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_7062050
_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_formula_moiety
'4(F6 P), C34 H36 N2 O6, H2 O, C36 H32 N4, C2 H3 N'
_chemical_formula_sum            'C72 H73 F24 N7 O7 P4'
_chemical_formula_weight         1728.25
_chemical_melting_point          ?
_chemical_name_common            MR530
_chemical_name_systematic
'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           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-29
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2021-12-30 deposited with the CCDC.	2022-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.2222(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9868(3)
_cell_length_b                   22.2742(4)
_cell_length_c                   23.3991(5)
_cell_measurement_reflns_used    18089
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      77.1540
_cell_measurement_theta_min      2.7160
_cell_volume                     7270.1(3)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(11)
_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 0.959
_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   -121.00 -48.00   0.50   11.42    --  -47.69  -4.00 -41.00  146
  2  \w    -33.00  -8.00   0.50   11.42    --  -47.69   4.00 136.00   50
  3  \w    -14.00  11.00   0.50   11.42    --   47.69  -4.00 -41.00   50
  4  \w    -92.00 -66.00   0.50   45.69    -- -104.00  -4.00 -41.00   52
  5  \w   -154.00 -93.00   0.50   45.69    -- -104.00  -4.00 -41.00  122
  6  \w     62.00 162.00   0.50   45.69    --  110.25   4.00 136.00  200
  7  \w    -37.00  13.00   0.50   11.42    --  -47.69  37.00 -90.00  100
  8  \w     11.00 117.00   0.50   11.42    --   47.69   4.00 136.00  212
  9  \w     44.00  93.00   0.50   11.42    --   47.69-125.00 -60.00   98
 10  \w   -111.00 -85.00   0.50   45.69    -- -104.00 125.00-180.00   52
 11  \w   -112.00 -78.00   0.50   45.69    -- -104.00 125.00-150.00   68
 12  \w   -108.00 -39.00   0.50   45.69    -- -104.00 111.00 171.47  138
 13  \w    -69.00 -34.00   0.50   45.69    -- -104.00  61.00 -90.00   70
 14  \w    -68.00 -41.00   0.50   45.69    -- -104.00  61.00 -60.00   54
 15  \w    -69.00 -43.00   0.50   45.69    -- -104.00  61.00-180.00   52
 16  \w     44.00  73.00   0.50   45.69    --  110.25 -61.00 -90.00   58
 17  \w     38.00  72.00   0.50   45.69    --  110.25 -61.00 120.00   68
 18  \w     96.00 177.00   0.50   45.69    --  110.25  77.00   0.00  162
 19  \w     80.00 106.00   0.50   45.69    --  110.25 -94.00 -90.00   52
 20  \w     79.00 106.00   0.50   45.69    --  110.25 -94.00-120.00   54
 21  \w     39.00 105.00   0.50   45.69    --  110.25 -94.00-180.00  132
 22  \w     44.00  69.00   0.50   45.69    --  110.25 -94.00-120.00   50
 23  \w     48.00  73.00   0.50   45.69    --  110.25 -61.00 -30.00   50
 24  \w     38.00  86.00   0.50   45.69    --  110.25 -77.00  90.00   96
 25  \w     81.00 106.00   0.50   45.69    --  110.25 -94.00   0.00   50
 26  \w     38.00  71.00   0.50   45.69    --  110.25 -94.00 -90.00   66
;
_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      -0.0279654000
_diffrn_orient_matrix_UB_12      -0.0027763000
_diffrn_orient_matrix_UB_13      -0.0648718000
_diffrn_orient_matrix_UB_21      -0.1067384000
_diffrn_orient_matrix_UB_22      -0.0026722000
_diffrn_orient_matrix_UB_23      0.0120664000
_diffrn_orient_matrix_UB_31      -0.0053001000
_diffrn_orient_matrix_UB_32      0.0690444000
_diffrn_orient_matrix_UB_33      -0.0019981000
_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  0.0689
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            56425
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.834
_diffrn_reflns_theta_min         2.742
