An Approach to Mimicking the Sesquiterpene Cyclase Phase by Nickel-Promoted Diene/Alkyne Cooligomerization
Dane Holte; Daniel C. G. Götz; Phil S. Baran; Journal of Organic Chemistry 77 (2012) 825–842; doi:10.1021/jo202314a

data_4026904
_publ_section_title
;
 An Approach to Mimicking the Sesquiterpene Cyclase Phase by
 Nickel-Promoted Diene/Alkyne Cooligomerization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              825
_journal_page_last               842
_journal_paper_doi               10.1021/jo202314a
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C18 H30 O3'
_chemical_formula_weight         294.42
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.998(3)
_cell_angle_beta                 92.490(3)
_cell_angle_gamma                98.515(3)
_cell_formula_units_Z            2
_cell_length_a                   5.5789(3)
_cell_length_b                   11.6219(6)
_cell_length_c                   13.0202(6)
_cell_measurement_reflns_used    5070
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.94
_cell_measurement_theta_min      3.86
_cell_volume                     830.35(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirror'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8092
_diffrn_reflns_theta_full        60.00
_diffrn_reflns_theta_max         66.20
_diffrn_reflns_theta_min         3.86
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.9525
_exptl_absorpt_correction_T_min  0.7696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       Needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0508
_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^)+(0.0818P)^2^+0.3908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                2194
_reflns_number_total             2527
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202314a_si_003.cif
_cod_data_source_block           Baran198
_cod_database_code               4026904