Fe-Catalyzed Three-Component Dicarbofunctionalization of Unactivated Alkenes with Alkyl Halides and Grignard Reagents
Liu, Lei; Lee, Wes; Youshaw, Cassandra R.; Yuan, Mingbin; Geherty, Michael B.; Zavalij, Peter Y.; gutierrez, osvaldo; Chemical Science  (2020) –; doi:10.1039/D0SC02127J

data_1558663
_publ_section_title
;
 Fe-Catalyzed Three-Component Dicarbofunctionalization of Unactivated
 Alkenes with Alkyl Halides and Grignard Reagents
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02127J
_journal_year                    2020
_chemical_formula_moiety         'C22 H28 O'
_chemical_formula_sum            'C22 H28 O'
_chemical_formula_weight         308.44
_chemical_name_common
cis-3-([1,1?-biphenyl]-4-ylmethyl)-4-neopentyltetrahydrofuran
_chemical_name_systematic        LL-2
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL & ZCIF'
_audit_update_record
;
2020-04-14 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                96.1247(13)
_cell_angle_beta                 90.4111(13)
_cell_angle_gamma                99.2413(14)
_cell_formula_units_Z            2
_cell_length_a                   6.1587(5)
_cell_length_b                   9.3173(8)
_cell_length_c                   15.9930(13)
_cell_measurement_reflns_used    7583
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      31.9
_cell_measurement_theta_min      2.2
_cell_volume                     900.36(13)
_computing_cell_refinement       'Apex2, Saint (Bruker, 2012)'
_computing_data_collection       'Apex2 (Bruker, 2012)'
_computing_data_reduction        'Apex2, Saint'
_computing_molecular_graphics    'Olex2 (Dolomanov, 2009)'
_computing_publication_material  'Apex2, SHELXL, Platon (Spek, 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015c)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      149(2)
_diffrn_detector                 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.1263299
_diffrn_orient_matrix_UB_12      0.0823452
_diffrn_orient_matrix_UB_13      0.0008779
_diffrn_orient_matrix_UB_21      -0.0105570
_diffrn_orient_matrix_UB_22      0.0194048
_diffrn_orient_matrix_UB_23      0.0624301
_diffrn_orient_matrix_UB_31      0.1049195
_diffrn_orient_matrix_UB_32      -0.0693520
_diffrn_orient_matrix_UB_33      0.0076685
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16141
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.243
_diffrn_reflns_theta_min         2.228
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0090P)^2^+0.4940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4876
_reflns_number_total             5721
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02127j2.cif
_cod_data_source_block           UM3392
_cod_database_code               1558663
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              84994