Successive Cu/Pd transmetalation relay catalysis in stereoselective synthesis of tetraarylethenes
Song, Chuanling; Sun, Yihua; Wang, Jianwu; Chen, Hui; Yao, Jiannian; Tung, Chen-Ho; Xu, Zhenghu; Organic Chemistry Frontiers 2 (2015) 1366–; doi:10.1039/C5QO00205B

data_1553167
_publ_section_title
;
 Successive Cu/Pd transmetalation relay catalysis in stereoselective
 synthesis of tetraarylethenes
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1366
_journal_paper_doi               10.1039/C5QO00205B
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety         'O3, C40 H32 O8'
_chemical_formula_sum            'C25 H0 N24 O0.5'
_chemical_formula_weight         644.49
_chemical_name_systematic        alkyne-phenyl
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2014-08-29 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                68.085(14)
_cell_angle_beta                 67.898(13)
_cell_angle_gamma                73.316(14)
_cell_formula_units_Z            2
_cell_length_a                   10.974(9)
_cell_length_b                   13.036(10)
_cell_length_c                   14.337(11)
_cell_measurement_reflns_used    2049
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.335
_cell_measurement_theta_min      2.176
_cell_volume                     1737(2)
_computing_data_reduction        'SAINT v7.23A (Bruker, 2003)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8493
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         5986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0716
_refine_ls_shift/su_max          2.714
_refine_ls_shift/su_mean         0.082
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1284P)^2^+0.6139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2036
_refine_ls_wR_factor_ref         0.2373
_reflns_number_gt                3750
_reflns_number_total             5986
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00205b2.cif
_cod_data_source_block           p
_cod_original_formula_sum        'C25 H0 N24 O0.50'
_cod_database_code               1553167
_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 Aromatic/amide H refined with riding coordinates:
 C29(H29), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20), C22(H22),
  C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C21(H21A,H21B,
 H21C)
;