#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/32/2203227.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_2203227
loop_
_publ_author_name
'Mughal, Robila K.'
'Pritchard, Robin G.'
'Davey, Roger J.'
_publ_section_title
;
 (2S)-[(2S)-2-Hydroxy-2-phenylethanoyloxy]phenylacetic
 acid
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o232
_journal_page_last               o233
_journal_paper_doi               10.1107/S1600536804000741
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C16 H14 O5'
_chemical_formula_moiety         'C16 H14 O5'
_chemical_formula_sum            'C16 H14 O5'
_chemical_formula_weight         286.27
_chemical_name_systematic        ?
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difamp
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 114.107(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5196(4)
_cell_length_b                   6.4129(3)
_cell_length_c                   11.7201(7)
_cell_measurement_reflns_used    4075
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      1.018
_cell_volume                     721.69(6)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2000)'
_computing_data_reduction
'HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and CERIUS² (Accelrys, 2001) '
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4184
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        27.34
_diffrn_reflns_theta_max         27.34
_diffrn_reflns_theta_min         3.38
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.213
_refine_ls_extinction_coef       0.115(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         1760
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0403
_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)+(0.0442P)²+0.1103P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                1413
_reflns_number_total             1760
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6068.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2203227
_cod_database_fobs_code          2203227
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_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_type_symbol
C1 0.1660(3) 0.8701(4) 0.0327(2) 0.0286(5) Uani d . 1 C
C2 0.3125(3) 0.7920(4) 0.0599(2) 0.0296(5) Uani d . 1 C
H2 0.3782 0.909 0.0833 0.035 Uiso calc R 1 H
C3 0.3165(2) 0.6790(4) -0.0517(2) 0.0288(5) Uani d . 1 C
C4 0.3786(3) 0.7720(4) -0.1229(3) 0.0377(6) Uani d . 1 C
H4 0.4203 0.9024 -0.101 0.045 Uiso calc R 1 H
C5 0.3780(3) 0.6688(5) -0.2269(3) 0.0469(7) Uani d . 1 C
H5 0.4186 0.7316 -0.2754 0.056 Uiso calc R 1 H
C6 0.3185(3) 0.4751(5) -0.2597(2) 0.0429(7) Uani d . 1 C
H6 0.3181 0.4079 -0.3302 0.051 Uiso calc R 1 H
C7 0.2593(3) 0.3809(5) -0.1873(2) 0.0413(7) Uani d . 1 C
H7 0.2208 0.2483 -0.2077 0.05 Uiso calc R 1 H
C8 0.2573(3) 0.4840(4) -0.0841(2) 0.0351(6) Uani d . 1 C
H8 0.2157 0.4213 -0.0364 0.042 Uiso calc R 1 H
C11 0.3771(3) 0.7273(4) 0.2742(2) 0.0315(6) Uani d . 1 C
C12 0.3946(3) 0.5596(4) 0.3701(2) 0.0338(6) Uani d . 1 C
H12 0.4399 0.4374 0.3528 0.041 Uiso calc R 1 H
C13 0.2518(3) 0.4995(4) 0.3619(2) 0.0342(6) Uani d . 1 C
C14 0.1924(4) 0.3124(5) 0.3093(3) 0.0668(11) Uani d . 1 C
H14 0.2399 0.2227 0.278 0.08 Uiso calc R 1 H
C15 0.0637(5) 0.2576(8) 0.3026(5) 0.111(2) Uani d . 1 C
H15 0.0254 0.1299 0.2678 0.133 Uiso calc R 1 H
C16 -0.0080(5) 0.3859(12) 0.3455(4) 0.111(2) Uani d . 1 C
H16 -0.096 0.3481 0.3392 0.134 Uiso calc R 1 H
