#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/39/2223930.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_2223930
loop_
_publ_author_name
'Zou, Ping'
'Zhang, Shuang'
'Liu, Ying'
'Qiao, Jun'
'Gao, Jin-Sheng'
_publ_section_title
;
 4,4'-(o-Phenylenedioxydimethylene)dipyridinium dinitrate
;
_journal_coeditor_code           NG2647
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2672
_journal_paper_doi               10.1107/S1600536809040215
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H18 N2 O2 2+, 2N O3 -'
_chemical_formula_moiety         'C18 H18 N2 O2 2+, 2(N O3 -)'
_chemical_formula_sum            'C18 H18 N4 O8'
_chemical_formula_weight         418.36
_chemical_name_systematic
;
4,4'-(o-Phenylenedioxydimethylene)dipyridinium dinitrate
;
_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                 110.75(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.364(6)
_cell_length_b                   19.7593(11)
_cell_length_c                   9.996(8)
_cell_measurement_reflns_used    5255
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      24.47
_cell_measurement_theta_min      3.00
_cell_volume                     1914.3(19)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_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  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9339
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_correction_T_min  0.9549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2195
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0552
_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)+(0.0652P)²+0.3119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                1203
_reflns_number_total             2195
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2647.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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        1914.2(19)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2223930
_cod_database_fobs_code          2223930
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 0.8168(3) 0.12902(14) 0.7346(3) 0.0648(7) Uani d . 1 . .
H H1 0.7836 0.1178 0.6380 0.078 Uiso calc R 1 . .
C C2 0.8406(2) 0.19528(14) 0.7751(2) 0.0601(7) Uani d . 1 . .
H H2 0.8229 0.2291 0.7063 0.072 Uiso calc R 1 . .
C C3 0.8913(2) 0.21178(12) 0.9188(2) 0.0493(6) Uani d . 1 . .
C C4 0.9127(3) 0.16022(12) 1.0166(3) 0.0600(7) Uani d . 1 . .
H H4 0.9450 0.1699 1.1140 0.072 Uiso calc R 1 . .
C C5 0.8867(3) 0.09496(13) 0.9712(3) 0.0668(7) Uani d . 1 . .
H H5 0.9012 0.0602 1.0377 0.080 Uiso calc R 1 . .
C C6 0.9194(3) 0.28409(12) 0.9634(2) 0.0553(6) Uani d . 1 . .
H H6A 0.9925 0.3017 0.9339 0.066 Uiso calc R 1 . .
H H6B 0.8372 0.3111 0.9188 0.066 Uiso calc R 1 . .
C C7 0.9788(2) 0.34991(10) 1.1756(2) 0.0460(5) Uani d . 1 . .
C C8 0.9581(2) 0.41020(12) 1.1024(3) 0.0546(6) Uani d . 1 . .
H H8 0.9299 0.4104 1.0031 0.066 Uiso calc R 1 . .
C C9 0.9797(3) 0.47065(11) 1.1773(3) 0.0580(6) Uani d . 1 . .
H H9 0.9663 0.5115 1.1281 0.070 Uiso calc R 1 . .
N N1 0.8408(2) 0.08066(13) 0.8325(2) 0.0632(6) Uani d . 1 . .
H H10 0.830(3) 0.0347(17) 0.815(3) 0.095(10) Uiso d . 1 . .
N N2 0.7766(2) -0.08567(12) 0.8502(2) 0.0687(6) Uani d . 1 . .
O O1 0.95913(17) 0.28718(7) 1.11369(15) 0.0572(5) Uani d . 1 . .
O O2 0.8126(2) -0.05377(9) 0.96265(19) 0.0749(6) Uani d U 1 . .
O O3 0.7935(2) -0.05844(11) 0.7449(2) 0.0908(7) Uani d U 1 . .
