#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/55/2215575.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_2215575
loop_
_publ_author_name
'Xue-Yang Xiao'
'Shao-Bin Miao'
'Hong-Hong Lan'
'Yuan-Yuan Jiang'
'Bao-Ming Ji'
_publ_section_title
;
 6,6'-Dimethoxy-2,3,2',5'-tetranitro-1,1'-biphenyl
;
_journal_coeditor_code           LH2441
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4012
_journal_page_last               o4012
_journal_paper_doi               10.1107/S1600536807040202
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H10 N4 O10'
_chemical_formula_moiety         'C14 H10 N4 O10'
_chemical_formula_sum            'C14 H10 N4 O10'
_chemical_formula_weight         394.26
_chemical_name_systematic
;
6,6'-Dimethoxy-2,3,2',5'-tetranitro-1,1'-biphenyl
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.118(2)
_cell_angle_beta                 90.579(2)
_cell_angle_gamma                110.977(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1821(11)
_cell_length_b                   10.2161(13)
_cell_length_c                   10.6133(14)
_cell_measurement_reflns_used    1810
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      23.51
_cell_measurement_theta_min      2.67
_cell_volume                     824.21(19)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX II 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  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6347
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_correction_T_min  0.9133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0459
_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)+(0.06P)²+0.3203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                2173
_reflns_number_total             3051
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2441.cif
_cod_data_source_block           I
_cod_database_code               2215575
_cod_database_fobs_code          2215575
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.5521(2) 0.38404(17) 0.32635(15) 0.0544(5) Uani d . 1
O O2 0.1047(4) -0.2166(3) 0.4665(3) 0.1216(11) Uani d U 1
O O3 -0.0829(3) -0.1796(2) 0.3485(2) 0.0847(7) Uani d U 1
O O4 0.0530(3) -0.1066(2) 0.1089(2) 0.0836(7) Uani d U 1
O O5 -0.0687(3) 0.0425(2) 0.1627(3) 0.0909(8) Uani d U 1
O O6 0.1341(3) 0.3722(2) 0.32138(19) 0.0735(6) Uani d U 1
O O7 0.0125(3) 0.4502(3) 0.1823(2) 0.0864(7) Uani d U 1
O O8 0.5697(3) 0.3399(2) -0.2476(2) 0.0972(8) Uani d U 1
O O9 0.4681(3) 0.1229(2) -0.2111(2) 0.0861(7) Uani d U 1
O O10 0.4716(2) 0.13198(17) 0.05720(16) 0.0505(4) Uani d . 1
N N1 0.0619(3) -0.1446(2) 0.3991(2) 0.0620(6) Uani d . 1
N N2 0.0430(3) -0.0071(2) 0.1743(2) 0.0520(5) Uani d . 1
N N3 0.1122(3) 0.3936(2) 0.2140(2) 0.0504(5) Uani d . 1
N N4 0.4869(3) 0.2450(3) -0.1846(2) 0.0614(6) Uani d . 1
C C1 0.4371(3) 0.2571(2) 0.3497(2) 0.0416(5) Uani d . 1
C C2 0.4469(3) 0.1889(3) 0.4556(2) 0.0502(6) Uani d . 1
H H2 0.5365 0.2319 0.5171 0.060 Uiso calc R 1
C C3 0.3246(3) 0.0579(3) 0.4698(2) 0.0522(6) Uani d . 1
H H3 0.3322 0.0127 0.5407 0.063 Uiso calc R 1
C C4 0.1917(3) -0.0063(2) 0.3801(2) 0.0446(6) Uani d . 1
C C5 0.1809(3) 0.0619(2) 0.2745(2) 0.0384(5) Uani d . 1
C C6 0.3011(3) 0.1926(2) 0.25653(19) 0.0364(5) Uani d . 1
C C7 0.2998(3) 0.2600(2) 0.13651(19) 0.0357(5) Uani d . 1
C C8 0.2142(3) 0.3520(2) 0.1146(2) 0.0406(5) Uani d . 1
C C9 0.2197(3) 0.4097(3) 0.0016(2) 0.0488(6) Uani d . 1
H H9 0.1601 0.4704 -0.0098 0.059 Uiso calc R 1
C C10 0.3139(3) 0.3768(3) -0.0940(2) 0.0520(7) Uani d . 1
H H10 0.3219 0.4173 -0.1699 0.062 Uiso calc R 1
C C11 0.3963(3) 0.2837(2) -0.0768(2) 0.0443(6) Uani d . 1
C C12 0.3931(3) 0.2246(2) 0.0373(2) 0.0395(5) Uani d . 1
C C13 0.6577(4) 0.1862(3) 0.0691(4) 0.0756(9) Uani d . 1
