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_4345587
_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 H26 Br N3 Ni O2'
_chemical_formula_sum            'C18 H26 Br N3 Ni O2'
_chemical_formula_weight         455.04
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_cr44
_audit_creation_date
;
'Wed Mar 06 13:53:39 2013'
;
_audit_creation_method
;
Olex2 1.2
(compiled Nov 22 2016 12:06:14 for OlexSys, GUI svn.r5269)
;
_audit_update_record
'13.12.2016 16:04:21 CET UTC+01:00  encif 1.59'
_cell_angle_alpha                90
_cell_angle_beta                 94.7211(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.81923(6)
_cell_length_b                   7.67556(5)
_cell_length_c                   14.14396(8)
_cell_measurement_reflns_used    32428
_cell_measurement_temperature    110(1)
_cell_measurement_theta_max      32.1740
_cell_measurement_theta_min      3.5470
_cell_volume                     954.192(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
'encif (Wadepohl, 2009-16); encifer 1.5.2 (CCDC, 2016)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_temperature      110(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9241
_diffrn_detector_type            'Agilent EOS'
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9198
_diffrn_measurement_details
;
  1 omega    8.00   34.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.9245   77.0000   60.0000 52

  2 omega  -28.00   -2.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.9245  -38.0000    0.0000 52

  3 omega  -85.00  -59.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.9245  -77.0000    0.0000 52

  4 omega  -57.00  -31.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.9245   77.0000   60.0000 52

  5 omega  -22.00    4.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.9245  -77.0000    0.0000 52

  6 omega   35.00   60.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -77.0000 -180.0000 50

  7 omega   -1.00   25.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -77.0000 -180.0000 52

  8 omega  -35.00   38.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -38.0000  -60.0000 146

  9 omega  -39.00   60.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -77.0000  150.0000 198

 10 omega  -37.00   59.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -77.0000   60.0000 192

 11 omega    6.00   97.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   57.0000  120.0000 182

 12 omega   -4.00   95.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   77.0000 -180.0000 198

 13 omega    1.00   36.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   77.0000 -120.0000 70

 14 omega    6.00   93.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   57.0000  -60.0000 174

 15 omega   -4.00   99.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   77.0000    0.0000 206

 16 omega  -32.00    2.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -77.0000 -120.0000 68

 17 omega    9.00   60.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -77.0000 -120.0000 102

 18 omega   25.00   63.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -80.0000  -65.8260 76

 19 omega  -34.00   -2.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -80.0000  -65.8260 64

 20 omega  -60.00   43.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.9245   77.0000  -60.0000 206

 21 omega  -99.00    4.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.9245  -77.0000  -30.0000 206

 22 omega  -99.00    4.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.9245  -77.0000 -120.0000 206

 23 omega    6.00   97.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   57.0000  150.0000 182

 24 omega  -43.00   60.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -77.0000  120.0000 206

 25 omega  -41.00   50.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -57.0000   90.0000 182

 26 omega    6.00   97.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   57.0000  -90.0000 182

 27 omega    6.00   97.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   57.0000 -150.0000 182

 28 omega  -43.00   60.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -77.0000   30.0000 206

 29 omega    6.00   97.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   57.0000   60.0000 182

 30 omega  -43.00   60.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -77.0000 -150.0000 206

 31 omega  -41.00   50.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -57.0000   30.0000 182

 32 omega  -46.00  -21.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026    0.0000    0.0000 50

 33 omega  -41.00   63.00   0.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -80.0000  -65.8260 208

;
_diffrn_measurement_device       '\k-geometry 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      0.0192289000
_diffrn_orient_matrix_UB_12      0.0875751000
_diffrn_orient_matrix_UB_13      0.0116521000
_diffrn_orient_matrix_UB_21      0.0332512000
_diffrn_orient_matrix_UB_22      -0.0274338000
_diffrn_orient_matrix_UB_23      0.0448943000
_diffrn_orient_matrix_UB_31      0.0709650000
_diffrn_orient_matrix_UB_32      -0.0109124000
_diffrn_orient_matrix_UB_33      -0.0195088000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            54139
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.053
_diffrn_reflns_theta_min         3.524
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.127
_exptl_absorpt_correction_T_max  0.851
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 2863 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         6644
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0175
_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^)+(0.0168P)^2^+0.1614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0389
_refine_ls_wR_factor_ref         0.0392
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                6457
_reflns_number_total             6644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic7b00077_si_002.cif
_cod_data_source_block           ga_cr44
_cod_original_cell_volume        954.192(10)
_cod_database_code               4345587
_audit_block_refno               1717
_audit_block_usercomment         'cr767, plate, red'
_chemical_oxdiff_formula         'C18 H26 Br N3 Ni O2'
_chemical_oxdiff_usercomment     'cr767, plate, red'
_shelx_estimated_absorpt_t_max   0.745
_shelx_estimated_absorpt_t_min   0.745
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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 Ternary CH refined with riding coordinates:
 C1(H1), C12(H12), C13(H13), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_res_checksum              29758
_cell_oxdiff_length_a            8.81967(12)
_cell_oxdiff_length_b            7.67491(10)
_cell_oxdiff_length_c            14.14393(16)
_cell_oxdiff_angle_alpha         90.0227(10)
_cell_oxdiff_angle_beta          94.6959(10)
_cell_oxdiff_angle_gamma         89.9780(11)
_cell_oxdiff_volume              954.19(2)
_cell_oxdiff_measurement_reflns_used 32428