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_7061766
_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         'C14 H10 Cl N5 O S'
_chemical_formula_sum            'C14 H10 Cl N5 O S'
_chemical_formula_weight         331.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-12
_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                 109.568(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0095(12)
_cell_length_b                   9.0931(5)
_cell_length_c                   14.1600(11)
_cell_measurement_reflns_used    2661
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.7150
_cell_measurement_theta_min      3.7880
_cell_volume                     1457.0(2)
_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 0.992
_diffrn_measured_fraction_theta_max 0.858
_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    -34.00  -8.00   1.00   15.00    --   22.67 -87.00 -81.00   26
  2  \w    -27.00  -1.00   1.00   15.00    --  -24.24 -87.00 -81.00   26
  3  \w    -60.00  39.00   1.00   15.00    --  -24.24  87.00  36.00   99
  4  \w     54.00  99.00   1.00   15.00    --   22.67 178.00-120.00   45
  5  \w    -47.00  53.00   1.00   15.00    --   22.67 -77.00-150.00  100
  6  \w      9.00  58.00   1.00   15.00    --   22.67 -87.00 -81.00   49
;
_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      0.0273711000
_diffrn_orient_matrix_UB_12      0.0642161000
_diffrn_orient_matrix_UB_13      -0.0103083000
_diffrn_orient_matrix_UB_21      0.0559332000
_diffrn_orient_matrix_UB_22      -0.0270120000
_diffrn_orient_matrix_UB_23      0.0304222000
_diffrn_orient_matrix_UB_31      0.0070920000
_diffrn_orient_matrix_UB_32      -0.0349948000
_diffrn_orient_matrix_UB_33      -0.0424190000
_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  0.0368
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10653
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.904
_diffrn_reflns_theta_min         3.601
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65146
_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    1.512
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.002(2)
_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   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0611
_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          0.1761
_refine_ls_wR_factor_ref         0.2286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2459
_reflns_number_total             3948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03002k2.cif
_cod_data_source_block           exp_1047
_cod_depositor_comments
'Adding full bibliography for 7061766--7061768.cif.'
_cod_database_code               7061766
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.893
_shelx_estimated_absorpt_t_min   0.849
_reflns_odcompleteness_completeness 98.44
_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
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C16(H16), C17(H17)
;
_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 1.260
_oxdiff_exptl_absorpt_empirical_full_min 0.812