A nitrogen-based chiral catenane for enantioenriching photocatalytic aerobic oxidation
Kazem-Rostami, Masoud; New Journal of Chemistry 46 (2022) 21898–21905; doi:10.1039/D2NJ03732G

data_7062049
_publ_section_title
;
 A nitrogen-based chiral catenane for enantioenriching photocatalytic
 aerobic oxidation
;
_journal_issue                   45
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              21898
_journal_page_last               21905
_journal_paper_doi               10.1039/D2NJ03732G
_journal_volume                  46
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H36 N2 O6'
_chemical_formula_sum            'C34 H36 N2 O6'
_chemical_formula_weight         568.65
_chemical_name_common            MR524
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-27 deposited with the CCDC.	2022-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.268(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8359(4)
_cell_length_b                   8.6724(2)
_cell_length_c                   20.5944(5)
_cell_measurement_reflns_used    17420
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7650
_cell_measurement_theta_min      2.1160
_cell_volume                     2816.39(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_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   -120.00 -54.00   0.50    7.50    --  -47.44-154.00 -48.00  132
  2  \w    -92.00 -10.00   0.50    7.50    --  -47.44 120.00-167.00  164
  3  \w   -112.00 -29.00   0.50    7.50    --  -47.44 154.00  -9.00  166
  4  \w     33.00 112.00   0.50    7.50    --   47.44-154.00 -48.00  158
  5  \w     59.00 120.00   0.50    7.50    --   47.44 154.00  -9.00  122
  6  \w     29.00  54.00   0.50    7.50    --   47.44-120.00 108.00   50
  7  \w    -97.00 -53.00   0.50   24.00    -- -104.00 154.00  -9.00   88
  8  \w   -151.00-126.00   0.50   24.00    -- -104.00-120.00 108.00   50
  9  \w   -132.00-105.00   0.50   24.00    -- -104.00 154.00  -9.00   54
 10  \w   -101.00 -69.00   0.50   24.00    -- -104.00 120.00-167.00   64
 11  \w     73.00  99.00   0.50   24.00    --  110.25-120.00 108.00   52
 12  \w     39.00  89.00   0.50   24.00    --  110.25-154.00 -48.00  100
 13  \w     82.00 169.00   0.50   24.00    --  110.25 120.00-167.00  174
 14  \w   -120.00 -33.00   0.50    7.50    --  -47.44 -57.00  30.00  174
 15  \w     -7.00  22.00   0.50    7.50    --  -47.44  19.00-180.00   58
 16  \w   -118.00 -74.00   0.50    7.50    --  -47.44-125.00 -90.00   88
 17  \w    -60.00  25.00   0.50    7.50    --  -47.44  57.00 -30.00  170
 18  \w   -120.00 -74.00   0.50    7.50    --  -47.44-125.00-120.00   92
 19  \w   -114.00 -75.00   0.50    7.50    --  -47.44 -77.00  60.00   78
 20  \w    -20.00  39.00   0.50    7.50    --   47.44 -37.00 120.00  118
 21  \w    -57.00 -32.00   0.50   24.00    -- -104.00  61.00  60.00   50
 22  \w   -138.00 -92.00   0.50   24.00    -- -104.00 -48.00  10.01   92
 23  \w   -174.00 -96.00   0.50   24.00    -- -104.00 -50.00 129.84  156
 24  \w    -68.00 -34.00   0.50   24.00    -- -104.00  61.00-150.00   68
 25  \w   -173.00-145.00   0.50   24.00    -- -104.00 -62.00-153.53   56
 26  \w   -174.00-103.00   0.50   24.00    -- -104.00 -54.00  37.50  142
 27  \w   -128.00 -87.00   0.50   24.00    -- -104.00 -62.00-153.53   82
 28  \w    -91.00 -39.00   0.50   24.00    -- -104.00 144.00 173.32  104
 29  \w    -57.00 -31.00   0.50   24.00    -- -104.00 116.00 128.81   52
 30  \w    -68.00 -39.00   0.50   24.00    -- -104.00  61.00 150.00   58
 31  \w   -108.00 -36.00   0.50   24.00    -- -104.00 112.00 -98.01  144
 32  \w   -174.00-144.00   0.50   24.00    -- -104.00 -48.00  10.01   60
 33  \w    -69.00 -32.00   0.50   24.00    -- -104.00  61.00  30.00   74
 34  \w   -107.00 -79.00   0.50   24.00    -- -104.00 108.00  28.12   56
