Allenes for Versatile Iron-Catalyzed C-H Activation by Weak O-Coordination: Mechanistic Insights by Kinetics, Intermediate Isolation, and Computation.
Messinis, Antonis M.; Finger, Lars H.; Hu, Lianrui; Ackermann, Lutz; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c04837

data_4135115
_publ_section_title
;
 Allenes for Versatile Iron-Catalyzed C-H Activation by Weak
 O-Coordination: Mechanistic Insights by Kinetics, Intermediate Isolation,
 and Computation.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c04837
_journal_year                    2020
_chemical_formula_moiety         'C20 H41 Fe O P3'
_chemical_formula_sum            'C20 H41 Fe O P3'
_chemical_formula_weight         446.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.666(2)
_cell_length_b                   13.466(4)
_cell_length_c                   18.476(5)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.575
_cell_measurement_theta_min      2.817
_cell_volume                     2404.9(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            47524
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.599
_diffrn_reflns_theta_min         2.378
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  0.3236
_exptl_absorpt_correction_T_min  0.2865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1213 before and 0.0477 after correction. The Ratio of minimum to maximum transmission is 0.8854. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0242
_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^)+(0.0282P)^2^+1.0462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0625
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3152
_reflns_number_total             3517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c04837_si_001.cif
_cod_data_source_block           0643_cg_0m
_cod_original_cell_volume        2404.6(11)
_cod_database_code               4135115
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.773
_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. Others
 Fixed Sof: H5A(0.5) H5B(0.5) H5C(0.5) H15A(0.5) H15B(0.5) H15C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
3.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              89659
_shelx_hkl_checksum              1168
_olex2_submission_special_instructions 'No special instructions were received'