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.054
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48039
_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            black-purple
_exptl_crystal_colour_primary    black-purple
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_description       plate
_exptl_crystal_F_000             3544
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile/Water'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.002
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.913
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.00036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1054
_refine_ls_number_reflns         15052
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0658
_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^)+(0.1083P)^2^+5.1516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.1957
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10614
_reflns_number_total             15052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03732g2.cif
_cod_data_source_block           MR530
_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_original_cell_volume        7270.1(2)
_cod_database_code               7062050
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.904
_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, All O(H,H) groups
2. Restrained distances
 F6-H7B
 2.05 with sigma of 0.02
 H71B-H7A
 2.05 with sigma of 0.02
 H7A-F22
 2.05 with sigma of 0.02
 H71B-H7B
 2.05 with sigma of 0.02
 P4-F19 \\sim P4A-F19A
 with sigma of 0.02
 F23-F22 \\sim F23A-F22A
 with sigma of 0.04
 P4-F21 \\sim P4A-F21A
 with sigma of 0.02
 P4-F20 \\sim P4A-F20A
 with sigma of 0.02
 P4-F24 \\sim P4A-F24A
 with sigma of 0.02
 P4-F23 \\sim P4A-F23A
 with sigma of 0.02
 P4-F22 \\sim P4A-F22A
 with sigma of 0.02
 F21-F20 \\sim F21A-F20A
 with sigma of 0.04
 F21-F23 \\sim F21A-F23A
 with sigma of 0.04
 F20-F23 \\sim F20A-F23A
 with sigma of 0.04
 F24-F22 \\sim F24A-F22A
 with sigma of 0.04
 F21-F24 \\sim F21A-F24A
 with sigma of 0.04
 F21-F22 \\sim F21A-F22A
 with sigma of 0.04
 F20-F24 \\sim F20A-F24A
 with sigma of 0.04
 F20-F22 \\sim F20A-F22A
 with sigma of 0.04
 F24-F23 \\sim F24A-F23A
 with sigma of 0.04
 F19-F21 \\sim F19A-F21A
 with sigma of 0.04
 F19-F20 \\sim F19A-F20A
 with sigma of 0.04
 F19-F24 \\sim F19A-F24A
 with sigma of 0.04
 F19-F23 \\sim F19A-F23A
 with sigma of 0.04
 F19-F22 \\sim F19A-F22A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(F19) = Uanis(F19A)
Uanis(F20) = Uanis(F20A)
Uanis(F21) = Uanis(F21A)
Uanis(F22) = Uanis(F22A)
Uanis(F23) = Uanis(F23A)
Uanis(F24) = Uanis(F24A)
Uanis(P4) = Uanis(P4A)
4. Others
 Sof(P4A)=Sof(F19A)=Sof(F20A)=Sof(F21A)=Sof(F22A)=Sof(F23A)=Sof(F24A)=1-FVAR(1)
 Sof(P4)=Sof(F19)=Sof(F20)=Sof(F21)=Sof(F22)=Sof(F23)=Sof(F24)=FVAR(1)
5.a Free rotating group:
 O7(H7A,H7B)
5.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C46(H46A,H46B), C47(H47A,
 H47B), C48(H48A,H48B), C49(H49A,H49B), C60(H60A,H60B), C61(H61A,H61B),
 C62(H62A,H62B), C63(H63A,H63B), C70(H70A,H70B), C11(H11A,H11B), C18(H18A,H18B),
  C29(H29A,H29B), C36(H36A,H36B)
5.c Aromatic/amide H refined with riding coordinates:
 C41(H41), C43(H43), C44(H44), C52(H52), C53(H53), C54(H54), C57(H57),
 C58(H58), C59(H59), C65(H65), C66(H66), C69(H69), C1(H1), C2(H2), C4(H4),
 C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27),
  C28(H28), C31(H31), C32(H32), C34(H34), C35(H35)
5.d Idealised Me refined as rotating group:
 C71(H71A,H71B,H71C)
;
_shelx_res_checksum              128
_olex2_date_sample_submission    2021-11-23
_olex2_exptl_crystal_mounting_method CryoLoop
_olex2_submission_original_sample_id MR530
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.593
_oxdiff_exptl_absorpt_empirical_full_min 0.497