Enantioselective [6π]-Photocyclization Reaction of an Acrylanilide Mediated by a Chiral Host. Interplay between Enantioselective Ring Closure and Enantioselective Protonation
Thorsten Bach; Benjamin Grosch; Thomas Strassner; Eberhardt Herdtweck; Journal of Organic Chemistry 68 (2003) 1107–1116; doi:10.1021/jo026602d

data_4022317
_publ_contact_author
;
        Dr. Eberhardt Herdtweck
        Anorganisch-chemisches Institut der
        Technischen Universit\"at M\"unchen,
        Lichtenbergstrasse 4,
        D-85747 Garching bei M\"unchen,
        Germany.
;
_publ_contact_author_email       eberhardt.herdtweck@ch.tum.de
_publ_contact_author_fax         ' +49(0)89 289 13473'
_publ_contact_author_phone       '+49(0)89 289 13143'
_publ_section_title
;
 Enantioselective [6\p]-Photocyclization Reaction of
 an Acrylanilide Mediated by a Chiral Host. Interplay
 between Enantioselective Ring Closure and
 Enantioselective Protonation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1107
_journal_page_last               1116
_journal_paper_doi               10.1021/jo026602d
_journal_volume                  68
_journal_year                    2003
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C13 H15 N O'
_chemical_formula_sum            'C13 H15 N O'
_chemical_formula_weight         201.26
_chemical_name_systematic
;
  ?
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             29-Jul-02
_audit_creation_method           'PLATON <TABLE ACC> option'
_audit_update_record
;
  29-Jul-02  Updated by the Author E.H.
             Textwriting by E.H.
             Checkcif    OK
  30-Jul-02  Updated by the Author E.H.
;
_cell_angle_alpha                104.554(2)
_cell_angle_beta                 105.514(2)
_cell_angle_gamma                96.646(3)
_cell_formula_units_Z            2
_cell_length_a                   6.3016(3)
_cell_length_b                   8.7289(4)
_cell_length_c                   10.1131(5)
_cell_measurement_reflns_used    1801
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      25.44
_cell_measurement_theta_min      2.19
_cell_volume                     508.73(4)
_computing_cell_refinement       'DENZO (Nonius, 2001b)'
_computing_data_collection       'Kappa-CCD Control Software (Nonius, 2001a)'
_computing_data_reduction        'DENZO (Nonius, 2001b)'
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_publication_material  'PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Kappa CCD (Nonius)'
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'NONIUS FR 591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7241
_diffrn_reflns_theta_full        25.44
_diffrn_reflns_theta_max         25.44
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
   Neither decay correction nor absorption correction necessary
  Denzo-SNM; Scale-Pack (Nonius, 2001b)'
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       fragment
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         1873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+0.0883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1167
_reflns_number_gt                1600
_reflns_number_total             1873
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026602dsi20021114_030548.cif
_cod_data_source_block           BACD-4124-173
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4022317