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_4345588
_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         'C18 H24 Cl N3 Ni O2'
_chemical_formula_sum            'C18 H24 Cl N3 Ni O2'
_chemical_formula_weight         408.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_jw7
_audit_creation_date
;
'Tue Jun 09 11:55:20 2015'
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;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
'09.06.2015 12:02:02 CEST UTC+02:00  encif 1.32'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.02343(16)
_cell_length_b                   12.8832(3)
_cell_length_c                   17.6864(3)
_cell_measurement_reflns_used    12305
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      29.6970
_cell_measurement_theta_min      3.7660
_cell_volume                     1828.20(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
'encif (Wadepohl, 2009-14); encifer 1.5 (CCDC, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
  1 omega   30.00   56.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000 -120.0000 52

  2 omega   -5.00   20.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   80.0000   -2.9870 50

  3 omega  -40.00   58.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -79.0000 -169.3472 196

  4 omega  -40.00   -2.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000  -60.0000 76

  5 omega    4.00   54.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   38.0000 -150.0000 100

  6 omega   -3.00   58.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000  -60.0000 122

  7 omega    6.00   93.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000   60.0000 174

  8 omega   22.00   57.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000  -90.0000 70

  9 omega    0.00   37.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000  150.0000 74

 10 omega   30.00   56.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000  -60.0000 52

 11 omega    9.00   97.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000   60.0000 176

 12 omega   12.00   97.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000 -150.0000 170

 13 omega  -23.00   56.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000 -150.0000 158

 14 omega    3.00   51.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   38.0000   30.0000 96

 15 omega  -35.00   -9.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000   90.0000 52

 16 omega   28.00   55.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000   90.0000 54

 17 omega    9.00   35.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000 -150.0000 52

 18 omega    8.00   34.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   38.0000  -90.0000 52

 19 omega  -37.00   60.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -80.0000   -2.9165 194

 20 omega   33.00   59.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -78.0000  122.4695 52

 21 omega  -42.00   16.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -78.0000  122.4695 116

 22 omega  -41.00   58.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -77.0000   50.6651 198

 23 omega  -46.00  -21.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -38.0000   30.0000 50

;
_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_UB_11      0.0030364000
_diffrn_orient_matrix_UB_12      -0.0488695000
_diffrn_orient_matrix_UB_13      -0.0184209000
_diffrn_orient_matrix_UB_21      -0.0867135000
_diffrn_orient_matrix_UB_22      -0.0064572000
_diffrn_orient_matrix_UB_23      0.0062125000
_diffrn_orient_matrix_UB_31      -0.0168971000
_diffrn_orient_matrix_UB_32      0.0245275000
_diffrn_orient_matrix_UB_33      -0.0350787000
_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  0.0783
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            55664
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.878
_diffrn_reflns_theta_min         3.205
_diffrn_source                   'microfocus X-Ray tube'
_exptl_absorpt_coefficient_mu    1.224
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
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            'light red'
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       irregular
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 2186 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         6452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0273P)^2^+0.6509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                5837
_reflns_number_total             6452
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic7b00077_si_002.cif
_cod_data_source_block           ga_jw7
_cod_original_cell_volume        1828.19(6)
_cod_database_code               4345588
_audit_block_refno               2449
_audit_block_usercomment         'JW1605, irregular, red'
_chemical_oxdiff_formula         'C18 H24 Cl N3 Ni O2'
_chemical_oxdiff_usercomment     'JW1605, irregular, red'
_shelx_estimated_absorpt_t_max   0.887
_shelx_estimated_absorpt_t_min   0.887
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_shelxl_version_number           2014/7
_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)
;
_shelx_res_checksum              19790
_olex2_submission_special_instructions 'No special instructions were received'
_cell_oxdiff_length_a            8.02407(17)
_cell_oxdiff_length_b            12.8825(3)
_cell_oxdiff_length_c            17.6859(3)
_cell_oxdiff_angle_alpha         89.9925(16)
_cell_oxdiff_angle_beta          89.9691(16)
_cell_oxdiff_angle_gamma         89.9658(17)
_cell_oxdiff_volume              1828.19(6)
_cell_oxdiff_measurement_reflns_used 12305