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_7062052
_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 syn
_chemical_formula_moiety         'C36 H32 N4, C34 H37 N2 O6, 4(F6 P)'
_chemical_formula_sum            'C70 H69 F24 N6 O6 P4'
_chemical_formula_weight         1670.19
_chemical_melting_point          ?
_chemical_name_common            'SS-TBDR34C6 . BlueBox . 4PF6'
_chemical_name_systematic
'(2S,4aR,5S,6aS,22S,25aS,26S)-dodecahydro-1H,6H-2,8-(epoxyethanooxyethanooxy[1,5]naphthalenooxyethanooxyethanooxy)-5,11-ethanodibenzo[b,f][1,5]diazocine.1,2,7(4,1),6(1,4)-tetrapyridin-1-iuma-4,9(1,4)-dibenzenacyclodecaphane-11,21,61,71-tetraium.tetrakis hexafluorophosphate'
_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             2021-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-10 deposited with the CCDC.	2022-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.980(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1062(3)
_cell_length_b                   25.2825(7)
_cell_length_c                   24.5285(8)
_cell_measurement_reflns_used    24933
_cell_measurement_temperature    250.00(10)
_cell_measurement_theta_max      75.0340
_cell_measurement_theta_min      3.4800
_cell_volume                     8742.6(4)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.00(10)
_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 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    -74.00   7.00   0.50   15.00    --  -47.48 102.00 165.00  162
  2  \w     15.00  82.00   0.50   15.00    --   47.48-102.00  61.00  134
  3  \w    -14.00  12.00   0.50   15.00    --   47.48-102.00  61.00   52
  4  \w   -121.00 -95.00   0.50   50.00    -- -106.00-102.00  61.00   52
  5  \w   -174.00-134.00   0.50   50.00    -- -106.00-102.00  61.00   80
  6  \w     69.00 105.00   0.50   50.00    --  113.25-102.00  61.00   72
  7  \w    -21.00  12.00   0.50   15.00    --  -47.48  19.00  60.00   66
  8  \w   -117.00 -73.00   0.50   15.00    --  -47.48-125.00-150.00   88
  9  \w   -109.00 -79.00   0.50   15.00    --  -47.48-125.00-120.00   60
 10  \w   -108.00 -77.00   0.50   15.00    --  -47.48-125.00 -60.00   62
 11  \w    -40.00 -14.00   0.50   15.00    --  -47.48  37.00  60.00   52
 12  \w     -4.00  22.00   0.50   15.00    --  -47.48  37.00  60.00   52
 13  \w    -20.00  28.00   0.50   15.00    --  -47.48  19.00-150.00   96
 14  \w    -27.00  14.00   0.50   15.00    --   47.48 -19.00  60.00   82
 15  \w    -19.00  58.00   0.50   15.00    --   47.48 -57.00 120.00  154
 16  \w    -27.00  17.00   0.50   15.00    --   47.48 -19.00 -90.00   88
 17  \w    -71.00 -34.00   0.50   50.00    -- -106.00  61.00 120.00   74
 18  \w    -71.00 -36.00   0.50   50.00    -- -106.00  61.00 -30.00   70
 19  \w    -74.00 -49.00   0.50   50.00    -- -106.00  61.00  30.00   50
 20  \w   -112.00 -38.00   0.50   50.00    -- -106.00 125.00 -30.00  148
 21  \w    -66.00 -40.00   0.50   50.00    -- -106.00  61.00 -60.00   52
 22  \w    -70.00 -35.00   0.50   50.00    -- -106.00 111.00  91.45   70
 23  \w   -105.00 -76.00   0.50   50.00    -- -106.00 102.00 165.00   58
 24  \w   -174.00 -87.00   0.50   50.00    -- -106.00 -77.00 -60.00  174
 25  \w   -176.00-119.00   0.50   50.00    -- -106.00 -45.00   0.00  114
 26  \w   -110.00 -33.00   0.50   50.00    -- -106.00 125.00  90.00  154
 27  \w    -72.00 -47.00   0.50   50.00    -- -106.00  61.00   0.00   50
 28  \w    -73.00 -34.00   0.50   50.00    -- -106.00 125.00 -60.00   78
 29  \w   -112.00 -86.00   0.50   50.00    -- -106.00 125.00 -60.00   52
 30  \w   -175.00-118.00   0.50   50.00    -- -106.00 -45.00 -30.00  114
