#------------------------------------------------------------------------------
#$Date: 2019-10-28 09:23:29 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219800 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/60/2206027.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_2206027
loop_
_publ_author_name
'Jones, Helen P.'
'Gillon, Amy L.'
'Davey, Roger J.'
_publ_section_title
;
 A co-crystal of ethylenediammonium bis(3,5-dinitrobenzoate) and
 3,5-dinitrobenzoic acid
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1823
_journal_page_last               o1825
_journal_paper_doi               10.1107/S1600536805015333
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac       'C2 H10 N2 2+, 2(C7 H3 N2 O6 -), 2(C7 H4 N2 O6)'
_chemical_formula_moiety      'C2 H10 N2 2+, 2(C7 H3 N2 O6 -), 2(C7 H4 N2 O6)'
_chemical_formula_structural     'C30 H24 N10 O24'
_chemical_formula_sum            'C30 H24 N10 O24'
_chemical_formula_weight         908.6
_chemical_name_systematic
;
ethylenediaminium--3,5-dinitrobenzoate--3,5-dinitrobenzoic acid (1/2/2),
C₂H₁₀N₂²⁺.2C₇H₃N₂O₆⁻.2C₇H₄N₂O₆
;
_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
_cell_angle_alpha                91.838(2)
_cell_angle_beta                 96.230(2)
_cell_angle_gamma                98.7100(10)
_cell_formula_units_Z            1
_cell_length_a                   7.0452(3)
_cell_length_b                   11.2345(4)
_cell_length_c                   11.7627(5)
_cell_measurement_reflns_used    5294
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      0.998
_cell_volume                     913.72(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 2000)'
_computing_data_reduction
'HKL Denzo (Otwinowski & Minor, 1997) and Scalepack'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ or ω scans?'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8852
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Blessing, 1995)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.213
_refine_ls_extinction_coef       0.016(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   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.072
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0776P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                2256
_reflns_number_total             3241
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng6162.cif
_cod_data_source_block           I
_cod_depositor_comments
;

2019-10-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C15 H12 N5 O12'
_cod_original_formula_weight         454.3
_cod_original_formula_moiety     '0.5C2 H10 N2 2+, C7 H3 N2 O6 -, C7 H4 N2 O6'
_cod_original_formula_iupac      '0.5C2 H10 N2 2+, C7 H3 N2 O6 -, C7 H4 N2 O6'
