#------------------------------------------------------------------------------
#$Date: 2016-04-02 04:14:52 +0300 (Sat, 02 Apr 2016) $
#$Revision: 180693 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/74/2107485.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_2107485
loop_
_publ_author_name
'Pogoda, Dorota'
'Janczak, Jan'
'Videnova-Adrabinska, Veneta'
_publ_section_title
;
 New polymorphs of an old drug: conformational and synthon polymorphism of
 5-nitrofurazone
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              263
_journal_page_last               273
_journal_paper_doi               10.1107/S2052520615024956
_journal_volume                  72
_journal_year                    2016
_chemical_formula_moiety         'C6 H6 N4 O4'
_chemical_formula_sum            'C6 H6 N4 O4'
_chemical_formula_weight         198.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.260(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5703(6)
_cell_length_b                   7.8254(3)
_cell_length_c                   7.9677(4)
_cell_measurement_reflns_used    1345
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.40
_cell_measurement_theta_min      3.02
_cell_volume                     826.82(6)
_computing_cell_refinement
;
Oxford Diffraction (2010). CrysAlis Red,
Version 1.171.33.42
;
_computing_data_collection
;
Oxford Diffraction (2010). CrysAlis CCD,
Version 1.171.33.42
;
_computing_data_reduction
;
Oxford Diffraction (2010). CrysAlis Red,
Version 1.171.33.42
;
_computing_molecular_graphics
;
Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular
Structure Visualisation, University of Bonn, Germany
;
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'KUMA KM-4 with CCD detector'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11142
_diffrn_reflns_theta_full        28.500
_diffrn_reflns_theta_max         29.396
_diffrn_reflns_theta_min         3.023
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Oxford Diffraction (2010). CrysAlis Red,
Version 1.171.33.42
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_meas      1.59
_exptl_crystal_density_method    floatation
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0523P)²+0.0108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0814
_reflns_number_gt                1614
_reflns_number_total             2127
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            xk5025sup1.cif
_cod_data_source_block           1061
_cod_database_code               2107485
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.971
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
O O1 0.23439(4) 0.16292(7) 0.51987(7) 0.03382(16) Uani d 1
C C1 0.15329(6) 0.13258(11) 0.58773(11) 0.0340(2) Uani d 1
C C2 0.10884(7) 0.27700(12) 0.62574(12) 0.0413(2) Uani d 1
H H2 0.0519 0.2863 0.6727 0.050 Uiso calc 1
C C3 0.16699(7) 0.41115(12) 0.57904(12) 0.0405(2) Uani d 1
H H3 0.1561 0.5276 0.5899 0.049 Uiso calc 1
C C4 0.24227(6) 0.33758(11) 0.51490(10) 0.03248(19) Uani d 1
N N1 0.12908(6) -0.04135(10) 0.60652(10) 0.0428(2) Uani d 1
O O2 0.05919(6) -0.07059(11) 0.67792(10) 0.0605(2) Uani d 1
O O3 0.17783(7) -0.15180(9) 0.55223(12) 0.0687(3) Uani d 1
C C5 0.32308(6) 0.39903(10) 0.44028(11) 0.0338(2) Uani d 1
H H5 0.3657 0.3223 0.4018 0.041 Uiso calc 1
N N2 0.33598(5) 0.56055(9) 0.42712(9) 0.03357(18) Uani d 1
N N3 0.41281(6) 0.60742(9) 0.35253(9) 0.03636(19) Uani d 1
H H3N 0.4528(8) 0.5333(14) 0.3129(13) 0.044 Uiso d 1
C C6 0.43657(7) 0.77623(11) 0.34068(11) 0.0361(2) Uani d 1
O O4 0.51014(6) 0.81353(9) 0.28090(10) 0.0538(2) Uani d 1
N N4 0.37769(7) 0.88891(11) 0.39663(13) 0.0512(2) Uani d 1
H H41 0.3235(10) 0.8565(15) 0.4398(15) 0.061 Uiso d 1
H H42 0.3926(9) 0.9933(17) 0.3896(15) 0.061 Uiso 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
C1 O1 C4 105.22(6)
C2 C1 O1 112.71(7)
C2 C1 N1 131.20(8)
O1 C1 N1 116.10(8)
C1 C2 C3 105.26(8)
C1 C2 H2 127.4
C3 C2 H2 127.4
C4 C3 C2 106.89(8)
C4 C3 H3 126.6
C2 C3 H3 126.6
C3 C4 O1 109.92(7)
C3 C4 C5 135.44(9)
O1 C4 C5 114.60(7)
O3 N1 O2 124.21(8)
O3 N1 C1 119.17(8)
O2 N1 C1 116.62(9)
N2 C5 C4 119.52(8)
N2 C5 H5 120.2
C4 C5 H5 120.2
C5 N2 N3 115.67(7)
N2 N3 C6 120.41(7)
N2 N3 H3N 124.0(7)
C6 N3 H3N 115.6(7)
O4 C6 N4 124.62(8)
O4 C6 N3 118.62(8)
N4 C6 N3 116.76(8)
C6 N4 H41 122.2(8)
C6 N4 H42 116.7(9)
H41 N4 H42 121.2(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3464(10)
O1 C4 1.3722(10)
C1 C2 1.3455(13)
C1 N1 1.4155(11)
C2 C3 1.4099(13)
C2 H2 0.9300
C3 C4 1.3631(13)
C3 H3 0.9300
C4 C5 1.4367(12)
N1 O3 1.2221(11)
N1 O2 1.2266(11)
C5 N2 1.2834(11)
C5 H5 0.9300
N2 N3 1.3557(10)
N3 C6 1.3678(11)
N3 H3N 0.896(12)
C6 O4 1.2291(11)
C6 N4 1.3289(12)
N4 H41 0.911(13)
N4 H42 0.846(13)
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
N3 H3N O4 2_645 0.896(12) 1.982(12) 2.8258(10) 156.3(10)
N4 H41 O3 1_565 0.911(13) 2.338(13) 3.2283(13) 165.4(11)

_cod_database_fobs_code 2107485
