Electronic structure and reactivity of nickel(i) pincer complexes: their aerobic transformation to peroxo species and site selective C–H oxygenation
Rettenmeier, Christoph A.; Wadepohl, Hubert; Gade, Lutz H.; Chem. Sci. 7 (2016) 3533–; doi:10.1039/C5SC04644K

data_1542425
_publ_section_title
;
 Electronic structure and reactivity of nickel(i) pincer complexes: their
 aerobic transformation to peroxo species and site selective C--H
 oxygenation
;
_journal_issue                   6
_journal_name_full               'Chem. Sci.'
_journal_page_first              3533
_journal_paper_doi               10.1039/C5SC04644K
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H25 N3 Ni O4'
_chemical_formula_sum            'C25 H25 N3 Ni O4'
_chemical_formula_weight         490.19
_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_cr79
_audit_creation_date
;
'Wed Aug 12 15:54:56 2015'
;
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-11-26 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.41635(7)
_cell_length_b                   10.31527(11)
_cell_length_c                   32.9233(5)
_cell_measurement_reflns_used    38780
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.5430
_cell_measurement_theta_min      4.4970
_cell_volume                     2179.07(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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 0.998
_diffrn_measurement_details
;
  1 omega  -68.00   15.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 83

  2 omega  -66.00  -34.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -60.0000 32

  3 omega  -19.00   16.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  -90.0000 35

  4 omega  -16.00   21.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -60.0000 37

  5 omega  -12.00   66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 78

  6 omega   39.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  -90.0000 30

  7 omega  -11.00   73.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -180.0000 84

  8 omega   24.00   56.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -90.0000 32

  9 omega   24.00   50.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000    0.0000 26

 10 omega   79.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  150.0000 45

 11 omega   71.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -150.0000 53

 12 omega   64.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  120.0000 45

 13 omega  -17.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -80.0000  104.0504 102

 14 omega   24.00   51.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -180.0000 27

 15 omega   24.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -120.0000 34

 16 omega   24.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -150.0000 41

 17 omega   25.00   54.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  120.0000 29

 18 omega   59.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -90.0000 26

 19 omega   24.00   50.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 26

 20 omega   29.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   60.0000 94

 21 omega   31.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -60.0000 93

 22 omega   25.00   67.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  150.0000 42

 23 omega   24.00   50.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 26

 24 omega  -16.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -80.0000  -47.4903 101

 25 omega    5.00   50.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000    0.0000 45

 26 omega   25.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   30.0000 79

 27 omega   74.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 49

 28 omega   85.00  174.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -150.0000 89

 29 omega   87.00  116.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000  118.2188 29

 30 omega  129.00  167.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -30.0000 38

 31 omega   85.00  111.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -30.0000 26

 32 omega  128.00  166.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   75.0000 -174.3749 38

 33 omega   68.00  108.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -79.0000   -7.3843 40

 34 omega   78.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 99

 35 omega   82.00  108.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -90.0000 26

 36 omega   80.00  124.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   75.0000 -174.3749 44

 37 omega   84.00  110.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   68.0000  170.8221 26

 38 omega   39.00   67.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -79.0000   -7.3843 28

 39 omega   81.00  113.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   34.0000   47.2586 32

 40 omega  153.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 25

 41 omega   78.00  104.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 26

 42 omega  112.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 64

 43 omega   80.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   73.0000  150.7124 97

 44 omega   79.00  105.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

 45 omega   78.00  104.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26

 46 omega   78.00  104.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

 47 omega   80.00  107.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   73.0000   78.7352 27

 48 omega   37.00  109.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -79.0000   62.4082 72

 49 omega  142.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 34

 50 omega   78.00  108.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 30

 51 omega   87.00  175.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   58.0000   -0.3591 88

 52 omega  138.00  170.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -90.0000 32

 53 omega   85.00  111.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -90.0000 26

 54 omega   78.00  105.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 27

 55 omega   78.00  104.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 26

 56 omega  117.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 60

 57 omega   79.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   76.0000 -121.6230 98

 58 omega   78.00  104.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 26

 59 omega   78.00  104.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

 60 omega   82.00  109.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000    0.0000 27

 61 omega   37.00   97.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -79.0000 -161.1018 60

 62 omega   85.00  114.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -60.0000 29

 63 omega   86.00  111.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -180.0000 25

