#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/75/2237565.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_2237565
loop_
_publ_author_name
'Maganhi, Stella H.'
'Damião, Mariana C. F. C. B.'
'Tavares, Maurício T.'
'Parise Filho, Roberto'
_publ_section_title
;
 N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide: an analogue of
 capsaicin
;
_journal_coeditor_code           TK5191
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o332
_journal_paper_doi               10.1107/S1600536813002201
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H15 N O3'
_chemical_formula_moiety         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29
_chemical_name_systematic
;
N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.139(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9810(2)
_cell_length_b                   26.6520(10)
_cell_length_c                   10.0545(3)
_cell_measurement_reflns_used    5124
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1333.84(8)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and SCALEPACK'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)\\bbr00'
_computing_publication_material
'Marvinsketch (Chemaxon, 2010) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4550
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0859P)²+0.0674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1489
_reflns_number_gt                1698
_reflns_number_total             2602
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5191.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2237565
_cod_database_fobs_code          2237565
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_symmetry_multiplicity
O O1 -0.0219(3) 0.06137(6) 0.88685(15) 0.0754(5) Uani d . 1 1
O O2 -0.0295(3) 0.00662(6) 0.71012(17) 0.0797(5) Uani d . 1 1
O O3 0.4080(3) 0.24272(5) 0.87268(12) 0.0634(4) Uani d . 1 1
N N1 0.4208(3) 0.22490(6) 0.65426(14) 0.0496(4) Uani d . 1 1
H H1N1 0.3768 0.2357 0.5702 0.060 Uiso d R 1 1
C C1 0.1365(4) 0.08000(7) 0.78849(19) 0.0525(5) Uani d . 1 1
C C2 0.1354(4) 0.04694(8) 0.6838(2) 0.0585(5) Uani d . 1 1
C C3 0.2867(5) 0.05485(8) 0.5769(2) 0.0733(6) Uani d . 1 1
H H3 0.2878 0.0322 0.5065 0.088 Uiso calc R 1 1
C C4 0.4407(4) 0.09851(8) 0.5771(2) 0.0649(6) Uani d . 1 1
H H4 0.5483 0.1047 0.5053 0.078 Uiso calc R 1 1
C C5 0.4398(3) 0.13305(7) 0.68029(18) 0.0503(5) Uani d . 1 1
C C6 0.2825(3) 0.12319(7) 0.79020(18) 0.0505(5) Uani d . 1 1
H H6 0.2782 0.1453 0.8616 0.061 Uiso calc R 1 1
C C7 -0.1575(5) 0.01955(9) 0.8290(2) 0.0740(7) Uani d . 1 1
H H7A -0.3444 0.0279 0.8094 0.089 Uiso calc R 1 1
H H7B -0.1510 -0.0086 0.8903 0.089 Uiso calc R 1 1
C C8 0.5961(4) 0.18139(7) 0.6730(2) 0.0556(5) Uani d . 1 1
H H8A 0.7042 0.1856 0.7545 0.067 Uiso calc R 1 1
H H8B 0.7169 0.1795 0.5997 0.067 Uiso calc R 1 1
C C9 0.3359(3) 0.25214(7) 0.75640(17) 0.0467(5) Uani d . 1 1
C C10 0.1449(3) 0.29384(7) 0.72454(16) 0.0440(4) Uani d . 1 1
C C11 -0.0105(4) 0.29652(7) 0.60682(19) 0.0547(5) Uani d . 1 1
H H11 0.0065 0.2719 0.5422 0.066 Uiso calc R 1 1
C C12 -0.1888(4) 0.33522(8) 0.5853(2) 0.0620(6) Uani d . 1 1
H H12 -0.2918 0.3360 0.5062 0.074 Uiso calc R 1 1
C C13 -0.2198(4) 0.37300(7) 0.6775(2) 0.0535(5) Uani d . 1 1
C C14 -0.0639(4) 0.37058(8) 0.7936(2) 0.0598(5) Uani d . 1 1
H H14 -0.0779 0.3958 0.8570 0.072 Uiso calc R 1 1
