#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/71/2227189.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_2227189
loop_
_publ_author_name
'Xiao, Zhu-Ping'
'Wang, Xu-Dong'
'Liu, Tian'
'Zhu, Jian'
'Li, Zhi-Ping'
_publ_section_title
;
 (Z)-Ethyl
 2-(4-chlorophenyl)-3-[(2,4-difluorophenyl)amino]prop-2-enoate
;
_journal_coeditor_code           BQ2244
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3016
_journal_paper_doi               10.1107/S1600536810043801
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H14 Cl F2 N O2'
_chemical_formula_moiety         'C17 H14 Cl F2 N O2'
_chemical_formula_sum            'C17 H14 Cl F2 N O2'
_chemical_formula_weight         337.74
_chemical_name_systematic
;
(Z)-Ethyl 2-(4-chlorophenyl)-3-[(2,4-difluorophenyl)amino]prop-2-enoate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.11(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.276(3)
_cell_length_b                   7.5030(15)
_cell_length_c                   13.812(3)
_cell_measurement_reflns_used    1318
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.65
_cell_measurement_theta_min      1.83
_cell_volume                     1573.5(6)
_computing_cell_refinement       'SMART (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART 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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2957
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.34
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_correction_T_min  0.9229
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0648
_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)+(0.0804P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1703
_reflns_number_gt                1566
_reflns_number_total             2824
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2244.cif
_cod_data_source_block           I
_cod_original_cell_volume        1573.5(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227189
_cod_database_fobs_code          2227189
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
C C1 1.0185(2) 0.7793(5) 0.9700(2) 0.0447(9) Uani d . 1 . .
C C2 1.1023(2) 0.7723(5) 1.0451(2) 0.0473(9) Uani d . 1 . .
C C3 1.1764(2) 0.8338(5) 1.0316(3) 0.0575(10) Uani d . 1 . .
H H3 1.2316 0.8267 1.0841 0.069 Uiso calc R 1 . .
C C4 1.1653(2) 0.9062(6) 0.9370(3) 0.0591(10) Uani d . 1 . .
C C5 1.0852(3) 0.9180(5) 0.8598(3) 0.0614(11) Uani d . 1 . .
H H5 1.0799 0.9696 0.7966 0.074 Uiso calc R 1 . .
C C6 1.0122(2) 0.8536(5) 0.8756(3) 0.0561(10) Uani d . 1 . .
H H6 0.9575 0.8598 0.8222 0.067 Uiso calc R 1 . .
C C7 0.7054(2) 0.6470(5) 0.8669(2) 0.0418(8) Uani d . 1 . .
C C8 0.6325(2) 0.7235(5) 0.8805(3) 0.0534(10) Uani d . 1 . .
H H8 0.6377 0.7669 0.9456 0.064 Uiso calc R 1 . .
C C9 0.5528(2) 0.7365(5) 0.7997(3) 0.0568(10) Uani d . 1 . .
H H9 0.5046 0.7872 0.8103 0.068 Uiso calc R 1 . .
C C10 0.5451(2) 0.6741(5) 0.7036(3) 0.0538(10) Uani d . 1 . .
C C11 0.6148(2) 0.5949(5) 0.6881(3) 0.0567(10) Uani d . 1 . .
H H11 0.6087 0.5507 0.6229 0.068 Uiso calc R 1 . .
C C12 0.6946(2) 0.5807(5) 0.7697(2) 0.0474(9) Uani d . 1 . .
H H12 0.7418 0.5255 0.7590 0.057 Uiso calc R 1 . .
C C13 0.8638(2) 0.7024(5) 0.9292(2) 0.0463(9) Uani d . 1 . .
H H13 0.8524 0.7370 0.8610 0.056 Uiso calc R 1 . .
C C14 0.7936(2) 0.6482(5) 0.9515(2) 0.0423(8) Uani d . 1 . .
C C15 0.8066(2) 0.5946(5) 1.0578(2) 0.0480(9) Uani d . 1 . .
C C16 0.7412(2) 0.4743(6) 1.1713(2) 0.0622(11) Uani d . 1 . .
H H16A 0.7579 0.5751 1.2184 0.075 Uiso calc R 1 . .
H H16B 0.7856 0.3821 1.1972 0.075 Uiso calc R 1 . .
C C17 0.6536(2) 0.4057(6) 1.1638(3) 0.0708(12) Uani d . 1 . .
H H17A 0.6094 0.4936 1.1312 0.106 Uiso calc R 1 . .
H H17B 0.6540 0.3807 1.2321 0.106 Uiso calc R 1 . .
H H17C 0.6408 0.2985 1.1231 0.106 Uiso calc R 1 . .
Cl Cl1 0.44479(7) 0.69755(18) 0.60035(8) 0.0887(5) Uani d . 1 . .
F F1 1.10991(12) 0.7013(3) 1.13887(14) 0.0654(7) Uani d . 1 . .
F F2 1.23767(15) 0.9700(4) 0.92091(18) 0.0856(8) Uani d . 1 . .
N N1 0.94818(18) 0.7123(4) 0.9939(2) 0.0483(8) Uani d . 1 . .
O O1 0.87698(16) 0.6036(4) 1.13063(17) 0.0660(8) Uani d . 1 . .
O O2 0.73408(15) 0.5283(3) 1.06790(16) 0.0521(7) Uani d . 1 . .
H H18 0.961(2) 0.673(4) 1.054(3) 0.050(11) Uiso d . 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 . . 116.0(3) ?
C2 C1 N1 . . 118.7(3) ?
C6 C1 N1 . . 125.3(3) ?
F1 C2 C3 . . 118.6(3) ?
F1 C2 C1 . . 117.0(3) ?
C3 C2 C1 . . 124.4(3) ?
