#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/67/2226718.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_2226718
loop_
_publ_author_name
'Naveen, S.'
Basappa
'Manjunath, H. R.'
'Sridhar, M. A.'
'Shashidhara Prasad, J.'
'Rangappa, K. S.'
_publ_section_title
;
 N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-ethoxybenzamide
;
_journal_coeditor_code           WN2389
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1533
_journal_paper_doi               10.1107/S1600536810019811
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H13 F3 N2 O2'
_chemical_formula_moiety         'C17 H13 F3 N2 O2'
_chemical_formula_sum            'C17 H13 F3 N2 O2'
_chemical_formula_weight         334.29
_chemical_name_systematic
;
N-(4-cyano-3-(trifluromethyl)phenyl)-2-ethoxybenzamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.653(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5010(13)
_cell_length_b                   12.8830(16)
_cell_length_c                   11.6130(14)
_cell_measurement_temperature    293(2)
_cell_volume                     1538.7(3)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'XPRESS (MacScience, 2002)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and SCALEPACK'
_computing_molecular_graphics
'PLATON (Spek, 2009) and ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'MacScience DIPLabo 32001'
_diffrn_measurement_method       'ω scan'
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5043
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.39
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          .32
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .27
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.192
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1179P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1764
_reflns_number_gt                1896
_reflns_number_total             2704
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            wn2389.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226718
_cod_database_fobs_code          2226718
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 N7 0.87506(17) 0.12966(13) 0.60529(15) 0.0493(5) Uani d . 1 . .
H H1 0.8991 0.0685 0.6519 0.059 Uiso d R 1 . .
O O24 0.7968(2) 0.17185(12) 0.41408(15) 0.0740(6) Uani d . 1 . .
O O15 0.89269(17) -0.07252(11) 0.65288(15) 0.0610(5) Uani d . 1 . .
F F21 0.75451(17) 0.57018(11) 0.62234(16) 0.0844(5) Uani d . 1 . .
F F22 0.79874(19) 0.49654(12) 0.47046(14) 0.0996(7) Uani d . 1 . .
C C6 0.9373(2) 0.23273(17) 0.7779(2) 0.0566(6) Uani d . 1 . .
H H6 0.9602 0.1701 0.8220 0.068 Uiso d R 1 . .
C C14 0.8480(2) -0.09241(16) 0.5358(2) 0.0513(6) Uani d . 1 . .
C C5 0.8896(2) 0.22760(15) 0.6581(2) 0.0474(5) Uani d . 1 . .
C C9 0.8176(2) -0.00775(16) 0.45831(19) 0.0489(5) Uani d . 1 . .
C C2 0.9212(2) 0.41873(16) 0.7744(2) 0.0537(6) Uani d . 1 . .
C C8 0.8285(2) 0.10574(17) 0.4903(2) 0.0501(6) Uani d . 1 . .
F F23 0.94844(17) 0.57372(11) 0.59172(17) 0.0881(6) Uani d . 1 . .
C C10 0.7724(2) -0.0286(2) 0.3392(2) 0.0608(6) Uani d . 1 . .
H H13 0.7506 0.0277 0.2847 0.073 Uiso d R 1 . .
C C4 0.8589(2) 0.31994(16) 0.5946(2) 0.0516(6) Uani d . 1 . .
H H14 0.8274 0.3167 0.5111 0.062 Uiso d R 1 . .
C C18 0.9345(2) 0.51680(19) 0.8361(2) 0.0638(6) Uani d . 1 . .
C C1 0.9528(2) 0.32671(18) 0.8361(2) 0.0602(6) Uani d . 1 . .
H H16 0.9846 0.3279 0.9196 0.072 Uiso d R 1 . .
C C3 0.8748(2) 0.41397(16) 0.6531(2) 0.0519(6) Uani d . 1 . .
C C13 0.8323(3) -0.19283(18) 0.4910(2) 0.0645(7) Uani d . 1 . .
H H18 0.8507 -0.2510 0.5433 0.077 Uiso d R 1 . .
N N19 0.9424(3) 0.59476(17) 0.8833(2) 0.0817(7) Uani d . 1 . .
C C20 0.8439(3) 0.51243(18) 0.5837(2) 0.0641(7) Uani d . 1 . .
C C16 0.9363(3) -0.15806(18) 0.7317(2) 0.0650(7) Uani d . 1 . .
H H21A 0.8635 -0.2019 0.7358 0.078 Uiso d R 1 . .
H H21B 1.0002 -0.1970 0.7014 0.078 Uiso d R 1 . .
C C11 0.7590(3) -0.1291(2) 0.2959(2) 0.0684(7) Uani d . 1 . .
H H22 0.7290 -0.1410 0.2133 0.082 Uiso d R 1 . .
C C12 0.7889(3) -0.2104(2) 0.3733(3) 0.0699(7) Uani d . 1 . .
H H23 0.7802 -0.2804 0.3444 0.084 Uiso d R 1 . .
C C17 0.9919(3) -0.1132(2) 0.8500(2) 0.0771(8) Uani d . 1 . .
H H24A 1.0226 -0.1674 0.9054 0.092 Uiso d R 1 . .
