Polymorphism and flexibility of six-porphyrin nanorings in the solid state.
Stawski, Wojciech; Anderson, Harry L.; Chemical science 15 (2024) 16938–16946; doi:10.1039/d4sc05255b

data_1572636
_publ_section_title
;
 Polymorphism and flexibility of six-porphyrin nanorings in the solid
 state.
;
_journal_issue                   41
_journal_name_full               'Chemical science'
_journal_page_first              16938
_journal_page_last               16946
_journal_paper_doi               10.1039/d4sc05255b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         '0.5(C312 H312 N24), 4(C6 H4 Cl2), C60'
_chemical_formula_sum            'C240 H172 Cl8 N12'
_chemical_formula_weight         3507.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-31 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.7920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.1388(3)
_cell_length_b                   53.4956(7)
_cell_length_c                   31.8306(4)
_cell_measurement_reflns_used    50149
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      42.2280
_cell_measurement_theta_min      3.9440
_cell_volume                     32830.1(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5035
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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     10.00  37.00   1.00   10.00    --   42.80 -37.00 -60.00   27
  2  \w     72.00 100.00   1.00   10.00    --   42.80 178.00 -60.00   28
  3  \w     40.00  67.00   1.00   10.00    --   42.80 -69.00  57.54   27
  4  \w    -23.00  15.00   1.00   10.00    --   42.80 -69.00  57.54   38
  5  \w     31.00  74.00   1.00   10.00    --   42.80 -99.00  30.00   43
  6  \w     30.00  71.00   1.00   10.00    --   42.80  37.00 -90.00   41
  7  \w     58.00 112.00   1.00   10.00    --   42.80  57.00 -90.00   54
  8  \w     59.00 117.00   1.00   10.00    --   42.80-178.00-120.00   58
  9  \w     -2.00  25.00   1.00   10.00    --   42.80 -77.00 -90.00   27
 10  \w     30.00  68.00   1.00   10.00    --   42.80 -57.00  30.00   38
 11  \w    -21.00   6.00   1.00   10.00    --   42.80 -19.00-120.00   27
 12  \w     21.00  46.00   1.00   10.00    --   42.80 -19.00-120.00   25
 13  \w     12.00  48.00   1.00   10.00    --   42.80 -19.00  60.00   36
 14  \w    -29.00  -1.00   1.00   10.00    --   42.80 -37.00 150.00   28
 15  \w     15.00  41.00   1.00   10.00    --   42.80 -37.00 150.00   26
 16  \w     13.00  65.00   1.00   10.00    --   42.80 -77.00 -60.00   52
 17  \w     25.00  64.00   1.00   10.00    --   42.80 -99.00-150.00   39
 18  \w     32.00  83.00   1.00   10.00    --   42.80 -99.00   0.00   51
 19  \w    -16.00  47.00   1.00   10.00    --   42.80 -77.00 120.00   63
 20  \w    -16.00   9.00   1.00   10.00    --   42.80 -77.00-120.00   25
 21  \w     49.00  74.00   1.00   10.00    --   42.80 -77.00-120.00   25
 22  \w     21.00  50.00   1.00   10.00    --   42.80  37.00-120.00   29
 23  \w     72.00 110.00   1.00   10.00    --   42.80  37.00-120.00   38
 24  \w     62.00 111.00   1.00   10.00    --   42.80  37.00  90.00   49
 25  \w    -22.00  47.00   1.00   10.00    --   42.80 -57.00   0.00   69
 26  \w     76.00 101.00   1.00   10.00    --   42.80 178.00 120.00   25
 27  \w   -112.00 -64.00   1.00   10.00    --  -43.42 178.00-180.00   48
 28  \w      9.00  34.00   1.00   10.00    --  -43.42  19.00 -30.00   25
 29  \w    -25.00   2.00   1.00   10.00    --   42.80 -57.00-120.00   27
 30  \w     64.00  91.00   1.00   10.00    --   42.80  37.00 150.00   27
