Hydration of Cyanohydrins by Highly Active Cationic Pt Catalysts: Mechanism and Scope
Li, Chengcheng; Chang, Xiao-Yong; Huo, Luqiong; Tan, Haibo; Xing, Xiangyou; Xu, Chen; ACS Catalysis 11 (2021) 8716–8726; doi:10.1021/acscatal.1c02254

data_4518849
_publ_section_title
;
 Hydration of Cyanohydrins by Highly Active Cationic Pt Catalysts:
 Mechanism and Scope
;
_journal_issue                   14
_journal_name_full               'ACS Catalysis'
_journal_page_first              8716
_journal_page_last               8726
_journal_paper_doi               10.1021/acscatal.1c02254
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C36 H35 Fe O P3 Pt, 2(C F3 O3 S)'
_chemical_formula_sum            'C38 H35 F6 Fe O7 P3 Pt S2'
_chemical_formula_weight         1125.63
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                98.845(2)
_cell_angle_beta                 100.326(2)
_cell_angle_gamma                94.635(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3276(6)
_cell_length_b                   10.4475(7)
_cell_length_c                   21.4237(14)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.46
_cell_measurement_theta_min      2.61
_cell_volume                     2016.9(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            38576
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.499
_diffrn_reflns_theta_min         2.360
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.123
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0720 after correction.
The Ratio of minimum to maximum transmission is 0.6311.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_description       block
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         3.370
_refine_diff_density_min         -2.075
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     834
_refine_ls_number_reflns         10144
_refine_ls_number_restraints     1538
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0164P)^2^+10.6898P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9145
_reflns_number_total             10144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c02254_si_005.cif
_cod_data_source_block           cxy1532_0m
_cod_depositor_comments
'Adding full bibliography for 4518848--4518852.cif.'
_cod_database_code               4518849
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.464
_shelx_estimated_absorpt_t_min   0.352
_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, All O(H) groups
2. Restrained distances
 C43-C44 = C17-C12 = C43-C42 = C21-C12 = C42-C47 = C25-C21 = C46-C47 = C25-C22
 = C44-C45 = C34-C17 = C46-C45 = C22-C34
 1.39 with sigma of 0.02
 F1-C48 = F2-C48 = F3-C48 = F9-C50 = F7-C50 = F8-C50
 1.34 with sigma of 0.02
 S1-O2 = S3-O8 = S3-O9 = S3-O10 = S1-O4 = S1-O3
 1.44 with sigma of 0.02
 S2-C49
 1.83 with sigma of 0.02
 S2-O7 = S2-O5 = S2-O6
 1.44 with sigma of 0.02
 S3-C50 = S1-C48
 1.83 with sigma of 0.02
 F5-C49 = F6-C49 = F4-C49
 1.34 with sigma of 0.02
 C53-S6
 1.82 with sigma of 0.02
 C53-F16 = C53-F17 = C53-F18
 1.33 with sigma of 0.02
 S6-O17 = S6-O18 = S6-O19
