#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/55/2015542.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_2015542
loop_
_publ_author_name
'K. Anitha'
'S. Athimoolam'
'S. Natarajan'
_publ_section_title
;
 <small>L</small>-Prolinium picrate and 2-methylpyridinium picrate
;
_journal_coeditor_code           DN3021
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o567
_journal_page_last               o570
_journal_paper_doi               10.1107/S0108270106029209
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C5 H10 N O2 + , C6 H2 N3 O7 -'
_chemical_formula_moiety         'C5 H10 N O2 + , C6 H2 N3 O7 -'
_chemical_formula_sum            'C11 H12 N4 O9'
_chemical_formula_weight         344.25
_chemical_name_common            'L-prolinium picrate'
_chemical_name_systematic
;
L-prolinium picrate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.142(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.909(4)
_cell_length_b                   5.352(3)
_cell_length_c                   12.474(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.20
_cell_measurement_theta_min      9.85
_cell_volume                     688.0(5)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;
ORTEP 3 for Windows (Farrugia, 1997), PLATON (Spek, 2003) and
MERCURY (Version 1.4.1; Macrae et al.,  2006)
;
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  SHELXTL/PC
_computing_structure_solution    'SHELXTL/PC (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius MACH3 sealed tube'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3719
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_meas      1.66
_exptl_crystal_density_method
'flotation using a liquid mixture of carbon tetrachloride and bromoform'
_exptl_crystal_description       needle
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2205
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0577
_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)+(0.1016P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1689
_reflns_number_gt                1590
_reflns_number_total             2205
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn3021.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2015542
_cod_database_fobs_code          2015542
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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 O1A 0.5965(3) 0.4460(5) 0.9635(2) 0.0504(7) Uani d . 1 . .
O O1B 0.4482(2) 0.2628(5) 0.8176(2) 0.0441(6) Uani d . 1 . .
H H1B 0.4118 0.3986 0.8119 0.066 Uiso calc R 1 . .
C C1 0.5557(3) 0.2674(6) 0.9041(3) 0.0305(6) Uani d . 1 B .
C C2 0.6275(3) 0.0212(6) 0.9191(3) 0.0342(6) Uani d D 1 . .
H H2 0.5666 -0.1190 0.9064 0.041 Uiso calc R 1 A 1
C C3 0.7083(3) 0.0030(10) 0.8391(3) 0.0474(9) Uani d PD 0.52 B 1
H H3A 0.6755 -0.1281 0.7834 0.057 Uiso calc PR 0.52 B 1
H H3B 0.7069 0.1599 0.7999 0.057 Uiso calc PR 0.52 B 1
C C4 0.8447(7) -0.0576(19) 0.9166(7) 0.0455(17) Uani d PD 0.52 B 1
H H4A 0.8584 -0.2370 0.9212 0.055 Uiso calc PR 0.52 B 1
H H4B 0.9086 0.0178 0.8878 0.055 Uiso calc PR 0.52 B 1
C C5 0.8560(3) 0.0392(18) 1.0229(4) 0.0767(19) Uani d PD 0.52 B 1
H H5A 0.8803 0.2142 1.0275 0.092 Uiso calc PR 0.52 B 1
H H5B 0.9211 -0.0516 1.0821 0.092 Uiso calc PR 0.52 B 1
N N1 0.7249(3) 0.0087(7) 1.0354(2) 0.0439(7) Uani d D 1 B .
H H1A 0.7196 -0.1393 1.0679 0.053 Uiso calc R 1 C 1
H H1C 0.7104 0.1312 1.0792 0.053 Uiso calc R 1 C 1
C C31 0.7083(3) 0.0030(10) 0.8391(3) 0.0474(9) Uani d PD 0.48 B 2
H H3C 0.7141 -0.1683 0.8158 0.057 Uiso calc PR 0.48 B 2
H H3D 0.6718 0.1059 0.7722 0.057 Uiso calc PR 0.48 B 2
C C41 0.8392(7) 0.100(2) 0.9115(7) 0.052(2) Uani d PD 0.48 B 2
H H41A 0.9072 0.0239 0.8881 0.062 Uiso calc PR 0.48 B 2
H H41B 0.8433 0.2793 0.9033 0.062 Uiso calc PR 0.48 B 2
C C51 0.8560(3) 0.0392(18) 1.0229(4) 0.0767(19) Uani d PD 0.48 B 2
H H5C 0.9037 0.1707 1.0728 0.092 Uiso calc PR 0.48 B 2
H H5D 0.9049 -0.1149 1.0433 0.092 Uiso calc PR 0.48 B 2
O O11 0.3453(2) 0.6864(5) 0.76837(19) 0.0387(6) Uani d . 1 . .
