A Readily Accessible Chiral NNN Pincer Ligand with a Pyrrole Backbone and Its Ni(II) Chemistry: Syntheses, Structural Chemistry, and Bond Activations.
Wenz, Jan; Kochan, Alexander; Wadepohl, Hubert; Gade, Lutz H.; Inorganic chemistry 56 (2017) 3631–3643; doi:10.1021/acs.inorgchem.7b00077

data_4345584
_publ_section_title
;
 A Readily Accessible Chiral NNN Pincer Ligand with a Pyrrole Backbone and
 Its Ni(II) Chemistry: Syntheses, Structural Chemistry, and Bond
 Activations.
;
_journal_issue                   6
_journal_name_full               'Inorganic chemistry'
_journal_page_first              3631
_journal_page_last               3643
_journal_paper_doi               10.1021/acs.inorgchem.7b00077
_journal_volume                  56
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H38 F N3 Ni O2'
_chemical_formula_sum            'C28 H38 F N3 Ni O2'
_chemical_formula_weight         526.32
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      76
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_jw23
_audit_creation_date             2016-01-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
'04.02.2016 11:52:41 CET UTC+01:00  encif 1.38'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.07080(3)
_cell_length_b                   15.07080(3)
_cell_length_c                   12.09666(5)
_cell_measurement_reflns_used    67053
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.5870
_cell_measurement_theta_min      5.5230
_cell_volume                     2747.502(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41p (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41p (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41p (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
'encif (Wadepohl, 2009-15); encifer 1.5 (CCDC, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_environment      perfluoro
_diffrn_ambient_temperature      120(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -30.00  70.00   1.00    1.00    --    0.00  77.00 -30.00  100
  2  \w    -21.00  69.00   1.00    1.00    --    0.00  57.00 150.00   90
  3  \w    -72.00  26.00   1.00    1.00    --    0.00 -38.00-150.00   98
  4  \w    -21.00  69.00   1.00    1.00    --    0.00  57.00 120.00   90
  5  \w    -72.00  26.00   1.00    1.00    --    0.00 -38.00   0.00   98
  6  \w    -34.00   0.00   1.00    1.00    --   22.00 123.00-158.54   34
  7  \w     -9.00  18.00   1.00    2.00    --   34.00 101.00  77.87   27
  8  \w     -9.00  18.00   1.00    2.00    --   34.00 102.00  46.57   27
  9  \w     -2.00  24.00   1.00    2.00    --   38.00  96.00  22.74   26
 10  \w      6.00  34.00   1.00    2.00    --   42.00  87.00  -2.53   28
 11  \w      7.00  35.00   1.00    2.00    --   42.00  86.00  74.42   28
 12  \w     12.00  38.00   1.00    2.00    --   46.00  84.00 -90.88   26
 13  \w     13.00  40.00   1.00    2.00    --   46.00  83.00-143.31   27
 14  \w     17.00  45.00   1.00    2.00    --   50.00  82.00 153.78   28
 15  \w     18.00  46.00   1.00    2.00    --   50.00  80.00 -23.70   28
 16  \w     17.00  45.00   1.00    2.00    --   50.00  82.00 119.69   28
 17  \w     19.00  47.00   1.00    2.00    --   50.00  79.00 -49.90   28
 18  \w     24.00 124.00   1.00    2.00    --   54.00  77.00 150.00  100
 19  \w     24.00 124.00   1.00    2.00    --   54.00  77.00  30.00  100
 20  \w     24.00 124.00   1.00    2.00    --   54.00  77.00 -30.00  100
 21  \w      1.00  96.00   1.00    2.00    --   54.00 -99.00  60.00   95
 22  \w     24.00 124.00   1.00    2.00    --   54.00  77.00  60.00  100
 23  \w     24.00 124.00   1.00    2.00    --   54.00  77.00 112.50  100
 24  \w     24.00 124.00   1.00    2.00    --   54.00  77.00   0.00  100
 25  \w    -15.00  75.00   1.00    2.00    --   54.00 -57.00 -90.00   90
 26  \w     23.00  49.00   1.00    2.00    --   54.00  78.00 121.02   26
 27  \w     24.00 124.00   1.00    2.00    --   54.00  77.00-120.00  100
 28  \w     24.00 124.00   1.00    2.00    --   54.00  77.00  90.00  100
