Esterification of the Primary Benzylic C-H Bonds with Carboxylic Acids Catalyzed by Ionic Iron(III) Complexes Containing an Imidazolinium Cation.
Lu, Bing; Zhu, Fan; Sun, Hong-Mei; Shen, Qi; Organic letters 19 (2017) 1132–1135; doi:10.1021/acs.orglett.7b00148

data_1545272
_publ_section_title
;
 Esterification of the Primary Benzylic C-H Bonds with Carboxylic Acids
 Catalyzed by Ionic Iron(III) Complexes Containing an Imidazolinium
 Cation.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1132
_journal_page_last               1135
_journal_paper_doi               10.1021/acs.orglett.7b00148
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'Br4 Fe, C11 H23 N2'
_chemical_formula_sum            'C11 H23 Br4 Fe N2'
_chemical_formula_weight         558.80
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   15.3952(8)
_cell_length_b                   13.0190(6)
_cell_length_c                   38.748(2)
_cell_measurement_reflns_used    3958
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3350
_cell_measurement_theta_min      3.2970
_cell_volume                     7766.3(7)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1340
_diffrn_reflns_av_unetI/netI     0.1357
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            24584
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.94
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    8.997
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.26935
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light red'
_exptl_crystal_density_diffrn    1.910
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4296
_refine_diff_density_max         0.917
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         6817
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      0.894
_refine_ls_R_factor_all          0.1576
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1629
_reflns_number_gt                3142
_reflns_number_total             6817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00148_si_002.cif
_cod_data_source_block           g160422c
_cod_depositor_comments
;
         Adding full bibliography for 1545272.cif.

2019-02-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C22 H45 Br8 Fe2 N4 O0'
_cod_original_formula_weight         1116.60
_cod_original_formula_moiety         '2(Br4 Fe), 2(C11 H23 N2)'
_cod_original_formula_units_Z            8
_cod_original_cell_volume        7766.2(7)
_cod_database_code               1545272
_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. Restrained distances
 C6-C4
 1.52 with sigma of 0.02
3. Rigid bond restraints
 C6, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C7) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C7) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C13(H13A,H13B), C2(H2A,H2B), C3(H3A,H3B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C1(H1)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C18(H18A,H18B,
 H18C), C22(H22A,H22B,H22C), C17(H17A,H17B,H17C), C10(H10A,H10B,H10C), C5(H5A,
 H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C9(H9A,H9B,
 H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'