O O12 0.5313(2) 0.5462(7) 0.6679(2) 0.0537(8) Uani d . 1 . .
O O13 0.4166(3) 0.3670(6) 0.5124(3) 0.0625(8) Uani d . 1 . .
O O14 0.1507(3) 1.0047(9) 0.2598(2) 0.0617(9) Uani d . 1 . .
O O15 0.0693(3) 1.3017(9) 0.3313(3) 0.0742(11) Uani d . 1 . .
O O16 0.1150(3) 1.3073(6) 0.7175(3) 0.0636(9) Uani d . 1 . .
O O17 0.1876(3) 0.9980(7) 0.8269(2) 0.0541(8) Uani d . 1 . .
N N11 0.4326(2) 0.5253(6) 0.5860(3) 0.0380(6) Uani d . 1 . .
N N12 0.1304(3) 1.1055(7) 0.3397(3) 0.0453(8) Uani d . 1 . .
N N13 0.1659(2) 1.0970(6) 0.7365(3) 0.0393(7) Uani d . 1 . .
C C11 0.2968(3) 0.7829(6) 0.6720(3) 0.0287(6) Uani d . 1 . .
C C12 0.3281(3) 0.7069(6) 0.5727(3) 0.0318(6) Uani d . 1 . .
C C13 0.2725(3) 0.8005(7) 0.4665(3) 0.0347(7) Uani d . 1 . .
H H13 0.2942 0.7374 0.4056 0.042 Uiso calc R 1 . .
C C14 0.1825(3) 0.9922(7) 0.4508(3) 0.0351(7) Uani d . 1 . .
C C15 0.1499(3) 1.0857(7) 0.5400(3) 0.0359(7) Uani d . 1 . .
H H15 0.0919 1.2183 0.5289 0.043 Uiso calc R 1 . .
C C16 0.2034(3) 0.9823(6) 0.6460(3) 0.0308(6) Uani 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'
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 O1B H1B 109.5 ?
O1A C1 O1B 125.0(3) ?
O1A C1 C2 123.0(3) ?
O1B C1 C2 111.9(3) ?
N1 C2 C1 109.5(3) ?
N1 C2 C3 104.6(2) ?
C1 C2 C3 111.1(3) ?
N1 C2 H2 110.5 ?
C1 C2 H2 110.5 ?
C3 C2 H2 110.5 ?
C4 C3 C2 104.6(4) ?
C4 C3 H3A 110.8 ?
C2 C3 H3A 110.8 ?
C4 C3 H3B 110.8 ?
C2 C3 H3B 110.8 ?
H3A C3 H3B 108.9 ?
C5 C4 C3 106.8(5) ?
C5 C4 H4A 110.4 ?
C3 C4 H4A 110.4 ?
C5 C4 H4B 110.4 ?
C3 C4 H4B 110.4 ?
H4A C4 H4B 108.6 ?
C4 C5 N1 105.6(5) ?
C4 C5 H5A 110.6 ?
N1 C5 H5A 110.6 ?
C4 C5 H5B 110.6 ?
N1 C5 H5B 110.6 ?
H5A C5 H5B 108.7 ?
C2 N1 C5 107.1(3) y
C2 N1 H1A 110.3 ?
C5 N1 H1A 110.3 ?
C2 N1 H1C 110.3 ?
C5 N1 H1C 110.3 ?
H1A N1 H1C 108.6 ?
H41A C41 H41B 108.4 ?
O13 N11 O12 124.2(3) ?
O13 N11 C12 117.5(3) ?
O12 N11 C12 118.3(3) ?
O14 N12 O15 123.3(4) ?
O14 N12 C14 118.6(3) ?
O15 N12 C14 118.1(4) ?
O17 N13 O16 121.2(3) ?
O17 N13 C16 121.6(3) ?
O16 N13 C16 117.0(3) ?
O11 C11 C16 124.5(3) ?
