Mechanically interlocked porphyrinoids: self-assembly of metal-stabilised catenaphyrins.
Sarwa, Aleksandra; Matviyishyn, Maksym; Perdek, Jędrzej P; Trzaskowski, Bartosz; Kulesza, Dagmara; Zych, Eugeniusz; Szyszko, Bartosz; Chemical communications (Cambridge, England) 62 (2026) 148–151; doi:10.1039/d5cc05702g

data_7135153
_publ_section_title
;
 Mechanically interlocked porphyrinoids: self-assembly of metal-stabilised
 catenaphyrins.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              148
_journal_page_last               151
_journal_paper_doi               10.1039/d5cc05702g
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C42 H36 F10 N4 O8 Zn, C H4 O'
_chemical_formula_sum            'C43 H40 F10 N4 O9 Zn'
_chemical_formula_weight         1012.16
_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   mixed
_atom_sites_solution_primary     difmap
_audit_creation_date             2025-08-27
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-08-28 deposited with the CCDC.	2025-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.05(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.981(3)
_cell_length_b                   14.833(4)
_cell_length_c                   13.238(3)
_cell_measurement_reflns_used    36277
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4940
_cell_measurement_theta_min      3.3110
_cell_volume                     2156.2(10)
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 41.104a 64-bit (release 16-03-2021))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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     49.00 118.00   0.50    0.05    --   83.00  13.00 167.36  138
  2  \w     49.00  86.00   0.50    0.05    --   83.00  13.00  -4.31   74
  3  \w     89.00 114.00   0.50    0.05    --   83.00  13.00  -4.31   50
  4  \w     90.00 120.00   0.50    0.05    --   83.00   3.00 -79.91   60
  5  \w     46.00  86.00   0.50    0.05    --   83.00   3.00 -79.91   80
  6  \w     42.00  67.00   0.50    0.05    --   83.00  -3.00  76.86   50
  7  \w     10.00  35.00   0.50    0.05    --   59.37 -30.00-180.00   50
  8  \w     44.00  77.00   0.50    0.05    --   83.00 -73.00 -52.68   66
  9  \w     44.00  76.00   0.50    0.05    --   83.00 -73.00  85.69   64
 10  \w     18.00  50.00   0.50    0.05    --   59.37-126.00 150.00   64
 11  \w     45.00  95.00   0.50    0.05    --   79.25-126.00  60.00  100
 12  \w     47.00  81.00   0.50    0.05    --   83.00 -91.00 -61.75   68
 13  \w   -103.00 -75.00   0.50    0.05    --  -74.77-126.00-120.00   56
 14  \w   -124.00 -76.00   0.50    0.05    --  -74.77 -30.00 -30.00   96
 15  \w   -124.00 -93.00   0.50    0.05    --  -75.16 -30.00  60.00   62
 16  \w   -103.00 -58.00   0.50    0.05    --  -75.16 126.00  30.00   90
 17  \w     35.00  60.00   0.50    0.05    --   26.00  50.00  16.87   50
 18  \w     62.00  93.00   0.50    0.05    --   59.59  30.00-150.00   62
 19  \w     64.00 101.00   0.50    0.05    --   59.59  30.00  30.00   74
 20  \w     27.00  67.00   0.50    0.05    --   59.59 -95.00 150.00   80
 21  \w     10.00  35.00   0.50    0.05    --   59.59 -30.00 -90.00   50
 22  \w     11.00  37.00   0.50    0.05    --   59.59 -30.00  90.00   52
 23  \w     10.00  35.00   0.50    0.05    --   59.59 -30.00-120.00   50
 24  \w     11.00  37.00   0.50    0.05    --   59.59 -30.00 150.00   52
 25  \w     66.00 109.00   0.50    0.05    --   59.59  30.00 -60.00   86
 26  \w     10.00  35.00   0.50    0.05    --   59.59 -30.00 120.00   50
 27  \w     61.00  86.00   0.50    0.05    --   59.59  30.00   0.00   50
 28  \w   -111.00 -85.00   0.50    0.05    --  -61.58 -30.00   0.00   52
