Construction of octaalkyl-substituted and decasubstituted all-cis-octatetraenes via linear dimerization of 1,4-dicopper-1,3-butadienes and subsequent cross-coupling with halides.
Wei, Junnian; Wang, Zitao; Zhang, Wen-Xiong; Xi, Zhenfeng; Organic letters 15 (2013) 1222–1225; doi:10.1021/ol400140n

data_1511854
_publ_section_title
;
 Construction of octaalkyl-substituted and decasubstituted
 all-cis-octatetraenes via linear dimerization of
 1,4-dicopper-1,3-butadienes and subsequent cross-coupling with halides.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1222
_journal_page_last               1225
_journal_paper_doi               10.1021/ol400140n
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C36 H50'
_chemical_formula_sum            'C36 H50'
_chemical_formula_weight         482.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-02-21
_audit_creation_method
;
  Olex2 1.2
  (compiled Oct 26 2012 17:06:22, GUI svn.r4371)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.903(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9811(5)
_cell_length_b                   14.0204(5)
_cell_length_c                   15.8490(6)
_cell_measurement_reflns_used    7956
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.3390
_cell_measurement_theta_min      4.1150
_cell_volume                     3090.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9203
_diffrn_measurement_details
;
  1 omega   -6.00   88.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       11.5979   77.0000 -120.0000 94

  2 omega  -20.00   54.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       11.5979  -99.0000   30.0000 74

  3 omega  -13.00   81.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       11.5979   57.0000  150.0000 94

  4 omega  -13.00   79.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       11.5979   38.0000   60.0000 92

  5 omega  -35.00   41.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       11.5979  -57.0000  -60.0000 76

  6 omega  -62.00   23.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       11.5979  -57.0000  120.0000 85

  7 omega  -42.00   45.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       11.5979  -77.0000 -120.0000 87

  8 omega  -90.00  -60.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -      -12.3792  155.0000   47.6346 30
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0459493000
_diffrn_orient_matrix_UB_12      -0.0075555000
_diffrn_orient_matrix_UB_13      -0.0141018000
_diffrn_orient_matrix_UB_21      0.0080193000
_diffrn_orient_matrix_UB_22      0.0499635000
_diffrn_orient_matrix_UB_23      0.0001409000
_diffrn_orient_matrix_UB_31      0.0205737000
_diffrn_orient_matrix_UB_32      -0.0026695000
_diffrn_orient_matrix_UB_33      0.0427282000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22308
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.91
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.038
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0330P)^2^+2.8573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                2645
_reflns_number_total             3043
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400140n_si_002.cif
_cod_data_source_block           13feb21a
_cod_original_cell_volume        3090.25(18)
_cod_database_code               1511854
_chemical_oxdiff_formula         'C40 H56'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H17A,H17B} of C17, {H15A,H15B} of C15, {H13A,H13B} of C13, {H11A,H11B} of
  C11, H10 of C10, H9 of C9, H8 of C8, H7 of C7, H6 of C6
 At 1.5 times of:
  {H18A,H18B,H18C} of C18, {H16A,H16B,H16C} of C16, {H14A,H14B,H14C} of C14,
  {H12A,H12B,H12C} of C12
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C15(H15A,H15B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C)
;