#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:52:38 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/16/2001645.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_2001645
loop_
_publ_author_name
'Singh, P.'
'Pedersen, L. G.'
_publ_section_title
;
 Orthorhombic form of thiopurinol:
 1,5-dihydro-4<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidine-4-thione
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1211
_journal_page_last               1215
_journal_paper_doi               10.1107/S0108270192013453
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C5 H4 N4 S1'
_chemical_formula_sum            'C5 H4 N4 S'
_chemical_formula_weight         152.19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-I 2 2c'
_symmetry_space_group_name_H-M   'I b a m'
_atom_type_scat_source           'IntTabIV Table 2.2B'
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_formula_units_Z            8
_cell_length_a                   14.597(5)
_cell_length_b                   13.153(5)
_cell_length_c                   6.584(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      7.5
_cell_volume                     1264.1(9)
_diffrn_measurement_device       'Siemens R3m/\m'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            616
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        1.5
_diffrn_standards_interval_count 48
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.42
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.60
_exptl_crystal_description       'Thin needle'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.28
_refine_ls_extinction_coef       4E-7(3)
_refine_ls_extinction_method     Zachariasen
_refine_ls_goodness_of_fit_obs   1.40
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     74
_refine_ls_number_reflns         492
_refine_ls_R_factor_obs          0.043
_refine_ls_shift/esd_max         0.04
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(F~o~)+0.001F~o~^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.060
_reflns_number_observed          492
_reflns_number_total             616
_reflns_observed_criterion       I>=2\s(I)
_cod_data_source_file            cr1037.cif
_cod_data_source_block           cr1037_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/[\s^2^(F~o~)+0.001F~o~^2^]'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(F~o~)+0.001F~o~^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1264.0(10)
_cod_original_formula_sum        'C5 H4 N4 S1'
_cod_database_code               2001645
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1) -.1997(2) .7742(2) .0 .0380(10)
C(2) -.1807(3) .8745(3) .0 .0430(10)
N(3) -.0993(2) .9157(2) .0 .0380(10)
C(4) -.0321(2) .8438(3) .0 .0280(10)
C(5) -.0448(2) .7394(3) .0 .0290(10)
C(6) -.1343(2) .6984(3) .0 .0340(10)
S(6) -.16380(10) .57810(10) .0 .0720(10)
C(7) .0451(3) .6987(3) .0 .0360(10)
N(8) .1061(2) .7722(2) .0 .0360(10)
N(9) .0583(2) .8615(3) .0 .0330(10)
H(1) -.261(4) .753(4) .0 .060(13)
H(2) -.227(4) .908(3) .0 .048(13)
H(7) .061(3) .635(4) .0 .039(12)
H(9) .095(4) .923(3) .0 .049(13)
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
C(2) N(1) C(6) 124.4(3) yes
C(6) N(1) H(1) 117.(3) yes
N(1) C(2) H(2) 112.(3) yes
C(2) N(3) C(4) 111.6(3) yes
N(3) C(4) N(9) 126.1(3) yes
C(4) C(5) C(6) 120.1(3) yes
C(6) C(5) C(7) 135.4(4) yes
N(1) C(6) S(6) 121.0(3) yes
C(5) C(7) N(8) 110.5(4) yes
N(8) C(7) H(7) 122.(3) yes
C(4) N(9) N(8) 110.7(3) yes
N(8) N(9) H(9) 116.(3) yes
C(2) N(1) H(1) 119.(3) yes
N(1) C(2) N(3) 126.3(4) yes
N(3) C(2) H(2) 122.(3) yes
N(3) C(4) C(5) 126.3(3) yes
C(5) C(4) N(9) 107.6(3) yes
C(4) C(5) C(7) 104.5(3) yes
N(1) C(6) C(5) 111.4(3) yes
C(5) C(6) S(6) 127.6(3) yes
C(5) C(7) H(7) 127.(3) yes
C(7) N(8) N(9) 106.7(3) yes
C(4) N(9) H(9) 133.(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) C(2) 1.349(5) yes
N(1) H(1) .94(6) yes
C(2) H(2) .81(5) yes
C(4) C(5) 1.386(5) yes
C(5) C(6) 1.414(5) yes
C(6) S(6) 1.640(4) yes
C(7) H(7) .87(5) yes
N(9) H(9) .97(5) yes
N(1) C(6) 1.379(5) yes
C(2) N(3) 1.306(5) yes
N(3) C(4) 1.362(5) yes
C(4) N(9) 1.340(4) yes
C(5) C(7) 1.418(5) yes
C(7) N(8) 1.314(5) yes
N(8) N(9) 1.366(5) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 135445058
