#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/63/1506365.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1506365
loop_
_publ_author_name
'Jones, H. P.'
'Davey, R. J.'
'Cox, B. G.'
_publ_section_title
;
 Crystallization of a salt of a weak organic acid and base: solubility
 relations, supersaturation control and polymorphic behavior.
;
_journal_issue                   11
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              5273
_journal_page_last               5278
_journal_paper_doi               10.1021/jp045000q
_journal_volume                  109
_journal_year                    2005
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C7 H3 N2 O6, 0.5(C2 H10 N2)'
_chemical_formula_structural     'C7 H3 N2 O6, 0.5(C2 H10 N2)'
_chemical_formula_sum            'C8 H8 N3 O6'
_chemical_formula_weight         242.17
_chemical_name_systematic
;
 ethylenediammonium 3,5-dinitrobenzoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2004-05-14T13:15:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                94.764(2)
_cell_angle_beta                 108.278(2)
_cell_angle_gamma                97.433(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7331(3)
_cell_length_b                   7.8045(3)
_cell_length_c                   10.4466(5)
_cell_measurement_reflns_used    3386
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      0.998
_cell_measurement_wavelength     0.71073
_cell_volume                     512.40(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.137034
_diffrn_orient_matrix_UB_12      0.227907E-1
_diffrn_orient_matrix_UB_13      0.771685E-1
_diffrn_orient_matrix_UB_21      -0.797234E-1
_diffrn_orient_matrix_UB_22      0.12786E-2
_diffrn_orient_matrix_UB_23      0.66223E-1
_diffrn_orient_matrix_UB_31      -0.29092E-2
_diffrn_orient_matrix_UB_32      -0.128331
_diffrn_orient_matrix_UB_33      0.8035E-3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3046
_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        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.83
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.57
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.09(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         1784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0674P)²+0.1318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1363
_reflns_number_gt                1463
_reflns_number_total             1784
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp045000qsi20041102_072345.cif
_cod_data_source_block           eac_01d
_cod_database_code               1506365
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
C12 C 0.5043(3) 1.4352(3) 0.5498(2) 0.0408(5) Uani 1 1 d
H121 H 0.369(4) 1.376(3) 0.538(2) 0.049 Uiso 1 1 d
H122 H 0.564(4) 1.493(3) 0.642(3) 0.049 Uiso 1 1 d
N11 N 0.6407(3) 1.3068(2) 0.53256(19) 0.0436(5) Uani 1 1 d
H111 H 0.636(4) 1.221(3) 0.591(3) 0.052 Uiso 1 1 d
H112 H 0.579(4) 1.246(3) 0.442(3) 0.052 Uiso 1 1 d
H113 H 0.768(4) 1.362(3) 0.539(2) 0.052 Uiso 1 1 d
C1 C 0.1938(3) 0.8401(3) -0.0073(2) 0.0357(5) Uani 1 1 d
H1 H 0.181(3) 0.745(3) 0.032(2) 0.043 Uiso 1 1 d
C2 C 0.2841(3) 1.0040(2) 0.06400(18) 0.0333(5) Uani 1 1 d
C3 C 0.2962(3) 1.1464(3) -0.0064(2) 0.0360(5) Uani 1 1 d
H3 H 0.353(4) 1.248(3) 0.040(2) 0.043 Uiso 1 1 d
C4 C 0.2184(3) 1.1210(3) -0.1465(2) 0.0371(5) Uani 1 1 d
C5 C 0.1264(3) 0.9593(3) -0.2211(2) 0.0395(5) Uani 1 1 d
H5 H 0.070(4) 0.947(3) -0.321(3) 0.047 Uiso 1 1 d
C6 C 0.1165(3) 0.8221(3) -0.1474(2) 0.0371(5) Uani 1 1 d
C21 C 0.3716(3) 1.0286(3) 0.2181(2) 0.0394(5) Uani 1 1 d
N41 N 0.2324(3) 1.2699(3) -0.22217(19) 0.0473(5) Uani 1 1 d
N61 N 0.0148(3) 0.6492(2) -0.22433(18) 0.0467(5) Uani 1 1 d
O21 O 0.3881(3) 0.8948(2) 0.27387(16) 0.0633(5) Uani 1 1 d
O22 O 0.4210(3) 1.1812(2) 0.27434(16) 0.0641(5) Uani 1 1 d
O41 O 0.1237(3) 1.2518(2) -0.34270(17) 0.0612(5) Uani 1 1 d
O42 O 0.3513(3) 1.4034(2) -0.16149(19) 0.0666(6) Uani 1 1 d
O61 O -0.0064(3) 0.6272(2) -0.34536(16) 0.0605(5) Uani 1 1 d
O62 O -0.0461(3) 0.5377(2) -0.16413(18) 0.0643(5) Uani 1 1 d
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N11 C12 C12 110.6(2) . 2_686
N11 C12 H121 108.8(15) . .