 31  \w     52.00  79.00   1.00   10.00    --   42.80 -99.00 120.00   27
 32  \w     17.00  44.00   1.00   10.00    --   42.80 -52.00   2.45   27
 33  \w     56.00  82.00   1.00   10.00    --   42.80 -99.00-180.00   26
 34  \w     29.00  56.00   1.00   10.00    --   42.80 -53.00-111.94   27
 35  \w     69.00  96.00   1.00   10.00    --   42.80  19.00   0.00   27
 36  \w     14.00  56.00   1.00   10.00    --   42.80 -37.00  30.00   42
 37  \w     40.00  67.00   1.00   10.00    --   42.80 -53.00 150.79   27
 38  \w     28.00  58.00   1.00   10.00    --   42.80  57.00  60.00   30
 39  \w    -26.00   1.00   1.00   10.00    --   42.80 -57.00 120.00   27
 40  \w      9.00  62.00   1.00   10.00    --   42.80 -99.00-120.00   53
 41  \w     47.00  74.00   1.00   10.00    --   42.80 -99.00  60.00   27
 42  \w    -23.00   2.00   1.00   10.00    --   42.80 -19.00 -60.00   25
 43  \w     61.00 108.00   1.00   10.00    --   42.80-178.00  60.00   47
 44  \w     -6.00  21.00   1.00   10.00    --   42.80 -53.00 150.79   27
 45  \w     45.00  72.00   1.00   10.00    --   42.80  57.00  90.00   27
 46  \w     13.00  40.00   1.00   10.00    --   42.80 -99.00 120.00   27
 47  \w    -11.00  16.00   1.00   10.00    --   42.80 -57.00-150.00   27
 48  \w     18.00  46.00   1.00   10.00    --   42.80 -19.00 150.00   28
 49  \w     26.00  66.00   1.00   10.00    --   42.80 -57.00-150.00   40
 50  \w     72.00 112.00   1.00   10.00    --   42.80  37.00-180.00   40
 51  \w     82.00 116.00   1.00   10.00    --   42.80  19.00-180.00   34
 52  \w     96.00 121.00   1.00   10.00    --   42.80  19.00  30.00   25
 53  \w     71.00  98.00   1.00   10.00    --   42.80 178.00-180.00   27
 54  \w     83.00 108.00   1.00   10.00    --   42.80 178.00-150.00   25
 55  \w     82.00 111.00   1.00   10.00    --   42.80  57.00 -60.00   29
 56  \w     15.00  40.00   1.00   10.00    --   42.80 -19.00-180.00   25
 57  \w    -29.00  -2.00   1.00   10.00    --   42.80 -19.00 -90.00   27
 58  \w     13.00  39.00   1.00   10.00    --   42.80 -19.00   0.00   26
 59  \w      2.00  27.00   1.00   10.00    --   42.80 -37.00   0.00   25
 60  \w     39.00  73.00   1.00   10.00    --   42.80 -77.00 -30.00   34
 61  \w     -1.00  25.00   1.00   10.00    --   42.80 -77.00   0.00   26
 62  \w     35.00  82.00   1.00   10.00    --   42.80 -99.00 -90.00   47
 63  \w     66.00  93.00   1.00   10.00    --   42.80  37.00 -60.00   27
 64  \w    -33.00  -8.00   1.00   10.00    --  -43.42  57.00 -90.00   25
 65  \w    -97.00 -72.00   1.00   10.00    --  -43.42 -19.00 -90.00   25
 66  \w    -23.00   2.00   1.00   10.00    --  -43.42  77.00   0.00   25
 67  \w    -69.00 -42.00   1.00   10.00    --  -43.42 -48.00  91.64   27
 68  \w      0.00  25.00   1.00   10.00    --  -43.42  57.00-150.00   25
 69  \w    -39.00 -14.00   1.00   10.00    --  -43.42 -69.00 143.98   25
 70  \w   -100.00 -65.00   1.00   10.00    --  -43.42 -69.00 143.98   35
 71  \w     10.00  35.00   1.00   10.00    --   42.80  82.00-129.70   25
 72  \w     88.00 113.00   1.00   10.00    --   42.80  63.00-113.16   25
 73  \w     12.00  41.00   1.00   10.00    --   42.80  76.00  92.16   29
 74  \w     16.00  70.00   1.00   10.00    --   42.80  63.00-113.16   54
 75  \w     15.00  42.00   1.00   10.00    --   42.80  82.00   6.63   27
 76  \w     12.00  41.00   1.00   10.00    --   42.80  81.00 111.11   29
 77  \w     20.00  55.00   1.00   10.00    --   42.80  51.00 142.30   35
