Purinyl N1-Directed Aromatic C-H Oxidation in 6-Arylpurines and 6-Arylpurine Nucleosides
Raghu Ram Chamala; Damon Parrish; Padmanava Pradhan; Mahesh K. Lakshman; Journal of Organic Chemistry 78 (2013) 7423–7435; doi:10.1021/jo4008282

data_4028454
_publ_contact_author_address
;
Laboratory for the Structure of Matter
Naval Research Laboratory
Washington, DC 20375
;
_publ_contact_author_email       damon.parrish@nrl.navy.mil
_publ_contact_author_fax         202-767-6874
_publ_contact_author_name        'Dr Damon A. Parrish'
_publ_contact_author_phone       202-404-2141
_publ_section_title
;
 Purinyl N1-Directed Aromatic C-H Oxidation in 6-Arylpurines and
 6-Arylpurine Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7423
_journal_page_last               7435
_journal_paper_doi               10.1021/jo4008282
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C24 H18 N4 O2'
_chemical_formula_sum            'C24 H18 N4 O2'
_chemical_formula_weight         394.42
_chemical_name_systematic
; 
 3-(9-benzyl-9H-purin-6-yl)naphthalen-2-yl acetate 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-05-20
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_cell_angle_alpha                84.335(5)
_cell_angle_beta                 84.569(5)
_cell_angle_gamma                70.466(5)
_cell_formula_units_Z            2
_cell_length_a                   8.102(2)
_cell_length_b                   10.608(3)
_cell_length_c                   12.154(3)
_cell_measurement_temperature    296(2)
_cell_volume                     977.5(4)
_computing_cell_refinement       'Bruker APEX2 v2009.3-0 (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 v2009.3-0 (Bruker, 2009)'
_computing_data_reduction
;
Bruker SAINT v7.60A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8964
_diffrn_reflns_theta_full        26.58
_diffrn_reflns_theta_max         26.58
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.1199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1363
_reflns_number_gt                2740
_reflns_number_total             3949
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo4008282_si_004.cif
_cod_data_source_block           lak012
_cod_original_cell_volume        977.5(5)
_cod_database_code               4028454