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_7249721
_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 Cl2, C45 H36 N6 O3'
_chemical_formula_sum            'C46 H38 Cl2 N6 O3'
_chemical_formula_weight         793.72
_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     direct
_audit_creation_date             2024-09-04
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-11-11 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                76.807(6)
_cell_angle_beta                 75.289(6)
_cell_angle_gamma                84.733(7)
_cell_formula_units_Z            2
_cell_length_a                   12.106(6)
_cell_length_b                   13.118(6)
_cell_length_c                   13.961(7)
_cell_measurement_reflns_used    1584
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      18.66
_cell_measurement_theta_min      2.33
_cell_volume                     2086.5(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0684
_diffrn_reflns_av_unetI/netI     0.1096
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20197
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.543
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6128
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0700 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.8220.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.132
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         7357
_refine_ls_number_restraints     468
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.2213
_refine_ls_R_factor_gt           0.1270
_refine_ls_shift/su_max          0.068
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3448
_refine_ls_wR_factor_ref         0.4085
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3105
_reflns_number_total             7357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01150c2.cif
_cod_data_source_block           11_a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7249718--7249721.cif.'
_cod_original_cell_volume        2086.7(17)
_cod_database_code               7249721
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 C39, O1, C9, N2, N1, C8, C10, C15, C16, H8A, H8B, C5, C11, C14, H16A, H16B,
 C17, C4, C6, H11, C12, C13, H14, C18, C21, C3, H4, H6, C7, H12, H13, H18, C19,
 H21, C22, C2, H3, H7, H19, C20, H22, C1, C23, N3, H1A, H1B, N5, H23A, H23B,
 C44, C45, C24, C30, C43, N4, O3, C25, C29, N6, O2, C40, C42, H43, C38, C26,
 C28, H29, C31, H40, C41, H42, C35, H38A, H38B, H26, C27, H28, H31A, H31B, C32,
 H41, C34, C37, H27, C33, C36, H34, H37, H33, H36
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.006
3. Others
 Fixed Sof: Cl(0.5) Cl1(0.5) C46(0.5) H46A(0.5) H46B(0.5) Cl00(0.5) Cl01(0.5)
 C47(0.5) H47A(0.5) H47B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C47(H47A,H47B), C1(H1A,H1B), C8(H8A,H8B), C16(H16A,H16B),
 C23(H23A,H23B), C31(H31A,H31B), C38(H38A,H38B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C21(H21), C22(H22), C26(H26), C27(H27), C28(H28), C29(H29),
  C33(H33), C34(H34), C36(H36), C37(H37), C40(H40), C41(H41), C42(H42), C43(H43)
;
_shelx_res_checksum              3201
_olex2_submission_special_instructions 'No special instructions were received'