Transition Metal-Free Direct Hydrogenation of Esters via a Frustrated Lewis Pair
Sapsford, Joshua S.; Csókás, Dániel; Turnell-Ritson, Roland C.; Parkin, Liam A.; Crawford, Andrew D.; Pápai, Imre; Ashley, Andrew E.; ACS Catalysis  (2021) 9143–9150; doi:10.1021/acscatal.1c01940

data_4518944
_publ_section_title
;
 Transition Metal-Free Direct Hydrogenation of Esters via a Frustrated
 Lewis Pair
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              9143
_journal_page_last               9150
_journal_paper_doi               10.1021/acscatal.1c01940
_journal_year                    2021
_chemical_formula_moiety         '0.25(C44 H84 F24 N4 O16 S8 Sn4)'
_chemical_formula_sum            'C11 H21 F6 N O4 S2 Sn'
_chemical_formula_weight         528.10
_space_group_crystal_system      tetragonal
_space_group_IT_number           142
_space_group_name_Hall           '-I 4bd 2c'
_space_group_name_H-M_alt        'I 41/a c d :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   16.7483(4)
_cell_length_b                   16.7483(4)
_cell_length_c                   28.9201(7)
_cell_measurement_reflns_used    5117
_cell_measurement_temperature    172.95(10)
_cell_measurement_theta_max      26.1240
_cell_measurement_theta_min      2.9240
_cell_volume                     8112.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details
;
  1 omega  -80.00    4.00   1.0000    1.7900
omega____ theta____ kappa____ phi______ frames
    -      -13.1782  -57.0000   60.0000 84

  2 omega  -52.00   40.00   1.0000    1.7900
omega____ theta____ kappa____ phi______ frames
    -       14.4282  -77.0000 -150.0000 92

  3 omega  -11.00   81.00   1.0000    1.7900
omega____ theta____ kappa____ phi______ frames
    -       14.4282   77.0000  -30.0000 92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0376090000
_diffrn_orient_matrix_UB_12      0.0108217000
_diffrn_orient_matrix_UB_13      0.0093823000
_diffrn_orient_matrix_UB_21      -0.0180923000
_diffrn_orient_matrix_UB_22      0.0063233000
_diffrn_orient_matrix_UB_23      0.0218704000
_diffrn_orient_matrix_UB_31      0.0072385000
_diffrn_orient_matrix_UB_32      -0.0404503000
_diffrn_orient_matrix_UB_33      0.0059223000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            21697
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.271
_diffrn_reflns_theta_min         2.809
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.533
_exptl_absorpt_correction_T_max  0.729
_exptl_absorpt_correction_T_min  0.564
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_description       plate
_exptl_crystal_F_000             4192
_exptl_crystal_preparation
'Reaction of tetraisopropyl tin and triflimidic acid in chloroform'
_exptl_crystal_recrystallization_method
'crystallised from chloroform layered with pentane'
_exptl_crystal_size_max          0.5171
_exptl_crystal_size_mid          0.4833
_exptl_crystal_size_min          0.2545
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0341P)^2^+26.1354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1633
_reflns_number_total             2359
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01940_si_001.cif
_cod_data_source_block           ash1608
_cod_original_cell_volume        8112.2(4)
_cod_original_sg_symbol_H-M      'I 41/a c d'
_cod_database_code               4518944
_chemical_oxdiff_formula         'C11 H21 F6 N O4 S2 Sn'
_reflns_odcompleteness_completeness 99.46
_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. Others
 Fixed Sof: C7(0.5) H5A(0.5) H5B(0.5) H5C(0.5) C6(0.5) H6A(0.5) H6B(0.5)
 H6C(0.5) C5(0.5) H7(0.5)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H7)
3.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C7(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_shelx_shelxl_version_number     2014/7
_ins_header
;
TITL ASH1608 in I4(1)/acd 
REM I4(1)/acd (#142 in standard setting)
CELL 0.71073  16.748289  16.748289  28.920095  90.0000  90.0000  90.0000
ZERR   16.00   0.000359   0.000359   0.000727   0.0000   0.0000   0.0000
LATT  2
SYMM -x+1/2,-y, z+1/2 
SYMM -y+1/4, x+3/4, z+1/4 
SYMM  y+1/4,-x+1/4, z+3/4 
SYMM -x+1/2, y,-z 
SYMM  x,-y,-z+1/2 
SYMM  y+1/4, x+3/4,-z+3/4 
SYMM -y+1/4,-x+1/4,-z+1/4 
SFAC C H N O F S Sn
UNIT 176.00 336.00 16.00 64.00 96.00 32.00 16.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2016-03-09
_olex2_exptl_crystal_mounting_method
'mounted on a glass fibre using polyfluoroether oil'
_olex2_submission_original_sample_id ASH1608
_olex2_submission_special_instructions 'No special instructions were received'