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_4120919
_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         'C30 H32 N3 O, B F4, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C30.5 H33 B Cl F4 N3 O'
_chemical_formula_weight         579.865
_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               'Mayer, P.'
_audit_block_code                C30H32N3O_BF4_CH2Cl2_nn351_mayr
_audit_creation_date             05-Aug-09
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             06-Aug-09
_cell_angle_alpha                90.00
_cell_angle_beta                 98.2496(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.9080(2)
_cell_length_b                   18.0229(3)
_cell_length_c                   30.2720(5)
_cell_measurement_reflns_used    20049
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      3.134
_cell_volume                     5889.71(18)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement
'SHELXL-97 (G. M. Sheldrick. University of G\"ottingen, 97-2 version)'
_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 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images, phi/omega-scan'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0762785
_diffrn_orient_matrix_UB_12      -0.0288912
_diffrn_orient_matrix_UB_13      -0.0035031
_diffrn_orient_matrix_UB_21      0.0417392
_diffrn_orient_matrix_UB_22      0.0466930
_diffrn_orient_matrix_UB_23      -0.0076849
_diffrn_orient_matrix_UB_31      0.0319462
_diffrn_orient_matrix_UB_32      0.0079777
_diffrn_orient_matrix_UB_33      0.0322931
_diffrn_radiation_collimation    0.20
_diffrn_radiation_monochromator  'MONTEL, graded multilayered x-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            37065
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         3.18
_diffrn_source_current           55.00
_diffrn_source_power             3.025
_diffrn_source_type              'FR 591 generator'
_diffrn_source_voltage           55.00
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.30791(4)
_exptl_crystal_description       platelet
_exptl_crystal_F_000             2424
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.228
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0013(6)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     740
_refine_ls_number_reflns         10732
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.0897
_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^)+(0.1520P)^2^+4.0092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2581
_refine_ls_wR_factor_ref         0.3056
_reflns_number_gt                5645
_reflns_number_total             10732
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja407885h_si_002_2.cif
_cod_data_source_block           nn351
_cod_original_cell_volume        5889.71(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C30.50 H33 B Cl F4 N3 O'
_cod_database_code               4120919