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_1543338
_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         'C23 H17 Br O3'
_chemical_formula_sum            'C23 H17 Br O3'
_chemical_formula_weight         421.27
_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   mixed
_audit_creation_date             2015-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.09(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.4774(11)
_cell_length_b                   14.656(3)
_cell_length_c                   11.788(2)
_cell_measurement_reflns_used    3025
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4849
_cell_measurement_theta_min      2.2533
_cell_volume                     921.7(3)
_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 0.996
_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      -0.0888
_diffrn_orient_matrix_UB_12      0.0524
_diffrn_orient_matrix_UB_13      0.1565
_diffrn_orient_matrix_UB_21      0.0567
_diffrn_orient_matrix_UB_22      0.0311
_diffrn_orient_matrix_UB_23      0.0218
_diffrn_orient_matrix_UB_31      -0.0340
_diffrn_orient_matrix_UB_32      0.0772
_diffrn_orient_matrix_UB_33      -0.0215
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10187
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.298
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.251
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6665
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1722 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.008(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4129
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0325P)^2^+0.2616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3964
_reflns_number_total             4129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01192_si_003.cif
_cod_data_source_block           sa3855
_cod_depositor_comments
'Adding full bibliography for 1543338--1543339.cif.'
_cod_original_cell_volume        921.8(3)
_cod_database_code               1543338
_shelxl_version_number           2013-4
_diffrn_number_total             2194
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C15(H15), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              13464
_shelx_hkl_checksum              13357