#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/94/2209486.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_2209486
loop_
_publ_author_name
'Arslan, Mustafa'
'Asker, Erol'
'Masnovi, John'
'Baker, Ronald J.'
_publ_section_title
;
 10,10'-Dinitro-10,10'-(butane-1,4-diyl)dianthracen-9(10H)-one
;
_journal_coeditor_code           ER2009
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2819
_journal_page_last               o2821
_journal_paper_doi               10.1107/S160053680602157X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C32 H24 N2 O6'
_chemical_formula_moiety         'C32 H24 N2 O6'
_chemical_formula_sum            'C32 H24 N2 O6'
_chemical_formula_weight         532.53
_chemical_name_common
10,10'-Dinitro-10,10'-(butane-1,4-diyl)di-10H-anthracen-9-one
_chemical_name_systematic
;
10,10'-Dinitro-10,10'-(butane-1,4-diyl)dianthracen-9(10H)-one
;
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.728(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3160(10)
_cell_length_b                   8.3300(10)
_cell_length_c                   13.880(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      20.0
_cell_volume                     1296.5(3)
_computing_cell_refinement       'CAD-4/PC Software'
_computing_data_collection       'CAD-4/PC Software (Enraf-Nonius, 1993)'
_computing_data_reduction
'DATRD2 in NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_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  0.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2296
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.9
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.072
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0433P)²+0.4238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.096
_refine_ls_wR_factor_ref         0.110
_reflns_number_gt                1638
_reflns_number_total             2296
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er2009.cif
_cod_data_source_block           I
_cod_original_cell_volume        1296.6(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209486
_cod_database_fobs_code          2209486
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
O O1 0.06637(16) 0.2101(2) 0.80619(12) 0.0858(6) Uani d . 1
O O2 0.24334(15) 0.2982(2) 0.82085(12) 0.0854(6) Uani d . 1
O O9 0.48438(13) 0.2286(2) 0.54283(13) 0.0796(5) Uani d . 1
N N 0.15881(15) 0.2324(2) 0.77504(12) 0.0497(4) Uani d . 1
C C1 0.4565(2) -0.0539(3) 0.64346(17) 0.0651(7) Uani d . 1
H H1 0.524 -0.0432 0.6125 0.078 Uiso calc R 1
C C2 0.4420(2) -0.1881(3) 0.69632(18) 0.0765(8) Uani d . 1
H H2 0.4988 -0.2693 0.7003 0.092 Uiso calc R 1