_cod_original_formula_units_Z            2
_cod_database_code               2206027
_cod_database_fobs_code          2206027
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.3739(2) 0.04198(13) 0.75723(14) 0.0508(4) Uani d . 1 O
O2 0.6632(3) -0.01493(13) 0.76044(15) 0.0553(5) Uani d . 1 O
O3 0.7755(3) -0.38263(14) 0.94862(14) 0.0596(5) Uani d . 1 O
O4 0.6306(3) -0.42815(15) 1.09778(14) 0.0648(5) Uani d . 1 O
O5 0.0621(3) -0.26099(18) 1.15926(16) 0.0718(6) Uani d . 1 O
O6 -0.0276(3) -0.12294(18) 1.05344(18) 0.0724(6) Uani d . 1 O
O7 0.5246(3) 0.24130(15) 0.69250(16) 0.0590(5) Uani d D 1 O
O8 0.2299(3) 0.26663(15) 0.62078(17) 0.0680(5) Uani d . 1 O
O9 0.1253(3) 0.66997(17) 0.50938(18) 0.0741(6) Uani d . 1 O
O10 0.3350(3) 0.82267(16) 0.5700(2) 0.0889(7) Uani d . 1 O
O11 0.9653(3) 0.76827(14) 0.73491(15) 0.0618(5) Uani d . 1 O
O12 1.0348(3) 0.58912(16) 0.75615(16) 0.0638(5) Uani d . 1 O
N1 0.6524(3) -0.37047(16) 1.01241(16) 0.0475(5) Uani d . 1 N
N2 0.0813(3) -0.19415(18) 1.07990(18) 0.0520(5) Uani d . 1 N
N3 0.2801(3) 0.71433(18) 0.55839(17) 0.0537(5) Uani d . 1 N
N4 0.9221(3) 0.65764(17) 0.72899(16) 0.0455(5) Uani d . 1 N
N5 0.9846(3) 0.05043(17) 0.65242(17) 0.0571(6) Uani d . 1 N
H5A 0.8995 0.0265 0.7009 0.069 Uiso calc R 1 H
H5B 0.9863 0.1285 0.6413 0.069 Uiso calc R 1 H
H5C 1.1016 0.0382 0.6816 0.069 Uiso calc R 1 H
C1 0.4465(3) -0.11491(17) 0.87777(17) 0.0371(5) Uani d . 1 C
C2 0.5689(3) -0.19825(17) 0.90467(17) 0.0394(5) Uani d . 1 C
H2 0.681 -0.1975 0.8694 0.047 Uiso calc R 1 H
C3 0.5229(3) -0.28228(18) 0.98423(17) 0.0403(5) Uani d . 1 C
C4 0.3618(3) -0.28528(19) 1.04054(18) 0.0433(6) Uani d . 1 C
H4 0.332 -0.3427 1.0937 0.052 Uiso calc R 1 H
C5 0.2463(3) -0.19926(18) 1.01452(17) 0.0400(5) Uani d . 1 C
C6 0.2833(3) -0.11494(18) 0.93258(18) 0.0395(5) Uani d . 1 C
H6 0.1998 -0.0598 0.9151 0.047 Uiso calc R 1 H
C7 0.5006(3) -0.02253(17) 0.79096(18) 0.0403(5) Uani d . 1 C
C8 0.4724(3) 0.43735(17) 0.65036(16) 0.0368(5) Uani d . 1 C
C9 0.3459(3) 0.51274(18) 0.60851(17) 0.0391(5) Uani d . 1 C
H9 0.2179 0.482 0.5824 0.047 Uiso calc R 1 H
C10 0.4134(3) 0.63433(18) 0.60626(17) 0.0404(5) Uani d . 1 C
C11 0.5990(3) 0.68435(18) 0.64562(17) 0.0400(5) Uani d . 1 C
H11 0.6405 0.7669 0.6452 0.048 Uiso calc R 1 H
C12 0.7218(3) 0.60689(18) 0.68589(17) 0.0375(5) Uani d . 1 C
C13 0.6631(3) 0.48361(18) 0.68852(17) 0.0382(5) Uani d . 1 C
H13 0.7496 0.4332 0.7152 0.046 Uiso calc R 1 H
C14 0.3964(4) 0.30531(19) 0.65396(18) 0.0432(6) Uani d . 1 C
C15 0.9287(3) -0.01948(18) 0.54167(18) 0.0421(5) Uani d . 1 C
H15A 0.8006 -0.007 0.5102 0.051 Uiso calc R 1 H
H15B 0.9249 -0.1048 0.5538 0.051 Uiso calc R 1 H
