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#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/79/2017984.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_2017984
loop_
_publ_author_name
'Zakharov, Boris A.'
'Boldyreva, Elena V.'
_publ_section_title
;
 <small>DL</small>-Alaninium semi-oxalate monohydrate
;
_journal_coeditor_code           MX3041
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o47
_journal_page_last               o51
_journal_paper_doi               10.1107/S0108270110053655
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C3 H8 N O2 + , C2 H O4 - , H2 O'
_chemical_formula_moiety         'C3 H8 N O2 +, C2 H O4 -, H2 O'
_chemical_formula_sum            'C5 H11 N O7'
_chemical_formula_weight         197.15
_chemical_name_common            'DL-alaninium semi-oxalate hydrate'
_chemical_name_systematic
;
DL-Alaninium semioxalate monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.585(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4987(19)
_cell_length_b                   6.6017(6)
_cell_length_c                   11.3732(18)
_cell_measurement_reflns_used    4226
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      29.17
_cell_measurement_theta_min      1.78
_cell_volume                     860.0(2)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2006)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2006)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2006)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material
;
Mercury (Macrae et al., 2006), PLATON (Spek, 2009),
publCIF (Westrip, 2010)
and enCIFer (Allen et al., 2004)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and X-STEP32 (Stoe & Cie, 2000)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7933
_diffrn_reflns_theta_full        29.17
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.179
_refine_ls_extinction_coef       0.045(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0371
_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)+(0.0525P)²+0.0830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                1771
_reflns_number_total             2303
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            mx3041.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017984
_cod_database_fobs_code          2017984
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
O O3 0.07909(8) 0.70838(17) 0.44183(8) 0.0393(2) Uani d . 1 . .
H H3 0.047(2) 0.712(4) 0.346(3) 0.109(9) Uiso d . 1 . .
O O6 -0.00664(8) 0.78300(17) 0.69506(8) 0.0381(2) Uani d . 1 . .
O O4 -0.09365(8) 0.81046(16) 0.43677(8) 0.0386(2) Uani d . 1 . .
O O5 0.16786(8) 0.70784(17) 0.69763(8) 0.0404(3) Uani d . 1 . .
C C5 0.00674(10) 0.75948(18) 0.49414(10) 0.0264(2) Uani d . 1 . .
C C4 0.06276(10) 0.74937(18) 0.64295(10) 0.0271(2) Uani d . 1 . .
O O2 0.42083(9) 0.52827(17) 0.86114(11) 0.0497(3) Uani d . 1 . .
O O1 0.45614(9) 0.20394(16) 0.83206(11) 0.0460(3) Uani d . 1 . .
H H1 0.5151 0.2508 0.8275 0.086(8) Uiso calc R 1 . .
N N1 0.23091(9) 0.44368(17) 0.90592(10) 0.0333(2) Uani d . 1 . .
H H1A 0.2183 0.5408 0.8476 0.047(4) Uiso calc R 1 . .
H H1B 0.2756 0.4917 0.9832 0.050(5) Uiso calc R 1 . .
H H1C 0.1630 0.4025 0.9057 0.061(5) Uiso calc R 1 . .
C C1 0.39582(10) 0.3521(2) 0.85593(11) 0.0326(3) Uani d . 1 . .
C C2 0.29039(11) 0.2708(2) 0.87486(11) 0.0321(3) Uani d . 1 . .
H H2 0.2359(14) 0.214(2) 0.7917(15) 0.041(4) Uiso d . 1 . .
C C3 0.32156(15) 0.1097(3) 0.97869(16) 0.0499(4) Uani d . 1 . .
H H3A 0.2529 0.0722 0.9917 0.057(5) Uiso calc R 1 . .
H H3B 0.3791 0.1623 1.0572 0.079(7) Uiso calc R 1 . .
H H3C 0.3524 -0.0072 0.9527 0.071(6) Uiso calc R 1 . .
O O7 0.64997(9) 0.37273(18) 0.84316(10) 0.0404(2) Uani d . 1 . .
H H7A 0.7082(19) 0.313(3) 0.8303(19) 0.064(6) Uiso d . 1 . .
H H7B 0.625(2) 0.470(4) 0.784(3) 0.092(8) Uiso d . 1 . .
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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O3 H3 . . 116.3(15) ?
O4 C5 O3 . . 125.67(10) ?
O4 C5 C4 . . 121.26(10) ?
O3 C5 C4 . . 113.07(10) ?
O5 C4 O6 . . 126.78(10) ?
O5 C4 C5 . . 118.82(10) ?
O6 C4 C5 . . 114.40(10) ?
C1 O1 H1 . . 109.5 ?
C2 N1 H1A . . 109.5 ?
C2 N1 H1B . . 109.5 ?
H1A N1 H1B . . 109.5 ?
C2 N1 H1C . . 109.5 ?
H1A N1 H1C . . 109.5 ?
H1B N1 H1C . . 109.5 ?
O2 C1 O1 . . 124.49(12) ?
O2 C1 C2 . . 124.09(12) ?
O1 C1 C2 . . 111.41(11) ?
N1 C2 C1 . . 108.01(10) ?
N1 C2 C3 . . 110.57(10) ?
C1 C2 C3 . . 113.02(11) ?
N1 C2 H2 . . 107.5(9) ?
C1 C2 H2 . . 107.7(9) ?
C3 C2 H2 . . 109.9(10) ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
H7A O7 H7B . . 105(2) ?
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
O3 C5 . 1.3100(13) ?
O3 H3 . 1.00(3) ?
O6 C4 . 1.2507(13) ?
O4 C5 . 1.2075(14) ?
O5 C4 . 1.2385(14) ?
C5 C4 . 1.5527(15) ?
O2 C1 . 1.1994(17) ?
O1 C1 . 1.3278(16) ?
O1 H1 . 0.8200 ?
N1 C2 . 1.4799(17) ?
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
N1 H1C . 0.8900 ?
C1 C2 . 1.5158(17) ?
C2 C3 . 1.5199(19) ?
C2 H2 . 0.992(16) ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
O7 H7A . 0.89(2) ?
O7 H7B . 0.89(3) ?
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
N1 H1C O6 2_546 0.89 1.99 2.7794(14) 146.9
N1 H1C O4 2_546 0.89 2.36 3.0616(13) 135.7
N1 H1B O7 3_667 0.89 2.02 2.9034(15) 169.4
N1 H1A O5 . 0.89 1.91 2.7893(14) 167.5
O7 H7A O5 2_646 0.89(2) 1.84(2) 2.7257(14) 175.7(19)
O7 H7B O1 2_656 0.89(3) 2.02(3) 2.8976(16) 167(2)
O3 H3 O6 4_575 1.00(3) 1.57(3) 2.5732(13) 178(3)
O1 H1 O7 . 0.82 1.81 2.6234(14) 170.5
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
O4 C5 C4 O5 . . . . -175.78(12) ?
O3 C5 C4 O5 . . . . 4.11(17) ?
O4 C5 C4 O6 . . . . 5.08(18) ?
O3 C5 C4 O6 . . . . -175.03(11) ?
O2 C1 C2 N1 . . . . -2.64(17) ?
O1 C1 C2 N1 . . . . 177.80(10) ?
O2 C1 C2 C3 . . . . -125.29(15) ?
O1 C1 C2 C3 . . . . 55.14(15) ?
