#------------------------------------------------------------------------------
#$Date: 2016-03-24 00:36:23 +0100 (jue 24 de mar de 2016) $
#$Revision: 179538 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/07/4500717.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4500717
loop_
_publ_author_name
'Navare, Pranoti S.'
'MacDonald, John C.'
_publ_section_title
;
 Investigation of Stability and Structure in Three Homochiral and
 Heterochiral Crystalline Forms of 3-Phenyllactic Acid
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2422
_journal_paper_doi               10.1021/cg200171r
_journal_volume                  11
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_moiety         'C9 H10 O3'
_chemical_formula_sum            'C9 H10 O3'
_chemical_formula_weight         166.17
_chemical_melting_point          395.1
_chemical_name_common            'L-3-phenyllactic acid'
_chemical_name_systematic        '(S)-2-hydroxy-3-phenylpropionic acid'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8389(3)
_cell_length_b                   8.3195(5)
_cell_length_c                   16.9691(10)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    100(2)
_cell_volume                     824.30(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15638
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.40
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_correction_T_min  0.9802
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method water
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0368P)²+0.1930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                1960
_reflns_number_total             2044
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200171r_si_001.cif
_cod_data_source_block           3PLA_P212121
_cod_database_code               4500717
loop_
_symmetry_equiv_pos_as_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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C8 C 0.91468(18) 1.16477(13) 0.84500(6) 0.0148(2) Uani 1 1 d .
H8 H 0.9226 1.2607 0.8096 0.018 Uiso 1 1 calc R
C1 C 0.7010(2) 0.77345(13) 0.83449(6) 0.0191(2) Uani 1 1 d .
H1 H 0.5829 0.8113 0.8008 0.023 Uiso 1 1 calc R
C5 C 1.0770(2) 0.79965(13) 0.88966(6) 0.0186(2) Uani 1 1 d .
H5 H 1.2185 0.8555 0.8935 0.022 Uiso 1 1 calc R
C9 C 0.68836(18) 1.16910(12) 0.88887(6) 0.01424(19) Uani 1 1 d .
C6 C 0.9058(2) 0.85840(12) 0.84014(6) 0.0158(2) Uani 1 1 d .
C7 C 0.9392(2) 1.01278(13) 0.79428(6) 0.0165(2) Uani 1 1 d .
H7A H 0.8254 1.0169 0.7511 0.020 Uiso 1 1 calc R
H7B H 1.0935 1.0118 0.7701 0.020 Uiso 1 1 calc R
C2 C 0.6681(2) 0.63303(14) 0.87802(7) 0.0229(3) Uani 1 1 d .
H2 H 0.5283 0.5754 0.8735 0.027 Uiso 1 1 calc R
C4 C 1.0433(2) 0.66002(14) 0.93355(7) 0.0222(2) Uani 1 1 d .
H4 H 1.1608 0.6216 0.9674 0.027 Uiso 1 1 calc R
C3 C 0.8382(2) 0.57746(13) 0.92774(7) 0.0228(3) Uani 1 1 d .
H3 H 0.8142 0.4827 0.9579 0.027 Uiso 1 1 calc R
O1 O 1.09978(14) 1.17263(10) 0.89893(5) 0.01864(17) Uani 1 1 d .
O2 O 0.67617(14) 1.17609(10) 0.95997(4) 0.01826(17) Uani 1 1 d .
O3 O 0.51323(14) 1.16780(12) 0.84007(5) 0.02314(19) Uani 1 1 d .
H1O H 1.058(3) 1.216(2) 0.9434(10) 0.033(4) Uiso 1 1 d .
