#------------------------------------------------------------------------------
#$Date: 2016-02-19 14:29:56 +0000 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/51/2005177.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_2005177
loop_
_publ_author_name
'Lalancette, R. A.'
'Stringer, J. A.'
'Cot\'e, M. L.'
_publ_section_title
;
 2,4,6-Trichlorobenzoic Acid: Structure and Hydrogen-Bonding Pattern
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1801
_journal_page_last               1804
_journal_paper_doi               10.1107/S0108270196001369
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C7 H3 Cl3 O2'
_chemical_formula_sum            'C7 H3 Cl3 O2'
_chemical_formula_weight         225.5
_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                90.0
_cell_angle_beta                 90.779(9)
_cell_angle_gamma                90.0
_cell_formula_units_Z            12
_cell_length_a                   7.2590(10)
_cell_length_b                   12.204(2)
_cell_length_c                   30.275(3)
_cell_measurement_reflns_used    43
_cell_measurement_temperature    296
_cell_measurement_theta_max      17.7
_cell_measurement_theta_min      11.1
_cell_volume                     2681.8(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  SHELXTL/PC
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1990)'
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8305
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        5.53
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.98
_exptl_absorpt_correction_T_max  0.799
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   'Face-indexed numerical'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_meas      1.674(2)
_exptl_crystal_density_method    'floatation in cyclohexane/CBrCl~3~'
_exptl_crystal_description       Trapezoid
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.33
_refine_ls_extinction_coef       '\c = 0.0006(1)'
_refine_ls_extinction_method     F^*^=F/[1.0+0.002\cF^2^/sin(2\q)]^1/4^
_refine_ls_goodness_of_fit_obs   1.03
_refine_ls_number_parameters     336
_refine_ls_number_reflns         2551
_refine_ls_R_factor_obs          0.045
_refine_ls_shift/esd_max         0.130
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.047
_reflns_number_observed          2551
_reflns_number_total             6172
_reflns_observed_criterion       >4\s(F)
_cod_data_source_file            pt1041.cif
_cod_data_source_block           lalancette
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2681.7(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2005177
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
1/2+x,1/2-y,1/2+z
1/2-x,1/2+y,1/2-z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl(1A) .0670(10) .1040(10) .0430(10) .0250(10) -.0050(10) .0070(10)
Cl(2A) .0650(10) .0820(10) .0470(10) .0100(10) .0180(10) -.0060(10)
Cl(3A) .0450(10) .0870(10) .0660(10) .0200(10) -.0050(10) .0060(10)
O(1A) .069(3) .056(2) .061(2) .000(2) .029(2) -.015(2)
O(2A) .087(3) .057(2) .082(2) -.003(2) .045(2) .001(2)
C(1A) .042(3) .039(3) .040(2) .003(2) .004(2) -.004(2)
C(2A) .043(3) .047(3) .034(2) .003(3) .000(2) .000(2)
C(3A) .039(3) .052(3) .049(2) .009(3) .005(2) .002(2)
C(4A) .046(3) .046(3) .038(2) .001(3) .008(2) -.008(2)
C(5A) .045(3) .057(3) .039(2) .000(3) -.002(2) .001(2)
C(6A) .036(3) .044(3) .049(2) .002(2) -.002(2) .002(2)