H H24B 0.9264 -0.0736 0.8771 0.092 Uiso d R 1 . .
H H24C 1.0631 -0.0686 0.8426 0.092 Uiso d 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 0.0000 0.0000 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C8 N7 C5 . . 128.36(18) ?
C8 N7 H1 . . 111.7 ?
C5 N7 H1 . . 120.0 ?
C14 O15 C16 . . 119.14(18) ?
C1 C6 C5 . . 121.2(2) ?
C1 C6 H6 . . 118.9 ?
C5 C6 H6 . . 119.9 ?
O15 C14 C13 . . 122.4(2) ?
O15 C14 C9 . . 118.49(19) ?
C13 C14 C9 . . 119.1(2) ?
C6 C5 N7 . . 118.07(19) ?
C6 C5 C4 . . 119.1(2) ?
N7 C5 C4 . . 122.8(2) ?
C10 C9 C14 . . 118.1(2) ?
C10 C9 C8 . . 115.14(19) ?
C14 C9 C8 . . 126.7(2) ?
C1 C2 C3 . . 118.8(2) ?
C1 C2 C18 . . 120.0(2) ?
C3 C2 C18 . . 121.2(2) ?
O24 C8 N7 . . 122.9(2) ?
O24 C8 C9 . . 120.1(2) ?
N7 C8 C9 . . 117.08(18) ?
C11 C10 C9 . . 122.0(2) ?
C11 C10 H13 . . 118.2 ?
C9 C10 H13 . . 119.8 ?
C3 C4 C5 . . 119.5(2) ?
C3 C4 H14 . . 121.1 ?
C5 C4 H14 . . 119.4 ?
N19 C18 C2 . . 178.5(3) ?
C6 C1 C2 . . 120.2(2) ?
C6 C1 H16 . . 119.4 ?
C2 C1 H16 . . 120.3 ?
C4 C3 C2 . . 121.2(2) ?
C4 C3 C20 . . 119.0(2) ?
C2 C3 C20 . . 119.9(2) ?
C12 C13 C14 . . 121.1(2) ?
C12 C13 H18 . . 119.2 ?
C14 C13 H18 . . 119.7 ?
F22 C20 F23 . . 106.6(2) ?
F22 C20 F21 . . 106.5(2) ?
F23 C20 F21 . . 105.6(2) ?
F22 C20 C3 . . 113.5(2) ?
F23 C20 C3 . . 112.1(2) ?
F21 C20 C3 . . 112.2(2) ?
O15 C16 C17 . . 107.6(2) ?
O15 C16 H21A . . 109.1 ?
C17 C16 H21A . . 110.4 ?
O15 C16 H21B . . 108.7 ?
C17 C16 H21B . . 111.5 ?
H21A C16 H21B . . 109.5 ?
C12 C11 C10 . . 118.8(2) ?
C12 C11 H22 . . 121.2 ?
C10 C11 H22 . . 120.1 ?
C13 C12 C11 . . 120.9(2) ?
C13 C12 H23 . . 119.5 ?
C11 C12 H23 . . 119.7 ?
C16 C17 H24A . . 110.5 ?
C16 C17 H24B . . 109.5 ?
H24A C17 H24B . . 109.5 ?
C16 C17 H24C . . 108.4 ?
H24A C17 H24C . . 109.5 ?
H24B C17 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
N7 C8 . 1.362(3) ?
N7 C5 . 1.398(3) ?
N7 H1 . 0.9600 ?
O24 C8 . 1.225(3) ?
O15 C14 . 1.370(3) ?
O15 C16 . 1.447(3) ?
F21 C20 . 1.344(3) ?
F22 C20 . 1.321(3) ?
C6 C1 . 1.380(3) ?
C6 C5 . 1.381(3) ?
C6 H6 . 0.9600 ?
C14 C13 . 1.392(3) ?
C14 C9 . 1.409(3) ?
C5 C4 . 1.403(3) ?
C9 C10 . 1.395(3) ?
C9 C8 . 1.507(3) ?
C2 C1 . 1.390(3) ?
C2 C3 . 1.395(3) ?
C2 C18 . 1.445(3) ?
F23 C20 . 1.340(3) ?
C10 C11 . 1.386(3) ?
C10 H13 . 0.9600 ?
C4 C3 . 1.382(3) ?
C4 H14 . 0.9598 ?
C18 N19 . 1.139(3) ?
C1 H16 . 0.9599 ?
C3 C20 . 1.503(3) ?
C13 C12 . 1.370(4) ?
C13 H18 . 0.9600 ?
C16 C17 . 1.496(4) ?
C16 H21A . 0.9600 ?
C16 H21B . 0.9599 ?
C11 C12 . 1.374(4) ?
C11 H22 . 0.9600 ?
C12 H23 . 0.9601 ?
C17 H24A . 0.9600 ?
C17 H24B . 0.9600 ?
C17 H24C . 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
_geom_hbond_publ_flag
N7 H1 O15 - 0.96 1.82 2.661(2) 145 yes
C1 H16 N19 3_767 0.96 2.47 3.377(3) 157 yes
C13 H18 F23 1_545 0.96 2.50 3.365(3) 150 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745183
2 PubChem 68453779
