Synthesis, crystal structure, Hirshfeld surface analysis, MEP study and molecular docking of <i>N</i>-{3-[(4-methoxyphenyl)carbamoyl]phenyl}-3-nitrobenzamide as a promising inhibitor of hfXa
Moreno-Fuquen, Rodolfo; Hurtado-Angulo, Mario; Arango-Daraviña, Kevin; Bain, Gavin; Kennedy, Alan R.; Acta Crystallographica Section E 76 (2020) 1762–1767; doi:10.1107/S2056989020013730

data_2243642
_publ_section_title
;
 Synthesis, crystal structure, Hirshfeld surface analysis, MEP study and
 molecular docking of
 <i>N</i>-{3-[(4-methoxyphenyl)carbamoyl]phenyl}-3-nitrobenzamide as a
 promising inhibitor of hfXa
;
_journal_coeditor_code           DJ2013
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1762
_journal_page_last               1767
_journal_paper_doi               10.1107/S2056989020013730
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C21 H17 N3 O5'
_chemical_formula_moiety         'C21 H17 N3 O5'
_chemical_formula_sum            'C21 H17 N3 O5'
_chemical_formula_weight         391.37
_chemical_melting_point          502.0(10)
_chemical_name_systematic
;
<i>N</i>-{3-[(4-Methoxyphenyl)carbamoyl]phenyl}-3-nitrobenzamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 97.644(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2948(3)
_cell_length_b                   7.1242(3)
_cell_length_c                   16.8297(7)
_cell_measurement_reflns_used    3172
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.075
_cell_measurement_theta_min      5.304
_cell_volume                     866.86(6)
_computing_cell_refinement
;
CrysalisPro (Agilent, 2014)
;
_computing_data_collection
;
CrysalisPro (Agilent, 2014)
;
_computing_data_reduction
;
CrysalisPro (Agilent, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2020)
;
_computing_publication_material
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_structure_refinement
;
<i>SHELXL2014/7</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al.</i>,  1994)
;
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3172
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         73.075
_diffrn_reflns_theta_min         5.304
_diffrn_source                   'sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60314
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       'fragment cut from large slab'
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.303
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 524 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      7.346
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0660P)^2^+0.3205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                2982
_reflns_number_total             3172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dj2013sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2243642
_cod_database_fobs_code          2243642
_shelx_hkl_checksum              34556
_shelx_res_checksum              60745
_shelxl_version_number           2.014