#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/60/2016033.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_2016033
loop_
_publ_author_name
'Balasubramanian Sridhar'
'Krishnan Ravikumar'
_publ_section_title
;
 Supramolecular hydrogen-bonded networks in adeninium phenylacetate
 phenylacetic acid monohydrate and adeninium 3-carboxypropionate
 monohydrate
;
_journal_coeditor_code           GA3054
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o415
_journal_page_last               o418
_journal_paper_doi               10.1107/S0108270107024493
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C5 H6 N5 + , C4 H3 O4 - , H2 O'
_chemical_formula_moiety         'C5 H6 N5 + , C4 H3 O4 - , H2 O'
_chemical_formula_sum            'C9 H11 N5 O5'
_chemical_formula_weight         269.23
_chemical_name_common            'Adeninium succinate hydrate'
_chemical_name_systematic
;
adeninium 3-carboxypropionate 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                 100.503(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.539(3)
_cell_length_b                   17.149(6)
_cell_length_c                   7.450(3)
_cell_measurement_reflns_used    8119
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.02
_cell_measurement_theta_min      2.47
_cell_volume                     1198.3(7)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_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 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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10914
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SABABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.243
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2112
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0786P)²+0.1186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                1934
_reflns_number_total             2112
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ga3054.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016033
_cod_database_fobs_code          2016033
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
C C2 0.30508(17) 0.71386(10) 0.8304(2) 0.0553(4) Uani d . 1
H H2 0.3819 0.7387 0.7940 0.066 Uiso calc R 1
C C4 0.09829(16) 0.71472(9) 0.92531(18) 0.0451(4) Uani d . 1
C C5 0.09084(14) 0.63397(8) 0.93719(18) 0.0429(3) Uani d . 1
C C6 0.20234(15) 0.58941(8) 0.88586(18) 0.0434(3) Uani d . 1
C C8 -0.09487(17) 0.67875(9) 1.0206(2) 0.0530(4) Uani d . 1
H H8 -0.1811 0.6823 1.0617 0.064 Uiso calc R 1
N N1 0.30705(13) 0.63444(8) 0.83389(17) 0.0506(3) Uani d D 1
H H1N 0.3853(15) 0.6137(12) 0.797(2) 0.073(6) Uiso d D 1
N N3 0.20488(15) 0.75821(8) 0.87348(19) 0.0541(4) Uani d . 1
N N7 -0.03211(13) 0.61135(7) 0.99833(17) 0.0499(3) Uani d . 1
N N9 -0.02190(14) 0.74226(8) 0.97801(19) 0.0508(3) Uani d . 1
H H9N -0.043(2) 0.7913(16) 0.982(3) 0.078(6) Uiso d . 1
N N10 0.21206(15) 0.51274(7) 0.88423(18) 0.0514(3) Uani d . 1
H H10A 0.292(2) 0.4910(14) 0.854(3) 0.081(6) Uiso d . 1
H H10B 0.139(2) 0.4825(11) 0.919(2) 0.061(5) Uiso d . 1
C C11 0.56012(16) 0.49986(9) 0.7303(2) 0.0493(4) Uani d . 1
C C12 0.68762(16) 0.46488(9) 0.6682(2) 0.0484(4) Uani d . 1
H H12 0.6942 0.4109 0.6776 0.058 Uiso calc R 1
C C13 0.79349(16) 0.49941(9) 0.6012(2) 0.0487(4) Uani d . 1
H H13 0.8625 0.4653 0.5741 0.058 Uiso calc R 1
C C14 0.81954(16) 0.58309(8) 0.5628(2) 0.0490(4) Uani d . 1
O O1 0.54367(12) 0.57392(7) 0.72622(18) 0.0643(4) Uani d . 1
O O2 0.47499(13) 0.45476(7) 0.78448(17) 0.0641(4) Uani d . 1
O O3 0.73222(12) 0.63797(6) 0.59543(17) 0.0601(3) Uani d D 1
H H3O 0.6612(18) 0.6208(13) 0.646(3) 0.082(6) Uiso d D 1
O O4 0.92546(14) 0.59986(7) 0.4990(2) 0.0721(4) Uani d . 1
O O1W 0.5899(2) 0.70336(11) 0.1990(3) 0.1047(6) Uani d D 1
H H1W 0.539(4) 0.6619(16) 0.155(4) 0.23(2) Uiso d D 1
H H2W 0.6375 0.7020 0.3096 0.098 Uiso d D 1
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
N3 C2 N1 125.83(14) ?
N3 C2 H2 117.1 ?
N1 C2 H2 117.1 ?
N9 C4 N3 126.76(14) ?
N9 C4 C5 105.75(13) ?
N3 C4 C5 127.48(13) ?
N7 C5 C4 110.81(12) ?
