Formation of an imidazoliumyl-substituted [(LC)4P4]4+ tetracation and transition metal mediated fragmentation and insertion reaction (LC = NHC)
Weigand, Jan J.; Schwedtmann, Kai; Haberstroh, Jan; Roediger, Sven; Hennersdorf, Felix; Frontera, Antonio; Bauza, Antonio; Chemical Science  (2019) –; doi:10.1039/C9SC01701A

data_1551172
_publ_section_title
;
 Formation of an imidazoliumyl-substituted [(LC)4P4]4+ tetracation and
 transition metal mediated fragmentation and insertion reaction (LC = NHC)
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01701A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H40 Cl3 N4 P2, C F3 O3 S, C H2 Cl2'
_chemical_formula_sum            'C24 H42 Cl5 F3 N4 O3 P2 S'
_chemical_formula_weight         762.86
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2019-04-06 deposited with the CCDC.    2019-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.51562(4)
_cell_length_b                   10.67077(3)
_cell_length_c                   29.25903(9)
_cell_measurement_reflns_used    27969
_cell_measurement_temperature    102(1)
_cell_measurement_theta_max      76.5170
_cell_measurement_theta_min      3.0170
_cell_volume                     3595.37(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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      102(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    -64.00  31.00   0.50    2.00    --  -38.50  57.00 -30.00  190
  2  \w     24.00  51.00   0.50    2.00    --   42.62  38.00-180.00   54
  3  \w     44.00 136.00   0.50    8.00    --  111.00 -61.00 -90.00  184
  4  \w     92.00 120.00   0.50    8.00    --  111.00-125.00 -60.00   56
  5  \w     95.00 121.00   0.50    8.00    --  111.00-125.00  30.00   52
  6  \w     67.00  94.00   0.50    8.00    --  111.00 -94.00  30.00   54
  7  \w     73.00 108.00   0.50    8.00    --  111.00 -94.00 -30.00   70
  8  \w     92.00 130.00   0.50    8.00    --  111.00 -45.00  60.00   76
  9  \w    131.00 156.00   0.50    8.00    --  111.00 -15.00  60.00   50
 10  \w    150.00 177.00   0.50    8.00    --  111.00  15.00 -30.00   54
 11  \w    101.00 177.00   0.50    8.00    --  111.00  45.00-120.00  152
 12  \w    108.00 149.00   0.50    8.00    --  111.00 125.00-180.00   82
 13  \w     95.00 178.00   0.50    8.00    --  111.00 125.00 -90.00  166
 14  \w     87.00 173.00   0.50    8.00    --  111.00  45.00   0.00  172
 15  \w    144.00 171.00   0.50    8.00    --  111.00 125.00 120.00   54
 16  \w     70.00 143.00   0.50    8.00    --  111.00  15.00 -30.00  146
 17  \w     84.00 114.00   0.50    8.00    --  111.00 -15.00  60.00   60
 18  \w     44.00  87.00   0.50    8.00    --  111.00 -45.00  60.00   86
 19  \w     38.00  66.00   0.50    8.00    --  111.00 -30.00 -30.00   56
 20  \w     40.00 111.00   0.50    8.00    --  111.00 -77.00-120.00  142
 21  \w     74.00 102.00   0.50    8.00    --  111.00-125.00-150.00   56
 22  \w     62.00 109.00   0.50    8.00    --  111.00 -94.00-180.00   94
 23  \w     70.00 105.00   0.50    8.00    --  111.00 -30.00-180.00   70
 24  \w     38.00  84.00   0.50    8.00    --  111.00 -77.00-150.00   92
 25  \w     53.00  87.00   0.50    8.00    --  111.00-125.00-180.00   68
 26  \w     40.00 121.00   0.50    8.00    --  111.00-125.00-120.00  162
 27  \w     33.00  64.00   0.50    8.00    --  111.00 -15.00  60.00   62
 28  \w     34.00  61.00   0.50    8.00    --  111.00 -94.00 -30.00   54
 29  \w     32.00  78.00   0.50    8.00    --  111.00 -94.00  60.00   92
 30  \w     41.00 120.00   0.50    8.00    --  111.00-125.00 120.00  158
 31  \w     76.00 118.00   0.50    8.00    --  111.00-125.00 150.00   84
 32  \w    -63.00  32.00   0.50    2.00    --  -38.50  57.00-150.00  190
 33  \w    -74.00  -2.00   0.50    2.00    --  -38.50 125.00 -30.00  144
 34  \w    -94.00 -65.00   0.50    2.00    --  -38.50 125.00 -90.00   58
 35  \w   -108.00 -14.00   0.50    2.00    --  -38.50 -57.00  60.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0031066000
_diffrn_orient_matrix_UB_12      -0.0036789000
_diffrn_orient_matrix_UB_13      0.0526355000
_diffrn_orient_matrix_UB_21      0.1337679000
_diffrn_orient_matrix_UB_22      -0.0006016000
_diffrn_orient_matrix_UB_23      -0.0012570000
_diffrn_orient_matrix_UB_31      0.0007621000
_diffrn_orient_matrix_UB_32      0.1442574000
_diffrn_orient_matrix_UB_33      0.0013017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            38748
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.739
_diffrn_reflns_theta_min         3.021
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.475
_exptl_absorpt_correction_T_max  0.713
_exptl_absorpt_correction_T_min  0.347
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.381(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         7373
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0210
_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^)+(0.0364P)^2^+0.8768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0579
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                7366
_reflns_number_total             7373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01701a2.cif
_cod_data_source_block           5OTf
_cod_original_cell_volume        3595.366(18)
_cod_database_code               1551172
_chemical_oxdiff_formula         'C96 Cl12 F24 N16 O24 P8 S8 '
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.619(10) 0.381(10)
2. 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
3.a Ternary CH refined with riding coordinates:
 C6(H6), C9(H9), C17(H17), C20(H20)
3.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C),
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_shelx_res_checksum              13701
_shelx_shelxl_version_number     2014/7
_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 1.304
_oxdiff_exptl_absorpt_empirical_full_min 0.775