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_7218781
_publ_section_title
;
 Direct C--H amination and C--H chloroamination of 7-deazapurines
;
_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 H21 N5 O4 S1'
_chemical_formula_sum            'C26 H21 N5 O4 S'
_chemical_formula_weight         499.55
_chemical_name_systematic
N-(7-benzyl-4-phenyl-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     other
_cell_angle_alpha                81.5862(13)
_cell_angle_beta                 70.0238(15)
_cell_angle_gamma                67.3666(15)
_cell_formula_units_Z            4
_cell_length_a                   12.8359(2)
_cell_length_b                   14.6425(2)
_cell_length_c                   16.3039(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    180
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2657.76(8)
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.967
_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  0.050
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10790
_diffrn_reflns_theta_full        67.969
_diffrn_reflns_theta_max         76.370
_diffrn_reflns_theta_min         4.219
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.415
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.68
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.35
_refine_ls_extinction_coef       68(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9677
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         9618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.0006447
_refine_ls_shift/su_mean         0.0000338
_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: 
 6.27 -3.05 3.10 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0404
_refine_ls_wR_factor_gt          0.0398
_refine_ls_wR_factor_ref         0.0395
_reflns_limit_h_max              16
_reflns_limit_h_min              -14
_reflns_limit_k_max              18
_reflns_limit_k_min              -18
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                9994
_reflns_number_total             10790
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.87
_oxford_diffrn_Wilson_scale      0.04
_oxford_refine_ls_r_factor_ref   0.0425
_oxford_refine_ls_scale          4.915(5)
_oxford_reflns_number_all        10751
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            c4ra13143f2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_original_cell_volume        2657.75(8)
_cod_original_formula_sum        'C26 H21 N5 O4 S1'
_cod_database_code               7218781
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
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   (  20,X'S) H   ( 201,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) H   ( 243,X'S) H   ( 242,X'S) 
RIDE C   (  30,X'S) H   ( 302,X'S) H   ( 301,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) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE C   (  60,X'S) H   ( 603,X'S) H   ( 602,X'S) H   ( 601,X'S) 
RIDE C   (  61,X'S) H   ( 612,X'S) H   ( 611,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) 
RIDE C   (  64,X'S) H   ( 641,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;