#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2000579.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_2000579
loop_
_publ_author_name
'Ferguson, G.'
'Gallagher, J. F.'
'Fullwood, R.'
'Parker, D.'
_publ_section_title
;
 Oxonium (<i>R</i>)-<i>O</i>-acetylmandelate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1909
_journal_page_last               1911
_journal_volume                  48
_journal_year                    1992
_chemical_formula_moiety         'H3 O, C10 H9 O4 '
_chemical_formula_sum            'C10 H12 O5'
_chemical_formula_weight         212.20
_chemical_name_systematic
;
Oxonium (R)-O-acetylmandelate
;
_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'
_cell_angle_alpha                90.0
_cell_angle_beta                 104.879(6)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   7.6772(6)
_cell_length_b                   6.2628(5)
_cell_length_c                   12.4889(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      20.00
_cell_measurement_theta_min      10.00
_cell_volume                     580.34(8)
_computing_cell_refinement       'Enraf-Nonius CAD-4 software'
_computing_data_collection       'Enraf-Nonius CAD-4 software'
_computing_data_reduction        'NRCVAX DATRD2'
_computing_molecular_graphics    'NRCVAX and ORTEPII'
_computing_publication_material  'NRCVAX TABLES and Word-Perfect 5.1'
_computing_structure_refinement  'NRCVAX LSTSQ'
_computing_structure_solution    'NRCVAX SOLVER'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Nonius CAD-4    '
_diffrn_measurement_method       '\q/2\q scan b/P/b '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'xray tube'
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     0.70930
_diffrn_reflns_av_R_equivalents  0.005
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2511
_diffrn_reflns_theta_max         26.91
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_Rogers  1.00
_refine_ls_goodness_of_fit_obs   1.24
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1893
_refine_ls_R_factor_all          0.053
_refine_ls_R_factor_obs          0.039
_refine_ls_shift/esd_max         <0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      1/[\s^2^(F)+0.0012F^2^]
_refine_ls_wR_factor_all         0.061
_refine_ls_wR_factor_obs         0.055
_reflns_number_observed          1893
_reflns_number_total             2426
_reflns_observed_criterion       'Inet > 3.0\s(Inet)'
_[local]_cod_data_source_file    ha1019.cif
_[local]_cod_data_source_block   92-10
_[local]_cod_cif_authors_sg_H-M  'P 21'
_[local]_cod_chemical_formula_sum_orig 'C10 H12 O5 '
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        580.34(7)
_cod_database_code               2000579
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,-z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
_atom_site_aniso_type_symbol
O(1) 0.0437(7) 0.0418(8) 0.0465(8) 0.0118(14) 0.0050(11) -0.0170(14) O
O(2) 0.0488(9) 0.0855(14) 0.0845(14) -0.0283(19) -0.0037(17) -0.021(2) O
O(3) 0.0643(9) 0.0384(8) 0.0406(8) 0.0073(14) 0.0348(13) 0.0028(13) O
O(4) 0.1463(19) 0.0264(9) 0.0593(11) 0.025(2) 0.038(2) -0.0020(16) O
O(W) 0.0661(9) 0.0491(10) 0.0659(11) 0.0047(16) 0.0345(16) 0.0051(17) O
C(1) 0.0443(9) 0.0326(10) 0.0382(10) -0.0089(16) 0.0156(15) 0.0000(16) C
C(2) 0.0414(10) 0.0691(17) 0.0458(12) -0.001(2) 0.0113(17) -0.014(3) C
C(3) 0.0602(14) 0.090(2) 0.0738(19) 0.044(3) 0.002(3) 0.005(3) C
C(4) 0.0548(10) 0.0297(11) 0.0400(11) 0.0000(17) 0.0129(16) -0.0037(17) C
C(11) 0.0413(9) 0.0377(11) 0.0353(10) 0.0043(16) 0.0235(16) 0.0005(17) C
C(12) 0.0492(11) 0.0407(12) 0.0487(12) -0.0032(18) 0.0084(18) 0.0089(19) C
C(13) 0.0473(12) 0.0576(17) 0.0757(17) -0.017(2) 0.019(2) 0.000(3) C
C(14) 0.0416(10) 0.0748(17) 0.0612(14) 0.006(2) -0.0007(19) -0.006(3) C
C(15) 0.0522(12) 0.0765(19) 0.0541(13) 0.027(2) 0.002(2) 0.038(3) C
C(16) 0.0534(11) 0.0435(13) 0.0511(13) 0.0092(19) 0.0243(18) 0.019(2) C
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O(1) 0.72312(18) 0.24910 0.73775(12) 0.0457(7) Uani d . . O
O(2) 0.4892(2) 0.0515(5) 0.65104(17) 0.0764(12) Uani d . . O
