Expanding the chemical space of enol silyl ethers: catalytic dicarbofunctionalization enabled by iron catalysis.
Sar, Dinabandhu; Yin, Shuai; Grygus, Jacob; Rentería-Gómez, Ángel; Garcia, Melanie; Gutierrez, Osvaldo; Chemical science 14 (2023) 13007–13013; doi:10.1039/d3sc04549h

data_1570159
_publ_section_title
;
 Expanding the chemical space of enol silyl ethers: catalytic
 dicarbofunctionalization enabled by iron catalysis.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              13007
_journal_page_last               13013
_journal_paper_doi               10.1039/d3sc04549h
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C20 H22 F2 O4'
_chemical_formula_sum            'C20 H22 F2 O4'
_chemical_formula_weight         364.37
_chemical_name_systematic
'tert-butyl 2,2-difluoro-3-hydroxy-3-phenylpropanoate'
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-10
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-05-03 deposited with the CCDC.	2023-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                67.082(3)
_cell_angle_beta                 73.561(3)
_cell_angle_gamma                80.326(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4592(6)
_cell_length_b                   11.1811(9)
_cell_length_c                   12.5405(10)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    110.00
_cell_measurement_theta_max      70.284
_cell_measurement_theta_min      3.942
_cell_volume                     921.98(13)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      110.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Venture (PHOTON III)'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13544
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.282
_diffrn_reflns_theta_min         3.942
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  0.4684
_exptl_absorpt_correction_T_min  0.3684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0853 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.7865.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0318P)^2^+0.3357P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3253
_reflns_number_total             3493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04549h2.cif
_cod_data_source_block           ds276
_cod_depositor_comments
'Adding full bibliography for 1570159--1570162.cif.'
_cod_database_code               1570159
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.904
_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, All O(H) groups
2. Restrained distances
 O2-C13 \\sim O2A-C13
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O2 \\sim C13 \\sim O2A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 O2, C13, O2A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Others
 Sof(H13a)=Sof(O2A)=Sof(H2Aa)=1-FVAR(1)
 Sof(O2)=Sof(H2)=Sof(H13)=FVAR(1)
6.a Riding coordinates:
 O2A(H2Aa)
6.b Ternary CH refined with riding coordinates:
 C13(H13), C13(H13a)
6.c Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
6.d Aromatic/amide H refined with riding coordinates:
 C2(H2a), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
6.e Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C19(H19a,H19b,H19c), C20(H20a,H20b,H20c)
6.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              69324
_olex2_submission_special_instructions 'No special instructions were received'