#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/44/2204498.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_2204498
loop_
_publ_author_name
'Parvez, Masood'
'Shahzadi, Saira'
'Shahid, Khadija'
'Ali, Saqib'
_publ_section_title
;
 3-[(2,4,6-Trichloroanilino)carbonyl]prop-2-enoic acid
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2082
_journal_page_last               o2084
_journal_paper_doi               10.1107/S1600536804026030
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C10 H6 Cl3 N O3'
_chemical_formula_moiety         'C10 H6 Cl3 N O3'
_chemical_formula_sum            'C10 H6 Cl3 N O3'
_chemical_formula_weight         294.51
_chemical_name_systematic
;
3-[(2,4,6-Trichloroanilino)carbonyl]prop-2-enoic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.372(7)
_cell_angle_beta                 102.792(8)
_cell_angle_gamma                92.732(9)
_cell_formula_units_Z            4
_cell_length_a                   7.0620(10)
_cell_length_b                   12.665(2)
_cell_length_c                   13.875(3)
_cell_measurement_reflns_used    10295
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     1193.2(4)
_computing_cell_refinement       'HKL DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SAPI91 (Fan, 1991)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'ω and φ '
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.046
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10295
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.3
_exptl_absorpt_coefficient_mu    0.76
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.066
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.050P)²+0.16P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.091
_refine_ls_wR_factor_ref         0.104
_reflns_number_gt                3762
_reflns_number_total             5428
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            fl6126.cif
_cod_data_source_block           I
_cod_database_code               2204498
_cod_database_fobs_code          2204498
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
Cl1 0.32249(8) -0.17338(5) 0.19859(4) 0.05756(18) Uani d . 1 Cl
Cl2 -0.26885(10) -0.13183(5) -0.10711(4) 0.06113(19) Uani d . 1 Cl
Cl3 -0.28011(9) 0.04975(4) 0.26538(4) 0.05489(17) Uani d . 1 Cl
O1 0.3658(2) 0.31959(11) 0.63156(11) 0.0510(4) Uani d . 1 O
O2 0.2432(2) 0.29361(11) 0.46975(11) 0.0477(4) Uani d . 1 O
H1O 0.208(3) 0.245(2) 0.4182(19) 0.057 Uiso d . 1 H
O3 0.1605(3) 0.13332(10) 0.33694(10) 0.0520(4) Uani d . 1 O
N1 0.1040(2) -0.04464(12) 0.32660(12) 0.0343(4) Uani d . 1 N
H1N 0.114(3) -0.1016(18) 0.3543(16) 0.041 Uiso d . 1 H
C1 0.3028(3) 0.25810(14) 0.55428(14) 0.0363(4) Uani d . 1 C
C2 0.2942(3) 0.14136(14) 0.55833(14) 0.0365(4) Uani d . 1 C
H2 0.3352 0.1246 0.6239 0.044 Uiso calc R 1 H
C3 0.2399(3) 0.05580(14) 0.48729(14) 0.0347(4) Uani d . 1 C
H3 0.2498 -0.0118 0.5092 0.042 Uiso calc R 1 H
C4 0.1662(3) 0.05316(14) 0.37867(14) 0.0351(4) Uani d . 1 C
C5 0.0157(3) -0.06231(13) 0.22257(14) 0.0324(4) Uani d . 1 C
C6 0.1026(3) -0.12290(15) 0.15519(15) 0.0368(4) Uani d . 1 C
C7 0.0155(3) -0.14497(16) 0.05339(15) 0.0416(5) Uani d . 1 C