 35  \w    -67.00 -38.00   0.50   24.00    -- -104.00  61.00   0.00   58
 36  \w   -125.00 -99.00   0.50   24.00    -- -104.00 144.00 173.32   52
 37  \w   -109.00 -70.00   0.50   24.00    -- -104.00 116.00 128.81   78
 38  \w     70.00  97.00   0.50   24.00    --  110.25 -94.00 -60.00   54
 39  \w     38.00  66.00   0.50   24.00    --  110.25 -61.00  90.00   56
 40  \w     38.00  65.00   0.50   24.00    --  110.25 -94.00 -60.00   54
 41  \w    108.00 178.00   0.50   24.00    --  110.25  30.00-180.00  140
 42  \w     66.00 101.00   0.50   24.00    --  110.25-125.00 -30.00   70
 43  \w    142.00 178.00   0.50   24.00    --  110.25  61.00 -90.00   72
 44  \w     97.00 130.00   0.50   24.00    --  110.25  61.00 -90.00   66
 45  \w     45.00  70.00   0.50   24.00    --  110.25 -61.00   0.00   50
 46  \w     54.00 110.00   0.50   24.00    --  110.25-125.00-120.00  112
 47  \w     73.00 106.00   0.50   24.00    --  110.25-104.00  99.90   66
 48  \w     83.00 111.00   0.50   24.00    --  110.25-125.00  30.00   56
 49  \w    153.00 178.00   0.50   24.00    --  110.25  45.00   0.00   50
 50  \w     39.00  86.00   0.50   24.00    --  110.25 -94.00 150.00   94
 51  \w    114.00 140.00   0.50   24.00    --  110.25  45.00   0.00   52
 52  \w     47.00  73.00   0.50   24.00    --  110.25 -61.00 150.00   52
 53  \w     87.00 112.00   0.50   24.00    --  110.25 154.00  -9.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0208505000
_diffrn_orient_matrix_UB_12      0.1529818000
_diffrn_orient_matrix_UB_13      0.0360763000
_diffrn_orient_matrix_UB_21      0.0541641000
_diffrn_orient_matrix_UB_22      -0.0881149000
_diffrn_orient_matrix_UB_23      0.0537329000
_diffrn_orient_matrix_UB_31      0.0786177000
_diffrn_orient_matrix_UB_32      0.0203493000
_diffrn_orient_matrix_UB_33      -0.0380385000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40331
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.285
_diffrn_reflns_theta_min         2.802
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       needle
_exptl_crystal_F_000             1208
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.521
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.009
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 3839 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     757
_refine_ls_number_reflns         11401
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0682P)^2^+0.9971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1355
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                9697
_reflns_number_total             11401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03732g2.cif
_cod_data_source_block           MR524
_cod_depositor_comments
'Adding full bibliography for 7062048--7062052.cif.'
_cod_original_cell_volume        2816.40(13)
_cod_database_code               7062049
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C34H36N2O6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
  C25(H25A,H25B), C32(H32A,H32B), C1A(H1AA,H1AB), C2A(H2AA,H2AB), C3A(H3AA,
 H3AB), C10A(H10C,H10D), C11A(H11C,H11D), C12A(H12C,H12D), C13A(H13C,H13D),
 C22A(H22C,H22D), C23A(H23C,H23D), C24A(H24C,H24D), C25A(H25C,H25D), C32A(H32C,
 H32D)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21),
 C27(H27), C28(H28), C31(H31), C33(H33), C6A(H6A), C7A(H7A), C9A(H9A),
 C15A(H15A), C16A(H16A), C19A(H19A), C20A(H20A), C21A(H21A), C27A(H27A),
 C28A(H28A), C31A(H31A), C33A(H33A)
;
_shelx_res_checksum              45695
_olex2_date_sample_data_collection 2021-11-19
_olex2_date_sample_submission    2021-11-11
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in paratone oil'
_olex2_submission_original_sample_id MR524
_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 3.439
_oxdiff_exptl_absorpt_empirical_full_min 0.319