#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/82/2218212.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_2218212
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Babitha, K. S.'
'Fuess, Hartmut'
_publ_section_title
;
 2,6-Dichlorophenyl 4-methylbenzoate
;
_journal_coeditor_code           OM2223
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o843
_journal_paper_doi               10.1107/S1600536808009616
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H10 Cl2 O2'
_chemical_formula_moiety         'C14 H10 Cl2 O2'
_chemical_formula_sum            'C14 H10 Cl2 O2'
_chemical_formula_weight         281.12
_chemical_name_systematic
;
2,6-Dichlorophenyl 4-methylbenzoate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.898(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5688(8)
_cell_length_b                   11.1370(9)
_cell_length_c                   13.1947(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      18.72
_cell_measurement_theta_min      5.32
_cell_volume                     1330.33(19)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3035
_diffrn_reflns_theta_full        66.95
_diffrn_reflns_theta_max         66.95
_diffrn_reflns_theta_min         5.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.316
_exptl_absorpt_correction_T_max  0.2731
_exptl_absorpt_correction_T_min  0.2020
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.434
_refine_ls_extinction_coef       0.0170(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1211P)²+0.3061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1681
_reflns_number_gt                2025
_reflns_number_total             2366
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2223.cif
_cod_data_source_block           I
_cod_original_cell_volume        1330.33(18)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218212
_cod_database_fobs_code          2218212
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_refinement_flags
_atom_site_occupancy
C C1 0.1987(2) 0.6943(2) 0.02446(17) 0.0490(5) Uani d . 1
C C2 0.1627(3) 0.5987(2) -0.0454(2) 0.0568(6) Uani d . 1
C C3 0.0175(3) 0.5780(3) -0.1077(2) 0.0683(7) Uani d . 1
H H3 -0.0065 0.5127 -0.1541 0.082 Uiso calc R 1
C C4 -0.0902(3) 0.6551(3) -0.0999(2) 0.0705(7) Uani d . 1
H H4 -0.1879 0.6418 -0.1415 0.085 Uiso calc R 1
C C5 -0.0563(3) 0.7510(3) -0.0320(2) 0.0679(7) Uani d . 1
H H5 -0.1304 0.8030 -0.0280 0.082 Uiso calc R 1
C C6 0.0887(3) 0.7707(2) 0.03086(19) 0.0547(6) Uani d . 1
C C7 0.4023(2) 0.6546(2) 0.17553(18) 0.0499(5) Uani d . 1
C C8 0.5626(2) 0.6726(2) 0.22269(17) 0.0484(5) Uani d . 1
C C9 0.6386(3) 0.7563(2) 0.1830(2) 0.0636(7) Uani d . 1
H H9 0.5881 0.8063 0.1266 0.076 Uiso calc R 1
C C10 0.7903(3) 0.7648(3) 0.2280(3) 0.0744(8) Uani d . 1
H H10 0.8409 0.8210 0.2009 0.089 Uiso calc R 1