 1.44 with sigma of 0.02
 C51-S4
 1.82 with sigma of 0.02
 S4-O11 = S4-O12 = S4-O13
 1.44 with sigma of 0.02
 C51-F10 = C51-F11 = C51-F12
 1.33 with sigma of 0.02
 C52-F13 = C52-F14 = C52-F15
 1.33 with sigma of 0.02
 C52-S5
 1.82 with sigma of 0.02
 S5-O14 = S5-O15 = S5-O16
 1.44 with sigma of 0.02
 O7-O5
 2.44 with sigma of 0.04
 F5-F6
 2.14 with sigma of 0.04
 O7-O6
 2.44 with sigma of 0.04
 C21-C22 = C42-C46 = C47-C45 = C34-C25
 2.42 with sigma of 0.04
 F6-F4
 2.14 with sigma of 0.04
 C50-O9
 2.56 with sigma of 0.04
 C50-O8
 2.56 with sigma of 0.04
 C48-O2
 2.56 with sigma of 0.04
 F5-F4
 2.14 with sigma of 0.04
 C50-O10
 2.56 with sigma of 0.04
 C48-O3
 2.56 with sigma of 0.04
 C48-O4
 2.56 with sigma of 0.04
 O6-O5
 2.44 with sigma of 0.04
 O9-O10
 2.44 with sigma of 0.04
 O10-O8
 2.44 with sigma of 0.04
 O9-O8
 2.44 with sigma of 0.04
 C51-O13
 2.57 with sigma of 0.04
 C53-O17
 2.58 with sigma of 0.04
 C53-O18
 2.56 with sigma of 0.04
 C51-O12
 2.56 with sigma of 0.04
 C53-O19
 2.57 with sigma of 0.04
 C51-O11
 2.58 with sigma of 0.04
 C52-O16
 2.57 with sigma of 0.04
 C52-O14
 2.58 with sigma of 0.04
 C52-O15
 2.56 with sigma of 0.04
 O11-O12 \\sim O12-O13 \\sim O11-O13
 with sigma of 0.04
 P4-C43 \\sim P3-C12
 with sigma of 0.02
 S4-F10 \\sim S4-F11 \\sim S4-F12
 with sigma of 0.04
 O17-O18 \\sim O18-O19 \\sim O17-O19
 with sigma of 0.04
 S6-F16 \\sim S6-F17 \\sim S6-F18
 with sigma of 0.04
 F16-F17 \\sim F17-F18 \\sim F18-F16
 with sigma of 0.04
 C53-F16 \\sim C53-F17 \\sim C53-F18
 with sigma of 0.02
 C53-O17 \\sim C53-O18 \\sim C53-O19
 with sigma of 0.04
 S6-O17 \\sim S6-O18 \\sim S6-O19
 with sigma of 0.02
 S4-O11 \\sim S4-O12 \\sim S4-O13
 with sigma of 0.02
 C51-O11 \\sim C51-O12 \\sim C51-O13
 with sigma of 0.04
 C51-F10 \\sim C51-F11 \\sim C51-F12
 with sigma of 0.02
 F10-F11 \\sim F11-F12 \\sim F12-F10
 with sigma of 0.04
 C52-O14 \\sim C52-O15 \\sim C52-O16
 with sigma of 0.04
 C52-F13 \\sim C52-F14 \\sim C52-F15
 with sigma of 0.02
 F13-F14 \\sim F14-F15 \\sim F15-F13
 with sigma of 0.04
 O14-O15 \\sim O15-O16 \\sim O14-O16
 with sigma of 0.04
 S5-F13 \\sim S5-F14 \\sim S5-F15
 with sigma of 0.04
 S5-O14 \\sim S5-O15 \\sim S5-O16
 with sigma of 0.02
3. Restrained planarity
 P4, C42, C43, C44, C45, C46, C47
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
S6 \\sim F16 \\sim F17 \\sim F18 \\sim O17 \\sim O18 \\sim O19 \\sim C53:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C4 \\sim C24 \\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C37 \\sim C38 \\sim
C39 \\sim C40 \\sim C41: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
S4 \\sim F10 \\sim F11 \\sim F12 \\sim O11 \\sim O12 \\sim O13 \\sim C51:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
S5 \\sim F13 \\sim F14 \\sim F15 \\sim O14 \\sim O15 \\sim O16 \\sim C52:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
S4 \\sim F10 \\sim F11 \\sim F12 \\sim O11 \\sim O12 \\sim O13 \\sim C51 \\sim
S5 \\sim F13 \\sim F14 \\sim F15 \\sim O14 \\sim O15 \\sim O16 \\sim C52 \\sim
