Direct C–H amination and C–H chloroamination of 7-deazapurines
Sabat, Nazarii; Klečka, Martin; Slavětínská, Lenka; Klepetářová, Blanka; Hocek, Michal; RSC Adv. 4 (2014) 62140–; doi:10.1039/C4RA13143F

data_7218780
_publ_section_title
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 Direct C--H amination and C--H chloroamination of 7-deazapurines
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_journal_issue                   107
_journal_name_full               'RSC Adv.'
_journal_page_first              62140
_journal_paper_doi               10.1039/C4RA13143F
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C27 H24 N4 O2 S1'
_chemical_formula_sum            'C27 H24 N4 O2 S'
_chemical_formula_weight         468.58
_chemical_name_systematic
N-(7-benzyl-4-phenyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-N,4-dimethylbenzenesulfonamide
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 104.039(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.7725(4)
_cell_length_b                   10.3703(3)
_cell_length_c                   22.3779(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     4676.6(2)
_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      200
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_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  0.055
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24824
_diffrn_reflns_theta_full        73.729
_diffrn_reflns_theta_max         76.010
_diffrn_reflns_theta_min         4.073
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.490
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  1.00
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       thick
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.0005547
_refine_ls_shift/su_mean         0.0000321
_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: 
 6.40 -0.617 4.72 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0555
_refine_ls_wR_factor_gt          0.0449
_refine_ls_wR_factor_ref         0.0449
_reflns_limit_h_max              25
_reflns_limit_h_min              -26
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                3729
_reflns_number_total             4828
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.28
_oxford_diffrn_Wilson_scale      0.33
_oxford_refine_ls_r_factor_ref   0.0431
_oxford_refine_ls_scale          1.724(3)
_oxford_reflns_number_all        4807
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) H   ( 243,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 273,X'S) H   ( 272,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
END                                                                             
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_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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_cod_data_source_file            c4ra13143f2.cif
_cod_data_source_block           1
_cod_original_cell_volume        4676.61(18)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C27 H24 N4 O2 S1'
_cod_database_code               7218780