Asymmetric synthesis of N-N axially chiral compounds <i>via</i> organocatalytic atroposelective <i>N</i>-acylation.
Lin, Wei; Zhao, Qun; Li, Yao; Pan, Ming; Yang, Chen; Yang, Guo-Hui; Li, Xin; Chemical science 13 (2021) 141–148; doi:10.1039/d1sc05360d

data_1565577
_publ_section_title
;
 Asymmetric synthesis of N-N axially chiral compounds <i>via</i>
 organocatalytic atroposelective <i>N</i>-acylation.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              141
_journal_page_last               148
_journal_paper_doi               10.1039/d1sc05360d
_journal_volume                  13
_journal_year                    2021
_chemical_formula_moiety         'C30 H21 N3 O3'
_chemical_formula_sum            'C30 H21 N3 O3'
_chemical_formula_weight         471.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-19 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                114.3570(10)
_cell_angle_beta                 102.2220(10)
_cell_angle_gamma                94.5930(10)
_cell_formula_units_Z            2
_cell_length_a                   9.65870(10)
_cell_length_b                   11.53350(10)
_cell_length_c                   12.42160(10)
_cell_measurement_reflns_used    26402
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      78.5470
_cell_measurement_theta_min      4.0440
_cell_volume                     1210.05(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      294.15
_diffrn_detector                 Pilatus
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.965
_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    -25.00  94.00   0.50    0.50    --    5.00  57.00  90.00  238
  2  \w   -138.00 -15.00   0.50    0.50    --  -48.80 -69.00-138.82  246
  3  \w    -82.00  41.00   0.50    0.50    --  -48.80  38.00 -30.00  246
  4  \w    -79.00  41.00   0.50    0.50    --  -48.80  57.00  60.00  240
  5  \w   -138.00 -15.00   0.50    0.50    --  -48.80 -38.00-155.54  246
  6  \w   -138.00 -16.00   0.50    0.50    --  -48.80 -64.00 -35.91  244
  7  \w   -138.00 -18.00   0.50    0.50    --  -48.80 -57.00   0.00  240
  8  \w    -82.00  41.00   0.50    0.50    --  -48.80  71.00-172.52  246
  9  \w   -138.00 -16.00   0.50    0.50    --  -48.80 -64.00 -35.91  244
 10  \w   -199.00 -78.00   0.50    1.00    -- -110.00 -64.00 -29.40  242
 11  \w   -199.00 -78.00   0.50    1.00    -- -110.00 -40.00-125.08  242
 12  \w   -199.00 -76.00   0.50    1.00    -- -110.00 -72.00 140.96  246
 13  \w   -199.00 -79.00   0.50    1.00    -- -110.00 -44.00  48.28  240
 14  \w   -199.00 -79.00   0.50    1.00    -- -110.00 -61.00  79.14  240
 15  \w   -199.00 -79.00   0.50    1.00    -- -110.00 -61.00-172.28  240
 16  \w   -199.00 -77.00   0.50    1.00    -- -110.00 -70.00  53.04  244
 17  \w   -199.00 -77.00   0.50    1.00    -- -110.00 -71.00 130.48  244
 18  \w   -103.00 -77.00   0.50    1.00    -- -110.00 -68.00-116.12   52
 19  \w   -110.00 -76.00   0.50    1.00    -- -110.00 -72.00-168.79   68
 20  \w   -104.00 -78.00   0.50    1.00    -- -110.00 -64.00 154.75   52
 21  \w   -106.00 -78.00   0.50    1.00    -- -110.00 -42.00 138.62   56
 22  \w   -102.00 -77.00   0.50    1.00    -- -110.00 -68.00 -69.96   50
 23  \w   -198.00-119.00   0.50    1.00    -- -110.00 -68.00 -69.96  158
 24  \w   -167.00-141.00   0.50    1.00    -- -110.00 -42.00 138.62   52
 25  \w   -134.00 -79.00   0.50    1.00    -- -110.00 -43.00 -98.88  110
 26  \w   -117.00 -53.00   0.50    1.00    -- -110.00 -19.00 150.00  128
 27  \w   -118.00 -80.00   0.50    1.00    -- -110.00 -38.00  60.00   76
 28  \w   -103.00 -77.00   0.50    1.00    -- -110.00 -69.00-108.66   52
 29  \w   -106.00 -21.00   0.50    1.00    -- -110.00  72.00 -60.00  170
 30  \w   -197.00 -81.00   0.50    1.00    -- -110.00 -53.00 -39.00  232
 31  \w   -135.00 -78.00   0.50    1.00    -- -110.00  72.00 -90.00  114
 32  \w   -144.00 -54.00   0.50    1.00    -- -110.00  72.00  90.00  180
 33  \w   -130.00 -65.00   0.50    1.00    -- -110.00  72.00  30.00  130
 34  \w    -58.00 -22.00   0.50    1.00    -- -110.00  72.00  30.00   72
 35  \w   -120.00 -53.00   0.50    1.00    -- -110.00 -19.00  90.00  134
 36  \w   -142.00 -21.00   0.50    1.00    -- -110.00  72.00-150.00  242
 37  \w   -102.00 -76.00   0.50    1.00    -- -110.00 -72.00-150.00   52
 38  \w   -127.00 -80.00   0.50    1.00    -- -110.00 -57.00-120.00   94
 39  \w   -104.00 -77.00   0.50    1.00    -- -110.00 -71.00 107.35   54
