An Unexpected Ireland-Claisen Rearrangement Cascade During the Synthesis of the Tricyclic Core of Curcusone C: Mechanistic Elucidation by Trial-and-Error and Automatic Artificial Force-Induced Reaction (AFIR) Computations.
Lee, Chung Whan; Taylor, Buck L. H.; Petrova, Galina P.; Patel, Ashay; Morokuma, Keiji; Houk, K. N.; Stoltz, Brian M.; Journal of the American Chemical Society 141 (2019) 6995–7004; doi:10.1021/jacs.9b01146

data_4128142
_publ_section_title
;
 An Unexpected Ireland-Claisen Rearrangement Cascade During the Synthesis
 of the Tricyclic Core of Curcusone C: Mechanistic Elucidation by
 Trial-and-Error and Automatic Artificial Force-Induced Reaction (AFIR)
 Computations.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6995
_journal_page_last               7004
_journal_paper_doi               10.1021/jacs.9b01146
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C15 H18 O3'
_chemical_formula_sum            'C15 H18 O3'
_chemical_formula_weight         246.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     dual
_audit_creation_date             2012-12-02
_audit_creation_method
;
  Olex2 1.2
  (compiled Nov  5 2012 18:25:38, GUI svn.r4372),
 SHELXL-2012,
 and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 90.669(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0015(4)
_cell_length_b                   10.2072(6)
_cell_length_c                   14.8838(8)
_cell_measurement_reflns_used    9118
_cell_measurement_temperature    100
_cell_measurement_theta_max      41.03
_cell_measurement_theta_min      2.42
_cell_volume                     1215.52(11)
_computing_cell_refinement       'SAINT V8.27B (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 2012.4-3 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.27B (Bruker-AXS, 2007)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
 and SHELXTL (Bruker-AXS, 2007)
;
_computing_structure_refinement  'SHELXL-2012/7 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            83376
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         41.581
_diffrn_reflns_theta_min         2.420
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0518 before and 0.0492 after correction.
The Ratio of minimum to maximum transmission is 0.9532.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       slab
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.756
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         8050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.756
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0400P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1117
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6562
_reflns_number_total             8050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b01146_si_002.cif
_cod_data_source_block           cwl101
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_source_target' value 'MO' changed to 'Mo' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4128142
_olex2_refinement_description
;
;
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.960
_shelx_hkl_checksum              12993
_shelx_res_checksum              40344
_shelxl_version_number           2012-6