C C15 0.1126(4) 0.33142(8) 0.81753(18) 0.0576(5) Uani d . 1 1
H H15 0.2117 0.3303 0.8977 0.069 Uiso calc R 1 1
C C16 -0.4161(4) 0.41514(8) 0.6534(2) 0.0710(6) Uani d . 1 1
H H16A -0.3634 0.4345 0.5782 0.106 Uiso calc R 1 1
H H16B -0.4180 0.4363 0.7307 0.106 Uiso calc R 1 1
H H16C -0.5924 0.4016 0.6358 0.106 Uiso calc R 1 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 0.0000 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
C1 O1 C7 105.39(16)
C2 O2 C7 105.13(16)
C9 N1 C8 122.43(15)
C9 N1 H1N1 117.9
C8 N1 H1N1 119.5
C6 C1 C2 122.7(2)
C6 C1 O1 127.92(18)
C2 C1 O1 109.40(18)
C3 C2 C1 121.5(2)
C3 C2 O2 128.7(2)
C1 C2 O2 109.73(19)
C2 C3 C4 116.89(19)
C2 C3 H3 121.6
C4 C3 H3 121.6
C5 C4 C3 122.5(2)
C5 C4 H4 118.7
C3 C4 H4 118.7
C4 C5 C6 118.83(19)
C4 C5 C8 120.96(17)
C6 C5 C8 120.17(17)
C1 C6 C5 117.52(17)
C1 C6 H6 121.2
C5 C6 H6 121.2
O1 C7 O2 108.35(18)
O1 C7 H7A 110.0
O2 C7 H7A 110.0
O1 C7 H7B 110.0
O2 C7 H7B 110.0
H7A C7 H7B 108.4
N1 C8 C5 112.19(14)
N1 C8 H8A 109.2
C5 C8 H8A 109.2
N1 C8 H8B 109.2
C5 C8 H8B 109.2
H8A C8 H8B 107.9
O3 C9 N1 121.77(17)
O3 C9 C10 121.03(16)
N1 C9 C10 117.19(15)
C15 C10 C11 117.55(17)
C15 C10 C9 118.96(16)
C11 C10 C9 123.47(17)
C12 C11 C10 120.57(18)
C12 C11 H11 119.7
C10 C11 H11 119.7
C11 C12 C13 121.98(18)
C11 C12 H12 119.0
C13 C12 H12 119.0
C14 C13 C12 117.42(18)
C14 C13 C16 120.94(19)
C12 C13 C16 121.64(18)
C13 C14 C15 121.17(18)
C13 C14 H14 119.4
C15 C14 H14 119.4
C14 C15 C10 121.30(17)
C14 C15 H15 119.4
C10 C15 H15 119.4
C13 C16 H16A 109.5
C13 C16 H16B 109.5
H16A C16 H16B 109.5
C13 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.380(2)
O1 C7 1.417(3)
O2 C2 1.384(2)
O2 C7 1.418(3)
O3 C9 1.2358(19)
N1 C9 1.339(2)
N1 C8 1.459(2)
N1 H1N1 0.9124
C1 C6 1.361(3)
C1 C2 1.372(3)
C2 C3 1.352(3)
C3 C4 1.394(3)
C3 H3 0.9300
C4 C5 1.387(3)
C4 H4 0.9300
C5 C6 1.403(3)
C5 C8 1.508(3)
C6 H6 0.9300
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.490(3)
C10 C15 1.384(3)
C10 C11 1.392(3)
C11 C12 1.373(3)
C11 H11 0.9300
C12 C13 1.382(3)
C12 H12 0.9300
C13 C14 1.380(3)
C13 C16 1.503(3)
C14 C15 1.380(3)
C14 H14 0.9300
C15 H15 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
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 H1N1 O3 4_565 0.91 2.08 2.958(2) 162
C7 H7A Cg1 0_655 0.97 2.74 3.603(3) 149
C16 H16C Cg2 0_655 0.96 2.96 3.829(2) 151
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
C7 O1 C1 C6 172.16(19)
C7 O1 C1 C2 -9.7(2)
C6 C1 C2 C3 1.8(3)
O1 C1 C2 C3 -176.41(17)
C6 C1 C2 O2 179.79(16)
O1 C1 C2 O2 1.6(2)
C7 O2 C2 C3 -174.9(2)
C7 O2 C2 C1 7.3(2)
C1 C2 C3 C4 -0.9(3)
O2 C2 C3 C4 -178.44(19)
C2 C3 C4 C5 -0.7(3)
C3 C4 C5 C6 1.5(3)
C3 C4 C5 C8 -176.20(18)
C2 C1 C6 C5 -1.0(3)
O1 C1 C6 C5 176.87(17)
C4 C5 C6 C1 -0.6(3)
C8 C5 C6 C1 177.12(16)
C1 O1 C7 O2 14.2(2)
C2 O2 C7 O1 -13.3(2)
C9 N1 C8 C5 93.3(2)
C4 C5 C8 N1 108.75(19)
C6 C5 C8 N1 -68.9(2)
C8 N1 C9 O3 2.1(3)
C8 N1 C9 C10 -176.54(15)
O3 C9 C10 C15 20.0(3)
N1 C9 C10 C15 -161.38(17)
O3 C9 C10 C11 -158.13(18)
N1 C9 C10 C11 20.5(3)
C15 C10 C11 C12 -0.1(3)
C9 C10 C11 C12 178.03(17)
C10 C11 C12 C13 0.6(3)
C11 C12 C13 C14 0.0(3)
C11 C12 C13 C16 -179.77(18)
C12 C13 C14 C15 -1.1(3)
C16 C13 C14 C15 178.62(18)
C13 C14 C15 C10 1.7(3)
C11 C10 C15 C14 -1.1(3)
C9 C10 C15 C14 -179.27(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 765339
2 PubChem 876425
