Regiospecific route to N9-alkylated thioxanthines
Savateev, Konstantin V.; Fedotov, Victor V.; Slepukhin, Pavel A.; Ulomsky, Evgeniy N.; Rusinov, Vladimir L.; New Journal of Chemistry 46 (2022) 17145–17148; doi:10.1039/D2NJ03002K

data_7061767
_publ_section_title
;
 Regiospecific route to N9-alkylated thioxanthines
;
_journal_issue                   36
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17145
_journal_page_last               17148
_journal_paper_doi               10.1039/D2NJ03002K
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C18 H22 N8 O2 S2, 2(C2 H6 O S)'
_chemical_formula_sum            'C22 H34 N8 O4 S4'
_chemical_formula_weight         602.81
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-08-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-04-01 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8823(13)
_cell_length_b                   16.0031(17)
_cell_length_c                   16.3570(15)
_cell_measurement_reflns_used    1327
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      21.9050
_cell_measurement_theta_min      4.1650
_cell_volume                     3110.3(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -3.00  26.00   1.00   20.00    --   22.52  91.00  72.00   29
  2  \w      9.00  64.00   1.00   20.00    --   22.52  54.00-151.00   55
  3  \w    -35.00  29.00   1.00   20.00    --  -24.08  81.00 -28.00   64
  4  \w     39.00  76.00   1.00   20.00    --   22.52 178.00-180.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0524538000
_diffrn_orient_matrix_UB_12      -0.0211319000
_diffrn_orient_matrix_UB_13      0.0001213000
_diffrn_orient_matrix_UB_21      -0.0144746000
_diffrn_orient_matrix_UB_22      0.0196492000
_diffrn_orient_matrix_UB_23      -0.0374501000
_diffrn_orient_matrix_UB_31      0.0244569000
_diffrn_orient_matrix_UB_32      -0.0336391000
_diffrn_orient_matrix_UB_33      -0.0219187000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0969
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11768
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.869
_diffrn_reflns_theta_min         3.562
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       prism
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0045(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4251
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.2165
_refine_ls_R_factor_gt           0.0889
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1200P)^2^+0.1200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2253
_refine_ls_wR_factor_ref         0.3188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1507
_reflns_number_total             4251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03002k2.cif
_cod_data_source_block           exp_1046
_cod_depositor_comments
'Adding full bibliography for 7061766--7061768.cif.'
_cod_database_code               7061767
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.852
_reflns_odcompleteness_completeness 98.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C2S-S2
 1.7 with sigma of 0.02
 S2-C1
 1.7 with sigma of 0.02
 S1S-C1S
 1.7 with sigma of 0.02
 C2S-S1S
 1.7 with sigma of 0.02
 O1S-S1S
 1.5 with sigma of 0.02
 S2-O1S
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C1S) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: S1S(0.85) H2SA(0.85) H2SB(0.85) H2SC(0.85) H2SD(0.15) H2SE(0.15)
 H2SF(0.15) C1S(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5) C1(0.5) H1A(0.5) H1B(0.5)
 H1C(0.5) S2(0.15)
5.a Me refined with riding coordinates:
 C2S(H2SA,H2SB,H2SC), C2S(H2SD,H2SE,H2SF), C1S(H1SA,H1SB,H1SC), C1(H1A,H1B,H1C)
5.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C2(H2)
5.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.186
_oxdiff_exptl_absorpt_empirical_full_min 0.844