#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/23/2202363.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_2202363
loop_
_publ_author_name
'Kennedy, Alan R.'
'Khalaf, Abedawn I. '
'Suckling, Colin J. '
'Waigh, Roger D. '
_publ_section_title
;
 Ethyl 5-oxo-2,5-dihydro-4-isoxazolecarboxylate hydroxylamine salt
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1410
_journal_page_last               o1412
_journal_paper_doi               10.1107/S1600536803018828
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'N H4 O 1+, C6 H6 N O4 1-'
_chemical_formula_moiety         'N H4 O 1+, C6 H6 N O4 1-'
_chemical_formula_sum            'C6 H10 N2 O5'
_chemical_formula_weight         190.16
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.212(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6788(2)
_cell_length_b                   13.3277(6)
_cell_length_c                   13.5380(7)
_cell_measurement_reflns_used    1706
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     837.52(7)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
;
DENZO and COLLECT (Otwinowski & Minor, 1997; Nonius, 1988)
;
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_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  0.027
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5375
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.03
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0378
_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)+(0.0278P)²+0.4766P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                1536
_reflns_number_total             1894
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6333.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2202363
_cod_database_fobs_code          2202363
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_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 1.1691(2) 0.08463(8) 0.39923(8) 0.0220(3) Uani d . 1 . . O
O2 1.1901(2) 0.20808(8) 0.28669(8) 0.0214(2) Uani d . 1 . . O
O3 0.7211(2) 0.15399(8) 0.53349(8) 0.0220(3) Uani d . 1 . . O
O4 0.5776(2) 0.31279(8) 0.49485(8) 0.0217(2) Uani d . 1 . . O
O5 0.4513(2) 0.49643(9) 0.19875(8) 0.0258(3) Uani d . 1 . . O
N1 1.0604(3) 0.30382(10) 0.26271(10) 0.0238(3) Uani d . 1 . . N
N2 0.2721(3) 0.44131(10) 0.12622(10) 0.0194(3) Uani d . 1 . . N
C1 1.0782(3) 0.16876(11) 0.36709(10) 0.0171(3) Uani d . 1 . . C
C2 0.8833(3) 0.31791(11) 0.32830(11) 0.0207(3) Uani d . 1 . . C
C3 0.8807(3) 0.23770(11) 0.39600(11) 0.0171(3) Uani d . 1 . . C
C4 0.7226(3) 0.22838(11) 0.48015(11) 0.0173(3) Uani d . 1 . . C
C5 0.4258(3) 0.31709(12) 0.58205(11) 0.0221(3) Uani d . 1 . . C
C6 0.2835(4) 0.41826(13) 0.58026(13) 0.0274(4) Uani d . 1 . . C
H1 0.772(4) 0.3790(14) 0.3243(13) 0.027(5) Uiso d . 1 . . H
H2 0.566(4) 0.3078(13) 0.6433(14) 0.029(5) Uiso d . 1 . . H
H3 0.281(4) 0.2628(13) 0.5771(12) 0.020(4) Uiso d . 1 . . H
H4 0.429(4) 0.4703(15) 0.5854(15) 0.037(5) Uiso d . 1 . . H
H5 0.161(4) 0.4263(14) 0.5173(15) 0.032(5) Uiso d . 1 . . H
H6 0.170(4) 0.4232(14) 0.6349(15) 0.037(5) Uiso d . 1 . . H
H7 0.576(6) 0.535(2) 0.160(2) 0.072(8) Uiso d . 1 . . H
H8 0.184(4) 0.3891(15) 0.1635(15) 0.035(5) Uiso d . 1 . . H
H9 0.127(4) 0.4846(15) 0.0969(15) 0.036(5) Uiso d . 1 . . H
H10 0.378(4) 0.4133(15) 0.0790(15) 0.038(5) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'
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 O2 N1 109.12(10) y
C4 O4 C5 117.48(11) ?
N2 O5 H7 104.0(15) ?
C2 N1 O2 105.17(12) y
O5 N2 H8 105.2(11) ?
O5 N2 H9 107.9(12) ?
H8 N2 H9 109.1(16) ?
O5 N2 H10 111.2(12) ?
H8 N2 H10 111.2(17) ?
H9 N2 H10 111.9(17) ?
O1 C1 O2 118.01(13) y
O1 C1 C3 134.28(14) y
O2 C1 C3 107.70(12) y
N1 C2 C3 113.09(14) y
N1 C2 H1 118.0(11) ?
C3 C2 H1 128.9(11) ?
C1 C3 C2 104.92(13) y
C1 C3 C4 126.16(13) ?
C2 C3 C4 128.86(13) ?
O3 C4 O4 123.37(13) ?
O3 C4 C3 125.23(13) ?
O4 C4 C3 111.39(12) ?
O4 C5 C6 106.44(12) ?
O4 C5 H2 109.3(11) ?
C6 C5 H2 111.6(11) ?
O4 C5 H3 108.5(10) ?
C6 C5 H3 111.0(9) ?
H2 C5 H3 109.8(14) ?
C5 C6 H4 109.6(12) ?
C5 C6 H5 109.0(11) ?
H4 C6 H5 108.5(16) ?
C5 C6 H6 109.5(12) ?
H4 C6 H6 110.3(16) ?
H5 C6 H6 109.9(16) ?
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 . 1.2574(17) y
O2 C1 . 1.3698(17) y
O2 N1 . 1.4326(16) y
O3 C4 . 1.2270(18) y
O4 C4 . 1.3414(17) y
O4 C5 . 1.4533(17) y
O5 N2 . 1.4143(16) y
O5 H7 . 0.98(3) ?
N1 C2 . 1.3022(19) y
N2 H8 . 0.98(2) ?
N2 H9 . 0.94(2) ?
N2 H10 . 0.93(2) ?
C1 C3 . 1.394(2) y
C2 C3 . 1.409(2) y
C2 H1 . 0.965(19) ?
C3 C4 . 1.4395(19) y
C5 C6 . 1.503(2) ?
C5 H2 . 0.999(19) ?
C5 H3 . 0.988(17) ?
C6 H4 . 0.97(2) ?
C6 H5 . 0.97(2) ?
C6 H6 . 0.97(2) ?
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
O5 H7 O1 2_755 0.98(3) 1.66(3) 2.6244(15) 170(2)
O5 H7 O2 2_755 0.98(3) 2.62(3) 3.2753(15) 124.8(19)
N2 H8 N1 1_455 0.98(2) 1.90(2) 2.8657(19) 166.2(17)
N2 H9 O1 2_655 0.94(2) 1.93(2) 2.8019(17) 153.6(17)
N2 H10 O3 4_565 0.93(2) 2.00(2) 2.8750(17) 154.8(17)
N2 H10 O1 4_465 0.93(2) 2.51(2) 3.0696(17) 118.9(15)
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
C1 O2 N1 C2 0.52(15)
N1 O2 C1 O1 -179.54(12)
N1 O2 C1 C3 -0.52(15)
O2 N1 C2 C3 -0.32(17)
O1 C1 C3 C2 179.11(16)
O2 C1 C3 C2 0.32(15)
O1 C1 C3 C4 1.7(3)
O2 C1 C3 C4 -177.07(13)
N1 C2 C3 C1 0.01(17)
N1 C2 C3 C4 177.30(14)
C5 O4 C4 O3 3.7(2)
C5 O4 C4 C3 -175.35(13)
C1 C3 C4 O3 -6.7(2)
C2 C3 C4 O3 176.55(15)
C1 C3 C4 O4 172.29(13)
C2 C3 C4 O4 -4.5(2)
C4 O4 C5 C6 -179.87(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654704
