Reactivity of Ferrocenyl Phosphates Bearing (Hetero-)Aromatics and [3]Ferrocenophanes toward Anionic Phospho-Fries Rearrangements
Korb, Marcus; Lehrich, Steve W.; Lang, Heinrich; The Journal of Organic Chemistry  (2017) –; doi:10.1021/acs.joc.7b00030

data_4032360
_publ_section_title
;
 Reactivity of Ferrocenyl Phosphates Bearing (Hetero-)Aromatics and
 [3]Ferrocenophanes toward Anionic Phospho-Fries Rearrangements
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00030
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C31 H23 Fe O4 P, C H Cl3'
_chemical_formula_sum            'C32 H24 Cl3 Fe O4 P'
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_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
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_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
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_cell_measurement_reflns_used    3280
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      120.00(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
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_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
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_diffrn_reflns_number            8885
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.150
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
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_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81669
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1791 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.012(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0431P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0965
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                4778
_reflns_number_total             5412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00030_si_001.cif
_cod_data_source_block           MK-458-A
_cod_database_code               4032360
_shelxl_version_number           2013-4
_shelx_res_checksum              30442
_shelx_hkl_checksum              92459