#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/13/2201391.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_2201391
loop_
_publ_author_name
' Graham Smith '
' Urs D. Wermuth '
' Jonathan M. White '
_publ_section_title
;
 Ethylenediammonium 4-nitroanthranilate dihydrate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1088
_journal_page_last               o1090
_journal_paper_doi               10.1107/S160053680201601X
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety
;
  C2 H10 N2 2+ , 2C7 H5 N2 O4 1-, 2H2 O
;
_chemical_formula_sum            'C16 H24 N6 O10'
_chemical_formula_weight         460.42
_chemical_melting_point          494.5(9)
_chemical_name_common
;
 Ethylenediammonium 4-nitroanthranilate dihydrate
;
_chemical_name_systematic
;
 ?
;
_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                76.686(2)
_cell_angle_beta                 77.660(2)
_cell_angle_gamma                89.525(2)
_cell_formula_units_Z            1
_cell_length_a                   6.6473(5)
_cell_length_b                   7.0748(5)
_cell_length_c                   11.2317(8)
_cell_measurement_reflns_used    2947
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.96
_cell_volume                     501.67(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000) '
_computing_data_reduction        'SAINT (Bruker, 1999) '
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type
;
Bruker SMART CCD area detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans '
_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  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4462
_diffrn_reflns_theta_full        28.59
_diffrn_reflns_theta_max         28.59
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Red '
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    none
_exptl_crystal_description       'Plate '
_exptl_crystal_F_000             242
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0745P)²+0.0989P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                2052
_reflns_number_total             2475
_reflns_threshold_expression     'I >2σ(I)'
_cod_data_source_file            ci6153.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:

'_chemical_melting_point' value ' 493.6--495.4 ' was changed to
'494.5(9)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value ' 493.6--495.4 ' was changed to
'494.5(9)' - the average value was taken and precision was
estimated.

'_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_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               2201391
_cod_database_fobs_code          2201391
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.64571(17) -0.04597(16) 0.15627(10) 0.0277(3) Uani d . 1 . . C
C2 0.66670(18) 0.15338(17) 0.15449(11) 0.0301(3) Uani d . 1 . . C
C3 0.7519(2) 0.28286(17) 0.03922(12) 0.0344(3) Uani d . 1 . . C
H3 0.7677 0.4149 0.0351 0.041 Uiso calc R 1 . . H
C4 0.81153(19) 0.21337(19) -0.06693(11) 0.0336(3) Uani d . 1 . . C
C5 0.79504(19) 0.0192(2) -0.06782(11) 0.0345(3) Uani d . 1 . . C
H5 0.8380 -0.0239 -0.1410 0.041 Uiso calc R 1 . . H
C6 0.71171(18) -0.10772(17) 0.04521(11) 0.0312(3) Uani d . 1 . . C
H6 0.6990 -0.2394 0.0475 0.037 Uiso calc R 1 . . H
C7 0.54568(19) -0.19649(17) 0.27287(11) 0.0325(3) Uani d . 1 . . C
C8 0.0253(2) 0.94508(18) 0.56105(11) 0.0372(3) Uani d . 1 . . C
H8A 0.1297 1.0184 0.5823 0.045 Uiso calc R 1 . . H
H8B -0.0970 0.9292 0.6280 0.045 Uiso calc R 1 . . H
N1 0.6138(2) 0.22588(18) 0.25992(11) 0.0425(3) Uani d . 1 . . N
N2 0.90109(19) 0.35319(19) -0.18554(10) 0.0447(3) Uani d . 1 . . N
