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_1553169
_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         'C33 H41 N O9'
_chemical_formula_sum            'C33 H41 N O9'
_chemical_formula_weight         595.67
_chemical_name_systematic        'alkyne amide'
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2014-08-29 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.206(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7518(3)
_cell_length_b                   17.4971(5)
_cell_length_c                   20.0458(7)
_cell_measurement_reflns_used    3362
_cell_measurement_temperature    298.5(2)
_cell_measurement_theta_max      70.0530
_cell_measurement_theta_min      5.1430
_cell_volume                     3355.17(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
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  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      298.5(2)
_diffrn_detector_area_resol_mean 16.0450
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega  -49.00   19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -60.0000 68

  2 omega    3.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 31

  3 omega   69.00  123.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 54

  4 omega  -15.00   53.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -180.0000 68

  5 omega   73.00  123.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 50

  6 omega  -13.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   90.0000 76

  7 omega  -14.00   18.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000    0.0000 32

  8 omega   51.00   79.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 28

  9 omega   44.00  125.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  120.0000 81

 10 omega   47.00   93.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 46

 11 omega   49.00   86.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 37

 12 omega   35.00   87.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 52

 13 omega   37.00   93.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 56

 14 omega   34.00   83.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 49

 15 omega   60.00  104.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 44

 16 omega   75.00  178.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000   30.0000 103

 17 omega   34.00   66.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000   30.0000 32
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0912926000
_diffrn_orient_matrix_UB_12      0.0722284000
_diffrn_orient_matrix_UB_13      0.0144470000
_diffrn_orient_matrix_UB_21      -0.0317034000
_diffrn_orient_matrix_UB_22      0.0196848000
_diffrn_orient_matrix_UB_23      -0.0763896000
_diffrn_orient_matrix_UB_31      -0.1287842000
_diffrn_orient_matrix_UB_32      0.0463253000
_diffrn_orient_matrix_UB_33      0.0099588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11896
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         4.50
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89885
_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_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.226
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+3.1076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1931
_refine_ls_wR_factor_ref         0.2060
_reflns_number_gt                3562
_reflns_number_total             5840
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00205b2.cif
_cod_data_source_block           xuzhenghu
_cod_original_cell_volume        3355.18(17)
_cod_database_code               1553169
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 98.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C4(H4A,H4B), C12(H12A,H12B), C15(H15A,H15B), C22(H22A,H22B), C31(H31A,H31B),
 C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C8(H8), C10(H10), C25(H25)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,
 H9B,H9C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'