Convenient access to pyrrolidin-3-ylphosphonic acids and tetrahydro-2H-pyran-3-ylphosphonates with multiple contiguous stereocenters from nonracemic adducts of a Ni(II)-catalyzed Michael reaction
Reznikov, Alexander N.; Nikerov, Dmitry S.; Sibiryakova, Anastasiya E.; Rybakov, Victor B.; Golovin, Evgeniy V.; Klimochkin, Yuri N.; Beilstein Journal of Organic Chemistry 16 (2020) 2073–2079; doi:10.3762/bjoc.16.174

data_4038715
_publ_contact_author             'Dr. Victor B. Rybakov'
_publ_section_title
;
 Convenient access to pyrrolidin-3-ylphosphonic acids and
 tetrahydro-2H-pyran-3-ylphosphonates with multiple contiguous
 stereocenters from nonracemic adducts of a Ni(II)-catalyzed Michael
 reaction
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              2073
_journal_page_last               2079
_journal_paper_doi               10.3762/bjoc.16.174
_journal_volume                  16
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H22 N O7 P'
_chemical_formula_sum            'C15 H22 N O7 P'
_chemical_formula_weight         359.31
_chemical_melting_point_gt       466
_chemical_melting_point_lt       467
_chemical_name_systematic
;
 Dimethyl 
(2-hydroxy-2,6-dimethyl-5-nitro-4-phenyltetrahydro-2H-pyran-3-yl)phosphonate
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6607(9)
_cell_length_b                   11.0178(10)
_cell_length_c                   17.0785(17)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      34.13
_cell_measurement_theta_min      30.02
_cell_volume                     1817.8(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4        (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3      (Farrugia, 1997)'
_computing_publication_material  'WinGX        (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013  (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS97     (Sheldrick, 2013)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '\k--geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non--profiled \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  0.0186
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3981
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         74.882
_diffrn_reflns_theta_min         4.776
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    1.660
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_correction_T_min  0.8936
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_preparation       methanol
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1198 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.001(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0417P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                3175
_reflns_number_total             3613
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            KLIM1818dep.cif
_cod_data_source_block           KLIM1818
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'x--ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/Beilstein/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4038715.cif.
;
_cod_database_code               4038715
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.968
_exptl_absorpt_factor_mur        0.017
_diffrn_standards_decay_corr_max 1.016
_diffrn_standards_decay_corr_min 0.990
_shelxl_version_number           2013-4
_shelx_res_checksum              88379
_shelx_hkl_checksum              95968