#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/31/2223179.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_2223179
loop_
_publ_author_name
'Adeel, Muhammad'
'Ali, Irshad'
'Langer, Peter'
'Villinger, Alexander'
_publ_section_title
;
 Methyl 5-chloro-2-hydroxy-3-(4-methoxyphenyl)-4,6-dimethylbenzoate
;
_journal_coeditor_code           PV2189
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2176
_journal_paper_doi               10.1107/S1600536809031614
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H17 Cl O4'
_chemical_formula_moiety         'C17 H17 Cl O4'
_chemical_formula_sum            'C17 H17 Cl O4'
_chemical_formula_weight         320.76
_chemical_melting_point          367
_chemical_name_systematic
;
Methyl 5-chloro-2-hydroxy-3-(4-methoxyphenyl)-4,6-dimethylbenzoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.420(15)
_cell_angle_beta                 100.56(2)
_cell_angle_gamma                96.042(14)
_cell_formula_units_Z            2
_cell_length_a                   6.534(4)
_cell_length_b                   9.574(6)
_cell_length_c                   12.694(8)
_cell_measurement_reflns_used    7750
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      59.533
_cell_measurement_theta_min      6.383
_cell_volume                     767.3(8)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2005)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14947
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         4.40
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_correction_T_min  0.8683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.073P)²+0.0592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                3091
_reflns_number_total             3964
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2189.cif
_cod_data_source_block           I
_cod_database_code               2223179
_cod_database_fobs_code          2223179
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.09153(15) 0.87698(10) 0.26779(8) 0.0377(2) Uani d . 1 . .
H H1 -0.175(3) 0.892(2) 0.3196(17) 0.067(6) Uiso d . 1 . .
O O2 -0.25708(18) 0.99014(12) 0.41459(9) 0.0505(3) Uani d . 1 . .
O O3 -0.16796(18) 1.21628(12) 0.48417(9) 0.0491(3) Uani d . 1 . .
O O4 0.23627(16) 0.52864(10) -0.09022(8) 0.0405(2) Uani d . 1 . .
Cl Cl1 0.48249(6) 1.39934(4) 0.30599(3) 0.05110(15) Uani d . 1 . .
C C1 0.3067(2) 1.24545(14) 0.29830(10) 0.0313(3) Uani d . 1 . .
C C2 0.1636(2) 1.24546(14) 0.36668(10) 0.0310(3) Uani d . 1 . .
C C3 0.02086(19) 1.11978(13) 0.35519(9) 0.0279(3) Uani d . 1 . .
C C4 0.03415(19) 1.00141(13) 0.27908(10) 0.0272(3) Uani d . 1 . .
C C5 0.18323(18) 1.00544(13) 0.21221(9) 0.0265(3) Uani d . 1 . .
C C6 0.32076(19) 1.12961(13) 0.22127(9) 0.0282(3) Uani d . 1 . .
C C7 0.4785(2) 1.14192(16) 0.14895(11) 0.0386(3) Uani d . 1 . .
H H7A 0.4538 1.0572 0.0937 0.058 Uiso calc R 1 . .
H H7B 0.6207 1.1501 0.1925 0.058 Uiso calc R 1 . .
H H7C 0.4637 1.2265 0.1136 0.058 Uiso calc R 1 . .
C C8 -0.1451(2) 1.10217(14) 0.41965(10) 0.0318(3) Uani d . 1 . .
C C9 -0.3311(3) 1.20118(19) 0.54694(14) 0.0515(4) Uani d . 1 . .
H H9A -0.4673 1.1710 0.4978 0.077 Uiso calc R 1 . .
H H9B -0.3346 1.2925 0.5910 0.077 Uiso calc R 1 . .
H H9C -0.3018 1.1298 0.5945 0.077 Uiso calc R 1 . .
C C10 0.1683(3) 1.37309(18) 0.45028(13) 0.0513(4) Uani d . 1 . .
H H10A 0.2995 1.4367 0.4576 0.077 Uiso calc R 1 . .
H H10B 0.1599 1.3421 0.5202 0.077 Uiso calc R 1 . .
H H10C 0.0487 1.4235 0.4275 0.077 Uiso calc R 1 . .
