#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/81/2018108.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_2018108
loop_
_publ_author_name
'Kranjc, Krištof'
'Kočevar, Marijan'
'Perdih, Franc'
_publ_section_title
;
 Methyl 2-benzamido-4-(3,4-dimethoxyphenyl)-5-methylbenzoate and
 N-{5-benzoyl-2-[(Z)-2-methoxyethenyl]-4-methylphenyl}benzamide
;
_journal_coeditor_code           KU3044
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o201
_journal_page_last               o205
_journal_paper_doi               10.1107/S0108270111015794
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C24 H23 N O5'
_chemical_formula_moiety         'C24 H23 N O5'
_chemical_formula_sum            'C24 H23 N O5'
_chemical_formula_weight         405.43
_chemical_name_systematic
;
Methyl 2-benzamido-4-(3,4-dimethoxyphenyl)-5-methylbenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.8175(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.65160(10)
_cell_length_b                   14.7810(3)
_cell_length_c                   17.8063(4)
_cell_measurement_reflns_used    4631
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.55
_cell_volume                     2003.49(7)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.055
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8696
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         3.59
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9814
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0590P)²+0.4255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1262
_reflns_number_gt                3167
_reflns_number_total             4566
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ku3044.cif
_cod_data_source_block           Ia
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018108
_cod_database_fobs_code          2018108
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.30792(17) 0.52864(9) 0.43674(7) 0.0380(3) Uani d . 1 . .
H H2 0.3184 0.4712 0.4607 0.057 Uiso d R 1 . .
O O1 0.25463(18) 0.40077(8) 0.53818(7) 0.0532(3) Uani d . 1 . .
O O2 0.12684(17) 0.44292(8) 0.63932(7) 0.0492(3) Uani d . 1 . .
O O3 0.3406(2) 0.61562(8) 0.33357(7) 0.0633(4) Uani d . 1 . .
O O4 0.10238(16) 1.00534(8) 0.35584(6) 0.0494(3) Uani d . 1 . .
O O5 0.25616(17) 1.11462(7) 0.45477(7) 0.0504(3) Uani d . 1 . .
C C1 0.1320(2) 0.61975(11) 0.60655(8) 0.0363(4) Uani d . 1 . .
H H1 0.0905 0.5975 0.6503 0.044 Uiso calc R 1 . .
C C2 0.18995(19) 0.55772(10) 0.55571(8) 0.0327(3) Uani d . 1 . .
C C3 0.24941(19) 0.59109(10) 0.48853(8) 0.0332(3) Uani d . 1 . .
C C4 0.2505(2) 0.68393(11) 0.47678(8) 0.0361(3) Uani d . 1 . .
H H4 0.2895 0.7062 0.4326 0.043 Uiso calc R 1 . .
C C5 0.19470(19) 0.74489(10) 0.52928(8) 0.0338(3) Uani d . 1 . .
C C6 0.1324(2) 0.71223(11) 0.59595(8) 0.0359(3) Uani d . 1 . .
C C7 0.1946(2) 0.45995(11) 0.57472(9) 0.0363(4) Uani d . 1 . .
C C8 0.1372(3) 0.35083(13) 0.66588(12) 0.0649(6) Uani d . 1 . .
H H8A 0.0687 0.3126 0.6306 0.097 Uiso calc R 1 . .
H H8B 0.0923 0.3473 0.7142 0.097 Uiso calc R 1 . .
H H8C 0.2574 0.3313 0.6705 0.097 Uiso calc R 1 . .
C C9 0.3473(2) 0.54225(11) 0.36497(9) 0.0382(4) Uani d . 1 . .
C C10 0.4012(2) 0.45859(11) 0.32554(9) 0.0367(4) Uani d . 1 . .
C C11 0.3653(2) 0.37167(12) 0.34866(10) 0.0483(4) Uani d . 1 . .
H H11 0.3055 0.3632 0.391 0.058 Uiso calc R 1 . .
C C12 0.4176(3) 0.29714(14) 0.30929(11) 0.0596(5) Uani d . 1 . .
