#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/61/2206130.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_2206130
loop_
_publ_author_name
'A. Aarthy'
'K. Anitha'
'S. Athimoolam'
'S. Asath Bahadur'
'R.K. Rajaram'
_publ_section_title
;
 <small>L</small>-Asparaginium nitrate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2042
_journal_page_last               o2044
_journal_paper_doi               10.1107/S1600536805017496
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C4 H9 N O3 + N O3 -'
_chemical_formula_moiety         'C4 H9 N O3 + N O3 -'
_chemical_formula_sum            'C4 H9 N3 O6'
_chemical_formula_weight         195.14
_chemical_name_common            'L-Asparaginium Nitrate'
_chemical_name_systematic
;
L-Asparaginium nitrate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_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                96.88(3)
_cell_angle_beta                 104.47(3)
_cell_angle_gamma                102.11(3)
_cell_formula_units_Z            2
_cell_length_a                   5.357(2)
_cell_length_b                   8.232(3)
_cell_length_c                   10.172(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.03
_cell_measurement_theta_min      9.78
_cell_volume                     417.6(3)
_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    'SHELXTL/PC (Bruker, 2000)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1988
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.8456
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      1.545
_exptl_crystal_density_method
'Flotation using a liquid mixture of xylene and CCl~4~'
_exptl_crystal_description       Block
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.417
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         1474
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1565P)²+0.0806P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1891
_reflns_number_gt                1358
_reflns_number_total             1474
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6674.cif
_cod_data_source_block           I
_cod_original_cell_volume        417.5(3)
_cod_database_code               2206130
_cod_database_fobs_code          2206130
loop_
_symmetry_equiv_pos_as_xyz
'x, y, 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_type_symbol
O1A 0.4194(11) 0.5897(7) 0.2028(5) 0.0559(13) Uani d . 1 O
O1B 0.5712(10) 0.4086(6) 0.3287(5) 0.0463(11) Uani d . 1 O
H1B 0.6496 0.3945 0.2702 0.069 Uiso calc R 1 H
C11 0.4456(11) 0.5254(7) 0.3041(6) 0.0350(12) Uani d . 1 C
C12 0.3249(10) 0.5801(7) 0.4178(5) 0.0308(11) Uani d . 1 C
H12 0.1308 0.5504 0.3797 0.037 Uiso calc R 1 H
N11 0.3933(10) 0.4922(6) 0.5355(5) 0.0376(11) Uani d . 1 N
H11A 0.3179 0.3821 0.5085 0.056 Uiso calc R 1 H
H11B 0.3339 0.5330 0.6036 0.056 Uiso calc R 1 H
H11C 0.5693 0.5088 0.5654 0.056 Uiso calc R 1 H
C13 0.4199(13) 0.7707(7) 0.4688(6) 0.0403(13) Uani d . 1 C
