#------------------------------------------------------------------------------
#$Date: 2023-11-06 09:03:27 +0100 (Mon 06 de Nov de 2023) $
#$Revision: 287393 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/27/7062722.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_7062722
loop_
_publ_author_name
'Aguilar, E. Contreras'
'Cogollo, E. Espitia'
'Echeverría, G. A.'
'Piro, O. E.'
'Jios, J. L.'
'Ulic, S. E.'
'Molina, R. D. I.'
'Arena, M. E.'
_publ_section_title
;
 Isosteric O/S exchange in carbonyl(thio)ureides: molecular interactions,
 structure, and bioactivity assays
;
_journal_issue                   39
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18341
_journal_page_last               18353
_journal_paper_doi               10.1039/D3NJ02529B
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C13 H18 N2 O3'
_chemical_formula_weight         250.29
_chemical_name_systematic        N-(butylcarbamoyl)-4-methoxybenzamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-09-16 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.637(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8639(2)
_cell_length_b                   15.2441(7)
_cell_length_c                   18.5621(8)
_cell_measurement_reflns_used    1755
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.9050
_cell_measurement_theta_min      4.1630
_cell_volume                     1367.08(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0604
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12946
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.025
_diffrn_reflns_theta_min         3.468
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0785
_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)+(0.1201P)²+0.4652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2118
_refine_ls_wR_factor_ref         0.2587
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1672
_reflns_number_total             3159
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj02529b2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7062721--7062722.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7062722
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.993
_oxdiff_exptl_absorpt_empirical_full_min 0.868
_oxdiff_exptl_absorpt_empirical_full_max 1.171
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8807(6) 0.3606(2) 0.73083(16) 0.0612(8) Uani 1 1 d . . . . .
C2 C 0.7581(8) 0.4112(3) 0.77975(18) 0.0824(11) Uani 1 1 d . . . . .
H2 H 0.8036 0.4021 0.8292 0.099 Uiso 1 1 calc R U . . .
C3 C 0.5698(7) 0.4749(3) 0.75622(17) 0.0771(10) Uani 1 1 d . . . . .
H3 H 0.4909 0.5091 0.7899 0.093 Uiso 1 1 calc R U . . .
C4 C 0.4957(6) 0.48892(19) 0.68281(14) 0.0543(7) Uani 1 1 d . . . . .
C5 C 0.6179(6) 0.4374(2) 0.63473(15) 0.0586(8) Uani 1 1 d . . . . .
H5 H 0.5692 0.4455 0.5852 0.070 Uiso 1 1 calc R U . . .
C6 C 0.8111(6) 0.3741(2) 0.65792(16) 0.0604(8) Uani 1 1 d . . . . .
H6 H 0.8935 0.3408 0.6243 0.073 Uiso 1 1 calc R U . . .
C7 C 1.1887(8) 0.2433(3) 0.7118(2) 0.0865(11) Uani 1 1 d . . . . .
H7A H 1.0470 0.2088 0.6849 0.130 Uiso 1 1 calc R U . . .
H7B H 1.3192 0.2053 0.7391 0.130 Uiso 1 1 calc R U . . .
H7C H 1.2822 0.2778 0.6788 0.130 Uiso 1 1 calc R U . . .
C8 C 0.2925(6) 0.5594(2) 0.66196(15) 0.0573(7) Uani 1 1 d . . . . .
C9 C -0.0538(6) 0.61153(19) 0.56238(15) 0.0551(7) Uani 1 1 d . . . . .
C10 C -0.3496(7) 0.7369(2) 0.57424(19) 0.0747(10) Uani 1 1 d D . . . .
H10A H -0.4252 0.7629 0.6154 0.090 Uiso 1 1 calc R U . . .
H10B H -0.4948 0.7025 0.5473 0.090 Uiso 1 1 calc R U . . .
C11 C -0.2631(13) 0.8081(4) 0.5267(4) 0.173(3) Uani 1 1 d D . . . .
H11A H -0.1452 0.8480 0.5571 0.207 Uiso 1 1 calc R U . . .
H11B H -0.1493 0.7817 0.4930 0.207 Uiso 1 1 calc R U . . .
C12 C -0.460(3) 0.8571(7) 0.4873(6) 0.299(7) Uani 1 1 d D . . . .
H12A H -0.5617 0.8907 0.5199 0.359 Uiso 1 1 calc R U . . .
H12B H -0.5902 0.8186 0.4591 0.359 Uiso 1 1 calc R U . . .
