Allylic Alcohol Synthesis by Ni-Catalyzed Direct and Selective Coupling of Alkynes and Methanol
chen, Herong; Zhou, Zhijun; Kong, Wangqing; Chemical Science  (2021) –; doi:10.1039/D1SC02625A

data_1563206
_publ_section_title
;
 Allylic Alcohol Synthesis by Ni-Catalyzed Direct and Selective Coupling
 of Alkynes and Methanol
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02625A
_journal_year                    2021
_chemical_formula_moiety         'C16 H18 O3'
_chemical_formula_sum            'C16 H18 O3'
_chemical_formula_weight         258.30
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-23
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2021-01-23 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.989(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8774(4)
_cell_length_b                   11.4152(4)
_cell_length_c                   13.2381(5)
_cell_measurement_reflns_used    4198
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      69.40
_cell_measurement_theta_min      5.01
_cell_volume                     1334.19(9)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7918
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        64.990
_diffrn_reflns_theta_max         64.990
_diffrn_reflns_theta_min         5.009
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6584
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0102(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0424P)^2^+0.2820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0901
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1919
_reflns_number_total             2166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02625a2.cif
_cod_data_source_block           cu_190522c_0m
_cod_database_code               1563206
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.920
_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 Secondary CH2 refined with riding coordinates: 
 C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7) 
2.c Idealised Me refined as rotating group: 
 C16(H16A,H16B,H16C) 
2.d Idealised tetrahedral OH refined as rotating group: 
 O2(H2) 
;
_olex2_submission_special_instructions 'No special instructions were received'