#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/37/2003766.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_2003766
loop_
_publ_author_name
'Chen, C.-F.'
'Xu, J.-H.'
'Liu, Y.-C.'
'Xu, C.'
_publ_section_title
;
 2,3,5,6-Tetrachloro-4-hydroxyphenyl
 <i>N</i>-(4-Chlorophenyl)benzenecarboximidate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1709
_journal_page_last               1711
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source        Recrystallized
_chemical_formula_sum            'C19 H10 Cl5 N O2'
_chemical_formula_weight         461.6
_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_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 95.96(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.853(3)
_cell_length_b                   11.025(1)
_cell_length_c                   22.708(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     1955.4(9)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3917
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.76
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_type   'empirical, based on \y scan'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       Prism
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.50
_refine_diff_density_min         0.10
_refine_ls_goodness_of_fit_obs   1.35
_refine_ls_hydrogen_treatment    'H atoms refined as fixed B~iso~'
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2156
_refine_ls_R_factor_obs          0.050
_refine_ls_shift/esd_max         0.01
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         0.047
_reflns_number_observed          2156
_reflns_number_total             3633
_reflns_observed_criterion       I>=3\s(I)
_[local]_cod_data_source_file    cr1132.cif
_[local]_cod_data_source_block   cr1132a
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_[local]_cod_chemical_formula_sum_orig 'C19 H10 Cl5 N1 O2'
_cod_original_cell_volume        1955.4(X)
_cod_database_code               2003766
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,1/2+z
-x,-y,-z
1/2-x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
Cl(1) .4140(2) .0216(2) .79492(6) 6.89(4)
Cl(2) .8169(2) .0074(2) 1.04446(6) 6.89(4)
Cl(3) .8290(2) -.2155(2) .95620(7) 6.80(4)
Cl(4) .4027(2) .2437(1) .88124(7) 7.23(4)
Cl(5) -.1543(2) -.6194(2) .90663(8) 7.80(4)
C(1) .5275(6) .0192(5) .8639(2) 4.5(1)
C(2) .5228(6) .1172(5) .9018(2) 4.8(1)
C(3) .6093(6) .1127(4) .9577(2) 4.7(1)
C(4) .7062(6) .0102(5) .9746(2) 4.7(1)
C(5) .7100(6) -.0888(5) .9360(2) 4.6(1)
C(6) .6170(6) -.0830(4) .8813(2) 4.0(1)
C(7) .2735(6) -.3565(4) .8858(2) 3.8(1)
C(8) .1300(6) -.3581(5) .8456(2) 4.5(1)
C(9) -.0010(6) -.4389(5) .8508(2) 5.0(1)
C(10) .0150(6) -.5187(5) .8978(2) 4.8(1)
C(11) .1525(7) -.5179(5) .9386(2) 5.2(1)
C(12) .2839(7) -.4363(5) .9333(2) 5.0(1)
O(1) .5964(5) .2096(3) .9930(2) 6.8(1)
C(13) .5198(6) -.3550(4) .7940(2) 4.0(1)
C(14) .5120(6) -.4783(4) .8032(2) 3.8(1)
C(15) .5284(7) -.5591(5) .7576(2) 3.9(1)
C(16) .5501(7) -.5153(5) .7016(2) 5.7(1)
C(17) .5580(7) -.3937(6) .6921(2) 6.2(1)
C(18) .5461(7) -.3121(5) .7380(2) 5.3(1)
