Benzoimidazole-2-one based macrocyclic arenes: synthesis, and solvent-induced structural changes
Zeng, Fei; Tang, Lin-Li; Wang, Jian-Hao; Sun, Bin; Ding, Man-Hua; Li, Qin-Chun; CrystEngComm 27 (2025) 474–477; doi:10.1039/D4CE01150C

data_7249720
_publ_section_title
;
 Benzoimidazole-2-one based macrocyclic arenes: synthesis, and
 solvent-induced structural changes
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              474
_journal_page_last               477
_journal_paper_doi               10.1039/D4CE01150C
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C H Cl3, 2(C15 H12 N2 O)'
_chemical_formula_sum            'C31 H25 Cl3 N4 O2'
_chemical_formula_weight         591.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-05-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-11-11 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.638(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.696(7)
_cell_length_b                   10.737(2)
_cell_length_c                   17.724(4)
_cell_measurement_reflns_used    2229
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      17.65
_cell_measurement_theta_min      2.31
_cell_volume                     5781(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31811
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         1.341
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0626 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.9061.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1518
_refine_ls_R_factor_gt           0.0592
_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^)+(0.0691P)^2^+0.8050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1697
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3021
_reflns_number_total             6561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01150c2.cif
_cod_data_source_block           11_a
_cod_depositor_comments
'Adding full bibliography for 7249718--7249721.cif.'
_cod_database_code               7249720
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C22(H22A,H22B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C27(H27), C28(H28), C29(H29), C30(H30)
;
_shelx_res_checksum              7271
_olex2_submission_special_instructions 'No special instructions were received'