#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/45/2214536.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_2214536
loop_
_publ_author_name
'Bojidarka Koleva'
'Tsanko Tsanev'
'Tsonko Kolev'
'Heike Mayer-Figge'
'William S. Sheldrick'
_publ_section_title
;
 3,4-Diaminopyridinium hydrogen squarate
;
_journal_coeditor_code           BT2412
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3356
_journal_page_last               o3356
_journal_paper_doi               10.1107/S1600536807031170
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C5 H8 N3 +, C4 H O4 -'
_chemical_formula_moiety         'C5 H8 N3 +, C4 H O4 -'
_chemical_formula_sum            'C9 H9 N3 O4'
_chemical_formula_weight         223.19
_chemical_name_systematic
;
3,4-Diaminopyridinium hydrogen squarate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.56(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.069(2)
_cell_length_b                   7.1925(14)
_cell_length_c                   13.480(3)
_cell_measurement_reflns_used    27
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      7.5
_cell_volume                     969.8(4)
_computing_cell_refinement       R3m/V
_computing_data_collection       'R3m/V (Siemens, 1989)'
_computing_data_reduction        'XDISK (Siemens, 1989)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1995)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Siemens P4 four-circle'
_diffrn_measurement_method       ω
_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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2310
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.93837
_exptl_absorpt_correction_T_min  0.84350
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XPREP; Sheldrick, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prsim
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.375
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0946P)²+0.5492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1890
_reflns_number_gt                1172
_reflns_number_total             1698
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2412.cif
_cod_data_source_block           I
_cod_original_cell_volume        969.8(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214536
_cod_database_fobs_code          2214536
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_type_symbol
_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
N N1 0.7328(3) 0.3740(5) 1.0145(2) 0.0559(9) Uani d . 1
H H1 0.6586 0.3990 1.0375 0.067 Uiso calc R 1
C C2 0.8249(3) 0.2759(5) 1.0705(3) 0.0520(9) Uani d . 1
H H2 0.8086 0.2368 1.1338 0.062 Uiso calc R 1
C C3 0.9425(3) 0.2325(5) 1.0359(2) 0.0472(9) Uani d . 1
H H3 1.0057 0.1624 1.0754 0.057 Uiso calc R 1
N N2 1.0874(2) 0.2506(4) 0.9064(2) 0.0498(8) Uani d . 1
H H21 1.1031 0.2865 0.8480 0.060 Uiso calc R 1
H H22 1.1465 0.1877 0.9434 0.060 Uiso calc R 1
C C4 0.9699(3) 0.2929(5) 0.9401(2) 0.0400(8) Uani d . 1
N N3 0.8886(3) 0.4537(5) 0.7857(2) 0.0568(9) Uani d . 1
H H31 0.8270 0.5150 0.7503 0.068 Uiso calc R 1
H H32 0.9620 0.4277 0.7619 0.068 Uiso calc R 1
C C5 0.8693(3) 0.3965(5) 0.8816(2) 0.0403(8) Uani d . 1
