#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006226.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_2006226
loop_
_publ_author_name
'Kolev, T.'
'Preut, H.'
'Bleckmann, P.'
'Radomirska, V.'
_publ_contact_author
;       Dr. Hans Preut
        Fachbereich Chemie
        Universit\"at Dortmund
        Otto-Hahn-Str. 6
        44221 Dortmund
        Germany
;
_publ_section_title
;
 Guanidinium Hydrogen Squarate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              805
_journal_page_last               807
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac          'C H6 N3 + , C4 H O4 -'
_chemical_formula_sum            'C5 H7 N3 O4'
_chemical_formula_weight         173.14
_chemical_melting_point          580
_chemical_name_common            'guanidinium hydrogen squarate'
_chemical_name_systematic
;
 ?
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 102.97(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.960(4)
_cell_length_b                   20.536(11)
_cell_length_c                   8.146(4)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      14.4
_cell_measurement_theta_min      7.2
_cell_volume                     1460.6(13)
_computing_cell_refinement       'Siemens R3m/V software'
_computing_data_collection       'Siemens R3m/V software'
_computing_data_reduction        'Siemens R3m/V software'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  'SHELXL93, PARST95 (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measurement_device       'Siemens R3m/V'
_diffrn_measurement_method       \w--2\q
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3302
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        '< 5'
_diffrn_standards_interval_count 300
_diffrn_standards_interval_time  150
_diffrn_standards_number         6
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             720
_exptl_crystal_size_max          1.18
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.239
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   0.988
_refine_ls_goodness_of_fit_obs   1.171
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         2588
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.191
_refine_ls_restrained_S_obs      1.164
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_obs          0.0562
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.1026P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1983
_refine_ls_wR_factor_obs         0.1528
_reflns_number_observed          1681
_reflns_number_total             2588
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    jz1154.cif
_[local]_cod_data_source_block   nic412
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        1460.6(12)
_cod_database_code               2006226
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_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
O1 0.0414(13) 0.0296(11) 0.0363(11) -0.0006(10) -0.0014(10) -0.0061(9)
O2 0.0344(12) 0.0317(12) 0.0452(12) 0.0058(10) -0.0038(10) -0.0062(9)
O3 0.0455(14) 0.0346(12) 0.0374(12) -0.0007(10) -0.0007(11) -0.0087(9)
O4 0.0394(13) 0.0374(12) 0.0440(13) 0.0134(11) 0.0003(11) -0.0009(10)
O6 0.0481(15) 0.0305(12) 0.0615(15) 0.0098(11) 0.0220(12) 0.0010(10)
O7 0.0414(14) 0.0284(11) 0.0614(14) 0.0009(10) 0.0244(12) 0.0013(10)
O8 0.0367(13) 0.0329(12) 0.0654(15) 0.0026(10) 0.0210(12) -0.0090(10)
O9 0.057(2) 0.0370(13) 0.078(2) -0.0135(12) 0.0346(14) -0.0061(12)
C1 0.034(2) 0.0254(14) 0.0270(14) -0.0032(13) 0.0057(13) 0.0013(12)
C2 0.031(2) 0.027(2) 0.0306(14) -0.0011(13) 0.0094(13) 0.0007(12)
