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_7109894
_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         'C35 H27 Cl'
_chemical_formula_sum            'C35 H27 Cl'
_chemical_formula_weight         483.02
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-26
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                88.880(9)
_cell_angle_beta                 71.972(12)
_cell_angle_gamma                65.771(10)
_cell_formula_units_Z            2
_cell_length_a                   9.9726(12)
_cell_length_b                   11.8001(9)
_cell_length_c                   12.7945(18)
_cell_measurement_reflns_used    2870
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0010
_cell_measurement_theta_min      3.6110
_cell_volume                     1295.5(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.8741
_diffrn_measurement_details
;
  1 omega  -17.00   16.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -99.0000 -180.0000 22

  2 omega  -13.00   20.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -99.0000   30.0000 22

  3 omega   72.00   99.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000 -120.0000 18

  4 omega    0.00   90.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000   30.0000 60

  5 omega  -34.00   92.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   19.0000 -150.0000 84

  6 omega  -46.00   48.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000 -120.0000 63
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0674461000
_diffrn_orient_matrix_UB_12      -0.0288007000
_diffrn_orient_matrix_UB_13      0.0158465000
_diffrn_orient_matrix_UB_21      -0.0477410000
_diffrn_orient_matrix_UB_22      0.0099328000
_diffrn_orient_matrix_UB_23      0.0561910000
_diffrn_orient_matrix_UB_31      -0.0013834000
_diffrn_orient_matrix_UB_32      -0.0590364000
_diffrn_orient_matrix_UB_33      -0.0064633000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8982
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.18
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5267
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0338P)^2^+0.2323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                3688
_reflns_number_total             5267
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc45428b.txt
_cod_data_source_block           huaws0323_3
_cod_database_code               7109894
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H12 of C12, H11 of C11, H8 of C8, H7 of C7, H5 of C5, H4 of C4, H3 of C3,
  H1 of C1, H13 of C13, H29 of C29, H31 of C31, H32 of C32, H33 of C33, H34 of
  C34, H35 of C35, H14 of C14, H15 of C15, H17 of C17, H18 of C18, H19 of C19,
  H20 of C20, H21 of C21, H22 of C22, H25 of C25, H26 of C26, H27 of C27, H28
  of C28
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32),
 C33(H33), C34(H34), C35(H35)
;