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#$Date: 2016-03-24 14:32:51 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179667 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/20/4512071.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_4512071
loop_
_publ_author_name
'Yao, Jia'
'Chen, Jia-Mei'
'Xu, Yi-Bo'
'Lu, Tong-Bu'
_publ_section_title
;
 Enhancing the Solubility of 6-Mercaptopurine by Formation of Ionic
 Cocrystal with Zinc Trifluoromethanesulfonate:
 Single-Crystal-to-Single-Crystal Transformation
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5019
_journal_paper_doi               10.1021/cg5005819
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C12 H10 F6 N8 O7 S4 Zn'
_chemical_formula_weight         685.89
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/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                 96.781(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.1058(5)
_cell_length_b                   9.1233(7)
_cell_length_c                   11.9600(5)
_cell_measurement_reflns_used    1543
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      60.9770
_cell_measurement_theta_min      3.6960
_cell_volume                     1311.68(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 10.5058
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4607
_diffrn_reflns_theta_full        63.52
_diffrn_reflns_theta_max         63.52
_diffrn_reflns_theta_min         3.68
_exptl_absorpt_coefficient_mu    5.147
_exptl_absorpt_correction_T_max  0.7829
_exptl_absorpt_correction_T_min  0.4259
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.609
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.128
_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     210
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0779
_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)+(0.1649P)²+0.8246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2198
_refine_ls_wR_factor_ref         0.2439
_reflns_number_gt                1582
_reflns_number_total             2081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5005819_si_004.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               4512071
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.5000 0.62509(16) 0.7500 0.0676(6) Uani 1 2 d S . .
S1 S 0.42769(12) 0.6662(3) 0.53998(12) 0.0777(7) Uani 1 1 d . . .
N1 N 0.2036(4) 0.6784(6) 0.4909(4) 0.0581(13) Uani 1 1 d . . .
H1 H 0.2131 0.6820 0.4208 0.070 Uiso 1 1 calc R . .
O4 O 0.5000 0.4072(9) 0.7500 0.082(2) Uani 1 2 d S . .
H4 H 0.4410 0.3772 0.7172 0.123 Uiso 1 1 calc R . .
N2 N 0.0684(4) 0.6800(6) 0.6189(4) 0.0584(13) Uani 1 1 d . . .
C2 C 0.0995(5) 0.6795(8) 0.5170(5) 0.0622(16) Uani 1 1 d . . .
H2 H 0.0431 0.6800 0.4571 0.075 Uiso 1 1 calc R . .
C1 C 0.2967(5) 0.6720(7) 0.5685(5) 0.0566(14) Uani 1 1 d . . .
N4 N 0.3359(4) 0.6649(6) 0.7759(3) 0.0563(13) Uani 1 1 d . . .
C3 C 0.1581(5) 0.6743(7) 0.6988(4) 0.0523(13) Uani 1 1 d . . .
N3 N 0.1619(4) 0.6719(6) 0.8130(4) 0.0581(13) Uani 1 1 d . . .
H3 H 0.1058 0.6732 0.8510 0.070 Uiso 1 1 calc R . .
C4 C 0.2664(5) 0.6709(7) 0.6780(4) 0.0520(14) Uani 1 1 d . . .
C5 C 0.2699(5) 0.6670(8) 0.8554(4) 0.0585(16) Uani 1 1 d . . .
H5 H 0.2948 0.6654 0.9320 0.070 Uiso 1 1 calc R . .
C6 C 0.1954(16) 0.915(2) 0.1648(11) 0.153(5) Uani 1 1 d . . .
F1 F 0.2286(15) 0.9827(10) 0.2492(11) 0.272(8) Uani 1 1 d . A .
F2 F 0.2133(14) 0.9816(11) 0.0793(12) 0.257(7) Uani 1 1 d . A .
F3 F 0.0830(13) 0.9458(12) 0.1550(14) 0.257(7) Uani 1 1 d . A .
