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_4034939
_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 H26 O'
_chemical_formula_sum            'C26 H26 O'
_chemical_formula_weight         354.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.897(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6446(4)
_cell_length_b                   7.3696(2)
_cell_length_c                   23.0316(8)
_cell_measurement_reflns_used    5010
_cell_measurement_temperature    294.05(10)
_cell_measurement_theta_max      72.3890
_cell_measurement_theta_min      6.2820
_cell_volume                     1969.27(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      294.05(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 0.977
_diffrn_measurement_details
;
  1 omega    1.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   91.0000   43.8793 28

  2 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921  -99.0000 -180.0000 74

  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921  -99.0000  -90.0000 74

  4 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921 -125.0000 -150.0000 66

  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921  -57.0000  -60.0000 84

  6 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   57.0000 -120.0000 84

  7 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921 -125.0000 -120.0000 66

  8 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   57.0000 -180.0000 84

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

 10 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 11 omega  100.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 78

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

 13 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 14 omega   91.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 85

 15 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

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

 17 omega   67.00  160.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  165.0000  -21.0000 93

 18 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   57.0000   90.0000 84

 19 omega  -31.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921  -57.0000   60.0000 43

 20 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   38.0000    0.0000 88
;
_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      0.0848388000
_diffrn_orient_matrix_UB_12      0.0221867000
_diffrn_orient_matrix_UB_13      0.0546084000
_diffrn_orient_matrix_UB_21      0.0900602000
_diffrn_orient_matrix_UB_22      0.0815639000
_diffrn_orient_matrix_UB_23      -0.0377636000
_diffrn_orient_matrix_UB_31      -0.0482790000
_diffrn_orient_matrix_UB_32      0.1912040000
_diffrn_orient_matrix_UB_33      0.0098045000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11217
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.807
_diffrn_reflns_theta_min         6.308
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.540
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57632
_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    1.196
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0635
_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^)+(0.1118P)^2^+0.3298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1712
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3272
_reflns_number_total             3817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00150_si_002.cif
_cod_data_source_block           ch-htt-4471_cmpd_6g
_cod_original_cell_volume        1969.26(11)
_cod_database_code               4034939
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.87
_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), C008(H008), C009(H009), C00I(H00I), C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00B,H00C), C00O(H00P,H00Q)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00N(H00O), C00P(H00R), C00Q(H00S)
2.d Idealised Me refined as rotating group:
 C00M(H00F,H00M,H00N), C00R(H00T,H00U,H00V)
;
_olex2_date_sample_data_collection 2017-12-06
_olex2_submission_special_instructions 'No special instructions were received'