Direct C-H sulfenylation of purines and deazapurines.
Klečka, Martin; Pohl, Radek; Cejka, Jan; Hocek, Michal; Organic & biomolecular chemistry 11 (2013) 5189–5193; doi:10.1039/c3ob40881g

data_7153028
_publ_section_title
;
 Direct C-H sulfenylation of purines and deazapurines.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5189
_journal_page_last               5193
_journal_paper_doi               10.1039/c3ob40881g
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C18 H13 N3 S1'
_chemical_formula_sum            'C18 H13 N3 S'
_chemical_formula_weight         303.39
_chemical_name_systematic
4-phenyl-7-(phenylthio)-5H-pyrrolo[3,2-d]pyrimidine
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 103.118(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8659(2)
_cell_length_b                   18.4844(5)
_cell_length_c                   11.9993(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    190
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1483.12(8)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      190
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6709
_diffrn_reflns_theta_full        68.667
_diffrn_reflns_theta_max         77.154
_diffrn_reflns_theta_min         4.476
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.919
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.31
_refine_ls_extinction_coef       34(7)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.0004148
_refine_ls_shift/su_mean         0.0000632
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
19.7 -7.13 17.2
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0484
_refine_ls_wR_factor_gt          0.0467
_refine_ls_wR_factor_ref         0.0467
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2707
_reflns_number_total             3014
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.70
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0369
_oxford_refine_ls_scale          8.58(2)
_oxford_reflns_number_all        3014
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            c3ob40881g.txt
_cod_data_source_block           1
_cod_original_cell_volume        1483.11(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C18 H13 N3 S1'
_cod_database_code               7153028