#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/35/2223544.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_2223544
loop_
_publ_author_name
'Miao, Shao-Bin'
'Deng, Dong-Sheng'
'Liu, Xian-Ming'
'Ji, Bao-Ming'
_publ_section_title
;
 2,2'-Dimethoxy-6,6'-dinitrobiphenyl
;
_journal_coeditor_code           SI2193
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2314
_journal_paper_doi               10.1107/S1600536809033790
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H12 N2 O6'
_chemical_formula_moiety         'C14 H12 N2 O6'
_chemical_formula_sum            'C14 H12 N2 O6'
_chemical_formula_weight         304.26
_chemical_name_systematic
;
2,2'-Dimethoxy-6,6'-dinitrobiphenyl
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.089(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.236(3)
_cell_length_b                   7.7826(12)
_cell_length_c                   10.9079(17)
_cell_measurement_reflns_used    1790
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.70
_cell_measurement_theta_min      2.47
_cell_volume                     1402.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5102
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.9663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0352
_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)+(0.0401P)²+0.8036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                1009
_reflns_number_total             1298
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2193.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2223544
_cod_database_fobs_code          2223544
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.49134(9) 0.22562(19) 0.67636(14) 0.0387(4) Uani d . 1 . .
C C2 0.54245(9) 0.2962(2) 0.62577(15) 0.0434(4) Uani d . 1 . .
C C3 0.52777(12) 0.2896(2) 0.49065(17) 0.0546(5) Uani d . 1 . .
H H3 0.5639 0.3378 0.4607 0.066 Uiso calc R 1 . .
C C4 0.45847(12) 0.2102(2) 0.40223(17) 0.0588(5) Uani d . 1 . .
H H4 0.4471 0.2058 0.3107 0.071 Uiso calc R 1 . .
C C5 0.40569(11) 0.1370(2) 0.44656(16) 0.0540(5) Uani d . 1 . .
H H5 0.3589 0.0835 0.3852 0.065 Uiso calc R 1 . .
C C6 0.42203(9) 0.1426(2) 0.58296(15) 0.0444(4) Uani d . 1 . .
C C7 0.30000(13) -0.0071(4) 0.5464(2) 0.0944(8) Uani d . 1 . .
H H7A 0.2673 0.0767 0.4817 0.142 Uiso calc R 1 . .
H H7B 0.2716 -0.0485 0.5971 0.142 Uiso calc R 1 . .
H H7C 0.3110 -0.1012 0.4998 0.142 Uiso calc R 1 . .
N N1 0.61559(9) 0.3880(2) 0.71661(15) 0.0557(4) Uani d . 1 . .
O O1 0.37432(7) 0.06986(18) 0.63620(11) 0.0594(4) Uani d . 1 . .
O O2 0.61327(8) 0.47507(17) 0.80791(13) 0.0615(4) Uani d . 1 . .
O O3 0.67594(9) 0.3739(3) 0.69543(17) 0.0967(6) Uani d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0399(8) 0.0425(8) 0.0345(8) 0.0057(6) 0.0166(7) 0.0011(6)
C2 0.0464(9) 0.0454(9) 0.0426(8) 0.0044(7) 0.0229(7) 0.0023(7)
C3 0.0722(12) 0.0549(10) 0.0508(10) 0.0071(9) 0.0399(9) 0.0053(8)
C4 0.0853(14) 0.0566(11) 0.0369(8) 0.0117(10) 0.0283(10) 0.0036(8)
C5 0.0610(11) 0.0545(10) 0.0372(8) 0.0046(9) 0.0119(8) -0.0031(8)
C6 0.0452(9) 0.0473(9) 0.0388(8) 0.0033(7) 0.0159(7) 0.0004(7)
C7 0.0600(13) 0.142(2) 0.0750(14) -0.0445(14) 0.0224(12) -0.0253(15)
N1 0.0500(8) 0.0679(10) 0.0571(9) -0.0031(7) 0.0302(7) 0.0073(8)
O1 0.0473(7) 0.0794(9) 0.0474(7) -0.0193(6) 0.0162(6) -0.0058(6)
O2 0.0612(8) 0.0665(8) 0.0570(7) -0.0133(6) 0.0253(6) -0.0081(7)
O3 0.0604(9) 0.1503(16) 0.0999(12) -0.0197(10) 0.0538(9) -0.0120(11)
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 . . 116.51(13) ?
C2 C1 C1 . 2_656 123.77(15) ?
C6 C1 C1 . 2_656 119.63(14) ?
C1 C2 C3 . . 123.51(15) ?
C1 C2 N1 . . 119.86(13) ?
C3 C2 N1 . . 116.60(14) ?
C4 C3 C2 . . 118.11(16) ?
C4 C3 H3 . . 120.9 ?
C2 C3 H3 . . 120.9 ?
C3 C4 C5 . . 121.01(15) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C4 C5 C6 . . 120.08(17) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
O1 C6 C5 . . 124.06(15) ?
O1 C6 C1 . . 115.19(13) ?
C5 C6 C1 . . 120.75(15) ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 N1 O3 . . 123.39(16) ?
O2 N1 C2 . . 119.06(13) ?
O3 N1 C2 . . 117.55(16) ?
C6 O1 C7 . . 118.46(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 . 1.400(2) ?
C1 C1 2_656 1.500(3) ?
C2 C3 . 1.383(2) ?
C2 N1 . 1.466(2) ?
C3 C4 . 1.370(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.371(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.389(2) ?
C5 H5 . 0.9300 ?
C6 O1 . 1.3576(19) ?
C7 O1 . 1.424(2) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
N1 O2 . 1.2200(18) ?
N1 O3 . 1.2217(18) ?
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
C7 H7B O3 3_445 0.96 2.48 3.426(3) 169
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 . . . . 0.7(2) ?
C1 C1 C2 C3 2_656 . . . 177.26(13) ?
C6 C1 C2 N1 . . . . 178.92(14) ?
C1 C1 C2 N1 2_656 . . . -4.5(2) ?
C1 C2 C3 C4 . . . . 0.6(3) ?
N1 C2 C3 C4 . . . . -177.73(16) ?
C2 C3 C4 C5 . . . . -0.9(3) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C4 C5 C6 O1 . . . . -178.25(16) ?
C4 C5 C6 C1 . . . . 1.3(3) ?
C2 C1 C6 O1 . . . . 178.01(14) ?
C1 C1 C6 O1 2_656 . . . 1.26(19) ?
C2 C1 C6 C5 . . . . -1.6(2) ?
C1 C1 C6 C5 2_656 . . . -178.36(13) ?
C1 C2 N1 O2 . . . . -36.5(2) ?
C3 C2 N1 O2 . . . . 141.90(16) ?
C1 C2 N1 O3 . . . . 144.16(17) ?
C3 C2 N1 O3 . . . . -37.5(2) ?
C5 C6 O1 C7 . . . . -4.5(3) ?
C1 C6 O1 C7 . . . . 175.90(18) ?
