The α-hydroxyphosphonate-phosphate rearrangement of a noncyclic substrate - some new observations.
Prechelmacher, Susanne; Mereiter, Kurt; Hammerschmidt, Friedrich; Organic & biomolecular chemistry 16 (2018) 3672–3680; doi:10.1039/c8ob00419f

data_7156238
_publ_section_title
;
 The \a-hydroxyphosphonate-phosphate rearrangement of a noncyclic
 substrate - some new observations.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3672
_journal_page_last               3680
_journal_paper_doi               10.1039/c8ob00419f
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C30 H41 O4 P S'
_chemical_formula_sum            'C30 H41 O4 P S'
_chemical_formula_weight         528.66
_chemical_melting_point          383
_chemical_name_common            'compound 23'
_chemical_name_systematic
'(1R,R~p~)-(1',3',5'(10')-estratrien-3'-ylmethyl) ethyl (1-hydroxy-2-methylsulfanyl-1-phenylethyl)phosphonate'
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2018-01-21 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.00(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.157(6)
_cell_length_b                   6.917(2)
_cell_length_c                   20.174(6)
_cell_measurement_reflns_used    42
_cell_measurement_temperature    293
_cell_measurement_theta_max      22.00
_cell_measurement_theta_min      6.00
_cell_volume                     2923.6(15)
_computing_cell_refinement       'Local software'
_computing_data_collection       'Philips PW1100 (Philips AG, Eindhoven, 1973)'
_computing_data_reduction        'Local software'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Philips PW1100 four-circle diffractometer'
_diffrn_measurement_method       '\q--2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2575
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        0.7
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexanes, isopropanol'
_exptl_crystal_size_max          0.850
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
The absolute structure was fixed by the known absolute
configuration of the 1,3,5(10)-estratrien-3-ol used 
in the synthesis of the title compound.
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         2496
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0288P)^2^+0.0630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                2202
_reflns_number_total             2499
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c8ob00419f2.cif
_cod_data_source_block           compound23
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156238.cif.
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7156238