#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:32:51 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179667 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/20/4512069.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_4512069
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 H16 F6 N8 O10 S4 Zn'
_chemical_formula_weight         739.94
_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                 98.048(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.2567(4)
_cell_length_b                   9.1981(4)
_cell_length_c                   11.9933(4)
_cell_measurement_reflns_used    2435
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.0600
_cell_measurement_theta_min      3.6210
_cell_volume                     1338.79(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5058
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4670
_diffrn_reflns_theta_full        63.68
_diffrn_reflns_theta_max         63.68
_diffrn_reflns_theta_min         3.64
_exptl_absorpt_coefficient_mu    5.180
_exptl_absorpt_correction_T_max  0.7817
_exptl_absorpt_correction_T_min  0.6254
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0476
_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)+(0.0754P)²+1.3913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1356
_reflns_number_gt                1858
_reflns_number_total             2154
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5005819_si_002.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               4512069
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 0.64812(8) 0.7500 0.0510(3) Uani 1 2 d S . .
S1 S 0.41586(7) 0.64831(13) 0.53385(8) 0.0552(3) Uani 1 1 d . . .
N2 N 0.0644(2) 0.6663(3) 0.6183(3) 0.0445(7) Uani 1 1 d . . .
N3 N 0.1606(2) 0.6615(3) 0.8116(2) 0.0419(7) Uani 1 1 d . . .
H3N H 0.1060 0.6645 0.8494 0.050 Uiso 1 1 calc R . .
N1 N 0.1944(2) 0.6654(3) 0.4892(2) 0.0431(7) Uani 1 1 d . . .
H1N H 0.2022 0.6689 0.4191 0.052 Uiso 1 1 calc R . .
O4 O 0.5000 0.4202(5) 0.7500 0.0588(10) Uani 1 2 d S . .
H4O H 0.4416 0.3904 0.7159 0.088 Uiso 1 1 calc R . .
C3 C 0.1552(3) 0.6617(4) 0.6974(3) 0.0377(7) Uani 1 1 d . . .
C2 C 0.0904(3) 0.6680(4) 0.5157(3) 0.0460(9) Uani 1 1 d . . .
H2 H 0.0328 0.6713 0.4564 0.055 Uiso 1 1 calc R . .
O5 O 0.5000 0.8768(6) 0.7500 0.0959(17) Uani 1 2 d SD . .
H5O H 0.4936 0.9065 0.8132 0.144 Uiso 1 1 calc RD . .
C1 C 0.2882(3) 0.6575(4) 0.5664(3) 0.0397(8) Uani 1 1 d . . .
C6 C 0.1659(5) 0.0757(7) 0.6566(5) 0.1021(19) Uani 1 1 d D . .
N4 N 0.3331(2) 0.6513(3) 0.7755(2) 0.0418(7) Uani 1 1 d . . .
C4 C 0.2619(3) 0.6562(4) 0.6764(3) 0.0377(8) Uani 1 1 d . . .
C5 C 0.2694(3) 0.6556(4) 0.8541(3) 0.0452(8) Uani 1 1 d . . .
H5 H 0.2956 0.6547 0.9308 0.054 Uiso 1 1 calc R . .
S2 S 0.2200(5) 0.2603(8) 0.6550(6) 0.0460(12) Uani 0.53(2) 1 d PDU A 1
O1 O 0.1569(11) 0.3312(17) 0.5655(13) 0.059(4) Uani 0.53(2) 1 d PDU A 1
O2 O 0.3303(5) 0.2523(11) 0.6382(11) 0.079(4) Uani 0.53(2) 1 d PDU A 1
O3 O 0.2024(19) 0.3045(16) 0.7619(8) 0.112(5) Uani 0.53(2) 1 d PDU A 1
S2' S 0.1910(11) 0.2612(10) 0.6788(9) 0.061(2) Uani 0.47(2) 1 d P A 2
O1' O 0.1675(19) 0.314(3) 0.5661(14) 0.092(7) Uani 0.47(2) 1 d P A 2
O2' O 0.306(2) 0.257(2) 0.727(3) 0.209(18) Uani 0.47(2) 1 d P A 2
O3' O 0.118(3) 0.3161(16) 0.7483(14) 0.143(10) Uani 0.47(2) 1 d P A 2
F1 F 0.2028(6) 0.0053(6) 0.5793(7) 0.218(4) Uani 1 1 d D A .