O O4 0.7253(3) -0.14159(13) 0.8438(3) 0.1233(10) Uani d U 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 0.0624(16) 0.0818(19) 0.0516(15) -0.0097(14) 0.0218(13) -0.0211(14)
C2 0.0659(16) 0.0697(16) 0.0447(13) -0.0076(13) 0.0198(12) -0.0086(12)
C3 0.0474(12) 0.0563(14) 0.0430(12) 0.0003(11) 0.0144(10) -0.0063(10)
C4 0.0729(16) 0.0537(15) 0.0459(13) 0.0010(12) 0.0118(12) -0.0072(11)
C5 0.0736(18) 0.0551(15) 0.0630(16) 0.0005(13) 0.0133(13) -0.0039(13)
C6 0.0699(15) 0.0541(14) 0.0402(12) 0.0008(12) 0.0175(11) -0.0006(10)
C7 0.0501(12) 0.0382(11) 0.0470(11) 0.0006(10) 0.0139(10) -0.0016(10)
C8 0.0631(15) 0.0488(13) 0.0492(13) -0.0002(11) 0.0164(11) 0.0049(11)
C9 0.0645(15) 0.0406(12) 0.0691(15) 0.0020(12) 0.0237(13) 0.0076(11)
N1 0.0598(13) 0.0607(15) 0.0666(15) -0.0034(11) 0.0191(11) -0.0199(12)
N2 0.0808(16) 0.0634(15) 0.0523(14) 0.0062(12) 0.0120(12) -0.0048(12)
O1 0.0859(11) 0.0411(9) 0.0372(8) -0.0022(8) 0.0125(7) -0.0021(6)
O2 0.1068(15) 0.0618(11) 0.0505(11) -0.0016(10) 0.0208(10) -0.0025(9)
O3 0.1169(16) 0.1030(16) 0.0543(12) 0.0114(13) 0.0325(11) -0.0007(11)
O4 0.160(2) 0.0758(15) 0.1154(19) -0.0354(15) 0.0251(16) -0.0257(13)
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
N1 C1 C2 . . 120.3(2) ?
N1 C1 H1 . . 119.8 ?
C2 C1 H1 . . 119.8 ?
C1 C2 C3 . . 119.7(2) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C4 C3 C2 . . 118.1(2) ?
C4 C3 C6 . . 122.1(2) ?
C2 C3 C6 . . 119.8(2) ?
C5 C4 C3 . . 120.1(2) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
N1 C5 C4 . . 120.4(3) ?
N1 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
O1 C6 C3 . . 108.15(19) ?
O1 C6 H6A . . 110.1 ?
C3 C6 H6A . . 110.1 ?
O1 C6 H6B . . 110.1 ?
C3 C6 H6B . . 110.1 ?
H6A C6 H6B . . 108.4 ?
O1 C7 C8 . . 125.0(2) ?
O1 C7 C7 . 2_757 115.02(11) ?
C8 C7 C7 . 2_757 119.93(14) ?
C7 C8 C9 . . 119.6(2) ?
C7 C8 H8 . . 120.2 ?
C9 C8 H8 . . 120.2 ?
C9 C9 C8 2_757 . 120.45(14) ?
C9 C9 H9 2_757 . 119.8 ?
C8 C9 H9 . . 119.8 ?
C1 N1 C5 . . 121.4(2) ?
C1 N1 H10 . . 126(2) ?
C5 N1 H10 . . 112(2) ?
O4 N2 O2 . . 120.0(3) ?
O4 N2 O3 . . 122.4(3) ?
O2 N2 O3 . . 117.6(2) ?
C7 O1 C6 . . 117.47(17) ?
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 N1 . 1.326(4) ?
C1 C2 . 1.367(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.383(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.375(3) ?
C3 C6 . 1.494(3) ?
C4 C5 . 1.362(3) ?
C4 H4 . 0.9300 ?
C5 N1 . 1.327(3) ?
C5 H5 . 0.9300 ?
C6 O1 . 1.411(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 O1 . 1.368(2) ?
C7 C8 . 1.375(3) ?
C7 C7 2_757 1.394(4) ?
C8 C9 . 1.386(3) ?
C8 H8 . 0.9300 ?
C9 C9 2_757 1.362(5) ?
C9 H9 . 0.9300 ?
N1 H10 . 0.92(3) ?
N2 O4 . 1.218(3) ?
N2 O2 . 1.226(3) ?
N2 O3 . 1.249(3) ?
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
N1 H10 O2 . 0.92(3) 2.34(3) 3.017(3) 130(2)
N1 H10 O3 . 0.92(3) 1.96(3) 2.873(3) 170(3)
