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_1511855
_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         'C40 H54'
_chemical_formula_sum            'C40 H54'
_chemical_formula_weight         534.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-11-22
_audit_creation_method
;
  Olex2 1.2
  (compiled Oct 26 2012 17:06:22, GUI svn.r4371)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.06(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.870(2)
_cell_length_b                   9.2819(19)
_cell_length_c                   18.478(4)
_cell_measurement_reflns_used    5638
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4690
_cell_measurement_theta_min      2.0664
_cell_volume                     1690.4(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7586
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.051
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.6194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1311
_reflns_number_gt                2655
_reflns_number_total             2946
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400140n_si_003.cif
_cod_data_source_block           a
_cod_original_cell_volume        1690.3(6)
_cod_database_code               1511855
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H13A(0.036) H13B(0.036) H7(0.041) H8(0.035) H15B(0.043)
 H15A(0.043) H16A(0.067) H16B(0.067) H16C(0.067) H17B(0.043) H17A(0.043)
 H19B(0.038) H19A(0.038) H4(0.059) H5(0.05) H14A(0.07) H14B(0.07) H14C(0.07)
 H20A(0.069) H20B(0.069) H20C(0.069) H3(0.065) H18A(0.081) H18C(0.081)
 H18B(0.081) H1(0.076) H2(0.09)
 Fixed X: H13A(0.2692) H13B(0.417) H7(0.7157) H8(0.571) H15B(0.5441)
 H15A(0.4368) H16A(0.6123) H16B(0.722) H16C(0.642) H17B(0.3263) H17A(0.2536)
 H19B(0.6402) H19A(0.581) H4(1.0344) H5(0.8991) H14A(0.269) H14B(0.1718)
 H14C(0.3208) H20A(0.5023) H20B(0.6638) H20C(0.5717) H3(1.0001) H18A(0.411)
 H18C(0.4933) H18B(0.3442) H1(0.6878) H2(0.8246)
 Fixed Y: H13A(0.5721) H13B(0.5104) H7(0.5461) H8(0.4812) H15B(0.674)
 H15A(0.7921) H16A(0.9376) H16B(0.8173) H16C(0.901) H17B(0.8684) H17A(0.829)
 H19B(0.6573) H19A(0.5458) H4(0.1877) H5(0.3887) H14A(0.3228) H14B(0.3608)
 H14C(0.2987) H20A(0.7442) H20B(0.7461) H20C(0.8519) H3(0.0409) H18A(0.9691)
 H18C(1.0016) H18B(1.0664) H1(0.2932) H2(0.0938)
 Fixed Z: H13A(0.1236) H13B(0.1451) H7(0.4759) H8(0.3477) H15B(0.5078)
 H15A(0.4786) H16A(0.439) H16B(0.4627) H16C(0.523) H17B(0.3956) H17A(0.3187)
 H19B(0.2693) H19A(0.2097) H4(0.4985) H5(0.5131) H14A(0.1073) H14B(0.1712)
 H14C(0.1899) H20A(0.1367) H20B(0.1503) H20C(0.1953) H3(0.3976) H18A(0.2589)
 H18C(0.3341) H18B(0.319) H1(0.3271) H2(0.3129)
;