Expanding Ligand Space: Preparation, Characterization, and Synthetic Applications of Air-Stable, Odorless Di-tert-alkylphosphine Surrogates
Barber, Thomas; Argent, Stephen P.; Ball, Liam T.; ACS Catalysis  (2020) 5454–5461; doi:10.1021/acscatal.0c01414

data_4517611
_publ_section_title
;
 Expanding Ligand Space: Preparation, Characterization, and Synthetic
 Applications of Air-Stable, Odorless Di-tert-alkylphosphine Surrogates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              5454
_journal_page_last               5461
_journal_paper_doi               10.1021/acscatal.0c01414
_journal_year                    2020
_chemical_formula_moiety         'C F3 O3 S, C20 H32 P'
_chemical_formula_sum            'C21 H32 F3 O3 P S'
_chemical_formula_weight         452.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.488(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.1508(2)
_cell_length_b                   18.5177(4)
_cell_length_c                   21.1099(5)
_cell_measurement_reflns_used    14742
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.5280
_cell_measurement_theta_min      3.1660
_cell_volume                     4286.10(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -67.00  26.00   1.00    7.50    --  -43.06  57.00 -90.00   93
  2  \w   -115.00 -13.00   1.00    7.50    --  -43.06 -77.00  60.00  102
  3  \w      1.00  82.00   1.00    7.50    --   43.06 -99.00-120.00   81
  4  \w     23.00  96.00   1.00    7.50    --   43.06-125.00-180.00   73
  5  \w     30.00  90.00   1.00   30.00    --  103.00 -30.00   0.00   60
  6  \w     31.00 133.00   1.00   30.00    --  103.00 -77.00 -60.00  102
  7  \w     30.00  90.00   1.00   30.00    --  103.00 -30.00 -30.00   60
  8  \w     34.00  98.00   1.00   30.00    --  103.00 -45.00  60.00   64
  9  \w     30.00  90.00   1.00   30.00    --  103.00 -30.00-150.00   60
 10  \w     30.00  90.00   1.00   30.00    --  103.00 -30.00  90.00   60
 11  \w     31.00 118.00   1.00   30.00    --  103.00-125.00-120.00   87
 12  \w     94.00 175.00   1.00   30.00    --  103.00 125.00   0.00   81
 13  \w     19.00 112.00   1.00    7.50    --   43.06  57.00 -60.00   93
 14  \w     20.00  97.00   1.00    7.50    --   43.06  38.00 150.00   77
 15  \w     13.00 115.00   1.00    7.50    --   43.06  77.00-180.00  102
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0064092000
_diffrn_orient_matrix_UB_12      0.0772267000
_diffrn_orient_matrix_UB_13      -0.0263524000
_diffrn_orient_matrix_UB_21      0.1396106000
_diffrn_orient_matrix_UB_22      -0.0004345000
_diffrn_orient_matrix_UB_23      0.0214767000
_diffrn_orient_matrix_UB_31      0.0140498000
_diffrn_orient_matrix_UB_32      -0.0309291000
_diffrn_orient_matrix_UB_33      -0.0660082000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            28854
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.761
_diffrn_reflns_theta_min         3.198
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    2.457
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       lath
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.043
_refine_diff_density_max         1.836
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     539
_refine_ls_number_reflns         8114
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0642
_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^)+(0.0818P)^2^+5.4969P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6782
_reflns_number_total             8114
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c01414_si_008.cif
_cod_data_source_block           vjmlbc
_cod_depositor_comments
'Adding full bibliography for 4517604--4517617.cif.'
_cod_database_code               4517611
_nottingham_internal_coll_name   VJMLBC
_nottingham_internal_coll_number 17804
_nottingham_internal_coll_client VJM/LB
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '7.50, 30.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   pczajb
_nottingham_internal_coll_date   02/08/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_user pczajb
_nottingham_internal_process_date 03/08/2018
_nottingham_internal_solution_user pczajb
_nottingham_internal_solution_date 04/08/2018
_nottingham_internal_refinement_user pczajb
_nottingham_internal_refinement_date 07/08/2018
_nottingham_internal_self_validation_user pczajb
_nottingham_internal_self_validation_date 07/08/2018
_nottingham_internal_validation_user pczajb
_nottingham_internal_validation_date 07/08/2018
_olex2_exptl_crystal_mounting_method 'in Fomblin film on a micromount'
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H32 F3 O3 P1 S1'
_chemical_oxdiff_usercomment
'VJMLBC #17804 GVA-1473 IN FOMBLIN FILM ON MICROMOUNT for TB/LB'
_reflns_odcompleteness_completeness 97.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 P1-H1B \\sim P1-H1A \\sim P2-H2D \\sim P2-H2C
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F5: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
F6: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4.a Ternary CH refined with riding coordinates:
 C5(H5), C5'(H5'), C7(H7), C8'(H8'), C10'(H10'), C012(H012), C25(H25),
 C25'(H25'), C27(H27), C27'(H27'), C29(H29), C29'(H29')
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2'(H2'A,H2'B), C3(H3A,H3B), C3'(H3'A,H3'B), C4(H4A,H4B),
 C4'(H4'A,H4'B), C6(H6A,H6B), C6'(H6'A,H6'B), C7'(H7'A,H7'B), C8(H8A,H8B),
 C9'(H9'A,H9'B), C10(H10A,H10B), C22(H22A,H22B), C22'(H22C,H22D), C23(H23A,
 H23B), C23'(H23C,H23D), C24(H24A,H24B), C24'(H24C,H24D), C26(H26A,H26B),
 C26'(H26C,H26D), C28(H28A,H28B), C28'(H28C,H28D), C30(H30A,H30B), C30'(H30C,
 H30D)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.790
_oxdiff_exptl_absorpt_empirical_full_min 0.677