Regioselective hydrosilylation of epoxides catalysed by nickel(ii) hydrido complexes.
Wenz, Jan; Wadepohl, Hubert; Gade, Lutz H.; Chemical communications (Cambridge, England) 53 (2017) 4308–4311; doi:10.1039/c7cc01655g

data_7120084
_publ_section_title
;
 Regioselective hydrosilylation of epoxides catalysed by nickel(ii)
 hydrido complexes.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4308
_journal_page_last               4311
_journal_paper_doi               10.1039/c7cc01655g
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H43 N3 Ni O3, C8 H10 O'
_chemical_formula_sum            'C38 H53 N3 Ni O4'
_chemical_formula_weight         674.54
_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_jw28
_audit_creation_date             2016-04-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-02-13 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.93003(15)
_cell_length_b                   10.15945(19)
_cell_length_c                   35.2869(6)
_cell_measurement_reflns_used    23163
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.4800
_cell_measurement_theta_min      4.5240
_cell_volume                     3559.87(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41p (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41p (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41p (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
'encif (Wadepohl, 2009-15); encifer 1.5 (CCDC, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_environment      perfluoro
_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 0.997
_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    -21.00  69.00   1.00    2.00    --    0.00  57.00 120.00   90
  2  \w    -30.00  70.00   1.00    2.00    --    0.00  77.00   0.00  100
  3  \w    -69.00  21.00   1.00    2.00    --    0.00 -57.00-120.00   90
  4  \w    -72.00  26.00   1.00    2.00    --    0.00 -38.00 -30.00   98
  5  \w    -21.00  69.00   1.00    2.00    --    0.00  57.00 -90.00   90
  6  \w     24.00 124.00   1.00    4.00    --   54.00  77.00  60.00  100
  7  \w     24.00 124.00   1.00    4.00    --   54.00  77.00   0.00  100
  8  \w     24.00 124.00   1.00    4.00    --   54.00  77.00 150.00  100
  9  \w     23.00 111.00   1.00    4.00    --   54.00-125.00  30.00   88
 10  \w     24.00 124.00   1.00    4.00    --   54.00  77.00 -30.00  100
 11  \w     24.00 124.00   1.00    4.00    --   54.00  77.00  30.00  100
 12  \w    -15.00  75.00   1.00    4.00    --   54.00 -57.00-150.00   90
 13  \w     24.00 124.00   1.00    4.00    --   54.00  77.00  90.00  100
 14  \w     24.00 124.00   1.00    4.00    --   54.00  77.00 -60.00  100
 15  \w     24.00 124.00   1.00    4.00    --   54.00  77.00-180.00  100
 16  \w    -15.00  75.00   1.00    4.00    --   54.00 -57.00 120.00   90
 17  \w     24.00 124.00   1.00    4.00    --   54.00  77.00 -90.00  100
 18  \w    -15.00  75.00   1.00    4.00    --   54.00 -57.00  30.00   90
 19  \w     24.00 124.00   1.00    4.00    --   54.00  77.00-150.00  100
 20  \w     24.00 124.00   1.00    4.00    --   54.00  77.00-120.00  100
 21  \w     24.00 124.00   1.00    4.00    --   54.00  77.00 120.00  100
 22  \w     36.00 116.00   1.00   10.00    --  108.00-111.00-150.00   80
 23  \w     78.00 178.00   1.00   10.00    --  108.00  77.00 -60.00  100
 24  \w     78.00 178.00   1.00   10.00    --  108.00  77.00 120.00  100
 25  \w     79.00 178.00   1.00   10.00    --  108.00  75.00  36.54   99
 26  \w     78.00 178.00   1.00   10.00    --  108.00  77.00-120.00  100
 27  \w     36.00 116.00   1.00   10.00    --  108.00-111.00 120.00   80
 28  \w    100.00 178.00   1.00   10.00    --  108.00 111.00 -90.00   78