 64 omega   85.00  174.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   60.0000 89

 65 omega  123.00  174.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  120.0000 51

 66 omega   85.00  116.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  120.0000 31

 67 omega   72.00  115.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -79.0000  115.1589 43

 68 omega   43.00   98.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 55

 69 omega   38.00  105.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000  -62.3107 67

 70 omega   81.00  116.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   34.0000 -177.9354 35

 71 omega  -72.00   25.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -39.0000  -31.0000 97

 72 omega  -72.00   26.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000   30.0000 98

 73 omega  -72.00   26.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -90.0000 98

 74 omega  -30.00   70.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000    0.0000 100

 75 omega  -26.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  -60.0000 98

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

 77 omega  -16.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000 -180.0000 100

 78 omega  -18.00   80.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   30.0000 98

 79 omega   24.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   30.0000 100

 80 omega   33.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 90

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

 82 omega   24.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  150.0000 100

 83 omega  -16.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000 -120.0000 100

 84 omega   33.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 90

 85 omega  -16.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000    0.0000 100

 86 omega   33.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 90

 87 omega   33.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 90

 88 omega   24.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 100

 89 omega  -17.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -79.0000   51.8354 102

 90 omega  -18.00   80.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000 -120.0000 98

 91 omega   33.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 90

 92 omega   33.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 90

 93 omega   24.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -120.0000 100

 94 omega   33.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  150.0000 90

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

 96 omega   37.00  139.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -79.0000   35.7749 102

 97 omega   35.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 59

 98 omega   85.00  175.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   60.0000 90

 99 omega   35.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 59

100 omega   38.00  139.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -78.0000 -149.8915 101

101 omega   35.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 59

102 omega   85.00  110.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -180.0000 25

103 omega   82.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  150.0000 96

104 omega   82.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -60.0000 96

105 omega   86.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -120.0000 92

106 omega   78.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 100

107 omega   86.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000   30.0000 92

108 omega   86.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -180.0000 92

109 omega   85.00  175.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -120.0000 90

110 omega   83.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   39.0000  122.0000 95

111 omega   38.00  138.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 100

112 omega   80.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   74.0000  -64.3140 98

113 omega   86.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 92

114 omega   37.00  140.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000  -62.3107 103

115 omega   85.00  175.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  150.0000 90

116 omega   78.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 100

117 omega   87.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   58.0000   -0.3591 90

118 omega   86.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -90.0000 92

;
_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      -0.0042719000
_diffrn_orient_matrix_UB_12      0.1398011000
_diffrn_orient_matrix_UB_13      0.0164701000
_diffrn_orient_matrix_UB_21      0.2230636000
_diffrn_orient_matrix_UB_22      -0.0170717000
_diffrn_orient_matrix_UB_23      0.0164313000
_diffrn_orient_matrix_UB_31      0.0886369000
_diffrn_orient_matrix_UB_32      0.0497530000
_diffrn_orient_matrix_UB_33      -0.0405989000
_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  0.0438
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            73508
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.922
_diffrn_reflns_theta_min         4.492
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.608
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1697 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(6)
_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     366
_refine_ls_number_reflns         4182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0228
_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^)+(0.0251P)^2^+0.8674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0575
_refine_ls_wR_factor_ref         0.0576
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4156
_reflns_number_total             4182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc04644k2.cif
_cod_data_source_block           ga_cr79
_cod_depositor_comments
'Adding full bibliography for 1542422--1542426.cif.'
_cod_database_code               1542425
_audit_block_refno               2505
_audit_block_usercomment         'cr1253, needle, red'
_chemical_oxdiff_formula         'C25 H25 N3 Ni O4'
_chemical_oxdiff_usercomment     'cr1253, needle, red'
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.856
_reflns_odcompleteness_completeness 99.91
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group with stretchable bonds:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              19850
_olex2_submission_special_instructions 'No special instructions were received'
_cell_oxdiff_length_a            6.41717(8)
_cell_oxdiff_length_b            10.31369(12)
_cell_oxdiff_length_c            32.9241(5)
_cell_oxdiff_angle_alpha         90.0172(11)
_cell_oxdiff_angle_beta          89.9810(11)
_cell_oxdiff_angle_gamma         90.0071(10)
_cell_oxdiff_volume              2179.07(5)
_cell_oxdiff_measurement_reflns_used 38779