Nucleophilicity Parameters of Pyridinium Ylides and Their Use in Mechanistic Analyses
Dominik S. Allgäuer; Peter Mayer; Herbert Mayr; Journal of the American Chemical Society 135 (2013) 15216–15224; doi:10.1021/ja407885h

data_4120918
_publ_contact_author_address
;
Department Chemie
Ludwig-Maximilians Universit\"at
Butenandtstra\&se 5-13 (Haus F)
D-81377 M\"unchen
Bundesrepublik Deutschland
;
_publ_contact_author_email       Herbert.Mayr@cup.uni-muenchen.de
_publ_contact_author_fax         '+49 89 2180 77717'
_publ_contact_author_name        'H. Mayr'
_publ_section_title
;
 Nucleophilicity Parameters of Pyridinium Ylides and Their Use in
 Mechanistic Analyses
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15216
_journal_page_last               15224
_journal_paper_doi               10.1021/ja407885h
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C19 H14 N2 O2'
_chemical_formula_sum            'C19 H14 N2 O2'
_chemical_formula_weight         302.327
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_author_name               'Peter Mayer'
_audit_block_code                C19H14N2O2_qq071_mayr
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             31-Oct-12
_cell_angle_alpha                90.00
_cell_angle_beta                 107.919(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.3827(4)
_cell_length_b                   12.0666(3)
_cell_length_c                   17.7872(5)
_cell_measurement_reflns_used    122
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      20.6818
_cell_measurement_theta_min      2.1946
_cell_volume                     3141.45(15)
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
<i>Acta Cryst.</i> A<b>64</b>, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8Quest'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            63848
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.28
_diffrn_source_current           1
_diffrn_source_power             50
_diffrn_source_type              'Bruker I\mS'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.9053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.27847(6)
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         7220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0542P)^2^+1.1648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1343
_reflns_number_gt                4822
_reflns_number_total             7220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja407885h_si_002_1.cif
_cod_data_source_block           qq071
_cod_original_cell_volume        3141.45(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4120918