F2 F 0.0609(4) 0.0607(5) 0.6346(6) 0.164(2) Uani 1 1 d D A .
F3 F 0.1961(7) 0.0023(6) 0.7473(6) 0.237(4) Uani 1 1 d D A .
O6 O 0.4972(19) 0.072(2) 0.8881(15) 0.183(9) Uani 0.45(2) 1 d PU B 1
O6' O 0.4025(16) 0.0050(19) 0.9121(14) 0.200(9) Uani 0.55(2) 1 d PU B 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'
F F 0.0727 0.0534 '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'
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 O5 180.000(2) . .
O4 Zn1 N4 90.79(8) . .
O5 Zn1 N4 89.21(8) . .
O4 Zn1 N4 90.79(8) . 2_656
O5 Zn1 N4 89.21(8) . 2_656
N4 Zn1 N4 178.41(17) . 2_656
O4 Zn1 S1 90.04(3) . 2_656
O5 Zn1 S1 89.96(3) . 2_656
N4 Zn1 S1 96.34(8) . 2_656
N4 Zn1 S1 83.66(8) 2_656 2_656
O4 Zn1 S1 90.04(3) . .
O5 Zn1 S1 89.96(3) . .
N4 Zn1 S1 83.66(8) . .
N4 Zn1 S1 96.34(8) 2_656 .
S1 Zn1 S1 179.93(6) 2_656 .
C1 S1 Zn1 91.18(12) . .
C2 N2 C3 111.8(3) . .
C5 N3 C3 106.5(3) . .
C5 N3 H3N 126.7 . .
C3 N3 H3N 126.7 . .
C2 N1 C1 124.7(3) . .
C2 N1 H1N 117.7 . .
C1 N1 H1N 117.7 . .
Zn1 O4 H4O 109.5 . .
N2 C3 N3 128.4(3) . .
N2 C3 C4 125.8(3) . .
N3 C3 C4 105.8(3) . .
N2 C2 N1 125.4(3) . .
N2 C2 H2 117.3 . .
N1 C2 H2 117.3 . .
Zn1 O5 H5O 109.5 . .
N1 C1 C4 110.7(3) . .
N1 C1 S1 124.7(3) . .
C4 C1 S1 124.5(3) . .
F1 C6 F2 104.2(6) . .
F1 C6 F3 105.1(7) . .
F2 C6 F3 106.2(7) . .
F1 C6 S2' 122.5(7) . .
F2 C6 S2' 106.6(6) . .
F3 C6 S2' 111.1(5) . .
F1 C6 S2 107.5(5) . .
F2 C6 S2 116.9(5) . .
F3 C6 S2 115.7(5) . .
S2' C6 S2 15.4(4) . .
C5 N4 C4 104.7(3) . .
C5 N4 Zn1 142.6(2) . .
C4 N4 Zn1 112.7(2) . .
C3 C4 N4 110.4(3) . .
C3 C4 C1 121.7(3) . .
N4 C4 C1 127.9(3) . .
N4 C5 N3 112.6(3) . .
N4 C5 H5 123.7 . .
N3 C5 H5 123.7 . .
O3 S2 O1 115.6(12) . .
O3 S2 O2 115.3(8) . .
O1 S2 O2 110.9(8) . .
O3 S2 C6 99.2(7) . .
O1 S2 C6 106.3(7) . .
O2 S2 C6 108.3(6) . .
O3' S2' O1' 112.2(12) . .
O3' S2' O2' 116.1(15) . .
O1' S2' O2' 116.2(14) . .
O3' S2' C6 109.2(8) . .
O1' S2' C6 100.6(12) . .
O2' S2' C6 100.3(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O4 2.097(4) .
Zn1 O5 2.103(5) .
Zn1 N4 2.111(3) .
Zn1 N4 2.111(3) 2_656
Zn1 S1 2.6524(10) 2_656
Zn1 S1 2.6524(10) .
S1 C1 1.667(3) .
N2 C2 1.314(5) .
N2 C3 1.359(4) .
N3 C5 1.361(5) .
N3 C3 1.362(5) .
N3 H3N 0.8600 .
N1 C2 1.357(5) .
N1 C1 1.372(4) .
N1 H1N 0.8600 .
O4 H4O 0.8200 .
C3 C4 1.367(5) .
