#------------------------------------------------------------------------------
#$Date: 2016-06-11 05:09:12 +0300 (Sat, 11 Jun 2016) $
#$Revision: 183347 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/17/2241708.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_2241708
loop_
_publ_author_name
'Cirbes, Cady'
'Tanski, Joseph M.'
_publ_section_title
;
 Crystallographic and spectroscopic characterization of
 (R)-O-acetylmandelic acid
;
_journal_coeditor_code           PK2580
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              901
_journal_page_last               903
_journal_paper_doi               10.1107/S2056989016008653
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C10 H10 O4'
_chemical_formula_moiety         'C10 H10 O4'
_chemical_formula_sum            'C10 H10 O4'
_chemical_formula_weight         194.18
_chemical_name_common            '(R)-(-)-O-acetylmandelic acid'
_chemical_name_systematic
;
(R)-(-)-2-Acetoxy-2-phenylacetic acid
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1047(10)
_cell_length_b                   10.0086(11)
_cell_length_c                   10.5871(11)
_cell_measurement_reflns_used    8300
_cell_measurement_temperature    125.(2)
_cell_measurement_theta_max      66.5813
_cell_measurement_theta_min      4.1758
_cell_volume                     964.75(18)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009),
Mercury (Macrae et al.,  2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_source         'Cu IuS micro-focus source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8953
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         6.08
_exptl_absorpt_coefficient_mu    0.880
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.185
_refine_ls_abs_structure_details
;
Flack x determined using 691 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013); Hooft y calculated with
PLATON (Spek, 2009)
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0336P)²+0.1385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0623
_reflns_number_gt                1693
_reflns_number_total             1698
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2580sup1.cif
_cod_data_source_block           I
_cod_database_code               2241708
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_occupancy
O O1 0.42132(13) 0.46237(13) 0.08956(12) 0.0329(3) Uani d 1
H H1 0.355(2) 0.479(2) 0.035(2) 0.039 Uiso d 1
O O2 0.35211(12) 0.66275(12) 0.16115(11) 0.0286(3) Uani d 1
O O3 0.50941(12) 0.63319(11) 0.37499(9) 0.0235(3) Uani d 1
O O4 0.29716(12) 0.53107(12) 0.42058(10) 0.0273(3) Uani d 1
C C1 0.53382(16) 0.53625(15) 0.27588(13) 0.0200(3) Uani d 1
H H1A 0.5199 0.4438 0.3097 0.024 Uiso calc 1
C C2 0.69072(15) 0.55447(14) 0.23211(13) 0.0184(3) Uani d 1
C C3 0.79939(18) 0.47071(16) 0.27844(16) 0.0272(4) Uani d 1
H H3A 0.7744 0.3988 0.3329 0.033 Uiso calc 1
C C4 0.94513(18) 0.49242(17) 0.2450(2) 0.0346(4) Uani d 1
H H4A 1.0198 0.4358 0.2776 0.042 Uiso calc 1
C C5 0.98206(18) 0.59621(18) 0.16417(17) 0.0326(4) Uani d 1
H H5A 1.0818 0.6109 0.1418 0.039 Uiso calc 1
C C6 0.87356(18) 0.67809(18) 0.11641(16) 0.0303(4) Uani d 1
H H6A 0.8985 0.7482 0.0599 0.036 Uiso calc 1
C C7 0.72770(17) 0.65833(17) 0.15078(14) 0.0242(3) Uani d 1
H H7A 0.6534 0.7157 0.1187 0.029 Uiso calc 1
C C8 0.42388(15) 0.56275(15) 0.16993(14) 0.0201(3) Uani d 1
C C9 0.38220(17) 0.62321(16) 0.43773(14) 0.0237(3) Uani d 1
C C10 0.3600(2) 0.7365(2) 0.52655(17) 0.0364(4) Uani d 1
H H10A 0.4523 0.7555 0.5707 0.055 Uiso calc 1
H H10B 0.2842 0.7128 0.5883 0.055 Uiso calc 1
H H10C 0.329 0.8158 0.4792 0.055 Uiso calc 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 O1 H1 107.2(15)
C9 O3 C1 116.28(11)
O3 C1 C2 106.65(11)
O3 C1 C8 108.41(11)
C2 C1 C8 111.91(12)
O3 C1 H1A 109.9
C2 C1 H1A 109.9
C8 C1 H1A 109.9
C3 C2 C7 119.87(14)
C3 C2 C1 119.51(13)
C7 C2 C1 120.54(13)
C2 C3 C4 119.76(15)
C2 C3 H3A 120.1
C4 C3 H3A 120.1
C5 C4 C3 120.37(16)
C5 C4 H4A 119.8
C3 C4 H4A 119.8
C6 C5 C4 119.83(15)
C6 C5 H5A 120.1
C4 C5 H5A 120.1
C5 C6 C7 120.22(16)
C5 C6 H6A 119.9
C7 C6 H6A 119.9
C6 C7 C2 119.95(14)
C6 C7 H7A 120.0
C2 C7 H7A 120.0
O2 C8 O1 125.26(14)
O2 C8 C1 124.01(14)
O1 C8 C1 110.72(12)
O4 C9 O3 122.18(14)
O4 C9 C10 125.84(14)
O3 C9 C10 111.98(13)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.3168(19)
O1 H1 0.852(19)
O2 C8 1.1989(19)
O3 C9 1.3389(18)
O3 C1 1.4463(17)
O4 C9 1.218(2)
C1 C2 1.5128(19)
C1 C8 1.527(2)
C1 H1A 1.0
C2 C3 1.386(2)
C2 C7 1.391(2)
C3 C4 1.391(2)
C3 H3A 0.95
C4 C5 1.387(3)
C4 H4A 0.95
C5 C6 1.380(3)
C5 H5A 0.95
C6 C7 1.391(2)
C6 H6A 0.95
C7 H7A 0.95
C9 C10 1.487(2)
C10 H10A 0.98
C10 H10B 0.98
C10 H10C 0.98
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 O4 2_564 0.852(19) 1.84(2) 2.6761(16) 165(2) y
C10 H10B O1 2_565 0.98 2.56 3.312(2) 133.1 ?
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
C9 O3 C1 C2 -172.13(12)
C9 O3 C1 C8 67.21(15)
O3 C1 C2 C3 98.10(15)
C8 C1 C2 C3 -143.51(14)
O3 C1 C2 C7 -78.78(16)
C8 C1 C2 C7 39.62(18)
C7 C2 C3 C4 1.1(2)
C1 C2 C3 C4 -175.84(16)
C2 C3 C4 C5 -0.9(3)
C3 C4 C5 C6 -0.2(3)
C4 C5 C6 C7 1.1(3)
C5 C6 C7 C2 -1.0(3)
C3 C2 C7 C6 -0.2(2)
C1 C2 C7 C6 176.71(15)
O3 C1 C8 O2 13.69(19)
C2 C1 C8 O2 -103.65(16)
O3 C1 C8 O1 -167.43(12)
C2 C1 C8 O1 75.23(15)
C1 O3 C9 O4 6.3(2)
C1 O3 C9 C10 -173.19(13)

_cod_database_fobs_code 2241708
