Direct C-H arylation of purines: development of methodology and its use in regioselective synthesis of 2,6,8-trisubstituted purines.
Cerna, Igor; Pohl, Radek; Klepetarová, Blanka; Hocek, Michal; Organic letters 8 (2006) 5389–5392; doi:10.1021/ol062324j

data_1506289
_publ_section_title
;
 Direct C-H arylation of purines: development of methodology and its use
 in regioselective synthesis of 2,6,8-trisubstituted purines.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5389
_journal_page_last               5392
_journal_paper_doi               10.1021/ol062324j
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C36 H26 N8'
_chemical_formula_sum            'C36 H26 N8'
_chemical_formula_weight         570.66
_chemical_melting_point          567(2)
_chemical_name_systematic        8,8'-bis(9-benzyl-6-phenylpurine)
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             06-07-13
_audit_creation_method           CRYSTALS_ver_12.83
_cell_angle_alpha                104.262(18)
_cell_angle_beta                 91.69(2)
_cell_angle_gamma                96.25(2)
_cell_formula_units_Z            1
_cell_length_a                   5.6460(10)
_cell_length_b                   8.780(2)
_cell_length_c                   14.507(2)
_cell_measurement_reflns_used    8614
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      5
_cell_volume                     691.6(2)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (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      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.939
_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  0.043
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10352
_diffrn_reflns_theta_full        63.742
_diffrn_reflns_theta_max         76.798
_diffrn_reflns_theta_min         5.236
_diffrn_source_type              Xcalibur
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            yellow-green
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       prism
_exptl_crystal_F_000             298
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.20
_refine_ls_extinction_coef       44(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.1154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2502
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000367
_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: 
 6.88 0.676 4.25 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0475
_refine_ls_wR_factor_gt          0.0469
_refine_ls_wR_factor_ref         0.0469
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2502
_reflns_number_total             2732
_reflns_threshold_expression     I>2.0\s(I)
_cod_data_source_file            ol062324jsi20060921_050253.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '292-296 C' was changed to '567(2)' -
it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
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_cod_database_code               1506289