New β-carboline containing imidazolium derivatives as potential VEGFR2 inhibitors: synthesis, X-ray structure, anti-proliferative evaluations, and molecular modeling
Ma, Ling; Chen, Xiaofei; Zhu, Siyu; Chen, Wei; Ma, Qin; Fan, Wenxi; Zhang, Jie; Guo, Liang; RSC Medicinal Chemistry  (2022) –; doi:10.1039/D2MD00065B

data_7245076
_publ_section_title
;
 New \b-carboline containing imidazolium derivatives as potential VEGFR2
 inhibitors: synthesis, X-ray structure, anti-proliferative evaluations,
 and molecular modeling
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D2MD00065B
_journal_year                    2022
_chemical_formula_moiety         'Cl, C23 H22 N3, C2 H6 O'
_chemical_formula_sum            'C25 H28 Cl N3 O'
_chemical_formula_weight         421.95
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc21z9x8
_audit_creation_date             2018-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-28 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.347(4)
_cell_length_b                   16.232(3)
_cell_length_c                   7.4296(14)
_cell_measurement_reflns_used    1572
_cell_measurement_temperature    220
_cell_measurement_theta_max      19.97
_cell_measurement_theta_min      2.22
_cell_volume                     2212.6(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      220
_diffrn_measured_fraction_theta_full 0.999
_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  0.0644
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14105
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.463
_diffrn_reflns_theta_min         1.675
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0777 before and 0.0669 after correction. The Ratio of minimum to maximum transmission is 0.8916. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1050 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4382
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0697P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1398
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                3200
_reflns_number_total             4382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2md00065b2.cif
_cod_data_source_block           mo_20181013-cxf_0ma
_cod_database_code               7245076
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C9(H9), C19(H19), C23(H23), C12(H12), C13(H13), C20(H20),
 C7(H7), C22(H22), C6(H6), C8(H8), C21(H21)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C24(H24A,H24B,H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'