Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization.
Clarke, Christopher; Incerti-Pradillos, Celia A; Lam, Hon Wai; Journal of the American Chemical Society 138 (2016) 8068–8071; doi:10.1021/jacs.6b04206

data_4130517
_publ_section_title
;
 Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of
 Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z
 Isomerization.
;
_journal_issue                   26
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8068
_journal_page_last               8071
_journal_paper_doi               10.1021/jacs.6b04206
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H20 O2'
_chemical_formula_sum            'C22 H20 O2'
_chemical_formula_weight         316.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-08-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.1504(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.42710(10)
_cell_length_b                   6.00798(4)
_cell_length_c                   29.0300(2)
_cell_measurement_reflns_used    43666
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.5160
_cell_measurement_theta_min      4.8450
_cell_volume                     1641.71(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -49.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000 -120.0000 71

  2 omega  -35.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000   30.0000 68

  3 omega  -94.00  -34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000  120.0000 60

  4 omega  -66.00   -6.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000   30.0000 60

  5 omega   20.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   57.0000  -90.0000 93

  6 omega  121.00  151.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   30.0000 -150.0000 30

  7 omega   30.00   55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000   90.0000 25

  8 omega   71.00  110.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -54.0000   86.7934 39

  9 omega  110.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000   90.0000 65

 10 omega   85.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000 -150.0000 26

 11 omega   87.00  157.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   80.0000  -79.5474 70

 12 omega   73.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000   90.0000 27

 13 omega   60.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000    0.0000 62

 14 omega   77.00  161.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000   60.0000 84

 15 omega   73.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000   60.0000 26

 16 omega   35.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000 -150.0000 26

 17 omega   46.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  150.0000 26

 18 omega   41.00  149.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -15.0000  -90.0000 108

 19 omega   59.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -61.0000  -30.0000 44

 20 omega   30.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000  150.0000 45

 21 omega   53.00  119.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000  120.0000 66

 22 omega   34.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000   30.0000 67

 23 omega   54.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000  -90.0000 62

 24 omega  100.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000 -180.0000 26

 25 omega   39.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000 -120.0000 29

 26 omega   45.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  -30.0000 48

 27 omega   59.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   15.0000   60.0000 42

 28 omega  131.00  157.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   15.0000   60.0000 26

 29 omega   32.00   57.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000  150.0000 25

 30 omega   69.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000  150.0000 26

 31 omega   74.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  -90.0000 58

 32 omega   87.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000 -180.0000 28

 33 omega  122.00  148.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000 -180.0000 26

 34 omega   42.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  -60.0000 26

 35 omega   40.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -25.0000 -111.5735 49

 36 omega   81.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000   30.0000 32

 37 omega   62.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -39.0000   12.9098 27

 38 omega -111.00  -52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000 -158.0000  158.0000 59

 39 omega   11.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   77.0000   90.0000 106

 40 omega   11.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   77.0000   30.0000 106

 41 omega   16.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   57.0000 -150.0000 97

 42 omega   16.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   57.0000    0.0000 97

 43 omega  -27.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292  -57.0000   60.0000 96

 44 omega   73.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000 -120.0000 105

 45 omega   73.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  -30.0000 105

 46 omega   73.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000   90.0000 105

 47 omega   80.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000 -150.0000 96

 48 omega   23.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000  -30.0000 86

 49 omega   33.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000  -60.0000 89

 50 omega   73.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000 -150.0000 105

 51 omega   23.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000   60.0000 86

 52 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  -90.0000 98

 53 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  -30.0000 98

 54 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000    0.0000 98

 55 omega   73.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  -60.0000 105

 56 omega   74.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   72.0000   14.2037 102

 57 omega   73.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000   30.0000 105

 58 omega   34.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -61.0000  120.0000 98

 59 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000 -150.0000 98

 60 omega   73.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  150.0000 105

 61 omega   73.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000   60.0000 105

 62 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000 -120.0000 98

 63 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  -60.0000 98

 64 omega   73.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000 -180.0000 105

 65 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000   90.0000 98

 66 omega   34.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -61.0000   30.0000 98

 67 omega   73.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  120.0000 105

 68 omega  -94.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000 -120.0000 92

 69 omega   11.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   77.0000  120.0000 106

 70 omega   11.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   77.0000 -120.0000 106

 71 omega   11.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   77.0000  -60.0000 106

 72 omega   20.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   38.0000  -30.0000 95

 73 omega   20.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   38.0000  -60.0000 95

 74 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  150.0000 98

 75 omega   33.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  150.0000 65

 76 omega   73.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000    0.0000 105

 77 omega   34.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -61.0000 -120.0000 98

 78 omega   23.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000  -60.0000 86

 79 omega   33.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000  -90.0000 89

 80 omega   30.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000   30.0000 61

 81 omega   28.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -25.0000 -111.5735 65

 82 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000   30.0000 98

 83 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  120.0000 98

 84 omega   80.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  120.0000 96

 85 omega   80.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000 -120.0000 96

 86 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000 -180.0000 98

 87 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000   60.0000 98

 88 omega   30.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000  150.0000 61

 89 omega   32.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -39.0000   12.9098 61

 90 omega   24.00  150.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -15.0000   60.0000 126

 91 omega   75.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   80.0000  -79.5474 103

 92 omega   33.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000   30.0000 89

 93 omega   80.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  -60.0000 96

 94 omega   80.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  -30.0000 96

 95 omega   80.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000   30.0000 96

 96 omega   80.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000   90.0000 96

 97 omega   73.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  -90.0000 105

 98 omega -112.00   -7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -77.0000   90.0000 105

 99 omega  -44.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292    0.0000  -90.0000 173

100 omega  -44.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292    0.0000 -150.0000 173

101 omega  -44.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292    0.0000 -120.0000 173

102 omega   16.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   57.0000  120.0000 97

103 omega  -44.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292    0.0000 -180.0000 173

104 omega   80.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  150.0000 96

105 omega   26.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -19.0000  -58.8491 87

106 omega   72.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   22.0000   75.7758 106

107 omega   34.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -61.0000 -150.0000 98
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      -0.0238105000
_diffrn_orient_matrix_UB_12      -0.2536613000
_diffrn_orient_matrix_UB_13      0.0006446000
_diffrn_orient_matrix_UB_21      -0.0496948000
_diffrn_orient_matrix_UB_22      0.0164724000
_diffrn_orient_matrix_UB_23      0.0495697000
_diffrn_orient_matrix_UB_31      -0.1540780000
_diffrn_orient_matrix_UB_32      0.0338861000
_diffrn_orient_matrix_UB_33      -0.0191718000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            47900
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.697
_diffrn_reflns_theta_min         6.107
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.5225
_exptl_crystal_size_mid          0.2792
_exptl_crystal_size_min          0.1709
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1487 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_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     218
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0398P)^2^+0.5391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0692
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3312
_reflns_number_total             3312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b04206_si_004.cif
_cod_data_source_block           ciphla
_cod_database_code               4130517
_nottingham_internal_coll_name   CIPHLA
_nottingham_internal_coll_number 15057
_nottingham_internal_coll_client CIP/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '2.0000, 4.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   03/08/2015
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 04/08/2015
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 4/8/2015
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 4/8/2015
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 4/8/2015
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 4/8/2015
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C22 H20 O2'
_chemical_oxdiff_usercomment
'CIPHLA #15057 GVB-678 IN FOMBLIN FILM ON A MICROMOUNT FOR CIP/HWL'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C5(H15)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              73470
_shelx_hkl_checksum              24856
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'