Intramolecular Cycloaddition Reactions of cis-1,2-Dihydrocatechol Derivatives Incorporating C3-Tethered Diazoketones, Nitrile Oxides, and Azides: Stereocontrolled Routes to Enantiomerically Pure Spiro[5.5]undecanes and Related Systems
Tristan A. Reekie; Martin G. Banwell; Anthony C. Willis; Journal of Organic Chemistry 78 (2013) 7100–7111; doi:10.1021/jo400952u

data_4028436
_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, A. C. T. 0200, Australia
;
_publ_contact_author_email       'mgb@rsc.anu.edu.au '
_publ_contact_author_fax         ' 61 2 6125 8114 '
_publ_contact_author_name        'Martin G. Banwell'
_publ_contact_author_phone       ' 61 2 6125 8202 '
_publ_section_title
;
 Intramolecular Cycloaddition Reactions of cis-1,2-Dihydrocatechol
 Derivatives Incorporating C3-Tethered Diazoketones, Nitrile Oxides, and
 Azides: Stereocontrolled Routes to Enantiomerically Pure
 Spiro[5.5]undecanes and Related Systems
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7100
_journal_page_last               7111
_journal_paper_doi               10.1021/jo400952u
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_compound_source        local
_chemical_formula_moiety         'C13 H19 N3 O2'
_chemical_formula_sum            'C13 H19 N3 O2'
_chemical_formula_weight         249.31
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-10-19
_audit_creation_method           CRYSTALS_ver_12.85
_audit_update_record
;
2009-10-19 - Report on C13 H19 N3 O2
             by Anthony C. Willis
             for  Tristan Reekie and Martin Banwell

2009-10-19 - passes checkcif tests with minor warnings  

;
_cell_angle_alpha                90
_cell_angle_beta                 105.4814(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2161(1)
_cell_length_b                   11.6949(2)
_cell_length_c                   9.3974(2)
_cell_measurement_reflns_used    11017
_cell_measurement_temperature    200
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2.6
_cell_volume                     658.37(2)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16915
_diffrn_reflns_theta_full        29.995
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_min         3.948
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details
;
The enantiomer has been assigned by reference to an unchanging chiral
centre in the synthetic procedure.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.8683
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         1994
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.008518
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0677
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0677
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1607
_reflns_number_total             1994
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.72
_oxford_diffrn_Wilson_scale      0.38
_oxford_refine_ls_r_factor_ref   0.0380
_oxford_refine_ls_scale          1.764(11)
_oxford_reflns_number_all        1994
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '10191128 ban0922'
_cod_data_source_file            jo400952u_si_005.cif
_cod_data_source_block           ban0922
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4028436