C C3 0.3432(2) -0.2045(3) 0.74425(18) 0.0772(7) Uani d . 1
H H3 0.3345 -0.2957 0.7814 0.093 Uiso calc R 1
C C4 0.2574(2) -0.0851(3) 0.73693(16) 0.0625(6) Uani d . 1
H H4 0.191 -0.0962 0.7692 0.075 Uiso calc R 1
C C4A 0.27012(16) 0.0511(2) 0.68162(13) 0.0453(5) Uani d . 1
C C5 0.12032(18) 0.4543(2) 0.61030(15) 0.0527(5) Uani d . 1
H H5 0.0521 0.4466 0.6406 0.063 Uiso calc R 1
C C6 0.1405(2) 0.5918(3) 0.56053(17) 0.0638(6) Uani d . 1
H H6 0.0869 0.6767 0.5584 0.077 Uiso calc R 1
C C7 0.2398(2) 0.6041(3) 0.51388(18) 0.0680(6) Uani d . 1
H H7 0.2528 0.6965 0.4792 0.082 Uiso calc R 1
C C8 0.3192(2) 0.4805(3) 0.51862(16) 0.0606(6) Uani d . 1
H H8 0.3862 0.4892 0.4869 0.073 Uiso calc R 1
C C8A 0.30146(16) 0.3405(2) 0.57054(13) 0.0462(5) Uani d . 1
C C9 0.39230(17) 0.2126(3) 0.57908(14) 0.0533(5) Uani d . 1
C C9A 0.37151(16) 0.0677(3) 0.63519(14) 0.0491(5) Uani d . 1
C C10 0.17176(15) 0.1757(2) 0.66974(12) 0.0396(4) Uani d . 1
C C10A 0.19957(15) 0.3267(2) 0.61629(13) 0.0410(4) Uani d . 1
C C11 0.05311(15) 0.1013(2) 0.62416(13) 0.0400(4) Uani d . 1
H H11A 0.0326 0.0137 0.6649 0.048 Uiso calc R 1
H H11B -0.0093 0.1815 0.6219 0.048 Uiso calc R 1
C C12 0.05872(15) 0.0383(2) 0.52187(13) 0.0390(4) Uani d . 1
H H12A 0.0775 0.1263 0.4807 0.047 Uiso calc R 1
H H12B 0.1221 -0.0404 0.5239 0.047 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 '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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 '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
_geom_angle_publ_flag
O1 N O2 . 123.27(17) y
O1 N C10 . 119.15(16) y
O2 N C10 . 117.58(15) y
C2 C1 C9A . 120.8(2) n
C2 C1 H1 . 119.6 n
C9A C1 H1 . 119.6 n
C1 C2 C3 . 120.3(2) n
C1 C2 H2 . 119.8 n
C3 C2 H2 . 119.8 n
C4 C3 C2 . 119.9(2) n
C4 C3 H3 . 120.1 n
C2 C3 H3 . 120.1 n
C3 C4 C4A . 120.3(2) n
C3 C4 H4 . 119.9 n
C4A C4 H4 . 119.9 n
C9A C4A C4 . 119.27(19) n
C9A C4A C10 . 121.27(18) n
C4 C4A C10 . 119.42(18) n
C10A C5 C6 . 121.3(2) n
C10A C5 H5 . 119.3 n
C6 C5 H5 . 119.3 n
C7 C6 C5 . 120.1(2) n
C7 C6 H6 . 120 n
C5 C6 H6 . 120 n
C8 C7 C6 . 119.8(2) n
C8 C7 H7 . 120.1 n
C6 C7 H7 . 120.1 n
C7 C8 C8A . 121.0(2) n
C7 C8 H8 . 119.5 n
C8A C8 H8 . 119.5 n
C10A C8A C8 . 119.2(2) n
C10A C8A C9 . 120.99(18) n
C8 C8A C9 . 119.77(18) n
O9 C9 C8A . 120.8(2) n
O9 C9 C9A . 120.8(2) n
C8A C9 C9A . 118.40(17) n
C4A C9A C1 . 119.5(2) n
C4A C9A C9 . 121.66(18) n
C1 C9A C9 . 118.87(19) n
C4A C10 C10A . 115.12(15) y
C4A C10 C11 . 110.91(15) n
C10A C10 C11 . 111.18(15) n
C4A C10 N . 105.39(14) y
C10A C10 N . 105.02(14) y
C11 C10 N . 108.71(13) n
C5 C10A C8A . 118.55(18) n
C5 C10A C10 . 119.39(16) n
C8A C10A C10 . 122.03(17) n
