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_4037315
_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-5H-pyrrolo[3,2-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                64.703(14)
_cell_angle_beta                 65.550(17)
_cell_angle_gamma                85.194(12)
_cell_formula_units_Z            2
_cell_length_a                   8.5724(16)
_cell_length_b                   9.5217(11)
_cell_length_c                   10.0248(18)
_cell_measurement_reflns_used    2003
_cell_measurement_temperature    180
_cell_measurement_theta_max      74.1240
_cell_measurement_theta_min      5.1540
_cell_volume                     669.1(2)
_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 0.952
_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  0.054
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6115
_diffrn_reflns_theta_full        66.768
_diffrn_reflns_theta_max         75.829
_diffrn_reflns_theta_min         5.171
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.724
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.42164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.3193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1917
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0764
_refine_ls_shift/su_max          0.0009503
_refine_ls_shift/su_mean         0.0000713
_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: 
 6.45 -0.619 4.36 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0944
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0647
_reflns_limit_h_max              10
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -10
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1917
_reflns_number_total             2658
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   5.90
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0764
_oxford_refine_ls_scale          7.42(2)
_oxford_reflns_number_all        2658
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            jo6b01970_si_002.cif
_cod_data_source_block           1
_cod_original_formula_sum        'C10 H13 Cl1 N3 O3 P1'
_cod_database_code               4037315
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT CL   (   10 ,X'S,U'S)  UNTIL O    (   16 ) 
CONT O    (  131 ,X'S,U'S)  UNTIL O    (  130 ) 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (   18 ) 
CONT C    (  141 ,X'S,U'S)  UNTIL C    (  150 ) 
RIDE N   (   7,X'S) H   (  71,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  17,X'S) H   ( 172,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   ( 141,X'S) H   (1411,X'S) H   (1412,X'S) 
RIDE C   ( 140,X'S) H   (1402,X'S) H   (1401,X'S) 
RIDE C   ( 151,X'S) H   (1512,X'S) H   (1511,X'S) H   (1513,X'S) 
RIDE C   ( 150,X'S) H   (1502,X'S) H   (1503,X'S) H   (1501,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                                                                             
;