#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/89/2218953.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_2218953
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Babitha, K. S.'
'Fuess, Hartmut'
_publ_section_title
;
 4-Chlorophenyl 4-chlorobenzoate
;
_journal_coeditor_code           CI2640
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1582
_journal_paper_doi               10.1107/S1600536808022800
_journal_volume                  64
_journal_year                    2008
_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
;
4-Chlorophenyl 4-chlorobenzoate
;
_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_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.804(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.370(2)
_cell_length_b                   3.9528(4)
_cell_length_c                   19.465(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      24.25
_cell_measurement_theta_min      11.47
_cell_volume                     1182.0(2)
_computing_cell_refinement       'CAD-4-PC (Enraf--Nonius, 1996)'
_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 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(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  0.0799
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4211
_diffrn_reflns_theta_full        66.97
_diffrn_reflns_theta_max         66.97
_diffrn_reflns_theta_min         3.61
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.826
_exptl_absorpt_correction_T_max  0.4198
_exptl_absorpt_correction_T_min  0.1936
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.328
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0736P)²+0.2805P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1389
_reflns_number_gt                1724
_reflns_number_total             2109
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2640.cif
_cod_data_source_block           I
_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_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218953
_cod_database_fobs_code          2218953
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_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_occupancy
Cl Cl1 0.49228(5) 0.7640(2) 0.08027(4) 0.0690(3) Uani d 1
Cl Cl2 0.72347(5) -0.0839(2) 0.67678(3) 0.0704(3) Uani d 1
O O1 0.59363(10) 0.3353(5) 0.36024(9) 0.0529(5) Uani d 1
O O2 0.72448(12) 0.5904(7) 0.36130(10) 0.0737(7) Uani d 1
C C1 0.57335(13) 0.4453(6) 0.29332(12) 0.0444(5) Uani d 1
C C2 0.49523(15) 0.6088(7) 0.28247(14) 0.0518(6) Uani d 1
H H2 0.4603(19) 0.657(8) 0.3193(16) 0.062 Uiso d 1
C C3 0.46945(15) 0.7062(7) 0.21667(15) 0.0546(6) Uani d 1
H H3 0.4132(19) 0.820(9) 0.2133(15) 0.066 Uiso d 1
C C4 0.52292(14) 0.6377(6) 0.16294(13) 0.0469(5) Uani d 1
C C5 0.60108(15) 0.4709(7) 0.17399(13) 0.0492(6) Uani d 1
H H5 0.6337(18) 0.438(8) 0.1358(16) 0.059 Uiso d 1
C C6 0.62658(14) 0.3724(7) 0.23892(13) 0.0488(6) Uani d 1
H H6 0.6762(19) 0.246(8) 0.2482(15) 0.059 Uiso d 1
C C7 0.67225(14) 0.4158(7) 0.38938(12) 0.0482(6) Uani d 1
C C8 0.68345(13) 0.2812(6) 0.45961(12) 0.0452(5) Uani d 1
C C9 0.61746(15) 0.1152(8) 0.49299(14) 0.0530(6) Uani d 1
H H9 0.5619(19) 0.089(8) 0.4691(16) 0.064 Uiso d 1
C C10 0.62957(16) 0.0048(8) 0.55961(13) 0.0538(6) Uani d 1
H H10 0.584(2) -0.108(8) 0.5807(16) 0.065 Uiso d 1
C C11 0.70901(15) 0.0570(7) 0.59276(13) 0.0494(6) Uani d 1
C C12 0.77573(16) 0.2151(8) 0.56050(15) 0.0579(7) Uani d 1
H H12 0.826(2) 0.225(9) 0.5856(17) 0.069 Uiso d 1
