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_4034936
_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         'C31 H25 Cl'
_chemical_formula_sum            'C31 H25 Cl'
_chemical_formula_weight         432.96
_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             2017-06-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.90789(18)
_cell_length_b                   19.4213(4)
_cell_length_c                   11.7413(2)
_cell_measurement_reflns_used    9670
_cell_measurement_temperature    296.31(10)
_cell_measurement_theta_max      72.2500
_cell_measurement_theta_min      4.3910
_cell_volume                     2259.29(7)
_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
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_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000    0.0000 67

  2 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -150.0000 88

  3 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -180.0000 67

  4 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

  5 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  150.0000 88

  6 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -150.0000 94

  7 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -120.0000 94

  8 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  -90.0000 88

  9 omega   38.00   91.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 10 omega   91.00  176.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 85

 11 omega   38.00  116.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 78

 12 omega   41.00  126.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   30.0000 85

 13 omega   40.00   98.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 14 omega   39.00  109.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 15 omega   38.00   91.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 16 omega   38.00  116.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 78

 17 omega   39.00  109.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

 18 omega   38.00   91.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 19 omega   38.00   91.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 20 omega   38.00   91.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 21 omega   88.00  178.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   33.0000  -46.2972 90

 22 omega   39.00  109.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 23 omega   40.00  135.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 95

 24 omega   37.00  146.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  120.0000 109

 25 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -30.0000 84

 26 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000    0.0000 94

 27 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000   30.0000 88

 28 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000   90.0000 88

 29 omega    0.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   94.0000 -124.8471 26

 30 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   30.0000 74

 31 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  150.0000 94

 32 omega   70.00  125.00   1.0000    3.7200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 55
;
_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      -0.0597515000
_diffrn_orient_matrix_UB_12      -0.0653920000
_diffrn_orient_matrix_UB_13      0.0543848000
_diffrn_orient_matrix_UB_21      0.0099829000
_diffrn_orient_matrix_UB_22      -0.0375035000
_diffrn_orient_matrix_UB_23      -0.1152591000
_diffrn_orient_matrix_UB_31      0.1432464000
_diffrn_orient_matrix_UB_32      -0.0246055000
_diffrn_orient_matrix_UB_33      0.0312443000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24879
_diffrn_reflns_point_group_measured_fraction_full 1.000
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.733
_diffrn_reflns_theta_min         4.400
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64754
_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
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_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_refine_diff_density_max         1.117
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0706
_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^)+(0.1252P)^2^+1.1996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2044
_refine_ls_wR_factor_ref         0.2083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4075
_reflns_number_total             4456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00150_si_002.cif
_cod_data_source_block           ch-htt-1111_cmpd_5v
_cod_original_cell_volume        2259.29(8)
_cod_database_code               4034936
_reflns_odcompleteness_completeness 99.95
_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
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00A(H00A), C00G(H00G), C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00B,H00N), C00P(H00P,H00Q), C00R(H00R,H00S)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O), C00S(H00T), C00T(H00U),
 C00U(H00V), C00V(H00W), C00W(H00X)
;
_shelx_res_checksum              30195
_shelx_hkl_checksum              24946
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-06-15
_olex2_submission_special_instructions 'No special instructions were received'