C(7A) .040(3) .048(3) .043(2) .003(3) .005(2) -.001(2)
Cl(1B) .0610(10) .1140(10) .0760(10) -.0280(10) -.0030(10) .0070(10)
Cl(2B) .0950(10) .0930(10) .0680(10) -.0110(10) -.0440(10) -.0040(10)
Cl(3B) .1070(10) .157(2) .0590(10) -.0570(10) .0040(10) .0180(10)
O(1B) .077(3) .061(2) .075(2) .012(2) -.036(2) -.018(2)
O(2B) .144(4) .057(2) .097(3) .024(3) -.075(3) -.012(2)
C(1B) .051(3) .040(3) .045(2) -.003(3) -.010(2) .004(2)
C(2B) .041(3) .052(3) .057(3) -.007(3) -.008(2) .005(2)
C(3B) .063(4) .061(3) .041(2) -.003(3) -.008(2) .007(2)
C(4B) .064(4) .049(3) .049(3) -.002(3) -.022(3) -.002(2)
C(5B) .052(3) .065(4) .064(3) -.017(3) -.014(3) .003(3)
C(6B) .059(3) .057(3) .045(3) -.010(3) -.004(2) .005(2)
C(7B) .057(3) .045(3) .051(3) -.004(3) -.014(3) .000(3)
Cl(1C) .0480(10) .1130(10) .1000(10) -.0200(10) .0010(10) .0260(10)
Cl(2C) .1250(10) .0950(10) .0790(10) -.0170(10) -.0590(10) -.0040(10)
Cl(3C) .0740(10) .0960(10) .0650(10) -.0060(10) .0150(10) .0140(10)
O(1C) .111(4) .061(3) .080(3) .008(3) -.053(2) -.019(2)
O(2C) .107(3) .066(3) .083(3) .017(3) -.054(2) .002(2)
C(1C) .042(3) .044(3) .048(3) .000(3) -.011(2) .006(2)
C(2C) .043(3) .049(3) .058(3) -.005(3) -.004(2) .010(2)
C(3C) .063(4) .061(3) .044(3) .001(3) -.002(2) .003(2)
C(4C) .068(4) .044(3) .054(3) -.001(3) -.024(3) -.002(2)
C(5C) .043(3) .054(3) .076(4) -.009(3) -.015(3) .005(3)
C(6C) .047(3) .046(3) .052(3) -.002(3) -.003(2) .007(2)
C(7C) .056(3) .048(3) .051(3) -.004(3) -.013(2) .000(3)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
Cl(1A) -.0184(2) 1.13210(10) .03210(10) .0710(10)
Cl(2A) -0.1281(2) 1.11470(10) .20620(10) .0640(10)
Cl(3A) .5036(2) .96200(10) .14070(10) .0660(10)
O(1A) .3647(5) .9321(3) .03720(10) .0620(10)
O(2A) .4356(5) 1.1089(3) .03410(10) .0750(10)
C(1A) .2335(6) 1.0497(3) .08950(10) .0400(10)
C(2A) .0612(6) 1.0983(4) .08460(10) .041(2)
C(3A) -.0520(6) 1.1158(4) .11950(10) .046(2)
C(4A) .0111(6) 1.0887(4) .16120(10) .043(2)
C(5A) .1830(6) 1.0414(4) .16830(10) .047(2)
C(6A) .2907(6) 1.0218(4) .13180(10) .043(2)
C(7A) .3536(6) 1.0273(4) .05070(10) .044(2)
Cl(1B) 1.0222(2) .79360(10) .08290(10) .0830(10)
Cl(2B) .4016(2) .64250(10) .00710(10) .0860(10)
Cl(3B) .4849(3) .6259(2) .18290(10) .1080(10)
O(1B) .8394(5) .8320(3) .18460(10) .0710(10)
O(2B) .9506(7) .6643(3) .18750(10) .100(2)
C(1B) .7427(7) .7090(4) .12960(10) .045(2)
C(2B) .8056(6) .7351(4) .0878(2) .050(2)
C(3B) .7039(7) .7134(4) .05020(10) .055(2)
C(4B) .5338(8) .6661(4) .0543(2) .054(2)
C(5B) .4642(7) .6386(4) .0947(2) .060(2)
C(6B) .5699(7) .6600(4) .13170(10) .054(2)
C(7B) .8523(7) .7375(4) .1705(2) .051(2)
Cl(1C) .9523(2) .78300(10) .36160(10) .0870(10)
Cl(2C) 1.5628(3) .94930(10) .43590(10) .1010(10)
Cl(3C) 1.5136(2) .90820(10) .25980(10) .0780(10)
O(1C) 1.1441(6) .7168(3) .26130(10) .085(2)
O(2C) 1.0395(6) .8854(3) .25580(10) .086(2)
C(1C) 1.2434(7) .8449(4) .31460(10) .045(2)
C(2C) 1.1717(7) .8338(4) .3561(2) .050(2)
C(3C) 1.2670(7) .8645(4) .3939(2) .056(2)
C(4C) 1.4395(8) .9083(4) .3890(2) .056(2)
C(5C) 1.5183(7) .9220(4) .3481(2) .058(2)
C(6C) 1.4193(7) .8896(4) .31140(10) .049(2)
C(7C) 1.1339(7) .8134(4) .27420(10) .052(2)
H(1A) .446(5) .921(4) .0122(10) .080
H(3A) -0.1721 1.1475 .1152 .060
H(5A) .2251 1.0231 .1976 .060
H(1B) .930(5) .852(4) .2073(11) .080
H(3B) .7520 .7317 .0217 .060
H(5B) .3450 .6050 .0971 .060
