Synthesis of new piperazinyl-pyrrolo[1,2-a]quinoxaline derivatives as inhibitors of Candida albicans multidrug transporters by a Buchwald‒Hartwig cross-coupling reaction
Guillon, Jean; Nim, Shweta; Moreau, Stéphane; Ronga, Luisa; Savrimoutou, Solène; Thivet, Elisabeth; Marchivie, Mathieu; Di Pietro, Attilio; Prasad, Rajendra; Le Borgne, Marc; RSC Advances 10 (2020) 2915–2931; doi:10.1039/C9RA09348F

data_7239760
_publ_section_title
;
 Synthesis of new piperazinyl-pyrrolo[1,2-a]quinoxaline derivatives as
 inhibitors of Candida albicans multidrug transporters by a
 Buchwald--Hartwig cross-coupling reaction
;
_journal_issue                   5
_journal_name_full               'RSC Advances'
_journal_page_first              2915
_journal_page_last               2931
_journal_paper_doi               10.1039/C9RA09348F
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C58 H54 F2 N8 O0.2'
_chemical_formula_weight         904.29
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccyy00w
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-04 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                77.83(2)
_cell_angle_beta                 81.76(4)
_cell_angle_gamma                87.25(3)
_cell_formula_units_Z            2
_cell_length_a                   9.471(10)
_cell_length_b                   13.021(6)
_cell_length_c                   19.887(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      25
_cell_volume                     2372(3)
_computing_cell_refinement       'CAD-4 software'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'Nonius (unpublished)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Enraf Nonius cad-4 diffractometer'
_diffrn_measurement_method       \W-2\Scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8875
_diffrn_reflns_theta_full        69.94
_diffrn_reflns_theta_max         69.94
_diffrn_reflns_theta_min         6.37
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  0.9090
_exptl_absorpt_correction_T_min  0.8813
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             955
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       0.0080(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         8875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1460
_refine_ls_R_factor_gt           0.0944
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+5.9355P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2133
_refine_ls_wR_factor_ref         0.2411
_reflns_number_gt                5174
_reflns_number_total             8875
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ra09348f2.cif
_cod_data_source_block           jg546
_cod_depositor_comments
'Adding full bibliography for 7239760--7239761.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C58 H54 F2 N8 O0.20'
_cod_database_code               7239760