Direct C–H borylation and C–H arylation of pyrrolo[2,3-d]pyrimidines: synthesis of 6,8-disubstituted 7-deazapurines
Klečka, Martin; Pohl, Radek; Klepetářová, Blanka; Hocek, Michal; Organic & Biomolecular Chemistry 7 (2009) 866–868; doi:10.1039/b900218a

data_7150639
_publ_section_title
;
 Direct C--H borylation and C--H arylation of
 pyrrolo[2,3-d]pyrimidines: synthesis of 6,8-disubstituted
 7-deazapurines
;
_journal_issue                   5
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              866
_journal_page_last               868
_journal_paper_doi               10.1039/b900218a
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C25 H26 B1 N3 O2'
_chemical_formula_sum            'C25 H26 B N3 O2'
_chemical_formula_weight         411.31
_chemical_name_common
;(7-benzyl-4-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-
2-yl)-7H-pyrrolo(2
;
_chemical_name_systematic
(7-benzyl-4-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine)
_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
_audit_creation_date             08-09-25
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                98.5162(18)
_cell_angle_beta                 97.4398(18)
_cell_angle_gamma                103.2928(18)
_cell_formula_units_Z            4
_cell_length_a                   12.0486(3)
_cell_length_b                   12.5522(3)
_cell_length_c                   15.7030(4)
_cell_measurement_reflns_used    24370
_cell_measurement_temperature    298
_cell_measurement_theta_max      77
_cell_measurement_theta_min      4
_cell_volume                     2252.52(10)
_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      298
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            73819
_diffrn_reflns_theta_full        72.963
_diffrn_reflns_theta_max         77.621
_diffrn_reflns_theta_min         3.681
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Analytical Absorption (De Meulenaer & Tompa, 1965)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.66
_refine_diff_density_min         -0.23
_refine_ls_extinction_coef       46(11)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0755
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         4276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.000248
_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:
14.5 3.67 12.7
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0785
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0675
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                4276
_reflns_number_total             9449
_reflns_threshold_expression     I>2.0\s(I)
_oxford_refine_ls_r_factor_ref   0.0589
_oxford_refine_ls_scale          4.713(13)
_oxford_reflns_number_all        9413
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            b900218a.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C25 H26 B1 N3 O2'
_cod_database_code               7150639