#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/50/2215022.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_2215022
loop_
_publ_author_name
'B. Thimme Gowda'
'Sabine Foro'
'K. S. Babitha'
'Hartmut Fuess'
_publ_section_title
;
 3,4-Dichlorophenyl benzoate
;
_journal_coeditor_code           BT2472
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3801
_journal_page_last               o3801
_journal_paper_doi               10.1107/S1600536807039396
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H8 Cl2 O2'
_chemical_formula_moiety         'C13 H8 Cl2 O2'
_chemical_formula_sum            'C13 H8 Cl2 O2'
_chemical_formula_weight         267.09
_chemical_name_systematic
;
3,4-Dichlorophenyl benzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 94.200(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1145(7)
_cell_length_b                   13.161(2)
_cell_length_c                   14.696(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.42
_cell_measurement_theta_min      3.35
_cell_volume                     1179.5(3)
_computing_cell_refinement       CAD-4-PC
_computing_data_collection       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4317
_diffrn_reflns_theta_full        66.89
_diffrn_reflns_theta_max         66.89
_diffrn_reflns_theta_min         4.52
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.837
_exptl_absorpt_correction_T_max  0.4227
_exptl_absorpt_correction_T_min  0.3498
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.421
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0717P)²+0.1729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                1769
_reflns_number_total             2100
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2472.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215022
_cod_database_fobs_code          2215022
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.3955(3) 0.57105(15) 0.38247(13) 0.0408(4) Uani d . 1
C C2 0.2631(3) 0.49899(15) 0.41736(13) 0.0439(4) Uani d . 1
H H2 0.1384 0.5182 0.4457 0.053 Uiso calc R 1
C C3 0.3165(3) 0.39790(15) 0.40998(13) 0.0428(4) Uani d . 1
C C4 0.5025(3) 0.36930(15) 0.36829(13) 0.0443(4) Uani d . 1
C C5 0.6353(3) 0.44300(17) 0.33486(14) 0.0486(5) Uani d . 1
H H5 0.7617 0.4241 0.3076 0.058 Uiso calc R 1
C C6 0.5829(3) 0.54449(17) 0.34145(13) 0.0466(5) Uani d . 1
H H6 0.6723 0.5941 0.3186 0.056 Uiso calc R 1
C C7 0.1607(3) 0.71002(15) 0.35000(12) 0.0408(4) Uani d . 1
C C8 0.1318(3) 0.82035(15) 0.36432(12) 0.0414(4) Uani d . 1
C C9 0.2958(4) 0.88165(16) 0.40366(15) 0.0535(5) Uani d . 1
H H9 0.4290 0.8537 0.4257 0.064 Uiso calc R 1
C C10 0.2597(5) 0.98542(18) 0.40998(17) 0.0675(7) Uani d . 1
H H10 0.3699 1.0273 0.4358 0.081 Uiso calc R 1
C C11 0.0625(5) 1.02650(18) 0.37843(17) 0.0688(7) Uani d . 1
H H11 0.0392 1.0961 0.3833 0.083 Uiso calc R 1
C C12 -0.1004(4) 0.96541(19) 0.33972(17) 0.0650(6) Uani d . 1
H H12 -0.2336 0.9938 0.3182 0.078 Uiso calc R 1
C C13 -0.0678(4) 0.86248(17) 0.33260(15) 0.0532(5) Uani d . 1
H H13 -0.1789 0.8212 0.3066 0.064 Uiso calc R 1
O O1 0.3519(2) 0.67433(10) 0.39223(10) 0.0479(4) Uani d . 1
O O2 0.0353(2) 0.65649(12) 0.30619(11) 0.0571(4) Uani d . 1
Cl Cl1 0.14815(11) 0.30812(4) 0.45478(5) 0.0679(2) Uani d . 1
Cl Cl2 0.56926(11) 0.24258(4) 0.35640(5) 0.0687(2) Uani d . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C2 C1 C6 121.40(19)
C2 C1 O1 120.86(17)
C6 C1 O1 117.63(17)
C1 C2 C3 119.29(18)
C1 C2 H2 120.4
C3 C2 H2 120.4
C2 C3 C4 120.38(18)
C2 C3 Cl1 118.64(15)
C4 C3 Cl1 120.97(16)
C5 C4 C3 119.43(19)
C5 C4 Cl2 119.55(16)
C3 C4 Cl2 121.01(16)
C4 C5 C6 120.70(19)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 118.80(19)
C1 C6 H6 120.6
C5 C6 H6 120.6
O2 C7 O1 122.42(18)
O2 C7 C8 125.26(18)
O1 C7 C8 112.32(15)
C9 C8 C13 120.0(2)
C9 C8 C7 122.87(19)
C13 C8 C7 117.05(18)
C8 C9 C10 119.3(2)
C8 C9 H9 120.4
C10 C9 H9 120.4
C11 C10 C9 120.4(2)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C12 120.2(2)
C10 C11 H11 119.9
C12 C11 H11 119.9
C11 C12 C13 120.3(2)
C11 C12 H12 119.8
C13 C12 H12 119.8
C12 C13 C8 119.8(2)
C12 C13 H13 120.1
C8 C13 H13 120.1
C7 O1 C1 116.90(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.371(3)
C1 C6 1.378(3)
C1 O1 1.395(2)
C2 C3 1.376(3)
C2 H2 0.9300
C3 C4 1.383(3)
C3 Cl1 1.7288(19)
C4 C5 1.379(3)
C4 Cl2 1.729(2)
C5 C6 1.379(3)
C5 H5 0.9300
C6 H6 0.9300
C7 O2 1.194(2)
C7 O1 1.366(2)
C7 C8 1.480(3)
C8 C9 1.380(3)
C8 C13 1.390(3)
C9 C10 1.388(3)
C9 H9 0.9300
C10 C11 1.371(4)
C10 H10 0.9300
C11 C12 1.371(4)
C11 H11 0.9300
C12 C13 1.374(3)
C12 H12 0.9300
C13 H13 0.9300
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
C6 C1 C2 C3 -1.0(3)
O1 C1 C2 C3 -177.17(17)
C1 C2 C3 C4 0.4(3)
C1 C2 C3 Cl1 179.74(14)
C2 C3 C4 C5 0.6(3)
Cl1 C3 C4 C5 -178.77(15)
C2 C3 C4 Cl2 -178.71(15)
Cl1 C3 C4 Cl2 1.9(2)
C3 C4 C5 C6 -0.9(3)
Cl2 C4 C5 C6 178.39(16)
C2 C1 C6 C5 0.7(3)
O1 C1 C6 C5 176.96(17)
C4 C5 C6 C1 0.3(3)
O2 C7 C8 C9 -169.9(2)
O1 C7 C8 C9 9.4(3)
O2 C7 C8 C13 7.4(3)
O1 C7 C8 C13 -173.30(17)
C13 C8 C9 C10 -0.8(3)
C7 C8 C9 C10 176.4(2)
C8 C9 C10 C11 0.7(4)
C9 C10 C11 C12 -0.5(4)
C10 C11 C12 C13 0.3(4)
C11 C12 C13 C8 -0.4(4)
C9 C8 C13 C12 0.7(3)
C7 C8 C13 C12 -176.7(2)
O2 C7 O1 C1 -0.3(3)
C8 C7 O1 C1 -179.62(16)
C2 C1 O1 C7 -64.2(2)
C6 C1 O1 C7 119.56(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123643
2 PubChem 13284265
