C-H Phosphonation of Pyrrolopyrimidines: Synthesis of Substituted 7- and 9-Deazapurine-8-phosphonate Derivatives.
Sabat, Nazarii; Poštová Slavětínská, Lenka; Klepetářová, Blanka; Hocek, Michal; The Journal of organic chemistry 81 (2016) 9507–9514; doi:10.1021/acs.joc.6b01970

data_4037316
_publ_section_title
;
 C-H Phosphonation of Pyrrolopyrimidines: Synthesis of Substituted 7- and
 9-Deazapurine-8-phosphonate Derivatives.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9507
_journal_page_last               9514
_journal_paper_doi               10.1021/acs.joc.6b01970
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C10 H13 Cl1 N3 O3 P1'
_chemical_formula_sum            'C10 H13 Cl N3 O3 P'
_chemical_formula_weight         289.66
_chemical_name_systematic
'diethyl (4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phosphonate'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                93.736(3)
_cell_angle_beta                 97.778(4)
_cell_angle_gamma                91.382(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8996(4)
_cell_length_b                   8.2513(4)
_cell_length_c                   10.2912(4)
_cell_measurement_reflns_used    10497
_cell_measurement_temperature    180
_cell_measurement_theta_max      75.6710
_cell_measurement_theta_min      4.3210
_cell_volume                     662.85(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      180
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_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  0.081
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16239
_diffrn_reflns_theta_full        70.505
_diffrn_reflns_theta_max         75.812
_diffrn_reflns_theta_min         4.346
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.759
_exptl_absorpt_correction_T_max  0.55
_exptl_absorpt_correction_T_min  0.01
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.41
_refine_ls_extinction_coef       20(2)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0633
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.0004394
_refine_ls_shift/su_mean         0.0000343
_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: 
 8.73 1.63 6.39 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0629
_refine_ls_wR_factor_gt          0.0548
_refine_ls_wR_factor_ref         0.0548
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2403
_reflns_number_total             2697
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.76
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0454
_oxford_refine_ls_scale          8.09(2)
_oxford_reflns_number_all        2697
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            jo6b01970_si_004.cif
_cod_data_source_block           1
_cod_original_formula_sum        'C10 H13 Cl1 N3 O3 P1'
_cod_database_code               4037316
_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 N   (   9,X'S) H   (  91,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 153,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 182,X'S) H   ( 181,X'S) H   ( 183,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                                                                             
;