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_4345590
_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      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_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_cr46
_audit_creation_date             2016-12-14
_audit_creation_method
;
Olex2 1.2
(compiled Nov 22 2016 12:06:14 for OlexSys, GUI svn.r5269)
;
_audit_update_record
'14.12.2016 11:44:52 CET UTC+01:00  encif 1.59'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.25806(4)
_cell_length_b                   12.98362(8)
_cell_length_c                   17.61718(9)
_cell_measurement_reflns_used    53040
_cell_measurement_temperature    110(1)
_cell_measurement_theta_max      32.2780
_cell_measurement_theta_min      3.7180
_cell_volume                     1888.905(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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_environment      perfluoro
_diffrn_ambient_temperature      110(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9241
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9749
_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     -4.00  22.00   0.50   15.00    --  -27.92  59.00  84.00   52
  2  \w    -77.00  -6.00   0.50   15.00    --  -27.92 -59.00 -55.00  142
  3  \w    -38.00 -11.00   0.50   15.00    --   28.00 -59.00 -55.00   54
  4  \w     27.00  52.00   0.50   15.00    --   28.00  59.00  84.00   50
  5  \w    -58.00  41.00   0.50   15.00    --  -27.92  77.00 -30.00  198
  6  \w    -43.00  -1.00   0.50   15.00    --  -27.92 -38.00  30.00   84
  7  \w     -5.00  21.00   0.50   15.00    --  -27.92  57.00-180.00   52
  8  \w    -97.00 -66.00   0.50   15.00    --  -27.92 -57.00-150.00   62
  9  \w    -46.00 -20.00   0.50   15.00    --  -27.92  57.00-180.00   52
 10  \w    -20.00  45.00   0.50   15.00    --  -27.92  38.00-150.00  130
 11  \w    -15.00  13.00   0.50   15.00    --  -27.92 -94.00 133.79   56
 12  \w     -2.00  64.00   0.50   15.00    --   28.00  77.00 -60.00  132
 13  \w     -4.00  94.00   0.50   15.00    --   28.00  77.00  60.00  196
 14  \w    -41.00  46.00   0.50   15.00    --   28.00 -57.00-120.00  174
 15  \w      7.00  97.00   0.50   15.00    --   28.00  57.00 -90.00  180
 16  \w    -41.00  33.00   0.50   15.00    --   28.00 -57.00 120.00  148
 17  \w      5.00  37.00   0.50   15.00    --   28.00  38.00 120.00   64
 18  \w     76.00 101.00   0.50   15.00    --   28.00  38.00 120.00   50
 19  \w     14.00  41.00   0.50   15.00    --   28.00  57.00 120.00   54
 20  \w    -19.00  72.00   0.50   15.00    --   28.00 -99.00  60.00  182
 21  \w      6.00  97.00   0.50   15.00    --   28.00  57.00-180.00  182
 22  \w     17.00  70.00   0.50   15.00    --   28.00 -99.00-150.00  106
 23  \w    -50.00  41.00   0.50   15.00    --  -27.92  57.00-120.00  182
 24  \w    -26.00  13.00   0.50   15.00    --  -27.92 -94.00 133.79   78
 25  \w    -60.00  43.00   0.50   15.00    --  -27.92  77.00  90.00  206
 26  \w    -55.00  45.00   0.50   15.00    --  -27.92  38.00  60.00  200
 27  \w      6.00  97.00   0.50   15.00    --   28.00  57.00 -60.00  182
 28  \w    -41.00  50.00   0.50   15.00    --   28.00 -57.00-180.00  182
 29  \w    -20.00  72.00   0.50   15.00    --   28.00 -99.00 -30.00  184
 30  \w      6.00  97.00   0.50   15.00    --   28.00  59.00  84.00  182
 31  \w     -4.00  58.00   0.50   15.00    --   28.00  77.00 -30.00  124
 32  \w      6.00  97.00   0.50   15.00    --   28.00  57.00-150.00  182
;
_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      -0.0039050000
_diffrn_orient_matrix_UB_12      0.0402952000
_diffrn_orient_matrix_UB_13      0.0271280000
_diffrn_orient_matrix_UB_21      0.0842221000
_diffrn_orient_matrix_UB_22      -0.0052229000
_diffrn_orient_matrix_UB_23      0.0068807000
_diffrn_orient_matrix_UB_31      0.0163618000
_diffrn_orient_matrix_UB_32      0.0365141000
_diffrn_orient_matrix_UB_33      -0.0289500000
_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  0.0287
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            93261
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.394
_diffrn_reflns_theta_min         3.344
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.159
_exptl_absorpt_correction_T_max  0.778
_exptl_absorpt_correction_T_min  0.562
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.600
_exptl_crystal_description       block
_exptl_crystal_F_000             936.000
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2732 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0042(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         6621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0173
_refine_ls_R_factor_gt           0.0162
_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^)+(0.0191P)^2^+0.3460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0381
_refine_ls_wR_factor_ref         0.0384
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                6468
_reflns_number_total             6621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic7b00077_si_002.cif
_cod_data_source_block           ga_cr46
_cod_database_code               4345590
_audit_block_refno               1728
_audit_block_usercomment         'cr770, block, orange'
_chemical_oxdiff_formula         'C18 H26 Br1 N3 Ni1 O2'
_chemical_oxdiff_usercomment     'cr770, block, orange'
_shelx_estimated_absorpt_t_max   0.743
_shelx_estimated_absorpt_t_min   0.743
_reflns_odcompleteness_completeness 99.70
_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 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)
;
_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 1.196
_oxdiff_exptl_absorpt_empirical_full_min 0.823
_shelx_res_checksum              25574
_cell_oxdiff_length_a            8.25867(5)
_cell_oxdiff_length_b            12.98410(6)
_cell_oxdiff_length_c            17.61522(7)
_cell_oxdiff_angle_alpha         90.0027(4)
_cell_oxdiff_angle_beta          89.9984(4)
_cell_oxdiff_angle_gamma         90.0025(4)
_cell_oxdiff_volume              1888.905(16)
_cell_oxdiff_measurement_reflns_used 53040