Stereoelectronically-induced allosteric binding: shape complementarity promotes positive cooperativity in fullerene/buckybowl complexes
Larsen, Eric S.; Ahumada, Guillermo; Sultane, Prakash R.; Bielawski, Christopher W.; Chemical Communications  (2022) –; doi:10.1039/D2CC01908F

data_7130106
_publ_section_title
;
 Stereoelectronically-induced allosteric binding: shape complementarity
 promotes positive cooperativity in fullerene/buckybowl complexes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01908F
_journal_year                    2022
_chemical_formula_moiety         '2(C38 H23 N), C60, [+ solvent]'
_chemical_formula_sum            'C136 H46 N2'
_chemical_formula_weight         1707.75
_chemical_name_systematic        C136H46N2
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-10-14 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                94.2110(10)
_cell_angle_beta                 108.4190(10)
_cell_angle_gamma                111.7000(10)
_cell_formula_units_Z            1
_cell_length_a                   11.11500(10)
_cell_length_b                   12.5618(2)
_cell_length_c                   16.5098(2)
_cell_measurement_reflns_used    32765
_cell_measurement_temperature    123.0
_cell_measurement_theta_max      73.0080
_cell_measurement_theta_min      4.3240
_cell_volume                     1984.20(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.978
_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    -46.00  34.00   0.25   25.00    --    0.00 -77.00-150.00  320
  2  \w    -33.00  36.00   0.25   25.00    --    0.00 -82.00 120.00  276
  3  \w    -28.00  89.00   0.25   25.00    --    0.00  57.00  60.00  468
  4  \w    -33.00  36.00   0.25   25.00    --    0.00 -82.00  60.00  276
  5  \w    -89.00  27.00   0.25   25.00    --    0.00 -38.00 -30.00  464
  6  \w    -33.00  36.00   0.25   25.00    --    0.00 -82.00 -60.00  276
  7  \w      8.00 129.00   0.25   25.00    --   97.60 -30.00 -60.00  484
  8  \w     87.00 187.00   0.25   25.00    --   97.60  82.00 120.00  400
  9  \w     79.00 187.00   0.25   25.00    --   97.60  77.00   0.00  432
 10  \w     66.00 187.00   0.25   25.00    --   97.60  30.00  60.00  484
 11  \w      8.00 134.00   0.25   25.00    --   97.60 -82.00  30.00  504
 12  \w      8.00 134.00   0.25   25.00    --   97.60 -82.00 -60.00  504
 13  \w     87.00 187.00   0.25   25.00    --   97.60  82.00-180.00  400
 14  \w      8.00 134.00   0.25   25.00    --   97.60 -82.00 120.00  504
 15  \w     87.00 187.00   0.25   25.00    --   97.60  82.00-150.00  400
 16  \w      8.00 134.00   0.25   25.00    --   97.60 -82.00  60.00  504
 17  \w      8.00 134.00   0.25   25.00    --   97.60 -82.00 -90.00  504
 18  \w     66.00 187.00   0.25   25.00    --   97.60  30.00 150.00  484
 19  \w      8.00 127.00   0.25   25.00    --   97.60 -61.00-180.00  476
 20  \w      8.00 134.00   0.25   25.00    --   97.60 -82.00   0.00  504
 21  \w      8.00 134.00   0.25   25.00    --   97.60 -82.00-180.00  504
 22  \w      8.00 134.00   0.25   25.00    --   97.60 -82.00 150.00  504
 23  \w     79.00 187.00   0.25   25.00    --   97.60  77.00 -90.00  432
 24  \w    -89.00  27.00   0.25   25.00    --    0.00 -38.00-180.00  464
 25  \w    -33.00  36.00   0.25   25.00    --    0.00 -82.00 150.00  276
 26  \w    -33.00  36.00   0.25   25.00    --    0.00 -82.00-120.00  276
 27  \w    -27.00  89.00   0.25   25.00    --    0.00  38.00-150.00  464
 28  \w     42.00 187.00   0.25   25.00    --   97.60  15.00 -90.00  580
 29  \w     71.00 187.00   0.25   25.00    --   97.60  45.00  90.00  464
 30  \w     66.00 187.00   0.25   25.00    --   97.60  30.00   0.00  484
 31  \w     68.00 112.00   0.25   25.00    --   97.60  61.00 150.00  176
 32  \w     66.00 187.00   0.25   25.00    --   97.60  30.00 -60.00  484
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLab P200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0787287000
_diffrn_orient_matrix_UB_12      0.0369283000
_diffrn_orient_matrix_UB_13      0.0998255000
_diffrn_orient_matrix_UB_21      -0.1347160000
_diffrn_orient_matrix_UB_22      -0.0087677000
_diffrn_orient_matrix_UB_23      0.0124923000
_diffrn_orient_matrix_UB_31      -0.0379713000
_diffrn_orient_matrix_UB_32      -0.1297398000
_diffrn_orient_matrix_UB_33      0.0049194000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41799
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.585
_diffrn_reflns_theta_min         2.889
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.591
_exptl_absorpt_correction_T_min  0.227
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan'
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             876
_exptl_crystal_preparation
'The ompounds used for this analysis were prepared following known literature procedures.'
_exptl_crystal_recrystallization_method
'Slow evaporation of a concentrated chlorobenzene solution containing azacorannulane and buckminster fullerene in a two-to-one ratio, respectively.'
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         7843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0781
_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^)+(0.1635P)^2^+1.0251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2353
_refine_ls_wR_factor_ref         0.2371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7510
_reflns_number_total             7843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01908f2.cif
_cod_data_source_block           exp_54
_cod_original_cell_volume        1984.19(5)
_cod_database_code               7130106
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C142 H51 N2 Cl1 '
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.825
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8A(H00A), C10A(H00J), C33A(H00L), C15A(H00N), C31A(H00O), C27A(H00P),
 C19A(H00S), C32A(H00T), C21A(H00U), C25A(H00V), C13A(H00W), C26A(H00X),
 C20A(H00Z), C14A(H010)
2.b Idealised Me refined as rotating group:
 C37A(H01A,H01B,H01C), C39A(H01D,H01E,H01F), C38A(H01G,H01H,H01I)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 58 electrons were 
found in a volume of 275\%A^3^ in 3 voids per unit cell. 
This is consistent with the presence of 
1[C6H5Cl] per Asymmetric Unit 
which account for 58 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              53036
_shelx_hkl_checksum              92818
_shelx_fab_checksum              9349
_olex2_date_sample_completion    2020-04-28
_olex2_date_sample_data_collection 2020-04-27
_olex2_date_sample_submission    2020-04-23
_olex2_exptl_crystal_mounting_method
'A crystal was mounted on a loop and placed on the goniometer.'
_olex2_submission_original_sample_id exp_54
_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 3.979
_oxdiff_exptl_absorpt_empirical_full_min 0.118