#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/25/2232514.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_2232514
loop_
_publ_author_name
'Wang, Wen-Yan'
'Diao, Ying'
'Wei, Zhi-Hua'
'Wang, Jian-Long'
_publ_section_title
;
 1,2-Bis(2,4,6-trinitrophenyl)ethane
;
_journal_coeditor_code           XU5348
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3044
_journal_paper_doi               10.1107/S1600536811042802
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H8 N6 O12'
_chemical_formula_moiety         'C14 H8 N6 O12'
_chemical_formula_sum            'C14 H8 N6 O12'
_chemical_formula_weight         452.26
_chemical_name_systematic
;
1,2-Bis(2,4,6-trinitrophenyl)ethane
;
_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                 97.154(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.8468(5)
_cell_length_b                   8.1253(11)
_cell_length_c                   17.977(2)
_cell_measurement_reflns_used    3228
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.3
_cell_volume                     847.38(17)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2000)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2000)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7531
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.245
_refine_ls_extinction_coef       0.025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2013
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0343
_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)+(0.0569P)²+0.0176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                1503
_reflns_number_total             2013
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5348.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232514
_cod_database_fobs_code          2232514
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.788(2) 0.4687(13) 0.1645(5) 0.0296(16) Uani d PDU 0.513(3) 1 A 1
O O1 0.8771(5) 0.5628(3) 0.12216(13) 0.0302(6) Uani d PDU 0.513(3) 1 A 1
O O2 0.815(3) 0.489(2) 0.2328(6) 0.0260(15) Uani d PDU 0.513(3) 1 A 1
N N1' 0.824(2) 0.4472(14) 0.1631(5) 0.0296(16) Uani d PDU 0.487(3) 1 A 2
O O1' 0.9430(5) 0.4872(4) 0.11433(14) 0.0355(7) Uani d PDU 0.487(3) 1 A 2
O O2' 0.822(3) 0.503(2) 0.2263(7) 0.035(3) Uani d PDU 0.487(3) 1 A 2
O O3 0.72410(17) -0.11091(14) 0.26187(5) 0.0387(3) Uani d . 1 1 . .
O O4 0.48405(19) -0.23368(11) 0.17726(5) 0.0344(3) Uani d . 1 1 . .
N N3 0.15225(18) 0.19328(12) 0.00293(5) 0.0229(3) Uani d D 1 1 . .
O O5 -0.0105(3) 0.2748(3) 0.01446(10) 0.0295(6) Uani d PDU 0.513(3) 1 A 1
O O6 0.1555(3) 0.0949(3) -0.04988(9) 0.0301(7) Uani d PDU 0.513(3) 1 A 1
O O5' -0.0438(3) 0.1733(4) 0.01768(11) 0.0328(6) Uani d PDU 0.487(3) 1 A 2
O O6' 0.2022(4) 0.2111(3) -0.06168(10) 0.0345(7) Uani d PDU 0.487(3) 1 A 2
N N2 0.59258(19) -0.11271(15) 0.20272(6) 0.0299(3) Uani d . 1 1 . .
C C1 0.4345(2) 0.49440(15) 0.03484(6) 0.0222(3) Uani d . 1 1 . .
H H1A 0.4797 0.5885 0.0685 0.027 Uiso calc R 1 1 . .
H H1B 0.2668 0.5029 0.0185 0.027 Uiso calc R 1 1 . .
C C2 0.4834(2) 0.33521(15) 0.07792(6) 0.0226(3) Uani d . 1 1 . .
C C3 0.6575(2) 0.31668(17) 0.13844(6) 0.0267(3) Uani d D 1 1 A .
C C4 0.6978(2) 0.17462(17) 0.18056(6) 0.0271(3) Uani d . 1 1 . .
H H4 0.8168 0.1692 0.2216 0.033 Uiso calc R 1 1 A .
C C5 0.5584(2) 0.04194(16) 0.16040(7) 0.0263(3) Uani d . 1 1 A .
C C6 0.3810(2) 0.04812(17) 0.10198(7) 0.0268(3) Uani d . 1 1 . .
H H6 0.2850 -0.0445 0.0892 0.032 Uiso calc R 1 1 A .
C C7 0.3490(2) 0.19428(16) 0.06306(6) 0.0229(3) Uani d . 1 1 A .
