Catalytic cross deoxygenative and dehydrogenative coupling of aldehydes and alkenes: a redox-neutral process to produce skipped dienes
Bo Qian; Guoying Zhang; Yongzheng Ding; Hanmin Huang; Chem.Commun. 49 (2013) 9839–; doi:10.1039/c3cc45428b

data_7109895
_publ_section_title
;
 Catalytic cross deoxygenative and dehydrogenative coupling of aldehydes
 and alkenes: a redox-neutral process to produce skipped dienes
;
_journal_name_full               Chem.Commun.
_journal_page_first              9839
_journal_paper_doi               10.1039/c3cc45428b
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C19 H12'
_chemical_formula_sum            'C19 H12'
_chemical_formula_weight         240.29
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-08
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.773(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.5874(3)
_cell_length_b                   6.8977(4)
_cell_length_c                   12.9328(5)
_cell_measurement_reflns_used    3435
_cell_measurement_temperature    100(7)
_cell_measurement_theta_max      72.4234
_cell_measurement_theta_min      6.1921
_cell_volume                     657.38(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      100(7)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9551
_diffrn_measured_fraction_theta_max 0.9456
_diffrn_measurement_details
;
  1 omega  -65.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 31

  2 omega  -80.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   30.0000 45

  3 omega  -69.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  150.0000 41

  4 omega    4.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  150.0000 25

  5 omega  -25.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 45

  6 omega -129.00 -101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000  120.0000 28

  7 omega  -71.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000   57.0000 -120.0000 84

  8 omega  -51.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000  150.0000 26

  9 omega  -88.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  125.0000 -150.0000 43

 10 omega  -53.00  -27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000  120.0000 26

 11 omega   26.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -120.0000 25

 12 omega   73.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -180.0000 55

 13 omega   26.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  150.0000 25

 14 omega   28.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -150.0000 26

 15 omega   27.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -180.0000 26

 16 omega  -50.00    7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   25.0000 -180.0000 57

 17 omega -130.00  -86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -180.0000 44

 18 omega -116.00  -33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000   90.0000 83

 19 omega -100.00  -40.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -63.0000  120.0000 60

 20 omega  -61.00  -31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -150.0000 30

 21 omega -137.00  -96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -150.0000 41

 22 omega  -78.00  -37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -180.0000 41

 23 omega   50.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   60.0000 25

 24 omega   98.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000 -180.0000 33

 25 omega   85.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000 -120.0000 52

 26 omega  138.00  166.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000   90.0000 28

 27 omega   96.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000 -150.0000 26

 28 omega   63.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000   90.0000 38

 29 omega  110.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000   90.0000 27

 30 omega   99.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000  120.0000 50

 31 omega  126.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -180.0000 26

 32 omega   97.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  150.0000 52

 33 omega   84.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -180.0000 27

 34 omega  121.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000   30.0000 51

 35 omega   88.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  150.0000 41

 36 omega   83.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  168.5096 27

 37 omega  122.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000   60.0000 55

 38 omega   83.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000   60.0000 25

 39 omega   85.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000 -180.0000 26

 40 omega   49.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000  -90.0000 49

 41 omega   44.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -90.0000 48

 42 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  120.0000 26

 43 omega   93.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  120.0000 36

 44 omega   44.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  -90.0000 35

 45 omega  140.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   30.0000 38

 46 omega   90.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -150.0000 31

 47 omega   82.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   60.0000 33

 48 omega   44.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   60.0000 33

 49 omega   91.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000   60.0000 33

 50 omega  109.00  134.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -180.0000 25

 51 omega   90.00  128.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -120.0000 38

 52 omega   90.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000   90.0000 40

 53 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000   90.0000 26

 54 omega   91.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000  150.0000 27

 55 omega   85.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -150.0000 27

 56 omega   63.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -30.0000 26

 57 omega   86.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000  120.0000 27

 58 omega   86.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000  150.0000 27

 59 omega  120.00  166.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  168.5096 46

 60 omega  124.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   31.0000  121.4345 25

 61 omega  101.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -12.0000   60.0000 26

 62 omega   80.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   31.0000  121.4345 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1993736000
_diffrn_orient_matrix_UB_12      0.0233831000
_diffrn_orient_matrix_UB_13      0.0055960000
_diffrn_orient_matrix_UB_21      -0.0603169000
_diffrn_orient_matrix_UB_22      -0.0143492000
_diffrn_orient_matrix_UB_23      -0.1222341000
_diffrn_orient_matrix_UB_31      -0.0172226000
_diffrn_orient_matrix_UB_32      -0.2216940000
_diffrn_orient_matrix_UB_33      0.0085332000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5725
_diffrn_reflns_theta_full        72.57
_diffrn_reflns_theta_max         72.57
_diffrn_reflns_theta_min         6.20
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.913
_refine_diff_density_rms         0.201
_refine_ls_extinction_coef       0.07(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   3.220
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      3.220
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0992
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3323
_refine_ls_wR_factor_ref         0.3362
_reflns_number_gt                1349
_reflns_number_total             1402
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc45428b.txt
_cod_data_source_block           exp_618
_cod_database_code               7109895
_reflns_odcompleteness_completeness 95.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H7 of C7, H9 of C9, H6 of C6, H5 of C5, H4 of C4, H12 of C12, H14 of C14,
  H15 of C15, {H10A,H10B} of C10
2. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H12(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C6(H6), C4(H4), C5(H5), C15(H15), C14(H14), C12(H12)
;