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_4034937
_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 H24 O S'
_chemical_formula_sum            'C26 H24 O S'
_chemical_formula_weight         384.51
_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     dual
_audit_creation_date             2017-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.009(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1052(4)
_cell_length_b                   10.7198(4)
_cell_length_c                   17.6163(6)
_cell_measurement_reflns_used    4180
_cell_measurement_temperature    294.2(4)
_cell_measurement_theta_max      72.0490
_cell_measurement_theta_min      4.2590
_cell_volume                     2034.77(13)
_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      294.2(4)
_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 0.978
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000  150.0000 74

  2 omega   23.00   90.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000  -60.0000 67

  3 omega    1.00   75.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000   30.0000 74

  4 omega   23.00   90.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000  120.0000 67

  5 omega   20.00  104.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000   60.0000 84

  6 omega  -35.00   66.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -19.0000  150.0000 101

  7 omega   38.00   91.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

  8 omega   40.00   98.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

  9 omega   41.00  126.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 85

 10 omega   91.00  176.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 85

 11 omega   40.00   98.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 12 omega   91.00  176.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 85

 13 omega   40.00   98.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 14 omega   38.00   91.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 15 omega   38.00  116.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 16 omega   20.00  104.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000  -60.0000 84

 17 omega   20.00   65.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000  120.0000 45

 18 omega   18.00  103.00   1.0000    2.8200
omega____ theta____ kappa____ phi______ frames
    -       36.4171   62.0000 -179.0000 85
;
_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      0.0600785000
_diffrn_orient_matrix_UB_12      -0.0389395000
_diffrn_orient_matrix_UB_13      0.0849150000
_diffrn_orient_matrix_UB_21      -0.0831452000
_diffrn_orient_matrix_UB_22      0.0939600000
_diffrn_orient_matrix_UB_23      0.0298401000
_diffrn_orient_matrix_UB_31      -0.0995546000
_diffrn_orient_matrix_UB_32      -0.1015480000
_diffrn_orient_matrix_UB_33      -0.0050240000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11570
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.618
_diffrn_reflns_theta_min         4.288
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.499
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57460
_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    1.255
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.056
_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     256
_refine_ls_number_reflns         3957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0719
_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^)+(0.1219P)^2^+0.4842P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1804
_refine_ls_wR_factor_ref         0.1916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3298
_reflns_number_total             3957
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00150_si_002.cif
_cod_data_source_block           ch-htt-410_cmpd_5w
_cod_database_code               4034937
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.82
_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. Shared sites
{C003, S0}
{S001, C0}
3. Uiso/Uaniso restraints and constraints
Uanis(C003) = Uanis(S0)
Uanis(S0) = Uanis(C003)
Uanis(S001) = Uanis(C0)
Uanis(C0) = Uanis(S001)
4. Others
 Sof(H00U)=Sof(S0)=1-FVAR(1)
 Sof(S001)=Sof(H00V)=FVAR(1)
 Sof(H00W)=Sof(C0)=Sof(H0)=1-FVAR(2)
 Sof(C003)=Sof(H003)=Sof(H00T)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C008(H008), C009(H009), C00H(H00H), C00K(H00K)
5.b Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00C), C00L(H00E,H00I), C00O(H00P,H00Q)
5.c Aromatic/amide H refined with riding coordinates:
 C003(H003), C00B(H00B), C00D(H00D), C00F(H00F), C00G(H00G), C00J(H00J),
 C00M(H00M), C00P(H00R), C00Q(H00S), C00R(H00T), C00R(H00U), C00S(H00V),
 C00S(H00W), C0(H0)
5.d Idealised Me refined as rotating group:
 C00N(H00L,H00N,H00O)
;
_shelx_res_checksum              68554
_shelx_hkl_checksum              13298
_olex2_submission_special_instructions 'No special instructions were received'