#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/40/2204078.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_2204078
loop_
_publ_author_name
'Hanife  Saraçoĝlu'
'Ceyda Davran'
'Serkan Soylu'
'Ömer Andaç'
'Hümeyra Batı'
'Nezihe Çalışkan'
_publ_section_title
;
 3-[(2,4-Dinitrophenyl)hydrazono]butan-2-one oxime
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1307
_journal_page_last               o1309
_journal_paper_doi               10.1107/S1600536804015235
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C10 H11 N5 O5'
_chemical_formula_moiety         'C10 H11 N5 O5'
_chemical_formula_sum            'C10 H11 N5 O5'
_chemical_formula_weight         281.24
_chemical_name_systematic
;
3-[(2,4-Dinitrophenyl)hydrazono]butan-2-one oxime
;
_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-97
_cell_angle_alpha                90.000
_cell_angle_beta                 110.950(12)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   10.1400(16)
_cell_length_b                   12.3079(19)
_cell_length_c                   10.6624(18)
_cell_measurement_reflns_used    8500
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.84
_cell_measurement_theta_min      2.04
_cell_volume                     1242.7(4)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1025
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12323
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.170
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.871
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0738P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                1207
_reflns_number_total             2180
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rn6016.cif
_cod_data_source_block           I
_cod_original_cell_volume        1242.7(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204078
_cod_database_fobs_code          2204078
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_type_symbol
N1 0.0765(3) 0.43607(17) 0.1334(2) 0.0612(6) Uani d . 1 N
N2 0.2179(2) 0.20795(17) 0.3256(2) 0.0524(6) Uani d . 1 N
N3 0.2115(3) 0.09776(18) 0.3044(2) 0.0546(6) Uani d . 1 N
N4 0.1859(3) -0.13339(19) 0.2505(2) 0.0607(6) Uani d . 1 N
N5 0.4683(3) -0.2005(2) 0.7159(3) 0.0667(7) Uani d . 1 N
O1 0.0878(2) 0.54816(15) 0.1548(2) 0.0796(7) Uani d . 1 O
H1 0.0399 0.5797 0.0858 0.119 Uiso calc R 1 H
O2 0.1342(3) -0.07263(17) 0.1538(2) 0.0860(7) Uani d . 1 O
O3 0.1729(2) -0.23197(16) 0.2397(2) 0.0844(7) Uani d . 1 O
O4 0.4565(3) -0.2972(2) 0.6883(2) 0.0889(7) Uani d . 1 O
O5 0.5320(3) -0.1659(2) 0.8274(2) 0.0997(8) Uani d . 1 O
C1 0.1509(3) 0.3830(2) 0.2396(3) 0.0533(7) Uani d . 1 C
C2 0.1439(3) 0.2642(2) 0.2222(3) 0.0525(7) Uani d . 1 C
C3 0.2746(3) 0.0255(2) 0.4041(2) 0.0466(6) Uani d . 1 C
C4 0.2634(3) -0.0874(2) 0.3819(2) 0.0486(6) Uani d . 1 C
C5 0.3275(3) -0.1608(2) 0.4837(3) 0.0530(7) Uani d . 1 C
H5 0.3200 -0.2351 0.4671 0.064 Uiso calc R 1 H
C6 0.4014(3) -0.1221(2) 0.6082(3) 0.0505(7) Uani d . 1 C
C7 0.4155(3) -0.0113(2) 0.6347(3) 0.0520(7) Uani d . 1 C
H7 0.4677 0.0131 0.7208 0.062 Uiso calc R 1 H
C8 0.3534(3) 0.0614(2) 0.5357(2) 0.0488(6) Uani d . 1 C
H8 0.3628 0.1354 0.5543 0.059 Uiso calc R 1 H
C9 0.2386(3) 0.4336(2) 0.3680(3) 0.0708(8) Uani d . 1 C
H9A 0.2936 0.4913 0.3508 0.106 Uiso calc R 1 H
H9B 0.3006 0.3800 0.4244 0.106 Uiso calc R 1 H
H9C 0.1787 0.4624 0.4122 0.106 Uiso calc R 1 H
C10 0.0540(4) 0.2172(3) 0.0902(3) 0.0781(9) Uani d . 1 C
H10A 0.1131 0.1909 0.0438 0.117 Uiso calc R 1 H
H10B -0.0081 0.2723 0.0372 0.117 Uiso calc R 1 H
H10C -0.0008 0.1583 0.1049 0.117 Uiso calc R 1 H
H3 0.166(3) 0.071(2) 0.228(3) 0.076(10) 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
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
_geom_angle_publ_flag
C1 N1 O1 111.6(2) yes
C2 N2 N3 114.2(2) yes
C3 N3 N2 122.5(2) yes
C3 N3 H3 116(2) ?
