Regio- and Stereoselective Synthesis of Highly Functionalized Tetrasubstituted Olefins by Iodine-Mediated Iodofunctionalization of Ferrocene-Containing Allenylphosphonates.
Guo, Le; Gao, Yanpeng; Wang, Zishuo; Li, Zhi; Zhang, Yingjie; Wang, Haidong; Chen, Xihui; Gong, Zhenbo; Chen, Shufeng; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00762

data_4038397
_publ_section_title
;
 Regio- and Stereoselective Synthesis of Highly Functionalized
 Tetrasubstituted Olefins by Iodine-Mediated Iodofunctionalization of
 Ferrocene-Containing Allenylphosphonates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00762
_journal_year                    2020
_chemical_formula_moiety         'C28 H26 Fe I O5 P'
_chemical_formula_sum            'C28 H26 Fe I O5 P'
_chemical_formula_weight         656.21
_chemical_name_systematic        guo_1
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                94.414(5)
_cell_angle_beta                 106.298(5)
_cell_angle_gamma                107.793(5)
_cell_formula_units_Z            2
_cell_length_a                   9.5507(5)
_cell_length_b                   12.2508(8)
_cell_length_c                   14.2643(8)
_cell_measurement_reflns_used    4086
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5870
_cell_measurement_theta_min      3.2180
_cell_volume                     1500.91(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -19.00  86.00   1.00    2.50    --   16.96  19.00  60.00  105
  2  \w     13.00  46.00   1.00    2.50    --   16.96 -77.00   0.00   33
  3  \w    -22.00  57.00   1.00    2.50    --   16.96 -99.00 120.00   79
  4  \w    -50.00  35.00   1.00    2.50    --   16.96 -57.00-120.00   85
  5  \w    -24.00  23.00   1.00    2.50    --  -17.59 -99.00-120.00   47
  6  \w     52.00  88.00   1.00    2.50    --   16.96 178.00 -90.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0002091000
_diffrn_orient_matrix_UB_12      -0.0531569000
_diffrn_orient_matrix_UB_13      0.0165687000
_diffrn_orient_matrix_UB_21      -0.0488054000
_diffrn_orient_matrix_UB_22      0.0064826000
_diffrn_orient_matrix_UB_23      0.0278508000
_diffrn_orient_matrix_UB_31      -0.0663137000
_diffrn_orient_matrix_UB_32      -0.0308359000
_diffrn_orient_matrix_UB_33      -0.0414935000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11866
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.260
_diffrn_reflns_theta_min         3.024
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull yellowish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.998
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0434P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5184
_reflns_number_total             6785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00762_si_002.cif
_cod_data_source_block           exp_4569
_cod_original_cell_volume        1500.91(16)
_cod_database_code               4038397
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.738
_shelx_estimated_absorpt_t_min   0.738
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_shelx_res_checksum              60282
_shelx_hkl_checksum              19816
_shelx_fab_checksum              83951
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.727