Selective Double Carbomagnesiation of Internal Alkynes Catalyzed by Iron-N-Heterocyclic Carbene Complexes: A Convenient Method to Highly Substituted 1,3-Dienyl Magnesium Reagents.
Liu, Yuesheng; Wang, Lijun; Deng, Liang; Journal of the American Chemical Society 138 (2016) 112–115; doi:10.1021/jacs.5b12522

data_4129984
_publ_section_title
;
 Selective Double Carbomagnesiation of Internal Alkynes Catalyzed by
 Iron-N-Heterocyclic Carbene Complexes: A Convenient Method to Highly
 Substituted 1,3-Dienyl Magnesium Reagents.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              112
_journal_page_last               115
_journal_paper_doi               10.1021/jacs.5b12522
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C29 H35 I'
_chemical_formula_sum            'C29 H35 I'
_chemical_formula_weight         510.47
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.935(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4002(18)
_cell_length_b                   8.8803(9)
_cell_length_c                   18.069(2)
_cell_measurement_reflns_used    2362
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.669
_cell_measurement_theta_min      2.27
_cell_volume                     2551.9(5)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18175
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         2.272
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.267
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0549 before and 0.0446 after correction.
The Ratio of minimum to maximum transmission is 0.9077.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0774P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1408
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2932
_reflns_number_total             5000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b12522_si_002.cif
_cod_data_source_block           15
_cod_database_code               4129984
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.863
_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:
 C6(H6), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C25(H25), C26(H26),
 C27(H27), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_shelx_res_checksum              43557
_shelx_hkl_checksum              60064
_olex2_submission_special_instructions 'No special instructions were received'