Catalytic Asymmetric Synthesis of Acyclic Arrays by Tandem 1,4-Addition-Aldol Reactions
Gareth P. Howell; Stephen P. Fletcher; Koen Geurts; Bjorn ter Horst; Ben L. Feringa; Journal of the American Chemical Society 128 (2006) 14977–14985; doi:10.1021/ja0651862

data_4111099
_publ_contact_author_address
;
     Crystal Structure Center,
     Chemical Physics,
     Materials Science Center,
     Groningen University,
     Nijenborgh 4,
     NL-9747 AG Groningen,
     The Netherlands.
;
_publ_contact_author_email       A.Meetsma@rug.nl
_publ_contact_author_fax         '+31 50 3634441'
_publ_contact_author_name
;
   Drs. A. Meetsma
;
_publ_contact_author_phone       '+31 50 3634368'
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Acyclic Arrays by Tandem
 1,4-Addition-Aldol Reactions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14977
_journal_page_last               14985
_journal_paper_doi               10.1021/ja0651862
_journal_volume                  128
_journal_year                    2006
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C18 H20 O3'
_chemical_formula_sum            'C18 H20 O3'
_chemical_formula_weight         284.35
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_date             '2006-01-02  09:40:52'
_audit_creation_method
;
 PLATON <TABLE ACC> option    (version :: 110805)
 SHELXL97-2 & Manual Editing 
;
_audit_update_record
;
 ?
;
_cell_angle_alpha                90
_cell_angle_beta                 100.106(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.066(4)
_cell_length_b                   5.706(1)
_cell_length_c                   13.026(2)
_cell_measurement_reflns_used    4246
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.30
_cell_volume                     1541.5(5)
_computing_cell_refinement       'SAINTPLUS, Version 6.02A, (Bruker, 2000)'
_computing_data_collection       'SMART, Version 5.624, (Bruker, 2001)'
_computing_data_reduction        'XPREP, Version 5.1/NT, (Bruker, 2000)'
_computing_molecular_graphics
;
 PLUTO (Meetsma, 2005) 
 PLATON (Spek, 2003)
;
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
 SIR2004 (Burla et al., 2005)
;
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean '4096x4096 / 62x62 (binned 512)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
  Bruker Smart Apex; CCD area detector 
;
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_detector
;
  CCD area-detector
;
_diffrn_radiation_monochromator  'parallel mounted graphite'
_diffrn_radiation_source         'fine focus sealed Siemens Mo tube '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5579
_diffrn_reflns_reduction_process
;
 Intensity data were corrected for Lorentz and polarization
  effects, decay and absorption and reduced to F~o~^2^
  using SAINT (Bruker, 2000) and SADABS (Sheldrick, 2001)
;
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_correction_T_min  0.9308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS, Sheldrick, Bruker, 2001))'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       platelet
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
  The absolute configuration could not be determined reliably:
   there are only elements in the structure with very small anomalous effects
   by the used X-ray wavelength, so the Friedel pairs are merged.
 
 The absolute structure is known by synthese route.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.302
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         1558
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.301
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.611
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+3.9028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.1680
_reflns_number_gt                1392
_reflns_number_total             1558
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja0651862si20060720_050542.cif
_cod_data_source_block           Q1067
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4111099
_vrn_publ_code_squeezed_elec     0.0
_vrn_publ_code_void_volume       18.1
_vrn_publ_code_frame_time_sec    30.0
_vrn_publ_code_meas_time_hour    18.0