Co-crystals built from macrocycles with pyromellitic diimides and naphthalene derivatives: transformation of a binary co-crystal solvate to a solvate through solvent exchange
Tominaga, Masahide; Kamada, Ryusei; Hyodo, Tadashi; Yamaguchi, Kentaro; CrystEngComm 27 (2025) 5003–5009; doi:10.1039/D5CE00462D

data_7250666
_publ_section_title
;
 Co-crystals built from macrocycles with pyromellitic diimides and
 naphthalene derivatives: transformation of a binary co-crystal solvate to
 a solvate through solvent exchange
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              5003
_journal_page_last               5009
_journal_paper_doi               10.1039/D5CE00462D
_journal_volume                  27
_journal_year                    2025
_chemical_formula_sum            'C59 H51 Br2 Cl15 N4 O10'
_chemical_formula_weight         1667.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-10-08 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.877(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6670(8)
_cell_length_b                   22.9197(19)
_cell_length_c                   15.4712(13)
_cell_measurement_reflns_used    9742
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.44
_cell_measurement_theta_min      3.61
_cell_volume                     3386.8(5)
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (H\"ubschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            44054
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.900
_diffrn_reflns_theta_min         3.475
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    7.457
_exptl_absorpt_correction_T_max  0.8526
_exptl_absorpt_correction_T_min  0.5363
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            yellowish-brown
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_description       plate
_exptl_crystal_F_000             1676
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.274
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.00072(9)
_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   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         7202
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0598P)^2^+12.2921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1494
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6548
_reflns_number_total             7202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00462d2.cif
_cod_data_source_block           1c
_cod_depositor_comments
'Adding full bibliography for 7250664--7250669.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7250666
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.523
_shelx_estimated_absorpt_t_max   0.707
_shelx_res_checksum              97756