H H13A 0.7046 0.2154 -0.0106 0.113 Uiso calc R 1
H H13B 0.6981 0.1144 0.0936 0.113 Uiso calc R 1
H H13C 0.6961 0.2655 0.1323 0.113 Uiso calc R 1
C C14 0.6954(4) 0.4544(3) 0.4180(3) 0.0752(9) Uani d . 1
H H14A 0.6497 0.4677 0.4991 0.113 Uiso calc R 1
H H14B 0.7652 0.5443 0.3916 0.113 Uiso calc R 1
H H14C 0.7665 0.3979 0.4240 0.113 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 0.0016 '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
C1 O1 C14 117.70(19)
C12 O10 C13 116.79(19)
O2 N1 O3 123.6(2)
O2 N1 C4 117.7(2)
O3 N1 C4 118.7(2)
O5 N2 O4 125.2(2)
O5 N2 C5 117.1(2)
O4 N2 C5 117.7(2)
O6 N3 O7 123.7(2)
O6 N3 C8 118.7(2)
O7 N3 C8 117.6(2)
O9 N4 O8 123.6(2)
O9 N4 C11 119.4(2)
O8 N4 C11 116.8(2)
O1 C1 C2 124.6(2)
O1 C1 C6 115.30(19)
C2 C1 C6 120.1(2)
C3 C2 C1 120.3(2)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C3 C2 120.4(2)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 119.5(2)
C3 C4 N1 119.0(2)
C5 C4 N1 121.5(2)
C6 C5 C4 121.9(2)
C6 C5 N2 117.51(18)
C4 C5 N2 120.5(2)
C5 C6 C1 117.90(19)
C5 C6 C7 121.83(18)
C1 C6 C7 120.03(19)
C8 C7 C12 117.51(19)
C8 C7 C6 126.4(2)
C12 C7 C6 116.11(19)
C9 C8 C7 122.9(2)
C9 C8 N3 116.4(2)
C7 C8 N3 120.8(2)
C10 C9 C8 119.3(2)
C10 C9 H9 120.4
C8 C9 H9 120.4
C9 C10 C11 119.4(2)
C9 C10 H10 120.3
C11 C10 H10 120.3
C10 C11 C12 122.2(2)
C10 C11 N4 117.5(2)
C12 C11 N4 120.4(2)
O10 C12 C11 123.7(2)
O10 C12 C7 117.54(19)
C11 C12 C7 118.7(2)
O10 C13 H13A 109.5
O10 C13 H13B 109.5
H13A C13 H13B 109.5
O10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O1 C14 H14A 109.5
O1 C14 H14B 109.5
H14A C14 H14B 109.5
O1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.348(3)
O1 C14 1.444(3)
O2 N1 1.203(3)
O3 N1 1.212(3)
O4 N2 1.206(3)
O5 N2 1.204(3)
O6 N3 1.203(3)
O7 N3 1.216(3)
O8 N4 1.225(3)
O9 N4 1.208(3)
O10 C12 1.349(3)
O10 C13 1.422(3)
N1 C4 1.465(3)
N2 C5 1.474(3)
N3 C8 1.478(3)
N4 C11 1.471(3)
C1 C2 1.391(3)
C1 C6 1.410(3)
C2 C3 1.376(4)
C2 H2 0.9300
C3 C4 1.370(3)
C3 H3 0.9300
C4 C5 1.389(3)
C5 C6 1.377(3)
C6 C7 1.503(3)
C7 C8 1.391(3)
C7 C12 1.402(3)
C8 C9 1.377(3)
C9 C10 1.370(4)
C9 H9 0.9300
C10 C11 1.371(3)
C10 H10 0.9300
C11 C12 1.397(3)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 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
C13 H13B O5 1_655 0.96 2.41 3.274(4) 150.3
C14 H14A O6 2_666 0.96 2.60 3.165(3) 118.2
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
C14 O1 C1 C2 -0.1(4)
C14 O1 C1 C6 -179.3(2)
O1 C1 C2 C3 -178.8(2)
C6 C1 C2 C3 0.3(4)
C1 C2 C3 C4 -0.3(4)
C2 C3 C4 C5 -0.1(4)
C2 C3 C4 N1 -178.9(2)
O2 N1 C4 C3 -24.1(4)
O3 N1 C4 C3 154.7(3)
O2 N1 C4 C5 157.1(3)
O3 N1 C4 C5 -24.1(4)
C3 C4 C5 C6 0.5(4)
N1 C4 C5 C6 179.3(2)
C3 C4 C5 N2 177.7(2)
N1 C4 C5 N2 -3.5(4)
O5 N2 C5 C6 -70.8(3)
O4 N2 C5 C6 107.7(3)
O5 N2 C5 C4 111.9(3)
O4 N2 C5 C4 -69.7(3)
C4 C5 C6 C1 -0.4(3)
N2 C5 C6 C1 -177.7(2)
C4 C5 C6 C7 173.9(2)
N2 C5 C6 C7 -3.5(3)
O1 C1 C6 C5 179.2(2)
C2 C1 C6 C5 0.0(3)
O1 C1 C6 C7 4.8(3)
C2 C1 C6 C7 -174.4(2)
C5 C6 C7 C8 92.6(3)
C1 C6 C7 C8 -93.3(3)
C5 C6 C7 C12 -86.7(3)
C1 C6 C7 C12 87.5(3)
C12 C7 C8 C9 -0.9(3)
C6 C7 C8 C9 179.9(2)
C12 C7 C8 N3 179.59(18)
C6 C7 C8 N3 0.3(3)
O6 N3 C8 C9 -163.8(2)
O7 N3 C8 C9 14.9(3)
O6 N3 C8 C7 15.8(3)
O7 N3 C8 C7 -165.5(2)
C7 C8 C9 C10 -0.4(3)
N3 C8 C9 C10 179.2(2)
C8 C9 C10 C11 2.0(3)
C9 C10 C11 C12 -2.4(3)
C9 C10 C11 N4 176.4(2)
O9 N4 C11 C10 -134.9(3)
O8 N4 C11 C10 40.7(3)
O9 N4 C11 C12 43.9(3)
O8 N4 C11 C12 -140.5(3)
C13 O10 C12 C11 72.0(3)
C13 O10 C12 C7 -109.6(3)
C10 C11 C12 O10 179.5(2)
N4 C11 C12 O10 0.7(3)
C10 C11 C12 C7 1.2(3)
N4 C11 C12 C7 -177.63(19)
C8 C7 C12 O10 -177.95(18)
C6 C7 C12 O10 1.4(3)
C8 C7 C12 C11 0.5(3)
C6 C7 C12 C11 179.82(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123315
