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_7227940
_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 H13 Br2 Cl N2 O4'
_chemical_formula_sum            'C19 H13 Br2 Cl N2 O4'
_chemical_formula_weight         528.58
_chemical_melting_point          434.0(10)
_chemical_name_common            Isoquinoline
_chemical_name_systematic
4-Carbomethoxy-7-(4-chlorophenylamino)-6-bromo-3-bromoethyl-1-methyl-5,8-dioxo-5,8-dihydroisoquinoline
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-10-05T14:45:27-00:00
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.5261(10)
_cell_length_b                   9.0318(5)
_cell_length_c                   10.5375(6)
_cell_measurement_reflns_used    3754
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.46
_cell_measurement_theta_min      2.46
_cell_volume                     1953.52(18)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Photon 100 detector'
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Quazar multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5449
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26.016
_diffrn_reflns_theta_min         2.173
_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    4.315
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) 
was 0.0795 before and 0.0397 after correction. The Ratio of minimum 
to maximum transmission is 0.8335. The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            ' dark red'
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_description       ' plate'
_exptl_crystal_F_000             1040
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 777 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.009(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0246P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                2444
_reflns_number_total             3687
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra00825b2.cif
_cod_data_source_block           briso4clnh2cl_0ma_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '433-435' was changed to '434.0(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_database_code               7227940