Engineering Catalysts for Selective Ester Hydrogenation
Dub, Pavel A.; Batrice, Rami J.; Gordon, John C.; Scott, Brian L.; Minko, Yury; Schmidt, Jurgen G.; Williams, Robert F.; Organic Process Research & Development  (2020) –; doi:10.1021/acs.oprd.9b00559

data_1557358
_publ_section_title
;
 Engineering Catalysts for Selective Ester Hydrogenation
;
_journal_name_full               'Organic Process Research &amp; Development'
_journal_paper_doi               10.1021/acs.oprd.9b00559
_journal_year                    2020
_chemical_formula_moiety         'C35 H37 Cl2 N P2 Ru S, C H2 Cl2'
_chemical_formula_sum            'C36 H39 Cl4 N P2 Ru S'
_chemical_formula_weight         822.55
_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
_audit_creation_date             2020-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                72.8430(10)
_cell_angle_beta                 74.2730(10)
_cell_angle_gamma                73.6430(10)
_cell_formula_units_Z            2
_cell_length_a                   10.4094(9)
_cell_length_b                   13.8550(11)
_cell_length_c                   13.8759(11)
_cell_measurement_reflns_used    4025
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      24.33
_cell_measurement_theta_min      2.26
_cell_volume                     1795.8(3)
_computing_cell_refinement       'APEX2 V.2014.7-1 (Bruker AXS, 2014)'
_computing_data_collection       'APEX2 V.2014.7-1 (Bruker AXS, 2014)'
_computing_data_reduction        'SAINT, v. 8.34A (Bruker AXS, 2013)'
_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    'SHELXS 2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Quest with CMOS detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6690
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         2.337
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v. 2014/3 (Bruker AXS, 2013)'
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6690
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0236
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+3.5089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0576
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6564
_reflns_number_total             6690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            op9b00559_si_002.cif
_cod_data_source_block           dq0636
_cod_database_code               1557358
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.825
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9688(4)
 0.0312(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 Cl3-C36B \\sim Cl3-C36A \\sim Cl4A-C36A \\sim Cl4B-C36B
 with sigma of 0.008
4. Uiso/Uaniso restraints and constraints
Cl3 \\sim C36B \\sim C36A \\sim Cl4A \\sim Cl4B: within 2A with sigma of 0.002
and sigma for terminal atoms of 0.002
5. Others
 Sof(C36B)=Sof(H36A)=Sof(H36B)=Sof(Cl4B)=1-FVAR(1)
 Sof(C36A)=Sof(H36C)=Sof(H36D)=Sof(Cl4A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 N1(H1)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C36B(H36A,H36B),
 C36A(H36C,H36D)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
  C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32), C33(H33),
 C34(H34), C35(H35)
6.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              57597
_shelx_hkl_checksum              53032
_olex2_submission_special_instructions 'No special instructions were received'