S2 \\sim F4 \\sim F5 \\sim F6 \\sim O5 \\sim O6 \\sim O7 \\sim C49: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
S3 \\sim F7 \\sim F8 \\sim F9 \\sim O8 \\sim O9 \\sim O10 \\sim C50 \\sim S1
\\sim F1 \\sim F2 \\sim F3 \\sim O2 \\sim O3 \\sim O4 \\sim C48 \\sim S6 \\sim
F16 \\sim F17 \\sim F18 \\sim O17 \\sim O18 \\sim O19 \\sim C53: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(O4) = Uanis(O10)
Uanis(C50) = Uanis(C48)
Uanis(C12) = Uanis(C43)
Uanis(F2) = Uanis(F8)
Uanis(S3) = Uanis(S1)
Uanis(F1) = Uanis(F7)
Uanis(P3) = Uanis(P4)
Uanis(O9) = Uanis(O3)
Uanis(F9) = Uanis(F3)
Uanis(C45) = Uanis(C34)
Uanis(O2) = Uanis(O8)
Uanis(C47) = Uanis(C25)
Uanis(C46) = Uanis(C22)
Uanis(C21) = Uanis(C42)
Uanis(C44) = Uanis(C17)
Uanis(C24) = Uanis(C38)
5. Rigid body (RIGU) restrains
 S4, F10, F11, F12, O11, O12, O13, C51
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S6, F16, F17, F18, O17, O18, O19, C53
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S5, F13, F14, F15, O14, O15, O16, C52
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 1*[Sof(S2)+Sof(F4)+Sof(F5)+Sof(F6)+Sof(O5)+Sof(O6)+Sof(O7)+Sof(C49)]+1*
 [Sof(S4)+Sof(F10)+Sof(F11)+Sof(F12)+Sof(O11)+Sof(O12)+Sof(O13)+Sof(C51)]+1*
 [Sof(S5)+Sof(F13)+Sof(F14)+Sof(F15)+Sof(O14)+Sof(O15)+Sof(O16)+Sof(C52)]=1
 with esd of 0
 1*[Sof(S1)+Sof(F1)+Sof(F2)+Sof(F3)+Sof(O2)+Sof(O3)+Sof(O4)+Sof(C48)]+1*
 [Sof(S3)+Sof(F7)+Sof(F8)+Sof(F9)+Sof(O8)+Sof(O9)+Sof(O10)+Sof(C50)]+1*[Sof(S6)+
 Sof(F16)+Sof(F17)+Sof(F18)+Sof(O17)+Sof(O18)+Sof(O19)+Sof(C53)]=1 with esd of 0
 Sof(C37)=Sof(H37)=Sof(C38)=Sof(H38)=Sof(C39)=Sof(H39)=Sof(C40)=Sof(H40)=
 Sof(C41)=Sof(H41)=1-FVAR(1)
 Sof(C24)=Sof(H24)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=Sof(C28)=Sof(H28)=
 Sof(C29)=Sof(H29)=FVAR(1)
 Sof(P4)=Sof(C42)=Sof(H42)=Sof(C43)=Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=
 Sof(C46)=Sof(H46)=Sof(C47)=Sof(H47)=1-FVAR(2)
 Sof(P3)=Sof(C12)=Sof(C17)=Sof(H17)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=
 Sof(C25)=Sof(H25)=Sof(C34)=Sof(H34)=FVAR(2)
 Sof(S1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(O2)=Sof(O3)=Sof(O4)=Sof(C48)=FVAR(3)
 Sof(S2)=Sof(F4)=Sof(F5)=Sof(F6)=Sof(O5)=Sof(O6)=Sof(O7)=Sof(C49)=FVAR(4)
 Sof(S4)=Sof(F10)=Sof(F11)=Sof(F12)=Sof(O11)=Sof(O12)=Sof(O13)=Sof(C51)=FVAR(5)
 Sof(S5)=Sof(F13)=Sof(F14)=Sof(F15)=Sof(O14)=Sof(O15)=Sof(O16)=Sof(C52)=FVAR(6)
 Sof(S3)=Sof(F7)=Sof(F8)=Sof(F9)=Sof(O8)=Sof(O9)=Sof(O10)=Sof(C50)=FVAR(7)
 Sof(S6)=Sof(F16)=Sof(F17)=Sof(F18)=Sof(O17)=Sof(O18)=Sof(O19)=Sof(C53)=FVAR(8)
7.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C23(H23), C30(H30), C31(H31),
  C32(H32), C35(H35), C17(H17), C21(H21), C22(H22), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28), C29(H29), C34(H34), C37(H37), C38(H38), C39(H39),
  C40(H40), C41(H41), C42(H42), C44(H44), C45(H45), C46(H46), C47(H47)
7.b Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C36(H36A,H36B,H36C)
7.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              33343
_shelx_hkl_checksum              49842
_olex2_submission_special_instructions 'No special instructions were received'