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_7062048
_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         'C18 H13 O8, C16 H17 N2, C3 H6 O'
_chemical_formula_sum            'C37 H36 N2 O9'
_chemical_formula_weight         652.68
_chemical_name_systematic
'(5S,11S)-6H,12H-5,11-ethano dibenzo[b,f][1,5]diazocine . (-)-O,O'-Dibenzoyl-L-tartaric acid'
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Heat-sensitive,Oxygen-sensitive,Light-sensitive
_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             2020-05-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-07 deposited with the CCDC.	2022-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.31750(10)
_cell_length_b                   11.86530(10)
_cell_length_c                   25.2383(2)
_cell_measurement_reflns_used    14679
_cell_measurement_temperature    199.91(17)
_cell_measurement_theta_max      76.2800
_cell_measurement_theta_min      3.4880
_cell_volume                     3389.14(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.91(17)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_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    -35.00  24.00   0.50    1.00    --  -48.95  36.00 -15.00  118
  2  \w   -107.00 -73.00   0.50    1.00    --  -48.95-125.00 129.00   68
  3  \w   -171.00-132.00   0.50    3.00    -- -105.86 -85.00  17.00   78
  4  \w   -177.00-101.00   0.50    3.00    -- -105.86 -36.00-171.00  152
  5  \w     76.00 175.00   0.50    3.00    --  105.86 125.00-152.00  198
  6  \w    -42.00 -12.00   0.50    1.00    --  -48.95  37.00  90.00   60
  7  \w   -122.00 -73.00   0.50    1.00    --  -48.95-125.00 -90.00   98
  8  \w    -19.00  18.00   0.50    1.00    --   48.95 -19.00  90.00   74
  9  \w    -16.00  13.00   0.50    1.00    --   48.95 -19.00  30.00   58
 10  \w     88.00 113.00   0.50    1.00    --   48.95 125.00-152.00   50
 11  \w    -71.00 -45.00   0.50    3.00    -- -105.86  61.00   0.00   52
 12  \w    -74.00 -34.00   0.50    3.00    -- -105.86  61.00 -30.00   80
 13  \w     36.00  62.00   0.50    3.00    --  105.86 -61.00 150.00   52
 14  \w     42.00  71.00   0.50    3.00    --  105.86 -61.00 -30.00   58
 15  \w     38.00 105.00   0.50    3.00    --  105.86 -94.00 120.00  134
 16  \w    149.00 178.00   0.50    3.00    --  105.86  15.00  90.00   58
 17  \w    123.00 175.00   0.50    3.00    --  105.86  15.00 120.00  104
 18  \w     44.00  71.00   0.50    3.00    --  105.86 -61.00-150.00   54
 19  \w     97.00 144.00   0.50    3.00    --  105.86  15.00  90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0029013000
_diffrn_orient_matrix_UB_12      0.0274882000
_diffrn_orient_matrix_UB_13      -0.0596272000
_diffrn_orient_matrix_UB_21      0.0632903000
_diffrn_orient_matrix_UB_22      0.1121358000
_diffrn_orient_matrix_UB_23      0.0120544000
_diffrn_orient_matrix_UB_31      0.1204693000
_diffrn_orient_matrix_UB_32      -0.0594707000
_diffrn_orient_matrix_UB_33      -0.0048703000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20030
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.839
_diffrn_reflns_theta_min         3.502
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.63a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.279
_exptl_crystal_description       tabular
_exptl_crystal_F_000             1376
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.078
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 2570 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(7)
_refine_ls_extinction_coef       0.00104(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         6840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0406P)^2^+0.2847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                6293
_reflns_number_total             6840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03732g2.cif
_cod_data_source_block           cx1883
_cod_depositor_comments
'Adding full bibliography for 7062048--7062052.cif.'
_cod_database_code               7062048
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C10H16N2
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.943
_diffrn_oxdiff_digest_frames
;
018dbf239d9c9616b99b772869885c03ff016402a1b
;
_diffrn_oxdiff_digest_hkl
;
01b8564db76630e86570fa261219eb962f97dc
;
_reflns_odcompleteness_completeness 100.00
_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. Others
 Sof(O1T)=Sof(C1T)=Sof(H1TA)=Sof(H1TB)=Sof(H1TC)=Sof(C2T)=Sof(C3T)=Sof(H3TA)=
 Sof(H3TB)=Sof(H3TC)=1-FVAR(1)
 Sof(O1S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(H1SC)=Sof(C2S)=Sof(C3S)=Sof(H3SA)=
 Sof(H3SB)=Sof(H3SC)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C27(H27A,H27B), C34(H34A,H34B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C29(H29), C30(H30),
  C31(H31), C32(H32)
3.d Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C1T(H1TA,H1TB,H1TC), C3S(H3SA,H3SB,H3SC), C3T(H3TA,H3TB,
 H3TC)
;
_shelx_res_checksum              81443
_olex2_date_sample_data_collection 2020-05-25
_olex2_date_sample_submission    2020-05-25
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a glass fibre with Paratone oil'
_olex2_submission_original_sample_id cx1883
_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 1.091
_oxdiff_exptl_absorpt_empirical_full_min 0.934