Asymmetric 1,3-dipolar cycloaddition reaction of chiral 1-alkyl-1,2-diphospholes with diphenyldiazomethane
Ganushevich, Yulia; Zagidullin, Almaz; Kondrashova, Svetlana; Latypov, Shamil; Miluykov, Vasili; Lönnecke, Peter; Hey-Hawkins, Evamarie; RSC Advances 10 (2020) 39060–39066; doi:10.1039/D0RA08080B

data_7241662
_publ_section_title
;
 Asymmetric 1,3-dipolar cycloaddition reaction of chiral
 1-alkyl-1,2-diphospholes with diphenyldiazomethane
;
_journal_issue                   64
_journal_name_full               'RSC Advances'
_journal_page_first              39060
_journal_page_last               39066
_journal_paper_doi               10.1039/D0RA08080B
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C44 H44 P2, C4 H8 O'
_chemical_formula_sum            'C48 H52 O P2'
_chemical_formula_weight         706.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-03-04 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.889(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2172(4)
_cell_length_b                   10.3390(3)
_cell_length_c                   22.6719(5)
_cell_measurement_reflns_used    7073
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      31.0960
_cell_measurement_theta_min      2.2990
_cell_volume                     3949.22(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics
;
 ORTEP3 for Windows
 L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
 or
 DIAMOND Version 4.5.3
 K. Brandenburg, Crystal Impact GbR, Bonn, Germany
;
_computing_publication_material
;
 WINGX
 L.J. Farrugia,
 J. Appl. Cryst., 2012, 45, 849-854.
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 16.3560
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            26465
_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         30.508
_diffrn_reflns_theta_min         2.311
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       plate
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 3507 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     590
_refine_ls_number_reflns         12072
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0778P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                9468
_reflns_number_total             12072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra08080b2.cif
_cod_data_source_block           5a_x1570fin
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7241662
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              44986