#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/02/2210237.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_2210237
loop_
_publ_author_name
'Arslan, Mustafa'
'Asker, Erol'
'Masnovi, John'
'Baker, Ronald J.'
_publ_section_title
(E,E)-1,3-Bis[9,10-dihydro-9-nitro-10-(trinitromethyl)-9-anthryl]propane
_journal_coeditor_code           GK2020
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3650
_journal_page_last               o3651
_journal_paper_doi               10.1107/S1600536806028698
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C33 H24 N8 O16'
_chemical_formula_moiety         'C33 H24 N8 O16'
_chemical_formula_sum            'C33 H24 N8 O16'
_chemical_formula_weight         788.6
_chemical_name_systematic
;
(E,E)-1,3-bis[9,10-dihydro-9-nitro-10-(trinitromethyl)-9-anthryl]propane
;
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 107.161(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.388(3)
_cell_length_b                   9.4054(10)
_cell_length_c                   16.3442(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      1
_cell_volume                     3435.2(6)
_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    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_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
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3049
_diffrn_reflns_theta_full        25.1
_diffrn_reflns_theta_max         25.1
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        2.6
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1771
_refine_ls_R_factor_gt           0.0613
_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)+(0.0444P)²+3.4205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                1481
_reflns_number_total             3049
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            gk2020.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2210237
_cod_database_fobs_code          2210237
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 0.38550(14) 0.8045(4) 0.31208(18) 0.0777(11) Uani d . 1
O O2 0.30784(15) 0.8765(4) 0.21623(19) 0.0812(12) Uani d . 1
O O3 0.49301(15) 0.7765(4) 0.0384(2) 0.0880(12) Uani d . 1
O O4 0.46533(15) 0.8915(4) -0.0819(2) 0.0802(11) Uani d . 1
O O5 0.44503(16) 0.5241(4) 0.0286(2) 0.0801(11) Uani d . 1
O O6 0.38763(18) 0.4765(4) -0.0978(2) 0.0910(13) Uani d . 1
O O7 0.42242(19) 0.6749(4) -0.1906(2) 0.0957(13) Uani d . 1
O O8 0.3366(2) 0.7694(5) -0.1968(2) 0.1071(15) Uani d . 1
N N1 0.46022(17) 0.7999(5) -0.0324(3) 0.0612(11) Uani d . 1
N N2 0.41419(19) 0.5563(4) -0.0422(3) 0.0579(10) Uani d . 1
N N3 0.3847(2) 0.7204(5) -0.1596(2) 0.0721(12) Uani d . 1
N N9 0.35752(17) 0.8250(4) 0.2384(2) 0.0499(9) Uani d . 1
C C1 0.40262(18) 1.0433(5) 0.1570(3) 0.0488(11) Uani d . 1
H H1 0.4133 1.047 0.2165 0.059 Uiso calc R 1
C C2 0.40281(18) 1.1662(5) 0.1122(3) 0.0543(12) Uani d . 1
H H2 0.4132 1.2519 0.1412 0.065 Uiso calc R 1
C C3 0.38775(17) 1.1629(5) 0.0247(3) 0.0521(12) Uani d . 1
H H3 0.3877 1.246 -0.006 0.063 Uiso calc R 1
