#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/51/1505188.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_1505188
loop_
_publ_author_name
'Wenger, Mazal'
'Bernstein, Joel'
_publ_section_title
;
 Cocrystal Design Gone Awry? A New Dimorphic Hydrate of Oxalic Acid
;
_journal_issue                   3
_journal_name_full               'Molecular Pharmaceutics'
_journal_page_first              355
_journal_paper_doi               10.1021/mp070006w
_journal_volume                  4
_journal_year                    2007
_chemical_formula_sum            'C4 H9 O11'
_chemical_formula_weight         233.11
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.345(10)
_cell_angle_beta                 100.244(9)
_cell_angle_gamma                97.674(11)
_cell_formula_units_Z            2
_cell_length_a                   6.337(2)
_cell_length_b                   7.247(3)
_cell_length_c                   10.571(4)
_cell_measurement_temperature    273(2)
_cell_volume                     471.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4158
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.174
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             242
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0916P)²+0.1363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1514
_reflns_number_gt                1880
_reflns_number_total             2343
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            mp070006wsi20070111_042846.cif
_cod_data_source_block           mw018_1
_cod_database_code               1505188
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
H152 H 0.253(5) 0.219(4) 0.213(3) 0.038(7) Uiso 0.80 1 d P
O4 O 0.3331(2) 0.66211(18) 0.64865(12) 0.0365(3) Uani 1 1 d .
O2 O 0.2382(2) 0.39080(17) 0.52241(12) 0.0369(3) Uani 1 1 d .
O6 O 0.6614(2) 0.66483(18) 0.93200(11) 0.0325(3) Uani 1 1 d .
O5 O 0.3420(2) 0.49050(19) 0.84608(12) 0.0355(3) Uani 1 1 d .
O3 O 0.2732(2) 0.84605(18) 0.43250(12) 0.0360(3) Uani 1 1 d .
O1 O 0.1839(3) 0.56966(18) 0.31372(12) 0.0398(4) Uani 1 1 d .
O9 O 0.0561(2) 0.7466(2) 0.12563(14) 0.0444(4) Uani 1 1 d .
C1 C 0.2445(3) 0.6763(2) 0.42199(15) 0.0247(3) Uani 1 1 d .
C2 C 0.2750(3) 0.5637(2) 0.54186(15) 0.0250(3) Uani 1 1 d .
C3 C 0.5070(3) 0.5476(2) 0.93704(15) 0.0247(3) Uani 1 1 d .
O11 O 0.2317(2) 0.0715(2) 0.64553(13) 0.0322(3) Uani 1 1 d .
O7 O 0.2382(2) -0.0979(2) 0.92387(12) 0.0347(3) Uani 1 1 d .
O8 O 0.4984(2) 0.0769(2) 0.84782(12) 0.0347(3) Uani 1 1 d .
C4 C 0.4184(3) -0.0094(2) 0.93572(15) 0.0255(3) Uani 1 1 d .
O10 O 0.1588(3) 0.1559(2) 0.27580(15) 0.0426(4) Uani 1 1 d .
H2 H 0.242(5) 0.179(5) 0.618(3) 0.060(8) Uiso 1 1 d .
H1 H 0.249(4) 0.008(4) 0.590(3) 0.046(8) Uiso 1 1 d .
H5 H 0.143(5) 0.644(4) 0.238(3) 0.054(7) Uiso 1 1 d .
H6 H 0.118(6) 0.783(5) 0.060(3) 0.071(9) Uiso 1 1 d .
H8 H 0.393(5) 0.069(4) 0.764(3) 0.064(9) Uiso 1 1 d .
H9 H 0.343(6) 0.570(5) 0.764(3) 0.078(10) Uiso 1 1 d .
H18 H 0.195(5) 0.263(4) 0.352(3) 0.034(7) Uiso 0.80 1 d P
H17 H 0.000(5) 0.118(4) 0.215(3) 0.036(8) Uiso 0.75 1 d P
H7 H -0.058(6) 0.708(4) 0.087(3) 0.063(9) Uiso 1 1 d .
H15 H 0.202(5) 0.032(5) 0.313(3) 0.033(8) Uiso 0.65 1 d P
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
_geom_angle_site_symmetry_3
C2 O4 H9 118.1(13) .
C3 O5 H9 112.4(18) .
C1 O1 H5 112.0(16) .
H6 O9 H7 98(3) .
O3 C1 O1 125.22(14) .
O3 C1 C2 121.85(15) .
O1 C1 C2 112.93(14) .
O2 C2 O4 127.62(15) .
O2 C2 C1 117.55(14) .
O4 C2 C1 114.82(14) .
O6 C3 O5 126.50(14) .
O6 C3 C3 120.58(18) 2_667
O5 C3 C3 112.92(17) 2_667
H2 O11 H1 104(3) .
H2 O11 H8 111(2) .
H1 O11 H8 113(2) .
C4 O8 H8 113.2(17) .
O7 C4 O8 126.74(15) .
O7 C4 C4 121.03(18) 2_657
O8 C4 C4 112.22(17) 2_657
H152 O10 H18 99(2) .
H152 O10 H17 103(2) .
H18 O10 H17 123(2) .
H152 O10 H15 118(3) .
H18 O10 H15 108(2) .
H17 O10 H15 106(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 C2 1.257(2) .
O4 H9 1.43(4) .
O2 C2 1.238(2) .
O6 C3 1.219(2) .
O5 C3 1.287(2) .
O5 H9 1.08(4) .
O3 C1 1.213(2) .
O1 C1 1.298(2) .
O1 H5 1.02(3) .
O9 H6 0.90(4) .
O9 H7 0.77(3) .
C1 C2 1.556(2) .
C3 C3 1.556(3) 2_667
O11 H2 0.85(3) .
O11 H1 0.75(3) .
O11 H8 1.47(3) .
O7 C4 1.213(2) .
O8 C4 1.297(2) .
O8 H8 1.00(3) .
C4 C4 1.539(3) 2_657
O10 H152 1.06(3) .
O10 H18 1.05(3) .
O10 H17 1.08(3) .
O10 H15 1.06(4) .
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
O3 C1 C2 O2 178.61(17)
O1 C1 C2 O2 -0.5(2)
O3 C1 C2 O4 -0.7(2)
O1 C1 C2 O4 -179.83(16)