H7 0.469(5) 0.1743(18) 0.709(3) 0.123(14) Uiso d D 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 0.006 '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
C14 O7 H7 . . 109(3)
O4 N1 O3 . . 123.8(2)
O4 N1 C3 . . 118.1(2)
O3 N1 C3 . . 118.10(18)
O6 N2 O5 . . 123.3(2)
O6 N2 C5 . . 118.5(2)
O5 N2 C5 . . 118.1(2)
O9 N3 O10 . . 123.6(2)
O9 N3 C10 . . 118.95(19)
O10 N3 C10 . . 117.5(2)
O12 N4 O11 . . 124.0(2)
O12 N4 C12 . . 118.64(18)
O11 N4 C12 . . 117.41(19)
C15 N5 H5A . . 109.5
C15 N5 H5B . . 109.5
H5A N5 H5B . . 109.5
C15 N5 H5C . . 109.5
H5A N5 H5C . . 109.5
H5B N5 H5C . . 109.5
C6 C1 C2 . . 119.86(19)
C6 C1 C7 . . 121.5(2)
C2 C1 C7 . . 118.6(2)
C3 C2 C1 . . 119.4(2)
C3 C2 H2 . . 120.3
C1 C2 H2 . . 120.3
C4 C3 C2 . . 122.5(2)
C4 C3 N1 . . 118.23(19)
C2 C3 N1 . . 119.3(2)
C3 C4 C5 . . 116.8(2)
C3 C4 H4 . . 121.6
C5 C4 H4 . . 121.6
C4 C5 C6 . . 122.9(2)
C4 C5 N2 . . 118.01(19)
C6 C5 N2 . . 119.0(2)
C1 C6 C5 . . 118.5(2)
C1 C6 H6 . . 120.7
C5 C6 H6 . . 120.7
O2 C7 O1 . . 125.5(2)
O2 C7 C1 . . 117.6(2)
O1 C7 C1 . . 116.8(2)
C9 C8 C13 . . 120.38(19)
C9 C8 C14 . . 118.1(2)
C13 C8 C14 . . 121.48(19)
C10 C9 C8 . . 118.6(2)
C10 C9 H9 . . 120.7
C8 C9 H9 . . 120.7
C11 C10 C9 . . 123.0(2)
C11 C10 N3 . . 118.33(19)
C9 C10 N3 . . 118.7(2)
C10 C11 C12 . . 116.98(19)
C10 C11 H11 . . 121.5
C12 C11 H11 . . 121.5
C11 C12 C13 . . 122.6(2)
C11 C12 N4 . . 118.40(18)
C13 C12 N4 . . 119.0(2)
C8 C13 C12 . . 118.3(2)
C8 C13 H13 . . 120.8
C12 C13 H13 . . 120.8
O8 C14 O7 . . 125.3(2)
O8 C14 C8 . . 120.6(2)
O7 C14 C8 . . 114.1(2)
N5 C15 C15 . 2_756 110.4(2)
N5 C15 H15A . . 109.6
C15 C15 H15A 2_756 . 109.6
N5 C15 H15B . . 109.6
C15 C15 H15B 2_756 . 109.6
H15A C15 H15B . . 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C7 . 1.271(3)
O2 C7 . 1.229(3)
O3 N1 . 1.226(2)
O4 N1 . 1.224(2)
O5 N2 . 1.223(3)
O6 N2 . 1.215(3)
O7 C14 . 1.292(3)
O7 H7 . 0.833(10)
O8 C14 . 1.205(3)
O9 N3 . 1.204(3)
O10 N3 . 1.219(3)
O11 N4 . 1.232(2)
O12 N4 . 1.213(2)
N1 C3 . 1.468(3)
N2 C5 . 1.469(3)
N3 C10 . 1.477(3)
N4 C12 . 1.468(3)
N5 C15 . 1.483(3)
N5 H5A . 0.89
N5 H5B . 0.89
N5 H5C . 0.89
C1 C6 . 1.377(3)
C1 C2 . 1.388(3)
C1 C7 . 1.516(3)
C2 C3 . 1.379(3)
C2 H2 . 0.93
C3 C4 . 1.371(3)
C4 C5 . 1.376(3)
C4 H4 . 0.93
C5 C6 . 1.390(3)
C6 H6 . 0.93
C8 C9 . 1.384(3)
C8 C13 . 1.386(3)
C8 C14 . 1.502(3)
C9 C10 . 1.379(3)
C9 H9 . 0.93
C10 C11 . 1.367(3)
C11 C12 . 1.377(3)
C11 H11 . 0.93
C12 C13 . 1.386(3)
C13 H13 . 0.93
C15 C15 2_756 1.506(4)
C15 H15A . 0.97
C15 H15B . 0.97
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
O7 H7 O1 . 0.833(10) 1.677(11) 2.507(2) 173(4)
N5 H5A O2 . 0.89 1.88 2.732(3) 161
N5 H5B O8 1_655 0.89 2.17 2.820(3) 129
N5 H5C O1 1_655 0.89 2.02 2.899(3) 170
