##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section B. It has been peer reviewed under the auspices  #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary may be obtained from        #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#           Copyright International Union of Crystallography                 #
#                                                                            #
##############################################################################

data_oPPA
_audit_creation_method     'SHELXL-97 and manual editing'
_chemical_name_systematic
;
R-(+)-2-phenoxypropionic acid
;
_chemical_formula_moiety     'C9 H10 O3'
_chemical_formula_sum     'C9 H10 O3'
_chemical_formula_weight     166.17
_chemical_melting_point     359
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     8.5312(15)
_cell_length_b     4.8321(8)
_cell_length_c     10.125(2)
_cell_angle_alpha     90.00
_cell_angle_beta     92.031(16)
_cell_angle_gamma     90.00
_cell_volume     417.14(14)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     20
_cell_measurement_theta_min     39.26
_cell_measurement_theta_max     40.23
_cell_measurement_temperature     122.4(5)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.323
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     176
_exptl_absorpt_coefficient_mu     0.828
_exptl_absorpt_correction_type     'numerical'
_exptl_absorpt_process_details     '(DeTitta, 1985)'
_exptl_absorpt_correction_T_min     0.770
_exptl_absorpt_correction_T_max     0.954
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     122.4(5)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf-Nonius CAD4'
_diffrn_measurement_method     'ω--2θ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3609
_diffrn_reflns_av_R_equivalents     0.0100
_diffrn_reflns_av_sigmaI/netI     0.0092
_diffrn_reflns_theta_min     4.37
_diffrn_reflns_theta_max     74.93
_diffrn_reflns_theta_full     74.93
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     5
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     166.7
_diffrn_standards_decay_%     none
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1714
_reflns_number_gt     1697
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0222
_refine_ls_R_factor_gt     0.0220
_refine_ls_wR_factor_gt     0.0583
_refine_ls_wR_factor_ref     0.0584
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.047
_refine_ls_number_reflns     1714
_refine_ls_number_parameters     150
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     sigma
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0357P)²+0.0553P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.147
_refine_diff_density_min     -0.129
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.043(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     -0.03(13)
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'
_computing_data_collection     'Enraf-Nonius Express'
_computing_cell_refinement     'Enraf-Nonius Express'
_computing_data_reduction     'DREADD (Blessing, 1987)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    O7 0.80476(8) 0.72279(16) 0.84006(6) 0.01970(17) Uani d . 1 . . O