C C13 0.76306(14) 0.3276(8) 0.49402(14) 0.0534(6) Uani d 1
H H13 0.8067(19) 0.428(9) 0.4718(16) 0.064 Uiso 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
Cl1 0.0694(4) 0.0793(5) 0.0574(4) 0.0037(3) -0.0138(3) 0.0097(4)
Cl2 0.0777(5) 0.0819(6) 0.0507(4) 0.0114(4) -0.0142(3) 0.0012(3)
O1 0.0419(8) 0.0685(12) 0.0480(9) -0.0142(8) -0.0015(6) 0.0071(9)
O2 0.0623(11) 0.0998(18) 0.0589(11) -0.0387(11) 0.0032(9) 0.0064(11)
C1 0.0394(10) 0.0469(13) 0.0469(12) -0.0087(9) 0.0002(9) -0.0007(11)
C2 0.0404(11) 0.0604(16) 0.0553(14) -0.0009(10) 0.0094(10) -0.0063(12)
C3 0.0395(11) 0.0581(15) 0.0659(16) 0.0061(11) -0.0023(10) -0.0024(13)
C4 0.0447(11) 0.0462(13) 0.0492(12) -0.0044(10) -0.0046(9) 0.0006(11)
C5 0.0451(11) 0.0537(14) 0.0491(13) 0.0034(10) 0.0054(10) -0.0044(12)
C6 0.0393(11) 0.0553(14) 0.0518(13) 0.0056(10) 0.0007(9) -0.0009(12)
C7 0.0378(10) 0.0605(15) 0.0463(12) -0.0070(10) 0.0038(9) -0.0042(11)
C8 0.0367(10) 0.0513(13) 0.0477(13) -0.0032(9) 0.0027(9) -0.0065(11)
C9 0.0368(10) 0.0715(17) 0.0504(13) -0.0101(11) -0.0043(9) 0.0033(12)
C10 0.0428(11) 0.0678(16) 0.0507(13) -0.0070(12) 0.0003(10) 0.0049(13)
C11 0.0514(12) 0.0502(14) 0.0460(12) 0.0065(10) -0.0064(10) -0.0059(11)
C12 0.0413(11) 0.0657(17) 0.0659(16) 0.0002(11) -0.0123(11) -0.0106(14)
C13 0.0356(10) 0.0625(16) 0.0622(15) -0.0079(11) 0.0026(10) -0.0057(13)
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'
Cl Cl 0.3639 0.7018 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O1 C1 119.07(17)
C2 C1 C6 120.9(2)
C2 C1 O1 117.2(2)
C6 C1 O1 121.7(2)
C1 C2 C3 119.8(2)
C1 C2 H2 120.1(19)
C3 C2 H2 120.1(19)
C4 C3 C2 119.2(2)
C4 C3 H3 126.1(17)
C2 C3 H3 114.7(17)
C3 C4 C5 120.8(2)
C3 C4 Cl1 119.77(19)
C5 C4 Cl1 119.41(19)
C6 C5 C4 120.1(2)
C6 C5 H5 124.0(19)
C4 C5 H5 115.8(19)
C5 C6 C1 119.1(2)
C5 C6 H6 123.0(18)
C1 C6 H6 117.8(18)
O2 C7 O1 122.9(2)
O2 C7 C8 124.7(2)
O1 C7 C8 112.34(19)
C9 C8 C13 118.9(2)
C9 C8 C7 122.7(2)
C13 C8 C7 118.4(2)
C10 C9 C8 120.8(2)
C10 C9 H9 120.8(18)
C8 C9 H9 118.3(18)
C11 C10 C9 119.0(2)
C11 C10 H10 122(2)
C9 C10 H10 119(2)
C12 C11 C10 121.2(2)
C12 C11 Cl2 120.19(19)
C10 C11 Cl2 118.6(2)
C11 C12 C13 119.5(2)
C11 C12 H12 114(2)
C13 C12 H12 126(2)
C12 C13 C8 120.5(2)
C12 C13 H13 121(2)
C8 C13 H13 119(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.736(3)
Cl2 C11 1.735(3)
O1 C7 1.356(3)
O1 C1 1.399(3)
O2 C7 1.203(3)
C1 C2 1.374(3)
C1 C6 1.389(3)
C2 C3 1.383(4)
C2 H2 0.93(3)
C3 C4 1.377(4)
C3 H3 0.97(3)
C4 C5 1.381(3)
C5 C6 1.368(4)
C5 H5 0.92(3)
C6 H6 0.93(3)
C7 C8 1.472(3)
C8 C9 1.387(3)
C8 C13 1.389(3)
C9 C10 1.375(4)
C9 H9 0.96(3)
C10 C11 1.379(3)
C10 H10 0.93(3)
C11 C12 1.370(4)
C12 C13 1.376(4)
C12 H12 0.90(3)
C13 H13 0.90(3)
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
C5 H5 O2 2_645 0.92(3) 2.58(3) 3.168(3) 123(2)
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
C7 O1 C1 C2 -129.5(3)
C7 O1 C1 C6 55.0(3)
C6 C1 C2 C3 -0.8(4)
O1 C1 C2 C3 -176.3(2)
C1 C2 C3 C4 -0.1(4)
C2 C3 C4 C5 0.7(4)
C2 C3 C4 Cl1 -179.0(2)
C3 C4 C5 C6 -0.3(4)
Cl1 C4 C5 C6 179.4(2)
C4 C5 C6 C1 -0.6(4)
C2 C1 C6 C5 1.1(4)
O1 C1 C6 C5 176.5(2)
C1 O1 C7 O2 3.2(4)
C1 O1 C7 C8 -179.9(2)
O2 C7 C8 C9 172.1(3)
O1 C7 C8 C9 -4.8(4)
O2 C7 C8 C13 -6.9(4)
O1 C7 C8 C13 176.2(2)
C13 C8 C9 C10 1.5(4)
C7 C8 C9 C10 -177.5(3)
C8 C9 C10 C11 -0.9(4)
C9 C10 C11 C12 -0.2(4)
C9 C10 C11 Cl2 -179.9(2)
C10 C11 C12 C13 0.7(4)
Cl2 C11 C12 C13 -179.5(2)
C11 C12 C13 C8 -0.1(4)
C9 C8 C13 C12 -1.0(4)
C7 C8 C13 C12 178.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 216946
