Synthesis and antimicrobial evaluation of promising 7-arylamino-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylates and their halogenated amino compounds for treating Gram-negative bacterial infections
Novais, Juliana S.; Campos, Vinicius R.; Silva, Ana Carolina J. A.; de Souza, Maria C. B. V.; Ferreira, Vitor F.; Keller, Vitor G. L.; Ferreira, Matheus O.; Dias, Flaviana R. F.; Vitorino, Maíra I.; Sathler, Plínio C.; Santana, Marcos V.; Resende, Jackson A. L. C.; Castro, Helena C.; Cunha, Anna C.; RSC Adv. 7 (2017) 18311–; doi:10.1039/C7RA00825B

data_7227941
_publ_section_title
;
 Synthesis and antimicrobial evaluation of promising
 7-arylamino-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylates and their
 halogenated amino compounds for treating Gram-negative bacterial
 infections
;
_journal_issue                   30
_journal_name_full               'RSC Adv.'
_journal_page_first              18311
_journal_paper_doi               10.1039/C7RA00825B
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C19 H14 Br Cl N2 O4'
_chemical_formula_sum            'C19 H14 Br Cl N2 O4'
_chemical_formula_weight         449.68
_chemical_melting_point          414.0(10)
_chemical_name_common            Isoquinoline
_chemical_name_systematic
'4-Carbomethoxy-7-(4-chlorophenylamino)-6-bromo-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline '
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-10-05T09:24:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2017-01-18 deposited with the CCDC.
2017-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.18(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.560(3)
_cell_length_b                   10.207(2)
_cell_length_c                   25.110(5)
_cell_measurement_reflns_used    6694
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      3.520
_cell_measurement_theta_min      23.852
_cell_volume                     3647.7(13)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6491
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.129
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    2.429
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.3630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) 
was 0.1322 before and 0.0960 after correction. The Ratio of minimum 
to maximum transmission is 0.4871. The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            ' orange'
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       ' plate'
_exptl_crystal_F_000             1808
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0281P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                2144
_reflns_number_total             3565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra00825b2.cif
_cod_data_source_block           isonhclbr
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '413-415' was changed to '414.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        3647.6(13)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7227941