C C6 0.7522(3) 0.4362(5) 0.9219(3) 0.0511(9) Uani d . 1
H H6 0.6860 0.5061 0.8854 0.061 Uiso calc R 1
C C1' 0.2926(3) 0.0429(5) 0.2041(2) 0.0429(8) Uani d . 1
O O1' 0.1804(2) 0.0879(4) 0.22347(18) 0.0579(8) Uani d . 1
C C2' 0.3618(3) 0.0417(5) 0.1124(2) 0.0417(8) Uani d . 1
O O2' 0.3283(2) 0.0894(4) 0.02326(16) 0.0519(7) Uani d . 1
C C3' 0.4780(3) -0.0317(5) 0.1697(2) 0.0414(8) Uani d . 1
O O3' 0.5998(2) -0.0799(4) 0.15119(17) 0.0576(8) Uani d . 1
H H3' 0.6030 -0.0814 0.0907 0.086 Uiso calc R 1
C C4' 0.4173(3) -0.0327(5) 0.2619(3) 0.0465(9) Uani d . 1
O O4' 0.4548(2) -0.0753(4) 0.34977(18) 0.0589(8) Uani d . 1
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
N1 0.0358(14) 0.072(2) 0.062(2) -0.0045(15) 0.0139(13) -0.0134(18)
C2 0.049(2) 0.060(2) 0.048(2) -0.0107(18) 0.0109(16) -0.0025(18)
C3 0.0440(17) 0.052(2) 0.0449(19) -0.0018(16) 0.0021(14) -0.0001(17)
N2 0.0357(14) 0.063(2) 0.0504(17) 0.0070(13) 0.0061(12) 0.0012(15)
C4 0.0335(15) 0.0413(18) 0.0444(18) -0.0026(14) 0.0012(13) -0.0080(15)
N3 0.0509(17) 0.076(2) 0.0430(17) 0.0126(16) 0.0020(13) 0.0090(16)
C5 0.0364(16) 0.0447(19) 0.0389(17) -0.0023(14) -0.0003(13) -0.0048(15)
C6 0.0375(17) 0.056(2) 0.058(2) 0.0015(16) -0.0040(15) -0.0087(19)
C1' 0.0296(15) 0.053(2) 0.0465(18) -0.0003(14) 0.0043(13) -0.0021(16)
O1' 0.0304(11) 0.090(2) 0.0544(14) 0.0110(12) 0.0107(10) 0.0002(14)
C2' 0.0284(15) 0.053(2) 0.0438(18) 0.0011(14) 0.0040(13) -0.0060(16)
O2' 0.0322(11) 0.0770(18) 0.0462(14) 0.0142(11) 0.0023(9) -0.0022(13)
C3' 0.0277(14) 0.056(2) 0.0415(18) 0.0034(14) 0.0076(12) -0.0001(16)
O3' 0.0303(11) 0.094(2) 0.0500(14) 0.0170(12) 0.0092(10) 0.0092(14)
C4' 0.0272(15) 0.059(2) 0.053(2) 0.0003(15) 0.0026(14) -0.0006(18)
O4' 0.0330(12) 0.095(2) 0.0495(14) 0.0065(12) 0.0070(10) 0.0134(14)
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
C2 N1 C6 122.1(3)
C2 N1 H1 118.9
C6 N1 H1 118.9
N1 C2 C3 120.4(3)
N1 C2 H2 119.8
C3 C2 H2 119.8
C2 C3 C4 120.7(3)
C2 C3 H3 119.7
C4 C3 H3 119.7
C4 N2 H21 120.0
C4 N2 H22 120.0
H21 N2 H22 120.0
N2 C4 C5 121.9(3)
N2 C4 C3 120.4(3)
C5 C4 C3 117.7(3)
C5 N3 H31 120.0
C5 N3 H32 120.0
H31 N3 H32 120.0
C6 C5 N3 121.3(3)
C6 C5 C4 118.4(3)
N3 C5 C4 120.3(3)
N1 C6 C5 120.7(3)
N1 C6 H6 119.7
C5 C6 H6 119.7
O1' C1' C2' 134.9(3)
O1' C1' C4' 135.9(3)
C2' C1' C4' 89.2(2)
O2' C2' C3' 137.0(3)
O2' C2' C1' 133.8(3)
C3' C2' C1' 89.2(3)
O3' C3' C2' 135.6(3)
O3' C3' C4' 130.7(3)
C2' C3' C4' 93.8(2)
C3' O3' H3' 109.5
O4' C4' C3' 135.2(3)
O4' C4' C1' 136.9(3)
C3' C4' C1' 87.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.330(5)
N1 C6 1.360(5)
N1 H1 0.8600
C2 C3 1.358(5)
C2 H2 0.9300
C3 C4 1.420(5)
C3 H3 0.9300
N2 C4 1.349(4)
N2 H21 0.8600
N2 H22 0.8600
C4 C5 1.421(4)
N3 C5 1.391(4)
N3 H31 0.8600
N3 H32 0.8600
C5 C6 1.383(4)
C6 H6 0.9300
C1' O1' 1.232(4)
C1' C2' 1.486(4)
C1' C4' 1.501(4)
C2' O2' 1.259(4)
C2' C3' 1.427(4)
C3' O3' 1.325(3)
C3' C4' 1.446(4)
O3' H3' 0.8200
C4' O4' 1.241(4)
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
O3' H3' O2' 3_655 0.82 1.76 2.539(3) 159.2 y
N2 H21 O1' 4_666 0.86 2.13 2.972(4) 166.0 y
N1 H1 O4' 2_656 0.86 2.01 2.799(4) 152.1 y
N2 H22 O2' 1_656 0.86 2.14 2.973(3) 164.4 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655286
