Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the allylation of aryl halides with allylic alcohols.
Jia, Xue-Gong; Guo, Peng; Duan, Jicheng; Shu, Xing-Zhong; Chemical science 9 (2018) 640–645; doi:10.1039/c7sc03140h

data_1547881
_publ_section_title
;
 Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the
 allylation of aryl halides with allylic alcohols.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              640
_journal_page_last               645
_journal_paper_doi               10.1039/c7sc03140h
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C19 H19 Br N2 Ni'
_chemical_formula_sum            'C19 H19 Br N2 Ni'
_chemical_formula_weight         413.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1mvnns
_audit_creation_date             2016-11-04
_audit_creation_method
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Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
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_audit_update_record
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2016-11-05 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.163(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4028(11)
_cell_length_b                   11.9498(9)
_cell_length_c                   17.1489(17)
_cell_measurement_reflns_used    1088
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.8690
_cell_measurement_theta_min      3.9060
_cell_volume                     1717.4(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   67.00   94.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -15.0000  -60.0000 18

  2 omega   29.00   80.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430 -142.0000  -78.0000 34

  3 omega   -6.00   93.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430   38.0000   60.0000 66

  4 omega  -38.00   32.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -57.0000  -90.0000 47
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0596536000
_diffrn_orient_matrix_UB_12      0.0103144000
_diffrn_orient_matrix_UB_13      0.0263089000
_diffrn_orient_matrix_UB_21      -0.0579154000
_diffrn_orient_matrix_UB_22      0.0051537000
_diffrn_orient_matrix_UB_23      -0.0320176000
_diffrn_orient_matrix_UB_31      -0.0156711000
_diffrn_orient_matrix_UB_32      -0.0582351000
_diffrn_orient_matrix_UB_33      0.0018174000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0849
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6745
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.53
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.456
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.477
_refine_diff_density_min         -1.268
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0781
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+10.4519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1843
_reflns_number_gt                2132
_reflns_number_total             3378
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7sc03140h2.cif
_cod_data_source_block           jiaxg_1103
_cod_depositor_comments          'Adding full bibliography for 1547881.cif.'
_cod_database_code               1547881
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_olex2_date_sample_data_collection 2016-11-03
_olex2_submission_special_instructions 'No special instructions were received'