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_4345586
_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 H35 N3 Ni O2'
_chemical_formula_sum            'C22 H35 N3 Ni O2'
_chemical_formula_weight         432.24
_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_jw20
_audit_creation_date             2015-11-30
_audit_creation_method
;
Olex2 1.2
(compiled Dec 12 2016 15:58:59 for OlexSys, GUI svn.r5292)
;
_audit_update_record
'15.02.2017 13:39:46 CET UTC+01:00  encif 1.68'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.92444(10)
_cell_length_b                   13.18377(17)
_cell_length_c                   19.0512(2)
_cell_measurement_reflns_used    20463
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      28.7530
_cell_measurement_theta_min      3.9290
_cell_volume                     2241.52(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    '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 0.995
_diffrn_measured_fraction_theta_max 0.967
_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     -3.00  87.00   0.50   22.50    --   18.62  57.00 -60.00  180
  2  \w      6.00  80.00   0.50   22.50    --   18.62-132.00 143.00  148
  3  \w     -3.00  87.00   0.50   22.50    --   18.62  57.00-150.00  180
  4  \w    -54.00  44.00   0.50   22.50    --   18.62 -38.00 150.00  196
  5  \w    -52.00  49.00   0.50   22.50    --   18.62 -77.00   0.00  202
  6  \w    -50.00  24.00   0.50   22.50    --   18.62 -57.00  60.00  148
  7  \w    -50.00  40.00   0.50   22.50    --   18.62 -57.00-120.00  180
  8  \f      6.00  32.00   0.50   22.50  18.62  18.62  40.00    --    52
  9  \w    -11.00  84.00   0.50   22.50    --   18.62  77.00 120.00  190
 10  \w    -20.00  59.00   0.50   22.50    --   18.62 -99.00 150.00  158
 11  \w    -10.00  18.00   0.50   22.50    --   18.62  77.00-180.00   56
 12  \w      1.00  87.00   0.50   22.50    --   18.62  57.00  30.00  172
 13  \w     33.00  84.00   0.50   22.50    --   18.62-138.00 -32.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Agilent Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0006188000
_diffrn_orient_matrix_UB_12      0.0015662000
_diffrn_orient_matrix_UB_13      -0.0372153000
_diffrn_orient_matrix_UB_21      0.0392214000
_diffrn_orient_matrix_UB_22      0.0467783000
_diffrn_orient_matrix_UB_23      0.0008019000
_diffrn_orient_matrix_UB_31      0.0691119000
_diffrn_orient_matrix_UB_32      -0.0265425000
_diffrn_orient_matrix_UB_33      -0.0007853000
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            44527
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.889
_diffrn_reflns_theta_min         3.489
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent Agilent SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       irregular
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 2141 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0327P)^2^+0.7129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0700
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                5376
_reflns_number_total             5571
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic7b00077_si_002.cif
_cod_data_source_block           ga_jw20
_cod_original_cell_volume        2241.52(5)
_cod_database_code               4345586
_audit_block_refno               2585
_chemical_oxdiff_formula         'C22 H35 N3 Ni O2'
_chemical_oxdiff_usercomment     'JW333, irregular, yellow'
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.917
_reflns_odcompleteness_completeness 99.51
_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 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), 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), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,
 H22B,H22C)
;
_audit_block_usercomment         'JW333, irregular, yellow'
_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 1.118
_oxdiff_exptl_absorpt_empirical_full_min 0.905
_shelx_res_checksum              32309
_cell_oxdiff_length_a            8.92560(10)
_cell_oxdiff_length_b            13.18237(17)
_cell_oxdiff_length_c            19.0507(3)
_cell_oxdiff_angle_alpha         90.0020(11)
_cell_oxdiff_angle_beta          90.0040(10)
_cell_oxdiff_angle_gamma         89.9911(10)
_cell_oxdiff_volume              2241.52(5)
_cell_oxdiff_measurement_reflns_used 20463