H H12 0.3924 0.2391 0.3252 0.071 Uiso calc R 1 . .
C C13 0.5069(2) 0.30905(15) 0.24645(11) 0.0587(5) Uani d . 1 . .
H H13 0.5429 0.2591 0.2202 0.07 Uiso calc R 1 . .
C C14 0.5425(2) 0.39501(15) 0.22288(10) 0.0551(5) Uani d . 1 . .
H H14 0.6027 0.403 0.1805 0.066 Uiso calc R 1 . .
C C15 0.4898(2) 0.46981(13) 0.26151(9) 0.0455(4) Uani d . 1 . .
H H15 0.5135 0.5277 0.2447 0.055 Uiso calc R 1 . .
C C16 0.2070(2) 0.84353(10) 0.51266(8) 0.0343(3) Uani d . 1 . .
C C17 0.1448(2) 0.87694(10) 0.44148(8) 0.0343(3) Uani d . 1 . .
H H17 0.0917 0.8375 0.4054 0.041 Uiso calc R 1 . .
C C18 0.1608(2) 0.96744(10) 0.42373(8) 0.0355(4) Uani d . 1 . .
C C19 0.24404(19) 1.02684(10) 0.47741(9) 0.0368(4) Uani d . 1 . .
C C20 0.3070(2) 0.99382(11) 0.54698(9) 0.0408(4) Uani d . 1 . .
H H20 0.3632 1.0328 0.5827 0.049 Uiso calc R 1 . .
C C21 0.2880(2) 0.90318(11) 0.56481(9) 0.0407(4) Uani d . 1 . .
H H21 0.3304 0.8824 0.6125 0.049 Uiso calc R 1 . .
C C22 -0.0106(3) 0.95324(14) 0.30494(10) 0.0559(5) Uani d . 1 . .
H H22A 0.0525 0.9021 0.2882 0.084 Uiso calc R 1 . .
H H22B -0.0521 0.9897 0.2622 0.084 Uiso calc R 1 . .
H H22C -0.1087 0.9325 0.3298 0.084 Uiso calc R 1 . .
C C23 0.3186(3) 1.17891(12) 0.51055(12) 0.0615(5) Uani d . 1 . .
H H23A 0.4393 1.1663 0.5274 0.092 Uiso calc R 1 . .
H H23B 0.2496 1.1752 0.5526 0.092 Uiso calc R 1 . .
H H23C 0.3092 1.2386 0.4894 0.092 Uiso calc R 1 . .
C C24 0.0653(2) 0.77239(12) 0.65522(9) 0.0469(4) Uani d . 1 . .
H H24A -0.016 0.7392 0.6823 0.07 Uiso calc R 1 . .
H H24B 0.007 0.8239 0.6313 0.07 Uiso calc R 1 . .
H H24C 0.1621 0.7924 0.6897 0.07 Uiso calc R 1 . .
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'
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
C9 N1 C3 . . 129.39(13) ?
C9 N1 H2 . . 122.6 ?
C3 N1 H2 . . 108 ?
C7 O2 C8 . . 116.65(14) ?
C18 O4 C22 . . 117.86(13) ?
C19 O5 C23 . . 117.21(14) ?
C6 C1 C2 . . 123.93(14) ?
C6 C1 H1 . . 118 ?
C2 C1 H1 . . 118 ?
C1 C2 C3 . . 118.18(14) ?
C1 C2 C7 . . 119.68(13) ?
C3 C2 C7 . . 122.09(13) ?
C4 C3 N1 . . 122.80(13) ?
C4 C3 C2 . . 118.72(13) ?
N1 C3 C2 . . 118.48(13) ?
C3 C4 C5 . . 122.03(14) ?
C3 C4 H4 . . 119 ?
C5 C4 H4 . . 119 ?
C4 C5 C6 . . 119.71(14) ?
C4 C5 C16 . . 117.91(13) ?
C6 C5 C16 . . 122.37(13) ?
C1 C6 C5 . . 117.41(13) ?
C1 C6 C24 . . 118.83(14) ?
