#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:56:56 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179605 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/69/4506911.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4506911
loop_
_publ_author_name
'Xu, Lin-Lin'
'Chen, Jia-Mei'
'Yan, Yan'
'Lu, Tong-Bu'
_publ_section_title
;
 Improving the Solubility of 6-Mercaptopurine via Cocrystals and Salts
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              6004
_journal_paper_doi               10.1021/cg3010745
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C12 H10 N4 O3 S'
_chemical_formula_weight         290.30
_chemical_name_systematic
; 
 ? 
;
_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                 90.292(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3806(8)
_cell_length_b                   8.0655(6)
_cell_length_c                   12.5124(8)
_cell_measurement_reflns_used    2831
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.1248
_cell_measurement_theta_min      3.5295
_cell_volume                     1249.42(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5058
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6886
_diffrn_reflns_theta_full        65.22
_diffrn_reflns_theta_max         65.22
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    2.452
_exptl_absorpt_correction_T_max  0.8872
_exptl_absorpt_correction_T_min  0.7916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.182
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2084
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0602
_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)+(0.0674P)²+2.3996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1566
_reflns_number_gt                1789
_reflns_number_total             2084
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3010745_si_002.cif
_cod_data_source_block           111205_111129_22_8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4506911
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.22364(7) 0.04227(13) 0.68457(8) 0.0465(3) Uani 1 1 d U
N3 N 0.0464(2) 0.1986(4) 0.3732(2) 0.0409(7) Uani 1 1 d .
N4 N 0.1830(2) 0.0557(4) 0.4674(3) 0.0429(8) Uani 1 1 d U
N2 N -0.0778(2) 0.3266(4) 0.4970(2) 0.0445(8) Uani 1 1 d .
N1 N -0.0008(3) 0.2557(5) 0.6523(3) 0.0512(9) Uani 1 1 d U
C5 C 0.1342(3) 0.1049(5) 0.3772(4) 0.0467(10) Uani 1 1 d .
H5A H 0.1647 0.0702 0.3114 0.056 Uiso 1 1 calc R
C4 C 0.0125(3) 0.2362(4) 0.4737(3) 0.0375(8) Uani 1 1 d U
C3 C -0.0815(3) 0.3340(5) 0.6027(3) 0.0514(10) Uani 1 1 d U
H3AA H -0.1371 0.3904 0.6400 0.062 Uiso 1 1 calc R
C1 C 0.1525(3) 0.0988(5) 0.5752(3) 0.0505(10) Uani 1 1 d U
C2 C 0.0601(3) 0.1912(5) 0.5706(3) 0.0489(9) Uani 1 1 d U
H1A H 0.018(4) 0.244(6) 0.716(4) 0.066(15) Uiso 1 1 d .
H4A H 0.241(4) -0.019(7) 0.464(4) 0.082(16) Uiso 1 1 d .
O3 O -0.2258(2) 0.4298(4) 0.3444(2) 0.0473(7) Uani 1 1 d .
O1 O -0.64982(19) 0.8459(3) 0.43373(19) 0.0429(6) Uani 1 1 d .
C8 C -0.3960(3) 0.6730(4) 0.5249(3) 0.0365(8) Uani 1 1 d .
H8A H -0.3977 0.7100 0.5969 0.044 Uiso 1 1 calc R
O2 O -0.5649(2) 0.8660(3) 0.5918(2) 0.0437(7) Uani 1 1 d .
C11 C -0.3925(3) 0.5635(5) 0.3140(3) 0.0399(8) Uani 1 1 d .
H11A H -0.3916 0.5252 0.2422 0.048 Uiso 1 1 calc R
C9 C -0.3105(3) 0.5774(4) 0.4893(3) 0.0380(8) Uani 1 1 d .
H9A H -0.2533 0.5492 0.5369 0.046 Uiso 1 1 calc R
C7 C -0.4795(3) 0.7151(4) 0.4550(3) 0.0344(8) Uani 1 1 d .
C6 C -0.5725(3) 0.8139(4) 0.4909(3) 0.0366(8) Uani 1 1 d .
C12 C -0.4768(3) 0.6598(4) 0.3498(3) 0.0382(8) Uani 1 1 d .
H12A H -0.5337 0.6887 0.3022 0.046 Uiso 1 1 calc R
C10 C -0.3083(3) 0.5226(4) 0.3839(3) 0.0380(8) Uani 1 1 d .
H3A H -0.179(3) 0.411(4) 0.391(3) 0.028(10) Uiso 1 1 d .
H2A H -0.622(3) 0.914(5) 0.607(3) 0.046(12) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C5 N3 C4 110.4(3)
C5 N4 C1 126.7(3)
C5 N4 H4A 120(3)
C1 N4 H4A 114(3)
C3 N2 C4 105.6(3)
C3 N1 C2 104.1(4)
C3 N1 H1A 134(3)
C2 N1 H1A 121(3)
N3 C5 N4 124.6(4)
N3 C5 H5A 117.7
N4 C5 H5A 117.7
N3 C4 N2 124.9(3)
N3 C4 C2 127.9(3)
N2 C4 C2 107.2(3)
N2 C3 N1 114.5(4)
N2 C3 H3AA 122.8
N1 C3 H3AA 122.8
C2 C1 N4 108.3(3)
C2 C1 S1 128.0(4)
N4 C1 S1 123.7(3)
C1 C2 N1 129.5(4)
C1 C2 C4 122.0(4)
N1 C2 C4 108.5(4)
C10 O3 H3A 112(2)
C9 C8 C7 120.0(3)
C9 C8 H8A 120.0
C7 C8 H8A 120.0
C6 O2 H2A 108(3)
C12 C11 C10 119.6(3)
C12 C11 H11A 120.2
C10 C11 H11A 120.2
C8 C9 C10 119.9(3)
C8 C9 H9A 120.0
C10 C9 H9A 120.0
C12 C7 C8 119.7(3)
C12 C7 C6 119.0(3)
C8 C7 C6 121.3(3)
O1 C6 O2 122.7(3)
O1 C6 C7 123.3(3)
O2 C6 C7 114.1(3)
C11 C12 C7 120.7(3)
C11 C12 H12A 119.7
C7 C12 H12A 119.7
O3 C10 C9 122.5(3)
O3 C10 C11 117.4(3)
C9 C10 C11 120.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.686(4)
N3 C5 1.325(5)
N3 C4 1.362(4)
N4 C5 1.337(5)
N4 C1 1.445(5)
N4 H4A 0.94(5)
N2 C3 1.324(5)
N2 C4 1.367(5)
N1 C3 1.333(6)
N1 C2 1.376(5)
N1 H1A 0.84(5)
C5 H5A 0.9500
C4 C2 1.393(5)
C3 H3AA 0.9500
C1 C2 1.367(6)
O3 C10 1.362(4)
O3 H3A 0.83(4)
O1 C6 1.219(4)
C8 C9 1.386(5)
C8 C7 1.392(5)
C8 H8A 0.9500
O2 C6 1.334(4)
O2 H2A 0.83(4)
C11 C12 1.379(5)
C11 C10 1.396(5)
C11 H11A 0.9500
C9 C10 1.391(5)
C9 H9A 0.9500
C7 C12 1.390(5)
C7 C6 1.473(5)
C12 H12A 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N3 0.84(5) 2.04(5) 2.846(5) 160(5) 4_566
N4 H4A O1 0.94(5) 1.78(6) 2.708(4) 170(5) 1_645
O2 H2A S1 0.83(4) 2.38(4) 3.202(3) 169(4) 1_465
O3 H3A N2 0.83(4) 1.95(4) 2.768(4) 170(4) .
