#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:52:37 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301865 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/79/7227941.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7227941
loop_
_publ_author_name
'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.'
_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 κ-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 λ/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/[σ²(Fo²)+(0.0281P)²] where P=(Fo²+2Fc²)/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 > 2σ(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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
Br1 Br 0.88818(4) 0.16507(4) 0.28505(2) 0.05014(19) Uani 1 d
Cl Cl 1.16621(15) 0.40827(17) 0.48918(7) 0.1022(7) Uani 1 d
C17 C 0.8625(5) -0.5094(5) 0.3589(2) 0.0646(15) Uani 1 d
H17A H 0.863 -0.602 0.3524 0.097 Uiso 1 calc
H17B H 0.8069 -0.4865 0.3716 0.097 Uiso 1 calc
H17C H 0.917 -0.4856 0.3858 0.097 Uiso 1 calc
C20 C 0.7842(4) -0.1973(6) 0.07015(19) 0.0699(16) Uani 1 d
H20A H 0.7198 -0.1837 0.0523 0.105 Uiso 1 calc
H20B H 0.8129 -0.2579 0.0494 0.105 Uiso 1 calc
H20C H 0.8172 -0.1153 0.073 0.105 Uiso 1 calc
C19 C 0.8732(3) -0.2720(5) 0.15210(18) 0.0432(11) Uani 1 d
N7 N 0.8672(3) -0.5133(4) 0.26380(16) 0.0539(11) Uani 1 d
C4 C 0.8753(3) -0.0961(5) 0.24710(18) 0.0421(11) Uani 1 d
O4 O 0.7881(2) -0.2492(3) 0.12344(12) 0.0506(8) Uani 1 d
O3 O 0.9434(2) -0.2608(4) 0.13421(13) 0.0652(10) Uani 1 d
C5 C 0.8712(3) -0.3236(4) 0.20802(17) 0.0405(10) Uani 1 d
C10 C 0.8683(3) -0.2429(4) 0.25245(17) 0.0386(10) Uani 1 d
O1 O 0.8399(3) -0.2509(3) 0.39085(13) 0.0555(9) Uani 1 d
O2 O 0.8733(3) -0.0499(3) 0.20209(13) 0.0611(10) Uani 1 d
C9 C 0.8628(3) -0.3003(4) 0.30228(17) 0.0389(10) Uani 1 d
C3 C 0.8847(3) -0.0170(4) 0.29553(17) 0.0408(11) Uani 1 d
C8 C 0.8633(3) -0.4371(4) 0.3066(2) 0.0470(11) Uani 1 d
C11 C 0.9674(3) 0.0877(4) 0.41628(18) 0.0438(11) Uani 1 d
C12 C 0.9526(4) 0.1564(5) 0.4617(2) 0.0613(14) Uani 1 d
H12 H 0.9017 0.1351 0.4771 0.074 Uiso 1 calc
N2 N 0.9042(3) -0.0138(4) 0.39540(15) 0.0492(10) Uani 1 d
H2 H 0.8707 -0.0428 0.4173 0.059 Uiso 1 calc
C14 C 1.0898(4) 0.2815(5) 0.4623(2) 0.0568(14) Uani 1 d
C2 C 0.8887(3) -0.0721(4) 0.34582(17) 0.0394(10) Uani 1 d
C16 C 1.0471(4) 0.1129(5) 0.3960(2) 0.0491(12) Uani 1 d
H16 H 1.0592 0.0648 0.3667 0.059 Uiso 1 calc
C1 C 0.8613(3) -0.2139(4) 0.34883(17) 0.0382(10) Uani 1 d
C13 C 1.0125(5) 0.2553(6) 0.4841(2) 0.0703(16) Uani 1 d
H13 H 1.0011 0.3037 0.5134 0.084 Uiso 1 calc
C18 C 0.8744(4) -0.5532(5) 0.1711(2) 0.0638(15) Uani 1 d
H18A H 0.8734 -0.6412 0.1844 0.096 Uiso 1 calc
H18B H 0.9312 -0.5394 0.1582 0.096 Uiso 1 calc
H18C H 0.8212 -0.5395 0.1418 0.096 Uiso 1 calc
C15 C 1.1084(4) 0.2104(5) 0.4196(2) 0.0539(13) Uani 1 d
H15 H 1.1623 0.2276 0.4064 0.065 Uiso 1 calc
C6 C 0.8706(3) -0.4596(5) 0.21577(18) 0.0461(11) Uani 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.015
0 0 -1 0.015
1 -1 0 0.092
-1 0 0 0.036
1 0 0 0.099
0 1 0 0.077
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 C19 O4 123.6(4)
O3 C19 C5 124.4(4)
O4 C19 C5 111.8(4)
C6 N7 C8 120.2(4)
O2 C4 C3 123.0(4)
O2 C4 C10 118.5(4)
C3 C4 C10 118.5(4)
C19 O4 C20 115.1(4)
C10 C5 C6 118.2(4)
C10 C5 C19 123.3(4)
C6 C5 C19 118.5(4)
C5 C10 C9 119.0(4)
C5 C10 C4 120.1(4)
C9 C10 C4 120.9(4)
C10 C9 C8 119.1(4)
C10 C9 C1 118.2(4)
C8 C9 C1 122.6(4)
C2 C3 C4 121.6(4)
C2 C3 Br1 122.5(3)
C4 C3 Br1 115.9(3)
N7 C8 C9 121.2(4)
N7 C8 C17 115.1(4)
C9 C8 C17 123.6(4)
C16 C11 C12 119.6(5)
C16 C11 N2 122.0(4)
C12 C11 N2 118.1(4)
C13 C12 C11 120.6(5)
C2 N2 C11 129.2(4)
C15 C14 C13 121.5(5)
C15 C14 Cl 118.7(4)
C13 C14 Cl 119.8(4)
N2 C2 C3 129.2(4)
N2 C2 C1 111.7(4)
C3 C2 C1 118.6(4)
C15 C16 C11 119.3(4)
O1 C1 C9 123.5(4)
O1 C1 C2 117.3(4)
C9 C1 C2 119.2(4)
C12 C13 C14 118.8(5)
C14 C15 C16 120.0(5)
N7 C6 C5 122.3(4)
N7 C6 C18 115.7(4)
C5 C6 C18 122.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.879(4)
Cl C14 1.747(5)
C17 C8 1.508(7)
C20 O4 1.429(6)
C19 O3 1.205(5)
C19 O4 1.316(5)
C19 C5 1.506(6)
N7 C6 1.335(6)
N7 C8 1.336(6)
C4 O2 1.219(5)
C4 C3 1.442(6)
C4 C10 1.510(6)
C5 C10 1.395(6)
C5 C6 1.402(6)
C10 C9 1.400(6)
O1 C1 1.221(5)
C9 C8 1.400(6)
C9 C1 1.468(6)
C3 C2 1.372(6)
C11 C16 1.386(7)
C11 C12 1.395(6)
C11 N2 1.411(6)
C12 C13 1.374(8)
N2 C2 1.355(5)
C14 C15 1.368(7)
C14 C13 1.377(8)
C2 C1 1.508(6)
C16 C15 1.384(7)
C18 C6 1.483(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71579725
