#------------------------------------------------------------------------------
#$Date: 2023-12-22 17:07:40 +0200 (Fri, 22 Dec 2023) $
#$Revision: 288505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/80/2018052.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_2018052
loop_
_publ_author_name
'Collas, Alain'
'Zeller, Matthias'
'Blockhuys, Frank'
_publ_section_title
;
 Conformational polymorphism of
 (E,E)-N,N'-bis(4-nitrobenzylidene)benzene-1,4-diamine
;
_journal_coeditor_code           BM3102
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o171
_journal_page_last               o174
_journal_paper_doi               10.1107/S0108270111010109
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H14 N4 O4'
_chemical_formula_moiety         'C20 H14 N4 O4'
_chemical_formula_sum            'C20 H14 N4 O4'
_chemical_formula_weight         374.35
_chemical_name_systematic
;
(E,E)-N,N'-bis(4-nitrobenzylidene)benzene-
1,4-diamine
;
_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                90.00
_cell_angle_beta                 102.558(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5670(10)
_cell_length_b                   5.0227(7)
_cell_length_c                   26.723(5)
_cell_measurement_reflns_used    1008
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.51
_cell_measurement_theta_min      3.18
_cell_volume                     860.3(2)
_computing_cell_refinement       'APEX2 (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'APEX2 (Bruker, 2008)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            4451
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(APEX2; Bruker, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0398
_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)+(0.0467P)²+0.0920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                1181
_reflns_number_total             1753
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm3102.cif
_cod_data_source_block           I-2
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        860.4(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018052
_cod_database_fobs_code          2018052
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_disorder_assembly
_atom_site_disorder_group
C C1 0.0372(2) 1.1170(3) 0.37643(6) 0.0435(4) Uani d . 1 . .
C C2 -0.1386(2) 1.1873(4) 0.39398(7) 0.0508(4) Uani d . 1 . .
H H2 -0.1645 1.1065 0.4233 0.061 Uiso calc R 1 . .
C C3 -0.2753(3) 1.3746(4) 0.36876(6) 0.0501(5) Uani d . 1 . .
H H3 -0.3942 1.4200 0.3805 0.060 Uiso calc R 1 . .
C C4 -0.2331(2) 1.4942(3) 0.32576(6) 0.0424(4) Uani d . 1 . .
C C5 -0.0603(3) 1.4307(4) 0.30734(6) 0.0528(5) Uani d . 1 . .
H H5 -0.0343 1.5142 0.2783 0.063 Uiso calc R 1 . .
C C6 0.0740(3) 1.2408(4) 0.33280(6) 0.0529(5) Uani d . 1 . .
H H6 0.1915 1.1944 0.3206 0.063 Uiso calc R 1 . .
C C7 0.1888(3) 0.9248(3) 0.40361(6) 0.0485(4) Uani d . 1 . .
H H7 0.3038 0.8836 0.3900 0.058 Uiso calc R 1 . .
C C9 0.3384(2) 0.6540(3) 0.47115(6) 0.0403(4) Uani d . 1 . .
C C10 0.2953(2) 0.4366(3) 0.49885(6) 0.0467(4) Uani d . 1 . .
H H10 0.1574 0.3930 0.4985 0.056 Uiso calc R 1 . .
C C11 0.5467(2) 0.7157(3) 0.47324(6) 0.0470(4) Uani d . 1 . .
H H11 0.5794 0.8628 0.4554 0.056 Uiso calc R 1 . .
N N1 -0.3757(2) 1.7008(3) 0.29970(5) 0.0503(4) Uani d . 1 . .
N N2 0.17115(19) 0.8119(3) 0.44468(5) 0.0455(4) Uani d . 1 . .
O O1 -0.3319(2) 1.8127(3) 0.26298(5) 0.0696(4) Uani d . 1 . .
O O2 -0.5305(2) 1.7529(3) 0.31623(5) 0.0688(4) Uani 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 118.76(15) ?
C2 C1 C7 . . 121.91(15) ?
C6 C1 C7 . . 119.28(15) ?
C3 C2 C1 . . 120.93(16) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C2 C3 C4 . . 118.66(16) ?
C2 C3 H3 . . 120.7 ?
C4 C3 H3 . . 120.7 ?
C5 C4 C3 . . 122.12(16) ?
C5 C4 N1 . . 119.16(15) ?
C3 C4 N1 . . 118.70(15) ?
C4 C5 C6 . . 118.44(16) ?
C4 C5 H5 . . 120.8 ?
C6 C5 H5 . . 120.8 ?
C5 C6 C1 . . 121.08(16) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
N2 C7 C1 . . 123.17(15) ?
N2 C7 H7 . . 118.4 ?
C1 C7 H7 . . 118.4 ?
C10 C9 C11 . . 117.92(15) ?
C10 C9 N2 . . 118.92(14) ?
C11 C9 N2 . . 123.05(15) ?
C11 C10 C9 3_666 . 120.84(15) ?
C11 C10 H10 3_666 . 119.6 ?
C9 C10 H10 . . 119.6 ?
C10 C11 C9 3_666 . 121.24(15) ?
C10 C11 H11 3_666 . 119.4 ?
C9 C11 H11 . . 119.4 ?
O1 N1 O2 . . 123.61(15) ?
O1 N1 C4 . . 118.02(14) ?
O2 N1 C4 . . 118.37(15) ?
C7 N2 C9 . . 118.59(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.383(2) ?
C1 C6 . 1.388(2) ?
C1 C7 . 1.461(2) ?
C2 C3 . 1.372(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.377(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.369(2) ?
C4 N1 . 1.469(2) ?
C5 C6 . 1.375(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N2 . 1.263(2) ?
C7 H7 . 0.9300 ?
C9 C10 . 1.383(2) ?
C9 C11 . 1.392(2) ?
C9 N2 . 1.414(2) ?
C10 C11 3_666 1.371(2) ?
C10 H10 . 0.9300 ?
C11 C10 3_666 1.371(2) ?
C11 H11 . 0.9300 ?
N1 O1 . 1.2186(18) ?
N1 O2 . 1.2215(18) ?
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.4(3) ?
C7 C1 C2 C3 . . . . 177.88(16) ?
C1 C2 C3 C4 . . . . -0.7(3) ?
C2 C3 C4 C5 . . . . 0.4(3) ?
C2 C3 C4 N1 . . . . -178.05(14) ?
C3 C4 C5 C6 . . . . 0.2(3) ?
N1 C4 C5 C6 . . . . 178.67(15) ?
C4 C5 C6 C1 . . . . -0.6(3) ?
C2 C1 C6 C5 . . . . 0.3(3) ?
C7 C1 C6 C5 . . . . -177.30(16) ?
C2 C1 C7 N2 . . . . -0.5(3) ?
C6 C1 C7 N2 . . . . 177.02(16) ?
C11 C9 C10 C11 . . . 3_666 -1.1(3) ?
N2 C9 C10 C11 . . . 3_666 -177.37(15) ?
C10 C9 C11 C10 . . . 3_666 1.1(3) ?
N2 C9 C11 C10 . . . 3_666 177.21(15) ?
C5 C4 N1 O1 . . . . -1.5(2) ?
C3 C4 N1 O1 . . . . 177.00(15) ?
C5 C4 N1 O2 . . . . 179.13(16) ?
C3 C4 N1 O2 . . . . -2.4(2) ?
C1 C7 N2 C9 . . . . -172.48(15) ?
C10 C9 N2 C7 . . . . -148.67(16) ?
C11 C9 N2 C7 . . . . 35.2(2) ?
