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_7061768
_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      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-01 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.129(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.4433(9)
_cell_length_b                   27.1914(16)
_cell_length_c                   16.9657(14)
_cell_measurement_reflns_used    3254
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.0590
_cell_measurement_theta_min      3.7940
_cell_volume                     6039.6(8)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.921
_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    -45.00  44.00   1.00   60.00    --  -23.92  57.00  90.00   89
  2  \w    -91.00  -3.00   1.00   60.00    --  -23.92 -77.00 120.00   88
  3  \w    -90.00   3.00   1.00   60.00    --  -23.92 -77.00-150.00   93
  4  \w    -51.00  40.00   1.00   60.00    --  -23.92  77.00 -30.00   91
;
_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      -0.0162991000
_diffrn_orient_matrix_UB_12      0.0224696000
_diffrn_orient_matrix_UB_13      0.0141634000
_diffrn_orient_matrix_UB_21      -0.0516246000
_diffrn_orient_matrix_UB_22      -0.0065799000
_diffrn_orient_matrix_UB_23      -0.0163842000
_diffrn_orient_matrix_UB_31      -0.0022469000
_diffrn_orient_matrix_UB_32      -0.0114771000
_diffrn_orient_matrix_UB_33      0.0370977000
_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  0.0559
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23879
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.496
_diffrn_reflns_theta_min         3.749
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86778
_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    1.326
_exptl_crystal_description       prism
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         8489
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1710
_refine_ls_R_factor_gt           0.0683
_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^)+(0.1007P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.2487
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3428
_reflns_number_total             8489
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03002k2.cif
_cod_data_source_block           exp_1044
_cod_depositor_comments
'Adding full bibliography for 7061766--7061768.cif.'
_cod_database_code               7061768
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.862
_reflns_odcompleteness_completeness 99.62
_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 C(H,H) groups, All C(H,H,H,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
 C3-C12
 1.54 with sigma of 0.02
 C12-C13
 1.54 with sigma of 0.02
 C12-C11
 1.54 with sigma of 0.02
 C14-C00W
 1.54 with sigma of 0.02
 C14-C5
 1.54 with sigma of 0.02
 C14-C7
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C2S) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(S3) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: S1S(0.8) H14A(0.5) H14B(0.5) H14C(0.5) H14D(0.5) H1SD(0.2)
 H1SE(0.2) H1SF(0.2) H1SA(0.8) H1SB(0.8) H1SC(0.8) C13(0.8) H13A(0.8) H13B(0.8)
 H13C(0.8) H12A(0.8) H12B(0.8) H12C(0.2) H12D(0.2) C2S(0.8) H2SA(0.8) H2SB(0.8)
 H2SC(0.8) C3(0.2) H3A(0.2) H3B(0.2) H3C(0.2) C7(0.5) H7A(0.5) H7B(0.5)
 H7C(0.5) C5(0.5) H5A(0.5) H5B(0.5) H5C(0.5) C1(0.2) H1A(0.2) H1B(0.2) H1C(0.2)
 S3(0.2)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C00S(H00A,H00B), C11(H11A,H11B), C00W(H00C,H00D), C14(H14A,
 H14B), C14(H14C,H14D), C12(H12A,H12B), C12(H12C,H12D)
5.b Me refined with riding coordinates:
 C4S(H4SA,H4SB,H4SC), C13(H13A,H13B,H13C), C3(H3A,H3B,H3C), C7(H7A,H7B,H7C),
 C5(H5A,H5B,H5C)
5.c Aromatic/amide H refined with riding coordinates:
 N16(H16), N3(H3), C6(H6), C19(H19)
5.d Idealised Me refined as rotating group:
 C3S(H3SA,H3SB,H3SC), C1S(H1SD,H1SE,H1SF), C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,
 H2SC), C1(H1A,H1B,H1C)
;
_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 1.092
_oxdiff_exptl_absorpt_empirical_full_min 0.926