#------------------------------------------------------------------------------
#$Date: 2017-11-23 20:17:22 +0200 (Thu, 23 Nov 2017) $
#$Revision: 203508 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/71/2017104.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_2017104
loop_
_publ_author_name
'Sridhar, Balasubramanian'
'Ravikumar, Krishnan'
'Varghese, Babu'
_publ_section_title
;
 Supramolecular hydrogen-bonded networks in adeninediium hemioxalate
 chloride and adeninium semioxalate hemi(oxalic acid) monohydrate
;
_journal_coeditor_code           LN3126
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o202
_journal_page_last               o206
_journal_paper_doi               10.1107/S0108270109011780
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C5 H6 N5 + , C2 H O4 - , 0.5C2 H2 O4 , H2 O'
_chemical_formula_moiety         'C5 H6 N5 + , C2 H O4 - , 0.5C2 H2 O4 , H2 O'
_chemical_formula_sum            'C8 H10 N5 O7'
_chemical_formula_weight         288.21
_chemical_name_common
;
Adeninium oxalate hemioxalic acid hydrate
;
_chemical_name_systematic
;
adeninium oxalate hemi(oxalic acid) monohydrate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.696(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.6222(3)
_cell_length_b                   28.131(3)
_cell_length_c                   11.1101(10)
_cell_measurement_reflns_used    6401
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.35
_cell_volume                     1119.06(18)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10683
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.233
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         1982
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0374
_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)+(0.0490P)²+0.5164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                1891
_reflns_number_total             1982
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln3126.cif
_cod_data_source_block           II
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-11-23
;
_cod_original_cell_volume        1119.05(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017104
_cod_database_fobs_code          2017104
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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C C2 0.3057(5) 0.65002(6) 0.01285(16) 0.0312(4) Uani d . 1 . . 0
H H2 0.1722 0.6407 -0.0615 0.037 Uiso calc R 1 . . 0
C C4 0.5714(5) 0.70469(6) 0.13987(15) 0.0269(4) Uani d . 1 . . 0
C C5 0.7040(4) 0.67218(6) 0.22865(15) 0.0255(4) Uani d . 1 . . 0
C C6 0.6187(5) 0.62365(6) 0.20749(15) 0.0267(4) Uani d . 1 . . 0
C C8 0.8726(5) 0.74063(6) 0.29858(16) 0.0325(4) Uani d . 1 . . 0
H H8 0.9765 0.7649 0.3495 0.039 Uiso calc R 1 . . 0
N N1 0.4163(4) 0.61531(5) 0.09554(13) 0.0297(3) Uani d . 1 . . 0
H H1N 0.343(6) 0.5847(9) 0.080(2) 0.047(6) Uiso d . 1 . . 0
N N3 0.3710(4) 0.69523(5) 0.02899(13) 0.0318(4) Uani d . 1 . . 0
N N7 0.8963(4) 0.69541(5) 0.32865(13) 0.0298(3) Uani d . 1 . . 0
N N9 0.6815(4) 0.74809(5) 0.18611(14) 0.0324(4) Uani d . 1 . . 0
H H9N 0.630(7) 0.7751(10) 0.153(2) 0.063(8) Uiso d . 1 . . 0
N N10 0.7156(5) 0.58903(6) 0.28362(15) 0.0382(4) Uani d . 1 . . 0
H H10 0.839(7) 0.5947(9) 0.356(2) 0.053(7) Uiso d . 1 . . 0
H H11 0.658(7) 0.5582(9) 0.264(2) 0.055(7) Uiso d . 1 . . 0
C C11 1.2953(5) 0.63238(6) 0.57708(15) 0.0302(4) Uani d . 1 . . 0
C C12 1.5343(5) 0.62201(6) 0.70148(16) 0.0295(4) Uani d . 1 . . 0
O O1 1.7325(4) 0.65301(4) 0.75259(12) 0.0418(4) Uani d . 1 . . 0
O O2 1.4950(4) 0.57968(5) 0.73755(12) 0.0440(4) Uani d . 1 . . 0
O O3 1.3244(4) 0.67583(4) 0.53995(12) 0.0412(4) Uani d . 1 . . 0
H H3O 1.155(10) 0.6778(12) 0.461(3) 0.113(12) Uiso d . 1 . . 0
O O4 1.1022(4) 0.60221(5) 0.52236(12) 0.0457(4) Uani d . 1 . . 0
C C13 1.8746(5) 0.50930(6) 0.94231(15) 0.0275(4) Uani d . 1 . . 0
O O5 1.8981(4) 0.55387(4) 0.92541(11) 0.0359(3) Uani d . 1 . . 0
H H5O 1.704(9) 0.5678(12) 0.833(3) 0.110(11) Uiso d . 1 . . 0
O O6 1.6739(4) 0.48122(4) 0.87839(12) 0.0393(4) Uani d . 1 . . 0
O O7 0.697(4) 0.50019(15) 0.4161(8) 0.112(3) Uani d PU 0.622(19) A 1 2
O O7' 0.939(5) 0.4985(2) 0.3730(11) 0.089(4) Uani d PU 0.378(19) A 2 2
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 C2 N1 . . 125.48(16) ?
N3 C2 H2 . . 117.3 ?
N1 C2 H2 . . 117.3 ?
N3 C4 N9 . . 127.17(15) ?
N3 C4 C5 . . 126.89(15) ?