C C11 0.18957(19) 0.87662(13) 0.13357(9) 0.0277(3) Uani d . 1 . .
C C12 0.0254(2) 0.82784(14) 0.04645(10) 0.0310(3) Uani d . 1 . .
H H12 -0.0962 0.8750 0.0389 0.037 Uiso calc R 1 . .
C C13 0.0333(2) 0.71183(14) -0.03026(10) 0.0320(3) Uani d . 1 . .
H H13 -0.0805 0.6811 -0.0899 0.038 Uiso calc R 1 . .
C C14 0.2094(2) 0.64160(13) -0.01864(10) 0.0312(3) Uani d . 1 . .
C C15 0.3732(2) 0.68633(15) 0.06955(11) 0.0366(3) Uani d . 1 . .
H H15 0.4927 0.6372 0.0785 0.044 Uiso calc R 1 . .
C C16 0.3628(2) 0.80242(15) 0.14448(11) 0.0348(3) Uani d . 1 . .
H H16 0.4760 0.8322 0.2046 0.042 Uiso calc R 1 . .
C C17 0.0787(3) 0.48428(16) -0.18492(11) 0.0427(3) Uani d . 1 . .
H H17A -0.0537 0.4516 -0.1644 0.064 Uiso calc R 1 . .
H H17B 0.1213 0.4064 -0.2306 0.064 Uiso calc R 1 . .
H H17C 0.0596 0.5642 -0.2252 0.064 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 H1 . . 104.4(13) ?
C8 O3 C9 . . 116.73(12) ?
C14 O4 C17 . . 118.03(11) ?
C2 C1 C6 . . 124.48(12) ?
C2 C1 Cl1 . . 118.94(10) ?
C6 C1 Cl1 . . 116.58(10) ?
C1 C2 C3 . . 116.76(12) ?
C1 C2 C10 . . 120.28(13) ?
C3 C2 C10 . . 122.94(12) ?
C4 C3 C2 . . 119.62(12) ?
C4 C3 C8 . . 116.31(12) ?
C2 C3 C8 . . 124.06(12) ?
O1 C4 C5 . . 115.99(11) ?
O1 C4 C3 . . 122.28(12) ?
C5 C4 C3 . . 121.72(12) ?
C6 C5 C4 . . 118.97(11) ?
C6 C5 C11 . . 121.90(11) ?
C4 C5 C11 . . 119.13(11) ?
C5 C6 C1 . . 118.42(12) ?
C5 C6 C7 . . 121.32(12) ?
C1 C6 C7 . . 120.25(12) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 O3 . . 120.57(12) ?
O2 C8 C3 . . 123.38(12) ?
O3 C8 C3 . . 116.05(12) ?
O3 C9 H9A . . 109.5 ?
O3 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O3 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C2 C10 H10A . . 109.5 ?
C2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12 C11 C16 . . 117.68(12) ?
C12 C11 C5 . . 121.30(11) ?
C16 C11 C5 . . 121.01(11) ?
C11 C12 C13 . . 121.91(12) ?
C11 C12 H12 . . 119.0 ?
C13 C12 H12 . . 119.0 ?
C14 C13 C12 . . 119.20(12) ?
C14 C13 H13 . . 120.4 ?
C12 C13 H13 . . 120.4 ?
O4 C14 C15 . . 115.94(12) ?
O4 C14 C13 . . 124.23(12) ?
C15 C14 C13 . . 119.83(12) ?
C16 C15 C14 . . 120.05(12) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C11 . . 121.29(12) ?
C15 C16 H16 . . 119.4 ?
C11 C16 H16 . . 119.4 ?
O4 C17 H17A . . 109.5 ?
O4 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O4 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.3495(17) ?
O1 H1 . 0.94(2) ?
O2 C8 . 1.2205(18) ?
O3 C8 . 1.3170(18) ?
O3 C9 . 1.4496(19) ?
O4 C14 . 1.3678(16) ?
O4 C17 . 1.4169(19) ?
Cl1 C1 . 1.7510(16) ?
C1 C2 . 1.3870(19) ?
C1 C6 . 1.4033(18) ?
C2 C3 . 1.417(2) ?