C17 0.0495(4) 0.5730(10) 0.3988(3) 0.0881(18) Uani d . 1 C
H17 0.001 0.6612 0.4299 0.106 Uiso calc R 1 H
C18 0.1797(3) 0.6309(6) 0.4063(2) 0.0535(8) Uani d . 1 C
H18 0.218 0.7585 0.4413 0.064 Uiso calc R 1 H
O1 0.1407(2) 1.0446(3) -0.03237(18) 0.0400(5) Uani d . 1 O
H1 0.0615 1.0845 -0.047 0.06 Uiso calc R 1 H
O2 0.08478(19) 0.7830(3) 0.06471(17) 0.0404(5) Uani d . 1 O
O3 0.35120(18) 0.6433(3) 0.16153(14) 0.0351(4) Uani d . 1 O
O12 0.38098(19) 0.9121(3) 0.29324(16) 0.0365(5) Uani d . 1 O
O13 0.4817(2) 0.6462(3) 0.48698(17) 0.0441(5) Uani d . 1 O
H13 0.5145 0.5523 0.5382 0.066 Uiso calc R 1 H
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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 '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
O2 C1 O1 125.0(2)
O2 C1 C2 124.6(2)
O1 C1 C2 110.3(2)
O3 C2 C3 107.35(19)
O3 C2 C1 107.97(19)
C3 C2 C1 111.07(19)
O3 C2 H2 110.1
C3 C2 H2 110.1
C1 C2 H2 110.1
C8 C3 C4 119.7(2)
C8 C3 C2 120.3(2)
C4 C3 C2 120.0(2)
C5 C4 C3 119.3(3)
C5 C4 H4 120.3
C3 C4 H4 120.3
C6 C5 C4 121.1(3)
C6 C5 H5 119.5
C4 C5 H5 119.5
C5 C6 C7 119.5(3)
C5 C6 H6 120.2
C7 C6 H6 120.2
C6 C7 C8 120.0(3)
C6 C7 H7 120
C8 C7 H7 120
C3 C8 C7 120.4(2)
C3 C8 H8 119.8
C7 C8 H8 119.8
O12 C11 O3 123.6(2)
O12 C11 C12 125.4(2)
O3 C11 C12 111.0(2)
O13 C12 C11 105.9(2)
O13 C12 C13 113.2(2)
C11 C12 C13 108.5(2)
O13 C12 H12 109.7
C11 C12 H12 109.7
C13 C12 H12 109.7
C18 C13 C14 119.1(3)
C18 C13 C12 120.5(3)
C14 C13 C12 120.4(3)
C15 C14 C13 120.4(4)
C15 C14 H14 119.8
C13 C14 H14 119.8
C16 C15 C14 120.9(5)
C16 C15 H15 119.5
C14 C15 H15 119.5
C15 C16 C17 119.6(4)
C15 C16 H16 120.2
C17 C16 H16 120.2
C16 C17 C18 120.2(5)
C16 C17 H17 119.9
C18 C17 H17 119.9
C13 C18 C17 119.8(4)
C13 C18 H18 120.1
C17 C18 H18 120.1
C1 O1 H1 109.5
C11 O3 C2 114.8(2)
C12 O13 H13 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.202(3)
C1 O1 1.319(3)
C1 C2 1.525(3)
C2 O3 1.449(3)
C2 C3 1.511(3)
C2 H2 0.98
C3 C8 1.380(4)
C3 C4 1.388(3)
C4 C5 1.385(4)
C4 H4 0.93
C5 C6 1.373(5)
C5 H5 0.93
C6 C7 1.380(4)
C6 H6 0.93
C7 C8 1.386(4)
C7 H7 0.93
C8 H8 0.93
C11 O12 1.203(3)
C11 O3 1.347(3)
C11 C12 1.511(4)
C12 O13 1.414(3)
C12 C13 1.515(4)
C12 H12 0.98
C13 C18 1.370(4)
C13 C14 1.377(4)
C14 C15 1.369(6)
C14 H14 0.93
C15 C16 1.345(8)
C15 H15 0.93
C16 C17 1.374(9)
C16 H16 0.93
C17 C18 1.387(5)
C17 H17 0.93
C18 H18 0.93
O1 H1 0.82
O13 H13 0.82
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
O1 H1 O2 2 0.82 1.94 2.715(3) 157
O13 H13 O12 2_646 0.82 2.04 2.817(3) 159
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
O2 C1 C2 O3 -18.6(3)
O1 C1 C2 O3 162.27(19)
O2 C1 C2 C3 98.8(3)
O1 C1 C2 C3 -80.3(2)
O3 C2 C3 C8 45.5(3)
C1 C2 C3 C8 -72.3(3)
O3 C2 C3 C4 -135.1(2)
C1 C2 C3 C4 107.1(2)
C8 C3 C4 C5 1.1(4)
C2 C3 C4 C5 -178.2(2)
C3 C4 C5 C6 -0.8(4)
C4 C5 C6 C7 -0.5(4)
C5 C6 C7 C8 1.6(4)
C4 C3 C8 C7 -0.1(4)
C2 C3 C8 C7 179.2(2)
C6 C7 C8 C3 -1.2(4)
O12 C11 C12 O13 -29.2(4)
O3 C11 C12 O13 153.0(2)
O12 C11 C12 C13 92.7(3)
O3 C11 C12 C13 -85.1(2)
O13 C12 C13 C18 44.0(3)
C11 C12 C13 C18 -73.3(3)
O13 C12 C13 C14 -136.3(3)
C11 C12 C13 C14 106.4(3)
C18 C13 C14 C15 -0.7(5)
C12 C13 C14 C15 179.6(3)
C13 C14 C15 C16 0.9(6)
C14 C15 C16 C17 -1.1(7)
C15 C16 C17 C18 1.1(6)
C14 C13 C18 C17 0.7(4)
C12 C13 C18 C17 -179.6(3)
C16 C17 C18 C13 -0.9(5)
O12 C11 O3 C2 -6.6(3)
C12 C11 O3 C2 171.2(2)
C3 C2 O3 C11 168.6(2)
C1 C2 O3 C11 -71.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21174473