C3 0.030(2) 0.0273(15) 0.0294(14) -0.0016(13) 0.0092(13) -0.0014(12)
C4 0.031(2) 0.031(2) 0.0279(14) 0.0028(13) 0.0064(13) 0.0006(12)
C5 0.033(2) 0.037(2) 0.0300(15) -0.0010(14) 0.0057(14) 0.0026(13)
N1 0.034(2) 0.055(2) 0.042(2) 0.001(2) -0.0032(14) -0.0016(14)
N2 0.041(2) 0.037(2) 0.041(2) 0.0037(14) 0.0015(13) -0.0052(13)
N3 0.040(2) 0.039(2) 0.048(2) 0.0055(14) -0.0028(14) -0.0086(13)
C6 0.036(2) 0.031(2) 0.037(2) 0.0044(14) 0.0083(14) -0.0003(13)
C7 0.028(2) 0.0272(15) 0.034(2) -0.0008(13) 0.0072(13) -0.0001(12)
C8 0.028(2) 0.0264(15) 0.035(2) 0.0004(13) 0.0051(13) -0.0039(12)
C9 0.038(2) 0.029(2) 0.039(2) -0.0037(14) 0.0099(15) -0.0033(13)
C10 0.034(2) 0.037(2) 0.031(2) -0.0024(14) 0.0059(14) 0.0016(13)
N4 0.042(2) 0.053(2) 0.056(2) -0.001(2) 0.0258(15) -0.007(2)
N5 0.050(2) 0.034(2) 0.054(2) -0.0072(14) 0.0198(15) -0.0109(13)
N6 0.048(2) 0.0318(15) 0.061(2) -0.0043(14) 0.023(2) -0.0079(13)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.3721(3) 0.57106(10) 0.1821(3) 0.0374(6) Uani d . 1 O
O2 0.4363(2) 0.42710(10) 0.0942(3) 0.0391(6) Uani d D 1 O
H2 0.426(4) 0.3833(15) 0.028(4) 0.059 Uiso d D 1 H
O3 0.1183(3) 0.42354(10) -0.2034(3) 0.0408(6) Uani d . 1 O
O4 0.0585(3) 0.57444(10) -0.1219(3) 0.0417(6) Uani d . 1 O
O6 0.2905(3) 0.83976(10) 0.1866(3) 0.0452(6) Uani d . 1 O
O7 0.2847(3) 0.68473(10) 0.1827(3) 0.0417(6) Uani d D 1 O
H7 0.325(4) 0.6367(15) 0.177(5) 0.063 Uiso d D 1 H
O8 0.5975(3) 0.68430(10) 0.0285(3) 0.0435(6) Uani d . 1 O
O9 0.6000(3) 0.83815(11) 0.0298(3) 0.0541(7) Uani d . 1 O
C1 0.2996(3) 0.53234(13) 0.0711(3) 0.0291(7) Uani d . 1 C
C2 0.3255(3) 0.46721(13) 0.0301(3) 0.0292(7) Uani d . 1 C
C3 0.1866(3) 0.46459(13) -0.1027(3) 0.0287(7) Uani d . 1 C
C4 0.1585(3) 0.53415(14) -0.0638(3) 0.0300(7) Uani d . 1 C
C5 0.2414(3) 0.50504(14) 0.4935(3) 0.0334(7) Uani d . 1 C
N1 0.3702(3) 0.50831(15) 0.6127(4) 0.0453(7) Uani d D 1 N
H1A 0.384(5) 0.5438(14) 0.671(5) 0.068 Uiso d D 1 H
H1B 0.425(4) 0.4717(14) 0.628(5) 0.068 Uiso d D 1 H
N2 0.2104(3) 0.45196(14) 0.3993(3) 0.0411(7) Uani d D 1 N
H2A 0.124(3) 0.4487(19) 0.319(4) 0.062 Uiso d D 1 H
H2B 0.275(4) 0.4204(15) 0.423(5) 0.062 Uiso d D 1 H
N3 0.1454(3) 0.55463(14) 0.4721(4) 0.0444(7) Uani d D 1 N
H3A 0.064(3) 0.5551(19) 0.390(4) 0.067 Uiso d D 1 H
H3B 0.178(4) 0.5883(14) 0.531(4) 0.067 Uiso d D 1 H
C6 0.3736(4) 0.79811(14) 0.1432(4) 0.0344(7) Uani d . 1 C
C7 0.3759(3) 0.72780(13) 0.1393(4) 0.0298(7) Uani d . 1 C
C8 0.5108(3) 0.72652(13) 0.0732(4) 0.0299(7) Uani d . 1 C
C9 0.5144(4) 0.79789(14) 0.0738(4) 0.0351(7) Uani d . 1 C
C10 0.0632(4) 0.24301(14) 0.6229(4) 0.0339(7) Uani d . 1 C
N4 -0.0590(4) 0.2398(2) 0.6875(4) 0.0480(8) Uani d D 1 N
H4A -0.105(4) 0.2019(14) 0.702(5) 0.072 Uiso d D 1 H
H4B -0.099(4) 0.2744(15) 0.726(5) 0.072 Uiso d D 1 H
N5 0.1399(4) 0.29836(13) 0.6236(4) 0.0447(7) Uani d D 1 N
H5A 0.123(5) 0.3346(14) 0.681(4) 0.067 Uiso d D 1 H
H5B 0.216(4) 0.2964(19) 0.574(5) 0.067 Uiso d D 1 H
N6 0.1080(4) 0.19036(13) 0.5533(4) 0.0451(8) Uani d D 1 N
H6A 0.054(4) 0.1543(14) 0.547(5) 0.068 Uiso d D 1 H
H6B 0.193(4) 0.1864(18) 0.515(5) 0.068 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 0.0000 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
_geom_angle_publ_flag
C1 O1 H7 118.5(16) ?
C2 O2 H2 111(2) ?
C7 O7 H7 112(2) ?
O1 C1 C2 132.7(3) y
O1 C1 C4 136.9(3) y
C2 C1 C4 90.4(2) y
O2 C2 C1 130.9(3) y
O2 C2 C3 136.1(3) y
C1 C2 C3 93.0(2) y
O3 C3 C2 136.9(3) y
O3 C3 C4 135.2(3) y
C2 C3 C4 87.9(2) y
O4 C4 C1 136.8(3) y
O4 C4 C3 134.5(3) y
C1 C4 C3 88.7(2) y
N3 C5 N2 120.8(3) ?
