#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:14:18 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178942 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/71/4117189.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4117189
loop_
_publ_author_name
'Christer B. Aakeröy'
'Deirdre P. Hughes'
'Mark Nieuwenhuyzen'
_publ_section_title
;
 The Oxamate Anion: A Flexible Building Block of Hydrogen-Bonded
 Architectures for Crystal Engineering
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10134
_journal_page_last               10140
_journal_paper_doi               10.1021/ja953296v
_journal_volume                  118
_journal_year                    1996
_chemical_formula_sum            'C5 H7 N3 O3'
_chemical_formula_weight         157.14
_chemical_name_systematic
; 
 ? 
;
_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           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 96.61
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.162(3)
_cell_length_b                   12.801(2)
_cell_length_c                   8.7770(10)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      10
_cell_volume                     687.7(4)
_computing_cell_refinement       'XSCANS (Siemens, 1995)'
_computing_data_collection       'XSCANS (Siemens, 1995)'
_computing_data_reduction        'XSCANS (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL PC (Sheldrick, 1990)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'Omega Scans'
_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  0.0518
_diffrn_reflns_av_sigmaI/netI    0.1083
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1332
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.83
_diffrn_standards_decay_%        1%
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       Needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.035
_refine_ls_goodness_of_fit_obs   1.109
_refine_ls_hydrogen_treatment    'Located from Fourier, Riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_restrained_S_obs      1.109
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_obs          0.0770
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1118P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2162
_refine_ls_wR_factor_obs         0.1717
_reflns_number_observed          698
_reflns_number_total             1215
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja953296v_3.cif
_cod_data_source_block           imidoxam
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1118P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1118P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4117189
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.028(2) 0.042(2) 0.012(2) -0.008(2) 0.010(2) -0.005(2)
N1 0.019(2) 0.030(3) 0.012(2) -0.001(2) 0.008(2) -0.001(2)
C1 0.025(3) 0.019(3) 0.013(3) 0.002(2) 0.005(2) -0.001(2)
C2 0.016(3) 0.023(3) 0.011(2) 0.001(2) 0.006(2) -0.007(2)
O21 0.018(2) 0.031(2) 0.013(2) -0.001(2) 0.007(2) 0.000(2)
O22 0.029(2) 0.034(2) 0.007(2) -0.002(2) 0.008(2) -0.005(2)
N3 0.029(3) 0.027(3) 0.007(2) 0.001(2) 0.005(2) -0.001(2)
C4 0.020(3) 0.025(3) 0.016(3) -0.002(2) 0.003(2) -0.002(2)
C5 0.020(3) 0.025(3) 0.015(3) 0.002(2) 0.004(2) -0.004(2)
N6 0.031(3) 0.025(3) 0.010(2) -0.001(2) 0.007(2) -0.003(2)
C7 0.016(3) 0.029(3) 0.018(3) 0.001(2) 0.008(2) -0.002(2)
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.5675(6) 0.6608(3) 0.3922(4) 0.0267(10) Uani 1 d .
N1 N 0.3750(7) 0.5811(4) 0.1890(5) 0.0200(10) Uani 1 d .
H11 H 0.2390(7) 0.6023(4) 0.2284(5) 0.024 Uiso 1 d R
H12 H 0.3726(7) 0.5607(4) 0.0947(5) 0.024 Uiso 1 d R
C1 C 0.5547(9) 0.6167(4) 0.2665(5) 0.0190(12) Uani 1 d .
C2 C 0.7696(8) 0.6028(4) 0.1872(5) 0.0162(12) Uani 1 d .
O21 O 0.9446(6) 0.6178(3) 0.2702(4) 0.0204(9) Uani 1 d .
O22 O 0.7437(6) 0.5805(3) 0.0466(4) 0.0228(10) Uani 1 d .
N3 N 1.0048(8) 0.3663(3) 0.1777(4) 0.0208(11) Uani 1 d .
H3 H 1.0509(8) 0.3743(3) 0.0855(4) 0.025 Uiso 1 d R
C4 C 0.7932(9) 0.3479(4) 0.2039(6) 0.0204(12) Uani 1 d .
H4 H 0.6756(9) 0.3421(4) 0.1233(6) 0.024 Uiso 1 d R
C5 C 0.7933(8) 0.3402(4) 0.3576(6) 0.0198(12) Uani 1 d .
H5 H 0.6711(8) 0.3218(4) 0.4164(6) 0.024 Uiso 1 d R
N6 N 1.0010(8) 0.3553(4) 0.4220(4) 0.0215(11) Uani 1 d .
H6 H 1.0639(8) 0.3407(4) 0.5262(4) 0.026 Uiso 1 d R
C7 C 1.1289(9) 0.3704(4) 0.3103(6) 0.0205(12) Uani 1 d .
H7 H 1.2766(9) 0.3820(4) 0.3409(6) 0.025 Uiso 1 d R
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
O1 C1 N1 125.8(5)
O1 C1 C2 118.4(4)
N1 C1 C2 115.7(4)
O21 C2 O22 127.8(5)
O21 C2 C1 116.1(4)
O22 C2 C1 116.1(4)
C7 N3 C4 109.0(4)
C5 C4 N3 106.8(5)
N6 C5 C4 107.4(4)
C7 N6 C5 108.8(4)
N3 C7 N6 108.0(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.234(6)
N1 C1 1.313(7)
C1 C2 1.576(7)
C2 O21 1.244(6)
C2 O22 1.259(6)
N3 C7 1.318(7)
N3 C4 1.370(7)
C4 C5 1.353(7)
C5 N6 1.352(7)
N6 C7 1.341(7)
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
O1 C1 C2 O21 14.3(7)
N1 C1 C2 O21 -166.9(5)
O1 C1 C2 O22 -164.0(5)
N1 C1 C2 O22 14.8(7)
C7 N3 C4 C5 -0.4(6)
N3 C4 C5 N6 0.8(6)
C4 C5 N6 C7 -0.9(6)
C4 N3 C7 N6 -0.2(6)
C5 N6 C7 N3 0.7(6)
