An efficient asymmetric hydrophosphonylation of unsaturated amides catalyzed by rare-earth metal amides [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 with phenoxy-functionalized chiral prolinols
Fei, Zenghui; Zeng, Chao; Lu, Chengrong; Zhao, Bei; Yao, Yingming; RSC Adv. 7 (2017) 19306–; doi:10.1039/C7RA00468K

data_7228756
_publ_section_title
;
 An efficient asymmetric hydrophosphonylation of unsaturated amides
 catalyzed by rare-earth metal amides [(Me3Si)2N]3RE(\m-Cl)Li(THF)3 with
 phenoxy-functionalized chiral prolinols
;
_journal_issue                   31
_journal_name_full               'RSC Adv.'
_journal_page_first              19306
_journal_paper_doi               10.1039/C7RA00468K
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H26 N O4 P'
_chemical_formula_sum            'C20 H26 N O4 P'
_chemical_formula_weight         375.39
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-03-06 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6958(8)
_cell_length_b                   10.0818(9)
_cell_length_c                   21.4683(19)
_cell_measurement_reflns_used    1046
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.6200
_cell_measurement_theta_min      3.4870
_cell_volume                     2098.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   26.00   77.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2428   77.0000  -90.0000 51

  2 omega  -11.00   15.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803  -99.0000 -150.0000 26

  3 omega  -90.00  -60.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803  -57.0000   90.0000 30

  4 omega  -31.00    9.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803  -57.0000   90.0000 40

  5 omega -106.00  -71.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803 -178.0000  -60.0000 35
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0481184000
_diffrn_orient_matrix_UB_12      -0.0371749000
_diffrn_orient_matrix_UB_13      -0.0177594000
_diffrn_orient_matrix_UB_21      -0.0188688000
_diffrn_orient_matrix_UB_22      0.0360497000
_diffrn_orient_matrix_UB_23      -0.0270581000
_diffrn_orient_matrix_UB_31      0.0517560000
_diffrn_orient_matrix_UB_32      0.0476402000
_diffrn_orient_matrix_UB_33      0.0066401000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.1033
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7767
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.831
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 419 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(14)
_refine_ls_extinction_coef       0.0036(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3594
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.1537
_refine_ls_R_factor_gt           0.0599
_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^)+(0.0358P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                1654
_reflns_number_total             3594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra00468k2.cif
_cod_data_source_block           g170303a
_cod_database_code               7228756
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C19-C20
 1.54 with sigma of 0.02
 C20-C19
 1.54 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C19(H19A,H19B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 N003(H003), C12(H12), C13(H13), C16(H16), C6(H6), C14(H14), C4(H4), C15(H15),
 C2(H2), C3(H3), C5(H5)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2017-03-03
_olex2_submission_special_instructions 'No special instructions were received'