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_4517606
_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_absolute_configuration ad
_chemical_formula_moiety         'C30 H52 P, C F3 O3 S'
_chemical_formula_sum            'C31 H52 F3 O3 P S'
_chemical_formula_weight         592.75
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-11-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3620(2)
_cell_length_b                   16.8285(3)
_cell_length_c                   25.1572(5)
_cell_measurement_reflns_used    11668
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.6640
_cell_measurement_theta_min      4.3810
_cell_volume                     3116.76(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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     -5.00  38.00   1.00   10.00    --  -41.70  19.00-150.00   43
  2  \w      6.00  83.00   1.00   10.00    --   41.70 -99.00 -30.00   77
  3  \w     14.00 115.00   1.00   10.00    --   41.70  57.00 -60.00  101
  4  \w     97.00 178.00   1.00   40.00    --  104.36 125.00   0.00   81
  5  \w     22.00 106.00   1.00   40.00    --  104.36 -94.00 120.00   84
  6  \w     28.00  57.00   1.00   40.00    --  104.36 -30.00-150.00   29
  7  \w     28.00  57.00   1.00   40.00    --  104.36 -30.00-120.00   29
  8  \w     22.00 106.00   1.00   40.00    --  104.36 -94.00-180.00   84
  9  \w     76.00 178.00   1.00   40.00    --  104.36  30.00-150.00  102
 10  \w     79.00 177.00   1.00   40.00    --  104.36  45.00 150.00   98
 11  \w     31.00  72.00   1.00   40.00    --  104.36 -45.00  90.00   41
 12  \w   -114.00 -66.00   1.00   10.00    --  -41.70-142.00 -33.00   48
 13  \w     14.00 115.00   1.00   10.00    --   41.70  57.00  90.00  101
 14  \w     17.00 116.00   1.00   10.00    --   41.70  38.00-150.00   99
 15  \w     27.00  52.00   1.00   40.00    --  104.36  11.00  11.00   25
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas 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      0.0075598000
_diffrn_orient_matrix_UB_12      -0.0086385000
_diffrn_orient_matrix_UB_13      -0.0609357000
_diffrn_orient_matrix_UB_21      -0.0291791000
_diffrn_orient_matrix_UB_22      -0.0902804000
_diffrn_orient_matrix_UB_23      0.0054341000
_diffrn_orient_matrix_UB_31      -0.2070216000
_diffrn_orient_matrix_UB_32      0.0124954000
_diffrn_orient_matrix_UB_33      -0.0029786000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18408
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.886
_diffrn_reflns_theta_min         3.514
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    1.807
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.683
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details
;
 Flack x determined using 2225 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         6075
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0666
_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^)+(0.1196P)^2^+1.3633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1796
_refine_ls_wR_factor_ref         0.1837
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                5759
_reflns_number_total             6075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c01414_si_004.cif
_cod_data_source_block           tbltbu2
_cod_depositor_comments
'Adding full bibliography for 4517604--4517617.cif.'
_cod_database_code               4517606
_nottingham_internal_coll_name   TBLTBU
_nottingham_internal_coll_number 18354
_nottingham_internal_coll_client TB/LTB
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '10.00, 40.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   02/09/2019
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 05/09/2019
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 05/09/2019
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 14/11/2019
_nottingham_internal_refinement_user pczspa
_nottingham_internal_validation_date 14/11/2019
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 14/11/2019
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C31H52F3O3PS
_chemical_oxdiff_usercomment
'TBLTBU2 #18354 GVB-1693 IN FOMBLIN FILM ON A MICROMOUNT FOR TB/LTB'
_reflns_odcompleteness_completeness 99.91
_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
 At 1.5 times of:
  All C(H,H,H) groups, All P(H,H) groups
2. Restrained distances
 P1-H1A \\sim P1-H1B
 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C4(H4), C8(H8), C11(H11), C19(H19), C23(H23), C26(H26)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
 C24(H24A,H24B), C25(H25A,H25B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B)
3.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C12(H12A,H12B,H12C),
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C27(H27A,H27B,
 H27C)
;
_shelx_res_checksum              59952
_shelx_hkl_checksum              31655
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 1.642
_oxdiff_exptl_absorpt_empirical_full_min 0.609