 29  \w     78.00 178.00   1.00   10.00    --  108.00  77.00  60.00  100
 30  \w     78.00 178.00   1.00   10.00    --  108.00  77.00 150.00  100
 31  \w     85.00 175.00   1.00   10.00    --  108.00  64.00 -33.47   90
 32  \w     84.00 178.00   1.00   10.00    --  108.00  42.00  66.04   94
 33  \w     80.00 178.00   1.00   10.00    --  108.00  74.00 116.28   98
 34  \w     78.00 178.00   1.00   10.00    --  108.00  77.00 -90.00  100
 35  \w     78.00 178.00   1.00   10.00    --  108.00  77.00 -30.00  100
 36  \w     38.00 138.00   1.00   10.00    --  108.00 -77.00-120.00  100
 37  \w     36.00 146.00   1.00   10.00    --  108.00 -92.00-150.00  110
 38  \w     78.00 178.00   1.00   10.00    --  108.00  77.00-180.00  100
 39  \w     36.00 116.00   1.00   10.00    --  108.00-111.00  60.00   80
 40  \w     86.00 178.00   1.00   10.00    --  108.00  50.00  30.00   92
 41  \w     81.00 177.00   1.00   10.00    --  108.00  71.00  -1.04   96
 42  \w     82.00 177.00   1.00   10.00    --  108.00  70.00  59.24   95
 43  \w     85.00 175.00   1.00   10.00    --  108.00  64.00  30.00   90
 44  \w     85.00 175.00   1.00   10.00    --  108.00  64.00 -60.00   90
 45  \w     85.00 175.00   1.00   10.00    --  108.00  64.00-150.00   90
 46  \w     78.00 178.00   1.00   10.00    --  108.00  77.00-150.00  100
 47  \w     86.00 178.00   1.00   10.00    --  108.00  50.00-150.00   92
 48  \w     86.00 178.00   1.00   10.00    --  108.00  49.00 164.80   92
 49  \w     85.00 175.00   1.00   10.00    --  108.00  64.00 -90.00   90
 50  \w     78.00 178.00   1.00   10.00    --  108.00  77.00  90.00  100
 51  \w     82.00 178.00   1.00   10.00    --  108.00  38.00 120.00   96
 52  \w     36.00 116.00   1.00   10.00    --  108.00-111.00 -30.00   80
 53  \w     87.00 178.00   1.00   10.00    --  108.00  52.00-173.01   91
 54  \w     81.00 177.00   1.00   10.00    --  108.00  71.00 -12.27   96
 55  \w     85.00 175.00   1.00   10.00    --  108.00  64.00-120.00   90
 56  \w     84.00 178.00   1.00   10.00    --  108.00  43.00 -75.71   94
 57  \w     85.00 178.00   1.00   10.00    --  108.00  45.00 137.15   93
 58  \w    -69.00  21.00   1.00    2.00    --    0.00 -57.00-180.00   90
 59  \f      0.00 120.00   1.00    2.00   0.00   0.00 -60.00    --   120
 60  \f      0.00 120.00   1.00    2.00   0.00   0.00  40.00    --   120
 61  \w    -21.00  69.00   1.00    2.00    --    0.00  57.00 150.00   90
 62  \f      0.00 120.00   1.00    2.00   0.00   0.00  60.00    --   120
 63  \f      0.00 120.00   1.00    2.00   0.00   0.00 -40.00    --   120
 64  \w    -70.00  30.00   1.00    2.00    --    0.00 -77.00 -30.00  100
 65  \w    -19.00  84.00   1.00    4.00    --   54.00 -29.00  -9.00  103
 66  \f    240.00 360.00   1.00    4.00  54.00  54.00 -60.00    --   120
 67  \w     33.00 123.00   1.00    4.00    --   54.00  57.00 150.00   90
 68  \f    240.00 360.00   1.00    4.00  54.00  54.00  60.00    --   120
 69  \w     28.00 126.00   1.00    4.00    --   54.00  38.00-180.00   98
 70  \f      0.00 120.00   1.00    4.00  54.00  54.00 -40.00    --   120
 71  \f      0.00 120.00   1.00    4.00  54.00  54.00  40.00    --   120
 72  \w     33.00 123.00   1.00    4.00    --   54.00  57.00  90.00   90
 73  \f    120.00 240.00   1.00    4.00  54.00  54.00 -60.00    --   120
 74  \w     33.00 123.00   1.00    4.00    --   54.00  57.00   0.00   90
 75  \f    120.00 240.00   1.00    4.00  54.00  54.00  40.00    --   120
 76  \f    120.00 240.00   1.00    4.00  54.00  54.00 -40.00    --   120
 77  \f    120.00 240.00   1.00    4.00  54.00  54.00  60.00    --   120
 78  \f    240.00 360.00   1.00    4.00  54.00  54.00 -40.00    --   120
 79  \f    240.00 360.00   1.00    4.00  54.00  54.00  40.00    --   120