S2 S 0.2180(5) 0.7284(4) 0.1557(4) 0.0633(11) Uani 0.700(12) 1 d P A 1
O1 O 0.3314(6) 0.7227(12) 0.1323(7) 0.101(3) Uani 0.700(12) 1 d P A 1
O2 O 0.2042(15) 0.6741(12) 0.2622(7) 0.113(5) Uani 0.700(12) 1 d P A 1
O3 O 0.1479(16) 0.677(3) 0.0632(16) 0.086(6) Uani 0.700(12) 1 d P A 1
S2' S 0.1758(8) 0.7206(8) 0.1860(7) 0.050(2) Uani 0.300(12) 1 d PU A 2
O1' O 0.2781(19) 0.693(3) 0.261(2) 0.098(9) Uani 0.300(12) 1 d P A 2
O2' O 0.0731(12) 0.709(3) 0.2310(12) 0.095(8) Uani 0.300(12) 1 d P A 2
O3' O 0.175(4) 0.656(6) 0.076(3) 0.089(14) Uani 0.300(12) 1 d PU A 2
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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O4 Zn1 N4 100.05(16) . .
O4 Zn1 N4 100.05(16) . 2_656
N4 Zn1 N4 159.9(3) . 2_656
O4 Zn1 S1 98.34(6) . 2_656
N4 Zn1 S1 92.85(12) . 2_656
N4 Zn1 S1 84.24(12) 2_656 2_656
O4 Zn1 S1 98.34(6) . .
N4 Zn1 S1 84.24(12) . .
N4 Zn1 S1 92.85(12) 2_656 .
S1 Zn1 S1 163.32(12) 2_656 .
C1 S1 Zn1 91.56(19) . .
C2 N1 C1 124.4(5) . .
C2 N1 H1 117.8 . .
C1 N1 H1 117.8 . .
Zn1 O4 H4 109.5 . .
C2 N2 C3 111.0(5) . .
N2 C2 N1 126.7(5) . .
N2 C2 H2 116.7 . .
N1 C2 H2 116.7 . .
N1 C1 C4 110.3(5) . .
N1 C1 S1 126.1(4) . .
C4 C1 S1 123.5(4) . .
C5 N4 C4 104.9(4) . .
C5 N4 Zn1 141.7(4) . .
C4 N4 Zn1 112.5(3) . .
N2 C3 N3 129.4(5) . .
N2 C3 C4 125.3(5) . .
N3 C3 C4 105.3(5) . .
C5 N3 C3 107.2(4) . .
C5 N3 H3 126.4 . .
C3 N3 H3 126.4 . .
N4 C4 C3 110.7(4) . .
N4 C4 C1 127.0(5) . .
C3 C4 C1 122.2(5) . .
N4 C5 N3 112.0(4) . .
N4 C5 H5 124.0 . .
N3 C5 H5 124.0 . .
F1 C6 F2 111.2(19) . .
F1 C6 F3 101.0(16) . .
F2 C6 F3 95.5(15) . .
F1 C6 S2 121.2(13) . .
F2 C6 S2 113.0(12) . .
F3 C6 S2 111.1(14) . .
F1 C6 S2' 115.0(12) . .
F2 C6 S2' 129.9(13) . .
F3 C6 S2' 94.0(13) . .
S2 C6 S2' 21.5(3) . .
O3 S2 O2 118.5(12) . .
O3 S2 O1 109.9(9) . .
O2 S2 O1 112.7(8) . .
O3 S2 C6 107.3(12) . .
O2 S2 C6 104.8(7) . .
O1 S2 C6 102.2(8) . .
O2' S2' O3' 114(2) . .
O2' S2' O1' 118.2(17) . .
O3' S2' O1' 114(2) . .
O2' S2' C6 105.3(13) . .
O3' S2' C6 105(2) . .
O1' S2' C6 97.9(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O4 1.988(8) .
Zn1 N4 2.079(4) .
Zn1 N4 2.079(4) 2_656
Zn1 S1 2.5879(15) 2_656
Zn1 S1 2.5879(15) .
S1 C1 1.662(6) .
N1 C2 1.334(8) .
N1 C1 1.373(7) .
N1 H1 0.8600 .
O4 H4 0.8200 .
N2 C2 1.318(7) .
N2 C3 1.359(7) .
C2 H2 0.9300 .
C1 C4 1.401(8) .