C C11 0.8687(3) 0.6923(3) 0.3118(2) 0.0693(8) Uani d . 1
C C12 0.7918(3) 0.6113(3) 0.3517(2) 0.0681(7) Uani d . 1
H H12 0.8426 0.5620 0.4086 0.082 Uiso calc R 1
C C13 0.6393(3) 0.6016(2) 0.3082(2) 0.0574(6) Uani d . 1
H H13 0.5887 0.5471 0.3369 0.069 Uiso calc R 1
C C14 1.0350(3) 0.7024(4) 0.3581(3) 0.1081(14) Uani d . 1
H H14A 1.0606 0.7552 0.4189 0.130 Uiso calc R 1
H H14B 1.0733 0.7342 0.3047 0.130 Uiso calc R 1
H H14C 1.0766 0.6245 0.3799 0.130 Uiso calc R 1
O O1 0.34465(16) 0.71769(15) 0.08263(13) 0.0551(5) Uani d . 1
O O2 0.32703(19) 0.59229(19) 0.21108(15) 0.0692(6) Uani d . 1
Cl Cl1 0.30058(9) 0.50474(7) -0.05432(7) 0.0849(4) Uani d . 1
Cl Cl2 0.13347(8) 0.89253(7) 0.11604(6) 0.0796(3) 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
C6 C1 C2 119.2(2)
C6 C1 O1 120.3(2)
C2 C1 O1 120.4(2)
C1 C2 C3 120.8(2)
C1 C2 Cl1 119.07(19)
C3 C2 Cl1 120.2(2)
C4 C3 C2 119.0(3)
C4 C3 H3 120.5
C2 C3 H3 120.5
C5 C4 C3 121.0(2)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 C6 119.7(2)
C4 C5 H5 120.1
C6 C5 H5 120.1
C1 C6 C5 120.2(2)
C1 C6 Cl2 119.48(19)
C5 C6 Cl2 120.26(19)
O2 C7 O1 122.0(2)
O2 C7 C8 126.1(2)
O1 C7 C8 111.85(18)
C13 C8 C9 119.3(2)
C13 C8 C7 118.3(2)
C9 C8 C7 122.4(2)
C10 C9 C8 119.4(3)
C10 C9 H9 120.3
C8 C9 H9 120.3
C11 C10 C9 121.8(3)
C11 C10 H10 119.1
C9 C10 H10 119.1
C12 C11 C10 118.2(2)
C12 C11 C14 121.3(3)
C10 C11 C14 120.5(3)
C11 C12 C13 121.0(3)
C11 C12 H12 119.5
C13 C12 H12 119.5
C8 C13 C12 120.2(2)
C8 C13 H13 119.9
C12 C13 H13 119.9
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C7 O1 C1 116.30(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.377(3)
C1 C2 1.377(3)
C1 O1 1.383(3)
C2 C3 1.386(4)
C2 Cl1 1.718(2)
C3 C4 1.371(4)
C3 H3 0.9300
C4 C5 1.364(4)
C4 H4 0.9300
C5 C6 1.384(4)
C5 H5 0.9300
C6 Cl2 1.725(3)
C7 O2 1.199(3)
C7 O1 1.365(3)
C7 C8 1.470(3)
C8 C13 1.379(3)
C8 C9 1.385(3)
C9 C10 1.382(4)
C9 H9 0.9300
C10 C11 1.379(4)
C10 H10 0.9300
C11 C12 1.372(4)
C11 C14 1.513(4)
C12 C13 1.389(4)
C12 H12 0.9300
C13 H13 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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 -0.9(4)
O1 C1 C2 C3 -177.0(2)
C6 C1 C2 Cl1 179.23(18)
O1 C1 C2 Cl1 3.2(3)
C1 C2 C3 C4 0.8(4)
Cl1 C2 C3 C4 -179.3(2)
C2 C3 C4 C5 -0.1(4)
C3 C4 C5 C6 -0.6(4)
C2 C1 C6 C5 0.2(4)
O1 C1 C6 C5 176.3(2)
C2 C1 C6 Cl2 -178.59(18)
O1 C1 C6 Cl2 -2.5(3)
C4 C5 C6 C1 0.5(4)
C4 C5 C6 Cl2 179.3(2)
O2 C7 C8 C13 8.5(4)
O1 C7 C8 C13 -171.0(2)
O2 C7 C8 C9 -172.7(3)
O1 C7 C8 C9 7.8(3)
C13 C8 C9 C10 1.7(4)
C7 C8 C9 C10 -177.0(2)
C8 C9 C10 C11 -0.2(5)
C9 C10 C11 C12 -1.0(5)
C9 C10 C11 C14 179.0(3)
C10 C11 C12 C13 0.5(4)
C14 C11 C12 C13 -179.4(3)
C9 C8 C13 C12 -2.2(4)
C7 C8 C13 C12 176.6(2)
C11 C12 C13 C8 1.0(4)
O2 C7 O1 C1 -8.0(3)
C8 C7 O1 C1 171.58(18)
C6 C1 O1 C7 100.0(3)
C2 C1 O1 C7 -84.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13692540