H(1C) 1.068(5) .696(4) .2356(10) .080
H(3C) 1.2146 .8555 .4225 .060
H(5C) 1.6400 .9523 .3454 .060
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C(2A) C(1A) C(6A) . 117.6(4) yes
C(2A) C(1A) C(7A) . 121.7(4) yes
C(6A) C(1A) C(7A) . 120.7(4) yes
Cl(1A) C(2A) C(1A) . 119.2(3) yes
Cl(1A) C(2A) C(3A) . 118.4(3) yes
C(1A) C(2A) C(3A) . 122.3(4) yes
C(2A) C(3A) C(4A) . 118.4(4) yes
Cl(2A) C(4A) C(3A) . 119.0(4) yes
Cl(2A) C(4A) C(5A) . 119.0(3) yes
C(3A) C(4A) C(5A) . 122.0(4) yes
C(4A) C(5A) C(6A) . 117.6(4) yes
Cl(3A) C(6A) C(1A) . 120.4(3) yes
Cl(3A) C(6A) C(5A) . 117.5(3) yes
C(1A) C(6A) C(5A) . 122.1(4) yes
O(1A) C(7A) O(2A) . 125.1(4) yes
O(1A) C(7A) C(1A) . 118.2(4) yes
O(2A) C(7A) C(1A) . 116.7(4) yes
C(2B) C(1B) C(6B) . 116.6(4) yes
C(2B) C(1B) C(7B) . 121.4(4) yes
C(6B) C(1B) C(7B) . 122.0(4) yes
Cl(1B) C(2B) C(1B) . 118.8(4) yes
Cl(1B) C(2B) C(3B) . 119.0(4) yes
C(1B) C(2B) C(3B) . 122.1(4) yes
C(2B) C(3B) C(4B) . 118.8(4) yes
Cl(2B) C(4B) C(3B) . 119.1(4) yes
Cl(2B) C(4B) C(5B) . 119.1(4) yes
C(3B) C(4B) C(5B) . 121.8(5) yes
C(4B) C(5B) C(6B) . 118.2(5) yes
Cl(3B) C(6B) C(1B) . 118.5(3) yes
Cl(3B) C(6B) C(5B) . 118.9(4) yes
C(1B) C(6B) C(5B) . 122.5(4) yes
O(1B) C(7B) O(2B) . 124.9(5) yes
O(1B) C(7B) C(1B) . 117.3(4) yes
O(2B) C(7B) C(1B) . 117.8(4) yes
C(2C) C(1C) C(6C) . 117.6(4) yes
C(2C) C(1C) C(7C) . 121.2(4) yes
C(6C) C(1C) C(7C) . 121.2(4) yes
Cl(1C) C(2C) C(1C) . 119.2(4) yes
Cl(1C) C(2C) C(3C) . 118.1(4) yes
C(1C) C(2C) C(3C) . 122.6(4) yes
C(2C) C(3C) C(4C) . 117.7(4) yes
Cl(2C) C(4C) C(3C) . 119.0(4) yes
Cl(2C) C(4C) C(5C) . 118.8(4) yes
C(3C) C(4C) C(5C) . 122.2(5) yes
C(4C) C(5C) C(6C) . 118.2(5) yes
Cl(3C) C(6C) C(1C) . 119.3(3) yes
Cl(3C) C(6C) C(5C) . 119.0(4) yes
C(1C) C(6C) C(5C) . 121.7(4) yes
O(1C) C(7C) O(2C) . 124.4(5) yes
O(1C) C(7C) C(1C) . 117.8(4) yes
O(2C) C(7C) C(1C) . 117.8(4) yes
O(1A) H(1A) O(2A) 2_675 172(3) no
O(1B) H(1B) O(2C) . 166(3) no
O(1C) H(1C) O(2B) . 176(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(1A) C(2A) . . 1.734(4) yes
Cl(2A) C(4A) . . 1.737(4) yes
Cl(3A) C(6A) . . 1.727(5) yes
O(1A) C(7A) . . 1.234(6) yes
O(2A) C(7A) . . 1.269(6) yes
C(1A) C(2A) . . 1.391(6) yes
C(1A) C(6A) . . 1.381(6) yes
C(1A) C(7A) . . 1.498(6) yes
C(2A) C(3A) . . 1.364(6) yes
C(3A) C(4A) . . 1.377(6) yes
C(4A) C(5A) . . 1.389(6) yes
C(5A) C(6A) . . 1.385(6) yes
Cl(1B) C(2B) . . 1.735(5) yes
Cl(2B) C(4B) . . 1.734(5) yes
Cl(3B) C(6B) . . 1.727(5) yes
O(1B) C(7B) . . 1.233(6) yes
O(2B) C(7B) . . 1.250(6) yes
C(1B) C(2B) . . 1.390(6) yes
C(1B) C(6B) . . 1.392(7) yes
C(1B) C(7B) . . 1.503(6) yes
C(2B) C(3B) . . 1.374(6) yes
C(3B) C(4B) . . 1.370(7) yes
C(4B) C(5B) . . 1.371(7) yes
C(5B) C(6B) . . 1.376(7) yes
Cl(1C) C(2C) . . 1.720(5) yes
Cl(2C) C(4C) . . 1.740(5) yes
Cl(3C) C(6C) . . 1.729(5) yes
O(1C) C(7C) . . 1.244(6) yes
O(2C) C(7C) . . 1.241(6) yes
C(1C) C(2C) . . 1.371(6) yes
C(1C) C(6C) . . 1.393(7) yes
C(1C) C(7C) . . 1.501(6) yes
C(2C) C(3C) . . 1.381(7) yes
C(3C) C(4C) . . 1.371(8) yes
C(4C) C(5C) . . 1.383(7) yes
C(5C) C(6C) . . 1.372(7) yes
Cl(2C) Cl(2B) . 3_665 3.437(2) yes
O(2A) O(1A) 2_675 . 2.664(3) yes
O(2A) H(1A) 2_675 . 1.69(3) yes
Cl(2C) Cl(2B) . 3_665 3.437(2) yes
O(1A) H(1A) . . 0.98(3) no
O(1B) H(1B) . . 0.98(3) no
O(2C) H(1B) . . 1.71(2) no
O(1C) H(1C) . . 0.98(3) no
O(2B) H(1C) . . 1.72(3) no
O(1B) O(2C) . . 2.661(3) no
O(2B) O(1C) . . 2.693(3) no