#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/76/2207621.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_2207621
loop_
_publ_author_name
'He, Xiangjiu'
'Lobkovsky, Emil'
'Liu, Rui Hai'
_publ_section_title
;
 (R*)-Methyl 3-carboxy-2-hydroxypropanoate
;
_journal_coeditor_code           OM6268
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4104
_journal_page_last               o4106
_journal_paper_doi               10.1107/S1600536805036378
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C5 H8 O5'
_chemical_formula_moiety         'C5 H8 O5'
_chemical_formula_sum            'C5 H8 O5'
_chemical_formula_weight         148.11
_chemical_name_systematic
;
Methyl 3-carboxy-2-hydroxypropanoate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.415(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.699(5)
_cell_length_b                   4.1854(9)
_cell_length_c                   6.9782(15)
_cell_measurement_reflns_used    4381
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      34.26
_cell_measurement_theta_min      2.97
_cell_volume                     652.0(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6931
_diffrn_reflns_theta_full        34.31
_diffrn_reflns_theta_max         34.31
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9598
_exptl_absorpt_correction_T_min  0.9342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1421
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0589P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                1323
_reflns_number_total             1421
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om6268.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_sg_symbol_H-M      'C 2'
_cod_database_code               2207621
_cod_database_fobs_code          2207621
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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_occupancy
_atom_site_type_symbol
O1 0.25707(3) 0.9660(3) 0.24422(10) 0.03445(19) Uani d 1 O
H1 0.2392(8) 1.024(6) 0.117(3) 0.062(6) Uiso d 1 H
O2 0.30772(3) 0.6119(2) 0.10029(10) 0.03145(18) Uani d 1 O
O3 0.42670(3) 0.81550(17) 0.38465(10) 0.02544(15) Uani d 1 O
H3 0.4604(7) 0.745(4) 0.361(2) 0.038(4) Uiso d 1 H
O4 0.47584(3) 0.5139(2) 0.72298(10) 0.03141(18) Uani d 1 O
O5 0.38839(3) 0.28696(18) 0.73931(9) 0.02445(15) Uani d 1 O
C1 0.29831(3) 0.7457(2) 0.24497(11) 0.02159(17) Uani d 1 C
C2 0.33131(4) 0.6772(2) 0.44659(11) 0.02098(16) Uani d 1 C
H2A 0.3302(6) 0.868(4) 0.529(2) 0.032(4) Uiso d 1 H
H2B 0.3112(6) 0.506(4) 0.502(2) 0.029(3) Uiso d 1 H
C3 0.39473(4) 0.5632(2) 0.44873(12) 0.01953(15) Uani d 1 C
H3A 0.3960(6) 0.372(4) 0.3703(19) 0.020(3) Uiso d 1 H
C4 0.42474(3) 0.4564(2) 0.65146(11) 0.02063(16) Uani d 1 C
C5 0.41331(5) 0.1663(3) 0.93099(13) 0.0298(2) Uani d 1 C
H5A 0.4446(8) 0.013(5) 0.923(2) 0.045(4) Uiso d 1 H
H5B 0.3819(7) 0.062(5) 0.973(2) 0.041(4) Uiso d 1 H
H5C 0.4271(8) 0.341(6) 1.004(3) 0.049(5) Uiso d 1 H
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
O1 0.0340(3) 0.0493(5) 0.0185(3) 0.0170(4) 0.0006(2) 0.0034(3)
O2 0.0304(3) 0.0423(5) 0.0197(3) 0.0009(3) -0.0007(2) -0.0074(3)
O3 0.0214(3) 0.0247(3) 0.0319(3) 0.0025(2) 0.0093(2) 0.0084(3)
O4 0.0205(3) 0.0448(5) 0.0270(3) -0.0052(3) -0.0011(2) 0.0066(3)
O5 0.0230(3) 0.0318(4) 0.0174(2) -0.0045(3) 0.0007(2) 0.0049(2)
C1 0.0172(3) 0.0284(5) 0.0187(3) -0.0031(3) 0.0022(2) 0.0011(3)
C2 0.0178(3) 0.0285(4) 0.0160(3) 0.0008(3) 0.0013(2) 0.0009(3)
C3 0.0200(3) 0.0215(4) 0.0171(3) 0.0008(3) 0.0036(3) 0.0008(3)
C4 0.0192(3) 0.0231(4) 0.0194(3) 0.0001(3) 0.0031(3) 0.0008(3)
C5 0.0317(4) 0.0374(6) 0.0193(3) -0.0009(4) 0.0022(3) 0.0070(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
C1 O1 H1 111.8(13)
C3 O3 H3 109.3(11)
C4 O5 C5 116.39(7)
O2 C1 O1 123.81(8)
O2 C1 C2 124.26(9)
O1 C1 C2 111.92(7)
C1 C2 C3 112.51(7)
C1 C2 H2A 109.3(9)
C3 C2 H2A 111.9(8)
C1 C2 H2B 108.9(9)
C3 C2 H2B 106.2(9)
H2A C2 H2B 107.9(11)
O3 C3 C2 107.82(7)
O3 C3 C4 110.35(7)
C2 C3 C4 111.51(7)
O3 C3 H3A 111.8(8)
C2 C3 H3A 112.3(8)
C4 C3 H3A 103.1(8)
O4 C4 O5 123.54(8)
O4 C4 C3 124.29(8)
O5 C4 C3 112.16(7)
O5 C5 H5A 110.5(10)
O5 C5 H5B 105.1(10)
H5A C5 H5B 108.7(16)
O5 C5 H5C 106.0(13)
H5A C5 H5C 112.3(17)
H5B C5 H5C 113.9(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3133(12)
O1 H1 0.94(2)
O2 C1 1.2069(11)
O3 C3 1.3996(11)
O3 H3 0.864(16)
O4 C4 1.2014(11)
O5 C4 1.3199(11)
O5 C5 1.4459(11)
C1 C2 1.4973(12)
C2 C3 1.5142(12)
C2 H2A 0.986(18)
C2 H2B 0.966(15)
C3 C4 1.5221(11)
C3 H3A 0.973(15)
C5 H5A 0.966(18)
C5 H5B 0.926(17)
C5 H5C 0.91(2)
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 4 0.94(2) 1.73(2) 2.6527(11) 167.8(17)
O3 H3 O4 2_656 0.864(16) 1.917(16) 2.7663(11) 167.3(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21179973