C5 C6 C24 . . 123.75(14) ?
O1 C7 O2 . . 122.03(14) ?
O1 C7 C2 . . 125.74(14) ?
O2 C7 C2 . . 112.22(13) ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O3 C9 N1 . . 124.08(15) ?
O3 C9 C10 . . 121.31(14) ?
N1 C9 C10 . . 114.60(13) ?
C11 C10 C15 . . 118.75(15) ?
C11 C10 C9 . . 123.59(14) ?
C15 C10 C9 . . 117.65(15) ?
C10 C11 C12 . . 120.72(17) ?
C10 C11 H11 . . 119.6 ?
C12 C11 H11 . . 119.6 ?
C13 C12 C11 . . 120.03(19) ?
C13 C12 H12 . . 120 ?
C11 C12 H12 . . 120 ?
C14 C13 C12 . . 119.69(17) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
C13 C14 C15 . . 120.68(17) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C14 C15 C10 . . 120.13(17) ?
C14 C15 H15 . . 119.9 ?
C10 C15 H15 . . 119.9 ?
C21 C16 C17 . . 118.19(14) ?
C21 C16 C5 . . 121.56(14) ?
C17 C16 C5 . . 120.15(14) ?
C18 C17 C16 . . 121.27(14) ?
C18 C17 H17 . . 119.4 ?
C16 C17 H17 . . 119.4 ?
O4 C18 C17 . . 124.80(14) ?
O4 C18 C19 . . 115.57(14) ?
C17 C18 C19 . . 119.62(14) ?
O5 C19 C20 . . 125.20(15) ?
O5 C19 C18 . . 115.70(14) ?
C20 C19 C18 . . 119.09(14) ?
C19 C20 C21 . . 120.96(15) ?
C19 C20 H20 . . 119.5 ?
C21 C20 H20 . . 119.5 ?
C16 C21 C20 . . 120.84(15) ?
C16 C21 H21 . . 119.6 ?
C20 C21 H21 . . 119.6 ?
O4 C22 H22A . . 109.5 ?
O4 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O4 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
O5 C23 H23A . . 109.5 ?
O5 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
O5 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C6 C24 H24A . . 109.5 ?
C6 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C6 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 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
N1 C9 . 1.3575(19) ?
N1 C3 . 1.4095(19) ?
N1 H2 . 0.95 ?
O1 C7 . 1.2082(19) ?
O2 C7 . 1.3329(18) ?
O2 C8 . 1.441(2) ?
O3 C9 . 1.2189(19) ?
O4 C18 . 1.3658(18) ?
O4 C22 . 1.415(2) ?
O5 C19 . 1.3647(18) ?
O5 C23 . 1.422(2) ?
C1 C6 . 1.380(2) ?
C1 C2 . 1.392(2) ?
C1 H1 . 0.93 ?
C2 C3 . 1.411(2) ?
C2 C7 . 1.484(2) ?
C3 C4 . 1.388(2) ?
C4 C5 . 1.396(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.409(2) ?
C5 C16 . 1.493(2) ?
C6 C24 . 1.509(2) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 C10 . 1.500(2) ?
C10 C11 . 1.385(2) ?
C10 C15 . 1.394(2) ?
C11 C12 . 1.386(2) ?
C11 H11 . 0.93 ?
C12 C13 . 1.381(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.374(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.384(3) ?
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C16 C21 . 1.381(2) ?
C16 C17 . 1.398(2) ?
C17 C18 . 1.383(2) ?
C17 H17 . 0.93 ?
C18 C19 . 1.403(2) ?
C19 C20 . 1.373(2) ?
C20 C21 . 1.388(2) ?
C20 H20 . 0.93 ?
C21 H21 . 0.93 ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?
C23 H23A . 0.96 ?
C23 H23B . 0.96 ?
C23 H23C . 0.96 ?
C24 H24A . 0.96 ?
C24 H24B . 0.96 ?
C24 H24C . 0.96 ?
