#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/12/2201238.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_2201238
loop_
_publ_author_name
'K. Rajagopal'
'M. Subha Nandhini'
'R. V. Krishnakumar'
'S. Natarajan'
_publ_section_title
;
 <small>L</small>-Alaninium tartrate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1306
_journal_page_last               o1308
_journal_paper_doi               10.1107/S1600536802019414
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C3 H8 N O2 1+, C4 H5 O6 1-'
_chemical_formula_sum            'C7 H13 N O8'
_chemical_formula_weight         239.18
_chemical_name_common            'L-alaninium tartrate'
_chemical_name_systematic
;
L-alaninium tartrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(10)
_cell_angle_beta                 98.090(10)
_cell_angle_gamma                90.000(10)
_cell_formula_units_Z            2
_cell_length_a                   5.1446(8)
_cell_length_b                   13.721(3)
_cell_length_c                   7.4751(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.75
_cell_volume                     522.41(15)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_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  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1061
_diffrn_reflns_theta_full        24.96
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 200
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al. 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      1.53
_exptl_crystal_density_method
'flotation in a mixture of xylene and carbon tetrachloride'
_exptl_crystal_description       plates
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.298
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.1(19)
_refine_ls_extinction_coef       0.045(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         954
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0436
_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)+(0.0848P)²+0.1960P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                944
_reflns_number_total             954
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6018.cif
_cod_data_source_block           I
_cod_original_cell_volume        522.42(14)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2201238
_cod_database_fobs_code          2201238
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.1688(6) 0.5120(3) 0.7325(4) 0.0490(9) Uani d . 1 . . O
H1 0.1520 0.4853 0.8283 0.074 Uiso calc R 1 . . H
O2 0.5462(5) 0.5643(2) 0.8841(4) 0.0434(7) Uani d . 1 . . O
O3 0.1891(5) 0.8233(2) 1.3666(3) 0.0371(7) Uani d . 1 . . O
H3 0.1219 0.8269 1.4595 0.056 Uiso calc R 1 . . H
O4 -0.1330(6) 0.7148(3) 1.2868(3) 0.0459(8) Uani d . 1 . . O
O5 -0.0059(5) 0.6910(2) 0.9597(3) 0.0355(6) Uani d . 1 . . O
H5 -0.1203 0.6687 1.0140 0.053 Uiso calc R 1 . . H
O6 -0.1078(5) 0.90422(19) 0.9821(3) 0.0306(6) Uani d . 1 . . O
H6 -0.2144 0.8816 0.9008 0.046 Uiso calc R 1 . . H
O7 0.4473(4) 0.8258(2) 0.7834(3) 0.0330(6) Uani d . 1 . . O
O8 0.0315(4) 0.8467(2) 0.6604(3) 0.0329(6) Uani d . 1 . . O
N1 0.6550(6) 0.6760(2) 0.6067(4) 0.0314(7) Uani d . 1 . . N
H1A 0.6216 0.7198 0.6883 0.047 Uiso calc R 1 . . H
H1B 0.6782 0.7063 0.5048 0.047 Uiso calc R 1 . . H
H1C 0.7998 0.6431 0.6488 0.047 Uiso calc R 1 . . H
C1 0.3949(7) 0.5587(3) 0.7495(5) 0.0305(8) Uani d . 1 . . C
C2 0.4315(8) 0.6077(3) 0.5704(5) 0.0354(8) Uani d . 1 . . C
H2A 0.2729 0.6452 0.5277 0.042 Uiso calc R 1 . . H
C3 0.4727(13) 0.5341(4) 0.4281(7) 0.0680(18) Uani d . 1 . . C
H3A 0.4944 0.5673 0.3181 0.102 Uiso calc R 1 . . H
H3B 0.3230 0.4918 0.4070 0.102 Uiso calc R 1 . . H
H3C 0.6270 0.4964 0.4683 0.102 Uiso calc R 1 . . H
C4 0.0555(6) 0.7650(3) 1.2559(4) 0.0262(7) Uani d . 1 . . C
C5 0.1493(6) 0.7578(3) 1.0720(4) 0.0256(7) Uani d . 1 . . C
H5A 0.3315 0.7349 1.0893 0.031 Uiso calc R 1 . . H
C6 0.1387(6) 0.8580(2) 0.9813(4) 0.0217(7) Uani d . 1 . . C
H6A 0.2735 0.8992 1.0496 0.026 Uiso calc R 1 . . H
C7 0.2117(6) 0.8436(2) 0.7923(4) 0.0215(6) 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
O1 0.0533(18) 0.060(2) 0.0355(15) -0.0295(16) 0.0111(12) 0.0073(14)
O2 0.0405(15) 0.0521(17) 0.0370(15) -0.0132(13) 0.0031(12) 0.0158(13)
O3 0.0431(13) 0.0515(17) 0.0194(11) -0.0106(13) 0.0135(10) -0.0046(12)
O4 0.0540(16) 0.058(2) 0.0300(13) -0.0215(15) 0.0212(12) -0.0022(12)
O5 0.0498(14) 0.0334(13) 0.0255(13) -0.0115(12) 0.0129(11) -0.0048(11)
O6 0.0291(12) 0.0371(14) 0.0274(12) 0.0068(10) 0.0105(9) -0.0082(11)
O7 0.0269(12) 0.0476(16) 0.0269(11) 0.0013(11) 0.0127(9) -0.0042(11)
O8 0.0300(12) 0.0512(16) 0.0191(11) 0.0002(12) 0.0085(9) -0.0020(11)
N1 0.0354(14) 0.0376(16) 0.0244(13) -0.0106(13) 0.0154(11) 0.0011(12)
C1 0.0336(18) 0.0248(16) 0.0356(18) -0.0061(14) 0.0137(14) 0.0002(15)
C2 0.039(2) 0.0349(19) 0.0329(18) -0.0091(16) 0.0083(14) 0.0035(15)
C3 0.110(5) 0.056(3) 0.045(3) -0.043(3) 0.037(3) -0.020(2)
C4 0.0292(15) 0.0302(16) 0.0204(15) 0.0014(15) 0.0075(12) 0.0054(14)
C5 0.0282(15) 0.0313(18) 0.0179(14) 0.0009(14) 0.0055(11) -0.0005(14)
C6 0.0209(14) 0.0261(15) 0.0193(14) -0.0006(12) 0.0072(11) -0.0040(12)
C7 0.0260(15) 0.0202(14) 0.0201(14) -0.0028(13) 0.0093(11) -0.0013(12)
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'
N N 0.0061 0.0033 '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_publ_flag
C1 O1 H1 109.5 ?
