#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/38/2233897.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_2233897
loop_
_publ_author_name
'Asik, Safra Izuani Jama'
'Fun, Hoong-Kun'
'Razak, Ibrahim Abdul'
'Jansrisewangwong, Patcharaporn'
'Chantraproma, Suchada'
_publ_section_title
;
 (1E,2E)-1,2-Bis[1-(3-nitrophenyl)ethylidene]hydrazine
;
_journal_coeditor_code           IS5067
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o643
_journal_paper_doi               10.1107/S1600536812004722
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H14 N4 O4'
_chemical_formula_moiety         'C16 H14 N4 O4'
_chemical_formula_sum            'C16 H14 N4 O4'
_chemical_formula_weight         326.31
_chemical_name_systematic
;
(1E,2E)-1,2-Bis[1-(3-nitrophenyl)ethylidene]hydrazine
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.0220(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.9296(3)
_cell_length_b                   7.4448(5)
_cell_length_c                   26.3979(19)
_cell_measurement_reflns_used    4585
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.84
_cell_volume                     770.37(10)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            15392
_diffrn_reflns_theta_full        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         1.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0471
_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)+(0.0690P)²+0.1466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1463
_reflns_number_gt                1686
_reflns_number_total             2254
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5067.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233897
_cod_database_fobs_code          2233897
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_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
_atom_site_symmetry_multiplicity
O O1 0.9642(5) 0.1248(2) 0.20045(5) 0.1005(6) Uani d . 1 1
O O2 0.8102(4) 0.06399(18) 0.12349(5) 0.0867(5) Uani d . 1 1
N N1 0.0796(3) 0.47453(16) 0.02358(4) 0.0461(3) Uani d . 1 1
N N2 0.8220(3) 0.16404(18) 0.15972(5) 0.0572(3) Uani d . 1 1
C C1 0.3995(4) 0.6788(2) 0.14058(5) 0.0507(3) Uani d . 1 1
H H1A 0.3117 0.7942 0.1362 0.061 Uiso calc R 1 1
C C2 0.5585(4) 0.6293(2) 0.18705(6) 0.0583(4) Uani d . 1 1
H H2A 0.5726 0.7113 0.2137 0.070 Uiso calc R 1 1
C C3 0.6956(4) 0.4607(2) 0.19421(5) 0.0525(4) Uani d . 1 1
H H3A 0.8039 0.4272 0.2252 0.063 Uiso calc R 1 1
C C4 0.6669(3) 0.34261(18) 0.15379(5) 0.0429(3) Uani d . 1 1
C C5 0.5072(3) 0.38640(17) 0.10740(4) 0.0400(3) Uani d . 1 1
H H5A 0.4914 0.3029 0.0811 0.048 Uiso calc R 1 1
C C6 0.3697(3) 0.55758(17) 0.10032(4) 0.0390(3) Uani d . 1 1
C C7 0.1991(3) 0.60690(18) 0.05020(5) 0.0399(3) Uani d . 1 1
C C8 0.1829(5) 0.7991(2) 0.03461(6) 0.0643(4) Uani d . 1 1
H H8A 0.1410 0.8068 -0.0016 0.096 Uiso calc R 1 1
H H8B 0.3956 0.8567 0.0447 0.096 Uiso calc R 1 1
H H8C 0.0016 0.8578 0.0507 0.096 Uiso calc R 1 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_site_symmetry_3
_geom_angle
C7 N1 N1 3_565 113.69(14)
O2 N2 O1 . 122.84(15)
O2 N2 C4 . 118.75(12)
O1 N2 C4 . 118.38(14)
C2 C1 C6 . 120.76(14)
C2 C1 H1A . 119.6
C6 C1 H1A . 119.6
C3 C2 C1 . 120.81(14)
C3 C2 H2A . 119.6
C1 C2 H2A . 119.6
C2 C3 C4 . 117.74(12)
C2 C3 H3A . 121.1
C4 C3 H3A . 121.1
C5 C4 C3 . 122.99(13)
C5 C4 N2 . 118.04(12)
C3 C4 N2 . 118.94(12)
C4 C5 C6 . 119.02(12)
C4 C5 H5A . 120.5
C6 C5 H5A . 120.5
C5 C6 C1 . 118.67(11)
C5 C6 C7 . 119.49(11)
C1 C6 C7 . 121.84(12)
N1 C7 C6 . 115.05(11)
N1 C7 C8 . 125.53(12)
C6 C7 C8 . 119.41(12)
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_site_symmetry_2
_geom_bond_distance
O1 N2 . 1.2121(16)
O2 N2 . 1.2105(19)
N1 C7 . 1.2803(17)
N1 N1 3_565 1.406(2)
N2 C4 . 1.4663(19)
C1 C2 . 1.387(2)
C1 C6 . 1.3930(19)
C1 H1A . 0.9300
C2 C3 . 1.374(2)
C2 H2A . 0.9300
C3 C4 . 1.3808(19)
C3 H3A . 0.9300
C4 C5 . 1.3756(17)
C5 C6 . 1.3916(18)
C5 H5A . 0.9300
C6 C7 . 1.4867(17)
C7 C8 . 1.489(2)
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 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
_geom_hbond_publ_flag
C3 H3A O1 2_755 0.9300 2.5700 3.239(2) 129.00 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_site_symmetry_1
_geom_torsion
C6 C1 C2 C3 . 1.1(2)
C1 C2 C3 C4 . -0.5(2)
C2 C3 C4 C5 . -0.3(2)
C2 C3 C4 N2 . 177.71(14)
O2 N2 C4 C5 . 1.6(2)
O1 N2 C4 C5 . 179.73(15)
O2 N2 C4 C3 . -176.58(16)
O1 N2 C4 C3 . 1.6(2)
C3 C4 C5 C6 . 0.5(2)
N2 C4 C5 C6 . -177.55(11)
C4 C5 C6 C1 . 0.12(19)
C4 C5 C6 C7 . 179.49(11)
C2 C1 C6 C5 . -0.9(2)
C2 C1 C6 C7 . 179.72(13)
N1 N1 C7 C6 3_565 -179.90(13)
N1 N1 C7 C8 3_565 -0.7(2)
C5 C6 C7 N1 . 24.84(17)
C1 C6 C7 N1 . -155.80(13)
C5 C6 C7 C8 . -154.43(14)
C1 C6 C7 C8 . 24.9(2)
