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_4085004
_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
'0.04(Cl2 P Pd), C26 H36 Cl1.92 N O P0.96 Pd0.96'
_chemical_formula_sum            'C26 H36 Cl2 N O P Pd'
_chemical_formula_weight         586.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                 95.114(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.246(3)
_cell_length_b                   15.111(5)
_cell_length_c                   9.629(3)
_cell_measurement_reflns_used    3452
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      21.97
_cell_measurement_theta_min      2.21
_cell_volume                     1340.0(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_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 0.979
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device
'Bruker-Nonius APEXII CCD area detector and D8 diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11966
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        22.500
_diffrn_reflns_theta_max         22.367
_diffrn_reflns_theta_min         2.123
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0767 before and 0.0560 after correction.
The Ratio of minimum to maximum transmission is 0.7573.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       plate
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.080
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details
;
 Flack x determined using 1367 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     295
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0523P)^2^+3.8216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3056
_reflns_number_total             3410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om501008m_si_001.cif
_cod_data_source_block           mo_dg202_0m
_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 
;
_cod_database_code               4085004
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(P1A) = Uanis(P1)
Uanis(Cl1A) = Uanis(Cl1)
Uanis(Cl2A) = Uanis(Cl2)
Uanis(Pd1A) = Uanis(Pd1)
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Pd1)=Sof(Cl2)=Sof(Cl1)=Sof(P1)=1-FVAR(1)
 Sof(Pd1A)=Sof(Cl2A)=Sof(P1A)=Sof(Cl1A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C15(H15), C1(H1), C14(H14)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
5.c Me refined with riding coordinates:
 C2(H2A,H2B,H2C)
5.d Aromatic/amide H refined with riding coordinates:
 C20(H20), C8(H8), C6(H6), C7(H7), C5(H5), C22(H22), C4(H4)
5.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C24(H24A,H24B,H24C), C10(H10A,H10B,H10C), C25(H25A,H25B,
 H25C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'