Product inhibition in nucleophilic aromatic substitution through DPPPent-supported π-arene catalysis.
Mueller, Benjamin R. J.; Schley, Nathan D.; Dalton transactions (Cambridge, England : 2003) 49 (2020) 10114–10119; doi:10.1039/d0dt00786b

data_7704780
_publ_section_title
;
 Product inhibition in nucleophilic aromatic substitution through
 DPPPent-supported \p-arene catalysis.
;
_journal_issue                   29
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10114
_journal_page_last               10119
_journal_paper_doi               10.1039/d0dt00786b
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C39 H44 N O P2 Ru, C F3 O3 S, 0.5(C4 H8 O)'
_chemical_formula_sum            'C42 H48 F3 N O4.5 P2 Ru S'
_chemical_formula_weight         890.88
_chemical_properties_physical    Air-sensitive
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-22 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                75.1534(18)
_cell_angle_beta                 86.1993(16)
_cell_angle_gamma                78.7339(16)
_cell_formula_units_Z            4
_cell_length_a                   9.87358(18)
_cell_length_b                   16.3420(3)
_cell_length_c                   26.1572(6)
_cell_measurement_reflns_used    20203
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.9840
_cell_measurement_theta_min      2.8400
_cell_volume                     4000.47(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_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    -54.00  30.00   1.00    8.00    --  -37.19  57.00-120.00   84
  2  \w   -106.00 -18.00   1.00    8.00    --  -37.19 -38.00 150.00   88
  3  \w    -64.00  30.00   1.00    8.00    --  -37.19  77.00-120.00   94
  4  \w   -106.00  32.00   1.00    8.00    --  -37.19   0.00  30.00  138
  5  \w    -54.00  30.00   1.00    8.00    --  -37.19  57.00  30.00   84
  6  \w   -105.00 -10.00   1.00    8.00    --  -37.19 -77.00 120.00   95
  7  \w     23.00  91.00   1.00    8.00    --   37.19-125.00  60.00   68
  8  \w     18.00 106.00   1.00    8.00    --   37.19  38.00-180.00   88
  9  \w     23.00  91.00   1.00    8.00    --   37.19-125.00 -60.00   68
 10  \w      8.00 109.00   1.00    8.00    --   37.19  19.00-180.00  101
 11  \w      1.00  76.00   1.00    8.00    --   37.19 -99.00 -60.00   75
 12  \w      1.00  76.00   1.00    8.00    --   37.19 -99.00-150.00   75
 13  \w     20.00 104.00   1.00    8.00    --   37.19  57.00  60.00   84
 14  \w     23.00  91.00   1.00    8.00    --   37.19-125.00 120.00   68
 15  \w     23.00  91.00   1.00    8.00    --   37.19-125.00 150.00   68
 16  \w     20.00 104.00   1.00    8.00    --   37.19  57.00 120.00   84
 17  \w     23.00  91.00   1.00    8.00    --   37.19-125.00  30.00   68
 18  \w     94.00 178.00   1.00   30.00    --  111.00  45.00-180.00   84
 19  \w     43.00 128.00   1.00   30.00    --  111.00 -45.00  30.00   85
 20  \w     42.00 109.00   1.00   30.00    --  111.00 -94.00 -30.00   67
 21  \w     84.00 178.00   1.00   30.00    --  111.00  77.00 -30.00   94
 22  \w     44.00 129.00   1.00   30.00    --  111.00 -61.00 -60.00   85
 23  \w     41.00 132.00   1.00   30.00    --  111.00 -30.00 120.00   91
 24  \w     41.00 116.00   1.00   30.00    --  111.00-111.00 -90.00   75
 25  \w     42.00 109.00   1.00   30.00    --  111.00 -94.00 150.00   67
 26  \w     42.00 109.00   1.00   30.00    --  111.00 -94.00  60.00   67
 27  \w     43.00 128.00   1.00   30.00    --  111.00 -45.00-120.00   85
 28  \w     94.00 178.00   1.00   30.00    --  111.00  45.00  60.00   84
 29  \w     41.00 132.00   1.00   30.00    --  111.00 -30.00   0.00   91
 30  \w     44.00 129.00   1.00   30.00    --  111.00 -61.00-180.00   85
 31  \w     94.00 178.00   1.00   30.00    --  111.00  45.00  30.00   84
 32  \w     41.00 116.00   1.00   30.00    --  111.00-111.00-150.00   75
 33  \w     73.00 178.00   1.00   30.00    --  111.00  15.00 -30.00  105
 34  \w   -105.00 -10.00   1.00    8.00    --  -37.19 -77.00 -60.00   95
 35  \w   -105.00 -10.00   1.00    8.00    --  -37.19 -77.00-150.00   95
 36  \w   -106.00  32.00   1.00    8.00    --  -37.19   0.00-150.00  138
