Uncovering the origins of supramolecular similarity in a series of benzimidazole structures
Orlando, Tainára; Lopes, Leandro C.; Neumann, Darlon A. M.; Andrade, Valquiria P.; Mittersteiner, Mateus; Rocha, Cláudia Q.; Zanatta, Nilo; Bonacorso, Helio G.; Martins, Marcos A. P.; Salbego, Paulo R. S.; CrystEngComm  (2022) –; doi:10.1039/D2CE00909A

data_7245472
_publ_section_title
;
 Uncovering the origins of supramolecular similarity in a series of
 benzimidazole structures
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00909A
_journal_year                    2022
_chemical_formula_moiety         'C18 H11 Br F3 N3 O2'
_chemical_formula_sum            'C18 H11 Br F3 N3 O2'
_chemical_formula_weight         438.206
_chemical_name_common            benzimidazole
_chemical_name_systematic
;
(4-bromophenyl)(4-hydroxy-4-(trifluoromethyl)-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-3-yl)methanone
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-03-18
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-03-19 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.897(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9853(2)
_cell_length_b                   15.8708(5)
_cell_length_c                   17.1004(6)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.57
_cell_volume                     1624.19(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'BRUKER APEX-III'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'PHOTON 100 CMOS detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            Bruker
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_device       'KAPPA four-circle goniometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29911
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9994
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_min         2.38
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.584
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0862 before and 0.0401 after correction.
The Ratio of minimum to maximum transmission is 0.9308.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             871.878
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.5115
_refine_diff_density_min         -0.4303
_refine_diff_density_rms         0.0889
_refine_ls_d_res_high            0.7792
_refine_ls_d_res_low             8.5492
_refine_ls_goodness_of_fit_ref   1.0342
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0342
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0208P)^2^+2.0365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0594
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              -6
_reflns_number_gt                3154
_reflns_number_total             3593
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2ce00909a2.cif
_cod_data_source_block           mo_mmv0393_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7245472
_exptl_absorpt_special_details   none
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C15(H15), C14(H14), C5(H5), C4(H4), C3(H3a), C17(H17), C18(H18),
 C2(H2), C8(H8)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'