 29  \w   -107.00 -82.00   0.50    0.05    --  -70.00 -58.00 -54.06   50
 30  \w   -106.00 -80.00   0.50    0.05    --  -70.00 -51.00 -42.70   52
 31  \w     40.00  75.00   0.50    0.05    --   74.19 -95.00 -60.00   70
 32  \w   -124.00 -99.00   0.50    0.05    --  -74.77 -30.00  90.00   50
 33  \w   -121.00 -96.00   0.50    0.05    --  -75.45-125.00  60.00   50
 34  \w   -121.00 -85.00   0.50    0.05    --  -75.45-125.00 -90.00   72
 35  \w     80.00 121.00   0.50    0.05    --   79.25  30.00-150.00   82
 36  \w     92.00 124.00   0.50    0.05    --   79.25 125.00  90.00   64
 37  \w     59.00  85.00   0.50    0.05    --   79.25 -95.00 -30.00   52
 38  \w     45.00  81.00   0.50    0.05    --   79.25 -95.00-180.00   72
 39  \w     41.00  67.00   0.50    0.05    --   79.25-125.00 150.00   52
 40  \w     80.00 105.00   0.50    0.05    --   79.25  30.00 -30.00   50
 41  \w     81.00 107.00   0.50    0.05    --   79.25-125.00 150.00   52
 42  \w     96.00 125.00   0.50    0.05    --   79.25 125.00-150.00   58
 43  \w     79.00 104.00   0.50    0.05    --   79.25 125.00-180.00   50
 44  \w     79.00 104.00   0.50    0.05    --   79.25 125.00 150.00   50
 45  \w     39.00  68.00   0.50    0.05    --   79.25 -95.00  60.00   58
 46  \w     80.00 105.00   0.50    0.05    --   79.25  30.00 -90.00   50
 47  \w     83.00 114.00   0.50    0.05    --   79.25  30.00   0.00   62
 48  \w     84.00 122.00   0.50    0.05    --   79.25 125.00 -60.00   76
 49  \w     36.00  62.00   0.50    0.05    --   79.25-125.00 -30.00   52
 50  \w     40.00  65.00   0.50    0.05    --   79.25 -95.00-120.00   50
 51  \w     40.00  83.00   0.50    0.05    --   79.25-125.00-120.00   86
 52  \w     83.00 109.00   0.50    0.05    --   79.25-125.00  60.00   52
 53  \w     60.00  92.00   0.50    0.05    --   79.25-125.00 -60.00   64
 54  \w     40.00  90.00   0.50    0.05    --   79.25 -95.00 150.00  100
 55  \w     41.00  67.00   0.50    0.05    --   79.25-125.00  90.00   52
 56  \w     45.00  92.00   0.50    0.05    --   79.25-125.00-180.00   94
 57  \w     81.00 109.00   0.50    0.05    --   79.25-125.00   0.00   56
 58  \w     40.00  66.00   0.50    0.05    --   79.25-125.00-150.00   52
 59  \w     63.00  89.00   0.50    0.05    --   79.25  15.00 -60.00   52
 60  \w     79.00 121.00   0.50    0.05    --   79.25 125.00  30.00   84
 61  \w     36.00  64.00   0.50    0.05    --   79.25-125.00  30.00   56
 62  \w   -110.00 -85.00   0.50    0.05    --  -79.25 -69.00   3.50   50
 63  \w   -111.00 -85.00   0.50    0.05    --  -79.25 -70.00 -25.88   52
 64  \w   -118.00 -93.00   0.50    0.05    --  -79.25 -56.00  -5.04   50
 65  \w   -109.00 -84.00   0.50    0.05    --  -79.25 -70.00 -30.58   50
 66  \w   -107.00 -82.00   0.50    0.05    --  -79.25 -82.00 -58.39   50
 67  \w    -80.00 -55.00   0.50    0.05    --  -79.25  87.00 162.94   50
 68  \w   -116.00 -91.00   0.50    0.05    --  -79.25 -79.00 -36.83   50
 69  \w   -105.00 -80.00   0.50    0.05    --  -79.25 -81.00 -45.99   50
 70  \w    -68.00 -42.00   0.50    0.05    --  -79.25  62.00-171.35   52
 71  \w   -111.00 -85.00   0.50    0.05    --  -79.25-155.00  34.05   52
 72  \w     80.00 118.00   0.50    0.05    --   83.00  -1.00-176.60   76
 73  \w     66.00 131.00   0.50    0.05    --   83.00  21.00  76.23  130
 74  \w     62.00 109.00   0.50    0.05    --   83.00   1.00  10.02   94
 75  \w     67.00  92.00   0.50    0.05    --   83.00  10.00 134.86   50
 76  \w     82.00 112.00   0.50    0.05    --   83.00-127.00 -37.95   60
 77  \w     84.00 122.00   0.50    0.05    --   83.00   9.00-140.27   76
