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_4345575
_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         '1(C22 H35 N3 O2)'
_chemical_formula_sum            'C22 H35 N3 O2'
_chemical_formula_weight         373.53
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_jw8a
_audit_creation_date
;
'Fri Jul 03 15:16:52 2015'
;
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
'03.07.2015 15:56:08 CEST UTC+02:00  encif 1.32'
_cell_angle_alpha                76.6714(19)
_cell_angle_beta                 73.361(2)
_cell_angle_gamma                72.030(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9246(2)
_cell_length_b                   10.7159(2)
_cell_length_c                   11.3098(2)
_cell_measurement_reflns_used    17827
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.8560
_cell_measurement_theta_min      4.1160
_cell_volume                     1082.80(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega  -68.00    9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000  150.0000 77

  2 omega  -24.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000    0.0000 -180.0000 73

  3 omega   23.00   61.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000 -150.0000 38

  4 omega  -26.00   18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000 -150.0000 44

  5 omega  -72.00  -30.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000    0.0000 -180.0000 42

  6 omega  -29.00   -4.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       14.0000  105.0000  -65.4181 25

  7 omega  -21.00    4.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0000  111.0000   75.9766 25

  8 omega  -23.00    2.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  118.0000  108.3232 25

  9 omega   -2.00   23.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   96.0000  136.6253 25

 10 omega    5.00   30.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   89.0000   58.5774 25

 11 omega   10.00   35.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   80.0000  142.6945 25

 12 omega   14.00   39.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   80.0000  -66.9407 25

 13 omega   13.00   38.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   82.0000 -126.4816 25

 14 omega   12.00   38.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000   54.1699 26

 15 omega   19.00   44.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  -20.3631 25

 16 omega   18.00   43.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000 -158.4197 25

 17 omega    1.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  -90.0000 93

 18 omega   25.00   50.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000    0.0000 25

 19 omega   34.00   61.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   30.0000 27

 20 omega  -15.00   74.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000    0.0000 89

 21 omega   97.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 27

 22 omega   24.00   51.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  150.0000 27

 23 omega   24.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 60

 24 omega   25.00   54.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 29

 25 omega  -15.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  150.0000 92

 26 omega   24.00   52.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -180.0000 28

 27 omega   33.00   60.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -160.3972 27

 28 omega   28.00   55.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000    7.2504 27

 29 omega  103.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -160.3972 25

 30 omega   33.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -27.6448 25

 31 omega   38.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  158.3465 27

 32 omega   29.00   56.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000 -102.9232 27

 33 omega   28.00   55.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -47.2932 27

 34 omega   30.00   57.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   73.0000  -68.4220 27

 35 omega   61.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  107.3901 27

 36 omega   28.00   55.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  107.3901 27

 37 omega   38.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -102.2525 27

 38 omega   35.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   73.0000  116.5766 30

 39 omega   35.00   60.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   74.0000   15.5788 25

 40 omega   35.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -144.6905 34

 41 omega   38.00   63.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000   52.7864 25

 42 omega   56.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   63.0000  -85.9401 27

 43 omega   47.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   60.0000   36.8136 39

 44 omega   61.00  129.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   54.0000  144.2745 68

 45 omega   45.00  132.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   68.0000  -64.8320 87

 46 omega   41.00   70.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000 -164.1809 29

 47 omega   53.00   79.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   67.0000   99.3986 26

 48 omega   47.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   73.0000  -12.4116 25

 49 omega   72.00   99.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   64.0000 -148.1748 27

 50 omega   56.00  140.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   48.0000  -90.1298 84

 51 omega   54.00  149.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   74.0000   93.9808 95

 52 omega   55.00   99.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   71.0000   48.1025 44

 53 omega   53.00   80.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   76.0000 -170.1444 27

 54 omega   73.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   52.0000 -141.0798 34

 55 omega   66.00  108.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   74.0000  155.7671 42

 56 omega   77.00  103.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   53.0000   82.4226 26

 57 omega  116.00  175.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 59

 58 omega   80.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 27

 59 omega   85.00  175.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -90.0000 90

