#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011919.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_2011919
loop_
_publ_author_name
'Subha Nandhini, M.'
'Krishnakumar, R. V.'
'Natarajan, S.'
_publ_section_title
;
 <small>L</small>-Prolinium tartrate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              423
_journal_page_last               424
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C5 H10 N O2 + , C4 H5 O6 -'
_chemical_formula_moiety         'C5 H10 N O2 + , C4 H5 O6 -'
_chemical_formula_sum            'C9 H15 N O8'
_chemical_formula_weight         267.24
_chemical_name_common            'L-prolinium tartrate'
_chemical_name_systematic
;
 L-prolinium 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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 100.40(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0070(10)
_cell_length_b                   17.676(3)
_cell_length_c                   6.5230(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      16
_cell_volume                     567.83(18)
_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    'SHELXS93 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .921
_diffrn_measured_fraction_theta_max .921
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  .018
_diffrn_reflns_av_sigmaI/netI    .009
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1077
_diffrn_reflns_theta_full        67.90
_diffrn_reflns_theta_max         67.9
_diffrn_reflns_theta_min         5.0
_diffrn_standards_decay_%        .1
_diffrn_standards_interval_count 200
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.207
_exptl_absorpt_correction_T_max  .734
_exptl_absorpt_correction_T_min  .540
_exptl_absorpt_correction_type   \y-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      1.55
_exptl_crystal_density_method    flotation
_exptl_crystal_description       needles
_exptl_crystal_F_000             284
_exptl_crystal_size_max          .42
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .21
_refine_diff_density_max         .160
_refine_diff_density_min         -.179
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   .1(3)
_refine_ls_extinction_coef       .060(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         974
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          .0276
_refine_ls_R_factor_gt           .0275
_refine_ls_shift/su_max          .000
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.1468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0736
_reflns_number_gt                968
_reflns_number_total             974
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    vj1124.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  P21
_cod_original_cell_volume        567.8(2)
_cod_database_code               2011919
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 .8186(4) .47409(14) .7398(4) .0494(6) Uani d . 1 . . O
H1 .9601 .4948 .7945 .074 Uiso calc R 1 . . H
