Stereoselective Synthesis of Pentasubstituted 1,3-Dienes via Ni-Catalyzed Reductive Coupling of Unsymmetrical Internal Alkynes
Zhou, Zhijun; Chen, Jiachang; chen, Herong; Kong, Wangqing; Chemical Science  (2020) –; doi:10.1039/D0SC04173D

data_1559058
_publ_section_title
;
 Stereoselective Synthesis of Pentasubstituted 1,3-Dienes via Ni-Catalyzed
 Reductive Coupling of Unsymmetrical Internal Alkynes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04173D
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H28 O4, H2 O'
_chemical_formula_sum            'C30 H30 O5'
_chemical_formula_weight         470.54
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-16
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2019-04-02 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6633(2)
_cell_length_b                   19.2862(4)
_cell_length_c                   19.4190(4)
_cell_measurement_reflns_used    8315
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.28
_cell_measurement_theta_min      5.12
_cell_volume                     2495.53(10)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0962
_diffrn_reflns_av_unetI/netI     0.1018
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9459
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        64.970
_diffrn_reflns_theta_max         64.970
_diffrn_reflns_theta_min         5.121
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.3549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.1966 before and 0.1006 after correction. 
The Ratio of minimum to maximum transmission is 0.4713. 
The \l/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details
; 
 Flack x determined using 1249 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0926
_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^)+(0.1839P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2421
_refine_ls_wR_factor_ref         0.2483
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                3673
_reflns_number_total             4089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04173d2.cif
_cod_data_source_block           cu_190113a_0m
_cod_database_code               1559058
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.923
_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, All O(H,H) groups 
2.a Riding coordinates: 
 O5(H5A,H5B) 
2.b Secondary CH2 refined with riding coordinates: 
 C7(H7A,H7B), C17(H17A,H17B), C22(H22A,H22B), C23(H23A,H23B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C3(H3), C4(H4), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), 
 C26(H26), C27(H27), C28(H28), C29(H29), C30(H30) 
2.d Idealised Me refined as rotating group: 
 C6(H6A,H6B,H6C), C24(H24A,H24B,H24C) 
2.e Idealised tetrahedral OH refined as rotating group: 
 O3(H3A) 
;
_olex2_submission_special_instructions 'No special instructions were received'