H7 0.0758 -0.1873 0.0083 0.050 Uiso calc R 1 H
C8 -0.1593(3) -0.10430(16) 0.01943(15) 0.0423(5) Uani d . 1 C
C9 -0.2498(3) -0.04356(16) 0.08412(15) 0.0445(5) Uani d . 1 C
H9 -0.3709 -0.0160 0.0597 0.053 Uiso calc R 1 H
C10 -0.1609(3) -0.02346(14) 0.18522(15) 0.0382(5) Uani d . 1 C
Cl4 0.20786(10) 0.54345(5) 0.19676(5) 0.06137(18) Uani d . 1 Cl
Cl5 0.27323(9) 0.32719(4) -0.15478(4) 0.05137(16) Uani d . 1 Cl
Cl6 0.83176(9) 0.31758(5) 0.17480(5) 0.06246(18) Uani d . 1 Cl
O4 0.8874(2) 0.25018(12) 0.61572(13) 0.0574(4) Uani d . 1 O
O5 0.6925(3) 0.20150(11) 0.46722(13) 0.0551(4) Uani d . 1 O
H5O 0.636(4) 0.226(2) 0.418(2) 0.066 Uiso d . 1 H
O6 0.5608(2) 0.29213(10) 0.32217(11) 0.0484(4) Uani d . 1 O
N2 0.5835(3) 0.45790(13) 0.28293(12) 0.0388(4) Uani d . 1 N
H2N 0.608(3) 0.5242(19) 0.3070(17) 0.047 Uiso d . 1 H
C11 0.7914(3) 0.27493(16) 0.53952(17) 0.0425(5) Uani d . 1 C
C12 0.7825(3) 0.39004(15) 0.52980(16) 0.0409(5) Uani d . 1 C
H12 0.8400 0.4378 0.5897 0.049 Uiso calc R 1 H
C13 0.7088(3) 0.43855(14) 0.45247(15) 0.0385(5) Uani d . 1 C
H13 0.7202 0.5146 0.4654 0.046 Uiso calc R 1 H
C14 0.6111(3) 0.38886(14) 0.34875(15) 0.0371(4) Uani d . 1 C
C15 0.5082(3) 0.42438(14) 0.17890(14) 0.0362(4) Uani d . 1 C
C16 0.3343(3) 0.45858(15) 0.13008(15) 0.0404(5) Uani d . 1 C
C17 0.2594(3) 0.42843(16) 0.02731(16) 0.0437(5) Uani d . 1 C
H17 0.1396 0.4523 -0.0048 0.052 Uiso calc R 1 H
C18 0.3628(3) 0.36341(15) -0.02646(15) 0.0409(5) Uani d . 1 C
C19 0.5366(3) 0.32834(16) 0.01881(16) 0.0438(5) Uani d . 1 C
H19 0.6062 0.2833 -0.0194 0.053 Uiso calc R 1 H
C20 0.6091(3) 0.35946(16) 0.12097(16) 0.0407(5) Uani d . 1 C
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'
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
_geom_angle_publ_flag
C1 O2 H1O 114.6(17) ?
C4 N1 C5 122.71(16) y
C4 N1 H1N 122.2(14) ?
C5 N1 H1N 115.1(14) ?
O1 C1 O2 120.79(18) ?
O1 C1 C2 118.22(18) ?
O2 C1 C2 120.99(16) ?
C3 C2 C1 132.10(18) ?
C3 C2 H2 113.9 ?
C1 C2 H2 113.9 ?
C2 C3 C4 127.96(17) ?
C2 C3 H3 116.0 ?
C4 C3 H3 116.0 ?
O3 C4 N1 121.34(18) ?
O3 C4 C3 124.10(16) ?
N1 C4 C3 114.55(16) ?
C10 C5 C6 117.82(17) ?
C10 C5 N1 121.75(17) ?
C6 C5 N1 120.40(18) ?
C5 C6 C7 121.61(19) ?
C5 C6 Cl1 119.38(15) ?
C7 C6 Cl1 119.01(16) ?
C8 C7 C6 118.64(19) ?
C8 C7 H7 120.7 ?
C6 C7 H7 120.7 ?
C7 C8 C9 121.39(18) ?
C7 C8 Cl2 118.89(17) ?
C9 C8 Cl2 119.72(17) ?
C8 C9 C10 118.9(2) ?
C8 C9 H9 120.6 ?
C10 C9 H9 120.6 ?
C5 C10 C9 121.68(19) ?
C5 C10 Cl3 120.25(15) ?
C9 C10 Cl3 118.06(17) ?
C11 O5 H5O 113.6(19) ?
C14 N2 C15 122.62(16) y
C14 N2 H2N 116.6(15) ?
C15 N2 H2N 120.7(15) ?
O4 C11 O5 120.68(19) ?
O4 C11 C12 119.4(2) ?
O5 C11 C12 119.9(2) ?
C13 C12 C11 131.8(2) ?
C13 C12 H12 114.1 ?
C11 C12 H12 114.1 ?
C12 C13 C14 128.21(18) ?
C12 C13 H13 115.9 ?
C14 C13 H13 115.9 ?
O6 C14 N2 121.34(18) ?
O6 C14 C13 124.36(18) ?
N2 C14 C13 114.28(16) ?
C16 C15 C20 117.45(18) ?
C16 C15 N2 120.93(18) ?
C20 C15 N2 121.57(19) ?
C15 C16 C17 121.94(19) ?
C15 C16 Cl4 119.62(15) ?
C17 C16 Cl4 118.42(17) ?
C18 C17 C16 118.5(2) ?
C18 C17 H17 120.7 ?
C16 C17 H17 120.7 ?
C17 C18 C19 121.44(19) ?
C17 C18 Cl5 118.95(18) ?
C19 C18 Cl5 119.59(17) ?
C18 C19 C20 119.2(2) ?
C18 C19 H19 120.4 ?
C20 C19 H19 120.4 ?