C13 C -0.333(4) 0.9189(6) 0.4369(5) 0.439(14) Uani 1 1 d D . . . .
H13A H -0.1446 0.9022 0.4339 0.658 Uiso 1 1 calc R U . . .
H13B H -0.3384 0.9777 0.4552 0.658 Uiso 1 1 calc R U . . .
H13C H -0.4357 0.9161 0.3896 0.658 Uiso 1 1 calc R U . . .
N1 N 0.1562(5) 0.55633(16) 0.59311(12) 0.0555(6) Uani 1 1 d . . . . .
H1 H 0.2063 0.5154 0.5656 0.067 Uiso 1 1 calc R U . . .
N2 N -0.1238(5) 0.67951(17) 0.60033(13) 0.0635(7) Uani 1 1 d . . . . .
H2A H -0.0320 0.6900 0.6419 0.076 Uiso 1 1 calc R U . . .
O1 O 1.0668(5) 0.29978(16) 0.75993(12) 0.0783(7) Uani 1 1 d . . . . .
O2 O 0.2498(5) 0.61778(16) 0.70440(12) 0.0794(8) Uani 1 1 d . . . . .
O3 O -0.1671(5) 0.59358(16) 0.50136(11) 0.0771(7) Uani 1 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 0.0000 0.0000 '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 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 116.0(3) . . ?
O1 C1 C6 124.7(3) . . ?
C2 C1 C6 119.3(3) . . ?
C1 C2 C3 120.7(3) . . ?
C2 C3 C4 120.7(3) . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 C8 124.8(2) . . ?
C3 C4 C8 117.3(3) . . ?
C6 C5 C4 121.8(3) . . ?
C5 C6 C1 119.6(3) . . ?
O2 C8 N1 121.8(3) . . ?
O2 C8 C4 121.2(2) . . ?
N1 C8 C4 117.1(2) . . ?
O3 C9 N2 123.3(3) . . ?
O3 C9 N1 118.1(3) . . ?
N2 C9 N1 118.5(2) . . ?
N2 C10 C11 112.6(3) . . ?
C12 C11 C10 119.3(7) . . ?
C11 C12 C13 111.2(13) . . ?
C8 N1 C9 127.8(2) . . ?
C9 N2 C10 122.0(3) . . ?
C1 O1 C7 118.0(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.363(4) . ?
C1 C2 1.378(5) . ?
C1 C6 1.372(4) . ?
C2 C3 1.371(5) . ?
C3 C4 1.385(4) . ?
C4 C5 1.374(4) . ?
C4 C8 1.481(4) . ?
C5 C6 1.381(4) . ?
C7 O1 1.419(4) . ?
C8 O2 1.222(3) . ?
C8 N1 1.371(3) . ?
C9 O3 1.232(3) . ?
C9 N2 1.320(4) . ?
C9 N1 1.393(4) . ?
C10 N2 1.443(4) . ?
C10 C11 1.490(7) . ?
C11 C12 1.361(10) . ?
C12 C13 1.509(12) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7B O2 0.96 2.60 3.544(4) 167.3 2_746
N1 H1 O3 0.86 2.07 2.885(3) 157.9 3_566
N2 H2A O1 0.86 2.49 3.162(3) 135.0 2_656
N2 H2A O2 0.86 2.02 2.666(3) 131.5 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.4(3) . . . . ?
C6 C1 C2 C3 -0.5(5) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C2 C3 C4 C8 -179.6(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C8 C4 C5 C6 178.4(3) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
O1 C1 C6 C5 179.6(3) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
C5 C4 C8 O2 -159.4(3) . . . . ?
C3 C4 C8 O2 19.8(4) . . . . ?
C5 C4 C8 N1 20.4(4) . . . . ?
C3 C4 C8 N1 -160.5(3) . . . . ?
N2 C10 C11 C12 167.8(8) . . . . ?
C10 C11 C12 C13 -173.9(8) . . . . ?
O2 C8 N1 C9 -4.3(5) . . . . ?
C4 C8 N1 C9 176.0(3) . . . . ?
O3 C9 N1 C8 -173.9(3) . . . . ?
N2 C9 N1 C8 5.2(4) . . . . ?
O3 C9 N2 C10 2.7(5) . . . . ?
N1 C9 N2 C10 -176.3(3) . . . . ?
C11 C10 N2 C9 -85.9(5) . . . . ?
C2 C1 O1 C7 177.1(3) . . . . ?
C6 C1 O1 C7 -3.1(5) . . . . ?