 78  \w     47.00 113.00   0.50    0.05    --   83.00   4.00  72.55  132
 79  \w     41.00  77.00   0.50    0.05    --   83.00-127.00 -37.95   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0462935000
_diffrn_orient_matrix_UB_12      -0.0619770000
_diffrn_orient_matrix_UB_13      -0.0851794000
_diffrn_orient_matrix_UB_21      0.0966151000
_diffrn_orient_matrix_UB_22      0.0392462000
_diffrn_orient_matrix_UB_23      -0.0719355000
_diffrn_orient_matrix_UB_31      0.0906164000
_diffrn_orient_matrix_UB_32      -0.0734930000
_diffrn_orient_matrix_UB_33      0.0333696000
_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  0.0231
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            46577
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.683
_diffrn_reflns_theta_min         3.339
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       needle
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.336(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     638
_refine_ls_number_reflns         8791
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0221
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+0.4353P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0583
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                8671
_reflns_number_total             8791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05702g4.cif
_cod_data_source_block           dipyrrin_acetal
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'diffmap' was changed
to 'difmap'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7135153--7135154.cif.
;
_cod_database_code               7135153
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C10 H10 N4 O4 Zn1'
_cell_oxdiff_angle_alpha         90.0168(7)
_cell_oxdiff_angle_beta          90.0597(7)
_cell_oxdiff_angle_gamma         90.0049(7)
_cell_oxdiff_length_a            10.97915(10)
_cell_oxdiff_length_b            14.83600(13)
_cell_oxdiff_length_c            13.23760(11)
_cell_oxdiff_measurement_reflns_used 36277
_cell_oxdiff_volume              2156.23(3)
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.594
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.664(14)
 0.336(14)
2. 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
3. Restrained distances
 C1A-O1D \\sim C1A-O1C \\sim C1A-O2D \\sim C1A-O2C
 with sigma of 0.02
 C1A-C1D \\sim C1A-C1C \\sim C1A-C2D \\sim C1A-C2C
 with sigma of 0.02
 O1C-C1C \\sim O1D-C1D \\sim O2D-C2D \\sim O2C-C2C
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C2C) = Uanis(C2D)
5. Rigid body (RIGU) restrains
 C2D, O2D, C1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: O2C(0.92) O1C(0.92) C2C(0.92) H2CA(0.92) H2CB(0.92) H2CC(0.92)
 H1A(0.92) H1AA(0.08) C1C(0.92) H1CA(0.92) H1CB(0.92) H1CC(0.92) O1D(0.08)
 C1D(0.08) H1DA(0.08) H1DB(0.08) H1DC(0.08) O2D(0.08) C2D(0.08) H2DA(0.08)
 H2DB(0.08) H2DC(0.08)
7.a Ternary CH refined with riding coordinates:
 C1(H1), C17(H17), C17A(H17A), C1A(H1A), C1A(H1AA)
7.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C14(H14), C3A(H3A), C15(H15), C4A(H4A), C18(H18), C14A(H14A),
 C15A(H15A)
7.c Idealised Me refined with riding coordinates:
 C1D(H1DA,H1DB,H1DC), C2D(H2DA,H2DB,H2DC)
7.d Idealised Me refined as rotating group:
 C4B(H4BA,H4BB,H4BC), C1S(H1SA,H1SB,H1SC), C3C(H3CA,H3CB,H3CC), C4C(H4CA,H4CB,
 H4CC), C2C(H2CA,H2CB,H2CC), C3B(H3BA,H3BB,H3BC), C2B(H2BA,H2BB,H2BC), C1B(H1BA,
 H1BB,H1BC), C1C(H1CA,H1CB,H1CC)
;
_shelx_res_checksum              84612
_shelx_hkl_checksum              35392
_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 1.559
_oxdiff_exptl_absorpt_empirical_full_min 0.702