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_7218779
_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         'C21 H19 N5 O5 S1'
_chemical_formula_sum            'C21 H19 N5 O5 S'
_chemical_formula_weight         453.48
_chemical_name_systematic
N-(7-benzyl-4-methoxy-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-N-methyl-2-nitrobenzenesulfonamide
_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   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                76.069(2)
_cell_angle_beta                 76.692(2)
_cell_angle_gamma                76.024(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0254(2)
_cell_length_b                   8.5175(2)
_cell_length_c                   16.5553(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    290
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1047.93(5)
_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      290
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.978
_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  0.033
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18491
_diffrn_reflns_theta_full        69.079
_diffrn_reflns_theta_max         75.911
_diffrn_reflns_theta_min         5.458
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.766
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.83
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.30
_refine_ls_extinction_coef       79(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.8205
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.0041873
_refine_ls_shift/su_mean         0.0005784
_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: 
 9.05 -0.282 4.96 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0430
_refine_ls_wR_factor_gt          0.0419
_refine_ls_wR_factor_ref         0.0419
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                3984
_reflns_number_total             4263
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.41
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0361
_oxford_refine_ls_scale          11.76(2)
_oxford_reflns_number_all        4263
_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        1047.92(5)
_cod_original_formula_sum        'C21 H19 N5 O5 S1'
_cod_database_code               7218779
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   2,X'S) H   (  91,X'S) 
RIDE C   (   7,X'S) H   ( 131,X'S) 
RIDE C   (  11,X'S) H   ( 152,X'S) H   ( 153,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 291,X'S) 
RIDE C   (  17,X'S) H   ( 301,X'S) 
RIDE C   (  18,X'S) H   ( 311,X'S) 
RIDE C   (  19,X'S) H   ( 321,X'S) 
RIDE C   (  20,X'S) H   ( 232,X'S) H   ( 231,X'S) H   ( 233,X'S) 
RIDE C   (  25,X'S) H   ( 162,X'S) H   ( 161,X'S) 
RIDE C   (  27,X'S) H   ( 181,X'S) 
RIDE C   (  28,X'S) H   ( 191,X'S) 
RIDE C   (  29,X'S) H   ( 201,X'S) 
RIDE C   (  30,X'S) H   ( 211,X'S) 
RIDE C   (  31,X'S) H   ( 221,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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