#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/15/2221519.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_2221519
loop_
_publ_author_name
'Liu, Zhengyu'
'Liu, Kevin K.-C.'
'Elleraas, Jeff'
'Rheingold, Arnold L.'
'DiPasquale, Antonio'
'Yanovsky, Alex'
_publ_section_title
(R)-4-[2-(Methylsulfanyl)pyrimidin-4-yl]-1-(tetrahydrofuran-3-yl)-1H-pyrazol-5-amine
_journal_coeditor_code           TK2382
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o697
_journal_paper_doi               10.1107/S160053680900734X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H15 N5 O S'
_chemical_formula_moiety         'C12 H15 N5 O S'
_chemical_formula_sum            'C12 H15 N5 O S'
_chemical_formula_weight         277.35
_chemical_name_common            110649-0398-004
_chemical_name_systematic
;
(R)-4-[2-(Methylsulfanyl)pyrimidin-4-yl]-1-(tetrahydrofuran-3-yl)-
1H-pyrazol-5-amine
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.479(2)
_cell_length_b                   7.1217(10)
_cell_length_c                   11.7802(17)
_cell_measurement_reflns_used    5004
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      2.6
_cell_volume                     1298.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-32 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      208(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker D8 APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.043
_diffrn_reflns_av_sigmaI/netI    0.046
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6570
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         28.1
_diffrn_reflns_theta_min         1.7
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.25
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.35
_refine_ls_abs_structure_details 'Flack (1983), 1180 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_coef       0.058(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_gt           0.041
_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)+(0.0703P)²+0.0815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.112
_refine_ls_wR_factor_ref         0.115
_reflns_number_gt                2844
_reflns_number_total             3025
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2382.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2221519
_cod_database_fobs_code          2221519
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
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
C C1 0.61092(15) 0.3862(4) 1.04598(18) 0.0592(6) Uani d . 1 . .
H H1A 0.6660 0.3550 1.0825 0.071 Uiso calc R 1 . .
H H1B 0.5758 0.4600 1.0989 0.071 Uiso calc R 1 . .
C C2 0.62567(13) 0.4931(3) 0.93597(14) 0.0471(4) Uani d . 1 . .
H H2A 0.6760 0.5761 0.9418 0.057 Uiso calc R 1 . .
H H2B 0.5748 0.5677 0.9154 0.057 Uiso calc R 1 . .
C C3 0.64143(10) 0.3354(3) 0.85008(15) 0.0414(4) Uani d . 1 . .
H H3 0.6054 0.3562 0.7818 0.050 Uiso calc R 1 . .
C C4 0.61086(12) 0.1571(3) 0.91240(18) 0.0514(5) Uani d . 1 . .
H H4A 0.5721 0.0835 0.8639 0.062 Uiso calc R 1 . .
H H4B 0.6603 0.0785 0.9334 0.062 Uiso calc R 1 . .
C C5 0.86860(11) 0.3275(3) 0.84766(15) 0.0456(4) Uani d . 1 . .
H H5 0.9228 0.3341 0.8835 0.055 Uiso calc R 1 . .
C C6 0.85782(9) 0.3006(3) 0.72974(14) 0.0355(4) Uani d . 1 . .
C C7 0.76781(9) 0.3006(2) 0.71461(13) 0.0341(3) Uani d . 1 . .
C C8 0.92276(9) 0.2767(2) 0.64376(13) 0.0341(3) Uani d . 1 . .
C C9 1.01122(10) 0.2623(3) 0.66996(14) 0.0427(4) Uani d . 1 . .
H H9 1.0308 0.2671 0.7454 0.051 Uiso calc R 1 . .
C C10 1.06733(10) 0.2412(3) 0.58192(16) 0.0466(4) Uani d . 1 . .
H H10 1.1264 0.2289 0.5987 0.056 Uiso calc R 1 . .
C C11 0.95801(10) 0.2531(3) 0.45560(14) 0.0371(3) Uani d . 1 . .
C C12 0.81445(13) 0.2818(3) 0.31648(16) 0.0526(5) Uani d . 1 . .
H H12A 0.7888 0.1785 0.3583 0.079 Uiso calc R 1 . .
H H12B 0.7917 0.2833 0.2398 0.079 Uiso calc R 1 . .
H H12C 0.8006 0.3993 0.3539 0.079 Uiso calc R 1 . .
N N1 0.73257(8) 0.3241(2) 0.81741(12) 0.0393(3) Uani d . 1 . .
N N2 0.79452(9) 0.3423(3) 0.90197(12) 0.0488(4) Uani d . 1 . .
N N3 0.72268(9) 0.2815(3) 0.61696(12) 0.0493(4) Uani d . 1 . .
H H3A 0.6665 0.2841 0.6182 0.059 Uiso calc R 1 . .
