Stereochemistry of intramolecular Diels?Alder furan (IMDAF) reactions of furyl-substituted chiral ethanolamides
Tromp, Reynier A.; Brussee, Johannes; van der Gen, Arne; Organic & Biomolecular Chemistry 1 (2003) 3592–; doi:10.1039/b307275d

data_7151540
_publ_section_title
;
 Stereochemistry of intramolecular Diels?Alder furan (IMDAF) reactions
 of furyl-substituted chiral ethanolamides
;
_journal_issue                   20
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              3592
_journal_paper_doi               10.1039/b307275d
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C23 H33 N O3 Si'
_chemical_formula_weight         399.22
_chemical_name_systematic
;
(1S,2S,3S,6R,8S)-4-Benzyl-2-O-(tert-butyldimethylsilyl)-3-methyl-11-oxa-4-aza-
tricyclo-[6.2.1.01.6] undec-9-en-5-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   calculated
_atom_sites_solution_primary     DIRDIF
_atom_sites_solution_secondary   xtal_fourr
_audit_creation_date             01-06-14
_audit_creation_method           from_xtal_archive_file_using_CIFIO
_audit_update_record
;
compound synthesized by Reynier A. Tromp
22feb01   measurement by S. Gorter
14jun01   structure refinement by W.L. Driessen
solution by DIRDIF, refinement by XTAL3.4
positions of all non-H refined
all nonH refined anisotropically
H atoms placed at distance of 0.95 from parent atom
H positions not refined, fixed isotropic thermal parameter

P.T. Beurskens, G. Admiraal, G. Beurskens, W.P. Bosman, S. Garcia-Granda,
R.O. Gould, J.M.M. Smits and C. Smykalla.
The DIRDIF program system.
Technical Report of the Crystallography Laboratory, University of Nijmegen,
The Netherlands, 1992.

S.R. Hall, G.S.D. King and J.M. Stewart, XTAL3.4 Users Manual.
Universities of Western Australia and Maryland, 1995.

A.J.C. Wilson, Ed., International Tables for Crystallography, Volume C,
Kluwer Academic Publishers, Dordrecht, The Netherlands, 1992.

A.L. Spek, PLATON, A multipurpose crystallographic tool.
Utrecht University, The Netherlands, 2000.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   19.214(6)
_cell_length_b                   16.341(4)
_cell_length_c                   7.1838(9)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    145
_cell_measurement_theta_max      11.7
_cell_measurement_theta_min      10.0
_cell_volume                     2255.5(9)
_computing_cell_refinement       'Enraf Nonius CAD4'
_computing_data_collection       'Enraf Nonius CAD4'
_computing_data_reduction        'Enraf Nonius CAD4'
_computing_molecular_graphics    Platon
_computing_publication_material  Platon
_computing_structure_refinement  xtal3.4
_computing_structure_solution    DIRDIF
_diffrn_ambient_temperature      145
_diffrn_measurement_method       omega/theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         xray_tube
_diffrn_radiation_type           'Mo K alpha'
_diffrn_radiation_wavelength     0.710730
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_sigmaI/netI    0
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5389
_diffrn_reflns_theta_max         34.64
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        4.43
_diffrn_standards_interval_time  5400
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.13
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_preparation       'crystalisation from CH2Cl2/hexane'
_refine_diff_density_max         .446
_refine_diff_density_min         -.414
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   0
_refine_ls_extinction_coef       .0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.684
_refine_ls_goodness_of_fit_obs   2.039
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .084
_refine_ls_R_factor_obs          .042
_refine_ls_shift/esd_max         .007
_refine_ls_shift/esd_mean        .001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .05
_refine_ls_wR_factor_obs         .045
_reflns_d_resolution_high        .625
_reflns_d_resolution_low         9.589
_reflns_limit_h_max              30
_reflns_limit_h_min              0
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_observed          3287
_reflns_number_total             5389
_reflns_observed_criterion       refl_observed_if_F____>_.000_sigma(F___)
_cod_data_source_file            b307275d.txt
_cod_data_source_block           tromp_etal
_cod_depositor_comments
;
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_original_sg_symbol_Hall     p_2ac_2ab
_cod_original_sg_symbol_H-M      p_21_21_21
_cod_original_formula_sum        C23H33NO3Si
_cod_database_code               7151540