Catalytic Asymmetric Synthesis of Chiral Covalent Organic Frameworks from Prochiral Monomers for Heterogeneous Asymmetric Catalysis.
Wang, Jian-Cheng; Kan, Xuan; Shang, Jin-Yan; Qiao, Hua; Dong, Yu-Bin; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c07461

data_4135258
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Chiral Covalent Organic Frameworks from
 Prochiral Monomers for Heterogeneous Asymmetric Catalysis.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c07461
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H19 N O4'
_chemical_formula_sum            'C15 H19 N O4'
_chemical_formula_weight         277.31
_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   geom
_audit_creation_date             2020-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7066(4)
_cell_length_b                   8.4577(6)
_cell_length_c                   30.146(2)
_cell_measurement_reflns_used    1207
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.4270
_cell_measurement_theta_min      5.8860
_cell_volume                     1454.99(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_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    -19.00  37.00   1.00    1.00    --    0.00  77.00  30.00   56
  2  \w      6.00  33.00   1.00    1.00    --    0.00  77.00-150.00   27
  3  \w     98.00 124.00   1.00    1.00    --   54.00  77.00-180.00   26
  4  \w     46.00  84.00   1.00    1.00    --   54.00  77.00-180.00   38
  5  \w     25.00  57.00   1.00    1.00    --   54.00  77.00  90.00   32
  6  \w     34.00 106.00   1.00    1.00    --   54.00  77.00-120.00   72
  7  \w    100.00 170.00   1.00    1.00    --  108.00  77.00-150.00   70
  8  \w    129.00 171.00   1.00    1.00    --  108.00  77.00-180.00   42
  9  \w    110.00 177.00   1.00    1.00    --  108.00  77.00  60.00   67
 10  \w     97.00 125.00   1.00    1.00    --  108.00  77.00-180.00   28
 11  \w     85.00 164.00   1.00    1.00    --  108.00  77.00 -60.00   79
 12  \w     84.00 109.00   1.00    1.00    --  108.00  77.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0477133000
_diffrn_orient_matrix_UB_12      -0.0302891000
_diffrn_orient_matrix_UB_13      -0.0495750000
_diffrn_orient_matrix_UB_21      0.1784106000
_diffrn_orient_matrix_UB_22      0.1367379000
_diffrn_orient_matrix_UB_23      -0.0004053000
_diffrn_orient_matrix_UB_31      0.1968061000
_diffrn_orient_matrix_UB_32      -0.1165894000
_diffrn_orient_matrix_UB_33      0.0123661000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            3371
_diffrn_reflns_point_group_measured_fraction_full 0.863
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        65.989
_diffrn_reflns_theta_max         65.989
_diffrn_reflns_theta_min         2.932
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 456 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0546P)^2^+0.0336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.442
_reflns_Friedel_fraction_full    0.657
_reflns_Friedel_fraction_max     0.658
_reflns_number_gt                1806
_reflns_number_total             2181
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c07461_si_002.cif
_cod_data_source_block           exp_3778
_cod_original_cell_volume        1454.97(19)
_cod_database_code               4135258
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.921
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              56064
_shelx_hkl_checksum              48511
_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 1.309
_oxdiff_exptl_absorpt_empirical_full_min 0.805