O(2) .6242(4) -.1785(3) .8417(1) 5.72(7)
C(19) .5057(6) -.2698(4) .8427(2) 4.2(1)
N(1) .4070(5) -.2684(4) .8837(2) 4.27(9)
H1 .543 -.218 .736 4.0
H2 .584 -.359 .653 4.0
H3 .541 -.583 .667 4.0
H4 .540 -.667 .764 4.0
H5 .500 -.499 .845 4.0
H6 .124 -.281 .820 4.0
H7 -.127 -.419 .820 4.0
H8 .165 -.583 .970 4.0
H9 .377 -.443 .973 4.0
H10 .582 .193 1.040 4.0
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
Cl(1) C(1) C(2) 120.6(4) yes
Cl(1) C(1) C(6) 118.6(3) yes
C(2) C(1) C(6) 120.8(4) yes
Cl(4) C(2) C(1) 120.9(4) yes
Cl(4) C(2) C(3) 118.8(4) yes
C(1) C(2) C(3) 120.2(5) yes
C(2) C(3) C(4) 119.0(4) yes
C(2) C(3) O(1) 117.4(5) yes
C(4) C(3) O(1) 123.6(5) yes
Cl(2) C(4) C(3) 118.3(4) yes
Cl(2) C(4) C(5) 121.3(4) yes
C(3) C(4) C(5) 120.4(4) yes
Cl(3) C(5) C(4) 120.8(4) yes
Cl(3) C(5) C(6) 120.2(4) yes
C(4) C(5) C(6) 119.0(4) yes
C(1) C(6) C(5) 120.6(4) yes
C(1) C(6) O(2) 119.6(4) yes
C(5) C(6) O(2) 119.7(4) yes
C(8) C(7) C(12) 119.1(4) yes
C(8) C(7) N(1) 122.6(4) yes
C(12) C(7) N(1) 118.2(4) yes
C(7) C(8) C(9) 121.3(4) yes
C(8) C(9) C(10) 118.5(4) yes
Cl(5) C(10) C(9) 119.1(4) yes
Cl(5) C(10) C(11) 119.1(4) yes
C(9) C(10) C(11) 122.0(4) yes
C(10) C(11) C(12) 119.7(4) yes
C(7) C(12) C(11) 119.7(4) yes
C(14) C(13) C(18) 119.2(4) yes
C(14) C(13) C(19) 120.6(4) yes
C(18) C(13) C(19) 120.1(4) yes
C(13) C(14) C(15) 120.8(4) yes
C(14) C(15) C(16) 119.6(5) yes
C(15) C(16) C(17) 120.0(4) yes
C(16) C(17) C(18) 120.8(5) yes
C(13) C(18) C(17) 119.6(4) yes
C(6) O(2) C(19) 118.2(3) yes
C(13) C(19) O(2) 110.7(3) yes
C(13) C(19) N(1) 131.3(4) yes
O(2) C(19) N(1) 118.0(4) yes
C(19) N(1) C(7) 121.3(3) yes
C(7) C(8) H6 110.7(4) no
C(9) C(8) H6 126.3(5) no
C(8) C(9) H7 114.7(4) no
C(10) C(9) H7 125.3(4) no
C(10) C(11) H8 119.4(4) no
C(12) C(11) H8 120.5(5) no
C(7) C(12) H9 131.3(4) no
C(11) C(12) H9 108.6(4) no
C(3) O(1) H10 118.2(3) no
C(13) C(14) H5 112.8(4) no
C(15) C(14) H5 126.3(5) no
C(14) C(15) H4 124.2(5) no
C(16) C(15) H4 115.9(4) no
C(15) C(16) H3 115.1(5) no
C(17) C(16) H3 124.3(5) no
C(16) C(17) H2 122.4(5) no
C(18) C(17) H2 116.5(6) no
C(13) C(18) H1 112.0(4) no
C(17) C(18) H1 128.1(5) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(1) C(1) 1.720(5) yes
Cl(2) C(4) 1.728(4) yes
Cl(3) C(5) 1.716(5) yes
Cl(4) C(2) 1.721(5) yes
Cl(5) C(10) 1.760(4) yes
C(1) C(2) 1.383(6) yes
C(1) C(6) 1.365(6) yes
C(2) C(3) 1.378(6) yes
C(3) C(4) 1.394(7) yes
C(3) O(1) 1.345(5) yes
C(4) C(5) 1.402(6) yes
C(5) C(6) 1.375(6) yes
C(6) O(2) 1.389(5) yes
C(7) C(8) 1.375(6) yes
C(7) C(12) 1.387(6) yes
C(7) N(1) 1.433(5) yes
C(8) C(9) 1.370(6) yes
C(9) C(10) 1.378(6) yes
C(10) C(11) 1.348(6) yes
C(11) C(12) 1.383(6) yes
C(13) C(14) 1.378(6) yes
C(13) C(18) 1.391(6) yes
C(13) C(19) 1.465(5) yes
C(14) C(15) 1.382(6) yes
C(15) C(16) 1.387(7) yes
C(16) C(17) 1.361(7) yes
C(17) C(18) 1.388(6) yes
C(19) O(2) 1.372(5) yes
C(19) N(1) 1.272(5) yes
C(8) H6 1.028(4) no
C(9) H7 1.177(4) no
C(11) H8 1.008(4) no
C(12) H9 1.103(4) no
O(1) H10 1.108(3) no
C(14) H5 0.990(5) no
C(15) H4 1.201(5) no
C(16) H3 1.081(5) no
C(17) H2 1.007(5) no
C(18) H1 1.038(5) no
_journal_paper_doi 10.1107/S0108270195001247