 31  \w   -108.00 -83.00   0.50   50.00    -- -106.00 111.00  91.45   50
 32  \w     43.00  68.00   0.50   50.00    --  113.25 -61.00 -90.00   50
 33  \w    101.00 178.00   0.50   50.00    --  113.25  61.00   0.00  154
 34  \w     46.00  92.00   0.50   50.00    --  113.25-125.00-150.00   92
 35  \w    101.00 178.00   0.50   50.00    --  113.25  30.00-120.00  154
 36  \w     42.00  67.00   0.50   50.00    --  113.25 -61.00  60.00   50
 37  \w     85.00 111.00   0.50   50.00    --  113.25-125.00 -90.00   52
 38  \w     43.00  70.00   0.50   50.00    --  113.25 -61.00-150.00   54
 39  \w     46.00  71.00   0.50   50.00    --  113.25 -61.00 150.00   50
 40  \w     62.00 106.00   0.50   50.00    --  113.25 -94.00-120.00   88
 41  \w    152.00 177.00   0.50   50.00    --  113.25   0.00 -30.00   50
 42  \w    120.00 178.00   0.50   50.00    --  113.25  15.00 120.00  116
 43  \w     51.00  96.00   0.50   50.00    --  113.25-125.00 120.00   90
 44  \w    122.00 174.00   0.50   50.00    --  113.25   0.00-180.00  104
 45  \w    130.00 171.00   0.50   50.00    --  113.25 102.00 165.00   82
;
_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      0.0201810000
_diffrn_orient_matrix_UB_12      -0.0235112000
_diffrn_orient_matrix_UB_13      0.0571676000
_diffrn_orient_matrix_UB_21      -0.0260718000
_diffrn_orient_matrix_UB_22      0.0532886000
_diffrn_orient_matrix_UB_23      0.0260084000
_diffrn_orient_matrix_UB_31      -0.1041996000
_diffrn_orient_matrix_UB_32      -0.0178923000
_diffrn_orient_matrix_UB_33      0.0022268000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1341
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            103015
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         3.496
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66085
_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            Maroon
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       Plate
_exptl_crystal_F_000             3420
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeCN / H2O'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details
;
 Flack x determined using 7435 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(2)
_refine_ls_extinction_coef       0.0032(3)
_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   1.256
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1982
_refine_ls_number_reflns         31872
_refine_ls_number_restraints     2600
_refine_ls_restrained_S_all      1.255
_refine_ls_R_factor_all          0.1463
_refine_ls_R_factor_gt           0.1291
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3292
_refine_ls_wR_factor_ref         0.3460
_reflns_Friedel_coverage         0.945
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                22932
_reflns_number_total             31872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03732g2.cif
_cod_data_source_block           MR572S
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'NA' was changed to '?' --
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7062048--7062052.cif.
;
_cod_database_code               7062052
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C71H12$N6O6P4F24
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.811
_diffrn_oxdiff_digest_frames
;
01bcb40ea145faa98cb380e7e08a5aea0203846f9c9
;
_diffrn_oxdiff_digest_hkl
;
0158d5d13e5c947cf2a85aafc853d4494c30f4
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 F37-F41 \\sim F37-F39 \\sim F37-F40 \\sim F37-F42 \\sim F41-F40 \\sim F41-F42
\\sim F41-F38 \\sim F39-F40
