Palladium-Catalyzed Domino Reaction for Stereoselective Synthesis of Multisubstituted Olefins: Construction of Blue Luminogens.
Hao, Tao-Tao; Liang, Hao-Ran; Ou-Yang, Ying-Han; Yin, Chang-Zhen; Zheng, Xue-Li; Yuan, Mao-Lin; Li, Rui-Xiang; Fu, Hai-Yan; Chen, Hua; The Journal of organic chemistry 83 (2018) 4441–4454; doi:10.1021/acs.joc.8b00150

data_4034938
_publ_section_title
;
 Palladium-Catalyzed Domino Reaction for Stereoselective Synthesis of
 Multisubstituted Olefins: Construction of Blue Luminogens.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4441
_journal_page_last               4454
_journal_paper_doi               10.1021/acs.joc.8b00150
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C26 H25 O'
_chemical_formula_sum            'C26 H25 O'
_chemical_formula_weight         353.46
_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     direct
_audit_creation_date             2017-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                99.769(4)
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_cell_angle_gamma                109.258(6)
_cell_formula_units_Z            2
_cell_length_a                   8.8859(6)
_cell_length_b                   9.9045(6)
_cell_length_c                   11.8557(6)
_cell_measurement_reflns_used    4835
_cell_measurement_temperature    294.24(10)
_cell_measurement_theta_max      72.1940
_cell_measurement_theta_min      5.5560
_cell_volume                     955.59(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.24(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  150.0000 84

  2 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000    0.0000 84

  3 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000   60.0000 66

  4 omega    7.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   19.0000  150.0000 100

  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000 -150.0000 84

  6 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  -60.0000 66

  7 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000   90.0000 66

  8 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000    0.0000 66

  9 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000 -180.0000 66

 10 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 11 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

 12 omega   40.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 95

 13 omega   91.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 14 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

 15 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 16 omega   40.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 95

 17 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 18 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

 19 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 20 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 21 omega   38.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 22 omega   39.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -120.0000 138

 23 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -60.0000 84

 24 omega  -35.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -19.0000    0.0000 100

 25 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000 -150.0000 95

 26 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000   60.0000 95

 27 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000  -60.0000 88

 28 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000  150.0000 95

 29 omega   70.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0921109000
_diffrn_orient_matrix_UB_12      0.0489030000
_diffrn_orient_matrix_UB_13      0.1262548000
_diffrn_orient_matrix_UB_21      -0.1613384000
_diffrn_orient_matrix_UB_22      -0.0245907000
_diffrn_orient_matrix_UB_23      0.0447305000
_diffrn_orient_matrix_UB_31      -0.0170291000
_diffrn_orient_matrix_UB_32      -0.1597285000
_diffrn_orient_matrix_UB_33      0.0008060000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9204
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.236
_diffrn_reflns_theta_min         4.847
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             378
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0630
_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^)+(0.1265P)^2^+0.1752P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1832
_refine_ls_wR_factor_ref         0.1890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3244
_reflns_number_total             3687
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00150_si_002.cif
_cod_data_source_block           ch-htt-4472_cmpd_6f
_cod_original_cell_volume        955.60(10)
_cod_database_code               4034938
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.88
_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 Ternary CH refined with riding coordinates:
 C002(H002), C005(H005), C007(H007), C00A(H00A), C00G(H00G), C00H(H00H)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00D(H00D), C00E(H00E), C00F(H00F), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P)
2.d Idealised Me refined as rotating group:
 C00Q(H00O,H00Q,H00R), C00R(H00S,H00T,H00U)
;
_olex2_date_sample_data_collection 2017-11-16
_olex2_submission_special_instructions 'No special instructions were received'