#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2017232.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_2017232
loop_
_publ_author_name
'Ramos, Ana I.'
'Braga, Susana S.'
'Almeida Paz, Filipe A.'
_publ_section_title
;
 Triclosan
;
_journal_coeditor_code           FG3111
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o404
_journal_page_last               o405
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H7 Cl3 O2'
_chemical_formula_moiety         'C12 H7 Cl3 O2'
_chemical_formula_sum            'C12 H7 Cl3 O2'
_chemical_formula_weight         289.53
_chemical_name_common            Triclosan
_chemical_name_systematic
;
5-chloro-2-(2,4-dichlorophenoxy)phenol
;
_space_group_IT_number           144
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   12.52250(10)
_cell_length_b                   12.52250(10)
_cell_length_c                   6.68090(10)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.55
_cell_measurement_theta_min      3.25
_cell_volume                     907.293(17)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2005)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII X8 KappaCCD'
_diffrn_measurement_method       \w/\f
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            35385
_diffrn_reflns_theta_full        36.31
_diffrn_reflns_theta_max         36.31
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.9569
_exptl_absorpt_correction_T_min  0.8539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.276
_refine_ls_abs_structure_details
'Flack (1983), with 2729 estimated Friedel pairs'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         5670
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0374
_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/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0698
_reflns_number_gt                4382
_reflns_number_total             5670
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    fg3111.cif
_[local]_cod_data_source_block   I
_cod_database_code               2017232
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
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
C C1 0.13930(12) 0.20835(12) 0.8248(2) 0.0142(2) Uani d . 1
C C2 0.21766(13) 0.27043(13) 0.6665(2) 0.0169(3) Uani d . 1
C C3 0.28032(14) 0.39805(14) 0.6578(2) 0.0237(3) Uani d . 1
H H3 0.3315 0.4393 0.5462 0.028 Uiso calc R 1
C C4 0.26835(15) 0.46577(14) 0.8121(2) 0.0252(3) Uani d . 1
H H4 0.3104 0.5533 0.8071 0.030 Uiso calc R 1
C C5 0.19371(13) 0.40282(13) 0.9731(2) 0.0197(3) Uani d . 1
C C6 0.12885(13) 0.27524(13) 0.9825(2) 0.0171(3) Uani d . 1
H H6 0.0781 0.2341 1.0945 0.021 Uiso calc R 1
O O1 0.07514(9) 0.08182(9) 0.81936(14) 0.01613(19) Uani d . 1
H H1 0.0217 0.0549 0.9103 0.024 Uiso calc R 1
Cl Cl5 0.18177(4) 0.48547(4) 1.17285(6) 0.03084(10) Uani d . 1
O O1' 0.22597(9) 0.20292(9) 0.50694(14) 0.0185(2) Uani d . 1
C C1' 0.31738(12) 0.17225(12) 0.5162(2) 0.0164(2) Uani d . 1
C C2' 0.32767(13) 0.10907(13) 0.3522(2) 0.0163(3) Uani d . 1
C C3' 0.41482(14) 0.07173(14) 0.3475(2) 0.0200(3) Uani d . 1
H H3' 0.4211 0.0287 0.2351 0.024 Uiso calc R 1
C C4' 0.49253(13) 0.09872(15) 0.5104(2) 0.0228(3) Uani d . 1
C C5' 0.48531(14) 0.16287(16) 0.6735(2) 0.0246(3) Uani d . 1
H H5' 0.5404 0.1821 0.7830 0.030 Uiso calc R 1
C C6' 0.39716(13) 0.19884(14) 0.6762(2) 0.0222(3) Uani d . 1
H H6' 0.3914 0.2421 0.7886 0.027 Uiso calc R 1
Cl Cl2' 0.23162(3) 0.07755(3) 0.14807(5) 0.01930(7) Uani d . 1
Cl Cl4' 0.60016(4) 0.04946(4) 0.50482(6) 0.03456(11) Uani d . 1
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
