#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/99/2219918.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_2219918
loop_
_publ_author_name
'Yuan, Chunlan'
_publ_section_title
;
 (2,4-Dinitrophenyl)(1-methyl-1-nitroethyl)diazene
;
_journal_coeditor_code           KP2190
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2198
_journal_paper_doi               10.1107/S1600536808034454
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C9 H9 N5 O6'
_chemical_formula_moiety         'C9 H9 N5 O6'
_chemical_formula_sum            'C9 H9 N5 O6'
_chemical_formula_weight         283.21
_chemical_name_systematic
;
(2,4-Dinitrophenyl)(1-methyl-1-nitroethyl)diazene
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.00
_cell_angle_beta                 92.18(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.495(4)
_cell_length_b                   12.847(4)
_cell_length_c                   14.362(3)
_cell_measurement_reflns_used    33
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13.51
_cell_measurement_theta_min      4.26
_cell_volume                     2488.1(12)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'SHELXTL (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       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  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9672
_diffrn_reflns_theta_full        25.56
_diffrn_reflns_theta_max         25.56
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0.85
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.845
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0595
_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)+(0.1218P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.2036
_reflns_number_gt                1026
_reflns_number_total             2336
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2190.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2219918
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'
'-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_refinement_flags
_atom_site_occupancy
O O1 0.4199(4) 0.4172(3) 0.3171(2) 0.175(2) Uani d . 1
O O2 0.3274(3) 0.4313(2) 0.1933(2) 0.1333(13) Uani d . 1
O O3 0.2968(2) 0.1231(3) 0.00469(19) 0.1178(11) Uani d . 1
O O4 0.2871(3) -0.0239(4) 0.0731(3) 0.170(2) Uani d . 1
O O5 0.4965(3) 0.1031(3) 0.6134(3) 0.1268(13) Uani d . 1
O O6 0.5905(3) 0.2187(3) 0.6742(2) 0.1470(15) Uani d . 1
N N1 0.3952(2) 0.2560(2) 0.42044(18) 0.0693(8) Uani d . 1
N N2 0.4630(2) 0.2226(2) 0.46842(17) 0.0692(8) Uani d . 1
N N3 0.3672(3) 0.3804(3) 0.2542(3) 0.1072(13) Uani d . 1
N N4 0.3057(2) 0.0686(4) 0.0723(2) 0.0964(11) Uani d . 1
N N5 0.5245(3) 0.1903(4) 0.6209(2) 0.0946(11) Uani d . 1
C C6 0.3831(2) 0.2084(3) 0.33028(19) 0.0553(8) Uani d . 1
C C1 0.3611(2) 0.2680(3) 0.2510(2) 0.0622(8) Uani d . 1
C C2 0.3345(2) 0.2222(3) 0.1672(2) 0.0653(9) Uani d . 1
H H2 0.3181 0.2624 0.1150 0.078 Uiso calc R 1
C C3 0.3330(2) 0.1171(3) 0.1629(2) 0.0669(9) Uani d . 1
C C4 0.3567(3) 0.0556(3) 0.2382(2) 0.0825(11) Uani d . 1
H H4 0.3564 -0.0166 0.2327 0.099 Uiso calc R 1
C C5 0.3809(2) 0.1023(3) 0.3226(2) 0.0698(10) Uani d . 1
H H5 0.3959 0.0613 0.3746 0.084 Uiso calc R 1
C C7 0.4696(3) 0.2740(3) 0.5614(2) 0.0692(9) Uani d . 1
C C9 0.3722(3) 0.2914(4) 0.6046(2) 0.1031(15) Uani d . 1
H H9A 0.3377 0.3472 0.5729 0.155 Uiso calc R 1
H H9B 0.3829 0.3091 0.6691 0.155 Uiso calc R 1
H H9C 0.3331 0.2290 0.5996 0.155 Uiso calc R 1
C C8 0.5338(5) 0.3655(4) 0.5534(3) 0.138(2) Uani d . 1
H H8A 0.5940 0.3458 0.5246 0.207 Uiso calc R 1
H H8B 0.5492 0.3931 0.6144 0.207 Uiso calc R 1
H H8C 0.5001 0.4175 0.5161 0.207 Uiso calc R 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
O3 N4 O4 124.4(4)
O3 N4 C3 118.7(4)
O4 N4 C3 116.7(4)
O2 N3 O1 124.0(4)
O2 N3 C1 119.7(3)
O1 N3 C1 116.1(4)
N2 N1 C6 115.0(3)
N1 N2 C7 111.9(3)
O5 N5 O6 124.5(4)
O5 N5 C7 117.6(3)
O6 N5 C7 117.8(4)
C5 C6 C1 118.5(3)
C5 C6 N1 119.9(3)
C1 C6 N1 121.0(3)
C2 C1 C6 121.3(3)
C2 C1 N3 117.9(3)
C6 C1 N3 120.8(3)
C3 C2 C1 118.1(3)
C3 C2 H2 121.0
C2 C2 H2 121.0
C2 C3 C4 122.6(3)
C2 C3 N4 117.7(3)
C4 C3 N4 119.7(4)
C3 C4 C5 118.9(4)
C3 C4 H4 120.6
C5 C4 H4 120.6
C6 C5 C4 120.5(3)
C6 C5 H5 119.7
C4 C5 H5 119.7
C8 C7 N2 107.5(3)
C8 C7 C8 116.4(4)
N2 C7 C8 107.5(3)
C8 C7 N5 109.2(4)
N2 C7 N5 101.5(3)
C9 C7 N5 106.6(3)
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.227(4)
O2 N3 1.201(4)
O3 N4 1.200(4)
O4 N4 1.215(5)
O5 N5 1.186(4)
O6 N5 1.209(4)
N1 N2 1.203(3)
N1 C6 1.436(4)
N2 C7 1.489(4)
N3 C1 1.447(5)
N4 C3 1.478(4)
N5 C7 1.544(5)
C1 C2 1.375(4)
C2 C3 1.351(5)
C2 H2 0.9300
C3 C4 1.368(5)
C4 C5 1.381(4)
C4 H4 0.9300
C5 H5 0.9300
C6 C5 1.368(5)
C6 C1 1.395(4)
C7 C8 1.467(6)
C7 C9 1.493(5)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10445759