 29  \w      1.00  96.00   1.00    2.00    --   54.00 -99.00-180.00   95
 30  \w     29.00 128.00   1.00    2.00    --   58.00  76.00  86.81   99
 31  \w     36.00 126.00   1.00    2.00    --   58.00  62.00 157.24   90
 32  \w     31.00 127.00   1.00    2.00    --   58.00  72.00 -73.68   96
 33  \w     28.00 128.00   1.00    2.00    --   58.00  77.00 -98.22  100
 34  \w     29.00 128.00   1.00    2.00    --   58.00  76.00-111.84   99
 35  \w     31.00 127.00   1.00    2.00    --   58.00  72.00 -43.95   96
 36  \w     28.00 128.00   1.00    2.00    --   58.00  77.00  11.37  100
 37  \w     32.00 132.00   1.00    2.00    --   62.00  77.00 178.95  100
 38  \w     33.00 132.00   1.00    2.00    --   62.00  76.00-159.82   99
 39  \w     32.00 132.00   1.00    2.00    --   62.00  77.00  61.79  100
 40  \w     34.00 131.00   1.00    2.00    --   62.00  73.00 -88.77   97
 41  \w     38.00 130.00   1.00    2.00    --   62.00  67.00  47.85   92
 42  \w     40.00 130.00   1.00    2.00    --   62.00  63.00  -9.41   90
 43  \w     34.00 132.00   1.00    2.00    --   62.00  74.00-113.55   98
 44  \w     39.00 135.00   1.00    2.00    --   66.00  71.00 149.40   96
 45  \w     43.00 134.00   1.00    2.00    --   66.00  65.00  90.87   91
 46  \w     41.00 140.00   1.00    2.00    --   70.00  76.00-175.75   99
 47  \w     47.00 138.00   1.00    2.00    --   70.00  65.00-114.77   91
 48  \w     43.00 138.00   1.00    2.00    --   70.00  72.00  12.43   95
 49  \w     49.00  89.00   1.00    2.00    --   70.00  44.00 125.01   40
 50  \w     56.00  83.00   1.00    2.00    --   74.00  51.00  82.72   27
 51  \w     52.00 125.00   1.00    2.00    --   74.00  50.00-165.07   73
 52  \w    110.00 141.00   1.00    2.00    --   74.00  59.00 -14.69   31
 53  \w     55.00 107.00   1.00    2.00    --   74.00  59.00 -14.69   52
 54  \w     57.00  82.00   1.00    2.00    --   74.00  51.00 -13.10   25
 55  \w     54.00 145.00   1.00    2.00    --   78.00  67.00 -91.97   91
 56  \w     55.00  81.00   1.00    2.00    --   78.00  67.00-130.36   26
 57  \w    122.00 150.00   1.00    8.00    --   82.00  72.00  28.01   28
 58  \w     56.00  84.00   1.00    8.00    --   82.00  72.00  28.01   28
 59  \w     56.00  83.00   1.00    8.00    --   82.00  71.00 -64.94   27
 60  \w     65.00  92.00   1.00    8.00    --   82.00  60.00 -41.72   27
 61  \w     60.00  88.00   1.00    8.00    --   82.00  50.00  45.92   28
 62  \w     55.00 139.00   1.00    8.00    --   82.00  73.00-120.85   84
 63  \w     57.00 106.00   1.00    8.00    --   82.00  39.00 164.81   49
 64  \w     60.00  86.00   1.00    8.00    --   86.00  70.00  86.26   26
 65  \w     58.00  84.00   1.00    8.00    --   86.00  74.00-134.50   26
 66  \w     59.00  91.00   1.00    8.00    --   86.00  72.00 179.90   32
 67  \w     56.00  82.00   1.00    8.00    --   86.00  77.00 -93.64   26
 68  \w     62.00 119.00   1.00    8.00    --   90.00  73.00 166.48   57
 69  \w     61.00 112.00   1.00    8.00    --   90.00  76.00-171.50   51
 70  \w     71.00 111.00   1.00    8.00    --   98.00  71.00-108.97   40
 71  \w     78.00 104.00   1.00    8.00    --  108.00  77.00 -30.00   26
 72  \w     85.00 112.00   1.00    8.00    --  108.00  64.00 -90.00   27
 73  \w     86.00 175.00   1.00    8.00    --  108.00  64.00 150.00   89
 74  \w     84.00 177.00   1.00    8.00    --  108.00  38.00  30.00   93
 75  \w     37.00 105.00   1.00    8.00    --  108.00-111.00  30.00   68
 76  \w     86.00 174.00   1.00    8.00    --  108.00  64.00-150.00   88
 77  \w     83.00 144.00   1.00    8.00    --  108.00  38.00  60.00   61
 78  \w     86.00 149.00   1.00    8.00    --  108.00  64.00-180.00   63
 79  \w     83.00 165.00   1.00    8.00    --  108.00  38.00 -30.00   82
 80  \w     84.00 164.00   1.00    8.00    --  108.00  38.00 120.00   80
 81  \w     86.00 111.00   1.00    8.00    --  108.00  64.00  90.00   25
 82  \w     85.00 175.00   1.00    8.00    --  108.00  64.00  60.00   90