N3 0.1014(2) 0.75257(16) 0.54837(11) 0.0375(3) Uani d . 1 . . N
H3A 0.002(3) 0.682(3) 0.5334(17) 0.053(5) Uiso d . 1 . . H
H3B 0.133(3) 0.695(3) 0.619(2) 0.062(5) Uiso d . 1 . . H
H3C 0.219(3) 0.763(2) 0.4869(17) 0.047(4) Uiso d . 1 . . H
O1 0.5325(2) -0.36820(14) 0.26359(10) 0.0555(3) Uani d . 1 . . O
O2 0.47940(18) -0.14314(15) 0.37310(9) 0.0472(3) Uani d . 1 . . O
O3 0.9185(3) 0.52434(19) -0.18427(12) 0.0736(5) Uani d . 1 . . O
O4 0.9547(2) 0.2929(2) -0.28036(10) 0.0613(4) Uani d . 1 . . O
O5 0.27641(17) 0.39858(16) 0.46802(11) 0.0466(3) Uani d . 1 . . O
H5A 0.355(3) 0.470(3) 0.406(2) 0.058(5) Uiso d . 1 . . H
H1A 0.531(3) 0.151(3) 0.3245(19) 0.054(5) Uiso d . 1 . . H
H1B 0.597(3) 0.343(3) 0.2492(17) 0.049(5) Uiso d . 1 . . H
H5B 0.348(4) 0.341(4) 0.511(2) 0.076(7) Uiso 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 0.0000 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
C6 C1 C2 . . 119.33(10)
C6 C1 C7 . . 117.84(10)
C2 C1 C7 . . 122.78(11)
N1 C2 C3 . . 118.54(11)
N1 C2 C1 . . 123.30(11)
C3 C2 C1 . . 118.13(11)
C4 C3 C2 . . 119.73(11)
C4 C3 H3 . . 120.1
C2 C3 H3 . . 120.1
C3 C4 C5 . . 123.44(11)
C3 C4 N2 . . 118.12(12)
C5 C4 N2 . . 118.43(12)
C4 C5 C6 . . 116.82(11)
C4 C5 H5 . . 121.6
C6 C5 H5 . . 121.6
C5 C6 C1 . . 122.54(11)
C5 C6 H6 . . 118.7
C1 C6 H6 . . 118.7
O1 C7 O2 . . 123.55(11)
O1 C7 C1 . . 117.51(11)
O2 C7 C1 . . 118.94(11)
N3 C8 C8 . 2_576 109.84(13)
N3 C8 H8A . . 109.7
C8 C8 H8A 2_576 . 109.7
N3 C8 H8B . . 109.7
C8 C8 H8B 2_576 . 109.7
H8A C8 H8B . . 108.2
C2 N1 H1A . . 115.8(13)
C2 N1 H1B . . 117.0(12)
H1A N1 H1B . . 116.3(18)
O4 N2 O3 . . 122.99(12)
O4 N2 C4 . . 118.63(13)
O3 N2 C4 . . 118.38(12)
C8 N3 H3A . . 109.5(12)
C8 N3 H3B . . 107.6(13)
H3A N3 H3B . . 109.6(18)
C8 N3 H3C . . 111.5(11)
H3A N3 H3C . . 111.2(15)
H3B N3 H3C . . 107.3(18)
H5A O5 H5B . . 107(2)
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 C6 . 1.3975(16) ?
C1 C2 . 1.4135(16) ?
C1 C7 . 1.5128(15) ?
C2 N1 . 1.3740(16) ?
C2 C3 . 1.4089(17) ?
C3 C4 . 1.3730(18) ?
C3 H3 . 0.93 ?
C4 C5 . 1.3812(19) ?
C4 N2 . 1.4736(15) ?
C5 C6 . 1.3812(18) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 O1 . 1.2483(16) ?
C7 O2 . 1.2588(16) ?
C8 N3 . 1.4758(17) ?
C8 C8 2_576 1.517(2) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
N1 H1A . 0.88(2) ?
N1 H1B . 0.82(2) ?
N2 O4 . 1.2195(17) ?
N2 O3 . 1.2210(18) ?
N3 H3A . 0.90(2) ?
N3 H3B . 0.87(2) ?
N3 H3C . 0.915(18) ?
O5 H5A . 0.84(2) ?
O5 H5B . 0.79(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
_geom_hbond_publ_flag
N1 H1A O2 . 0.88(2) 2.04(2) 2.6935(17) 130.8(18) yes
N1 H1B O1 1_565 0.82(2) 2.12(2) 2.9258(17) 167.8(17) yes
N3 H3A O5 2_566 0.90(2) 1.95(2) 2.7960(18) 157.5(19) yes
N3 H3B O3 1_456 0.87(2) 2.41(2) 3.0564(18) 130.9(17) yes
N3 H3B N1 2_666 0.87(2) 2.52(2) 3.1847(18) 133.8(18) yes
N3 H3C O2 1_565 0.917(19) 1.937(19) 2.8250(17) 162.5(14) yes
O5 H5A O1 1_565 0.84(2) 1.91(2) 2.7429(16) 179(2) yes
O5 H5B O2 2_656 0.79(3) 2.18(3) 2.9647(16) 171(3) yes
C6 H6 O1 . 0.9301 2.4075 2.7454(16) 101.3 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
C6 C1 C2 N1 -177.28(11)
C7 C1 C2 N1 5.44(19)
C6 C1 C2 C3 0.76(18)
C7 C1 C2 C3 -176.52(11)
N1 C2 C3 C4 178.14(11)
C1 C2 C3 C4 0.01(19)
C2 C3 C4 C5 -0.8(2)
C2 C3 C4 N2 -179.65(11)
C3 C4 C5 C6 0.67(19)
N2 C4 C5 C6 179.56(11)
C4 C5 C6 C1 0.16(19)
C2 C1 C6 C5 -0.87(19)
C7 C1 C6 C5 176.55(11)
C6 C1 C7 O1 1.70(18)
C2 C1 C7 O1 179.02(12)
C6 C1 C7 O2 -177.87(11)
C2 C1 C7 O2 -0.55(19)
C3 C4 N2 O4 179.95(12)
C5 C4 N2 O4 1.00(19)
C3 C4 N2 O3 0.1(2)
C5 C4 N2 O3 -178.89(13)