C C4 0.37258(17) 1.0349(5) -0.0174(3) 0.0447(11) Uani d . 1
H H4 0.3626 1.0325 -0.0768 0.054 Uiso calc R 1
C C4A 0.37199(16) 0.9103(4) 0.0272(2) 0.0347(9) Uani d . 1
C C5 0.29068(17) 0.5598(4) -0.0184(3) 0.0468(11) Uani d . 1
H H5 0.2797 0.5596 -0.078 0.056 Uiso calc R 1
C C6 0.26868(18) 0.4566(5) 0.0229(3) 0.0583(12) Uani d . 1
H H6 0.2433 0.3868 -0.0083 0.07 Uiso calc R 1
C C7 0.28437(18) 0.4568(5) 0.1105(3) 0.0591(13) Uani d . 1
H H7 0.2702 0.3859 0.1391 0.071 Uiso calc R 1
C C8 0.32086(18) 0.5614(5) 0.1560(3) 0.0546(12) Uani d . 1
H H8 0.3307 0.5616 0.2154 0.065 Uiso calc R 1
C C8A 0.34339(15) 0.6667(4) 0.1152(2) 0.0360(10) Uani d . 1
C C9 0.38524(16) 0.7795(4) 0.1664(2) 0.0370(10) Uani d . 1
C C9A 0.38698(15) 0.9139(4) 0.1165(2) 0.0353(10) Uani d . 1
C C10 0.35313(16) 0.7746(4) -0.0220(2) 0.0387(10) Uani d . 1
H H10 0.3192 0.8006 -0.0712 0.046 Uiso calc R 1
C C10A 0.32911(15) 0.6652(4) 0.0264(2) 0.0366(9) Uani d . 1
C C11 0.44697(15) 0.7116(4) 0.2084(2) 0.0403(10) Uani d . 1
H H11A 0.4423 0.6455 0.2515 0.048 Uiso calc R 1
H H11B 0.4572 0.6558 0.1648 0.048 Uiso calc R 1
C C12 0.5 0.8047(6) 0.25 0.0438(15) Uani d S 1
H H12A 0.509 0.8651 0.2073 0.053 Uiso calc PR 0.5
H H12B 0.491 0.8651 0.2927 0.053 Uiso calc PR 0.5
C C13 0.40197(18) 0.7149(4) -0.0612(2) 0.0452(11) 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 '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
O3 N1 O4 . 127.7(5) n
O3 N1 C13 . 117.2(4) n
O4 N1 C13 . 114.9(4) n
O5 N2 O6 . 126.7(4) n
O5 N2 C13 . 117.4(4) n
O6 N2 C13 . 115.5(4) n
O8 N3 O7 . 127.5(4) n
O8 N3 C13 . 117.4(4) n
O7 N3 C13 . 115.1(4) n
O2 N9 O1 . 123.6(3) n
O2 N9 C9 . 117.3(3) n
O1 N9 C9 . 119.0(3) n
C2 C1 C9A . 122.0(4) n
C2 C1 H1 . 119 n
C9A C1 H1 . 119 n
C3 C2 C1 . 119.9(4) n
C3 C2 H2 . 120.1 n
C1 C2 H2 . 120.1 n
C2 C3 C4 . 119.4(4) n
C2 C3 H3 . 120.3 n
C4 C3 H3 . 120.3 n
C3 C4 C4A . 121.2(4) n
C3 C4 H4 . 119.4 n
C4A C4 H4 . 119.4 n
C9A C4A C4 . 119.4(4) n
C9A C4A C10 . 121.5(3) n
C4 C4A C10 . 119.0(3) n
C6 C5 C10A . 121.6(4) n
C6 C5 H5 . 119.2 n
C10A C5 H5 . 119.2 n
C7 C6 C5 . 119.5(4) n
C7 C6 H6 . 120.3 n
C5 C6 H6 . 120.3 n
C6 C7 C8 . 120.0(4) n
C6 C7 H7 . 120 n
C8 C7 H7 . 120 n
C8A C8 C7 . 121.2(4) n
C8A C8 H8 . 119.4 n
C7 C8 H8 . 119.4 n
C8 C8A C10A . 119.2(4) n
C8 C8A C9 . 120.7(3) n
C10A C8A C9 . 120.0(3) n
C8A C9 C9A . 113.8(3) y
C8A C9 N9 . 105.3(3) n
C9A C9 N9 . 105.1(3) n
C8A C9 C11 . 108.8(3) y
C9A C9 C11 . 114.5(3) y
N9 C9 C11 . 108.7(3) n
C4A C9A C1 . 118.1(4) n
C4A C9A C9 . 120.3(4) n
C1 C9A C9 . 121.6(3) n
C4A C10 C10A . 113.3(3) y
C4A C10 C13 . 112.8(3) n
C10A C10 C13 . 113.6(3) n
C4A C10 H10 . 105.4 n
C10A C10 H10 . 105.4 n
C13 C10 H10 . 105.4 n
C5 C10A C8A . 118.4(4) n
C5 C10A C10 . 119.6(3) n
C8A C10A C10 . 122.0(3) n
C12 C11 C9 . 119.9(3) n
C12 C11 H11A . 107.4 n
C9 C11 H11A . 107.4 n
C12 C11 H11B . 107.4 n
C9 C11 H11B . 107.3 n
H11A C11 H11B . 106.9 n
C11 C12 C11 2_655 108.9(4) n
C11 C12 H12A 2_655 109.9 n
C11 C12 H12A . 109.9 n
C11 C12 H12B 2_655 109.9 n
C11 C12 H12B . 109.9 n
H12A C12 H12B . 108.3 n
N2 C13 N1 . 110.5(3) n
N2 C13 C10 . 112.3(3) n
N1 C13 C10 . 112.2(3) n