N7 C5 C6 131.15(13) ?
C4 C5 C6 118.04(12) ?
N10 C6 N1 120.16(13) ?
N10 C6 C5 126.69(13) ?
N1 C6 C5 113.15(13) ?
N7 C8 N9 113.99(14) ?
N7 C8 H8 123.0 ?
N9 C8 H8 123.0 ?
C2 N1 C6 124.03(13) y
C2 N1 H1N 113.1(14) ?
C6 N1 H1N 122.9(14) ?
C2 N3 C4 111.45(13) ?
C8 N7 C5 103.01(12) ?
C8 N9 C4 106.44(13) ?
C8 N9 H9N 129.6(16) ?
C4 N9 H9N 123.9(16) ?
C6 N10 H10A 118.3(15) ?
C6 N10 H10B 119.3(12) ?
H10A N10 H10B 122.3(19) ?
O2 C11 O1 122.79(14) y
O2 C11 C12 117.76(14) y
O1 C11 C12 119.45(13) y
C13 C12 C11 130.10(14) ?
C13 C12 H12 115.0 ?
C11 C12 H12 115.0 ?
C12 C13 C14 131.14(14) ?
C12 C13 H13 114.4 ?
C14 C13 H13 114.4 ?
O4 C14 O3 120.04(14) y
O4 C14 C13 118.51(13) y
O3 C14 C13 121.45(13) y
C14 O3 H3O 113.8(16) ?
H1W O1W H2W 119 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 N3 1.307(2) ?
C2 N1 1.362(2) ?
C2 H2 0.9300 ?
C4 N9 1.362(2) ?
C4 N3 1.372(2) ?
C4 C5 1.390(2) ?
C5 N7 1.3886(18) ?
C5 C6 1.418(2) ?
C6 N10 1.318(2) ?
C6 N1 1.3730(19) ?
C8 N7 1.326(2) ?
C8 N9 1.361(2) ?
C8 H8 0.9300 ?
N1 H1N 0.914(10) ?
N9 H9N 0.87(3) ?
N10 H10A 0.91(2) ?
N10 H10B 0.943(19) ?
C11 O2 1.2410(19) y
C11 O1 1.279(2) y
C11 C12 1.503(2) ?
C12 C13 1.343(2) ?
C12 H12 0.9300 ?
C13 C14 1.493(2) ?
C13 H13 0.9300 ?
C14 O4 1.2266(19) ?
C14 O3 1.3087(18) ?
O3 H3O 0.883(10) ?
O1W H1W 0.89(3) ?
O1W H2W 0.87 ?
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 O1 . 0.914(10) 1.821(16) 2.734(2) 179(2)
N9 H9N O4 4_476 0.87(3) 1.90(3) 2.763(2) 176(2)
N10 H10A O2 . 0.91(2) 2.01(2) 2.917(2) 174(2)
N10 H10B N7 3_567 0.943(19) 2.06(2) 2.964(2) 161(2)
O3 H3O O1 . 0.883(10) 1.583(11) 2.4557(17) 169(2)
O1W H1W O2 3_666 0.89(3) 2.06(2) 2.789(2) 138(2)
O1W H2W O3 . 0.87 2.42 3.219(3) 154
C2 H2 O1W 4_576 0.93 2.44 3.365(3) 176.7
C13 H13 O4 3_766 0.93 2.46 3.372(2) 168.0
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
_geom_torsion_publ_flag
N9 C4 C5 N7 -0.55(16) ?
N3 C4 C5 N7 178.76(14) ?
N9 C4 C5 C6 178.68(12) ?
N3 C4 C5 C6 -2.0(2) ?
N7 C5 C6 N10 0.6(2) ?
C4 C5 C6 N10 -178.43(14) ?
N7 C5 C6 N1 -179.49(13) ?
C4 C5 C6 N1 1.46(18) ?
N3 C2 N1 C6 -0.6(2) ?
N10 C6 N1 C2 179.56(14) ?
C5 C6 N1 C2 -0.3(2) ?
N1 C2 N3 C4 0.3(2) ?
N9 C4 N3 C2 -179.76(14) ?
C5 C4 N3 C2 1.1(2) ?
N9 C8 N7 C5 0.20(18) ?
C4 C5 N7 C8 0.23(16) ?
C6 C5 N7 C8 -178.87(15) ?
N7 C8 N9 C4 -0.55(19) ?
N3 C4 N9 C8 -178.68(14) ?
C5 C4 N9 C8 0.64(16) ?
O2 C11 C12 C13 178.74(15) ?
O1 C11 C12 C13 -1.5(2) ?
C11 C12 C13 C14 -1.2(3) y
C12 C13 C14 O4 -179.32(17) ?
C12 C13 C14 O3 0.6(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654063
2 PubChem 139060153
