##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     ' SHELXL97 (Sheldrick, 1997)'
_journal_date_recd_electronic     2002-08-14
_journal_date_accepted     2002-09-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2002
_journal_volume     58
_journal_issue     10
_journal_page_first     o1088
_journal_page_last     o1090
_journal_paper_category     EO
_publ_contact_author_name     'Dr Graham Smith'
_publ_contact_author_address
;
    Centre for Instrumental and Developmental Chemistry
    Queensland University of Technology
    GPO Box 2434, Brisbane 4001, Australia
;
_publ_contact_author_email     ' g.smith@qut.edu.au '
_publ_contact_author_fax     ' 61 7 3864 1804 '
_publ_contact_author_phone     ' 61 7 3864 2293 '
_publ_section_title
;
Ethylenediammonium 4-nitroanthranilate dihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    ' Graham Smith '
;
  Centre for Instrumental and Developmental Chemistry
  Queensland University of Technology
  GPO Box 2434, Brisbane 4001, Australia
;
    ' Urs D. Wermuth '
;
  Centre for Instrumental and Developmental Chemistry
  Queensland University of Technology
  GPO Box 2434, Brisbane 4001, Australia
;
    ' Jonathan M. White '
;
 School of Chemistry
University of Melbourne
Parkville, 3052, Australia
;
data_I
_chemical_name_systematic
;
 ?
;
_chemical_name_common
;
 Ethylenediammonium 4-nitroanthranilate dihydrate
;
_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     ' 493.6--495.4 '
_symmetry_cell_setting     'Triclinic '
_symmetry_space_group_name_H-M     'P -1 '
_symmetry_space_group_name_Hall     '-P 1 '
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.6473(5)
_cell_length_b     7.0748(5)
_cell_length_c     11.2317(8)
_cell_angle_alpha     76.686(2)
_cell_angle_beta     77.660(2)
_cell_angle_gamma     89.525(2)
_cell_volume     501.67(6)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     2947
_cell_measurement_theta_min     2.96
_cell_measurement_theta_max     28.33
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'Plate '
_exptl_crystal_colour     'Red '
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.524
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     none
_exptl_crystal_F_000     242
_exptl_absorpt_coefficient_mu     0.128
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'graphite '
_diffrn_measurement_device_type
;
Bruker SMART CCD area detector diffractometer
;
_diffrn_measurement_method     'φ and ω scans '
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4462
_diffrn_reflns_av_R_equivalents     0.0459
_diffrn_reflns_av_sigmaI/netI     0.0386
_diffrn_reflns_theta_min     1.91
_diffrn_reflns_theta_max     28.59
_diffrn_reflns_theta_full     28.59
_diffrn_measured_fraction_theta_max     0.971
_diffrn_measured_fraction_theta_full     0.971
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR
 and goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2475
_reflns_number_gt     2052
_reflns_threshold_expression     'I >2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0488
_refine_ls_R_factor_gt     0.0453
_refine_ls_wR_factor_gt     0.1332
_refine_ls_wR_factor_ref     0.1369
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_restrained_S_all     1.069
_refine_ls_number_reflns     2475
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0745P)²+0.0989P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.010
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max     0.264
_refine_diff_density_min     -0.228
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_extinction_expression     ?
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'
_computing_data_collection     'SMART (Bruker, 2000) '
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1999) '
_computing_structure_solution     'SHELXTL (Bruker, 1997)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'PLATON (Spek, 1999)'
_computing_publication_material     ?
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_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 0.0282(5) 0.0256(6) 0.0268(6) 0.0010(4) -0.0046(4) -0.0023(4)
    C2 0.0330(6) 0.0280(6) 0.0276(6) 0.0008(4) -0.0048(4) -0.0045(4)
    C3 0.0425(7) 0.0254(6) 0.0325(6) -0.0030(5) -0.0079(5) -0.0012(4)
    C4 0.0323(6) 0.0383(7) 0.0252(6) -0.0042(5) -0.0058(4) 0.0019(5)
    C5 0.0340(6) 0.0434(7) 0.0264(6) 0.0014(5) -0.0052(4) -0.0103(5)
    C6 0.0329(6) 0.0282(6) 0.0327(6) 0.0018(4) -0.0067(5) -0.0080(4)
    C7 0.0329(6) 0.0289(6) 0.0311(6) -0.0020(4) -0.0039(5) -0.0008(4)
    C8 0.0486(7) 0.0330(6) 0.0293(6) 0.0010(5) -0.0055(5) -0.0084(5)
    N1 0.0616(8) 0.0286(6) 0.0329(6) -0.0001(5) 0.0005(5) -0.0084(4)
    N2 0.0452(7) 0.0520(7) 0.0299(6) -0.0107(5) -0.0082(5) 0.0053(5)
    N3 0.0455(6) 0.0309(6) 0.0310(6) -0.0003(5) -0.0021(5) -0.0027(4)
    O1 0.0759(8) 0.0254(5) 0.0504(6) -0.0053(5) 0.0106(5) -0.0016(4)
    O2 0.0616(7) 0.0402(5) 0.0307(5) -0.0120(5) 0.0066(4) -0.0049(4)
    O3 0.1121(12) 0.0524(7) 0.0433(7) -0.0338(7) -0.0106(7) 0.0104(5)
    O4 0.0693(8) 0.0758(9) 0.0272(5) 0.0007(6) 0.0018(5) 0.0001(5)
    O5 0.0448(6) 0.0462(6) 0.0394(6) -0.0088(5) -0.0045(5) 0.0048(5)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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
    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_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_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    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) ?
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