N2 C13 N3 . 102.7(3) n
N1 C13 N3 . 103.9(3) n
C10 C13 N3 . 114.6(3) 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 N9 . 1.205(4) n
O2 N9 . 1.211(4) n
O3 N1 . 1.206(4) n
O4 N1 . 1.211(5) n
O5 N2 . 1.208(4) n
O6 N2 . 1.200(4) n
O7 N3 . 1.218(5) n
O8 N3 . 1.201(5) n
N1 C13 . 1.529(5) y
N2 C13 . 1.534(5) y
N3 C13 . 1.538(5) y
N9 C9 . 1.561(4) y
C1 C2 . 1.369(5) n
C1 C9A . 1.382(5) n
C1 H1 . 0.93 n
C2 C3 . 1.369(5) n
C2 H2 . 0.93 n
C3 C4 . 1.380(5) n
C3 H3 . 0.93 n
C4 C4A . 1.382(5) n
C4 H4 . 0.93 n
C4A C9A . 1.398(5) n
C4A C10 . 1.504(5) n
C5 C6 . 1.366(5) n
C5 C10A . 1.393(5) n
C5 H5 . 0.93 n
C6 C7 . 1.369(6) n
C6 H6 . 0.93 n
C7 C8 . 1.369(6) n
C7 H7 . 0.93 n
C8 C8A . 1.382(5) n
C8 H8 . 0.93 n
C8A C10A . 1.389(4) n
C8A C9 . 1.517(5) n
C9 C9A . 1.511(5) n
C9 C11 . 1.542(5) y
C10 C10A . 1.504(5) n
C10 C13 . 1.570(5) y
C10 H10 . 0.98 n
C11 C12 . 1.507(5) n
C11 H11A . 0.97 n
C11 H11B . 0.97 n
C12 C11 2_655 1.507(5) n
C12 H12A . 0.97 n
C12 H12B . 0.97 n
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 . -0.7(6) n
C1 C2 C3 C4 . -0.1(6) n
C2 C3 C4 C4A . 0.4(6) n
C3 C4 C4A C9A . 0.1(6) n
C3 C4 C4A C10 . 178.0(4) n
C10A C5 C6 C7 . 0.4(6) n
C5 C6 C7 C8 . 1.3(7) n
C6 C7 C8 C8A . -1.2(7) n
C7 C8 C8A C10A . -0.6(6) n
C7 C8 C8A C9 . -178.2(4) n
C8 C8A C9 C9A . -157.8(3) n
C10A C8A C9 C9A . 24.6(5) n
C8 C8A C9 N9 . -43.2(5) n
C10A C8A C9 N9 . 139.2(3) n
C8 C8A C9 C11 . 73.2(4) n
C10A C8A C9 C11 . -104.4(4) n
O2 N9 C9 C8A . -61.2(4) n
O1 N9 C9 C8A . 117.0(4) n
O2 N9 C9 C9A . 59.2(4) n
O1 N9 C9 C9A . -122.5(4) n
O2 N9 C9 C11 . -177.7(4) n
O1 N9 C9 C11 . 0.5(5) n
C4 C4A C9A C1 . -0.8(5) n
C10 C4A C9A C1 . -178.6(3) n
C4 C4A C9A C9 . 178.6(3) n
C10 C4A C9A C9 . 0.7(5) n
C2 C1 C9A C4A . 1.1(6) n
C2 C1 C9A C9 . -178.3(4) n
C8A C9 C9A C4A . -24.5(5) n
N9 C9 C9A C4A . -139.2(3) n
C11 C9 C9A C4A . 101.6(4) n
C8A C9 C9A C1 . 154.9(3) n
N9 C9 C9A C1 . 40.2(4) n
C11 C9 C9A C1 . -79.1(4) n
C9A C4A C10 C10A . 22.7(5) n
C4 C4A C10 C10A . -155.1(3) n
C9A C4A C10 C13 . -108.1(4) n
C4 C4A C10 C13 . 74.0(4) n
C6 C5 C10A C8A . -2.2(6) n
C6 C5 C10A C10 . 178.7(4) n
C8 C8A C10A C5 . 2.2(5) n
C9 C8A C10A C5 . 179.8(3) n
C8 C8A C10A C10 . -178.7(3) n
C9 C8A C10A C10 . -1.0(5) n
C4A C10 C10A C5 . 156.5(3) n
C13 C10 C10A C5 . -73.0(4) n
C4A C10 C10A C8A . -22.6(5) n
C13 C10 C10A C8A . 107.9(4) n
C8A C9 C11 C12 . 169.2(3) n
C9A C9 C11 C12 . 40.6(4) n
N9 C9 C11 C12 . -76.6(4) n
C9 C11 C12 C11 2_655 175.6(4) n
O5 N2 C13 N1 . 48.4(5) n
O6 N2 C13 N1 . -137.6(4) n
O5 N2 C13 C10 . -77.6(5) n
O6 N2 C13 C10 . 96.4(4) n
O5 N2 C13 N3 . 158.8(4) n
O6 N2 C13 N3 . -27.3(5) n
O3 N1 C13 N2 . -47.8(5) n
O4 N1 C13 N2 . 137.9(4) n
O3 N1 C13 C10 . 78.3(5) n
O4 N1 C13 C10 . -96.0(4) n
O3 N1 C13 N3 . -157.3(4) n
O4 N1 C13 N3 . 28.3(5) n
C4A C10 C13 N2 . 131.3(3) n
C10A C10 C13 N2 . 0.6(4) n
C4A C10 C13 N1 . 6.1(5) n
C10A C10 C13 N1 . -124.6(4) n
C4A C10 C13 N3 . -112.0(4) n
C10A C10 C13 N3 . 117.3(4) n
O8 N3 C13 N2 . 122.5(5) n
O7 N3 C13 N2 . -58.2(5) n
O8 N3 C13 N1 . -122.3(5) n
O7 N3 C13 N1 . 57.0(5) n
O8 N3 C13 C10 . 0.4(6) n
O7 N3 C13 C10 . 179.7(4) n
