#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/37/2103718.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_2103718
loop_
_publ_author_name
'Bertolasi, Valerio'
'Gilli, Paola'
'Ferretti, Valeria'
'Gilli, Gastone'
_publ_section_title
;
 General rules for the packing of hydrogen-bonded crystals as derived
 from the analysis of squaric acid anions: aminoaromatic nitrogen base
 co-crystals
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              591
_journal_page_last               598
_journal_paper_doi               10.1107/S010876810100814X
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C4 H6 N3, C4 H O4'
_chemical_formula_sum            'C8 H7 N3 O4'
_chemical_formula_weight         209.17
_chemical_name_systematic
;
2-aminopyridinium hydrogen squarate, 1:1
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.72(2)
_cell_angle_beta                 104.05(2)
_cell_angle_gamma                87.730(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2790(10)
_cell_length_b                   10.1840(10)
_cell_length_c                   5.353(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      8
_cell_volume                     431.54(18)
_computing_cell_refinement       'CAD4 Enraf-Nonius, 1984'
_computing_data_collection       'CAD4 (Enraf-Nonius, 1984)'
_computing_data_reduction        'MolEN (Fair, 1990; Enraf-Nonius, 1990)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
;
PARST (Nardelli, 1983, 1995),  SHELXL-97 (Sheldrick, 1997)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .013
_diffrn_reflns_av_sigmaI/netI    .0230
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2769
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .132
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             216
_exptl_crystal_size_max          .52
_exptl_crystal_size_mid          .36
_exptl_crystal_size_min          .10
_refine_diff_density_max         .341
_refine_diff_density_min         -.330
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          .0659
_refine_ls_R_factor_gt           .0498
_refine_ls_shift/su_max          .003
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1114P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1496
_reflns_number_gt                1596
_reflns_number_total             2078
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            na0121.cif
_cod_data_source_block           1
_cod_original_cell_volume        431.5(2)
_cod_database_code               2103718
_cod_database_fobs_code          2103718
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_occupancy
_atom_site_type_symbol
O1 .29393(18) .12644(14) -.1800(3) .0487(4) Uani d 1 O
O2 .58959(16) .09413(12) .3332(2) .0415(4) Uani d 1 O
O3 .47929(16) .36437(12) .6376(2) .0409(3) Uani d 1 O
O4 .18791(17) .40146(13) .1066(3) .0469(4) Uani d 1 O
C1 .3493(2) .19378(16) .0535(3) .0315(4) Uani d 1 C
C2 .4760(2) .17740(15) .2742(3) .0301(4) Uani d 1 C
C3 .4280(2) .30333(15) .4165(3) .0299(4) Uani d 1 C