C2 C3 C4 . . 116.4(3) ?
C2 C3 H3 . . 121.8 ?
C4 C3 H3 . . 121.8 ?
C5 C4 F2 . . 119.4(4) ?
C5 C4 C3 . . 122.5(4) ?
F2 C4 C3 . . 118.1(4) ?
C4 C5 C6 . . 119.6(4) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C5 C6 C1 . . 121.1(3) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
C12 C7 C8 . . 117.7(3) ?
C12 C7 C14 . . 120.8(3) ?
C8 C7 C14 . . 121.3(3) ?
C9 C8 C7 . . 121.3(3) ?
C9 C8 H8 . . 119.3 ?
C7 C8 H8 . . 119.3 ?
C10 C9 C8 . . 119.5(4) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C11 C10 C9 . . 120.7(3) ?
C11 C10 Cl1 . . 120.1(3) ?
C9 C10 Cl1 . . 119.3(3) ?
C10 C11 C12 . . 119.7(3) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
C7 C12 C11 . . 121.1(3) ?
C7 C12 H12 . . 119.4 ?
C11 C12 H12 . . 119.4 ?
N1 C13 C14 . . 127.8(3) ?
N1 C13 H13 . . 116.1 ?
C14 C13 H13 . . 116.1 ?
C13 C14 C15 . . 119.0(3) ?
C13 C14 C7 . . 118.7(3) ?
C15 C14 C7 . . 122.4(3) ?
O1 C15 O2 . . 122.4(3) ?
O1 C15 C14 . . 124.3(3) ?
O2 C15 C14 . . 113.2(3) ?
O2 C16 C17 . . 107.1(3) ?
O2 C16 H16A . . 110.3 ?
C17 C16 H16A . . 110.3 ?
O2 C16 H16B . . 110.3 ?
C17 C16 H16B . . 110.3 ?
H16A C16 H16B . . 108.6 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C13 N1 C1 . . 126.4(3) ?
C13 N1 H18 . . 118(2) ?
C1 N1 H18 . . 116(2) ?
C15 O2 C16 . . 116.6(3) ?
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
C1 C2 . 1.385(4) ?
C1 C6 . 1.387(5) ?
C1 N1 . 1.394(4) ?
C2 F1 . 1.365(4) ?
C2 C3 . 1.365(5) ?
C3 C4 . 1.366(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.357(5) ?
C4 F2 . 1.362(4) ?
C5 C6 . 1.371(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.383(4) ?
C7 C8 . 1.390(5) ?
C7 C14 . 1.489(4) ?
C8 C9 . 1.377(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.370(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.364(5) ?
C10 Cl1 . 1.747(3) ?
C11 C12 . 1.384(5) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 N1 . 1.344(4) ?
C13 C14 . 1.348(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.463(4) ?
C15 O1 . 1.225(4) ?
C15 O2 . 1.333(4) ?
C16 O2 . 1.449(4) ?
C16 C17 . 1.484(5) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
N1 H18 . 0.83(3) ?
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 H18 F1 . 0.83(3) 2.29(3) 2.674(3) 108(3)
N1 H18 O1 . 0.83(3) 2.07(3) 2.675(4) 129(3)
C6 H6 O1 4_575 0.93 2.51 3.321(4) 146.0
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 F1 . . . . 179.4(3) ?
N1 C1 C2 F1 . . . . -0.8(5) ?
C6 C1 C2 C3 . . . . 0.4(6) ?
N1 C1 C2 C3 . . . . -179.8(4) ?
F1 C2 C3 C4 . . . . -179.0(3) ?
C1 C2 C3 C4 . . . . -0.1(6) ?
C2 C3 C4 C5 . . . . 0.3(6) ?
C2 C3 C4 F2 . . . . 179.6(3) ?
F2 C4 C5 C6 . . . . 179.8(4) ?
C3 C4 C5 C6 . . . . -0.9(6) ?
C4 C5 C6 C1 . . . . 1.2(6) ?
C2 C1 C6 C5 . . . . -1.0(5) ?
N1 C1 C6 C5 . . . . 179.2(4) ?
C12 C7 C8 C9 . . . . -1.3(6) ?
C14 C7 C8 C9 . . . . 174.2(3) ?
C7 C8 C9 C10 . . . . -0.5(6) ?
C8 C9 C10 C11 . . . . 1.9(6) ?
C8 C9 C10 Cl1 . . . . -177.9(3) ?
C9 C10 C11 C12 . . . . -1.3(6) ?
Cl1 C10 C11 C12 . . . . 178.5(3) ?
C8 C7 C12 C11 . . . . 1.9(5) ?
C14 C7 C12 C11 . . . . -173.6(3) ?
C10 C11 C12 C7 . . . . -0.6(6) ?
N1 C13 C14 C15 . . . . 1.0(6) ?
N1 C13 C14 C7 . . . . -179.7(3) ?
C12 C7 C14 C13 . . . . 44.5(5) ?
C8 C7 C14 C13 . . . . -130.9(4) ?
C12 C7 C14 C15 . . . . -136.2(3) ?
C8 C7 C14 C15 . . . . 48.4(5) ?
C13 C14 C15 O1 . . . . 3.8(6) ?
C7 C14 C15 O1 . . . . -175.5(4) ?
C13 C14 C15 O2 . . . . -174.1(3) ?
C7 C14 C15 O2 . . . . 6.5(5) ?
C14 C13 N1 C1 . . . . -175.8(4) ?
C2 C1 N1 C13 . . . . -177.2(3) ?
C6 C1 N1 C13 . . . . 2.6(6) ?
O1 C15 O2 C16 . . . . 2.9(5) ?
C14 C15 O2 C16 . . . . -179.2(3) ?
C17 C16 O2 C15 . . . . 180.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23331647
2 PubChem 25111240
