#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/36/2103612.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_2103612
loop_
_publ_author_name
'Burchell, Colin J.'
'Glidewell, Christopher'
'Lough, Alan J.'
'Ferguson, George'
_publ_section_title
;
 Salts of 3,5-dinitrobenzoic acid with organic diamines:
 hydrogen-bonded supramolecular structures in one, two and three
 dimensions
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              201
_journal_page_last               212
_journal_paper_doi               10.1107/S010876810001853X
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C12 H13 N2, C14 H7 N4 O12'
_chemical_formula_sum            'C26 H20 N6 O12'
_chemical_formula_weight         608.48
_chemical_name_systematic
;
3,5-Dinitrobenzoic acid--1,2-bis(4'-pyridyl)ethane (2/1)
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 110.960(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1344(6)
_cell_length_b                   4.9420(2)
_cell_length_c                   27.5984(14)
_cell_measurement_reflns_used    13358
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.09
_cell_volume                     1290.78(11)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa-CCD server software (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'NRCVAX-96, ORTEP (Johnson, 1976), PLATON (Spek, 2000)'
_computing_publication_material
'NRCVAX-96, SHELXL-97  and WordPerfect macro PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'NRCVAX-96 and SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_measured_fraction_theta_full .955
_diffrn_measured_fraction_theta_max .955
_diffrn_measurement_device_type  Kappa-CCD
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .043
_diffrn_reflns_av_sigmaI/netI    .0554
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            13358
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.09
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    .127
_exptl_absorpt_correction_T_max  .9751
_exptl_absorpt_correction_T_min  .9605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          .32
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .20
_refine_diff_density_max         .239
_refine_diff_density_min         -.278
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          .0586
_refine_ls_R_factor_gt           .0435
_refine_ls_shift/su_max          .000
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0414P)²+0.4399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1115
_reflns_number_gt                2287
_reflns_number_total             2838
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            na0113.cif
_cod_data_source_block           6
_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_sg_symbol_H-M      'P 21/c'
_cod_database_code               2103612
_cod_database_fobs_code          2103612
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_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_type_symbol
O1 1.01701(11) 1.4685(2) .63186(4) .0312(3) Uani d . 1 O
O2 1.13472(13) 1.4960(2) .57700(5) .0385(3) Uani d . 1 O
O3 1.49811(13) 2.1870(3) .60855(5) .0407(3) Uani d . 1 O
O4 1.54102(13) 2.4678(3) .67249(5) .0414(3) Uani d . 1 O
O5 1.26655(14) 2.4347(2) .78189(5) .0394(3) Uani d . 1 O
O6 1.11876(14) 2.1072(3) .77488(5) .0449(3) Uani d . 1 O
N3 1.47954(13) 2.2714(3) .64726(5) .0301(3) Uani d . 1 N
N5 1.20649(14) 2.2254(3) .76167(5) .0306(3) Uani d . 1 N
C11 1.19287(15) 1.8005(3) .64793(6) .0237(3) Uani d . 1 C
C12 1.29817(15) 1.9215(3) .63416(6) .0249(3) Uani d . 1 C
C13 1.37361(15) 2.1346(3) .66373(6) .0249(3) Uani d . 1 C
C14 1.34857(15) 2.2342(3) .70634(6) .0260(3) Uani d . 1 C
C15 1.24212(15) 2.1109(3) .71870(6) .0244(3) Uani d . 1 C
C16 1.16395(15) 1.8958(3) .69066(6) .0242(3) Uani d . 1 C
C17 1.10939(15) 1.5691(3) .61511(6) .0257(3) Uani d . 1 C
N1 .86651(13) 1.0833(3) .58171(5) .0259(3) Uani d . 1 N
C2 .79013(16) .9620(3) .60625(6) .0274(3) Uani d . 1 C
C3 .69732(16) .7560(3) .58328(6) .0270(3) Uani d . 1 C
C4 .68152(14) .6701(3) .53351(6) .0237(3) Uani d . 1 C
