#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/74/2237462.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_2237462
loop_
_publ_author_name
'Amimoto, Kiichi'
'Nishiguchi, Hiromitsu'
_publ_section_title
;
 A polymorph of 2,4-dinitrophenylhydrazine
;
_journal_coeditor_code           DS2226
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o425
_journal_paper_doi               10.1107/S1600536813004571
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C6 H6 N4 O4'
_chemical_formula_moiety         'C6 H6 N4 O4'
_chemical_formula_sum            'C6 H6 N4 O4'
_chemical_formula_weight         198.15
_chemical_name_systematic
;
2,4-Dinitrophenylhydrazine
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 123.315(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   12.697(5)
_cell_length_b                   9.179(5)
_cell_length_c                   7.662(5)
_cell_measurement_reflns_used    1986
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.7664
_cell_measurement_theta_min      2.9343
_cell_volume                     746.2(7)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008) and
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
'WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1878
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.9
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1433
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.027
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0446P)²+0.1782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0722
_reflns_number_gt                1424
_reflns_number_total             1433
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ds2226.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2237462
_cod_database_fobs_code          2237462
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
C C1 0.22967(12) 0.03156(15) 0.6894(2) 0.0099(3) Uani d 1
C C2 0.33423(13) 0.08580(17) 0.8822(2) 0.0111(3) Uani d 1
C C3 0.35605(13) 0.23444(16) 0.9232(2) 0.0113(3) Uani d 1
C C4 0.27641(14) 0.33162(17) 0.7701(2) 0.0121(3) Uani d 1
C C5 0.17463(14) 0.28510(15) 0.5739(2) 0.0126(3) Uani d 1
C C6 0.15142(14) 0.13877(16) 0.5363(2) 0.0126(3) Uani d 1
N N1 0.42299(11) -0.00982(14) 1.04810(18) 0.0107(2) Uani d 1
N N2 0.30055(12) 0.48633(14) 0.8159(2) 0.0127(3) Uani d 1
N N3 0.20280(12) -0.11032(13) 0.6487(2) 0.0125(2) Uani d 1
N N4 0.09528(12) -0.15491(14) 0.4547(2) 0.0145(3) Uani d 1
O O1 0.41196(11) -0.14375(11) 1.01911(17) 0.0148(2) Uani d 1
O O2 0.50714(11) 0.04357(13) 1.21641(18) 0.0167(2) Uani d 1
O O3 0.38720(12) 0.52367(12) 0.99101(19) 0.0191(3) Uani d 1
O O4 0.23265(12) 0.57352(12) 0.67622(19) 0.0212(3) Uani d 1
H H3 0.431(2) 0.268(2) 1.060(3) 0.008(4) Uiso d 1
H H3N 0.252(3) -0.162(3) 0.746(4) 0.019(5) Uiso d 1
H H5 0.118(2) 0.350(2) 0.464(4) 0.020(5) Uiso d 1
H H4NA 0.033(2) -0.171(2) 0.476(4) 0.028(5) Uiso d 1
H H4NB 0.116(3) -0.253(3) 0.422(5) 0.037(7) Uiso d 1
H H6 0.082(2) 0.110(3) 0.414(4) 0.020(5) 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 0 '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 0.006 '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
N3 C1 C2 123.59(13)
N3 C1 C6 120.28(13)
C2 C1 C6 116.12(13)
C3 C2 C1 122.10(13)
C3 C2 N1 115.77(13)
C1 C2 N1 122.12(13)
C4 C3 C2 118.74(14)
C4 C3 H3 121.4(12)
C2 C3 H3 119.8(12)
C3 C4 C5 121.90(14)
C3 C4 N2 117.94(13)
C5 C4 N2 120.16(12)
C6 C5 C4 119.14(13)
C6 C5 H5 117.0(14)
C4 C5 H5 123.8(14)
C5 C6 C1 121.93(14)
C5 C6 H6 118.7(15)
C1 C6 H6 119.3(15)
O2 N1 O1 121.72(12)
O2 N1 C2 119.11(13)
O1 N1 C2 119.16(12)
O3 N2 O4 123.23(13)
O3 N2 C4 118.69(11)
O4 N2 C4 118.08(12)
C1 N3 N4 120.02(12)
C1 N3 H3N 113.0(17)
N4 N3 H3N 126.9(17)
N3 N4 H4NA 106.8(15)
N3 N4 H4NB 106.4(17)
H4NA N4 H4NB 106(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N3 1.3389(18)
C1 C2 1.428(2)
C1 C6 1.4320(19)
C2 C3 1.393(2)
C2 N1 1.4430(19)
C3 C4 1.3753(19)
C3 H3 1.01(2)
C4 C5 1.407(2)
C4 N2 1.4545(18)
C5 C6 1.371(2)
C5 H5 0.96(2)
C6 H6 0.90(2)
N1 O2 1.2374(17)
N1 O1 1.2434(17)
N2 O3 1.2273(19)
N2 O4 1.2312(18)
N3 N4 1.4181(18)
N3 H3N 0.81(3)
N4 H4NA 0.91(2)
N4 H4NB 1.01(3)
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 1_545 0.81(3) 2.47(3) 2.919(3) 116(2)
N4 H4NA O1 4_444 0.90(3) 2.43(3) 3.215(3) 145.1(17)
N4 H4NA O3 4_454 0.90(3) 2.35(3) 3.052(3) 135.0(15)
N4 H4NB O4 1_545 1.01(3) 2.31(3) 2.981(3) 123(2)
N4 H4NB O2 3_444 1.01(3) 2.34(3) 3.163(3) 138(3)
N4 H4NB Cg 2_555 1.01(3) 2.91(4) 3.306(3) 104(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3001507