C12 C11 C10 . 112.29(14) n
C12 C11 H11A . 109.1 n
C10 C11 H11A . 109.1 n
C12 C11 H11B . 109.1 n
C10 C11 H11B . 109.1 n
H11A C11 H11B . 107.9 n
C12 C12 C11 3_556 111.84(18) n
C12 C12 H12A 3_556 109.2 n
C11 C12 H12A . 109.2 n
C12 C12 H12B 3_556 109.2 n
C11 C12 H12B . 109.2 n
H12A C12 H12B . 107.9 n
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
O1 N . 1.199(2) y
O2 N . 1.207(2) y
O9 C9 . 1.224(2) y
N C10 . 1.562(2) y
C1 C2 . 1.359(4) n
C1 C9A . 1.390(3) n
C1 H1 . 0.93 n
C2 C3 . 1.382(4) n
C2 H2 . 0.93 n
C3 C4 . 1.384(3) n
C3 H3 . 0.93 n
C4 C4A . 1.388(3) n
C4 H4 . 0.93 n
C4A C9A . 1.396(3) n
C4A C10 . 1.515(3) n
C5 C10A . 1.386(3) n
C5 C6 . 1.372(3) n
C5 H5 . 0.93 n
C6 C7 . 1.375(3) n
C6 H6 . 0.93 n
C7 C8 . 1.362(3) n
C7 H7 . 0.93 n
C8 C8A . 1.400(3) n
C8 H8 . 0.93 n
C8A C10A . 1.394(2) n
C8A C9 . 1.474(3) n
C9 C9A . 1.473(3) n
C10 C10A . 1.515(3) n
C10 C11 . 1.536(2) n
C11 C12 . 1.523(2) n
C11 H11A . 0.97 n
C11 H11B . 0.97 n
C12 C12 3_556 1.525(3) n
C12 H12A . 0.97 n
C12 H12B . 0.97 n
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
C1 H1 O9 3_656 0.93 2.64 3.118(3) 112 y
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_4
_geom_torsion
_geom_torsion_publ_flag
C9A C1 C2 C3 . -1.2(4) n
C1 C2 C3 C4 . 1.2(4) n
C2 C3 C4 C4A . 0.0(4) n
C3 C4 C4A C9A . -1.3(3) n
C3 C4 C4A C10 . 176.42(19) n
C10A C5 C6 C7 . 1.1(3) n
C5 C6 C7 C8 . -1.1(4) n
C6 C7 C8 C8A . -0.1(3) n
C7 C8 C8A C10A . 1.3(3) n
C7 C8 C8A C9 . -176.5(2) n
C10A C8A C9 O9 . -176.35(19) n
C8 C8A C9 O9 . 1.4(3) n
C10A C8A C9 C9A . 1.5(3) n
C8 C8A C9 C9A . 179.29(18) n
C4 C4A C9A C1 . 1.4(3) n
C10 C4A C9A C1 . -176.31(17) n
C4 C4A C9A C9 . -177.30(18) n
C10 C4A C9A C9 . 5.0(3) n
C2 C1 C9A C4A . -0.2(3) n
C2 C1 C9A C9 . 178.6(2) n
O9 C9 C9A C4A . 176.39(19) n
C8A C9 C9A C4A . -1.5(3) n
O9 C9 C9A C1 . -2.3(3) n
C8A C9 C9A C1 . 179.81(17) n
C9A C4A C10 C10A . -7.9(2) n
C4 C4A C10 C10A . 174.35(17) n
C9A C4A C10 C11 . 119.38(18) n
C4 C4A C10 C11 . -58.3(2) n
C9A C4A C10 N . -123.15(18) n
C4 C4A C10 N . 59.1(2) n
O1 N C10 C4A . -117.6(2) n
O2 N C10 C4A . 63.0(2) n
O1 N C10 C10A . 120.46(19) n
O2 N C10 C10A . -59.0(2) n
O1 N C10 C11 . 1.4(2) y
O2 N C10 C11 . -178.02(18) y
C6 C5 C10A C8A . 0.1(3) n
C6 C5 C10A C10 . -178.34(19) n
C8 C8A C10A C5 . -1.3(3) n
C9 C8A C10A C5 . 176.49(17) n
C8 C8A C10A C10 . 177.10(17) n
C9 C8A C10A C10 . -5.1(3) n
C4A C10 C10A C5 . -173.55(17) n
C11 C10 C10A C5 . 59.3(2) n
N C10 C10A C5 . -58.1(2) n
C4A C10 C10A C8A . 8.1(2) n
C11 C10 C10A C8A . -119.13(18) n
N C10 C10A C8A . 123.48(17) n
C4A C10 C11 C12 . -63.0(2) n
C10A C10 C11 C12 . 66.42(19) n
N C10 C11 C12 . -178.46(15) n
C10 C11 C12 C12 3_556 178.83(18) n
