An Enantioselective Synthetic Route toward Second-Generation Light-Driven Rotary Molecular Motors
Thomas C. Pijper; Dirk Pijper; Michael M. Pollard; Frédéric Dumur; Stephen G. Davey; Auke Meetsma; Ben L. Feringa; Journal of Organic Chemistry 75 (2010) 825–838; doi:10.1021/jo902348u

data_4025199
_publ_contact_author_address
;
  Crystal Structure Center, Chemical Physics,
  Zernike Institute for Advanced Materials,
  University of Groningen,
  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_related_literature
;
;
_publ_section_title
;
 An Enantioselective Synthetic Route toward Second-Generation Light-Driven
 Rotary Molecular Motors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              825
_journal_page_last               838
_journal_paper_doi               10.1021/jo902348u
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C27 H20 O S'
_chemical_formula_sum            'C27 H20 O S'
_chemical_formula_weight         392.52
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   direct
_audit_creation_date             '2008-02-13  11:39:24'
_audit_creation_method
;
 PLATON <TABLE ACC> option    (version ::  91007)
 SHELXL97-2 & Manual Editing 
;
_audit_update_record
;
 ?
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7954(15)
_cell_length_b                   14.349(3)
_cell_length_c                   17.845(4)
_cell_measurement_reflns_used    2645
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.69
_cell_volume                     1996.1(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2006)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics
;
 PLATON (Spek, 2003)
 PLUTO (Meetsma, 2007) 
;
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
 DIRDIF-07 (Beurskens et al., 2007)
;
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 66.06
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
  Bruker Smart Apex; CCD area detector 
;
_diffrn_measurement_method       '\f and \w 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  0.0725
_diffrn_reflns_av_sigmaI/netI    0.0742
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14068
_diffrn_reflns_reduction_process
;
 Intensity data were corrected for Lorentz and polarization
  effects, decay and absorption and reduced to F~o~^2^
  using SAINT-Plus & SADABS (Bruker, 2007).
;
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_correction_T_min  0.9397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS, (Bruker, 2006))'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cut_fragment
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
  The absolute structure of the molecule actually chosen was
   determined by Flack's x-refinement.

   (Flack & Bernardinelli, 1999, 2000)
;
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0391P)^2^+0.0P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0832
_reflns_number_gt                2696
_reflns_number_total             3526
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo902348u_si_002.cif
_cod_data_source_block           DATNAM
_cod_database_code               4025199
_vrn_publ_code_number_frames     1800
_vrn_publ_code_frame_time_sec    30.0
_vrn_publ_code_meas_time_hour    17.9