Reaction of an Enantiomerically Pure Phosphaalkene-Oxazoline with MeM Nucleophiles (M = Li and MgBr): Stereoselectivity and Noninnocence of the P-Mesityl Substituent
Serin, Spencer C.; Patrick, Brian O.; Dake, Gregory R.; Gates, Derek P.; Organometallics  (2014) 141201152116001–; doi:10.1021/om501008m

data_4085003
_publ_section_title
;
 Reaction of an Enantiomerically Pure Phosphaalkene-Oxazoline with MeM
 Nucleophiles (M = Li and MgBr): Stereoselectivity and Noninnocence of the
 P-Mesityl Substituent
;
_journal_name_full               Organometallics
_journal_page_first              141201152116001
_journal_paper_doi               10.1021/om501008m
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C52 H72 Cl3 N2 O2 P2 Pd2, Cl'
_chemical_formula_sum            'C52 H72 Cl4 N2 O2 P2 Pd2'
_chemical_formula_weight         1173.66
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-10-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   20.139(2)
_cell_length_b                   20.139(2)
_cell_length_c                   13.7756(13)
_cell_measurement_reflns_used    7729
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.900
_cell_measurement_theta_min      1.884
_cell_volume                     4838.6(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      90
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker-Nonius APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device
'Bruker-Nonius APEXII CCD area detector and D8 diffractometer'
_diffrn_measurement_device_type  DUO_Mo
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            50106
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.900
_diffrn_reflns_theta_min         1.884
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS. Bruker'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1812
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.911
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 3074 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.048(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         7729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0223P)^2^+4.8663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0652
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                7002
_reflns_number_total             7729
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om501008m_si_001.cif
_cod_data_source_block           platon_sq_s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/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 2935 2014-11-11 08:27:57Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        4838.6(11)
_cod_database_code               4085003
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.587
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1B), C13(H13), C14(H14), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C20(H20), C22(H22)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_fab_checksum              9790
_olex2_submission_special_instructions 'No special instructions were received'