π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gem-dibromocyclopropanes possessing tethered nucleophiles: the influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates
Banwell, Martin; Edwards, Alison; Harvey, Joanne; Hockless, David; Willis, Anthony; Journal of the Chemical Society, Perkin Transactions 1  (2000) 2175–; doi:10.1039/b002525i

data_7213338
_publ_section_title
;
 \p-Allyl cation cyclisations initiated by silver(I)-promoted
 electrocyclic ring opening of ring-fused gem-dibromocyclopropanes
 possessing tethered nucleophiles: the influence of chiral auxiliaries on
 the diastereoselectivity of cyclisations involving meso-substrates
;
_journal_issue                   14
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2175
_journal_paper_doi               10.1039/b002525i
_journal_year                    2000
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C19 H30 Br N O2 '
_chemical_formula_sum            'C19 H30 Br N O2'
_chemical_formula_weight         384.358
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 97.278(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4008(5)
_cell_length_b                   9.9077(6)
_cell_length_c                   11.8739(8)
_cell_measurement_reflns_used    9117
_cell_measurement_temperature    200
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.546
_cell_volume                     980.33(11)
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_publication_material  'maxus(Mackay et al., 1999)'
_computing_structure_refinement  'maxus(Mackay et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_measurement_device       KappaCCD
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9089
_diffrn_reflns_theta_max         25.03
_exptl_absorpt_coefficient_mu    2.11
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.44
_refine_diff_density_rms         0.06
_refine_ls_abs_structure_details
;
1425 Friedel equivalents measured clearly showing via the Rogers 
parameter that the absolute structure is as reported.  
This is in accord with the known absolute structure of the menthyl 
group used in the synthesis.
;
_refine_ls_abs_structure_Rogers  1.03
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.179
_refine_ls_goodness_of_fit_gt    1.129
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2453
_refine_ls_R_factor_all          0.062
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
; 
w = 1 / ( s^2^(Fo^2^) + 0.03000 * Fo^2^)
;
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.064
_refine_ls_wR_factor_gt          0.045
_refine_ls_wR_factor_ref         0.063
_reflns_d_resolution_high        0.65
_reflns_d_resolution_low         1.79
_reflns_Friedel_coverage         0.775
_reflns_limit_h_max              10
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                2453
_reflns_number_total             3263
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_cod_data_source_file            b002525isup1.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        980.3(5)
_cod_original_sg_symbol_H-M      'P 21          '
_cod_original_formula_sum        'C19 H30 Br N O2 '
_cod_database_code               7213338