C4 .2944(2) .31983(16) .1741(3) .0314(4) Uani d 1 C
N1 .74921(18) .29039(13) 1.0142(3) .0325(3) Uani d 1 N
N2 .96332(17) .15882(14) 1.2202(3) .0313(3) Uani d 1 N
N3 .8191(2) .08904(16) .7977(3) .0407(4) Uani d 1 N
C5 .8434(2) .17901(16) 1.0099(3) .0294(4) Uani d 1 C
C6 .7655(2) .38114(16) 1.2329(4) .0359(4) Uani d 1 C
C7 .8801(2) .36211(17) 1.4511(3) .0377(4) Uani d 1 C
C8 .9793(2) .24902(18) 1.4319(3) .0360(4) Uani d 1 C
H1 .354(3) .047(2) -.209(5) .060(7) Uiso d 1 H
H6 .688(3) .459(2) 1.212(4) .042(5) Uiso d 1 H
H7 .888(3) .425(3) 1.600(5) .057(7) Uiso d 1 H
H8 1.073(3) .234(2) 1.592(5) .058(7) Uiso d 1 H
H10 .664(3) .302(3) .868(5) .057(7) Uiso d 1 H
H31 .889(3) .017(2) .798(4) .040(5) Uiso d 1 H
H32 .740(3) .092(2) .645(5) .053(6) 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
O1 .0570(8) .0386(7) .0306(7) .0181(6) -.0149(6) -.0085(5)
O2 .0431(7) .0366(6) .0306(6) .0166(5) -.0086(5) -.0051(5)
O3 .0471(7) .0386(7) .0269(6) .0113(5) -.0008(5) -.0060(5)
O4 .0486(8) .0409(7) .0422(7) .0217(6) .0010(6) .0014(6)
C1 .0322(8) .0294(7) .0264(8) .0049(6) -.0013(6) .0001(6)
C2 .0311(8) .0277(7) .0259(7) .0043(6) .0004(6) -.0010(6)
C3 .0305(8) .0290(7) .0270(8) .0051(6) .0035(6) .0021(6)
C4 .0317(8) .0305(8) .0283(8) .0054(6) .0037(6) .0007(6)
N1 .0345(7) .0309(7) .0287(7) .0086(5) .0028(6) .0049(5)
N2 .0310(7) .0318(7) .0254(7) .0074(5) -.0006(5) .0009(5)
N3 .0478(9) .0374(8) .0255(8) .0143(7) -.0050(6) -.0030(6)
C5 .0307(8) .0305(8) .0247(8) .0051(6) .0034(6) .0037(6)
C6 .0421(9) .0241(7) .0426(10) .0071(6) .0155(7) .0022(7)
C7 .0456(10) .0319(8) .0321(9) -.0019(7) .0096(7) -.0056(7)
C8 .0367(9) .0379(9) .0278(8) -.0006(7) .0015(7) -.0008(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 '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
C1 O1 H1 112.3(16)
O1 C1 C2 135.96(15)
O1 C1 C4 129.96(15)
C2 C1 C4 94.08(13)
O1 C1 C3 177.85(14)
C2 C1 C3 46.14(9)
C4 C1 C3 47.96(9)
O2 C2 C1 136.68(15)
O2 C2 C3 133.00(15)
C1 C2 C3 90.29(13)
O3 C3 C2 133.68(15)
O3 C3 C4 137.69(15)
C2 C3 C4 88.62(13)
O3 C3 C1 177.19(14)
C2 C3 C1 43.57(9)
C4 C3 C1 45.06(9)
O4 C4 C1 135.69(16)
O4 C4 C3 137.32(16)
C1 C4 C3 86.98(13)
C6 N1 C5 121.16(15)
C6 N1 H10 118.5(16)
C5 N1 H10 120.1(16)
C8 N2 C5 117.16(15)
C5 N3 H31 117.7(14)
C5 N3 H32 126.5(15)
H31 N3 H32 116(2)
N3 C5 N2 119.15(15)
N3 C5 N1 119.85(15)
N2 C5 N1 121.00(15)
N1 C6 C7 119.61(15)
N1 C6 H6 113.5(13)
C7 C6 H6 126.9(13)
C6 C7 C8 116.78(16)
C6 C7 H7 118.1(17)
C8 C7 H7 125.1(17)
N2 C8 C7 124.15(16)
N2 C8 H8 117.1(14)
C7 C8 H8 118.7(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.304(2)
O1 H1 .94(3)
O2 C2 1.2593(19)
O3 C3 1.223(2)
O4 C4 1.220(2)
C1 C2 1.405(2)
C1 C4 1.445(2)
C1 C3 2.038(2)
C2 C3 1.470(2)
C3 C4 1.516(2)
N1 C6 1.346(2)
N1 C5 1.351(2)
N1 H10 .94(3)
N2 C8 1.316(2)
N2 C5 1.347(2)
N3 C5 1.312(2)
N3 H31 .92(2)
N3 H32 .92(3)
C6 C7 1.351(3)
C6 H6 1.00(2)
C7 C8 1.392(2)
C7 H7 .93(3)
C8 H8 1.03(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654501