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
N1 H2 O1 . 0.95 1.83 2.6741(17) 146
C13 H13 O3 2_645 0.93 2.53 3.450(2) 172
C24 H24B O5 3_576 0.96 2.57 3.420(2) 147.7
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 . . . . -1.4(2) ?
C6 C1 C2 C7 . . . . 176.10(15) ?
C9 N1 C3 C4 . . . . -11.2(3) ?
C9 N1 C3 C2 . . . . 169.84(15) ?
C1 C2 C3 C4 . . . . 1.1(2) ?
C7 C2 C3 C4 . . . . -176.27(14) ?
C1 C2 C3 N1 . . . . -179.86(14) ?
C7 C2 C3 N1 . . . . 2.7(2) ?
N1 C3 C4 C5 . . . . -178.93(14) ?
C2 C3 C4 C5 . . . . 0.0(2) ?
C3 C4 C5 C6 . . . . -1.0(2) ?
C3 C4 C5 C16 . . . . 177.82(14) ?
C2 C1 C6 C5 . . . . 0.4(2) ?
C2 C1 C6 C24 . . . . 179.74(15) ?
C4 C5 C6 C1 . . . . 0.8(2) ?
C16 C5 C6 C1 . . . . -177.97(14) ?
C4 C5 C6 C24 . . . . -178.49(15) ?
C16 C5 C6 C24 . . . . 2.7(2) ?
C8 O2 C7 O1 . . . . 3.3(2) ?
C8 O2 C7 C2 . . . . -175.43(15) ?
C1 C2 C7 O1 . . . . -173.91(16) ?
C3 C2 C7 O1 . . . . 3.5(3) ?
C1 C2 C7 O2 . . . . 4.8(2) ?
C3 C2 C7 O2 . . . . -177.84(13) ?
C3 N1 C9 O3 . . . . 1.6(3) ?
C3 N1 C9 C10 . . . . -178.31(14) ?
O3 C9 C10 C11 . . . . -161.18(18) ?
N1 C9 C10 C11 . . . . 18.7(2) ?
O3 C9 C10 C15 . . . . 17.8(2) ?
N1 C9 C10 C15 . . . . -162.28(14) ?
C15 C10 C11 C12 . . . . 0.5(3) ?
C9 C10 C11 C12 . . . . 179.48(17) ?
C10 C11 C12 C13 . . . . 0.2(3) ?
C11 C12 C13 C14 . . . . -0.5(3) ?
C12 C13 C14 C15 . . . . 0.0(3) ?
C13 C14 C15 C10 . . . . 0.7(3) ?
C11 C10 C15 C14 . . . . -0.9(2) ?
C9 C10 C15 C14 . . . . -179.98(15) ?
C4 C5 C16 C21 . . . . -128.69(16) ?
C6 C5 C16 C21 . . . . 50.1(2) ?
C4 C5 C16 C17 . . . . 47.6(2) ?
C6 C5 C16 C17 . . . . -133.54(16) ?
C21 C16 C17 C18 . . . . -1.1(2) ?
C5 C16 C17 C18 . . . . -177.51(13) ?
C22 O4 C18 C17 . . . . 12.4(2) ?
C22 O4 C18 C19 . . . . -168.40(14) ?
C16 C17 C18 O4 . . . . -179.51(14) ?
C16 C17 C18 C19 . . . . 1.3(2) ?
C23 O5 C19 C20 . . . . -8.4(2) ?
C23 O5 C19 C18 . . . . 171.96(15) ?
O4 C18 C19 O5 . . . . -0.1(2) ?
C17 C18 C19 O5 . . . . 179.12(13) ?
O4 C18 C19 C20 . . . . -179.76(14) ?
C17 C18 C19 C20 . . . . -0.5(2) ?
O5 C19 C20 C21 . . . . 179.88(14) ?
C18 C19 C20 C21 . . . . -0.5(2) ?
C17 C16 C21 C20 . . . . 0.0(2) ?
C5 C16 C21 C20 . . . . 176.40(14) ?
C19 C20 C21 C16 . . . . 0.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654309
2 PubChem 123276689