N3 C5 N1 119.3(3) ?
N2 C5 N1 119.8(3) ?
C5 N1 H1A 116.(3) ?
C5 N1 H1B 115.(3) ?
H1A N1 H1B 129.(4) ?
C5 N2 H2A 121.(3) ?
C5 N2 H2B 117.(3) ?
H2A N2 H2B 122.(4) ?
C5 N3 H3A 121.(3) ?
C5 N3 H3B 115.(3) ?
H3A N3 H3B 123.(4) ?
O6 C6 C7 135.3(3) y
O6 C6 C9 136.4(3) y
C7 C6 C9 88.3(2) y
O7 C7 C8 136.3(3) y
O7 C7 C6 131.2(3) y
C8 C7 C6 92.5(2) y
O8 C8 C7 138.1(3) y
O8 C8 C9 131.9(3) y
C7 C8 C9 90.0(2) y
O9 C9 C8 133.1(3) y
O9 C9 C6 137.8(3) y
C8 C9 C6 89.1(2) y
N4 C10 N6 119.3(3) ?
N4 C10 N5 121.1(3) ?
N6 C10 N5 119.6(3) ?
C10 N4 H4A 123.(3) ?
C10 N4 H4B 123.(3) ?
H4A N4 H4B 115.(4) ?
C10 N5 H5A 124.(3) ?
C10 N5 H5B 115.(3) ?
H5A N5 H5B 121.(4) ?
C10 N6 H6A 120.(3) ?
C10 N6 H6B 126.(3) ?
H6A N6 H6B 114.(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.268(3) y
O1 H7 1.41(3) ?
O2 C2 1.305(4) y
O2 H2 1.04(3) ?
O3 C3 1.238(3) y
O4 C4 1.233(3) y
O6 C6 1.237(3) y
O7 C7 1.306(3) y
O7 H7 1.06(3) ?
O8 C8 1.271(3) y
O9 C9 1.234(4) y
C1 C2 1.410(4) y
C1 C4 1.478(4) y
C2 C3 1.456(4) y
C3 C4 1.497(4) y
C5 N3 1.319(4) ?
C5 N2 1.326(4) ?
C5 N1 1.332(4) ?
N1 H1A 0.86(2) ?
N1 H1B 0.89(2) ?
N2 H2A 0.89(2) ?
N2 H2B 0.86(2) ?
N3 H3A 0.87(2) ?
N3 H3B 0.85(2) ?
C6 C7 1.444(4) y
C6 C9 1.494(4) y
C7 C8 1.430(4) y
C8 C9 1.466(4) y
C10 N4 1.318(4) ?
C10 N6 1.324(4) ?
C10 N5 1.328(4) ?
N4 H4A 0.90(2) ?
N4 H4B 0.88(2) ?
N5 H5A 0.91(2) ?
N5 H5B 0.86(2) ?
N6 H6A 0.88(2) ?
N6 H6B 0.89(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
O1 C1 C2 O2 -1.5(5)
C4 C1 C2 O2 179.1(3)
O1 C1 C2 C3 178.3(3)
C4 C1 C2 C3 -1.1(2)
O2 C2 C3 O3 1.7(6)
C1 C2 C3 O3 -178.0(3)
O2 C2 C3 C4 -179.1(3)
C1 C2 C3 C4 1.1(2)
O1 C1 C4 O4 1.6(6)
C2 C1 C4 O4 -179.1(4)
O1 C1 C4 C3 -178.3(3)
C2 C1 C4 C3 1.1(2)
O3 C3 C4 O4 -1.7(6)
C2 C3 C4 O4 179.1(3)
O3 C3 C4 C1 178.1(3)
C2 C3 C4 C1 -1.1(2)
O6 C6 C7 O7 0.3(6)
C9 C6 C7 O7 179.9(3)
O6 C6 C7 C8 -179.5(4)
C9 C6 C7 C8 0.1(2)
O7 C7 C8 O8 0.5(7)
C6 C7 C8 O8 -179.7(4)
O7 C7 C8 C9 -179.9(4)
C6 C7 C8 C9 -0.1(2)
O8 C8 C9 O9 1.1(6)
C7 C8 C9 O9 -178.5(4)
O8 C8 C9 C6 179.7(3)
C7 C8 C9 C6 0.1(2)
O6 C6 C9 O9 -2.0(7)
C7 C6 C9 O9 178.4(4)
O6 C6 C9 C8 179.5(4)
C7 C6 C9 C8 -0.1(2)