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_7704779
_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 H42 N O P2 Ru, C Cl2, C F3 O3 S'
_chemical_formula_sum            'C41 H42 Cl2 F3 N O4 P2 Ru S'
_chemical_formula_weight         935.72
_chemical_properties_physical    Air-sensitive
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-18
_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                90
_cell_angle_beta                 92.2812(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.27473(16)
_cell_length_b                   15.7066(2)
_cell_length_c                   25.7096(4)
_cell_measurement_reflns_used    13837
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0720
_cell_measurement_theta_min      3.2750
_cell_volume                     4145.75(11)
_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      100.00(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 0.983
_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   -105.00 -10.00   1.00    5.00    --  -37.09 -77.00-180.00   95
  2  \w    -90.00  -2.00   1.00    5.00    --  -37.09 125.00  90.00   88
  3  \w    -90.00  -2.00   1.00    5.00    --  -37.09 125.00  30.00   88
  4  \w   -108.00  -8.00   1.00    5.00    --  -37.09 -19.00-150.00  100
  5  \w    -30.00  64.00   1.00    5.00    --   37.09 -77.00-150.00   94
  6  \w     20.00 104.00   1.00    5.00    --   37.09  57.00   0.00   84
  7  \w     18.00 106.00   1.00    5.00    --   37.09  38.00  60.00   88
  8  \w     23.00  90.00   1.00    5.00    --   37.09-125.00-120.00   67
  9  \w    -32.00  56.00   1.00    5.00    --   37.09 -38.00-150.00   88
 10  \w      1.00  76.00   1.00    5.00    --   37.09 -99.00 150.00   75
 11  \w     90.00 178.00   1.00   30.00    --  111.00  30.00 150.00   88
 12  \w     40.00 149.00   1.00   30.00    --  111.00 -15.00  90.00  109
 13  \w     43.00 128.00   1.00   30.00    --  111.00 -45.00 120.00   85
 14  \w    100.00 178.00   1.00   30.00    --  111.00 111.00-150.00   78
 15  \w     42.00 109.00   1.00   30.00    --  111.00 -94.00 -30.00   67
 16  \w     43.00 128.00   1.00   30.00    --  111.00 -45.00-150.00   85
 17  \w     42.00 109.00   1.00   30.00    --  111.00 -94.00 -90.00   67
 18  \w     93.00 178.00   1.00   30.00    --  111.00  61.00 -90.00   85
 19  \w    -56.00  32.00   1.00    5.00    --  -37.09  38.00  30.00   88
 20  \w     10.00 105.00   1.00    5.00    --   37.09  77.00 -90.00   95
 21  \w     10.00  82.00   1.00    5.00    --   37.09  77.00  30.00   72
 22  \w     20.00 104.00   1.00    5.00    --   37.09  57.00 120.00   84
;
_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      0.0636448000
_diffrn_orient_matrix_UB_12      -0.0002299000
_diffrn_orient_matrix_UB_13      0.0552973000
_diffrn_orient_matrix_UB_21      -0.1333270000
_diffrn_orient_matrix_UB_22      0.0188375000
_diffrn_orient_matrix_UB_23      0.0228227000
_diffrn_orient_matrix_UB_31      -0.0263028000
_diffrn_orient_matrix_UB_32      -0.0962442000
_diffrn_orient_matrix_UB_33      0.0042955000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            31977
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.240
_diffrn_reflns_theta_min         3.298
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.915
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.589
_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    1.499
_exptl_crystal_description       needle
_exptl_crystal_F_000             1912
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pentane, dichloromethane'
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.016
_refine_diff_density_max         2.258
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         8168
_refine_ls_number_restraints     267
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0742
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1048P)^2^+22.0279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1997
_refine_ls_wR_factor_ref         0.2066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7147
_reflns_number_total             8168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt00786b3.cif
_cod_data_source_block           complex_2
_cod_depositor_comments
'Adding full bibliography for 7704777--7704780.cif.'
_cod_original_cell_volume        4145.77(11)
_cod_database_code               7704779
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C41H42Cl2F3NO4P2RuS
_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
2. Restrained distances
 Cl2-C41 \\sim Cl1A-C41A
 with sigma of 0.02
 Cl1-C41 \\sim Cl2A-C41A
 with sigma of 0.02
 Cl2-Cl1 \\sim Cl1A-Cl2A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
S1 \\sim F1 \\sim F2 \\sim F3 \\sim O2 \\sim O3 \\sim O4 \\sim C40 \\sim S1A
\\sim F1A \\sim F2A \\sim F3A \\sim O2A \\sim O3A \\sim O4A \\sim C40A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Cl1A \\sim Cl2A \\sim C41A \\sim Cl1 \\sim Cl2 \\sim C41: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(S1A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=Sof(C40A)=1-
 FVAR(1)
 Sof(S1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(O2)=Sof(O3)=Sof(O4)=Sof(C40)=FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C41A)=1-FVAR(2)
 Sof(Cl1)=Sof(Cl2)=Sof(C41)=FVAR(2)
5.a Free rotating group:
 S1(F1,F2,F3,O2,O3,O4,C40), S1A(F1A,F2A,F3A,O2A,O3A,O4A,C40A)
5.b Ternary CH refined with riding coordinates:
 C3(H3)
5.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C12(H12A,H12B), C13(H13A,
 H13B), C14(H14A,H14B), C15(H15A,H15B)
5.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), 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)
;
_shelx_res_checksum              97103
_olex2_date_sample_data_collection 2019-01-17
_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 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.769