Mechanochemistry for facilitated access to N,N-diaryl NHC metal complexes
Beillard, Audrey; Bantreil, Xavier; Métro, Thomas-Xavier; Martinez, Jean; Lamaty, Frédéric; New J. Chem. 41 (2017) 1057–; doi:10.1039/C6NJ02895K

data_7055915
_publ_section_title
;
 Mechanochemistry for facilitated access to N,N-diaryl NHC metal complexes
;
_journal_issue                   3
_journal_name_full               'New J. Chem.'
_journal_page_first              1057
_journal_paper_doi               10.1039/C6NJ02895K
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C23 H31 N2, Cl'
_chemical_formula_sum            'C23 H31 Cl N2'
_chemical_formula_weight         370.95
_chemical_name_systematic
'1,3-Bis(2,4,6-trimethylphenyl)-4,5-trans-dimethyl]imidazolidinium chloride'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_audit_update_record
;
2016-06-24 deposited with the CCDC.
2016-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.137(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9790(3)
_cell_length_b                   15.1223(5)
_cell_length_c                   15.7117(8)
_cell_measurement_reflns_used    4275
_cell_measurement_temperature    175
_cell_measurement_theta_max      51.6960
_cell_measurement_theta_min      4.0900
_cell_volume                     2100.08(15)
_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    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      175
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0143
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -17.00  52.00   1.00    1.00    --    0.00  57.00  60.00   69
  2  \w    -20.00  71.00   1.00    1.00    --    0.00  38.00 -30.00   91
  3  \w    -71.00  22.00   1.00    1.00    --    0.00 -38.00   0.00   93
  4  \w    -19.00  67.00   1.00    1.00    --    0.00  57.00 150.00   86
  5  \w     83.00 127.00   1.00   13.00    --   67.56  77.00-120.00   44
  6  \w     97.00 135.00   1.00   13.00    --   67.56 126.00 -30.00   38
  7  \w     82.00 135.00   1.00   13.00    --   67.56  77.00 -30.00   53
  8  \w     39.00  72.00   1.00   13.00    --   67.56  77.00-180.00   33
  9  \w     39.00  69.00   1.00   13.00    --   67.56  77.00-120.00   30
 10  \w     82.00 124.00   1.00   13.00    --   67.56  77.00-180.00   42
 11  \w      4.00  86.00   1.00   13.00    --   67.56 -77.00  30.00   82
 12  \w     39.00  69.00   1.00   13.00    --   67.56  77.00 150.00   30
 13  \w     87.00 134.00   1.00   13.00    --   67.56  77.00 150.00   47
 14  \w     16.00  96.00   1.00   13.00    --   67.56 -77.00 120.00   80
 15  \w     39.00  67.00   1.00   13.00    --   67.56  77.00-150.00   28
 16  \w     87.00 133.00   1.00   13.00    --   67.56  77.00  90.00   46
 17  \w    103.00 132.00   1.00   13.00    --   67.56 126.00-150.00   29
 18  \w     83.00 133.00   1.00   13.00    --   67.56  77.00-150.00   50
 19  \w     40.00  73.00   1.00   13.00    --   67.56  77.00 120.00   33
 20  \w     83.00 136.00   1.00   13.00    --   67.56  77.00 120.00   53
 21  \w     39.00  67.00   1.00   13.00    --   67.56  77.00   0.00   28
 22  \w     82.00 120.00   1.00   13.00    --   67.56  77.00   0.00   38
 23  \w     39.00  77.00   1.00   13.00    --   67.56  77.00  60.00   38
 24  \w     83.00 127.00   1.00   13.00    --   67.56  77.00  60.00   44
 25  \w     39.00  75.00   1.00   13.00    --   67.56  77.00 -60.00   36
 26  \w     78.00 136.00   1.00   13.00    --   67.56  77.00 -60.00   58
 27  \w     39.00  68.00   1.00   13.00    --   67.56  77.00 -90.00   29
 28  \w     88.00 133.00   1.00   13.00    --   67.56  77.00 -90.00   45
 29  \w     39.00  67.00   1.00   13.00    --   67.56  77.00  30.00   28
 30  \w     90.00 126.00   1.00   13.00    --   67.56  77.00  30.00   36
 31  \w      8.00  88.00   1.00   13.00    --   67.56 -61.00 -90.00   80
 32  \w     39.00  69.00   1.00   13.00    --   67.56  77.00  90.00   30
 33  \w     23.00 122.00   1.00   13.00    --   67.56-126.00 -60.00   99
 34  \w     39.00  65.00   1.00   13.00    --   67.56  77.00 -30.00   26
;
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1361775000
_diffrn_orient_matrix_UB_12      -0.0559143000
_diffrn_orient_matrix_UB_13      0.0154846000
_diffrn_orient_matrix_UB_21      0.0075299000
_diffrn_orient_matrix_UB_22      -0.0533795000
_diffrn_orient_matrix_UB_23      -0.0826576000
_diffrn_orient_matrix_UB_31      0.1085604000
_diffrn_orient_matrix_UB_32      -0.0663219000
_diffrn_orient_matrix_UB_33      0.0534126000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.104
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4293
_diffrn_reflns_theta_full        51.583
_diffrn_reflns_theta_max         51.776
_diffrn_reflns_theta_min         4.089
_exptl_absorpt_coefficient_mu    1.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             799.994
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0241
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3655
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.0004448
_refine_ls_shift/su_mean         0.0000436
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 22.3 19.3 19.5 8.24 -0.737
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0720
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0709
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              15
_reflns_limit_l_min              -15
_reflns_number_gt                3655
_reflns_number_total             1954
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.01
_oxford_diffrn_Wilson_scale      0.29
_oxford_refine_ls_r_factor_ref   0.0678
_oxford_refine_ls_scale          5.244(18)
_oxford_reflns_number_all        4291
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_twin_special_details
;
Component 2 rotated by -179.8005\%
 around [1.00 0.00 -0.00] (reciprocal) or [1.00 0.00 0.10] (direct)
;
_cod_data_source_file            c6nj02895k2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7055915.cif.'
_cod_original_cell_volume        2100.08(11)
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               7055915
_cell_oxdiff_length_a            8.9789(5)
_cell_oxdiff_length_b            15.1251(9)
_cell_oxdiff_length_c            15.7108(10)
_cell_oxdiff_angle_alpha         90.016(5)
_cell_oxdiff_angle_beta          100.174(5)
_cell_oxdiff_angle_gamma         90.037(5)
_cell_oxdiff_volume              2100.1(2)
_oxdiff_exptl_absorpt_empirical_full_min 0.799
_oxdiff_exptl_absorpt_empirical_full_max 1.426
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_twin_items               2
_oxdiff_twin_integration_method  simultaneous
_solvent_exptl_crystal_recrystallization_method
'Dichloromethane - diethyl ether'