Mechanism-Based Design and Optimization of a Catalytic Electrophilic Cyclopropanation without Diazomethane
Tchawou, Augustin A. S. W.; Raducan, Mihai; Chen, Peter; Organometallics 36 (2017) 180–; doi:10.1021/acs.organomet.6b00531

data_4087008
_publ_section_title
;
 Mechanism-Based Design and Optimization of a Catalytic Electrophilic
 Cyclopropanation without Diazomethane
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              180
_journal_paper_doi               10.1021/acs.organomet.6b00531
_journal_volume                  36
_journal_year                    2017
_chemical_formula_moiety         'C30 H47 B F3 P Pd'
_chemical_formula_sum            'C30 H47 B F3 P Pd'
_chemical_formula_weight         612.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.386(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9955(10)
_cell_length_b                   10.3337(6)
_cell_length_c                   18.7133(12)
_cell_measurement_reflns_used    3771
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      4.53
_cell_volume                     2898.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23002
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         4.784
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms high brilliance'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  0.7340
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0942 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.9121.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         6663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0171P)^2^+1.3013P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4834
_reflns_number_total             6663
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00531_si_002.cif
_cod_data_source_block           c080216_1_1_0m
_cod_database_code               4087008
_shelxl_version_number           2014/6
_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.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C4(H4), C18(H18), C20(H20), C19(H19), C6(H6)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C30(H30A,H30B,H30C), C25(H25A,H25B,H25C), C28(H28A,H28B,
 H28C), C12(H12A,H12B,H12C), C24(H24A,H24B,H24C), C29(H29A,H29B,H29C), C10(H10A,
 H10B,H10C), C26(H26A,H26B,H26C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C),
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              77501
_shelx_hkl_checksum              85685
_olex2_date_sample_data_collection 2016-02-08
_olex2_date_sample_submission    2016-02-05
_olex2_submission_original_sample_id c080216_1_1
_olex2_submission_special_instructions 'No special instructions were received'