 40  \w   -102.00 -76.00   0.50    1.00    -- -110.00 -72.00  60.00   52
 41  \w   -199.00 -76.00   0.50    1.00    -- -110.00 -72.00 120.00  246
 42  \w   -102.00 -76.00   0.50    1.00    -- -110.00 -72.00-120.00   52
 43  \w   -198.00-135.00   0.50    1.00    -- -110.00 -65.00   7.28  126
 44  \w   -105.00 -78.00   0.50    1.00    -- -110.00 -65.00   7.28   54
 45  \w   -101.00 -76.00   0.50    1.00    -- -110.00 -72.00-180.00   50
 46  \w   -107.00 -80.00   0.50    1.00    -- -110.00 -56.00 -47.18   54
 47  \w   -185.00-129.00   0.50    1.00    -- -110.00 -72.00 -90.00  112
 48  \w   -101.00 -76.00   0.50    1.00    -- -110.00 -72.00 -90.00   50
 49  \w   -199.00-116.00   0.50    1.00    -- -110.00 -72.00   0.00  166
 50  \w   -110.00 -77.00   0.50    1.00    -- -110.00 -72.00   0.00   66
 51  \w   -101.00 -76.00   0.50    1.00    -- -110.00 -72.00 150.00   50
 52  \w   -199.00-174.00   0.50    1.00    -- -110.00 -69.00-108.66   50
 53  \w   -101.00 -76.00   0.50    1.00    -- -110.00 -72.00 -44.96   50
 54  \w   -107.00 -80.00   0.50    1.00    -- -110.00 -45.00 -30.66   54
 55  \w   -104.00 -78.00   0.50    1.00    -- -110.00 -64.00-154.35   52
 56  \w   -101.00 -76.00   0.50    1.00    -- -110.00 -72.00  40.28   50
 57  \w   -112.00 -76.00   0.50    1.00    -- -110.00 -72.00-132.09   72
 58  \w   -110.00 -77.00   0.50    1.00    -- -110.00 -38.00-120.00   66
 59  \w   -103.00 -77.00   0.50    1.00    -- -110.00 -71.00 -52.48   52
 60  \w   -113.00 -80.00   0.50    1.00    -- -110.00 -51.00-160.12   66
 61  \w   -184.00-141.00   0.50    1.00    -- -110.00 -51.00-160.12   86
 62  \w   -197.00-111.00   0.50    1.00    -- -110.00 -72.00  40.28  172
 63  \w   -176.00-151.00   0.50    1.00    -- -110.00 -38.00  60.00   50
 64  \w   -172.00 -80.00   0.50    1.00    -- -110.00 -51.00  46.45  184
 65  \w   -103.00 -77.00   0.50    1.00    -- -110.00 -72.00 -30.00   52
 66  \w   -103.00 -82.50   0.50    1.00    -- -110.00 -70.00  82.11   41
 67  \w   -106.00 -80.00   0.50    1.00    -- -110.00 -57.00 -30.00   52
 68  \w   -106.00 -80.00   0.50    1.00    -- -110.00 -49.00   3.97   52
 69  \w   -105.00 -80.00   0.50    1.00    -- -110.00 -59.00 -95.54   50
 70  \w   -154.00-129.00   0.50    1.00    -- -110.00 -72.00-132.09   50
 71  \w   -122.00 -77.00   0.50    1.00    -- -110.00 -38.00 -90.00   90
 72  \w   -108.00 -79.00   0.50    1.00    -- -110.00 -62.00  12.00   58
 73  \w   -130.00 -72.00   0.50    1.00    -- -110.00  72.00   0.00  116
 74  \w   -191.00-165.00   0.50    1.00    -- -110.00 -43.00 -98.88   52
 75  \w   -106.00 -80.00   0.50    1.00    -- -110.00 -51.00  18.23   52
 76  \w   -108.00 -80.00   0.50    1.00    -- -110.00 -60.00  53.55   56
 77  \w   -106.00 -80.00   0.50    1.00    -- -110.00 -59.00  -8.94   52
 78  \w   -192.00-161.00   0.50    1.00    -- -110.00 -19.00  90.00   62
 79  \w   -155.00-130.00   0.50    1.00    -- -110.00 -19.00  90.00   50
 80  \w   -130.00 -72.00   0.50    1.00    -- -110.00 -29.00 -10.87  116
 81  \w   -179.00-153.00   0.50    1.00    -- -110.00 -29.00 -10.87   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0405367000
_diffrn_orient_matrix_UB_12      -0.0503506000
_diffrn_orient_matrix_UB_13      0.0975075000
_diffrn_orient_matrix_UB_21      -0.0780832000
_diffrn_orient_matrix_UB_22      -0.1375867000
_diffrn_orient_matrix_UB_23      -0.0957591000
_diffrn_orient_matrix_UB_31      0.1409603000
_diffrn_orient_matrix_UB_32      -0.0286507000
_diffrn_orient_matrix_UB_33      -0.0361727000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            40355
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.155
_diffrn_reflns_theta_min         4.057
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0657P)^2^+0.1374P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4726
_reflns_number_total             5058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05360d2.cif
_cod_data_source_block           p20201106a
_cod_depositor_comments          'Adding full bibliography for 1565577.cif.'
_cod_database_code               1565577
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.875
_reflns_odcompleteness_completeness 97.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
;
_shelx_res_checksum              49078
_shelx_hkl_checksum              24485
_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 4.631
_oxdiff_exptl_absorpt_empirical_full_min 0.700