#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/04/2210422.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_2210422
loop_
_publ_author_name
'Butt, M. Saeed'
'Akhter, Zareen'
'Bolte, Michael'
'Siddiqi, Humaira M.'
_publ_section_title
;
 1,4-Bis(4-nitrophenoxy)benzene
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3992
_journal_page_last               o3993
_journal_paper_doi               10.1107/S1600536806032326
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H12 N2 O6'
_chemical_formula_moiety         'C18 H12 N2 O6'
_chemical_formula_sum            'C18 H12 N2 O6'
_chemical_formula_weight         352.30
_chemical_melting_point          238
_chemical_name_common            1,4-bis(4-nitrophenoxy)benzene
_chemical_name_systematic
;
1,4-bis(4-nitrophenoxy)benzene
;
_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                91.973(7)
_cell_angle_beta                 106.497(7)
_cell_angle_gamma                110.152(6)
_cell_formula_units_Z            2
_cell_length_a                   7.2861(6)
_cell_length_b                   10.1381(9)
_cell_length_c                   12.0838(11)
_cell_measurement_reflns_used    17691
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.6
_cell_volume                     794.74(13)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Stoe IPDS-II two-circle'
_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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18200
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         3.56
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.185
_refine_ls_extinction_coef       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0415
_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)+(0.0545P)²+0.2087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                3064
_reflns_number_total             3644
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww2044.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_cell_volume        794.74(12)
_cod_database_code               2210422
_cod_database_fobs_code          2210422
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 0.14779(15) 0.80747(10) 0.11671(8) 0.0338(2) Uani d . 1
N N1 0.78574(17) 0.94769(13) 0.54132(9) 0.0296(2) Uani d . 1
C C1 0.30488(18) 0.85081(13) 0.22210(10) 0.0243(2) Uani d . 1
C C2 0.4658(2) 0.98324(14) 0.24912(12) 0.0313(3) Uani d . 1
H H2 0.4673 1.0505 0.1963 0.038 Uiso calc R 1
C C3 0.6243(2) 1.01528(14) 0.35473(12) 0.0296(3) Uani d . 1
H H3 0.7346 1.1050 0.3751 0.035 Uiso calc R 1
C C4 0.61885(18) 0.91429(13) 0.42987(10) 0.0240(2) Uani d . 1
C C5 0.45993(19) 0.78210(14) 0.40322(11) 0.0255(3) Uani d . 1
