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_4037317
_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 H14 Cl1 N4 O3 P1'
_chemical_formula_sum            'C10 H14 Cl N4 O3 P'
_chemical_formula_weight         304.67
_chemical_name_systematic
'diethyl (2-amino-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                113.60(2)
_cell_angle_beta                 94.47(3)
_cell_angle_gamma                109.16(2)
_cell_formula_units_Z            2
_cell_length_a                   8.221(3)
_cell_length_b                   10.018(3)
_cell_length_c                   10.186(4)
_cell_measurement_reflns_used    90
_cell_measurement_temperature    293
_cell_measurement_theta_max      21.585
_cell_measurement_theta_min      2.227
_cell_volume                     704.6(5)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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      293
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21458
_diffrn_reflns_theta_full        26.124
_diffrn_reflns_theta_max         27.212
_diffrn_reflns_theta_min         2.249
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             316.000
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.46
_refine_ls_extinction_coef       46.647
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.1363
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2061
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0625
_refine_ls_shift/su_max          0.0050988
_refine_ls_shift/su_mean         0.0002367
_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: 
 0.668 0.843 0.599 0.299 0.864E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1069
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0553
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -12
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2061
_reflns_number_total             3089
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.91
_oxford_diffrn_Wilson_scale      8.80
_oxford_refine_ls_r_factor_ref   0.0625
_oxford_refine_ls_scale          0.3785(11)
_oxford_reflns_number_all        3089
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            jo6b01970_si_003.cif
_cod_data_source_block           1
_cod_original_cell_volume        704.5(5)
_cod_original_formula_sum        'C10 H14 Cl1 N4 O3 P1'
_cod_database_code               4037317