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_7218778
_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         'C26 H20 Cl1 N5 O4 S1'
_chemical_formula_sum            'C26 H20 Cl N5 O4 S'
_chemical_formula_weight         533.99
_chemical_name_systematic
N-(7-benzyl-5-chloro-4-phenyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-N-methyl-2-nitrobenzenesulfonamide
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 103.112(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3204(3)
_cell_length_b                   10.7781(2)
_cell_length_c                   22.4546(7)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    180
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2432.60(12)
_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      180
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.955
_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     1.54180
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17639
_diffrn_reflns_theta_full        72.328
_diffrn_reflns_theta_max         78.618
_diffrn_reflns_theta_min         4.574
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.572
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.39
_refine_ls_extinction_coef       264(8)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0325
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4759
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.0011091
_refine_ls_shift/su_mean         0.0000542
_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: 
 10.5 -4.09 7.57 -0.717 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0397
_refine_ls_wR_factor_gt          0.0391
_refine_ls_wR_factor_ref         0.0391
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                4759
_reflns_number_total             4993
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.11
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0346
_oxford_refine_ls_scale          6.635(11)
_oxford_reflns_number_all        4993
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            c4ra13143f2.cif
_cod_data_source_block           1
_cod_original_cell_volume        2432.59(12)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C26 H20 Cl1 N5 O4 S1'
_cod_database_code               7218778
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   2,X'S) H   (  21,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   (  21,X'S) H   ( 211,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   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 253,X'S) H   ( 252,X'S) H   ( 251,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
END                                                                             
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_iucr_refine_instruction_details_restraints
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NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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