H H5 0.4602 0.7144 0.4557 0.031 Uiso calc R 1
C C6 0.30028(19) 0.75037(13) 0.29843(11) 0.0255(3) Uani d . 1
H H6 0.1891 0.6611 0.2790 0.031 Uiso calc R 1
O O11 0.79566(18) 0.85029(13) 0.59845(9) 0.0435(3) Uani d . 1
O O12 0.90903(15) 1.07143(11) 0.57310(9) 0.0381(3) Uani d . 1
C C11 0.08101(18) 0.90985(13) 0.06053(11) 0.0257(3) Uani d . 1
C C12 0.0635(2) 0.90984(14) -0.05716(11) 0.0281(3) Uani d . 1
H H12 0.1071 0.8483 -0.0953 0.034 Uiso calc R 1
C C13 -0.0186(2) 1.00122(14) -0.11846(11) 0.0287(3) Uani d . 1
H H13 -0.0317 1.0027 -0.1989 0.034 Uiso calc R 1
O O1A 0.59391(16) 0.43120(14) 0.36471(11) 0.0536(4) Uani d . 1
N N1A 0.3508(2) 0.67143(16) -0.03318(11) 0.0406(3) Uani d . 1
C C1A 0.5467(2) 0.49469(15) 0.26699(12) 0.0309(3) Uani d . 1
C C2A 0.68091(19) 0.62226(14) 0.24903(12) 0.0292(3) Uani d . 1
H H2A 0.8146 0.6686 0.3036 0.035 Uiso calc R 1
C C3A 0.6151(2) 0.68010(14) 0.14967(12) 0.0300(3) Uani d . 1
H H3A 0.7031 0.7672 0.1355 0.036 Uiso calc R 1
C C4A 0.4190(2) 0.60919(15) 0.07120(11) 0.0291(3) Uani d . 1
C C5A 0.2849(2) 0.48138(15) 0.08789(12) 0.0324(3) Uani d . 1
H H5A 0.1521 0.4345 0.0326 0.039 Uiso calc R 1
C C6A 0.3504(2) 0.42418(15) 0.18759(13) 0.0353(3) Uani d . 1
H H6A 0.2618 0.3373 0.2017 0.042 Uiso calc R 1
O O11A 0.4690(2) 0.78570(17) -0.04620(13) 0.0668(4) Uani d . 1
O O12A 0.1781(2) 0.60780(15) -0.10325(9) 0.0521(3) Uani d . 1
C C11A 0.8013(2) 0.46948(15) 0.43081(12) 0.0334(3) Uani d . 1
C C12A 0.8704(2) 0.55025(15) 0.53978(13) 0.0357(3) Uani d . 1
H H12A 0.7814 0.5842 0.5661 0.043 Uiso calc R 1
C C13A 1.0724(2) 0.58088(15) 0.61013(12) 0.0366(3) Uani d . 1
H H13A 1.1229 0.6356 0.6853 0.044 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_site_symmetry_1
_geom_angle
C1 O1 C11 . 118.85(9)
O12 N1 O11 . 123.24(11)
O12 N1 C4 . 118.48(11)
O11 N1 C4 . 118.28(11)
O1 C1 C6 . 115.75(11)
O1 C1 C2 . 122.82(11)
C6 C1 C2 . 121.33(11)
C3 C2 C1 . 119.09(12)
C3 C2 H2 . 120.5
C1 C2 H2 . 120.5
C4 C3 C2 . 119.15(12)
C4 C3 H3 . 120.4
C2 C3 H3 . 120.4
C5 C4 C3 . 122.05(11)
C5 C4 N1 . 118.64(11)
C3 C4 N1 . 119.31(11)
C4 C5 C6 . 118.94(11)
C4 C5 H5 . 120.5
C6 C5 H5 . 120.5
C5 C6 C1 . 119.44(11)
C5 C6 H6 . 120.3
C1 C6 H6 . 120.3
C13 C11 C12 2_575 121.59(12)
C13 C11 O1 2_575 120.77(12)
C12 C11 O1 . 117.42(11)
C11 C12 C13 . 119.24(12)
C11 C12 H12 . 120.4
C13 C12 H12 . 120.4
C11 C13 C12 2_575 119.17(12)
C11 C13 H13 2_575 120.4
C12 C13 H13 . 120.4
C1A O1A C11A . 118.44(10)
O11A N1A O12A . 122.96(13)
O11A N1A C4A . 118.25(14)
O12A N1A C4A . 118.79(14)
O1A C1A C2A . 123.19(12)
O1A C1A C6A . 115.11(12)
C2A C1A C6A . 121.67(12)
C3A C2A C1A . 118.60(12)
C3A C2A H2A . 120.7
C1A C2A H2A . 120.7
C2A C3A C4A . 119.29(12)