O2 1.0870(4) .37594(16) .7105(4) .0626(8) Uani d . 1 . . O
O3 .9331(3) .60674(11) .4467(3) .0341(4) Uani d . 1 . . O
H11 1.0595 .6186 .5395 .051 Uiso calc R 1 . . H
O4 .7627(3) .71715(10) .5289(3) .0313(4) Uani d . 1 . . O
O5 .3369(3) .70372(10) .2185(3) .0293(4) Uani d . 1 . . O
H13 .1876 .6900 .1563 .044 Uiso calc R 1 . . H
O6 .7794(3) .67500(11) -.0068(3) .0323(5) Uani d . 1 . . O
H15 .7437 .6800 -.1338 .048 Uiso calc R 1 . . H
O7 .3422(4) .63018(12) -.2814(3) .0364(5) Uani d . 1 . . O
O8 .2251(4) .54422(12) -.0614(3) .0412(5) Uani d . 1 . . O
N1 .7154(4) .30306(13) .4339(3) .0333(5) Uani d . 1 . . N
H9 .8876 .2911 .4906 .040 Uiso calc R 1 . . H
H10 .6082 .2636 .4513 .040 Uiso calc R 1 . . H
C1 .8727(5) .40807(17) .6720(4) .0335(6) Uani d . 1 . . C
C2 .6270(5) .37223(16) .5379(4) .0320(6) Uani d . 1 . . C
H2 .4946 .3580 .6249 .038 Uiso calc R 1 . . H
C3 .4903(7) .4213(2) .3576(5) .0559(9) Uani d . 1 . . C
H3 .2993 .4087 .3182 .067 Uiso calc R 1 A 1 H
H4 .5075 .4745 .3933 .067 Uiso calc R 1 A 1 H
C4 .6384(12) .4030(3) .1897(8) .0509(17) Uani d P .711(13) B 1 C
H5 .8067 .4314 .2060 .061 Uiso calc PR .711(13) B 1 H
H6 .5295 .4150 .0551 .061 Uiso calc PR .711(13) B 1 H
C4' .468(3) .3750(7) .1615(17) .049(4) Uani d P .289(13) B 2 C
H5' .2944 .3490 .1313 .059 Uiso calc PR .289(13) B 2 H
H6' .4868 .4067 .0436 .059 Uiso calc PR .289(13) B 2 H
C5 .6948(8) .3199(2) .2070(5) .0480(8) Uani d . 1 . . C
H7 .8632 .3078 .1607 .058 Uiso calc R 1 C 1 H
H8 .5484 .2913 .1244 .058 Uiso calc R 1 C 1 H
C6 .7511(5) .65955(14) .4242(3) .0240(5) Uani d . 1 . . C
C7 .5137(4) .64074(14) .2524(3) .0231(5) Uani d . 1 . . C
H12 .4142 .5982 .2990 .028 Uiso calc R 1 . . H
C8 .6173(5) .61642(14) .0548(3) .0245(5) Uani d . 1 . . C
H14 .7310 .5714 .0875 .029 Uiso calc R 1 . . H
C9 .3727(5) .59527(14) -.1118(4) .0261(5) 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 .0382(10) .0446(14) .0639(15) -.0046(10) .0054(10) -.0201(11)
O2 .0307(10) .0664(17) .0847(19) .0062(11) -.0059(11) -.0291(15)
O3 .0312(9) .0383(11) .0273(9) .0072(8) -.0098(7) -.0052(8)
O4 .0313(8) .0329(11) .0273(9) -.0030(7) -.0009(7) -.0081(7)
O5 .0254(8) .0306(10) .0291(9) .0044(7) -.0024(7) -.0028(7)
O6 .0281(8) .0440(11) .0233(8) -.0089(8) .0008(6) .0010(8)
O7 .0311(9) .0501(13) .0242(10) -.0035(8) -.0056(7) .0033(8)
O8 .0445(11) .0392(12) .0359(11) -.0141(9) -.0034(8) -.0027(8)
N1 .0336(10) .0260(13) .0394(12) -.0031(9) .0041(9) .0015(9)
C1 .0279(12) .0396(16) .0343(14) -.0026(11) .0091(10) -.0029(12)
C2 .0271(11) .0308(15) .0377(15) .0014(11) .0048(10) -.0014(11)
C3 .0598(18) .041(2) .059(2) .0145(15) -.0113(15) -.0005(15)
C4 .057(4) .046(3) .044(3) -.006(3) -.006(2) .017(2)
C4' .063(9) .036(7) .039(7) -.006(6) -.016(5) .004(5)
C5 .060(2) .047(2) .0356(16) -.0045(15) .0050(14) -.0038(13)
C6 .0247(10) .0272(14) .0192(11) -.0030(9) .0017(8) .0021(9)
C7 .0224(10) .0254(12) .0198(12) -.0016(9) -.0004(8) -.0006(9)