 \\sim F39-F42 \\sim F39-F38 \\sim F42-F38
 with sigma of 0.02
 P7-F37 \\sim P7-F41 \\sim P7-F39 \\sim P7-F40 \\sim P7-F42 \\sim P7-F38
 with sigma of 0.01
 F26-F28 \\sim F26-F29 \\sim F26-F30 \\sim F26-F27 \\sim F25-F28 \\sim F25-F29
\\sim F25-F30 \\sim F25-F27
 \\sim F28-F29 \\sim F28-F27 \\sim F29-F30 \\sim F30-F27
 with sigma of 0.02
 P5-F26 \\sim P5-F25 \\sim P5-F28 \\sim P5-F29 \\sim P5-F30 \\sim P5-F27
 with sigma of 0.01
 F36-F32 \\sim F36-F35 \\sim F36-F31 \\sim F36-F33 \\sim F34-F32 \\sim F34-F35
\\sim F34-F31 \\sim F34-F33
 \\sim F32-F35 \\sim F32-F33 \\sim F35-F31
 with sigma of 0.02
 P6-F36 \\sim P6-F34 \\sim P6-F32 \\sim P6-F35 \\sim P6-F31 \\sim P6-F33
 with sigma of 0.01
 N6A-C45A \\sim N5A-C44A \\sim N6-C46 \\sim N6-C45 \\sim N5-C44 \\sim N5-C48
\\sim N5-C43 \\sim N6-C40 ~
 N5A-C48A \\sim N5A-C43A \\sim N6A-C40A \\sim N6A-C46A
 with sigma of 0.01
 C38-C37 \\sim C39-C38 \\sim C40-C39 \\sim C41-C40 \\sim C42-C41 \\sim C42-C37
 with sigma of 0.01
 O2A-C55A \\sim O3A-C56A \\sim O2A-C54A \\sim O1A-C53A \\sim O6A-C37A \\sim
O6A-C70A \\sim O5A-C69A ~
 O5A-C68A \\sim O1-C51 \\sim O1-C53 \\sim O2-C54 \\sim O2-C55 \\sim O3-C56
\\sim O3-C57 \\sim O4-C62 \\sim O4-
 C67 \\sim O5-C68 \\sim O5-C69 \\sim O6-C70 \\sim O6-C37
 with sigma of 0.01
 C70A-C69A \\sim C68A-C67A \\sim C56A-C55A \\sim C54A-C53A \\sim C56-C55 \\sim
C68-C67 \\sim C70-C69 ~
 C54-C53
 with sigma of 0.01
 C6A-C5A \\sim C5A-C4A \\sim C4A-C3A \\sim C3A-C2A \\sim C11A-C10A \\sim
C7A-C11A \\sim C8A-C7A \\sim C9A-
 C8A \\sim C24A-C23A \\sim C23A-C22A \\sim C22A-C21A \\sim C21A-C20A \\sim
C29A-C28A \\sim C29A-C25A ~
 C26A-C25A \\sim C27A-C26A \\sim C50A-C49A \\sim C49A-C48A \\sim C48A-C47A
\\sim C52A-C47A \\sim C52A-
 C51A \\sim C51A-C50A
 with sigma of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 N6(H6), N5A(H5A)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B), C19(H19A,H19B), C30(H30A,H30B), C43(H43A,H43B),
 C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C53(H53A,H53B), C54(H54A,H54B),
  C55(H55A,H55B), C56(H56A,H56B), C67(H67A,H67B), C68(H68A,H68B), C69(H69A,
 H69B), C70(H70A,H70B), C1A(H1AA,H1AB), C12A(H12C,H12D), C19A(H19C,H19D),
 C30A(H30C,H30D), C43A(H43C,H43D), C44A(H44C,H44D), C45A(H45C,H45D), C46A(H46C,
 H46D), C53A(H53C,H53D), C54A(H54C,H54D), C55A(H55C,H55D), C56A(H56C,H56D),
 C67A(H67C,H67D), C68A(H68C,H68D), C69A(H69C,H69D), C70A(H70C,H70D)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6A), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
  C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24),
 C26(H26), C27(H27), C28(H28), C29(H29), C32(H32), C33(H33), C35(H35), C36(H36),
  C38(H38), C41(H41), C42(H42), C49(H49), C50(H50), C52(H52), C58(H58),
 C59(H59), C60(H60), C63(H63), C64(H64), C65(H65), C2A(H2A), C3A(H3A),
 C5A(H5AA), C6A(H6AA), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A), C14A(H14A),
 C15A(H15A), C17A(H17A), C18A(H18A), C20A(H20A), C21A(H21A), C23A(H23A),
 C24A(H24A), C26A(H26A), C27A(H27A), C28A(H28A), C29A(H29A), C32A(H32A),
 C33A(H33A), C35A(H35A), C36A(H36A), C38A(H38A), C41A(H41A), C42A(H42A),
 C49A(H49A), C50A(H50A), C52A(H52A), C58A(H58A), C59A(H59A), C60A(H60A),
 C63A(H63A), C64A(H64A), C65A(H65A)
;
_shelx_res_checksum              5374
_shelx_fab_checksum              81495
_olex2_date_sample_data_collection 2021-12-07
_olex2_date_sample_submission    2021-12-06
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with Paratone oil'
_olex2_submission_original_sample_id MR572S
_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 2.180
_oxdiff_exptl_absorpt_empirical_full_min 0.545