H H3B 0.7498 0.2667 0.5529 0.059 Uiso calc R 1 . .
N N4 1.04322(9) 0.2367(3) 0.47231(13) 0.0453(4) Uani d . 1 . .
N N5 0.89635(8) 0.2704(2) 0.53396(11) 0.0341(3) Uani d . 1 . .
O O1 0.56646(9) 0.2206(3) 1.01145(14) 0.0630(5) Uani d . 1 . .
S S1 0.92940(3) 0.25258(9) 0.31179(4) 0.05191(18) Uani 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'
S S 0.1246 0.1234 '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
O1 C1 C2 . . 104.11(19) ?
O1 C1 H1A . . 110.9 ?
C2 C1 H1A . . 110.9 ?
O1 C1 H1B . . 110.9 ?
C2 C1 H1B . . 110.9 ?
H1A C1 H1B . . 109.0 ?
C1 C2 C3 . . 102.70(18) ?
C1 C2 H2A . . 111.2 ?
C3 C2 H2A . . 111.2 ?
C1 C2 H2B . . 111.2 ?
C3 C2 H2B . . 111.2 ?
H2A C2 H2B . . 109.1 ?
N1 C3 C2 . . 111.55(15) ?
N1 C3 C4 . . 112.07(16) ?
C2 C3 C4 . . 103.93(14) ?
N1 C3 H3 . . 109.7 ?
C2 C3 H3 . . 109.7 ?
C4 C3 H3 . . 109.7 ?
O1 C4 C3 . . 106.03(18) ?
O1 C4 H4A . . 110.5 ?
C3 C4 H4A . . 110.5 ?
O1 C4 H4B . . 110.5 ?
C3 C4 H4B . . 110.5 ?
H4A C4 H4B . . 108.7 ?
N2 C5 C6 . . 112.69(15) ?
N2 C5 H5 . . 123.7 ?
C6 C5 H5 . . 123.7 ?
C7 C6 C5 . . 104.00(14) ?
C7 C6 C8 . . 127.19(14) ?
C5 C6 C8 . . 128.81(14) ?
N1 C7 N3 . . 124.85(14) ?
N1 C7 C6 . . 106.83(13) ?
N3 C7 C6 . . 128.32(15) ?
N5 C8 C9 . . 119.98(14) ?
N5 C8 C6 . . 117.70(13) ?
C9 C8 C6 . . 122.32(14) ?
C10 C9 C8 . . 117.50(15) ?
C10 C9 H9 . . 121.2 ?
C8 C9 H9 . . 121.2 ?
N4 C10 C9 . . 123.87(14) ?
N4 C10 H10 . . 118.1 ?
C9 C10 H10 . . 118.1 ?
N5 C11 N4 . . 127.69(15) ?
N5 C11 S1 . . 119.28(12) ?
N4 C11 S1 . . 113.03(12) ?
S1 C12 H12A . . 109.5 ?
S1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
S1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C7 N1 N2 . . 112.28(13) ?
C7 N1 C3 . . 129.58(14) ?
N2 N1 C3 . . 118.13(13) ?
C5 N2 N1 . . 104.20(14) ?
C7 N3 H3A . . 120.0 ?
C7 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
C11 N4 C10 . . 114.37(14) ?
C11 N5 C8 . . 116.57(13) ?
C1 O1 C4 . . 105.25(15) ?
C11 S1 C12 . . 102.76(8) ?
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
C1 O1 . 1.425(3) ?
C1 C2 . 1.520(3) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C2 C3 . 1.531(3) ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C3 N1 . 1.4644(18) ?
C3 C4 . 1.541(3) ?
C3 H3 . 0.9900 ?
C4 O1 . 1.428(3) ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C5 N2 . 1.317(2) ?
C5 C6 . 1.412(2) ?
C5 H5 . 0.9400 ?
C6 C7 . 1.4046(19) ?
C6 C8 . 1.437(2) ?
C7 N1 . 1.339(2) ?
C7 N3 . 1.353(2) ?
C8 N5 . 1.357(2) ?
C8 C9 . 1.407(2) ?
C9 C10 . 1.361(2) ?
C9 H9 . 0.9400 ?
C10 N4 . 1.344(2) ?
C10 H10 . 0.9400 ?
C11 N5 . 1.3334(19) ?
C11 N4 . 1.339(2) ?
C11 S1 . 1.7510(17) ?
C12 S1 . 1.792(2) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C12 H12C . 0.9700 ?
N1 N2 . 1.3888(18) ?
N3 H3A . 0.8700 ?
N3 H3B . 0.8700 ?
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
N3 H3A N4 3_456 0.87 2.19 2.9731(19) 149.5
N3 H3B N5 . 0.87 2.28 2.8616(19) 124.4
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741866