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
O2 N1 O1 . . 121.2(11)
O2 N1 C3 . . 114.9(9)
O1 N1 C3 . . 123.7(6)
O2' N1' O1' . . 129.5(12)
O2' N1' C3 . . 117.6(10)
O1' N1' C3 . . 112.9(6)
O5 N3 O5' . . 41.21(12)
O5 N3 O6' . . 112.46(16)
O5' N3 O6' . . 123.81(15)
O5 N3 O6 . . 125.15(16)
O5' N3 O6 . . 100.65(16)
O6' N3 O6 . . 48.11(12)
O5 N3 C7 . . 115.66(13)
O5' N3 C7 . . 120.60(13)
O6' N3 C7 . . 115.58(13)
O6 N3 C7 . . 118.54(12)
O4 N2 O3 . . 124.71(11)
O4 N2 C5 . . 117.46(10)
O3 N2 C5 . . 117.81(11)
C2 C1 C1 . 3_665 112.47(13)
C2 C1 H1A . . 109.1
C1 C1 H1A 3_665 . 109.1
C2 C1 H1B . . 109.1
C1 C1 H1B 3_665 . 109.1
H1A C1 H1B . . 107.8
C7 C2 C3 . . 113.41(11)
C7 C2 C1 . . 122.43(10)
C3 C2 C1 . . 124.07(11)
C4 C3 C2 . . 124.86(12)
C4 C3 N1' . . 112.0(6)
C2 C3 N1' . . 123.1(6)
C4 C3 N1 . . 118.2(5)
C2 C3 N1 . . 116.5(5)
N1' C3 N1 . . 10.7(11)
C5 C4 C3 . . 117.07(11)
C5 C4 H4 . . 121.5
C3 C4 H4 . . 121.5
C4 C5 C6 . . 122.48(11)
C4 C5 N2 . . 119.78(11)
C6 C5 N2 . . 117.73(12)
C7 C6 C5 . . 117.28(12)
C7 C6 H6 . . 121.4
C5 C6 H6 . . 121.4
C6 C7 C2 . . 124.88(11)
C6 C7 N3 . . 114.24(11)
C2 C7 N3 . . 120.87(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 O2 . 1.231(8)
N1 O1 . 1.238(7)
N1 C3 . 1.496(7)
N1' O2' . 1.226(8)
N1' O1' . 1.228(8)
N1' C3 . 1.471(7)
O3 N2 . 1.2323(13)
O4 N2 . 1.2271(15)
N3 O5 . 1.199(2)
N3 O5' . 1.219(2)
N3 O6' . 1.241(2)
N3 O6 . 1.243(2)
N3 C7 . 1.4772(14)
N2 C5 . 1.4697(16)
C1 C2 . 1.5164(16)
C1 C1 3_665 1.550(2)
C1 H1A . 0.9900
C1 H1B . 0.9900
C2 C7 . 1.3957(17)
C2 C3 . 1.4024(16)
C3 C4 . 1.3846(18)
C4 C5 . 1.3728(19)
C4 H4 . 0.9500
C5 C6 . 1.3820(17)
C6 C7 . 1.3792(18)
C6 H6 . 0.9500
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
C1 H1A O4 1_565 0.99 2.43 3.3669(15) 158
C1 H1B O5 3_565 0.99 2.37 3.147(2) 134
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
C1 C1 C2 C7 3_665 -90.86(16)
C1 C1 C2 C3 3_665 92.64(16)
C7 C2 C3 C4 . 0.13(18)
C1 C2 C3 C4 . 176.91(12)
C7 C2 C3 N1' . 178.3(5)
C1 C2 C3 N1' . -4.9(5)
C7 C2 C3 N1 . -172.0(4)
C1 C2 C3 N1 . 4.8(5)
O2' N1' C3 C4 . -64.8(15)
O1' N1' C3 C4 . 117.4(9)
O2' N1' C3 C2 . 116.8(13)
O1' N1' C3 C2 . -61.0(13)
O2' N1' C3 N1 . 62(4)
O1' N1' C3 N1 . -116(5)
O2 N1 C3 C4 . -38.7(14)
O1 N1 C3 C4 . 136.6(10)
O2 N1 C3 C2 . 134.0(11)
O1 N1 C3 C2 . -50.7(13)
O2 N1 C3 N1' . -96(4)
O1 N1 C3 N1' . 79(3)
C2 C3 C4 C5 . 1.1(2)
N1' C3 C4 C5 . -177.3(5)
N1 C3 C4 C5 . 173.0(5)
C3 C4 C5 C6 . -1.5(2)
C3 C4 C5 N2 . 179.85(11)
O4 N2 C5 C4 . -171.13(12)
O3 N2 C5 C4 . 10.35(18)
O4 N2 C5 C6 . 10.15(18)
O3 N2 C5 C6 . -168.36(12)
C4 C5 C6 C7 . 0.7(2)
N2 C5 C6 C7 . 179.42(11)
C5 C6 C7 C2 . 0.6(2)
C5 C6 C7 N3 . -178.30(11)
C3 C2 C7 C6 . -0.98(18)
C1 C2 C7 C6 . -177.82(12)
C3 C2 C7 N3 . 177.83(10)
C1 C2 C7 N3 . 0.99(18)
O5 N3 C7 C6 . 109.24(19)
O5' N3 C7 C6 . 62.5(2)
O6' N3 C7 C6 . -116.35(17)
O6 N3 C7 C6 . -61.96(18)
O5 N3 C7 C2 . -69.7(2)
O5' N3 C7 C2 . -116.4(2)
O6' N3 C7 C2 . 64.72(19)
O6 N3 C7 C2 . 119.11(17)
