#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/43/2214388.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_2214388
loop_
_publ_author_name
'Rui-Qing Yang'
'Yong-Rong Xie'
_publ_section_title
;
 A monoclinic polymorph of hypoxanthine
;
_journal_coeditor_code           SG2177
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3309
_journal_page_last               o3309
_journal_paper_doi               10.1107/S1600536807030164
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C5 H4 N4 O'
_chemical_formula_moiety         'C5 H4 N4 O'
_chemical_formula_sum            'C5 H4 N4 O'
_chemical_formula_weight         136.12
_chemical_name_common
;
hypoxanthine
;
_chemical_name_systematic
;
1,7-dihydro-6H-purin-6-one
;
_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                 107.469(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.6725(19)
_cell_length_b                   17.960(9)
_cell_length_c                   9.010(5)
_cell_measurement_temperature    292(2)
_cell_volume                     566.9(5)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2981
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.482
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.189
_refine_ls_extinction_coef       0.067(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0356
_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)+(0.0758P)²+0.069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1088
_reflns_number_gt                964
_reflns_number_total             1113
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            sg2177.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214388
_cod_database_fobs_code          2214388
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
O O1 0.5544(3) 0.40375(5) 0.51583(12) 0.0469(3) Uani d . 1
N N1 0.1515(3) 0.46886(6) 0.31417(13) 0.0374(3) Uani d . 1
H H1 0.2213 0.5107 0.3658 0.045 Uiso calc R 1
N N2 -0.2451(3) 0.41739(6) 0.08071(13) 0.0388(3) Uani d . 1
N N3 0.2692(3) 0.26683(6) 0.31153(13) 0.0367(3) Uani d . 1
N N4 -0.1664(3) 0.28307(6) 0.08049(13) 0.0377(3) Uani d . 1
H H4 -0.3275 0.2721 -0.0109 0.045 Uiso calc R 1
C C1 0.3174(4) 0.40330(7) 0.38534(16) 0.0339(3) Uani d . 1
C C2 -0.1094(4) 0.47339(8) 0.17154(16) 0.0395(4) Uani d . 1
H H2 -0.2006 0.5216 0.1350 0.047 Uiso calc R 1
C C3 -0.0906(4) 0.35170(7) 0.14506(15) 0.0329(3) Uani d . 1
C C4 0.1784(3) 0.34128(7) 0.28815(14) 0.0317(3) Uani d . 1
C C5 0.0550(4) 0.23473(8) 0.18446(16) 0.0394(4) Uani d . 1
H H5 0.0552 0.1826 0.1670 0.047 Uiso calc R 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
O1 0.0569(7) 0.0343(6) 0.0312(6) -0.0004(4) -0.0145(5) -0.0024(4)
N1 0.0449(7) 0.0273(6) 0.0308(7) 0.0004(4) -0.0026(5) 0.0000(4)
N2 0.0406(6) 0.0380(7) 0.0284(6) 0.0014(5) -0.0038(5) 0.0046(5)
N3 0.0422(6) 0.0294(6) 0.0289(6) 0.0001(4) -0.0039(5) 0.0000(4)
N4 0.0407(6) 0.0380(7) 0.0233(6) -0.0042(4) -0.0075(5) -0.0041(4)
C1 0.0358(6) 0.0322(7) 0.0261(7) -0.0012(5) -0.0023(5) 0.0016(5)
C2 0.0429(7) 0.0355(7) 0.0318(8) 0.0036(5) -0.0013(6) 0.0062(5)
C3 0.0340(6) 0.0348(7) 0.0244(7) -0.0014(5) 0.0004(5) 0.0012(5)
C4 0.0338(7) 0.0299(7) 0.0247(7) -0.0005(5) -0.0014(5) 0.0018(5)
C5 0.0446(8) 0.0320(7) 0.0317(8) -0.0016(5) -0.0035(6) -0.0029(5)
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 C1 125.10(11)
C2 N1 H1 117.4
C1 N1 H1 117.4
C2 N2 C3 111.78(12)
C5 N3 C4 103.81(11)
C5 N4 C3 106.41(11)
C5 N4 H4 126.8
C3 N4 H4 126.8
O1 C1 N1 121.29(11)
O1 C1 C4 127.93(11)
N1 C1 C4 110.78(12)
N2 C2 N1 125.43(13)
N2 C2 H2 117.3
N1 C2 H2 117.3
N4 C3 N2 126.84(12)
N4 C3 C4 105.93(11)
N2 C3 C4 127.22(12)
N3 C4 C3 110.26(11)
N3 C4 C1 130.06(12)
C3 C4 C1 119.69(12)
N3 C5 N4 113.58(13)
N3 C5 H5 123.2
N4 C5 H5 123.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2352(17)
N1 C2 1.3553(18)
N1 C1 1.3908(17)
N1 H1 0.8800
N2 C2 1.2980(18)
N2 C3 1.3612(17)
N3 C5 1.3118(17)
N3 C4 1.3788(18)
N4 C5 1.3546(17)
N4 C3 1.3557(17)
N4 H4 0.8800
C1 C4 1.4141(18)
C2 H2 0.9500
C3 C4 1.3815(19)
C5 H5 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_666 0.88 1.91 2.7846(18) 171.8
N4 H4 N3 4_465 0.88 1.95 2.8208(19) 167.9
C2 H2 N2 3_465 0.95 2.60 3.376(2) 139.4
C5 H5 O1 4_465 0.95 2.48 3.1933(19) 132.1
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 768
