Unusual mechanisms in Claisen rearrangements: an ionic fragmentation leading to a <i>meta</i>-selective rearrangement.
Maryasin, Boris; Kaldre, Dainis; Galaverna, Renan; Klose, Immo; Ruider, Stefan; Drescher, Martina; Kählig, Hanspeter; González, Leticia; Eberlin, Marcos N.; Jurberg, Igor D.; Maulide, Nuno; Chemical science 9 (2018) 4124–4131; doi:10.1039/c7sc04736c

data_1549239
_publ_section_title
;
 Unusual mechanisms in Claisen rearrangements: an ionic fragmentation
 leading to a <i>meta</i>-selective rearrangement.
;
_journal_issue                   17
_journal_name_full               'Chemical science'
_journal_page_first              4124
_journal_page_last               4131
_journal_paper_doi               10.1039/c7sc04736c
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C20 H25 N O5 S'
_chemical_formula_sum            'C20 H25 N O5 S'
_chemical_formula_weight         391.48
_chemical_name_systematic
'3-(1-cyclohexyl-2-oxo-2-(2-oxooxazolidin-3-yl)ethyl)-2-(methylthio)phenyl acetate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-03-29 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7592(13)
_cell_length_b                   10.1198(10)
_cell_length_c                   32.161(3)
_cell_measurement_reflns_used    9017
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.320
_cell_measurement_theta_min      2.377
_cell_volume                     3827.2(7)
_computing_cell_refinement       'APEX2 v2013.6-2'
_computing_data_collection       'APEX2 v2013.6-2'
_computing_data_reduction        'APEX2 v2013.6-2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            100589
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.380
_diffrn_reflns_theta_min         2.378
_diffrn_source                   'sealed  X-ray tube'
_diffrn_source_type              'Incoatec IuSMo'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.1046 before and 0.0541 after correction. 
The Ratio of minimum to maximum transmission is 0.8549. 
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       plate
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 3224 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.11(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7014
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0716P)^2^+3.0440P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                6782
_reflns_number_total             7014
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04736c2.cif
_cod_data_source_block           mo_dakl346_pca21
_cod_depositor_comments
'Adding full bibliography for 1549237--1549239.cif.'
_cod_database_code               1549239
_shelxl_version_number           2013-2