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_1507565
_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[1,2] major product'
_chemical_name_systematic
;
styryl[1,2] major product
;
_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   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                 95.847(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8355(15)
_cell_length_b                   10.4469(11)
_cell_length_c                   10.3765(11)
_cell_measurement_reflns_used    11430
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.4
_cell_measurement_theta_min      2.3
_cell_volume                     1492.0(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      366,366,366,420
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen grip'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      -0.0191686
_diffrn_orient_matrix_UB_12      -0.0060894
_diffrn_orient_matrix_UB_13      -0.0721457
_diffrn_orient_matrix_UB_21      -0.0646090
_diffrn_orient_matrix_UB_22      0.0707876
_diffrn_orient_matrix_UB_23      0.0012963
_diffrn_orient_matrix_UB_31      0.0695736
_diffrn_orient_matrix_UB_32      0.0641228
_diffrn_orient_matrix_UB_33      -0.0083695
_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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21226
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.45
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_id                'Doyle/Jaber styryl-[1,2] Major Product 150K'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.001
_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^+0.967P], P=(max(Fo^2^,0)+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0754
_reflns_number_gt                3892
_reflns_number_total             4364
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300213u_si_002.cif
_cod_data_source_block           1975
_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/c
_cod_database_code               1507565
_diffrn_measurement_frame_width-ccd -0.5
_diffrn_measurement_total_frames-ccd 1518
_diffrn_measurement_frame_time-ccd 10
_diffrn_measurement_total_time-ccd 6.7
_diffrn_detector_distance-ccd    5.000
_diffrn_measurement_frame_size-ccd 512