#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/11/4501141.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_4501141
loop_
_publ_author_name
'Mukherjee, Arijit'
'Desiraju, Gautam R.'
_publ_section_title
;
 Halogen Bonding and Structural Modularity in 2,3,4- and
 3,4,5-Trichlorophenol
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3735
_journal_paper_doi               10.1021/cg2007815
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C6 H3 Cl3 O'
_chemical_formula_weight         197.43
_chemical_name_common            2,3,4-Trichlorophenol
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.902(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8010(6)
_cell_length_b                   12.7973(17)
_cell_length_c                   14.816(3)
_cell_measurement_reflns_used    1914
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.6
_cell_volume                     715.5(2)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_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  0.0812
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7381
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    1.195
_exptl_absorpt_correction_T_max  0.9427
_exptl_absorpt_correction_T_min  0.5864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0458P)²+0.3327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                1517
_reflns_number_total             1636
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg2007815_si_007.cif
_cod_data_source_block           datam
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_sg_symbol_H-M      'P 21/n'
_cod_database_code               4501141
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.17950(14) 0.78498(4) 0.15870(4) 0.02312(17) Uani 1 1 d .
Cl2 Cl 0.32716(15) 0.82719(4) 0.36907(4) 0.02367(17) Uani 1 1 d .
Cl3 Cl -0.19900(15) 0.57466(4) 0.08989(4) 0.02736(18) Uani 1 1 d .
O1 O 0.0914(5) 0.65481(13) 0.48187(11) 0.0317(4) Uani 1 1 d .
H1 H 0.2310 0.7053 0.4930 0.048 Uiso 1 1 calc R
C6 C -0.1035(6) 0.60038(16) 0.20514(14) 0.0187(4) Uani 1 1 d .
C4 C -0.1272(6) 0.54630(16) 0.35981(15) 0.0226(5) Uani 1 1 d .
H4 H -0.1915 0.4959 0.4020 0.027 Uiso 1 1 calc R
C2 C 0.1266(5) 0.71244(15) 0.32796(14) 0.0182(4) Uani 1 1 d .
C1 C 0.0600(5) 0.69364(15) 0.23516(14) 0.0175(4) Uani 1 1 d .
C3 C 0.0343(6) 0.63879(16) 0.39087(14) 0.0204(4) Uani 1 1 d .
C5 C -0.1945(6) 0.52732(15) 0.26769(16) 0.0210(4) Uani 1 1 d .
H5 H -0.3041 0.4636 0.2468 0.025 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0284(3) 0.0205(3) 0.0212(3) 0.00595(17) 0.0062(2) -0.00027(18)
Cl2 0.0283(3) 0.0177(3) 0.0248(3) -0.00316(18) 0.0022(2) -0.00325(18)
Cl3 0.0355(3) 0.0272(3) 0.0188(3) -0.00407(19) 0.0008(2) -0.0002(2)
O1 0.0501(11) 0.0292(9) 0.0152(8) 0.0007(6) 0.0019(7) -0.0078(8)
C6 0.0203(10) 0.0191(10) 0.0166(10) -0.0017(7) 0.0014(8) 0.0038(8)
C4 0.0266(11) 0.0174(10) 0.0245(11) 0.0044(8) 0.0051(9) 0.0005(8)
C2 0.0182(10) 0.0149(9) 0.0212(11) -0.0001(7) 0.0019(8) 0.0001(7)
C1 0.0179(10) 0.0150(9) 0.0200(10) 0.0030(7) 0.0037(8) 0.0029(7)
C3 0.0239(11) 0.0198(10) 0.0177(10) 0.0009(7) 0.0030(8) 0.0029(8)
C5 0.0224(10) 0.0148(9) 0.0259(11) -0.0007(8) 0.0037(8) -0.0008(8)
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
C3 O1 H1 109.5
C5 C6 C1 120.0(2)
C5 C6 Cl3 119.33(16)
C1 C6 Cl3 120.62(16)
C5 C4 C3 120.06(19)
C5 C4 H4 120.0
C3 C4 H4 120.0
C1 C2 C3 120.81(19)
C1 C2 Cl2 121.03(16)
C3 C2 Cl2 118.16(16)
C2 C1 C6 119.05(19)
C2 C1 Cl1 120.09(16)
C6 C1 Cl1 120.86(16)
O1 C3 C4 118.11(19)
O1 C3 C2 122.53(19)
C4 C3 C2 119.4(2)
C4 C5 C6 120.67(19)
C4 C5 H5 119.7
C6 C5 H5 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.726(2)
Cl2 C2 1.731(2)
Cl3 C6 1.734(2)
O1 C3 1.355(3)
O1 H1 0.8400
C6 C5 1.389(3)
C6 C1 1.394(3)
C4 C5 1.380(3)
C4 C3 1.386(3)
C4 H4 0.9500
C2 C1 1.389(3)
C2 C3 1.400(3)
C5 H5 0.9500
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
C3 C2 C1 C6 0.5(3)
Cl2 C2 C1 C6 -179.69(15)
C3 C2 C1 Cl1 -179.44(16)
Cl2 C2 C1 Cl1 0.4(3)
C5 C6 C1 C2 -0.6(3)
Cl3 C6 C1 C2 178.84(16)
C5 C6 C1 Cl1 179.33(16)
Cl3 C6 C1 Cl1 -1.2(2)
C5 C4 C3 O1 179.2(2)
C5 C4 C3 C2 0.2(3)
C1 C2 C3 O1 -179.2(2)
Cl2 C2 C3 O1 1.0(3)
C1 C2 C3 C4 -0.3(3)
Cl2 C2 C3 C4 179.90(16)
C3 C4 C5 C6 -0.3(3)
C1 C6 C5 C4 0.5(3)
Cl3 C6 C5 C4 -178.94(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25672
2 PubChem 27582
