Nonbonded, Attractive Cation-π Interactions in Azide-Mediated Asymmetric Ring Expansion Reactions
Christopher E. Katz; Timothy Ribelin; Donna Withrow; Yashar Basseri; Anna K. Manukyan; Amy Bermudez; Christian G Nuera; Victor W. Day; Douglas R. Powell; Jennifer L. Poutsma; Jeffrey Aubé; Journal of Organic Chemistry 73 (2008) 3318–3327; doi:10.1021/jo800222r

data_4023393
_publ_contact_author
; 
   Prof. Jeffrey Aub\'e 
   Department of Medicinal Chemistry -- University of Kansas 
   Malott Hall 
   1251 Wescoe Hall Dr, Rm 4070 
   Lawrence, KS  66045-7582  USA 
;
_publ_contact_author_email       jaube@ku.edu
_publ_contact_author_fax         1(785)8645326
_publ_contact_author_phone       1(785)8644496
_publ_section_title
;
 Nonbonded, Attractive Cation-\p Interactions in
 Azide-Mediated Asymmetric Ring Expansion Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3318
_journal_page_last               3327
_journal_paper_doi               10.1021/jo800222r
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C18 H33 N O2'
_chemical_formula_weight         295.45
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.4540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.2113(8)
_cell_length_b                   11.5987(6)
_cell_length_c                   9.9385(6)
_cell_measurement_reflns_used    5632
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.22
_cell_volume                     1729.65(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_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       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20356
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         2.71
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Thin plate'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         5283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+0.2280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                4393
_reflns_number_total             5283
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800222r-File003_5.cif
_cod_data_source_block           k76d_(Compound_32a)
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023393