Modular and stereoselective synthesis of tetrasubstituted helical alkenes via a palladium-catalyzed domino reaction.
Liu, Hongqiang; El-Salfiti, Mohamed; Chai, David I.; Auffret, Jérémy; Lautens, Mark; Organic letters 14 (2012) 3648–3651; doi:10.1021/ol301495q

data_1508295
_publ_section_title
;
 Modular and stereoselective synthesis of tetrasubstituted helical alkenes
 via a palladium-catalyzed domino reaction.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3648
_journal_page_last               3651
_journal_paper_doi               10.1021/ol301495q
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C26 H27 N O2'
_chemical_formula_sum            'C26 H27 N O2'
_chemical_formula_weight         385.49
_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                98.774(2)
_cell_angle_beta                 99.335(2)
_cell_angle_gamma                110.505(1)
_cell_formula_units_Z            2
_cell_length_a                   9.6278(3)
_cell_length_b                   9.9460(3)
_cell_length_c                   11.6593(4)
_cell_measurement_reflns_used    7905
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.62
_cell_measurement_theta_min      5.54
_cell_volume                     1005.06(6)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_source         'Bruker ImuS'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9686
_diffrn_reflns_theta_full        66.61
_diffrn_reflns_theta_max         66.61
_diffrn_reflns_theta_min         5.53
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0676P)^2^+0.6193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                3213
_reflns_number_total             3360
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol301495q_si_002.cif
_cod_data_source_block           d12160
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

 Adding full bibliography for 1508294--1508295.cif.
;
_cod_database_code               1508295