H2O H 0.385(3) 1.171(2) 0.8657(9) 0.035(4) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C8 0.0120(5) 0.0177(4) 0.0146(4) 0.0004(4) 0.0003(4) -0.0004(4)
C1 0.0165(6) 0.0218(5) 0.0189(5) -0.0053(4) 0.0000(4) -0.0006(4)
C5 0.0161(5) 0.0193(5) 0.0202(5) -0.0012(4) 0.0001(5) -0.0004(4)
C9 0.0137(5) 0.0122(4) 0.0168(4) -0.0003(4) 0.0004(4) -0.0001(4)
C6 0.0170(6) 0.0174(5) 0.0130(4) -0.0037(3) 0.0030(4) 0.0004(4)
C7 0.0167(6) 0.0205(5) 0.0123(4) -0.0015(4) 0.0021(4) 0.0001(4)
C2 0.0203(6) 0.0210(5) 0.0274(6) -0.0066(4) 0.0056(5) -0.0049(4)
C4 0.0251(6) 0.0209(5) 0.0205(5) 0.0003(4) -0.0006(5) 0.0040(5)
C3 0.0296(7) 0.0162(5) 0.0224(5) -0.0008(4) 0.0086(5) -0.0002(4)
O1 0.0111(4) 0.0261(4) 0.0187(4) -0.0064(3) -0.0002(3) -0.0002(3)
O2 0.0157(4) 0.0235(4) 0.0156(3) -0.0025(3) 0.0026(3) -0.0008(3)
O3 0.0106(4) 0.0401(5) 0.0187(4) 0.0021(4) -0.0007(3) 0.0022(4)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C8 C9 110.25(8)
O1 C8 C7 109.18(8)
C9 C8 C7 112.06(9)
O1 C8 H8 108.4
C9 C8 H8 108.4
C7 C8 H8 108.4
C6 C1 C2 120.44(11)
C6 C1 H1 119.8
C2 C1 H1 119.8
C4 C5 C6 120.86(11)
C4 C5 H5 119.6
C6 C5 H5 119.6
O2 C9 O3 125.61(10)
O2 C9 C8 122.79(10)
O3 C9 C8 111.58(9)
C1 C6 C5 118.64(10)
C1 C6 C7 120.38(10)
C5 C6 C7 120.97(10)
C6 C7 C8 113.47(8)
C6 C7 H7A 108.9
C8 C7 H7A 108.9
C6 C7 H7B 108.9
C8 C7 H7B 108.9
H7A C7 H7B 107.7
C3 C2 C1 120.28(11)
C3 C2 H2 119.9
C1 C2 H2 119.9
C3 C4 C5 119.84(11)
C3 C4 H4 120.1
C5 C4 H4 120.1
C2 C3 C4 119.93(11)
C2 C3 H3 120.0
C4 C3 H3 120.0
C8 O1 H1O 111.5(12)
C9 O3 H2O 110.8(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C8 O1 1.4177(13)
C8 C9 1.5172(15)
C8 C7 1.5362(14)
C8 H8 1.0000
C1 C6 1.3923(16)
C1 C2 1.3955(16)
C1 H1 0.9500
C5 C4 1.3939(16)
C5 C6 1.3943(16)
C5 H5 0.9500
C9 O2 1.2100(13)
C9 O3 1.3158(13)
C6 C7 1.5143(14)
C7 H7A 0.9900
C7 H7B 0.9900
C2 C3 1.3825(19)
C2 H2 0.9500
C4 C3 1.3843(18)
C4 H4 0.9500
C3 H3 0.9500
O1 H1O 0.869(18)
O3 H2O 0.868(18)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H2O O1 0.868(18) 1.756(19) 2.6129(12) 168.4(16) 1_455
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
O1 C8 C9 O2 -0.92(14)
C7 C8 C9 O2 120.90(11)
O1 C8 C9 O3 177.72(9)
C7 C8 C9 O3 -60.45(11)
C2 C1 C6 C5 0.41(15)
C2 C1 C6 C7 -178.62(10)
C4 C5 C6 C1 -0.89(15)
C4 C5 C6 C7 178.14(10)
C1 C6 C7 C8 102.77(11)
C5 C6 C7 C8 -76.24(13)
O1 C8 C7 C6 67.95(11)
C9 C8 C7 C6 -54.48(12)
C6 C1 C2 C3 0.51(16)
C6 C5 C4 C3 0.44(16)
C1 C2 C3 C4 -0.97(17)
C5 C4 C3 C2 0.50(17)
