#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/87/2018793.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_2018793
loop_
_publ_author_name
'Novotná, Radka'
'Trávníček, Zdeněk'
_publ_section_title
;
 Infinite ladder-like chains organized into a three-dimensional zigzag
 supramolecular architecture in 9-deazahypoxanthine
;
_journal_coeditor_code           SK3467
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              158
_journal_page_last               161
_journal_paper_doi               10.1107/S0108270112050767
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C6 H5 N3 O'
_chemical_formula_moiety         'C6 H5 N3 O'
_chemical_formula_sum            'C6 H5 N3 O'
_chemical_formula_weight         135.13
_chemical_name_common            9-deazahypoxanthine
_chemical_name_systematic
;
3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.69(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8315(12)
_cell_length_b                   19.976(5)
_cell_length_c                   6.3551(13)
_cell_measurement_reflns_used    1593
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.28
_cell_measurement_theta_min      3.05
_cell_volume                     593.3(2)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008) and DIAMOND (Brandenburg,
2011)
;
_computing_publication_material
;
publCIF (Westrip, 2010) and  PARST (Nardelli, 1995)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3611
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford Xcalibur diffractometer with Sapphire2 detector (large Be window)'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_sigmaI/netI    0.0689
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3740
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0485
_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)+(0.0548P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                693
_reflns_number_total             1050
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3467.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2018793
_cod_database_fobs_code          2018793
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
N N1 0.7585(4) 0.05060(9) 0.2910(3) 0.0185(5) Uani d . 1 1
H H1 0.8929 0.0201 0.3028 0.022 Uiso calc R 1 1
O O1 0.7935(3) 0.04177(8) 0.6563(2) 0.0220(4) Uani d . 1 1
C C2 0.6453(5) 0.07721(12) 0.0909(4) 0.0213(6) Uani d . 1 1
H H2 0.7187 0.0616 -0.0254 0.026 Uiso calc R 1 1
N N3 0.4440(4) 0.12250(10) 0.0454(3) 0.0215(5) Uani d . 1 1
C C4 0.3504(5) 0.14308(11) 0.2234(4) 0.0181(6) Uani d . 1 1
C C5 0.4583(5) 0.11720(12) 0.4322(4) 0.0173(5) Uani d . 1 1
C C6 0.6780(5) 0.06798(11) 0.4763(4) 0.0170(5) Uani d . 1 1
N N7 0.3190(4) 0.14745(9) 0.5707(3) 0.0193(5) Uani d . 1 1
H H7 0.3475 0.1396 0.7108 0.023 Uiso calc R 1 1
C C8 0.1282(5) 0.19201(12) 0.4504(4) 0.0209(6) Uani d . 1 1
H H8 0.0036 0.2197 0.5063 0.025 Uiso calc R 1 1
C C9 0.1421(5) 0.19112(12) 0.2378(4) 0.0212(6) Uani d . 1 1
H H9 0.0327 0.2177 0.1224 0.025 Uiso calc R 1 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
C2 N1 C6 124.7(2)
C2 N1 H1 117.7
C6 N1 H1 117.7
N3 C2 N1 125.4(2)
N3 C2 H2 117.3
N1 C2 H2 117.3
C2 N3 C4 113.9(2)
N3 C4 C5 123.1(2)
N3 C4 C9 130.0(2)
C5 C4 C9 106.9(2)
N7 C5 C4 108.7(2)
N7 C5 C6 129.8(2)
C4 C5 C6 121.6(2)
O1 C6 N1 121.3(2)
O1 C6 C5 127.3(2)
N1 C6 C5 111.4(2)
C8 N7 C5 107.34(18)
C8 N7 H7 126.3
C5 N7 H7 126.3
N7 C8 C9 110.4(2)
N7 C8 H8 124.8
C9 C8 H8 124.8
C8 C9 C4 106.7(2)
C8 C9 H9 126.7
C4 C9 H9 126.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.358(3)
N1 C6 1.375(3)
N1 H1 0.8800
O1 C6 1.253(3)
C2 N3 1.306(3)
C2 H2 0.9500
N3 C4 1.383(3)
C4 C5 1.396(3)
C4 C9 1.410(3)
C5 N7 1.376(3)
C5 C6 1.422(3)
N7 C8 1.367(3)
N7 H7 0.8800
C8 C9 1.370(3)
C8 H8 0.9500
C9 H9 0.9500
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 H1 O1 3_756 0.88 1.92 2.799(3) 175
N7 H7 N3 1_556 0.88 2.09 2.965(3) 176
C2 H2 O1 1_554 0.95 2.18 3.106(3) 165
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 393636
2 PubChem 135488881