C2 C10 . 1.505(2) ?
C3 C4 . 1.4121(18) ?
C3 C8 . 1.4821(19) ?
C4 C5 . 1.4052(18) ?
C5 C6 . 1.3913(19) ?
C5 C11 . 1.4925(18) ?
C6 C7 . 1.5061(19) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C12 . 1.3850(18) ?
C11 C16 . 1.3937(19) ?
C12 C13 . 1.3914(18) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.3869(19) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.387(2) ?
C15 C16 . 1.382(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
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
_geom_hbond_publ_flag
O1 H1 O2 . 0.94(2) 1.63(2) 2.5061(18) 153(2) y
C7 H7C Cl1 . 0.98 2.74 2.957(2) 93 y
C10 H10A Cl1 . 0.98 2.45 3.003(2) 115 y
C10 H10B O3 . 0.98 2.28 2.662(2) 102 y
C10 H10C O3 . 0.98 2.57 2.662(2) 85 y
C9 H9A O2 2_476 0.98 2.73 3.242(3) 113 y
C9 H9C O2 2_476 0.98 2.96 3.242(3) 98 y
C15 H15 O4 2_665 0.95 2.50 3.437(2) 170 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.3(2) ?
Cl1 C1 C2 C3 . . . . 178.26(9) ?
C6 C1 C2 C10 . . . . 177.07(13) ?
Cl1 C1 C2 C10 . . . . -3.41(19) ?
C1 C2 C3 C4 . . . . 1.98(18) ?
C10 C2 C3 C4 . . . . -176.30(12) ?
C1 C2 C3 C8 . . . . -178.63(11) ?
C10 C2 C3 C8 . . . . 3.1(2) ?
C2 C3 C4 O1 . . . . 177.11(11) ?
C8 C3 C4 O1 . . . . -2.32(17) ?
C2 C3 C4 C5 . . . . -1.34(18) ?
C8 C3 C4 C5 . . . . 179.22(10) ?
O1 C4 C5 C6 . . . . -178.70(10) ?
C3 C4 C5 C6 . . . . -0.15(18) ?
O1 C4 C5 C11 . . . . 1.31(16) ?
C3 C4 C5 C11 . . . . 179.86(10) ?
C4 C5 C6 C1 . . . . 0.91(17) ?
C11 C5 C6 C1 . . . . -179.10(10) ?
C4 C5 C6 C7 . . . . -177.74(11) ?
C11 C5 C6 C7 . . . . 2.25(18) ?
C2 C1 C6 C5 . . . . -0.19(19) ?
Cl1 C1 C6 C5 . . . . -179.72(9) ?
C2 C1 C6 C7 . . . . 178.47(12) ?
Cl1 C1 C6 C7 . . . . -1.06(16) ?
C9 O3 C8 O2 . . . . -0.3(2) ?
C9 O3 C8 C3 . . . . 179.38(12) ?
C4 C3 C8 O2 . . . . 4.94(19) ?
C2 C3 C8 O2 . . . . -174.47(12) ?
C4 C3 C8 O3 . . . . -174.73(10) ?
C2 C3 C8 O3 . . . . 5.86(19) ?
C6 C5 C11 C12 . . . . -113.50(15) ?
C4 C5 C11 C12 . . . . 66.49(17) ?
C6 C5 C11 C16 . . . . 65.53(17) ?
C4 C5 C11 C16 . . . . -114.48(14) ?
C16 C11 C12 C13 . . . . -2.1(2) ?
C5 C11 C12 C13 . . . . 176.99(12) ?
C11 C12 C13 C14 . . . . 0.9(2) ?
C17 O4 C14 C15 . . . . -176.38(12) ?
C17 O4 C14 C13 . . . . 2.97(19) ?
C12 C13 C14 O4 . . . . -178.45(11) ?
C12 C13 C14 C15 . . . . 0.87(19) ?
O4 C14 C15 C16 . . . . 178.07(12) ?
C13 C14 C15 C16 . . . . -1.3(2) ?
C14 C15 C16 C11 . . . . 0.0(2) ?
C12 C11 C16 C15 . . . . 1.6(2) ?
C5 C11 C16 C15 . . . . -177.44(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743063
