Nickel-catalyzed hydroimination of alkynes.
Manan, Rajith S.; Kilaru, Praveen; Zhao, Pinjing; Journal of the American Chemical Society 137 (2015) 6136–6139; doi:10.1021/jacs.5b02272

data_4123566
_publ_section_title
;
 Nickel-catalyzed hydroimination of alkynes.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6136
_journal_page_last               6139
_journal_paper_doi               10.1021/jacs.5b02272
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C19 H21 N'
_chemical_formula_sum            'C19 H21 N'
_chemical_formula_weight         263.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.4765(7)
_cell_length_b                   7.6816(5)
_cell_length_c                   29.8008(18)
_cell_measurement_reflns_used    5912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.237
_cell_measurement_theta_min      5.939
_cell_volume                     3085.0(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            10172
_diffrn_reflns_point_group_measured_fraction_full 0.795
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.555
_diffrn_reflns_theta_min         5.939
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.491
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0880 before and 0.0382 after correction.
The Ratio of minimum to maximum transmission is 0.8673.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4442
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0594P)^2^+0.5696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_full    0.641
_reflns_Friedel_fraction_max     0.660
_reflns_number_gt                4040
_reflns_number_total             4442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b02272_si_003.cif
_cod_data_source_block           pna21
_cod_depositor_comments
'Adding full bibliography for 4123566--4123653.cif.'
_cod_database_code               4123566
_shelxl_version_number           2014-3
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B), C27(H27A,H27B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C0AA(H0AA), C3(H3), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C26(H26), C29(H29),
  C30(H30), C31(H31), C35(H35), C36(H36), C37(H37), C38(H38)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C28(H28A,H28B,H28C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              60402
_shelx_hkl_checksum              82041
_olex2_date_sample_data_collection 'Dec 16, 2014'
_olex2_date_sample_submission    'Dec 16, 2014'
_olex2_submission_special_instructions 'No special instructions were received'