C8 .0241(10) .0257(13) .0216(12) .0008(9) -.0013(9) -.0017(9)
C9 .0246(11) .0269(14) .0250(13) .0001(10) .0002(9) -.0061(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 '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 109.5
C6 O3 H11 109.5
C7 O5 H13 109.5
C8 O6 H15 109.5
C5 N1 C2 108.1(2)
C5 N1 H9 110.1
C2 N1 H9 110.1
C5 N1 H10 110.1
C2 N1 H10 110.1
H9 N1 H10 108.4
O2 C1 O1 126.1(3)
O2 C1 C2 121.7(3)
O1 C1 C2 112.1(2)
N1 C2 C1 109.1(2)
N1 C2 C3 104.0(2)
C1 C2 C3 114.4(3)
N1 C2 H2 109.7
C1 C2 H2 109.7
C3 C2 H2 109.7
C4 C3 C4' 38.3(5)
C4 C3 C2 103.6(3)
C4' C3 C2 107.5(5)
C4 C3 H3 111.1
C4' C3 H3 74.4
C2 C3 H3 111.1
C4 C3 H4 111.1
C4' C3 H4 136.2
C2 C3 H4 111.1
H3 C3 H4 109.0
C3 C4 C5 105.9(4)
C3 C4 H5 110.5
C5 C4 H5 110.5
C3 C4 H6 110.5
C5 C4 H6 110.5
H5 C4 H6 108.7
C5 C4' C3 104.4(7)
C5 C4' H5' 110.9
C3 C4' H5' 110.9
C5 C4' H6' 110.9
C3 C4' H6' 110.9
H5' C4' H6' 108.9
C4' C5 C4 38.2(5)
C4' C5 N1 104.0(5)
C4 C5 N1 104.4(3)
C4' C5 H7 139.4
C4 C5 H7 110.9
N1 C5 H7 110.9
C4' C5 H8 75.9
C4 C5 H8 110.9
N1 C5 H8 110.9
H7 C5 H8 108.9
O4 C6 O3 125.2(2)
O4 C6 C7 123.2(2)
O3 C6 C7 111.6(2)
O5 C7 C6 109.15(19)
O5 C7 C8 112.70(19)
C6 C7 C8 110.09(17)
O5 C7 H12 108.3
C6 C7 H12 108.3
C8 C7 H12 108.3
O6 C8 C9 113.78(18)
O6 C8 C7 109.32(19)
C9 C8 C7 108.45(17)
O6 C8 H14 108.4
C9 C8 H14 108.4
C7 C8 H14 108.4
O8 C9 O7 127.3(2)
O8 C9 C8 115.2(2)
O7 C9 C8 117.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.294(4)
O1 H1 .8200
O2 C1 1.200(4)
O3 C6 1.294(3)
O3 H11 .8200
O4 C6 1.221(3)
O5 C7 1.415(3)
O5 H13 .8200
O6 C8 1.418(3)
O6 H15 .8200
O7 C9 1.252(3)
O8 C9 1.248(3)
N1 C5 1.495(4)
N1 C2 1.503(3)
N1 H9 .9000
N1 H10 .9000
C1 C2 1.513(4)
C2 C3 1.521(4)
C2 H2 .9800
C3 C4 1.465(6)
C3 C4' 1.505(12)
C3 H3 .9700
C3 H4 .9700
C4 C5 1.495(6)
C4 H5 .9700
C4 H6 .9700
C4' C5 1.484(13)
C4' H5' .9700
C4' H6' .9700
C5 H7 .9700
C5 H8 .9700
C6 C7 1.516(3)
C7 C8 1.535(3)
C7 H12 .9800
C8 C9 1.530(3)
C8 H14 .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 O8 1_656 .82 1.72 2.531(3) 170.3
N1 H9 O4 2_746 .90 2.21 2.994(3) 145.7
N1 H10 O4 2_646 .90 2.06 2.881(3) 152.1
O3 H11 O7 1_656 .82 1.68 2.490(2) 170.8
O5 H13 O6 1_455 .82 2.14 2.954(2) 169.8
O6 H15 O4 1_554 .82 2.31 3.105(3) 162.2
C2 H2 O2 1_455 .98 2.23 3.112(3) 148.5
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
C5 N1 C2 C1 -108.9(3)
C5 N1 C2 C3 13.7(3)
O2 C1 C2 N1 -11.8(4)
O1 C1 C2 N1 169.8(2)
O2 C1 C2 C3 -127.8(3)
O1 C1 C2 C3 53.8(3)
N1 C2 C3 C4 -31.6(4)
C1 C2 C3 C4 87.4(4)
N1 C2 C3 C4' 8.1(7)
C1 C2 C3 C4' 127.0(7)
C4' C3 C4 C5 -63.1(8)
C2 C3 C4 C5 38.2(5)
C4 C3 C4' C5 63.0(8)
C2 C3 C4' C5 -26.7(10)
C3 C4' C5 C4 -61.1(8)
C3 C4' C5 N1 34.5(9)
C3 C4 C5 C4' 65.0(8)
C3 C4 C5 N1 -29.5(5)
C2 N1 C5 C4' -30.4(7)
C2 N1 C5 C4 9.0(4)
O4 C6 C7 O5 7.8(3)
O3 C6 C7 O5 -173.38(18)
O4 C6 C7 C8 132.0(2)
O3 C6 C7 C8 -49.2(3)
O5 C7 C8 O6 64.7(2)
C6 C7 C8 O6 -57.4(2)
O5 C7 C8 C9 -59.9(2)
C6 C7 C8 C9 178.0(2)
O6 C8 C9 O8 -179.5(2)
C7 C8 C9 O8 -57.6(3)
O6 C8 C9 O7 .6(3)
C7 C8 C9 O7 122.5(2)