H13A 0.3643 0.8000 0.5504 0.048 Uiso calc R 1 H
H13B 0.6128 0.8043 0.4943 0.048 Uiso calc R 1 H
C14 0.3085(12) 0.8651(7) 0.3593(6) 0.0361(12) Uani d . 1 C
N12 0.4745(12) 0.9956(7) 0.3397(7) 0.0517(14) Uani d . 1 N
H12A 0.4182 1.0551 0.2801 0.062 Uiso calc R 1 H
H12B 0.6396 1.0217 0.3865 0.062 Uiso calc R 1 H
O1C 0.0656(9) 0.8199(5) 0.2948(5) 0.0448(10) Uani d . 1 O
O2A 1.2159(9) 0.0990(6) 0.0883(5) 0.0445(10) Uani d . 1 O
O2B 0.8322(8) -0.0600(5) 0.1003(4) 0.0407(10) Uani d . 1 O
H2B 0.9297 -0.0870 0.1655 0.061 Uiso calc R 1 H
C21 0.9722(10) 0.0451(7) 0.0484(6) 0.0317(11) Uani d . 1 C
C22 0.8178(11) 0.1016(7) -0.0781(5) 0.0327(11) Uani d . 1 C
H22 0.8596 0.0483 -0.1586 0.039 Uiso calc R 1 H
N21 0.5250(8) 0.0396(6) -0.0997(5) 0.0330(10) Uani d . 1 N
H21A 0.4799 -0.0729 -0.1166 0.049 Uiso calc R 1 H
H21B 0.4373 0.0775 -0.1711 0.049 Uiso calc R 1 H
H21C 0.4836 0.0772 -0.0241 0.049 Uiso calc R 1 H
C23 0.8961(11) 0.2915(7) -0.0711(6) 0.0347(12) Uani d . 1 C
H23A 1.0884 0.3300 -0.0481 0.042 Uiso calc R 1 H
H23B 0.8213 0.3177 -0.1609 0.042 Uiso calc R 1 H
C24 0.7988(10) 0.3838(7) 0.0352(5) 0.0326(11) Uani d . 1 C
N22 0.7249(14) 0.5211(7) 0.0108(6) 0.0539(15) Uani d . 1 N
H22A 0.6644 0.5743 0.0689 0.065 Uiso calc R 1 H
H22B 0.7368 0.5585 -0.0635 0.065 Uiso calc R 1 H
O2C 0.7869(8) 0.3224(5) 0.1410(4) 0.0404(9) Uani d . 1 O
N1 0.0736(11) 0.6568(6) 0.7532(6) 0.0426(12) Uani d . 1 N
O11 -0.0424(13) 0.7235(7) 0.8224(7) 0.0675(16) Uani d . 1 O
O12 0.3269(10) 0.6938(7) 0.7840(5) 0.0546(12) Uani d . 1 O
O13 -0.0453(11) 0.5465(8) 0.6486(7) 0.0731(18) Uani d . 1 O
N2 0.1374(10) 0.1223(6) 0.6035(6) 0.0416(12) Uani d . 1 N
O21 0.0278(13) -0.0039(7) 0.6398(6) 0.0695(16) Uani d . 1 O
O22 0.3511(14) 0.2098(9) 0.6821(8) 0.100(3) Uani d . 1 O
O23 0.0439(10) 0.1644(7) 0.4930(5) 0.0556(13) Uani d . 1 O
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C11 O1B H1B 109.5 ?
O1A C11 O1B 125.9(6) ?
O1A C11 C12 120.0(5) y
O1B C11 C12 114.1(5) y
N11 C12 C11 111.1(4) ?
N11 C12 C13 109.4(4) ?
C11 C12 C13 111.0(5) ?
N11 C12 H12 108.4 ?
C11 C12 H12 108.4 ?
C13 C12 H12 108.4 ?
C12 N11 H11A 109.5 ?
C12 N11 H11B 109.5 ?
H11A N11 H11B 109.5 ?
C12 N11 H11C 109.5 ?
H11A N11 H11C 109.5 ?
H11B N11 H11C 109.5 ?
C14 C13 C12 111.2(4) ?
C14 C13 H13A 109.4 ?
C12 C13 H13A 109.4 ?
C14 C13 H13B 109.4 ?
C12 C13 H13B 109.4 ?
H13A C13 H13B 108.0 ?
O1C C14 N12 123.4(5) ?
O1C C14 C13 119.7(5) ?
N12 C14 C13 116.9(5) ?
C14 N12 H12A 120.0 ?
C14 N12 H12B 120.0 ?
H12A N12 H12B 120.0 ?
C21 O2B H2B 109.5 ?
O2A C21 O2B 126.1(5) ?
O2A C21 C22 118.5(5) y
O2B C21 C22 115.4(4) y
N21 C22 C23 111.0(5) ?
N21 C22 C21 110.3(4) ?
C23 C22 C21 113.0(4) ?
N21 C22 H22 107.4 ?
C23 C22 H22 107.4 ?
C21 C22 H22 107.4 ?
C22 N21 H21A 109.5 ?
C22 N21 H21B 109.5 ?
H21A N21 H21B 109.5 ?
C22 N21 H21C 109.5 ?
H21A N21 H21C 109.5 ?
H21B N21 H21C 109.5 ?
C24 C23 C22 111.5(4) ?
C24 C23 H23A 109.3 ?