C1 0.0142(6) 0.0150(6) 0.0146(6) 0.0081(5) -0.0018(5) -0.0001(5)
C2 0.0174(6) 0.0190(6) 0.0150(6) 0.0097(5) 0.0000(5) -0.0010(5)
C3 0.0231(7) 0.0203(7) 0.0225(8) 0.0069(6) 0.0045(6) 0.0020(6)
C4 0.0295(8) 0.0149(6) 0.0268(8) 0.0080(6) 0.0000(6) -0.0005(6)
C5 0.0238(7) 0.0200(7) 0.0185(7) 0.0135(6) -0.0029(5) -0.0045(5)
C6 0.0182(6) 0.0201(6) 0.0149(6) 0.0111(5) 0.0015(5) 0.0001(5)
Cl5 0.0411(2) 0.02597(19) 0.0295(2) 0.01984(17) 0.00034(17) -0.00977(16)
O1 0.0175(5) 0.0146(4) 0.0147(5) 0.0068(4) 0.0015(3) 0.0001(4)
O1' 0.0184(5) 0.0238(5) 0.0146(5) 0.0117(4) 0.0011(4) -0.0027(4)
C1' 0.0151(6) 0.0163(6) 0.0162(6) 0.0068(5) 0.0021(5) 0.0017(5)
C2' 0.0164(6) 0.0180(6) 0.0127(6) 0.0072(5) -0.0005(5) 0.0005(5)
C3' 0.0231(7) 0.0228(7) 0.0161(7) 0.0130(6) 0.0012(5) -0.0002(5)
C4' 0.0207(7) 0.0290(8) 0.0232(7) 0.0159(6) -0.0009(6) 0.0007(6)
C5' 0.0227(7) 0.0336(8) 0.0177(7) 0.0141(7) -0.0047(6) -0.0015(6)
C6' 0.0233(7) 0.0251(7) 0.0161(7) 0.0104(6) -0.0007(5) -0.0030(6)
Cl2' 0.02057(15) 0.02406(17) 0.01361(14) 0.01141(14) -0.00251(12) -0.00153(12)
Cl4' 0.0334(2) 0.0527(3) 0.0324(2) 0.0326(2) -0.00715(17) -0.00585(19)
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'
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' O1' C2 117.26(10) no
C1 O1 H1 109.5 no
C3' C2' C1' 121.42(13) no
C3' C2' Cl2' 118.69(11) no
C1' C2' Cl2' 119.88(10) no
C4' C3' C2' 118.38(13) no
C4' C3' H3' 120.8 no
C2' C3' H3' 120.8 no
C5' C4' C3' 121.27(14) no
C5' C4' Cl4' 120.65(12) no
C3' C4' Cl4' 118.08(12) no
C4' C5' C6' 119.53(14) no
C4' C5' H5' 120.2 no
C6' C5' H5' 120.2 no
C1' C6' C5' 120.55(14) no
C1' C6' H6' 119.7 no
C5' C6' H6' 119.7 no
O1' C1' C6' 124.54(12) no
O1' C1' C2' 116.62(12) no
C6' C1' C2' 118.84(12) no
O1 C1 C2 117.92(11) no
O1 C1 C6 122.55(12) no
C2 C1 C6 119.53(12) no
C3 C2 C1 120.82(13) no
C3 C2 O1' 119.73(13) no
C1 C2 O1' 119.28(12) no
C2 C3 C4 120.08(14) no
C2 C3 H3 120.0 no
C4 C3 H3 120.0 no
C5 C4 C3 118.50(13) no
C5 C4 H4 120.7 no
C3 C4 H4 120.7 no
C4 C5 C6 122.12(13) no
C4 C5 Cl5 119.45(11) no
C6 C5 Cl5 118.43(11) no
C5 C6 C1 118.86(13) no
C5 C6 H6 120.6 no
C1 C6 H6 120.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl2' C2' 1.7287(14) no
Cl4' C4' 1.7407(15) no
Cl5 C5 1.7405(15) no
O1' C1' 1.3789(17) no
O1' C2 1.3961(17) no
O1 C1 1.3727(16) no
O1 H1 0.8400 no
C2' C3' 1.386(2) no
C2' C1' 1.3943(19) no
C3' C4' 1.385(2) no
C3' H3' 0.9500 no
C4' C5' 1.383(2) no
C5' C6' 1.385(2) no
C5' H5' 0.9500 no
C6' C1' 1.385(2) no
C6' H6' 0.9500 no
C1 C2 1.387(2) no
C1 C6 1.392(2) no
C2 C3 1.385(2) no
C3 C4 1.390(2) no
C3 H3 0.9500 no
C4 C5 1.384(2) no
C4 H4 0.9500 no
C5 C6 1.385(2) no
C6 H6 0.9500 no
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
O1 H1 O1 2 0.84 1.97 2.8058(10) 171
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
_geom_torsion_publ_flag
C1' C2' C3' C4' 0.0(2) no
Cl2' C2' C3' C4' 179.16(11) no
C2' C3' C4' C5' -0.9(2) no
C2' C3' C4' Cl4' 179.05(11) no
C3' C4' C5' C6' 1.3(2) no
Cl4' C4' C5' C6' -178.67(12) no
C4' C5' C6' C1' -0.7(2) no
C2 O1' C1' C6' 3.11(19) no
C2 O1' C1' C2' -177.55(12) no
C5' C6' C1' O1' 179.10(13) no
C5' C6' C1' C2' -0.2(2) no
C3' C2' C1' O1' -178.78(13) no
Cl2' C2' C1' O1' 2.03(17) no
C3' C2' C1' C6' 0.6(2) no
Cl2' C2' C1' C6' -178.59(11) no
O1 C1 C2 C3 176.72(13) no
C6 C1 C2 C3 -3.6(2) no
O1 C1 C2 O1' 1.58(18) no
C6 C1 C2 O1' -178.77(12) no
C1' O1' C2 C3 91.92(15) no
C1' O1' C2 C1 -92.88(15) no
C1 C2 C3 C4 2.1(2) no
O1' C2 C3 C4 177.26(14) no
C2 C3 C4 C5 0.4(2) no
C3 C4 C5 C6 -1.6(2) no
C3 C4 C5 Cl5 177.53(12) no
C4 C5 C6 C1 0.1(2) no
Cl5 C5 C6 C1 -179.02(11) no
O1 C1 C6 C5 -177.86(12) no
C2 C1 C6 C5 2.50(19) no