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_4034935
_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         'C23 H24 O'
_chemical_formula_sum            'C23 H24 O'
_chemical_formula_weight         316.42
_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             2017-05-11
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
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_cell_angle_alpha                100.526(5)
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_cell_formula_units_Z            2
_cell_length_a                   9.5076(6)
_cell_length_b                   10.1735(7)
_cell_length_c                   11.0649(6)
_cell_measurement_reflns_used    4179
_cell_measurement_temperature    294.5(5)
_cell_measurement_theta_max      72.4730
_cell_measurement_theta_min      4.5110
_cell_volume                     863.75(12)
_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
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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)'
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_diffrn_detector                 'CCD plate'
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_diffrn_measured_fraction_theta_max 0.980
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;
  1 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000  -30.0000 67

  2 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000  -90.0000 84

  3 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000  -60.0000 95

  4 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000  120.0000 67

  5 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -38.0000  -60.0000 88

  6 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   19.0000  120.0000 101

  7 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000 -180.0000 95

  8 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000 -180.0000 84

  9 omega   38.00   91.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 10 omega   38.00  116.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 11 omega   39.00  109.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

 12 omega   38.00   91.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 13 omega   38.00   91.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 14 omega   40.00   98.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

 15 omega   38.00   91.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 16 omega   39.00  109.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 70

 17 omega   38.00   91.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 18 omega   87.00  178.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 91

 19 omega   38.00  116.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 78

 20 omega   40.00  135.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 95

 21 omega  100.00  178.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 78

 22 omega   40.00  135.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 95

 23 omega   70.00  178.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 108

 24 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000  150.0000 84

 25 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -38.0000   30.0000 88

 26 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000   30.0000 95

 27 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000 -180.0000 84

 28 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000   90.0000 84

 29 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   38.0000 -120.0000 88

 30 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000   90.0000 95

 31 omega   70.00  144.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 74
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.1186102000
_diffrn_orient_matrix_UB_12      0.1546604000
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_diffrn_orient_matrix_UB_21      0.1565855000
_diffrn_orient_matrix_UB_22      0.0056476000
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_diffrn_orient_matrix_UB_31      0.0194413000
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_diffrn_orient_matrix_UB_33      -0.1171904000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0262
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_diffrn_reflns_limit_h_max       11
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_diffrn_reflns_theta_min         4.523
_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44029
_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
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_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description
;
;
_exptl_crystal_F_000             340
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_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.241
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_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         3365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0686
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1103P)^2^+0.0759P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                2896
_reflns_number_total             3365
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           ch-htt-371_cmpd_5n
_cod_original_cell_volume        863.74(10)
_cod_database_code               4034935
_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:
 C004(H004), C007(H007), C00A(H00A), C00C(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00D,H00E), C00K(H00N,H00O), C00L(H00P,H00Q)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00E(H00F), C00F(H00G), C00G(H00H), C00H(H00I), C00J(H00M),
 C00N(H00U), C00O(H00V)
2.d Idealised Me refined as rotating group:
 C00I(H00J,H00K,H00L), C00M(H00R,H00S,H00T)
;
_shelx_res_checksum              74969
_shelx_hkl_checksum              87903
_olex2_date_sample_data_collection 2017-05-09
_olex2_submission_special_instructions 'No special instructions were received'