Chiral Ferrocenyl P,N-Ligands for Palladium-Catalyzed Asymmetric Formal [3 + 2] Cycloaddition of Propargylic Esters with β-Ketoesters: Access to Functionalized Chiral 2,3-Dihydrofurans.
Zhou, Yong; Zhu, Fu-Lin; Liu, Zhen-Ting; Zhou, Xiao-Mao; Hu, Xiang-Ping; Organic letters 18 (2016) 2734–2737; doi:10.1021/acs.orglett.6b01192

data_1543339
_publ_section_title
;
 Chiral Ferrocenyl P,N-Ligands for Palladium-Catalyzed Asymmetric Formal
 [3 + 2] Cycloaddition of Propargylic Esters with \b-Ketoesters: Access to
 Functionalized Chiral 2,3-Dihydrofurans.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2734
_journal_page_last               2737
_journal_paper_doi               10.1021/acs.orglett.6b01192
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H32 Fe N3 P, C2 H6 O'
_chemical_formula_sum            'C35 H38 Fe N3 O P'
_chemical_formula_weight         603.50
_chemical_name_systematic
;
 ?
;
_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
_audit_creation_date             2015-01-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.678(2)
_cell_length_b                   10.701(2)
_cell_length_c                   27.346(6)
_cell_measurement_reflns_used    9816
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      0.7446
_cell_volume                     3124.7(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution
;
 'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0078
_diffrn_orient_matrix_UB_12      -0.0923
_diffrn_orient_matrix_UB_13      -0.0136
_diffrn_orient_matrix_UB_21      -0.0156
_diffrn_orient_matrix_UB_22      -0.0147
_diffrn_orient_matrix_UB_23      0.0910
_diffrn_orient_matrix_UB_31      -0.0359
_diffrn_orient_matrix_UB_32      -0.0020
_diffrn_orient_matrix_UB_33      -0.0065
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            21674
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         1.489
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8537
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.521
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.044(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         6729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0285P)^2^+1.6182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.869
_reflns_number_gt                6345
_reflns_number_total             6729
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01192_si_002.cif
_cod_data_source_block           sa3830
_cod_depositor_comments
'Adding full bibliography for 1543338--1543339.cif.'
_cod_original_cell_volume        3124.8(11)
_cod_database_code               1543339
_shelxl_version_number           2013-4
_diffrn_number_total             7504
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21),
  C22(H22), C29(H29), C30(H30), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_shelx_res_checksum              8380
_shelx_hkl_checksum              18365