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_4517607
_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, C14 H28 P'
_chemical_formula_sum            'C15 H28 F3 O3 P S'
_chemical_formula_weight         376.40
_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
_audit_creation_date             2018-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.595(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5000(2)
_cell_length_b                   10.6274(2)
_cell_length_c                   18.6029(4)
_cell_measurement_reflns_used    4042
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.7770
_cell_measurement_theta_min      4.7980
_cell_volume                     1846.13(7)
_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 0.989
_diffrn_measured_fraction_theta_max 0.955
_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     18.00 112.00   1.00    1.50    --   42.12  57.00  90.00   94
  2  \w    -27.00  63.00   1.00    1.50    --   42.12 -57.00 -60.00   90
  3  \w     83.00 116.00   1.00    6.00    --  103.32-125.00 -30.00   33
  4  \w     30.00  55.00   1.00    6.00    --  103.32 -30.00  60.00   25
  5  \w     34.00 124.00   1.00    6.00    --  103.32 -61.00 -60.00   90
  6  \w    139.00 171.00   1.00    6.00    --  103.32  45.00  90.00   32
  7  \w     35.00  94.00   1.00    6.00    --  103.32 -45.00  90.00   59
  8  \w     96.00 171.00   1.00    6.00    --  103.32 125.00   0.00   75
  9  \w     83.00 120.00   1.00    6.00    --  103.32  45.00  90.00   37
;
_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      -0.0101261000
_diffrn_orient_matrix_UB_12      0.1280928000
_diffrn_orient_matrix_UB_13      -0.0393713000
_diffrn_orient_matrix_UB_21      0.0742870000
_diffrn_orient_matrix_UB_22      -0.0565866000
_diffrn_orient_matrix_UB_23      -0.0595112000
_diffrn_orient_matrix_UB_31      -0.1471566000
_diffrn_orient_matrix_UB_32      -0.0372357000
_diffrn_orient_matrix_UB_33      -0.0446791000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6454
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         73.576
_diffrn_reflns_theta_min         4.813
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    2.735
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.631
_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
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       column
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.118
_refine_diff_density_max         1.044
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3553
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0521P)^2^+2.6965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1341
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3178
_reflns_number_total             3553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c01414_si_009.cif
_cod_data_source_block           vjmlbd
_cod_depositor_comments
'Adding full bibliography for 4517604--4517617.cif.'
_cod_database_code               4517607
_nottingham_internal_coll_name   VJMLBD
_nottingham_internal_coll_number 17805
_nottingham_internal_coll_client VJM/LB
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '6.00, 1.50'
_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 06/08/2018
_nottingham_internal_self_validation_user pczajb
_nottingham_internal_self_validation_date 06/08/2018
_nottingham_internal_validation_user pczajb
_nottingham_internal_validation_date 06/08/2018
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H28 F3 O3 P1 S1'
_chemical_oxdiff_usercomment
'VJMLBD #17805 GVA-1471 in Fomblin film on MicroMount for TB/LB'
_reflns_odcompleteness_completeness 99.03
_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, All P(H,H) groups
2. Restrained distances
 P1-H1P \\sim P1-H2P
 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C3'(H3'A,H3'B), C4(H4A,H4B), C4'(H4'A,H4'B), C5(H5A,H5B),
 C5'(H5'A,H5'B), C6(H6A,H6B), C6'(H6'A,H6'B), C7(H7A,H7B), C7'(H7'A,H7'B)
3.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2'(H2'A,H2'B,H2'C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.205
_oxdiff_exptl_absorpt_empirical_full_min 0.842