#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/37/2003706.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_2003706
loop_
_publ_author_name
'Olszak, T. A.'
'Peeters, O. M.'
'Blaton, N. M.'
'De Ranter, C. J.'
_publ_section_title
;
 5-Nitrofuran-2-aldoxime
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1304
_journal_page_last               1306
_journal_paper_doi               10.1107/S0108270194008425
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source
;
 Norwich Eaton Pharmaceuticals, Inc. (Norwich, New York)
;
_chemical_formula_analytical     'C5 H4 N2 O4 '
_chemical_formula_moiety         'C5 H4 N2 O4 '
_chemical_formula_structural     'C5 H4 N2 O4 '
_chemical_formula_sum            'C5 H4 N2 O4'
_chemical_formula_weight         156.10
_chemical_name_systematic
;
5-nitro-2-aldoxime
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3330(4)
_cell_length_b                   5.6330(6)
_cell_length_c                   21.203(3)
_cell_measurement_radiation      'Mo K\a'
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      21.50
_cell_measurement_wavelength     .71069
_cell_volume                     636.95(12)
_computing_cell_refinement       'DIF4,  (STOE & CIE, 1992a)'
_computing_data_collection       'DIF4,  (STOE & CIE, 1992a)'
_computing_data_reduction        'REDU4, (STOE & CIE, 1992b)'
_computing_molecular_graphics    'ORTEX2.1 (McArdle, 1994)'
_computing_publication_material  'PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'STOE STADI-4 four-circle diffractometer  '
_diffrn_measurement_method       'ω scan                                 '
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            3176
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        <3.0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .1347
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.6278
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.146
_refine_ls_extinction_method     'none  '
_refine_ls_goodness_of_fit_all   1.035
_refine_ls_goodness_of_fit_obs   1.101
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_restrained_S_obs      1.101
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_obs          0.0255
_refine_ls_shift/esd_max         0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^)+(0.0497P)^2^]
where P = (F~o~^2^+2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.0719
_refine_ls_wR_factor_obs         0.0685
_reflns_number_observed          1244
_reflns_number_total             1458
_reflns_observed_criterion       >2.0sigma(F^2^)
_cod_data_source_file            na1116.cif
_cod_data_source_block           Y
_cod_original_cell_volume        637.00(10)
_cod_original_sg_symbol_H-M      'P  21 21 21   '
_cod_original_formula_sum        'C5 H4 N2 O4 '
_cod_database_code               2003706
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_22
_atom_site_aniso_U_23
_atom_site_aniso_U_33
O1 .0360(4) -.0035(3) -.0047(3) .0352(4) .0036(3) .0425(4)
C2 .0362(5) -.0016(4) .0019(4) .0318(5) .0013(5) .0389(5)
C21 .0453(6) -.0040(5) -.0041(5) .0393(6) -.0011(5) .0439(6)
N22 .0524(6) -.0063(5) -.0005(5) .0402(6) -.0049(5) .0460(5)