C4 O3 H3 109.5 ?
C5 O5 H5 109.5 ?
C6 O6 H6 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 125.4(3) yes
O2 C1 C2 124.5(3) yes
O1 C1 C2 110.1(3) yes
N1 C2 C3 111.9(4) yes
N1 C2 C1 107.8(3) yes
C3 C2 C1 111.8(4) yes
N1 C2 H2A 108.4 ?
C3 C2 H2A 108.4 ?
C1 C2 H2A 108.4 ?
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 ?
O4 C4 O3 126.2(3) ?
O4 C4 C5 119.3(3) ?
O3 C4 C5 114.5(3) ?
O5 C5 C4 110.8(3) ?
O5 C5 C6 109.7(2) ?
C4 C5 C6 110.2(3) ?
O5 C5 H5A 108.7 ?
C4 C5 H5A 108.7 ?
C6 C5 H5A 108.7 ?
O6 C6 C7 113.5(2) ?
O6 C6 C5 112.1(3) ?
C7 C6 C5 107.2(3) ?
O6 C6 H6A 107.9 ?
C7 C6 H6A 107.9 ?
C5 C6 H6A 107.9 ?
O7 C7 O8 125.5(3) yes
O7 C7 C6 116.3(3) ?
O8 C7 C6 118.2(3) ?
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
O1 C1 . 1.319(5) yes
O1 H1 . 0.8200 ?
O2 C1 . 1.185(5) yes
O3 C4 . 1.279(4) ?
O3 H3 . 0.8200 ?
O4 C4 . 1.238(4) yes
O5 C5 . 1.412(4) ?
O5 H5 . 0.8200 ?
O6 C6 . 1.418(4) ?
O6 H6 . 0.8200 ?
O7 C7 . 1.247(4) yes
O8 C7 . 1.256(4) yes
N1 C2 . 1.479(5) yes
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
N1 H1C . 0.8900 ?
C1 C2 . 1.533(5) yes
C2 C3 . 1.503(6) yes
C2 H2A . 0.9800 ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 C5 . 1.522(4) ?
C5 C6 . 1.530(5) ?
C5 H5A . 0.9800 ?
C6 C7 . 1.525(4) ?
C6 H6A . 0.9800 ?
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 O6 2_547 0.82 1.84 2.651(4) 169
O6 H6 O7 1_455 0.82 1.99 2.765(4) 158
O5 H5 O4 . 0.82 2.15 2.639(3) 119
O5 H5 O2 1_455 0.82 2.34 2.878(4) 124
O3 H3 O8 1_556 0.82 1.66 2.466(3) 170
N1 H1A O7 . 0.89 1.90 2.740(4) 157
N1 H1C O5 1_655 0.89 2.49 2.958(4) 114
N1 H1B O4 1_654 0.89 2.01 2.815(4) 149
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
_geom_torsion_publ_flag
O2 C1 C2 N1 -10.8(5) yes
O1 C1 C2 N1 167.7(3) yes
O2 C1 C2 C3 112.5(5) yes
O1 C1 C2 C3 -69.0(5) yes
O4 C4 C5 O5 0.4(4) yes
O3 C4 C5 O5 179.0(3) ?
O4 C4 C5 C6 122.0(4) ?
O3 C4 C5 C6 -59.3(4) ?
O5 C5 C6 O6 72.3(3) ?
C4 C5 C6 O6 -49.9(3) ?
O5 C5 C6 C7 -52.9(3) ?
C4 C5 C6 C7 -175.1(2) yes
O6 C6 C7 O7 163.2(3) ?
C5 C6 C7 O7 -72.5(3) ?
O6 C6 C7 O8 -19.5(4) yes
C5 C6 C7 O8 104.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654663