C5 .76474(15) .7954(3) .50919(6) .0277(3) Uani d . 1 C
C6 .85513(16) 1.0022(3) .53415(6) .0290(4) Uani d . 1 C
C7 .57701(15) .4516(3) .50692(6) .0268(3) Uani d . 1 C
H1 .9733 1.3433 .6120 .047 Uiso calc PR .50 H
H12 1.3180 1.8590 .6049 .030 Uiso calc R 1 H
H14 1.4018 2.3804 .7262 .031 Uiso calc R 1 H
H116 1.0920 1.8147 .7003 .029 Uiso calc R 1 H
H1A .9242 1.2164 .5969 .031 Uiso calc PR .50 H
H2 .8002 1.0193 .6402 .033 Uiso calc R 1 H
H3 .6442 .6726 .6014 .032 Uiso calc R 1 H
H5 .7592 .7387 .4756 .033 Uiso calc R 1 H
H6 .9104 1.0887 .5172 .035 Uiso calc R 1 H
H7A .5936 .2919 .5300 .032 Uiso calc R 1 H
H7B .5920 .3956 .4748 .032 Uiso calc R 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C17 O1 H1 . . 109.5 no
O3 N3 O4 . . 124.08(13) no
O3 N3 C13 . . 118.08(14) no
O4 N3 C13 . . 117.81(13) no
O6 N5 O5 . . 124.16(13) no
O6 N5 C15 . . 118.09(14) no
O5 N5 C15 . . 117.75(13) no
C12 C11 C16 . . 120.01(14) no
C12 C11 C17 . . 118.72(13) no
C16 C11 C17 . . 121.27(13) no
C13 C12 C11 . . 118.86(14) no
C13 C12 H12 . . 120.6 no
C11 C12 H12 . . 120.6 no
C14 C13 C12 . . 122.90(14) no
C14 C13 N3 . . 118.46(14) no
C12 C13 N3 . . 118.54(13) no
C13 C14 C15 . . 116.76(15) no
C13 C14 H14 . . 121.6 no
C15 C14 H14 . . 121.6 no
C14 C15 C16 . . 122.74(14) no
C14 C15 N5 . . 117.85(14) no
C16 C15 N5 . . 119.31(13) no
C15 C16 C11 . . 118.72(13) no
C15 C16 H116 . . 120.6 no
C11 C16 H116 . . 120.6 no
O2 C17 O1 . . 126.87(15) no
O2 C17 C11 . . 119.54(14) no
O1 C17 C11 . . 113.59(13) no
C6 N1 C2 . . 119.99(14) no
C6 N1 H1A . . 120.0 no
C2 N1 H1A . . 120.0 no
N1 C2 C3 . . 121.44(14) no
N1 C2 H2 . . 119.3 no
C3 C2 H2 . . 119.3 no
C2 C3 C4 . . 119.89(14) no
C2 C3 H3 . . 120.1 no
C4 C3 H3 . . 120.1 no
C3 C4 C5 . . 117.59(14) no
C3 C4 C7 . . 120.80(13) no
C5 C4 C7 . . 121.61(14) no
C6 C5 C4 . . 119.70(14) no
C6 C5 H5 . . 120.2 no
C4 C5 H5 . . 120.2 no
N1 C6 C5 . . 121.36(14) no
N1 C6 H6 . . 119.3 no
C5 C6 H6 . . 119.3 no
C4 C7 C7 . 3_666 111.76(16) no
C4 C7 H7A . . 109.3 no
C7 C7 H7A 3_666 . 109.3 no
C4 C7 H7B . . 109.3 no
C7 C7 H7B 3_666 . 109.3 no
H7A C7 H7B . . 107.9 no
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
O1 C17 . 1.2834(18) no
O1 H1 . .8400 no
O2 C17 . 1.2230(18) no
O3 N3 . 1.2223(18) no
O4 N3 . 1.2267(18) no
O5 N5 . 1.2286(18) no
O6 N5 . 1.2234(17) no
N3 C13 . 1.4714(19) no
N5 C15 . 1.4707(19) no
C11 C12 . 1.390(2) no
C11 C16 . 1.395(2) no
C11 C17 . 1.515(2) no
C12 C13 . 1.383(2) no
C12 H12 . .9500 no
C13 C14 . 1.380(2) no
C14 C15 . 1.384(2) no
C14 H14 . .9500 no
C15 C16 . 1.385(2) no
C16 H116 . .9500 no
N1 C6 . 1.337(2) no
N1 C2 . 1.3388(19) no
N1 H1A . .8800 no
C2 C3 . 1.377(2) no
C2 H2 . .9500 no
C3 C4 . 1.391(2) no
C3 H3 . .9500 no
C4 C5 . 1.397(2) no
C4 C7 . 1.507(2) no
C5 C6 . 1.381(2) no
C5 H5 . .9500 no
C6 H6 . .9500 no
C7 C7 3_666 1.544(3) no
C7 H7A . .9900 no
C7 H7B . .9900 no
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
_geom_hbond_publ_flag
O1 H1 N1 . .84 1.70 2.521(2) 167 yes
N1 H1A O1 . .88 1.65 2.521(2) 170 yes
C5 H5 O2 3_776 .95 2.39 3.241(2) 148 yes
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_4
_geom_torsion
_geom_torsion_publ_flag
C16 C11 C12 C13 . .6(2) no
C17 C11 C12 C13 . 179.35(13) no
C11 C12 C13 C14 . -.4(2) no
C11 C12 C13 N3 . -176.71(13) no
O3 N3 C13 C14 . -177.84(14) no
O4 N3 C13 C14 . .2(2) no
O3 N3 C13 C12 . -1.3(2) no
O4 N3 C13 C12 . 176.73(14) no
C12 C13 C14 C15 . -.2(2) no
N3 C13 C14 C15 . 176.10(13) no
C13 C14 C15 C16 . .7(2) no
C13 C14 C15 N5 . -175.77(13) no
O6 N5 C15 C14 . -175.48(14) no
O5 N5 C15 C14 . 4.8(2) no
O6 N5 C15 C16 . 7.9(2) no
O5 N5 C15 C16 . -171.77(14) no
C14 C15 C16 C11 . -.5(2) no
N5 C15 C16 C11 . 175.91(13) no
C12 C11 C16 C15 . -.2(2) no
C17 C11 C16 C15 . -178.91(13) no
C12 C11 C17 O2 . -1.0(2) no
C16 C11 C17 O2 . 177.81(14) no
C12 C11 C17 O1 . 178.61(13) no
C16 C11 C17 O1 . -2.6(2) no
C6 N1 C2 C3 . -1.0(2) no
N1 C2 C3 C4 . .0(2) no
C2 C3 C4 C5 . 1.5(2) no
C2 C3 C4 C7 . -177.91(14) no
C3 C4 C5 C6 . -1.9(2) no
C7 C4 C5 C6 . 177.42(14) no
C2 N1 C6 C5 . .5(2) no
C4 C5 C6 N1 . 1.0(2) no
C3 C4 C7 C7 3_666 68.6(2) no
C5 C4 C7 C7 3_666 -110.74(19) no
