#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/62/2006226.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
'Tsonko Kolev'
'Hans Preut'
'Paul Bleckmann'
'Valentina Radomirska'
_publ_contact_author
;       Dr. Hans Preut
        Fachbereich Chemie
        Universität 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_paper_doi               10.1107/S0108270197001182
_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       ω--2θ
_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      ?
_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          .0562
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1026P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1983
_refine_ls_wR_factor_obs         .1528
_reflns_number_observed          1681
_reflns_number_total             2588
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jz1154.cif
_cod_data_source_block           nic412
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.1026P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed
to 'calc'. New tag '_refine_ls_weighting_details' was created. The
value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.1026P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1460.6(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_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_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_disorder_group
_atom_site_type_symbol
O1 .3721(3) .57106(10) .1821(3) .0374(6) Uani d . 1 . O
O2 .4363(2) .42710(10) .0942(3) .0391(6) Uani d D 1 . O
H2 .426(4) .3833(15) .028(4) .059 Uiso d D 1 . H
O3 .1183(3) .42354(10) -.2034(3) .0408(6) Uani d . 1 . O
O4 .0585(3) .57444(10) -.1219(3) .0417(6) Uani d . 1 . O
O6 .2905(3) .83976(10) .1866(3) .0452(6) Uani d . 1 . O
O7 .2847(3) .68473(10) .1827(3) .0417(6) Uani d D 1 . O
H7 .325(4) .6367(15) .177(5) .063 Uiso d D 1 . H
O8 .5975(3) .68430(10) .0285(3) .0435(6) Uani d . 1 . O
O9 .6000(3) .83815(11) .0298(3) .0541(7) Uani d . 1 . O
C1 .2996(3) .53234(13) .0711(3) .0291(7) Uani d . 1 . C
C2 .3255(3) .46721(13) .0301(3) .0292(7) Uani d . 1 . C
C3 .1866(3) .46459(13) -.1027(3) .0287(7) Uani d . 1 . C
C4 .1585(3) .53415(14) -.0638(3) .0300(7) Uani d . 1 . C
C5 .2414(3) .50504(14) .4935(3) .0334(7) Uani d . 1 . C
N1 .3702(3) .50831(15) .6127(4) .0453(7) Uani d D 1 . N
H1A .384(5) .5438(14) .671(5) .068 Uiso d D 1 . H
H1B .425(4) .4717(14) .628(5) .068 Uiso d D 1 . H
N2 .2104(3) .45196(14) .3993(3) .0411(7) Uani d D 1 . N
H2A .124(3) .4487(19) .319(4) .062 Uiso d D 1 . H
H2B .275(4) .4204(15) .423(5) .062 Uiso d D 1 . H
N3 .1454(3) .55463(14) .4721(4) .0444(7) Uani d D 1 . N
H3A .064(3) .5551(19) .390(4) .067 Uiso d D 1 . H
H3B .178(4) .5883(14) .531(4) .067 Uiso d D 1 . H
C6 .3736(4) .79811(14) .1432(4) .0344(7) Uani d . 1 . C
C7 .3759(3) .72780(13) .1393(4) .0298(7) Uani d . 1 . C
C8 .5108(3) .72652(13) .0732(4) .0299(7) Uani d . 1 . C
C9 .5144(4) .79789(14) .0738(4) .0351(7) Uani d . 1 . C
C10 .0632(4) .24301(14) .6229(4) .0339(7) Uani d . 1 . C
N4 -.0590(4) .2398(2) .6875(4) .0480(8) Uani d D 1 . N
H4A -.105(4) .2019(14) .702(5) .072 Uiso d D 1 . H
H4B -.099(4) .2744(15) .726(5) .072 Uiso d D 1 . H
N5 .1399(4) .29836(13) .6236(4) .0447(7) Uani d D 1 . N
H5A .123(5) .3346(14) .681(4) .067 Uiso d D 1 . H
H5B .216(4) .2964(19) .574(5) .067 Uiso d D 1 . H
N6 .1080(4) .19036(13) .5533(4) .0451(8) Uani d D 1 . N
H6A .054(4) .1543(14) .547(5) .068 Uiso d D 1 . H
H6B .193(4) .1864(18) .515(5) .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_site_symmetry_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 . .86(2) ?
N1 H1B . .89(2) ?
N2 H2A . .89(2) ?
N2 H2B . .86(2) ?
N3 H3A . .87(2) ?
N3 H3B . .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 . .90(2) ?
N4 H4B . .88(2) ?
N5 H5A . .91(2) ?
N5 H5B . .86(2) ?
N6 H6A . .88(2) ?
N6 H6B . .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)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652169