C2 H2 0.9300 .
O5 H5O 0.8200 .
C1 C4 1.401(5) .
C6 F1 1.265(6) .
C6 F2 1.285(6) .
C6 F3 1.290(6) .
C6 S2' 1.747(11) .
C6 S2 1.824(10) .
N4 C5 1.306(5) .
N4 C4 1.374(4) .
C5 H5 0.9300 .
S2 O3 1.390(9) .
S2 O1 1.394(10) .
S2 O2 1.397(8) .
S2' O3' 1.403(16) .
S2' O1' 1.428(14) .
S2' O2' 1.444(15) .
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
O5 H5O O6 0.82 1.76 2.445(17) 139.4 1_565
O4 H4O O2 0.82 2.00 2.779(8) 159.5 .
N3 H3N N2 0.86 2.18 2.994(4) 158.6 2_556
N1 H1N O3 0.86 1.90 2.756(10) 171.9 4_565
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 92.90(12) .
O5 Zn1 S1 C1 -87.10(12) .
N4 Zn1 S1 C1 2.11(14) .
N4 Zn1 S1 C1 -176.29(15) 2_656
S1 Zn1 S1 C1 -87(60) 2_656
C2 N2 C3 N3 178.7(3) .
C2 N2 C3 C4 -1.4(5) .
C5 N3 C3 N2 179.8(3) .
C5 N3 C3 C4 -0.1(4) .
C3 N2 C2 N1 0.1(5) .
C1 N1 C2 N2 1.4(6) .
C2 N1 C1 C4 -1.5(5) .
C2 N1 C1 S1 177.7(3) .
Zn1 S1 C1 N1 178.3(3) .
Zn1 S1 C1 C4 -2.6(3) .
O4 Zn1 N4 C5 91.8(4) .
O5 Zn1 N4 C5 -88.2(4) .
N4 Zn1 N4 C5 -88.2(4) 2_656
S1 Zn1 N4 C5 1.7(4) 2_656
S1 Zn1 N4 C5 -178.2(4) .
O4 Zn1 N4 C4 -91.7(2) .
O5 Zn1 N4 C4 88.3(2) .
N4 Zn1 N4 C4 88.3(2) 2_656
S1 Zn1 N4 C4 178.2(2) 2_656
S1 Zn1 N4 C4 -1.7(2) .
N2 C3 C4 N4 -179.5(3) .
N3 C3 C4 N4 0.5(4) .
N2 C3 C4 C1 1.2(5) .
N3 C3 C4 C1 -178.8(3) .
C5 N4 C4 C3 -0.7(4) .
Zn1 N4 C4 C3 -178.5(2) .
C5 N4 C4 C1 178.5(3) .
Zn1 N4 C4 C1 0.7(5) .
N1 C1 C4 C3 0.2(5) .
S1 C1 C4 C3 -178.9(3) .
N1 C1 C4 N4 -178.9(3) .
S1 C1 C4 N4 1.9(5) .
C4 N4 C5 N3 0.6(4) .
Zn1 N4 C5 N3 177.3(3) .
C3 N3 C5 N4 -0.3(4) .
F1 C6 S2 O3 -162.0(11) .
F2 C6 S2 O3 81.4(11) .
F3 C6 S2 O3 -44.9(11) .
S2' C6 S2 O3 30.8(17) .
F1 C6 S2 O1 77.8(11) .
F2 C6 S2 O1 -38.8(12) .
F3 C6 S2 O1 -165.1(11) .
S2' C6 S2 O1 -89.4(18) .
F1 C6 S2 O2 -41.4(8) .
F2 C6 S2 O2 -158.0(8) .
F3 C6 S2 O2 75.7(9) .
S2' C6 S2 O2 151(2) .
F1 C6 S2' O3' 164.6(15) .
F2 C6 S2' O3' 45.1(15) .
F3 C6 S2' O3' -70.2(13) .
S2 C6 S2' O3' 179(2) .
F1 C6 S2' O1' 46.4(16) .
F2 C6 S2' O1' -73.1(15) .
F3 C6 S2' O1' 171.6(13) .
S2 C6 S2' O1' 61(2) .
F1 C6 S2' O2' -72.9(17) .
F2 C6 S2' O2' 167.6(16) .
F3 C6 S2' O2' 52.3(16) .
S2 C6 S2' O2' -58(2) .