O23 .0550(5) -.0196(5) -.0019(5) .0479(5) .0108(4) .0636(5)
C3 .0353(5) -.0051(6) -.0016(5) .0446(7) .0067(5) .0503(6)
C4 .0363(6) -.0070(6) -.0066(5) .0468(7) .0012(5) .0470(6)
C5 .0362(5) -.0022(4) .0008(4) .0319(5) -.0022(5) .0372(5)
N50 .0416(5) -.0027(4) .0061(4) .0334(5) -.0002(4) .0476(5)
O501 .0515(5) -.0055(5) -.0042(5) .0468(6) .0150(4) .0771(7)
O502 .0589(5) -.0247(5) .0016(5) .0520(6) -.0057(5) .0649(6)
loop_
_atom_site_label
_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_type_symbol
O1 .0306(2) .4555(1) .11689(4) .0379(2) aniso O
C2 .1844(2) .2700(2) .10019(5) .0356(3) aniso C
C21 .0793(2) .1147(2) .05255(6) .0428(3) aniso C
N22 .1849(2) -.0599(2) .02526(5) .0462(3) aniso N
O23 .4288(2) -.0945(2) .04624(5) .0555(3) aniso O
C3 .3979(2) .2736(3) .13548(6) .0434(3) aniso C
C4 .3785(2) .4712(2) .17634(6) .0434(4) aniso C
C5 .1566(2) .5710(2) .16251(5) .0351(3) aniso C
N50 .0398(2) .7762(2) .18854(5) .0409(3) aniso N
O501 -.1643(2) .8378(2) .16800(5) .0585(4) aniso O
O502 .1553(2) .8787(2) .23016(5) .0586(3) aniso O
H21 -.089(3) .141(3) .0426(7) .044(4) iso H
H23 .492(4) -.202(4) .0221(9) .090(7) iso H
H3 .521(3) .167(3) .1324(8) .061(5) iso H
H4 .484(3) .525(3) .2071(7) .057(5) iso H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.001
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.003
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.006
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 0 1
0 3 -1
0 0 14
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
C2 O1 C5 104.80(10) yes
O1 C2 C3 110.20(10) yes
O1 C2 C21 114.10(10) yes
C21 C2 C3 135.60(10) yes
C2 C21 H21 116.0(10) no
C2 C21 N22 127.80(10) yes
N22 C21 H21 116.0(10) no
C21 N22 O23 112.20(10) yes
N22 O23 H23 106.0(10) yes
C2 C3 H3 125.0(10) no
C2 C3 C4 106.60(10) yes
C4 C3 H3 129.0(10) no
C3 C4 H4 131.0(10) no
C3 C4 C5 105.10(10) yes
C5 C4 H4 124.0(10) no
O1 C5 C4 113.20(10) yes
C4 C5 N50 129.80(10) yes
O1 C5 N50 116.90(10) yes
C5 N50 O502 116.30(10) yes
C5 N50 O501 118.80(10) yes
O501 N50 O502 124.90(10) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.3740(10) yes
O1 C5 1.3460(10) yes
C2 C21 1.4490(10) yes
C2 C3 1.3630(10) yes
C21 N22 1.2720(10) yes
C21 H21 .930(10) no
N22 O23 1.3880(10) yes
O23 H23 .86(2) yes
C3 C4 1.4150(10) yes
C3 H3 .890(10) no
C4 C5 1.3420(10) yes
C4 H4 .910(10) no
C5 N50 1.4240(10) yes
N50 O501 1.2220(10) yes
N50 O502 1.2210(10) yes
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
C2 O1 C5 N50 179.40(10) no
C2 O1 C5 C4 -.50(10) no
C5 O1 C2 C3 .40(10) no
C5 O1 C2 C21 177.80(10) no
O1 C2 C3 C4 -.20(10) no
O1 C2 C3 H3 179.0(10) no
O1 C2 C21 N22 174.90(10) no
O1 C2 C21 H21 -8.0(10) no
C21 C2 C3 C4 -176.80(10) no
C21 C2 C3 H3 2.0(10) no
C3 C2 C21 H21 167.0(10) no
C3 C2 C21 N22 -8.6(3) no
C2 C21 N22 O23 .2(2) no
H21 C21 N22 O23 -175.0(10) no
C21 N22 O23 H23 -172.0(10) no
C2 C3 C4 C5 -.10(10) no
C2 C3 C4 H4 178.0(10) no
H3 C3 C4 H4 0(2) no
H3 C3 C4 C5 -178.0(10) no
C3 C4 C5 O1 .40(10) no
C3 C4 C5 N50 -179.50(10) no
H4 C4 C5 O1 -177.0(10) no
H4 C4 C5 N50 2.0(10) no
C4 C5 N50 O501 179.00(10) no
O1 C5 N50 O501 -.8(2) no
C4 C5 N50 O502 -.5(2) no
O1 C5 N50 O502 179.60(10) no