 60 omega   78.00  105.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 27

 61 omega  128.00  174.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 46

 62 omega   79.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 25

 63 omega   95.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 82

 64 omega   78.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 29

 65 omega   67.00  115.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 48

 66 omega   39.00   64.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 25

 67 omega   83.00  157.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 74

 68 omega   85.00  113.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -180.0000 28

 69 omega   82.00  110.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -30.0000 28

 70 omega   85.00  130.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -120.0000 45

 71 omega   86.00  155.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -120.0000 69

 72 omega   85.00  111.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  120.0000 26

 73 omega   79.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 25

 74 omega   89.00  114.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 25

 75 omega  141.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 36

 76 omega   36.00  145.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -92.0000  -30.0000 109

 77 omega  142.00  169.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 27

 78 omega   89.00  114.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 25

 79 omega   86.00  165.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   90.0000 79

 80 omega   86.00  115.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -60.0000 29

 81 omega   86.00  112.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -150.0000 26

 82 omega   39.00  103.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 64

 83 omega  140.00  167.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000    0.0000 27

 84 omega   85.00  113.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000    0.0000 28

 85 omega   88.00  119.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 31

 86 omega  115.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 63

 87 omega   78.00  105.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 27

 88 omega   37.00  112.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 75

 89 omega   86.00  168.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   30.0000 82

 90 omega   83.00  108.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  150.0000 25

 91 omega   61.00   88.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 27

 92 omega   79.00  176.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 97

 93 omega   93.00  120.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -90.0000 27

 94 omega   82.00  116.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -150.0000 34

 95 omega  132.00  159.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 27

 96 omega   78.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

 97 omega   79.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 25

 98 omega   78.00  105.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 27

 99 omega   78.00  105.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 27

100 omega  130.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 48

101 omega   79.00  127.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 48

102 omega  -69.00   21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -90.0000 90

103 omega  -30.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -60.0000 100

104 omega  -30.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 100

105 omega  -21.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   60.0000 90

106 omega  -26.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  120.0000 98

107 omega  -33.00   -3.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0000  127.0000 -139.6276 30

108 omega   10.00   46.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   80.0000  142.6945 36

109 omega   14.00   46.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   80.0000  -66.9407 32

110 omega  -15.00   75.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 90

111 omega  -16.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  150.0000 100

112 omega   24.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000    0.0000 100

113 omega   24.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -60.0000 100

114 omega  -19.00  127.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000 -120.0000 146

115 omega   24.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 100

116 omega  -19.00  127.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000 -180.0000 146

117 omega  -19.00  127.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000  -30.0000 146

118 omega  -15.00   75.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 90

119 omega  -19.00  127.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000  -90.0000 146

120 omega  -19.00  127.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000 -150.0000 146

121 omega   23.00  111.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  120.0000 88

122 omega  -19.00  127.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000  -60.0000 146

123 omega   28.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  107.3901 100

124 omega   30.00  127.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   73.0000  -68.4220 97

125 omega   29.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  158.3465 99

126 omega   33.00  132.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -144.6905 99

127 omega   34.00  132.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   74.0000   15.5788 98

128 omega   42.00  134.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   68.0000  -64.8320 92

129 omega   37.00  136.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000   52.7864 99

130 omega   45.00  135.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   54.0000  144.2745 90

131 omega   45.00  134.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   60.0000   36.8136 89

132 omega   41.00  140.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000 -164.1809 99

133 omega   47.00  141.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   46.0000  135.1768 94

134 omega   46.00  143.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   73.0000  -12.4116 97

135 omega   51.00  141.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   64.0000 -148.1748 90

136 omega   50.00  142.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   67.0000   99.3986 92

137 omega   55.00  149.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   48.0000  -90.1298 94

