#------------------------------------------------------------------------------
#$Date: 2020-10-24 07:10:30 +0300 (Sat, 24 Oct 2020) $
#$Revision: 258590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243642.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243642
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Hurtado-Angulo, Mario'
'Arango-Daraviña, Kevin'
'Bain, Gavin'
'Kennedy, Alan R.'
_publ_section_title
;
 Synthesis, crystal structure, Hirshfeld surface analysis, MEP study and
 molecular docking of
 N-{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
;
N-{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 et al.,  2020)
;
_computing_publication_material
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare et al.,  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 x determined using 524 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  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/[σ²(Fo²)+(0.0660P)²+0.3205P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            dj2013sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2243642
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.6697(5) 0.7564(5) 0.02367(18) 0.0376(8) Uani d 1 . .
O O2 0.5804(5) 0.9765(5) 0.09701(19) 0.0350(7) Uani d 1 . .
O O3 0.2455(4) 0.5231(5) 0.35551(16) 0.0282(6) Uani d 1 . .
O O4 0.2775(4) 0.5306(4) 0.64175(16) 0.0263(6) Uani d 1 . .
O O5 -0.1675(4) 0.3265(4) 0.93736(17) 0.0277(7) Uani d 1 . .
N N1 0.6116(4) 0.8119(5) 0.0852(2) 0.0246(7) Uani d 1 . .
N N2 0.3987(4) 0.8014(5) 0.37262(18) 0.0197(7) Uani d 1 . .
H H2N 0.4792 0.8744 0.3531 0.024 Uiso calc 1 . .
N N3 0.0451(4) 0.7137(5) 0.67641(19) 0.0198(7) Uani d 1 . .
H H3N -0.0181 0.8174 0.6646 0.024 Uiso calc 1 . .
C C1 0.4599(5) 0.5945(6) 0.2656(2) 0.0200(8) Uani d 1 . .
C C2 0.5006(5) 0.7309(6) 0.2117(2) 0.0201(7) Uani d 1 . .
H H2 0.4757 0.8598 0.2199 0.024 Uiso calc 1 . .
C C3 0.5793(5) 0.6713(6) 0.1453(2) 0.0214(8) Uani d 1 . .
C C4 0.6237(5) 0.4862(7) 0.1322(2) 0.0249(8) Uani d 1 . .
H H4 0.6775 0.4510 0.0860 0.030 Uiso calc 1 . .
C C5 0.5880(5) 0.3544(6) 0.1879(2) 0.0263(9) Uani d 1 . .
H H5 0.6220 0.2271 0.1817 0.032 Uiso calc 1 . .
C C6 0.5021(5) 0.4077(6) 0.2532(2) 0.0223(8) Uani d 1 . .
H H6 0.4718 0.3150 0.2899 0.027 Uiso calc 1 . .
C C7 0.3569(5) 0.6363(6) 0.3358(2) 0.0212(8) Uani d 1 . .
C C8 0.3212(5) 0.8658(6) 0.4411(2) 0.0187(8) Uani d 1 . .
C C9 0.2817(5) 0.7434(6) 0.5012(2) 0.0186(7) Uani d 1 . .
H H9 0.3051 0.6129 0.4968 0.022 Uiso calc 1 . .
C C10 0.2080(5) 0.8120(6) 0.5675(2) 0.0190(8) Uani d 1 . .
C C11 0.1753(5) 1.0041(6) 0.5751(2) 0.0207(8) Uani d 1 . .
H H11 0.1239 1.0508 0.6202 0.025 Uiso calc 1 . .
C C12 0.2191(5) 1.1265(6) 0.5156(2) 0.0229(8) Uani d 1 . .
H H12 0.1986 1.2574 0.5207 0.028 Uiso calc 1 . .
C C13 0.2922(5) 1.0588(6) 0.4492(2) 0.0213(8) Uani d 1 . .
H H13 0.3225 1.1433 0.4093 0.026 Uiso calc 1 . .
C C14 0.1800(5) 0.6713(6) 0.6309(2) 0.0199(8) Uani d 1 . .
C C15 -0.0029(5) 0.6049(6) 0.7415(2) 0.0185(8) Uani d 1 . .
C C16 0.0253(5) 0.4121(6) 0.7483(2) 0.0217(8) Uani d 1 . .
H H16 0.0805 0.3463 0.7085 0.026 Uiso calc 1 . .
C C17 -0.0274(5) 0.3165(6) 0.8134(2) 0.0217(8) Uani d 1 . .