C19 C20 C15 121.4(2) ?
C19 C20 Cl6 118.03(17) ?
C15 C20 Cl6 120.54(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C6 1.725(2) y
Cl2 C8 1.731(2) y
Cl3 C10 1.730(2) y
O1 C1 1.211(2) y
O2 C1 1.307(2) y
O2 H1O 0.86(2) ?
O3 C4 1.238(2) y
N1 C4 1.340(2) y
N1 C5 1.420(2) y
N1 H1N 0.86(2) ?
C1 C2 1.487(3) ?
C2 C3 1.332(3) ?
C2 H2 0.9500 ?
C3 C4 1.476(3) ?
C3 H3 0.9500 ?
C5 C10 1.383(3) ?
C5 C6 1.389(3) ?
C6 C7 1.391(3) ?
C7 C8 1.373(3) ?
C7 H7 0.9500 ?
C8 C9 1.380(3) ?
C9 C10 1.385(3) ?
C9 H9 0.9500 ?
Cl4 C16 1.725(2) y
Cl5 C18 1.737(2) y
Cl6 C20 1.728(2) y
O4 C11 1.215(3) y
O5 C11 1.310(3) y
O5 H5O 0.83(3) ?
O6 C14 1.238(2) y
N2 C14 1.344(3) y
N2 C15 1.416(2) y
N2 H2N 0.85(2) ?
C11 C12 1.487(3) ?
C12 C13 1.332(3) ?
C12 H12 0.9500 ?
C13 C14 1.483(3) ?
C13 H13 0.9500 ?
C15 C16 1.387(3) ?
C15 C20 1.395(3) ?
C16 C17 1.395(3) ?
C17 C18 1.374(3) ?
C17 H17 0.9500 ?
C18 C19 1.375(3) ?
C19 C20 1.387(3) ?
C19 H19 0.9500 ?
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
O2 H1O O3 . 0.86(2) 1.64(3) 2.486(2) 167(2)
N1 H1N O4 2_656 0.86(2) 1.99(2) 2.832(2) 166(2)
O5 H5O O6 . 0.83(3) 1.67(3) 2.486(2) 169(3)
N2 H2N O1 2_666 0.85(2) 2.02(2) 2.867(2) 173(2)
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
O1 C1 C2 C3 -177.4(2)
O2 C1 C2 C3 2.9(3)
C1 C2 C3 C4 -1.0(4)
C5 N1 C4 O3 -4.5(3)
C5 N1 C4 C3 175.49(17)
C2 C3 C4 O3 6.5(3)
C2 C3 C4 N1 -173.5(2)
C4 N1 C5 C10 -64.6(3)
C4 N1 C5 C6 117.6(2)
C10 C5 C6 C7 -0.4(3)
N1 C5 C6 C7 177.46(16)
C10 C5 C6 Cl1 -179.75(14)
N1 C5 C6 Cl1 -1.9(2)
C5 C6 C7 C8 0.8(3)
Cl1 C6 C7 C8 -179.86(15)
C6 C7 C8 C9 -0.7(3)
C6 C7 C8 Cl2 -179.78(14)
C7 C8 C9 C10 0.2(3)
Cl2 C8 C9 C10 179.26(15)
C6 C5 C10 C9 -0.1(3)
N1 C5 C10 C9 -177.97(17)
C6 C5 C10 Cl3 178.37(14)
N1 C5 C10 Cl3 0.5(2)
C8 C9 C10 C5 0.3(3)
C8 C9 C10 Cl3 -178.26(15)
O4 C11 C12 C13 171.4(2)
O5 C11 C12 C13 -10.2(4)
C11 C12 C13 C14 -0.6(4)
C15 N2 C14 O6 -4.4(3)
C15 N2 C14 C13 174.37(18)
C12 C13 C14 O6 10.1(4)
C12 C13 C14 N2 -168.6(2)
C14 N2 C15 C16 118.5(2)
C14 N2 C15 C20 -64.1(3)
C20 C15 C16 C17 1.1(3)
N2 C15 C16 C17 178.62(17)
C20 C15 C16 Cl4 -177.37(15)
N2 C15 C16 Cl4 0.2(3)
C15 C16 C17 C18 -0.4(3)
Cl4 C16 C17 C18 178.09(15)
C16 C17 C18 C19 -0.1(3)
C16 C17 C18 Cl5 -178.91(14)
C17 C18 C19 C20 -0.1(3)
Cl5 C18 C19 C20 178.67(15)
C18 C19 C20 C15 0.9(3)
C18 C19 C20 Cl6 -177.91(15)
C16 C15 C20 C19 -1.3(3)
N2 C15 C20 C19 -178.84(17)
C16 C15 C20 Cl6 177.41(14)
N2 C15 C20 Cl6 -0.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1371347
