H00O), C00Y(H00Y),
 C010(H010), C012(H012), C014(H014), C2(H2), C3(H3), C7(H7), C6(H6), C5(H5)
3.d Idealised Me refined as rotating group:
 C00N(H00C,H00D,H00E), C00P(H00F,H00G,H00H), C00Q(H00K,H00L,H00M), C00R(H00N,
 H00P,H00Q), C00S(H00R,H00S,H00T), C00X(H00U,H00V,H00W)
;
_shelx_res_checksum              57952
_olex2_submission_special_instructions 'No special instructions were received'