C2A C3A H3A . 120.4
C4A C3A H3A . 120.4
C5A C4A C3A . 122.48(12)
C5A C4A N1A . 118.68(13)
C3A C4A N1A . 118.84(13)
C6A C5A C4A . 118.17(12)
C6A C5A H5A . 120.9
C4A C5A H5A . 120.9
C5A C6A C1A . 119.78(13)
C5A C6A H6A . 120.1
C1A C6A H6A . 120.1
C13A C11A C12A 2_766 121.87(13)
C13A C11A O1A 2_766 119.82(14)
C12A C11A O1A . 118.18(14)
C11A C12A C13A . 118.94(14)
C11A C12A H12A . 120.5
C13A C12A H12A . 120.5
C11A C13A C12A 2_766 119.19(13)
C11A C13A H13A 2_766 120.4
C12A C13A H13A . 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.3828(15)
O1 C11 . 1.4085(15)
N1 O12 . 1.2339(16)
N1 O11 . 1.2347(16)
N1 C4 . 1.4704(16)
C1 C6 . 1.3955(17)
C1 C2 . 1.3971(18)
C2 C3 . 1.3940(18)
C2 H2 . 0.9500
C3 C4 . 1.3895(18)
C3 H3 . 0.9500
C4 C5 . 1.3891(18)
C5 C6 . 1.3919(18)
C5 H5 . 0.9500
C6 H6 . 0.9500
C11 C13 2_575 1.3891(19)
C11 C12 . 1.3914(18)
C12 C13 . 1.3936(18)
C12 H12 . 0.9500
C13 C11 2_575 1.3891(19)
C13 H13 . 0.9500
O1A C1A . 1.3790(16)
O1A C11A . 1.4003(17)
N1A O11A . 1.229(2)
N1A O12A . 1.2306(19)
N1A C4A . 1.4665(17)
C1A C2A . 1.3945(18)
C1A C6A . 1.3950(19)
C2A C3A . 1.3894(18)
C2A H2A . 0.9500
C3A C4A . 1.391(2)
C3A H3A . 0.9500
C4A C5A . 1.390(2)
C5A C6A . 1.388(2)
C5A H5A . 0.9500
C6A H6A . 0.9500
C11A C13A 2_766 1.385(2)
C11A C12A . 1.387(2)
C12A C13A . 1.394(2)
C12A H12A . 0.9500
C13A C11A 2_766 1.385(2)
C13A H13A . 0.9500
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_4
_geom_torsion
C11 O1 C1 C6 . . 150.47(12)
C11 O1 C1 C2 . . -33.18(18)
O1 C1 C2 C3 . . -176.35(12)
C6 C1 C2 C3 . . -0.2(2)
C1 C2 C3 C4 . . 0.5(2)
C2 C3 C4 C5 . . -0.1(2)
C2 C3 C4 N1 . . 179.99(12)
O12 N1 C4 C5 . . -169.00(11)
O11 N1 C4 C5 . . 11.10(17)
O12 N1 C4 C3 . . 10.89(17)
O11 N1 C4 C3 . . -169.01(12)
C3 C4 C5 C6 . . -0.58(19)
N1 C4 C5 C6 . . 179.30(11)
C4 C5 C6 C1 . . 0.89(18)
O1 C1 C6 C5 . . 175.89(11)
C2 C1 C6 C5 . . -0.52(19)
C1 O1 C11 C13 . 2_575 -54.41(17)
C1 O1 C11 C12 . . 130.95(12)
C13 C11 C12 C13 2_575 . 0.0(2)
O1 C11 C12 C13 . . 174.59(11)
C11 C12 C13 C11 . 2_575 0.0(2)
C11A O1A C1A C2A . . -20.0(2)
C11A O1A C1A C6A . . 161.88(14)
O1A C1A C2A C3A . . -177.50(14)
C6A C1A C2A C3A . . 0.5(2)
C1A C2A C3A C4A . . -0.3(2)
C2A C3A C4A C5A . . -0.2(2)
C2A C3A C4A N1A . . 179.80(12)
O11A N1A C4A C5A . . 178.73(14)
O12A N1A C4A C5A . . -0.79(19)
O11A N1A C4A C3A . . -1.3(2)
O12A N1A C4A C3A . . 179.19(12)
C3A C4A C5A C6A . . 0.6(2)
N1A C4A C5A C6A . . -179.38(13)
C4A C5A C6A C1A . . -0.5(2)
O1A C1A C6A C5A . . 178.07(14)
C2A C1A C6A C5A . . -0.1(2)
C1A O1A C11A C13A . 2_766 -75.01(19)
C1A O1A C11A C12A . . 109.05(16)
C13A C11A C12A C13A 2_766 . -0.3(2)
O1A C11A C12A C13A . . 175.54(12)
C11A C12A C13A C11A . 2_766 0.3(2)
