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_4517616
_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         'C10 H24 P, C F3 O3 S'
_chemical_formula_sum            'C11 H24 F3 O3 P S'
_chemical_formula_weight         324.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_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                90.0
_cell_angle_beta                 99.9348(18)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   17.4780(3)
_cell_length_b                   10.4898(2)
_cell_length_c                   17.7113(4)
_cell_measurement_reflns_used    6533
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.6360
_cell_measurement_theta_min      3.2610
_cell_volume                     3198.51(11)
_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      '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 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.949
_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   -114.00 -26.00   1.00    1.50    --  -43.06 -38.00  90.00   88
  2  \w   -101.00 -27.00   1.00    1.50    --  -43.06 -38.00   0.00   74
  3  \w     58.00  95.00   1.00    6.00    --  103.00-125.00  30.00   37
  4  \w     30.00  88.00   1.00    6.00    --  103.00 -30.00-180.00   58
  5  \w     29.00 110.00   1.00    6.00    --  103.00 -94.00 120.00   81
  6  \w     84.00 174.00   1.00    6.00    --  103.00  30.00  90.00   90
  7  \w     30.00  89.00   1.00    6.00    --  103.00 -30.00 -90.00   59
  8  \w     32.00  90.00   1.00    6.00    --  103.00 -30.00 120.00   58
;
_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      -0.0281229000
_diffrn_orient_matrix_UB_12      0.0050418000
_diffrn_orient_matrix_UB_13      -0.0872995000
_diffrn_orient_matrix_UB_21      0.0781722000
_diffrn_orient_matrix_UB_22      -0.0558477000
_diffrn_orient_matrix_UB_23      -0.0130395000
_diffrn_orient_matrix_UB_31      -0.0332761000
_diffrn_orient_matrix_UB_32      -0.1357591000
_diffrn_orient_matrix_UB_33      0.0020670000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11217
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.786
_diffrn_reflns_theta_min         3.281
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    3.067
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.598
_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_density_diffrn    1.347
_exptl_crystal_description       lath
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0477P)^2^+0.5119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0902
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5270
_reflns_number_total             6130
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c01414_si_011.cif
_cod_data_source_block           vjmlbf
_cod_depositor_comments
'Adding full bibliography for 4517604--4517617.cif.'
_cod_database_code               4517616
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H24 F3 O3 P1 S1'
_chemical_oxdiff_usercomment
'VJMLBF #17807 GVA-1472 IN FOMBLIN FILM ON MICROMOUNT for TB/LB'
_cell_oxdiff_angle_alpha         90.026(3)
_cell_oxdiff_angle_beta          99.963(3)
_cell_oxdiff_angle_gamma         90.038(2)
_cell_oxdiff_length_a            17.4778(5)
_cell_oxdiff_length_b            10.4883(3)
_cell_oxdiff_length_c            17.7156(6)
_cell_oxdiff_measurement_reflns_used 6533
_cell_oxdiff_volume              3198.51(17)
_reflns_odcompleteness_completeness 98.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C4'(H4'A,H4'B), C24(H24A,H24B), C24'(H24C,H24D)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2'(H2'A,H2'B,H2'C), C3(H3A,H3B,H3C), C3'(H3'A,H3'B,H3'C),
 C5(H5A,H5B,H5C), C5'(H5'A,H5'B,H5'C), C22(H22A,H22B,H22C), C22'(H22D,H22E,
 H22F), C23(H23A,H23B,H23C), C23'(H23D,H23E,H23F), C25(H25A,H25B,H25C),
 C25'(H25D,H25E,H25F)
;
_nottingham_internal_coll_client VJM/LB
_nottingham_internal_coll_date   02/08/2018
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '6.00, 1.50'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_name   VJMLBF
_nottingham_internal_coll_number 17807
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_user   pczajb
_nottingham_internal_process_date 03/08/2018
_nottingham_internal_process_user pczajb
_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 1.383
_oxdiff_exptl_absorpt_empirical_full_min 0.748