Synthesis and applications of 1-iodo-4-MgCl-1,3-dienes and 1-iodovinyl phenylmagnesium chlorides
Wei, Junnian; Zhang, Yongliang; Zhang, Wen-Xiong; Xi, Zhenfeng; Org. Chem. Front. 1 (2014) 983–; doi:10.1039/C4QO00191E

data_1553026
_publ_section_title
;
 Synthesis and applications of 1-iodo-4-MgCl-1,3-dienes and 1-iodovinyl
 phenylmagnesium chlorides
;
_journal_issue                   8
_journal_name_full               'Org. Chem. Front.'
_journal_page_first              983
_journal_paper_doi               10.1039/C4QO00191E
_journal_volume                  1
_journal_year                    2014
_chemical_formula_moiety         'C27 H30 B O2 P'
_chemical_formula_sum            'C27 H30 B O2 P'
_chemical_formula_weight         428.29
_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             2014-05-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4844)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.227(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.9068(5)
_cell_length_b                   34.826(2)
_cell_length_c                   20.4959(11)
_cell_measurement_reflns_used    970
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      56.4610
_cell_measurement_theta_min      3.2990
_cell_volume                     4900.9(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
  1 omega  -21.00   34.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8556   38.0000 -120.0000 55

  2 omega  -50.00  -19.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8556   38.0000  120.0000 31

  3 omega -112.00  -14.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8556  -57.0000  -30.0000 98

  4 omega    3.00   68.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8556  -99.0000  -90.0000 65

  5 omega   33.00   87.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000  -60.0000 54

  6 omega   38.00   78.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000 -150.0000 40

  7 omega   95.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775 -125.0000  150.0000 26

  8 omega   94.00  145.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  125.0000  -30.0000 51

  9 omega   67.00  107.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775 -125.0000 -120.0000 40

 10 omega   94.00  120.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  125.0000 -120.0000 26

 11 omega   84.00  172.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   45.0000  -30.0000 88

 12 omega   41.00  139.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -77.0000   30.0000 98
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0137785000
_diffrn_orient_matrix_UB_12      0.0244988000
_diffrn_orient_matrix_UB_13      -0.0629204000
_diffrn_orient_matrix_UB_21      -0.0036458000
_diffrn_orient_matrix_UB_22      -0.0368436000
_diffrn_orient_matrix_UB_23      -0.0417803000
_diffrn_orient_matrix_UB_31      -0.2237970000
_diffrn_orient_matrix_UB_32      -0.0009246000
_diffrn_orient_matrix_UB_33      -0.0036340000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1321
_diffrn_reflns_av_unetI/netI     0.2448
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19191
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.203
_diffrn_reflns_theta_min         4.340
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         9652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.2312
_refine_ls_R_factor_gt           0.0928
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0003P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.2427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3216
_reflns_number_total             9652
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4qo00191e2.cif
_cod_data_source_block           14mar24b
_cod_original_cell_volume        4901.0(5)
_cod_database_code               1553026
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C20 H20 B P O2'
_chemical_oxdiff_usercomment     wjn-FLP
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C2B(H2B), C3(H3), C3B(H3B), C4(H4), C4B(H4B), C5(H5), C5B(H5B),
 C8(H8), C8B(H8B), C11(H11), C11B(H11B), C12(H12), C12B(H12B), C13(H13),
 C13B(H13B), C14(H14), C14B(H14B), C15(H15), C15B(H15B), C17(H17), C17B(H17B),
 C18(H18), C18B(H18B), C19(H19), C19B(H19B), C20(H20), C20B(H20B), C21(H21),
 C21B(H21B)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9B(H9BA,H9BB,H9BC), C24(H24A,H24B,H24C), C24B(H24D,H24E,
 H24F), C25(H25A,H25B,H25C), C25B(H25D,H25E,H25F), C26(H26A,H26B,H26C),
 C26B(H26D,H26E,H26F), C27(H27A,H27B,H27C), C27B(H27D,H27E,H27F)
;
_shelx_res_checksum              12975
_olex2_submission_special_instructions 'No special instructions were received'