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_1506290
_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         'C25 H20 N4'
_chemical_formula_sum            'C25 H20 N4'
_chemical_formula_weight         376.46
_chemical_melting_point          447.1(10)
_chemical_name_systematic        9-Benzyl-6-phenyl-8-(4-methylphenyl)purine
_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             06-08-09
_audit_creation_method           CRYSTALS_ver_12.83
_cell_angle_alpha                101.247(7)
_cell_angle_beta                 114.349(8)
_cell_angle_gamma                106.926(7)
_cell_formula_units_Z            2
_cell_length_a                   10.1257(8)
_cell_length_b                   10.4037(8)
_cell_length_c                   11.2572(9)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      5
_cell_volume                     963.70(18)
_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 0.989
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13152
_diffrn_reflns_theta_full        68.013
_diffrn_reflns_theta_max         76.420
_diffrn_reflns_theta_min         4.624
_diffrn_source_type              Xcalibur
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            'light pink'
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.24
_refine_ls_extinction_coef       29(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.1423
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.002477
_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: 
 5.95 2.21 3.94 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0591
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0562
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3233
_reflns_number_total             3826
_reflns_threshold_expression     I>2.0\s(I)
_cod_data_source_file            ol062324jsi20060921_050326.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '173-175 C' was changed to
'447.1(10)' - 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               1506290