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_7249719
_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 H2 Br2, C15 H12 N2 O'
_chemical_formula_sum            'C16 H14 Br2 N2 O'
_chemical_formula_weight         410.11
_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   mixed
_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                84.17(3)
_cell_angle_beta                 67.13(3)
_cell_angle_gamma                66.09(3)
_cell_formula_units_Z            2
_cell_length_a                   9.02(2)
_cell_length_b                   9.39(2)
_cell_length_c                   10.71(3)
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.52
_cell_measurement_theta_min      2.67
_cell_volume                     762(3)
_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 0.991
_diffrn_measured_fraction_theta_max 0.989
_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  0.0875
_diffrn_reflns_av_unetI/netI     0.1122
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7846
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         2.068
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.314
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0967 before and 0.0493 after correction.
The Ratio of minimum to maximum transmission is 0.6750.
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    1.786
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.879
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0326P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0999
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1506
_reflns_number_total             3137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01150c2.cif
_cod_data_source_block           11_a_a
_cod_depositor_comments
'Adding full bibliography for 7249718--7249721.cif.'
_cod_original_cell_volume        763(3)
_cod_database_code               7249719
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.619
_shelx_estimated_absorpt_t_min   0.619
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20)
;
_shelx_res_checksum              66843
_olex2_submission_special_instructions 'No special instructions were received'