Phosphonoselenoic Acid Esters from the Reaction between Phosphoroselenoyl Chlorides and Grignard Reagents: Synthetic and Stereochemical Aspects
Murai, Toshiaki; Maekawa, Yuuki; Hirai, Yuuki; Kuwabara, Kazuma; Minoura, Mao; RSC Adv.  (2016) –; doi:10.1039/C6RA00318D

data_7224051
_publ_section_title
;
 Phosphonoselenoic Acid Esters from the Reaction between Phosphoroselenoyl
 Chlorides and Grignard Reagents: Synthetic and Stereochemical Aspects
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA00318D
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_sum            'C24 H21 O2 P Se'
_chemical_formula_weight         451.34
_chemical_name_systematic        'Phosphonoselenoic acid ester'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-11-30 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4584(3)
_cell_length_b                   8.9425(4)
_cell_length_c                   31.2167(13)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.37
_cell_volume                     2082.05(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            58681
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.369
_exptl_absorpt_coefficient_mu    1.897
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6158
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 1911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.093(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0208P)^2^+1.8626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0664
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4659
_reflns_number_total             4756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra00318d2.cif
_cod_data_source_block           Mura1_0m_a
_cod_database_code               7224051
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.703
_shelx_estimated_absorpt_t_max   0.833
_shelx_res_checksum              52064