Synthesis of dinucleoside acylphosphonites by phosphonodiamidite chemistry and investigation of phosphorus epimerization.
Hersh, William H.; Beilstein journal of organic chemistry 11 (2015) 184–191; doi:10.3762/bjoc.11.19

data_4030514
_publ_section_title
;
 Synthesis of dinucleoside acylphosphonites by phosphonodiamidite
 chemistry and investigation of phosphorus epimerization.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              184
_journal_page_last               191
_journal_paper_doi               10.3762/bjoc.11.19
_journal_volume                  11
_journal_year                    2015
_chemical_formula_moiety         'C19 H33 N2 O P'
_chemical_formula_sum            'C19 H33 N2 O P'
_chemical_formula_weight         336.44
_chemical_name_common            Benzoylphosphonodiamidite
_chemical_name_systematic
;
 (bis(diisopropylamino)phosphanyl)(phenyl)methanone
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 108.8770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8768(8)
_cell_length_b                   9.2589(5)
_cell_length_c                   14.0614(7)
_cell_measurement_reflns_used    9998
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.58
_cell_volume                     1955.87(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Farrugia ORTEP-3/v2.02'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21786
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.584
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V 2008/1 (Bruker AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.406
_exptl_crystal_size_mid          0.374
_exptl_crystal_size_min          0.312
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.7900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0821
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3921
_reflns_number_total             4311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-11-19-S2.cif
_cod_data_source_block           WH744_1_p48_0ma
_cod_depositor_comments          'Adding full bibliography for 4030514.cif.'
_cod_database_code               4030514
_shelxl_version_number           2014-3
_shelx_res_checksum              39973
_shelx_hkl_checksum              59352