#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/89/2218926.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_2218926
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Babitha, K. S.'
'Fuess, Hartmut'
_publ_section_title
;
 3,5-Dichlorophenyl 4-methylbenzoate
;
_journal_coeditor_code           BX2159
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1545
_journal_paper_doi               10.1107/S1600536808022277
_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
;
3,5-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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9273(6)
_cell_length_b                   28.412(4)
_cell_length_c                   11.7050(10)
_cell_measurement_reflns_used    3406
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.25
_cell_volume                     1302.8(3)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ
;
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7613
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_T_max  0.9620
_exptl_absorpt_correction_T_min  0.7996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0404
_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)+(0.0783P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1393
_reflns_number_gt                1755
_reflns_number_total             2621
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2159.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218926
_cod_database_fobs_code          2218926
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 0.4042(6) 0.15541(8) -0.1194(2) 0.0418(6) Uani d . 1
C C2 0.2829(6) 0.13459(9) -0.0235(2) 0.0444(6) Uani d . 1
H H2 0.200(6) 0.1519(9) 0.035(2) 0.053 Uiso d . 1
C C3 0.2772(6) 0.08640(9) -0.01881(19) 0.0419(6) Uani d . 1
C C4 0.3809(6) 0.05839(9) -0.1061(2) 0.0442(6) Uani d . 1
H H4 0.373(5) 0.0228(10) -0.0960(19) 0.053 Uiso d . 1
C C5 0.4990(6) 0.08058(9) -0.20047(19) 0.0413(6) Uani d . 1
C C6 0.5140(6) 0.12902(9) -0.2088(2) 0.0432(6) Uani d . 1
H H6 0.583(6) 0.1444(9) -0.270(2) 0.052 Uiso d . 1
C C7 0.5453(6) 0.23217(9) -0.0486(2) 0.0450(6) Uani d . 1
C C8 0.4837(6) 0.28221(8) -0.0721(2) 0.0405(6) Uani d . 1
C C9 0.3278(7) 0.29931(10) -0.1734(2) 0.0492(7) Uani d . 1
H H9 0.260(7) 0.2789(10) -0.231(2) 0.059 Uiso d . 1
C C10 0.2734(7) 0.34658(10) -0.1884(2) 0.0506(7) Uani d . 1
H H10 0.164(6) 0.3558(9) -0.263(2) 0.061 Uiso d . 1
C C11 0.3722(6) 0.37871(9) -0.1031(2) 0.0437(6) Uani d . 1
C C12 0.5333(7) 0.36165(10) -0.0028(2) 0.0477(7) Uani d . 1
H H12 0.607(6) 0.3843(9) 0.049(2) 0.057 Uiso d . 1
C C13 0.5880(7) 0.31429(9) 0.0140(2) 0.0464(7) Uani d . 1
H H13 0.689(6) 0.3038(9) 0.079(2) 0.056 Uiso d . 1
C C14 0.3049(8) 0.43029(10) -0.1188(3) 0.0598(8) Uani d . 1
H H14A 0.5179 0.4468 -0.1197 0.072 Uiso calc R 1
H H14B 0.1808 0.4417 -0.0567 0.072 Uiso calc R 1
H H14C 0.1729 0.4354 -0.1899 0.072 Uiso calc R 1
O O1 0.3978(5) 0.20416(6) -0.13445(15) 0.0544(5) Uani d . 1
O O2 0.7075(5) 0.21609(6) 0.03319(17) 0.0650(6) Uani d . 1
Cl Cl1 0.13414(18) 0.05912(3) 0.10169(6) 0.0602(3) Uani d . 1
Cl Cl2 0.6296(2) 0.04648(2) -0.31227(6) 0.0605(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 0.0033 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
C6 C1 C2 121.8(2)
C6 C1 O1 116.5(2)
C2 C1 O1 121.5(2)
C3 C2 C1 117.9(2)
C3 C2 H2 119.8(16)
C1 C2 H2 122.3(16)
C2 C3 C4 122.7(2)
C2 C3 Cl1 119.06(19)
C4 C3 Cl1 118.25(19)
C3 C4 C5 117.6(2)
C3 C4 H4 118.3(13)
C5 C4 H4 124.1(13)
C4 C5 C6 122.0(2)
C4 C5 Cl2 118.88(19)
C6 C5 Cl2 119.10(18)
C5 C6 C1 118.0(2)
C5 C6 H6 124.0(17)
C1 C6 H6 117.9(17)
O2 C7 O1 122.2(2)
O2 C7 C8 126.1(2)
O1 C7 C8 111.6(2)
C9 C8 C13 118.6(2)
C9 C8 C7 124.0(2)
C13 C8 C7 117.5(2)
C10 C9 C8 120.7(2)
C10 C9 H9 119.5(18)
C8 C9 H9 119.9(18)
C9 C10 C11 121.3(3)
C9 C10 H10 115.5(16)
C11 C10 H10 123.2(16)
C12 C11 C10 117.9(2)
C12 C11 C14 120.9(2)
C10 C11 C14 121.2(2)
C13 C12 C11 121.5(3)
C13 C12 H12 123.8(17)
C11 C12 H12 114.7(17)
C12 C13 C8 120.0(2)
C12 C13 H13 120.5(17)
C8 C13 H13 119.5(17)
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 118.56(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.382(3)
C1 C2 1.382(3)
C1 O1 1.396(3)
C2 C3 1.371(3)
C2 H2 0.92(3)
C3 C4 1.379(3)
C3 Cl1 1.737(2)
C4 C5 1.381(3)
C4 H4 1.02(3)
C5 C6 1.382(3)
C5 Cl2 1.735(2)
C6 H6 0.89(3)
C7 O2 1.202(3)
C7 O1 1.377(3)
C7 C8 1.465(3)
C8 C9 1.383(4)
C8 C13 1.398(3)
C9 C10 1.369(4)
C9 H9 0.91(3)
C10 C11 1.387(4)
C10 H10 0.98(3)
C11 C12 1.382(3)
C11 C14 1.498(3)
C12 C13 1.375(4)
C12 H12 0.91(3)
C13 H13 0.89(3)
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 0.6(4)
O1 C1 C2 C3 175.7(2)
C1 C2 C3 C4 -1.2(4)
C1 C2 C3 Cl1 178.75(18)
C2 C3 C4 C5 0.9(4)
Cl1 C3 C4 C5 -179.01(18)
C3 C4 C5 C6 -0.1(4)
C3 C4 C5 Cl2 -179.67(18)
C4 C5 C6 C1 -0.4(4)
Cl2 C5 C6 C1 179.14(18)
C2 C1 C6 C5 0.2(4)
O1 C1 C6 C5 -175.2(2)
O2 C7 C8 C9 172.5(3)
O1 C7 C8 C9 -6.3(4)
O2 C7 C8 C13 -7.9(4)
O1 C7 C8 C13 173.3(2)
C13 C8 C9 C10 -0.8(4)
C7 C8 C9 C10 178.9(2)
C8 C9 C10 C11 0.0(4)
C9 C10 C11 C12 1.1(4)
C9 C10 C11 C14 -178.5(2)
C10 C11 C12 C13 -1.5(4)
C14 C11 C12 C13 178.1(2)
C11 C12 C13 C8 0.8(4)
C9 C8 C13 C12 0.3(4)
C7 C8 C13 C12 -179.3(2)
O2 C7 O1 C1 7.5(4)
C8 C7 O1 C1 -173.6(2)
C6 C1 O1 C7 -131.0(2)
C2 C1 O1 C7 53.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24740443