 78  \w     75.00 102.00   1.00   10.00    --   42.80  51.00 142.30   27
 79  \w     11.00  40.00   1.00   10.00    --   42.80  78.00 -67.91   29
 80  \w     67.00 102.00   1.00   10.00    --   42.80  37.00 120.00   35
 81  \w     13.00  39.00   1.00   10.00    --   42.80  80.00 -40.60   26
 82  \w     22.00  59.00   1.00   10.00    --   42.80  37.00   0.00   37
 83  \w     81.00 116.00   1.00   10.00    --   42.80  37.00   0.00   35
 84  \w     12.00  37.00   1.00   10.00    --   42.80  76.00 169.02   25
 85  \w     16.00  61.00   1.00   10.00    --   42.80  57.00  30.00   45
 86  \w     83.00 110.00   1.00   10.00    --   42.80  57.00  30.00   27
 87  \w     15.00  55.00   1.00   10.00    --   42.80  68.00-175.38   40
 88  \w     59.00  89.00   1.00   10.00    --   42.80  68.00-175.38   30
 89  \w     20.00  47.00   1.00   10.00    --   42.80  37.00 120.00   27
 90  \w    -43.00 -13.00   1.00   10.00    --  -43.42  57.00-150.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0405770000
_diffrn_orient_matrix_UB_12      -0.0001839000
_diffrn_orient_matrix_UB_13      0.0491064000
_diffrn_orient_matrix_UB_21      0.0207129000
_diffrn_orient_matrix_UB_22      -0.0274320000
_diffrn_orient_matrix_UB_23      -0.0039568000
_diffrn_orient_matrix_UB_31      0.0656313000
_diffrn_orient_matrix_UB_32      0.0087753000
_diffrn_orient_matrix_UB_33      -0.0113362000
_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  0.0573
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            234517
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        43.132
_diffrn_reflns_theta_max         43.132
_diffrn_reflns_theta_min         3.997
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.898
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    0.710
_exptl_crystal_description       block
_exptl_crystal_F_000             7328
_exptl_crystal_preparation       'As described in the main text.'
_exptl_crystal_recrystallization_method
;
Vapor diffusion of methanol into mixture 
of nanoring and fullerene C60 in ortho-dichlorobenzene.
;
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1171
_refine_ls_number_reflns         12095
_refine_ls_number_restraints     4278
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1626
_refine_ls_R_factor_gt           0.1395
_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^)+(0.3668P)^2^+51.9400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4051
_refine_ls_wR_factor_ref         0.4512
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8277
_reflns_number_total             12095
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05255b2.cif
_cod_data_source_block           P6-C60
_cod_depositor_comments
'Adding full bibliography for 1572633--1572636.cif.'
_cod_database_code               1572636
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.813
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              14345
_shelx_hkl_checksum              21341
_shelx_fab_checksum              9948
_ins_header
;
TITL 108wps22_WS in I2/m 
REM I2/m (#12 in standard setting)
CELL 1.54184  20.138776  53.495625  31.830614  90.0000 106.7922  90.0000
ZERR    4.00   0.000283   0.000667   0.000427   0.0000   0.0014   0.0000
LATT  2
SYMM -x, y,-z 
SFAC C H N Cl
UNIT 2400.00 1272.00 96.00 32.00
REM  CrysAlisPro recorded range (K): Min=100.0; max=100.0; aver:100.0
TEMP -173
TREF
HKLF 4
END
;
_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 1.163
_oxdiff_exptl_absorpt_empirical_full_min 0.881