H H17 -0.0067 0.1850 0.8181 0.026 Uiso calc 1 . .
C C18 -0.1096(5) 0.4096(6) 0.8715(2) 0.0218(8) Uani d 1 . .
C C19 -0.1431(6) 0.6016(6) 0.8636(2) 0.0249(9) Uani d 1 . .
H H19 -0.2038 0.6659 0.9021 0.030 Uiso calc 1 . .
C C20 -0.0880(5) 0.6982(6) 0.7997(2) 0.0236(9) Uani d 1 . .
H H20 -0.1082 0.8297 0.7954 0.028 Uiso calc 1 . .
C C21 -0.1360(6) 0.1300(7) 0.9478(3) 0.0312(10) Uani d 1 . .
H H21A -0.1834 0.0882 0.9967 0.047 Uiso calc 1 . .
H H21B -0.2001 0.0623 0.9015 0.047 Uiso calc 1 . .
H H21C -0.0031 0.1045 0.9524 0.047 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C18 O5 C21 . . 117.5(3) ?
O2 N1 O1 . . 122.6(4) ?
O2 N1 C3 . . 119.7(3) ?
O1 N1 C3 . . 117.7(4) ?
C7 N2 C8 . . 124.3(3) ?
C7 N2 H2N . . 117.8 ?
C8 N2 H2N . . 117.8 ?
C14 N3 C15 . . 125.8(3) ?
C14 N3 H3N . . 117.1 ?
C15 N3 H3N . . 117.1 ?
C2 C1 C6 . . 120.1(4) ?
C2 C1 C7 . . 123.0(4) ?
C6 C1 C7 . . 116.7(4) ?
C1 C2 C3 . . 117.3(4) ?
C1 C2 H2 . . 121.3 ?
C3 C2 H2 . . 121.3 ?
C4 C3 C2 . . 123.4(4) ?
C4 C3 N1 . . 118.6(4) ?
C2 C3 N1 . . 117.9(4) ?
C5 C4 C3 . . 118.2(4) ?
C5 C4 H4 . . 120.9 ?
C3 C4 H4 . . 120.9 ?
C4 C5 C6 . . 120.0(4) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C5 C6 C1 . . 120.9(4) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
O3 C7 N2 . . 124.7(4) ?
O3 C7 C1 . . 120.0(4) ?
N2 C7 C1 . . 115.2(3) ?
C9 C8 C13 . . 119.7(3) ?
C9 C8 N2 . . 121.8(4) ?
C13 C8 N2 . . 118.4(4) ?
C10 C9 C8 . . 120.1(4) ?
C10 C9 H9 . . 119.9 ?
C8 C9 H9 . . 119.9 ?
C9 C10 C11 . . 120.5(4) ?
C9 C10 C14 . . 116.1(4) ?
C11 C10 C14 . . 123.2(4) ?
C12 C11 C10 . . 119.2(4) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C13 C12 C11 . . 120.6(4) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C8 . . 119.9(4) ?
C12 C13 H13 . . 120.0 ?
C8 C13 H13 . . 120.0 ?
O4 C14 N3 . . 123.0(4) ?
O4 C14 C10 . . 121.4(3) ?
N3 C14 C10 . . 115.5(4) ?
C16 C15 C20 . . 119.2(4) ?
C16 C15 N3 . . 123.4(4) ?
C20 C15 N3 . . 117.4(3) ?
C17 C16 C15 . . 119.7(4) ?
C17 C16 H16 . . 120.2 ?
C15 C16 H16 . . 120.2 ?
C18 C17 C16 . . 121.0(4) ?
C18 C17 H17 . . 119.5 ?
C16 C17 H17 . . 119.5 ?
O5 C18 C17 . . 124.9(4) ?
O5 C18 C19 . . 115.6(4) ?
C17 C18 C19 . . 119.4(4) ?
C20 C19 C18 . . 119.9(4) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C19 C20 C15 . . 120.8(4) ?
C19 C20 H20 . . 119.6 ?
C15 C20 H20 . . 119.6 ?
O5 C21 H21A . . 109.5 ?
O5 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O5 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 . 1.235(5) ?
O2 N1 . 1.216(5) ?
O3 C7 . 1.221(5) ?
O4 C14 . 1.229(5) ?
O5 C18 . 1.372(5) ?
O5 C21 . 1.425(5) ?
N1 C3 . 1.465(5) ?
N2 C7 . 1.346(5) ?
N2 C8 . 1.425(5) ?
N2 H2N . 0.8800 ?
N3 C14 . 1.359(5) ?
N3 C15 . 1.424(5) ?