 80  \w     23.00 111.00   1.00    4.00    --   54.00-125.00-180.00   88
 81  \f      0.00 120.00   1.00    4.00  54.00  54.00  60.00    --   120
 82  \w    -19.00  84.00   1.00    4.00    --   54.00 -29.00  -9.00  103
 83  \w     24.00 127.00   1.00    4.00    --   54.00  29.00 151.00  103
 84  \w    -15.00  75.00   1.00    4.00    --   54.00 -57.00 -90.00   90
 85  \f      0.00 120.00   1.00    4.00  54.00  54.00 -60.00    --   120
 86  \w     86.00 178.00   1.00   10.00    --  108.00  50.00 -60.00   92
 87  \w     41.00 131.00   1.00   10.00    --  108.00 -64.00   0.00   90
 88  \w     86.00 178.00   1.00   10.00    --  108.00  50.00 150.00   92
 89  \w     86.00 176.00   1.00   10.00    --  108.00  50.00-120.00   90
 90  \w     85.00 175.00   1.00   10.00    --  108.00  64.00-180.00   90
 91  \w     78.00  80.00   1.00   10.00    --  108.00  77.00   0.00    2
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  '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      0.1122261000
_diffrn_orient_matrix_UB_12      -0.1029300000
_diffrn_orient_matrix_UB_13      0.0054692000
_diffrn_orient_matrix_UB_21      -0.1039984000
_diffrn_orient_matrix_UB_22      -0.0982376000
_diffrn_orient_matrix_UB_23      0.0158152000
_diffrn_orient_matrix_UB_31      -0.0255472000
_diffrn_orient_matrix_UB_32      -0.0524994000
_diffrn_orient_matrix_UB_33      -0.0403236000
_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  0.0845
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            122869
_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         70.988
_diffrn_reflns_theta_min         4.529
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.118
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41p (Rigaku Oxford Diffraction, 2015)
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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2450 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         6862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0284P)^2^+1.8039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                6225
_reflns_number_total             6862
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc01655g2.cif
_cod_data_source_block           ga_jw28
_cod_original_cell_volume        3559.88(11)
_cod_database_code               7120084
_audit_block_refno               2693
_audit_block_usercomment         'JW491 orange irregular'
_chemical_oxdiff_formula         'C38 H53 N3 Ni1 O4'
_chemical_oxdiff_usercomment     'JW491 orange irregular'
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.896
_reflns_odcompleteness_completeness 99.95
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C1(H1), C16(H16), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C42(H42A,H42B), C11(H11A,H11B), C2(H2A,H2B),
 C41(H41A,H41B)
2.c Aromatic/amide H refined with riding coordinates:
 C44(H44), C30(H30), C7(H7), C27(H27), C48(H48), C26(H26), C46(H46), C45(H45),
 C28(H28), C29(H29), C47(H47), C6(H6)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C14(H14A,H14B,
 H14C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C17(H17A,H17B,H17C), C19(H19A,
 H19B,H19C)
;
_shelx_res_checksum              98488
_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 1.658
_oxdiff_exptl_absorpt_empirical_full_min 0.590
_cell_oxdiff_length_a            9.9313(2)
_cell_oxdiff_length_b            10.1579(3)
_cell_oxdiff_length_c            35.2880(5)
_cell_oxdiff_angle_alpha         90.0031(17)
_cell_oxdiff_angle_beta          89.9928(17)
_cell_oxdiff_angle_gamma         90.015(2)
_cell_oxdiff_volume              3559.88(14)
_cell_oxdiff_measurement_reflns_used 23162