N4 C5 1.312(7) .
N4 C4 1.360(7) .
C3 N3 1.362(7) .
C3 C4 1.364(8) .
N3 C5 1.346(7) .
N3 H3 0.8600 .
C5 H5 0.9300 .
C6 F1 1.213(16) .
C6 F2 1.234(17) .
C6 F3 1.382(19) .
C6 S2 1.725(19) .
C6 S2' 1.81(2) .
S2 O3 1.39(2) .
S2 O2 1.396(10) .
S2 O1 1.434(10) .
S2' O2' 1.415(19) .
S2' O3' 1.44(3) .
S2' O1' 1.462(19) .
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
N3 H3 N2 0.86 2.18 2.996(7) 157.8 2_556
O4 H4 O1 0.82 1.82 2.622(8) 166.3 4_566
N1 H1 O2 0.86 1.89 2.736(10) 168.2 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
O4 Zn1 S1 C1 91.6(2) .
N4 Zn1 S1 C1 -7.8(3) .
N4 Zn1 S1 C1 -167.8(3) 2_656
S1 Zn1 S1 C1 -88.4(2) 2_656
C3 N2 C2 N1 -2.1(10) .
C1 N1 C2 N2 2.6(11) .
C2 N1 C1 C4 -1.7(9) .
C2 N1 C1 S1 178.4(6) .
Zn1 S1 C1 N1 -173.4(6) .
Zn1 S1 C1 C4 6.6(6) .
O4 Zn1 N4 C5 78.5(8) .
N4 Zn1 N4 C5 -101.5(8) 2_656
S1 Zn1 N4 C5 -20.5(8) 2_656
S1 Zn1 N4 C5 176.0(8) .
O4 Zn1 N4 C4 -88.3(4) .
N4 Zn1 N4 C4 91.7(4) 2_656
S1 Zn1 N4 C4 172.7(4) 2_656
S1 Zn1 N4 C4 9.1(4) .
C2 N2 C3 N3 -179.6(7) .
C2 N2 C3 C4 1.0(9) .
N2 C3 N3 C5 -179.6(7) .
C4 C3 N3 C5 -0.1(7) .
C5 N4 C4 C3 -1.0(7) .
Zn1 N4 C4 C3 170.6(4) .
C5 N4 C4 C1 179.7(7) .
Zn1 N4 C4 C1 -8.7(9) .
N2 C3 C4 N4 -179.8(6) .
N3 C3 C4 N4 0.7(7) .
N2 C3 C4 C1 -0.5(10) .
N3 C3 C4 C1 180.0(6) .
N1 C1 C4 N4 179.9(6) .
S1 C1 C4 N4 -0.2(10) .
N1 C1 C4 C3 0.7(9) .
S1 C1 C4 C3 -179.4(5) .
C4 N4 C5 N3 1.0(8) .
Zn1 N4 C5 N3 -166.5(5) .
C3 N3 C5 N4 -0.6(8) .
F1 C6 S2 O3 165.5(19) .
F2 C6 S2 O3 -59(2) .
F3 C6 S2 O3 47.2(16) .
S2' C6 S2 O3 86.5(12) .
F1 C6 S2 O2 39(2) .
F2 C6 S2 O2 174.5(17) .
F3 C6 S2 O2 -79.5(14) .
S2' C6 S2 O2 -40.2(10) .
F1 C6 S2 O1 -79.0(19) .
F2 C6 S2 O1 56.8(17) .
F3 C6 S2 O1 162.7(11) .
S2' C6 S2 O1 -158.0(9) .
F1 C6 S2' O2' 78.9(19) .
F2 C6 S2' O2' -126(2) .
F3 C6 S2' O2' -25.2(13) .
S2 C6 S2' O2' -168.9(12) .
F1 C6 S2' O3' -161(3) .
F2 C6 S2' O3' -5(3) .
F3 C6 S2' O3' 95(2) .
S2 C6 S2' O3' -49(2) .
F1 C6 S2' O1' -43(2) .
F2 C6 S2' O1' 112(2) .
F3 C6 S2' O1' -147.4(16) .
S2 C6 S2' O1' 68.9(14) .