 37  \w   -105.00 -10.00   1.00    8.00    --  -37.19 -77.00 -30.00   95
 38  \w   -105.00 -10.00   1.00    8.00    --  -37.19 -77.00-180.00   95
 39  \w   -105.00 -10.00   1.00    8.00    --  -37.19 -77.00-120.00   95
 40  \w   -105.00 -10.00   1.00    8.00    --  -37.19 -77.00  30.00   95
 41  \w     18.00 106.00   1.00    8.00    --   37.19  38.00 -30.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0376850000
_diffrn_orient_matrix_UB_12      -0.0116846000
_diffrn_orient_matrix_UB_13      0.0579765000
_diffrn_orient_matrix_UB_21      0.1522451000
_diffrn_orient_matrix_UB_22      0.0010740000
_diffrn_orient_matrix_UB_23      -0.0168857000
_diffrn_orient_matrix_UB_31      -0.0268272000
_diffrn_orient_matrix_UB_32      0.0985417000
_diffrn_orient_matrix_UB_33      -0.0081985000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            61031
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.397
_diffrn_reflns_theta_min         2.846
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.907
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.479
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_recrystallization_method
'Diffusion of pentane into crude reaction mixture'
_exptl_crystal_size_max          0.091
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.019
_refine_diff_density_max         1.313
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1089
_refine_ls_number_reflns         15810
_refine_ls_number_restraints     360
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0472P)^2^+6.0789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12548
_reflns_number_total             15810
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt00786b3.cif
_cod_data_source_block           complex_3
_cod_depositor_comments
'Adding full bibliography for 7704777--7704780.cif.'
_cod_original_cell_volume        4000.47(15)
_cod_original_formula_sum        'C42 H48 F3 N O4.50 P2 Ru S'
_cod_database_code               7704780
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C42H48F3NO4.5P2RuS
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 Ru(H) groups
2. Uiso/Uaniso restraints and constraints
O5 \\sim O5B \\sim C41 \\sim C41B \\sim C42 \\sim C42B \\sim C43 \\sim C43B
\\sim C44 \\sim C44B: within 2A with sigma of 0.02 and sigma for terminal atoms
of 0.04
S1B \\sim F1B \\sim F2B \\sim F3B \\sim O2B \\sim O3B \\sim O4B \\sim C40B
\\sim S1C \\sim F1C \\sim F2C \\sim F3C \\sim O2C \\sim O3C \\sim O4C \\sim
C40C: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
3. Others
 Sof(S1C)=Sof(F1C)=Sof(F2C)=Sof(F3C)=Sof(O2C)=Sof(O3C)=Sof(O4C)=Sof(C40C)=1-
 FVAR(1)
 Sof(S1B)=Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(O2B)=Sof(O3B)=Sof(O4B)=Sof(C40B)=
 FVAR(1)
 Sof(O5B)=Sof(C41B)=Sof(H41C)=Sof(H41D)=Sof(C42B)=Sof(H42C)=Sof(H42D)=
 Sof(C43B)=Sof(H43C)=Sof(H43D)=Sof(C44B)=Sof(H44C)=Sof(H44D)=1-FVAR(2)
 Sof(O5)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(C43)=
 Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=FVAR(2)
4.a Free rotating group:
 O5(C41,C42,C43,C44), O5B(C41B,C42B,C43B,C44B)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C7B(H7BA,H7BB),
  C8B(H8BA,H8BB), C9B(H9BA,H9BB), C10B(H10C,H10D), C11B(H11C,H11D), C12B(H12C,
 H12D), C13B(H13C,H13D), C14B(H14C,H14D), C15B(H15C,H15D), C41(H41A,H41B),
 C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C41B(H41C,H41D), C42B(H42C,
 H42D), C43B(H43C,H43D), C44B(H44C,H44D)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37),
 C38(H38), C39(H39), C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B),
 C17B(H17B), C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B), C23B(H23B),
 C24B(H24B), C25B(H25B), C26B(H26B), C27B(H27B), C29B(H29B), C30B(H30B),
 C31B(H31B), C32B(H32B), C33B(H33B), C35B(H35B), C36B(H36B), C37B(H37B),
 C38B(H38B), C39B(H39B)
;
_shelx_res_checksum              3506
_olex2_date_sample_data_collection 2019-04-29
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_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 1.146
_oxdiff_exptl_absorpt_empirical_full_min 0.886