N3 H3N . 0.8800 ?
C1 C2 . 1.388(6) ?
C1 C6 . 1.389(6) ?
C1 C7 . 1.511(5) ?
C2 C3 . 1.389(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.383(6) ?
C4 C5 . 1.376(6) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.389(6) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C8 C9 . 1.394(5) ?
C8 C13 . 1.401(6) ?
C9 C10 . 1.390(5) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.398(6) ?
C10 C14 . 1.498(5) ?
C11 C12 . 1.396(6) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.388(5) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C15 C16 . 1.391(5) ?
C15 C20 . 1.396(5) ?
C16 C17 . 1.388(6) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.383(6) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.392(6) ?
C19 C20 . 1.380(6) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2N O4 2_656 0.88 2.09 2.908(4) 155.0
N3 H3N O3 2_556 0.88 2.21 3.056(4) 162.5
C5 H5 O2 1_545 0.95 2.28 3.093(5) 143.3
C19 H19 O1 1_456 0.95 2.44 3.365(5) 164.1
C21 H21C O1 2_646 0.98 2.64 3.490(5) 144.8
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.6(5) ?
C7 C1 C2 C3 . . . . -173.7(3) ?
C1 C2 C3 C4 . . . . -2.2(5) ?
C1 C2 C3 N1 . . . . 175.9(3) ?
O2 N1 C3 C4 . . . . -177.1(4) ?
O1 N1 C3 C4 . . . . 3.1(5) ?
O2 N1 C3 C2 . . . . 4.7(5) ?
O1 N1 C3 C2 . . . . -175.2(3) ?
C2 C3 C4 C5 . . . . 0.0(6) ?
N1 C3 C4 C5 . . . . -178.1(3) ?
C3 C4 C5 C6 . . . . 2.8(6) ?
C4 C5 C6 C1 . . . . -3.3(6) ?
C2 C1 C6 C5 . . . . 1.1(6) ?
C7 C1 C6 C5 . . . . 176.7(3) ?
C8 N2 C7 O3 . . . . 1.3(6) ?
C8 N2 C7 C1 . . . . -178.4(3) ?
C2 C1 C7 O3 . . . . 142.4(4) ?
C6 C1 C7 O3 . . . . -33.1(5) ?
C2 C1 C7 N2 . . . . -37.9(5) ?
C6 C1 C7 N2 . . . . 146.6(3) ?
C7 N2 C8 C9 . . . . 36.2(5) ?
C7 N2 C8 C13 . . . . -146.6(4) ?
C13 C8 C9 C10 . . . . 2.1(5) ?
N2 C8 C9 C10 . . . . 179.3(3) ?
C8 C9 C10 C11 . . . . -0.9(5) ?
C8 C9 C10 C14 . . . . -176.8(3) ?
C9 C10 C11 C12 . . . . -0.6(5) ?
C14 C10 C11 C12 . . . . 175.0(3) ?
C10 C11 C12 C13 . . . . 0.7(6) ?
C11 C12 C13 C8 . . . . 0.5(6) ?
C9 C8 C13 C12 . . . . -2.0(6) ?
N2 C8 C13 C12 . . . . -179.2(3) ?
C15 N3 C14 O4 . . . . -0.2(6) ?
C15 N3 C14 C10 . . . . -178.0(3) ?
C9 C10 C14 O4 . . . . 28.3(5) ?
C11 C10 C14 O4 . . . . -147.5(4) ?
C9 C10 C14 N3 . . . . -153.8(3) ?
C11 C10 C14 N3 . . . . 30.4(5) ?
C14 N3 C15 C16 . . . . -26.6(6) ?
C14 N3 C15 C20 . . . . 155.5(4) ?
C20 C15 C16 C17 . . . . -1.4(6) ?
N3 C15 C16 C17 . . . . -179.3(3) ?
C15 C16 C17 C18 . . . . 0.7(6) ?
C21 O5 C18 C17 . . . . 1.8(6) ?
C21 O5 C18 C19 . . . . 180.0(4) ?
C16 C17 C18 O5 . . . . 179.4(3) ?
C16 C17 C18 C19 . . . . 1.3(6) ?
O5 C18 C19 C20 . . . . 179.3(3) ?
C17 C18 C19 C20 . . . . -2.4(6) ?
C18 C19 C20 C15 . . . . 1.7(6) ?
C16 C15 C20 C19 . . . . 0.3(6) ?
N3 C15 C20 C19 . . . . 178.3(4) ?

_cod_database_fobs_code 2243642