C22 C23 H23A 109.3 ?
C24 C23 H23B 109.3 ?
C22 C23 H23B 109.3 ?
H23A C23 H23B 108.0 ?
O2C C24 N22 123.3(5) ?
O2C C24 C23 118.3(5) ?
N22 C24 C23 118.4(5) ?
C24 N22 H22A 120.0 ?
C24 N22 H22B 120.0 ?
H22A N22 H22B 120.0 ?
O11 N1 O13 122.4(6) ?
O11 N1 O12 121.7(6) ?
O13 N1 O12 115.9(5) ?
O21 N2 O23 122.9(5) ?
O21 N2 O22 117.8(6) ?
O23 N2 O22 119.3(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C11 1.205(8) y
O1B C11 1.298(8) y
O1B H1B 0.8200 ?
C11 C12 1.526(8) ?
C12 N11 1.481(7) ?
C12 C13 1.526(8) ?
C12 H12 0.9800 ?
N11 H11A 0.8900 ?
N11 H11B 0.8900 ?
N11 H11C 0.8900 ?
C13 C14 1.507(8) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 O1C 1.254(8) ?
C14 N12 1.313(9) ?
N12 H12A 0.8600 ?
N12 H12B 0.8600 ?
O2A C21 1.230(7) y
O2B C21 1.275(7) y
O2B H2B 0.8200 ?
C21 C22 1.526(7) ?
C22 N21 1.494(7) ?
C22 C23 1.520(8) ?
C22 H22 0.9800 ?
N21 H21A 0.8900 ?
N21 H21B 0.8900 ?
N21 H21C 0.8900 ?
C23 C24 1.506(8) ?
C23 H23A 0.9700 ?
C23 H23B 0.9700 ?
C24 O2C 1.252(7) ?
C24 N22 1.305(8) ?
N22 H22A 0.8600 ?
N22 H22B 0.8600 ?
N1 O11 1.205(7) ?
N1 O13 1.244(8) ?
N1 O12 1.274(8) ?
N2 O21 1.227(7) ?
N2 O23 1.232(7) ?
N2 O22 1.236(8) ?
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 O2C . 0.82 1.76 2.570(6) 169
N11 H11A O23 . 0.89 2.03 2.858(7) 155
N11 H11A O22 . 0.89 2.39 2.908(8) 117
N11 H11B O12 . 0.89 2.14 2.994(7) 159
N11 H11B O13 . 0.89 2.21 2.951(8) 140
N11 H11C O13 1_655 0.89 1.97 2.855(8) 175
N12 H12A O2A 1_465 0.86 2.09 2.903(8) 156
N12 H12B O23 1_665 0.86 2.17 2.998(7) 162
O2B H2B O1C 1_645 0.82 1.69 2.490(6) 166
N21 H21A O12 1_544 0.89 1.96 2.815(7) 161
N21 H21B O22 1_554 0.89 1.97 2.832(8) 162
N21 H21B O21 1_554 0.89 2.43 3.176(8) 141
N21 H21C O2A 1_455 0.89 2.07 2.887(6) 153
N21 H21C O2C . 0.89 2.45 2.988(6) 120
N22 H22A O1A . 0.86 2.13 2.921(7) 154
N22 H22B O11 1_654 0.86 2.23 3.014(8) 151
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 C11 C12 N11 -176.9(6) y
O1B C11 C12 N11 3.2(7) y
O1A C11 C12 C13 -54.9(7) ?
O1B C11 C12 C13 125.2(5) ?
N11 C12 C13 C14 -168.9(5) y
C11 C12 C13 C14 68.2(6) ?
C12 C13 C14 O1C 46.8(8) y
C12 C13 C14 N12 -135.1(6) y
O2A C21 C22 N21 -173.3(5) y
O2B C21 C22 N21 9.0(6) y
O2A C21 C22 C23 -48.3(7) ?
O2B C21 C22 C23 133.9(5) ?
N21 C22 C23 C24 53.5(6) y
C21 C22 C23 C24 -71.0(6) ?
C22 C23 C24 O2C 32.7(7) y
C22 C23 C24 N22 -145.6(6) y