C12 C12 H121 110.8(15) 2_686 .
N11 C12 H122 107.5(14) . .
C12 C12 H122 110.6(14) 2_686 .
H121 C12 H122 108.4(19) . .
C12 N11 H111 109.3(15) . .
C12 N11 H112 107.5(15) . .
H111 N11 H112 106(2) . .
C12 N11 H113 109.6(16) . .
H111 N11 H113 117(2) . .
H112 N11 H113 107(2) . .
C6 C1 C2 118.93(19) . .
C6 C1 H1 117.7(14) . .
C2 C1 H1 123.4(14) . .
C1 C2 C3 119.70(17) . .
C1 C2 C21 120.39(18) . .
C3 C2 C21 119.91(17) . .
C4 C3 C2 119.06(18) . .
C4 C3 H3 122.8(15) . .
C2 C3 H3 118.2(15) . .
C3 C4 C5 122.87(19) . .
C3 C4 N41 119.65(18) . .
C5 C4 N41 117.48(18) . .
C6 C5 C4 116.18(18) . .
C6 C5 H5 123.1(13) . .
C4 C5 H5 120.7(13) . .
C5 C6 C1 123.27(18) . .
C5 C6 N61 117.24(18) . .
C1 C6 N61 119.49(19) . .
O21 C21 O22 127.08(19) . .
O21 C21 C2 116.82(18) . .
O22 C21 C2 116.10(19) . .
O42 N41 O41 124.2(2) . .
O42 N41 C4 117.97(18) . .
O41 N41 C4 117.87(19) . .
O62 N61 O61 123.89(18) . .
O62 N61 C6 118.10(18) . .
O61 N61 C6 118.01(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C12 N11 1.481(3) .
C12 C12 1.504(4) 2_686
C12 H121 0.94(3) .
C12 H122 0.96(2) .
N11 H111 0.95(3) .
N11 H112 0.96(3) .
N11 H113 0.89(3) .
C1 C6 1.379(3) .
C1 C2 1.384(3) .
C1 H1 0.88(2) .
C2 C3 1.390(3) .
C2 C21 1.516(3) .
C3 C4 1.378(3) .
C3 H3 0.87(2) .
C4 C5 1.384(3) .
C4 N41 1.468(3) .
C5 C6 1.377(3) .
C5 H5 0.98(3) .
C6 N61 1.473(3) .
C21 O21 1.238(3) .
C21 O22 1.239(3) .
N41 O42 1.219(2) .
N41 O41 1.227(2) .
N61 O62 1.217(2) .
N61 O61 1.222(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H111 O21 0.95(3) 1.77(3) 2.701(2) 165(2) 2_676
N11 H112 O22 0.96(3) 1.73(3) 2.666(2) 164(2) .
N11 H113 O61 0.89(3) 2.38(3) 3.092(3) 137(2) 1_666
