Competitive [2,3]- and [1,2]-oxonium ylide rearrangements. Concerted or stepwise?
Jaber, Deana M.; Burgin, Ryan N.; Helper, Matthew; Zavalij, Peter Y.; Doyle, Michael P.; Organic letters 14 (2012) 1676–1679; doi:10.1021/ol300213u

data_1507566
_publ_section_title
;
 Competitive [2,3]- and [1,2]-oxonium ylide rearrangements. Concerted or
 stepwise?
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1676
_journal_page_last               1679
_journal_paper_doi               10.1021/ol300213u
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C18 H18 O5'
_chemical_formula_sum            'C18 H18 O5'
_chemical_formula_weight         314.32
_chemical_name_common            styryl-[2,3]
_chemical_name_systematic
;
styryl-[2,3]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           'SHELXL-97 & ZCIF'
_cell_angle_alpha                90.00
_cell_angle_beta                 113.8418(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4080(5)
_cell_length_b                   32.530(3)
_cell_length_c                   7.8956(6)
_cell_measurement_reflns_used    15412
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.1
_cell_measurement_theta_min      2.5
_cell_volume                     1505.4(2)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2005)'
_computing_data_reduction        Apex2
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 11.198
_diffrn_detector_type            'Bruker Smart Apex II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      610,610,610,1200
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.1203753
_diffrn_orient_matrix_UB_12      -0.0018274
_diffrn_orient_matrix_UB_13      0.1289287
_diffrn_orient_matrix_UB_21      0.0240259
_diffrn_orient_matrix_UB_22      0.0303839
_diffrn_orient_matrix_UB_23      0.0006120
_diffrn_orient_matrix_UB_31      -0.1184992
_diffrn_orient_matrix_UB_32      0.0043010
_diffrn_orient_matrix_UB_33      0.0505063
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24755
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.50
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_id
'Doyle/Jaber styryl-[2,3]-minor product - prisms 150K'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.01P)^2^+1.001P], P=(max(Fo^2^,0)+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                4007
_reflns_number_total             4363
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300213u_si_003.cif
_cod_data_source_block           1993
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1507566
_diffrn_measurement_frame_width-ccd -0.30
_diffrn_measurement_total_frames-ccd 3030
_diffrn_measurement_frame_time-ccd 15
_diffrn_measurement_total_time-ccd 17.7
_diffrn_detector_distance-ccd    5.000
_diffrn_measurement_frame_size-ccd 512