    O10 0.54521(9) 0.99296(15) 0.58652(7) 0.02436(19) Uani d . 1 . . O
    O11 0.63493(9) 0.56663(15) 0.63140(7) 0.02264(18) Uani d . 1 . . O
    H11 0.573(2) 0.520(4) 0.5570(18) 0.053(5) Uiso d . 1 . . H
    C1 0.94273(11) 0.6381(2) 0.78654(9) 0.0182(2) Uani d . 1 . . C
    C2 1.02327(11) 0.4340(2) 0.85913(10) 0.0218(2) Uani d . 1 . . C
    H2 0.9736(16) 0.359(3) 0.9430(13) 0.028(3) Uiso d . 1 . . H
    C3 1.16425(13) 0.3328(2) 0.81505(11) 0.0269(2) Uani d . 1 . . C
    H3 1.2188(16) 0.182(4) 0.8663(14) 0.036(4) Uiso d . 1 . . H
    C4 1.22656(12) 0.4351(3) 0.69956(11) 0.0279(2) Uani d . 1 . . C
    H4 1.3247(18) 0.363(3) 0.6676(14) 0.035(4) Uiso d . 1 . . H
    C5 1.14662(12) 0.6389(2) 0.62912(11) 0.0262(2) Uani d . 1 . . C
    H5 1.1875(17) 0.717(4) 0.5501(16) 0.043(4) Uiso d . 1 . . H
    C6 1.00386(11) 0.7407(2) 0.67074(9) 0.0222(2) Uani d . 1 . . C
    H6 0.9525(17) 0.883(3) 0.6212(15) 0.034(4) Uiso d . 1 . . H
    C121 0.60345(13) 1.0468(3) 0.87583(10) 0.0272(2) Uani d . 1 . . C
    H121 0.5429(16) 1.203(4) 0.8370(14) 0.034(3) Uiso d . 1 . . H
    H122 0.5362(18) 0.896(4) 0.9034(15) 0.038(4) Uiso d . 1 . . H
    H123 0.6642(17) 1.126(3) 0.9563(15) 0.040(4) Uiso d . 1 . . H
    C8 0.71599(10) 0.9357(2) 0.77566(9) 0.0178(2) Uani d . 1 . . C
    H81 0.7830(15) 1.090(3) 0.7455(12) 0.021(3) Uiso d . 1 . . H
    C9 0.62380(11) 0.8325(2) 0.65371(9) 0.01636(19) Uani d . 1 . . C
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
    O7 0.0185(3) 0.0233(4) 0.0172(3) 0.0045(3) -0.0010(2) 0.0027(3)
    O10 0.0309(4) 0.0186(4) 0.0227(3) 0.0023(3) -0.0112(3) 0.0008(3)
    O11 0.0264(4) 0.0155(3) 0.0253(4) 0.0011(3) -0.0097(3) -0.0017(3)
    C1 0.0168(4) 0.0195(5) 0.0178(4) -0.0003(3) -0.0037(3) -0.0043(3)
    C2 0.0229(5) 0.0226(5) 0.0195(4) 0.0013(4) -0.0045(4) 0.0002(4)
    C3 0.0242(5) 0.0264(5) 0.0295(5) 0.0059(4) -0.0065(4) -0.0031(5)
    C4 0.0206(4) 0.0323(6) 0.0308(5) 0.0030(4) 0.0000(4) -0.0072(5)
    C5 0.0245(5) 0.0307(6) 0.0236(5) -0.0034(4) 0.0021(4) -0.0038(4)
    C6 0.0235(5) 0.0232(5) 0.0198(4) -0.0003(4) -0.0017(4) 0.0003(4)
    C121 0.0290(5) 0.0320(6) 0.0204(5) 0.0106(5) 0.0000(4) -0.0033(4)
    C8 0.0188(4) 0.0178(4) 0.0165(4) 0.0018(4) -0.0031(3) -0.0003(4)
    C9 0.0164(4) 0.0159(4) 0.0167(4) -0.0006(4) 0.0002(3) 0.0014(4)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    O7 C1 . 1.3753(12) ?
    O7 C8 . 1.4221(12) ?
    O10 C9 . 1.2169(12) ?
    O11 C9 . 1.3086(12) ?
    O11 H11 . 0.933(19) ?
    C1 C6 . 1.3913(14) ?
    C1 C2 . 1.3963(14) ?
    C2 C3 . 1.3867(15) ?
    C2 H2 . 1.028(14) ?
    C3 C4 . 1.3922(17) ?
    C3 H3 . 1.001(16) ?
    C4 C5 . 1.3817(16) ?
    C4 H4 . 0.972(15) ?
    C5 C6 . 1.3925(15) ?
    C5 H5 . 0.962(17) ?
    C6 H6 . 0.949(16) ?
    C121 C8 . 1.5192(13) ?
    C121 H121 . 0.988(16) ?
    C121 H122 . 0.973(18) ?
    C121 H123 . 1.025(15) ?
    C8 C9 . 1.5242(13) ?
    C8 H81 . 0.994(14) ?
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
    C1 O7 C8 . . 118.93(7) ?
    C9 O11 H11 . . 109.6(13) ?
    O7 C1 C6 . . 125.29(9) ?
    O7 C1 C2 . . 114.50(8) ?
    C6 C1 C2 . . 120.20(9) ?
    C3 C2 C1 . . 119.73(10) ?