O(3) 0.8681(2) 0.0492(4) 0.58554(12) 0.0470(8) Uani d . . O
O(4) 0.8980(3) -0.2502(4) 0.68155(16) 0.0787(14) Uani d . . O
O(W) 0.8487(2) -0.5338(4) 0.51118(15) 0.0603(10) Uani d . . O
C(1) 0.8282(3) 0.0561(4) 0.76964(16) 0.0389(10) Uani d . . C
C(2) 0.5539(3) 0.2254(5) 0.6789(2) 0.0531(13) Uani d . . C
C(3) 0.4592(4) 0.4352(6) 0.6535(3) 0.0777(18) Uani d . . C
C(4) 0.8652(3) -0.0576(4) 0.66919(18) 0.0426(11) Uani d . . C
C(11) 1.0032(3) 0.1224(4) 0.84925(16) 0.0378(10) Uani d . . C
C(12) 1.0803(3) 0.3199(4) 0.84185(19) 0.0477(11) Uani d . . C
C(13) 1.2419(3) 0.3736(5) 0.9150(2) 0.0614(15) Uani d . . C
C(14) 1.3269(3) 0.2329(6) 0.9968(2) 0.0617(14) Uani d . . C
C(15) 1.2507(3) 0.0351(6) 1.0034(2) 0.0632(14) Uani d . . C
C(16) 1.0890(3) -0.0198(5) 0.93026(19) 0.0496(12) Uani d . . C
HOW(1) 0.728 -0.506 0.449 0.0707 Uiso d T 0.75 H
HOW(2) 0.964 -0.512 0.480 0.0707 Uiso d T 0.75 H
HOW(3) 0.847 -0.678 0.550 0.0707 Uiso d T 0.75 H
HOW(4) 0.854 -0.420 0.580 0.0707 Uiso d T 0.75 H
H(1) 0.766 -0.039 0.806 0.0484 Uiso calc RT . H
H(3A) 0.339 0.412 0.611 0.0847 Uiso calc RT 0.5 H
H(3B) 0.458 0.505 0.721 0.0847 Uiso calc RT 0.5 H
H(3C) 0.520 0.522 0.612 0.0847 Uiso calc RT 0.5 H
H(3D) 0.540 0.547 0.685 0.0847 Uiso calc RT 0.5 H
H(3E) 0.420 0.454 0.576 0.0847 Uiso calc RT 0.5 H
H(3F) 0.358 0.438 0.684 0.0847 Uiso calc RT 0.5 H
H(12) 1.022 0.418 0.786 0.0562 Uiso calc RT . H
H(13) 1.295 0.509 0.909 0.0702 Uiso calc RT . H
H(14) 1.437 0.272 1.048 0.0692 Uiso calc RT . H
H(15) 1.310 -0.064 1.058 0.0709 Uiso calc RT . H
H(16) 1.037 -0.156 0.936 0.0593 Uiso calc RT . H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 'International Tables Vol. IV Table 2.2B'
H 0.000 0.000 'International Tables Vol. IV Table 2.2B'
N 0.004 0.003 'International Tables Vol. IV Table 2.2B'
O 0.008 0.006 'International Tables Vol. IV Table 2.2B'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 4 0
1 2 4
3 1 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C(1) O(1) C(2) . 117.09(17) yes
O(1) C(1) C(4) . 111.70(17) yes
O(1) C(1) C(11) . 106.9(2) yes
C(4) C(1) C(11) . 110.27(16) yes
O(1) C(2) O(2) . 122.1(3) yes
O(1) C(2) C(3) . 111.9(3) yes
O(2) C(2) C(3) . 126.0(2) yes
O(3) C(4) O(4) . 125.7(2) yes
O(3) C(4) C(1) . 118.9(2) yes
O(4) C(4) C(1) . 115.3(2) yes
C(1) C(11) C(12) . 121.7(2) no
C(1) C(11) C(16) . 118.8(2) no
C(12) C(11) C(16) . 119.6(2) no
C(11) C(12) C(13) . 120.0(2) no
C(12) C(13) C(14) . 120.6(3) no
C(13) C(14) C(15) . 119.3(2) no
C(14) C(15) C(16) . 120.4(2) no
C(11) C(16) C(15) . 120.1(3) yes
OW H(OW1) O(2) 2_646 175.5 no
OW H(OW2) O(3) 2_746 171.1 no
OW H(OW3) O(3) 1_545 163.9 no
OW H(OW4) O(4) . 170.1 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.451(3) yes
O(1) C(2) 1.326(3) yes
O(2) C(2) 1.211(4) yes
O(3) C(4) 1.246(3) yes
O(4) C(4) 1.234(4) yes
C(1) C(4) 1.531(3) yes
C(1) C(11) 1.510(3) yes
C(2) C(3) 1.496(5) yes
C(11) C(12) 1.385(4) no
C(11) C(16) 1.381(3) no
C(12) C(13) 1.380(3) no
C(13) C(14) 1.380(4) no
C(14) C(15) 1.382(5) no
C(15) C(16) 1.382(3) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
OW O(2) 2.902(3) 2_646 yes
HOW(1) O(2) 1.85 2_646 yes
OW O(3) 2.794(2) 2_746 yes
HOW(2) O(3) 1.74 2_746 yes
OW O(3) 2.763(3) 1_545 yes
HOW(3) O(3) 1.76 1_545 yes
OW O(4) 2.722(3) . yes
HOW(4) O(4) 1.62 . yes
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
_geom_torsion_publ_flag
C(2) O(1) C(1) C(4) 67.7(2) yes
C(2) O(1) C(1) C(11) -171.6(2) yes
C(1) O(1) C(2) O(2) -1.00(10) yes
C(1) O(1) C(2) C(3) 178.7(2) yes
O(1) C(1) C(4) O(3) 26.40(10) yes
O(1) C(1) C(4) O(4) -156.7(3) yes
C(11) C(1) C(4) O(3) -92.3(2) yes
C(11) C(1) C(4) O(4) 84.6(2) yes
O(1) C(1) C(11) C(12) -31.10(10) yes
O(1) C(1) C(11) C(16) 149.8(2) yes
C(4) C(1) C(11) C(12) 90.5(2) yes
C(4) C(1) C(11) C(16) -88.6(2) yes
C(1) C(11) C(12) C(13) -179.0(3) no
C(1) C(11) C(16) C(15) 179.1(3) no
C(16) C(11) C(12) C(13) 0.10(10) no
C(12) C(11) C(16) C(15) 0.00(10) no
C(11) C(12) C(13) C(14) -0.80(10) no
C(12) C(13) C(14) C(15) 1.40(10) no
C(13) C(14) C(15) C(16) -1.30(10) no
C(14) C(15) C(16) C(11) 0.60(10) no