O11 C11 C12 124.1(3) ?
C16 C11 C12 111.4(2) ?
C13 C12 C11 125.2(3) ?
C13 C12 N11 115.9(3) ?
C11 C12 N11 118.9(3) ?
C12 C13 C14 118.6(3) ?
C12 C13 H13 120.7 ?
C14 C13 H13 120.7 ?
C15 C14 C13 121.0(3) ?
C15 C14 N12 120.0(3) ?
C13 C14 N12 118.8(3) ?
C14 C15 C16 119.5(3) ?
C14 C15 H15 120.2 ?
C16 C15 H15 120.2 ?
C15 C16 C11 124.1(3) ?
C15 C16 N13 115.9(3) ?
C11 C16 N13 119.8(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C1 1.202(4) y
O1B C1 1.308(4) y
O1B H1B 0.8200 ?
C1 C2 1.513(4) ?
C2 N1 1.493(4) y
C2 C3 1.535(5) ?
C2 H2 0.9800 ?
C3 C4 1.520(8) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 C5 1.392(9) ?
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 N1 1.497(5) y
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
N1 H1A 0.9000 ?
N1 H1C 0.9000 ?
C41 H41A 0.9700 ?
C41 H41B 0.9700 ?
O11 C11 1.255(4) y
O12 N11 1.222(4) ?
O13 N11 1.219(4) ?
O14 N12 1.215(5) ?
O15 N12 1.229(5) ?
O16 N13 1.243(4) ?
O17 N13 1.197(4) ?
N11 C12 1.466(4) ?
N12 C14 1.448(4) ?
N13 C16 1.456(4) ?
C11 C16 1.438(4) ?
C11 C12 1.447(4) ?
C12 C13 1.359(5) ?
C13 C14 1.388(5) ?
C13 H13 0.9300 ?
C14 C15 1.370(5) ?
C15 C16 1.375(4) ?
C15 H15 0.9300 ?
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
O1B H1B O11 . 0.82 1.71 2.515(4) 165.3
N1 H1C O11 2_647 0.90 2.20 2.952(4) 140.9
N1 H1A O17 2_637 0.90 2.38 3.202(5) 152.8
N1 H1C O17 2_647 0.90 2.37 3.106(5) 139.2
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
O1A C1 C2 N1 19.1(5) y
O1B C1 C2 N1 -163.0(3) y
O1A C1 C2 C3 -95.9(4) ?
O1B C1 C2 C3 82.0(3) ?
N1 C2 C3 C4 8.2(6) y
C1 C2 C3 C4 126.2(5) ?
C2 C3 C4 C5 -27.1(8) y
C3 C4 C5 N1 34.7(9) y
C1 C2 N1 C5 -107.3(5) ?
C3 C2 N1 C5 11.8(5) y
C4 C5 N1 C2 -29.5(8) y
O11 C11 C12 C13 176.8(3) ?
C16 C11 C12 C13 -3.2(4) ?
O11 C11 C12 N11 -6.9(5) ?
C16 C11 C12 N11 173.1(3) ?
O13 N11 C12 C13 -42.6(4) y
O12 N11 C12 C13 135.4(3) ?
O13 N11 C12 C11 140.7(3) ?
O12 N11 C12 C11 -41.3(4) y
C11 C12 C13 C14 3.1(5) ?
N11 C12 C13 C14 -173.3(3) ?
C12 C13 C14 C15 -0.1(5) ?
C12 C13 C14 N12 175.3(3) ?
O14 N12 C14 C15 -173.0(3) ?
O15 N12 C14 C15 8.1(5) y
O14 N12 C14 C13 11.5(5) y
O15 N12 C14 C13 -167.4(3) ?
C13 C14 C15 C16 -2.4(5) ?
N12 C14 C15 C16 -177.8(3) ?
C14 C15 C16 C11 2.1(5) ?
C14 C15 C16 N13 178.5(3) ?
O11 C11 C16 C15 -179.5(3) ?
C12 C11 C16 C15 0.6(4) ?
O11 C11 C16 N13 4.2(5) ?
C12 C11 C16 N13 -175.8(3) ?
O17 N13 C16 C15 166.8(3) ?
O16 N13 C16 C15 -16.1(4) y
O17 N13 C16 C11 -16.6(5) y
O16 N13 C16 C11 160.5(3) ?