N9 C4 C5 . . 105.94(15) ?
C4 C5 N7 . . 109.90(14) ?
C4 C5 C6 . . 118.63(15) ?
N7 C5 C6 . . 131.43(15) ?
N10 C6 N1 . . 121.19(16) ?
N10 C6 C5 . . 125.75(16) ?
N1 C6 C5 . . 113.06(14) ?
N7 C8 N9 . . 112.96(15) ?
N7 C8 H8 . . 123.5 ?
N9 C8 H8 . . 123.5 ?
C2 N1 C6 . . 123.72(15) y
C2 N1 H1N . . 120.4(14) ?
C6 N1 H1N . . 115.7(14) ?
C2 N3 C4 . . 112.18(14) ?
C8 N7 C5 . . 104.32(14) y
C8 N9 C4 . . 106.86(14) ?
C8 N9 H9N . . 126.1(18) ?
C4 N9 H9N . . 126.9(18) ?
C6 N10 H10 . . 120.6(16) ?
C6 N10 H11 . . 121.6(15) ?
H10 N10 H11 . . 118(2) ?
O4 C11 O3 . . 124.86(16) y
O4 C11 C12 . . 121.54(16) ?
O3 C11 C12 . . 113.61(15) ?
O1 C12 O2 . . 127.72(16) y
O1 C12 C11 . . 119.65(15) ?
O2 C12 C11 . . 112.63(15) ?
C12 O2 H5O . . 115.7(16) ?
C11 O3 H3O . . 105(2) ?
O6 C13 O5 . . 126.64(15) y
O6 C13 C13 . 3_967 119.03(18) ?
O5 C13 C13 . 3_967 114.32(17) ?
C13 O5 H5O . . 113.5(16) ?
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
C2 N3 . 1.301(2) ?
C2 N1 . 1.359(2) ?
C2 H2 . 0.9300 ?
C4 N3 . 1.358(2) ?
C4 N9 . 1.361(2) ?
C4 C5 . 1.377(2) ?
C5 N7 . 1.383(2) ?
C5 C6 . 1.412(2) ?
C6 N10 . 1.303(2) ?
C6 N1 . 1.365(2) ?
C8 N7 . 1.315(2) ?
C8 N9 . 1.350(2) ?
C8 H8 . 0.9300 ?
N1 H1N . 0.91(2) ?
N9 H9N . 0.85(3) ?
N10 H10 . 0.87(3) ?
N10 H11 . 0.91(3) ?
C11 O4 . 1.204(2) y
C11 O3 . 1.299(2) y
C11 C12 . 1.544(2) ?
C12 O1 . 1.214(2) y
C12 O2 . 1.271(2) y
O2 H5O . 1.25(4) ?
O3 H3O . 1.00(4) ?
C13 O6 . 1.225(2) y
C13 O5 . 1.273(2) y
C13 C13 3_967 1.546(3) ?
O5 H5O . 1.22(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
N1 H1N O6 3_766 0.91(2) 1.91(2) 2.755(2) 153(2)
N1 H1N O5 1_354 0.91(2) 2.34(2) 3.002(2) 130(2)
N9 H9N O3 4_475 0.85(3) 2.07(3) 2.873(2) 157(2)
N9 H9N O1 4_475 0.85(3) 2.31(3) 2.877(2) 124(2)
N10 H10 O4 . 0.87(3) 1.96(3) 2.830(2) 175(2)
N10 H11 O6 3_766 0.91(3) 2.14(3) 2.893(2) 139(2)
N10 H11 O7' . 0.91(3) 2.23(3) 2.807(6) 121(2)
N10 H11 O7 . 0.91(3) 2.34(3) 2.906(6) 120(2)
O3 H3O N7 . 1.00(4) 1.69(4) 2.668(2) 166(3)
O5 H5O O2 . 1.22(4) 1.25(4) 2.469(2) 176(3)
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
N3 C4 C5 N7 . . . . 179.80(16) ?
N9 C4 C5 N7 . . . . -0.32(19) ?
N3 C4 C5 C6 . . . . -2.2(3) ?
N9 C4 C5 C6 . . . . 177.64(15) ?
C4 C5 C6 N10 . . . . -178.13(17) ?
N7 C5 C6 N10 . . . . -0.7(3) ?
C4 C5 C6 N1 . . . . 1.8(2) ?
N7 C5 C6 N1 . . . . 179.20(17) ?
N3 C2 N1 C6 . . . . -1.1(3) ?
N10 C6 N1 C2 . . . . 179.58(17) ?
C5 C6 N1 C2 . . . . -0.3(2) ?
N1 C2 N3 C4 . . . . 0.8(3) ?
N9 C4 N3 C2 . . . . -178.96(17) ?
C5 C4 N3 C2 . . . . 0.9(3) ?
N9 C8 N7 C5 . . . . -0.5(2) ?
C4 C5 N7 C8 . . . . 0.50(19) ?
C6 C5 N7 C8 . . . . -177.11(18) ?
N7 C8 N9 C4 . . . . 0.3(2) ?
N3 C4 N9 C8 . . . . 179.89(17) ?
C5 C4 N9 C8 . . . . 0.0(2) ?
O4 C11 C12 O1 . . . . 178.23(18) ?
O3 C11 C12 O1 . . . . -2.0(2) ?
O4 C11 C12 O2 . . . . -1.4(3) ?
O3 C11 C12 O2 . . . . 178.41(16) ?