    C3 C2 H2 . . 122.0(8) ?
    C1 C2 H2 . . 118.3(8) ?
    C2 C3 C4 . . 120.42(10) ?
    C2 C3 H3 . . 118.9(8) ?
    C4 C3 H3 . . 120.7(8) ?
    C5 C4 C3 . . 119.38(10) ?
    C5 C4 H4 . . 119.8(9) ?
    C3 C4 H4 . . 120.8(9) ?
    C4 C5 C6 . . 121.10(10) ?
    C4 C5 H5 . . 121.6(10) ?
    C6 C5 H5 . . 117.3(10) ?
    C1 C6 C5 . . 119.16(10) ?
    C1 C6 H6 . . 121.6(9) ?
    C5 C6 H6 . . 119.2(9) ?
    C8 C121 H121 . . 109.8(8) ?
    C8 C121 H122 . . 108.7(9) ?
    H121 C121 H122 . . 112.3(12) ?
    C8 C121 H123 . . 110.5(8) ?
    H121 C121 H123 . . 105.9(12) ?
    H122 C121 H123 . . 109.8(12) ?
    O7 C8 C121 . . 106.77(8) ?
    O7 C8 C9 . . 112.70(8) ?
    C121 C8 C9 . . 109.65(8) ?
    O7 C8 H81 . . 112.4(7) ?
    C121 C8 H81 . . 108.9(7) ?
    C9 C8 H81 . . 106.4(7) ?
    O10 C9 O11 . . 124.81(9) ?
    O10 C9 C8 . . 120.18(9) ?
    O11 C9 C8 . . 114.99(8) ?
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
    C8 O7 C1 C6 . . . . -1.27(14) ?
    C8 O7 C1 C2 . . . . 178.24(8) ?
    O7 C1 C2 C3 . . . . -179.82(9) ?
    C6 C1 C2 C3 . . . . -0.27(14) ?
    C1 C2 C3 C4 . . . . 0.54(16) ?
    C2 C3 C4 C5 . . . . 0.04(16) ?
    C3 C4 C5 C6 . . . . -0.91(16) ?
    O7 C1 C6 C5 . . . . 178.92(9) ?
    C2 C1 C6 C5 . . . . -0.57(15) ?
    C4 C5 C6 C1 . . . . 1.17(16) ?
    C1 O7 C8 C121 . . . . -162.36(8) ?
    C1 O7 C8 C9 . . . . 77.20(10) ?
    O7 C8 C9 O10 . . . . -178.23(8) ?
    C121 C8 C9 O10 . . . . 62.99(12) ?
    O7 C8 C9 O11 . . . . 2.96(11) ?
    C121 C8 C9 O11 . . . . -115.81(10) ?
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
    O11 H11 O10 2_646 0.933(19) 1.744(19) 2.6677(11) 170(2)

data_global
_journal_date_recd_electronic     2002-09-23
_journal_date_accepted     2002-11-22
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2003
_journal_volume     59
_journal_issue      1
_journal_page_first     132
_journal_page_last     140
_journal_paper_category     FA
_publ_contact_author
; Sine Larsen
  Centre for Crystallographic Studies
  University of Copenhagen
  Department of Chemistry
  Universitetsparken 5
  2100 Copenhagen Ø
  Denmark
;
_publ_contact_author_email     sine@ccs.ki.ku.dk
_publ_section_title
;
Hydrogen bonding in enantiomeric vs racemic mono
carboxylic acids; a case study of 2-phenoxypropionic acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Henning O. Sørensen'
; Centre for Crystallographic Studies
  University of Copenhagen
  Department of Chemistry
  Universitetsparken 5
  2100 Copenhagen Ø
  Denmark
;
    'Sine Larsen'
; Centre for Crystallographic Studies
  University of Copenhagen
  Department of Chemistry
  Universitetsparken 5
  2100 Copenhagen Ø
  Denmark
;