 83  \w    123.00 149.00   1.00    8.00    --  108.00  77.00   0.00   26
 84  \w     78.00 105.00   1.00    8.00    --  108.00  77.00   0.00   27
 85  \w     39.00 137.00   1.00    8.00    --  108.00 -77.00  30.00   98
 86  \w     86.00 115.00   1.00    8.00    --  108.00  64.00   0.00   29
 87  \w     42.00 130.00   1.00    8.00    --  108.00 -64.00-120.00   88
 88  \w    134.00 160.00   1.00    8.00    --  108.00  64.00 -60.00   26
 89  \w     85.00 123.00   1.00    8.00    --  108.00  64.00 -60.00   38
 90  \w     36.00 114.00   1.00    8.00    --  108.00-111.00-150.00   78
 91  \w    102.00 172.00   1.00    8.00    --  108.00 111.00 -30.00   70
 92  \w     79.00 105.00   1.00    8.00    --  108.00  77.00 150.00   26
 93  \w    150.00 176.00   1.00    8.00    --  108.00  77.00  30.00   26
 94  \w     79.00 104.00   1.00    8.00    --  108.00  77.00  30.00   25
 95  \w     85.00 111.00   1.00    8.00    --  108.00  64.00 -30.00   26
 96  \w    151.00 177.00   1.00    8.00    --  108.00  77.00-150.00   26
 97  \w     78.00 105.00   1.00    8.00    --  108.00  77.00-150.00   27
 98  \w     85.00 174.00   1.00    8.00    --  108.00  64.00 120.00   89
 99  \w    112.00 177.00   1.00    8.00    --  108.00  77.00 -90.00   65
100  \w     79.00  93.00   1.00    8.00    --  108.00-111.00 -60.00   14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0793029000
_diffrn_orient_matrix_UB_12      -0.0624167000
_diffrn_orient_matrix_UB_13      -0.0203873000
_diffrn_orient_matrix_UB_21      0.0639184000
_diffrn_orient_matrix_UB_22      -0.0795388000
_diffrn_orient_matrix_UB_23      -0.0075943000
_diffrn_orient_matrix_UB_31      -0.0090040000
_diffrn_orient_matrix_UB_32      -0.0149464000
_diffrn_orient_matrix_UB_33      0.1254656000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            77007
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.723
_diffrn_reflns_theta_min         3.654
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.300
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41p (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details
;
 Flack x determined using 2313 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5089
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0161
_refine_ls_R_factor_gt           0.0161
_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^)+(0.0313P)^2^+0.2539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0441
_refine_ls_wR_factor_ref         0.0441
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5088
_reflns_number_total             5089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic7b00077_si_002.cif
_cod_data_source_block           ga_jw23
_cod_original_cell_volume        2747.502(15)
_cod_database_code               4345584
_audit_block_refno               2635
_audit_block_usercomment         'jw421, irregular, yellow'
_chemical_oxdiff_formula         'C28 H38 F N3 Ni O2'
_chemical_oxdiff_usercomment     'jw421, irregular, yellow'
_shelx_estimated_absorpt_t_max   0.881
_shelx_estimated_absorpt_t_min   0.881
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelxl_version_number           2014/7
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.3907(8) 0.6093(8)
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:
 C1(H1), C12(H12), C13(H13), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C24(H24), C25(H25), C27(H27), C28(H28)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,
 H22B,H22C)
;
_shelx_res_checksum              78100
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.184
_oxdiff_exptl_absorpt_empirical_full_min 0.865
_cell_oxdiff_length_a            15.06625(16)
_cell_oxdiff_length_b            15.07340(15)
_cell_oxdiff_length_c            12.09823(17)
_cell_oxdiff_angle_alpha         90.0057(10)
_cell_oxdiff_angle_beta          90.0073(10)
_cell_oxdiff_angle_gamma         90.0023(8)
_cell_oxdiff_volume              2747.50(6)
_cell_oxdiff_measurement_reflns_used 67053