N2 N3 H3 121(2) ?
O3 N4 O2 121.7(2) ?
O3 N4 C4 118.7(2) ?
O2 N4 C4 119.6(2) ?
O5 N5 O4 123.5(3) ?
O5 N5 C6 118.2(3) ?
O4 N5 C6 118.3(3) ?
N1 O1 H1 109.5 ?
N1 C1 C2 113.9(3) yes
N1 C1 C9 124.7(2) yes
C2 C1 C9 121.4(2) ?
N2 C2 C1 115.9(2) yes
N2 C2 C10 124.8(2) ?
C1 C2 C10 119.3(3) ?
N3 C3 C4 121.9(2) yes
N3 C3 C8 120.9(2) yes
C4 C3 C8 117.3(2) ?
C5 C4 C3 121.7(2) ?
C5 C4 N4 116.3(2) ?
C3 C4 N4 122.0(2) ?
C6 C5 C4 118.6(2) ?
C6 C5 H5 120.7 ?
C4 C5 H5 120.7 ?
C5 C6 C7 121.6(2) ?
C5 C6 N5 118.3(2) ?
C7 C6 N5 120.1(3) ?
C8 C7 C6 120.2(2) ?
C8 C7 H7 119.9 ?
C6 C7 H7 119.9 ?
C7 C8 C3 120.5(2) ?
C7 C8 H8 119.8 ?
C3 C8 H8 119.8 ?
C1 C9 H9A 109.5 ?
C1 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C1 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C2 C10 H10A 109.5 ?
C2 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C2 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.292(3) yes
N1 O1 1.396(3) yes
N2 C2 1.290(3) yes
N2 N3 1.373(3) yes
N3 C3 1.358(3) yes
N3 H3 0.85(3) ?
N4 O3 1.221(3) ?
N4 O2 1.229(3) ?
N4 C4 1.454(3) yes
N5 O5 1.210(3) ?
N5 O4 1.222(3) ?
N5 C6 1.467(3) yes
O1 H1 0.8200 ?
C1 C2 1.473(4) yes
C1 C9 1.477(4) yes
C2 C10 1.492(4) yes
C3 C4 1.408(3) ?
C3 C8 1.414(3) ?
C4 C5 1.382(4) ?
C5 C6 1.356(4) ?
C5 H5 0.9300 ?
C6 C7 1.390(4) ?
C7 C8 1.355(3) ?
C7 H7 0.9300 ?
C8 H8 0.9300 ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
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
O1 H1 N1 3_565 0.82 2.22 2.932(3) 146
C7 H7 O4 2_656 0.93 2.54 3.230(4) 131
N3 H3 O2 . 0.85(3) 1.92(3) 2.587(3) 135(2)
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 N2 N3 C3 -175.4(2) yes
O1 N1 C1 C2 -179.47(19) yes
O1 N1 C1 C9 -0.6(4) yes
N3 N2 C2 C1 -178.4(2) yes
N3 N2 C2 C10 1.8(4) ?
N1 C1 C2 N2 179.3(2) yes
C9 C1 C2 N2 0.4(4) ?
N1 C1 C2 C10 -0.9(4) yes
C9 C1 C2 C10 -179.8(3) yes
N2 N3 C3 C4 178.0(2) yes
N2 N3 C3 C8 -1.4(4) yes
N3 C3 C4 C5 -179.9(2) ?
C8 C3 C4 C5 -0.5(4) ?
N3 C3 C4 N4 1.1(4) yes
C8 C3 C4 N4 -179.5(2) ?
O3 N4 C4 C5 5.4(4) ?
O2 N4 C4 C5 -175.3(2) ?
O3 N4 C4 C3 -175.5(2) ?
O2 N4 C4 C3 3.8(4) ?
C3 C4 C5 C6 0.7(4) ?
N4 C4 C5 C6 179.8(2) ?
C4 C5 C6 C7 -0.9(4) ?
C4 C5 C6 N5 179.6(2) ?
O5 N5 C6 C5 -178.7(3) ?
O4 N5 C6 C5 1.2(4) ?
O5 N5 C6 C7 1.8(4) ?
O4 N5 C6 C7 -178.4(3) ?
C5 C6 C7 C8 0.7(4) ?
N5 C6 C7 C8 -179.7(2) ?
C6 C7 C8 C3 -0.4(4) ?
N3 C3 C8 C7 179.7(2) ?
C4 C3 C8 C7 0.3(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21174095
