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_4345578
_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         'C22 H34 F N3 Ni O2'
_chemical_formula_sum            'C22 H34 F N3 Ni O2'
_chemical_formula_weight         450.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_jw14
_audit_creation_date
;
'Fri Jul 17 15:52:23 2015'
;
_audit_creation_method
;
Olex2 1.2
(compiled Dec 12 2016 15:58:59 for OlexSys, GUI svn.r5292)
;
_audit_update_record
'15.02.2017 12:32:03 CET UTC+01:00  encif 1.68'
_cell_angle_alpha                90
_cell_angle_beta                 111.120(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.06821(18)
_cell_length_b                   12.8272(2)
_cell_length_c                   10.32375(19)
_cell_measurement_reflns_used    18006
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      31.2770
_cell_measurement_theta_min      3.7120
_cell_volume                     1120.19(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
'encif (Wadepohl, 2009-17); encifer 1.5.2 (CCDC, 2016)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2014 (Giacovazzo et al., 2014)'
_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'
_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 0.996
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega    2.00   95.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   38.0000   60.0000 186

  2 omega   23.00   49.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -99.0000    0.0000 52

  3 omega  -20.00   69.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -99.0000  -90.0000 178

  4 omega  -45.00   32.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -38.0000    0.0000 154

  5 omega   -3.00   36.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000  -30.0000 78

  6 omega   -3.00   36.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000  120.0000 78

  7 omega  -42.00   44.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -57.0000  150.0000 172

  8 omega   57.00   95.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000   90.0000 76

  9 omega  -42.00   39.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -57.0000  -60.0000 162

 10 omega   -3.00   88.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000 -120.0000 182

 11 omega   22.00   69.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -99.0000   60.0000 94

 12 omega   12.00   94.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000 -180.0000 164

 13 omega    8.00   47.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000   30.0000 78

 14 omega   68.00   95.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000  -60.0000 54

 15 omega  -43.00   55.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000  120.0000 196

 16 omega  -46.00   52.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -38.0000   60.0000 196

 17 omega  -42.00   48.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -57.0000  -90.0000 180

 18 omega  -20.00   69.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -99.0000 -150.0000 178

 19 omega    1.00   99.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   38.0000  150.0000 196

 20 omega   -3.00   97.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000  -60.0000 200

 21 omega  -20.00   69.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -99.0000   60.0000 178

 22 omega   -3.00   97.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000   60.0000 200

 23 omega  -20.00   69.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -99.0000    0.0000 178

 24 omega   -3.00   97.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000 -150.0000 200

 25 omega  -20.00   65.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -99.0000 -180.0000 170

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Agilent Agilent Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_UB_11      -0.0442936000
_diffrn_orient_matrix_UB_12      0.0027435000
_diffrn_orient_matrix_UB_13      -0.0722735000
_diffrn_orient_matrix_UB_21      0.0325441000
_diffrn_orient_matrix_UB_22      0.0498772000
_diffrn_orient_matrix_UB_23      -0.0026265000
_diffrn_orient_matrix_UB_31      0.0633200000
_diffrn_orient_matrix_UB_32      -0.0237130000
_diffrn_orient_matrix_UB_33      -0.0140226000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            53453
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.286
_diffrn_reflns_theta_min         3.735
_diffrn_source                   'microfocus X-Ray tube'
_exptl_absorpt_coefficient_mu    0.896
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Numerical absorption correction based on gaussian integration over
 a multifaceted crystal model (Busing & Levy, 1957).
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 3062 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         7686
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0311P)^2^+0.0406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                7122
_reflns_number_total             7686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic7b00077_si_002.cif
_cod_data_source_block           ga_jw14
_cod_database_code               4345578
_audit_block_refno               2487
_audit_block_usercomment         'jw252 block orange'
_chemical_oxdiff_formula         'C22 H34 F1 Ni1 N3 O2'
_chemical_oxdiff_usercomment     'jw252 block orange'
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.916
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_shelxl_version_number           2016/6
_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 C(H,H,H) groups
2.a Idealised Me refined as rotating group with stretchable bonds:
 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)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_res_checksum              59499
_cell_oxdiff_length_a            9.0699(3)
_cell_oxdiff_length_b            12.8275(3)
_cell_oxdiff_length_c            10.3232(3)
_cell_oxdiff_angle_alpha         90.048(2)
_cell_oxdiff_angle_beta          111.142(3)
_cell_oxdiff_angle_gamma         89.985(2)
_cell_oxdiff_volume              1120.19(6)
_cell_oxdiff_measurement_reflns_used 18006