138 omega  100.00  125.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 25

139 omega   38.00  138.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 100

140 omega   36.00   93.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 57

;
_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      -0.0656946000
_diffrn_orient_matrix_UB_12      0.1507832000
_diffrn_orient_matrix_UB_13      -0.0295647000
_diffrn_orient_matrix_UB_21      -0.0907797000
_diffrn_orient_matrix_UB_22      0.0002330000
_diffrn_orient_matrix_UB_23      0.1356191000
_diffrn_orient_matrix_UB_31      0.1248824000
_diffrn_orient_matrix_UB_32      0.0260149000
_diffrn_orient_matrix_UB_33      0.0380680000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            37458
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.104
_diffrn_reflns_theta_min         4.130
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.941
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 3068 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     584
_refine_ls_number_reflns         7668
_refine_ls_number_restraints     171
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0413P)^2^+0.1893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    0.872
_reflns_Friedel_fraction_max     0.841
_reflns_number_gt                7189
_reflns_number_total             7668
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic7b00077_si_002.cif
_cod_data_source_block           ga_jw8a
_cod_original_cell_volume        1082.80(5)
_cod_database_code               4345575
_audit_block_refno               2472
_audit_block_usercomment         'jwalk223 plate colourless'
_chemical_oxdiff_formula         'C22 H35 N3 O2'
_chemical_oxdiff_usercomment     'jwalk223 plate colourless'
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.944
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C1A \\sim C2A \\sim C3A \\sim C16A \\sim C17A \\sim C18A \\sim C1B \\sim C2B
\\sim C3B \\sim C16B \\sim C17B \\sim C18B \\sim C4 \\sim C5 \\sim C6 \\sim C7
\\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15
\\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C51 \\sim C52 \\sim C53 \\sim C54
\\sim C55 \\sim C56 \\sim C57 \\sim C58 \\sim C59 \\sim C60 \\sim C61 \\sim C62
\\sim C63 \\sim C64 \\sim C65 \\sim C66 \\sim C67 \\sim C68 \\sim C69 \\sim C70
\\sim C71 \\sim C72 \\sim O1A \\sim O1B \\sim O2 \\sim O51 \\sim O52 \\sim N1A
\\sim N1B \\sim N2 \\sim N3 \\sim N51 \\sim N52 \\sim N53: within 1A with sigma
of 0.04 and sigma for terminal atoms of 0.04
3. Rigid body (RIGU) restrains
 O1A, N1A, C1A, C2A, C3A, C16A, C17A, C18A, O1B, N1B, C1B, C2B, C3B, C16B,
 C17B, C18B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{O1A, N1A, C1A, C2A, C3A, C16A, C17A, C18A} sigma for 1-2: 0.02, 1-3: 0.02
as
{O1B, N1B, C1B, C2B, C3B, C16B, C17B, C18B}
5. Others
 Sof(O1B)=Sof(N1B)=Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(C3B)=
 Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C18B)=
 Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(O1A)=Sof(N1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=
 Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C18A)=
 Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1A(H1A), C16A(H16A), C1B(H1B), C16B(H16B), C11(H11), C13(H13), C51(H51),
 C61(H61), C63(H63), C66(H66)
6.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C2B(H2BA,H2BB), C12(H12A,H12B), C52(H52A,H52B), C62(H62A,H62B)
6.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C56(H56), C57(H57)
6.d Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C18A(H18A,H18B,H18C), C17B(H17D,H17E,H17F), C18B(H18D,
 H18E,H18F), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C64(H64A,H64B,
 H64C), C65(H65A,H65B,H65C), C67(H67A,H67B,H67C), C68(H68A,H68B,H68C), C69(H69A,
 H69B,H69C), C70(H70A,H70B,H70C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C)
;
_shelx_res_checksum              28736
_olex2_submission_special_instructions 'No special instructions were received'
_cell_oxdiff_length_a            9.9246(2)
_cell_oxdiff_length_b            10.7159(2)
_cell_oxdiff_length_c            11.3098(2)
_cell_oxdiff_angle_alpha         76.6714(19)
_cell_oxdiff_angle_beta          73.361(2)
_cell_oxdiff_angle_gamma         72.030(2)
_cell_oxdiff_volume              1082.80(4)
_cell_oxdiff_measurement_reflns_used 17827