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_1549237
_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         'C22 H30 Cl N O4 S'
_chemical_formula_sum            'C22 H30 Cl N O4 S'
_chemical_formula_weight         439.98
_chemical_name_systematic
;3-(2-(5-chloro-2-ethoxy-3-(isopropylthio)phenyl)-2-cyclohexylacetyl)
oxazolidin-2-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 103.196(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0663(6)
_cell_length_b                   10.1526(5)
_cell_length_c                   18.2867(10)
_cell_measurement_reflns_used    9592
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.025
_cell_measurement_theta_min      2.285
_cell_volume                     2181.05(19)
_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      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1162
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            63457
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.083
_diffrn_reflns_theta_min         2.285
_diffrn_source                   'sealed  X-ray tube'
_diffrn_source_type              'Incoatec IuSMo'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.3209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.1532 before and 0.0625 after correction. 
The Ratio of minimum to maximum transmission is 0.4302. 
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    1.340
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.995
_exptl_crystal_size_mid          0.558
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         6407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0396P)^2^+0.7640P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5250
_reflns_number_total             6407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04736c2.cif
_cod_data_source_block           mo_dakl365_p21n
_cod_depositor_comments
'Adding full bibliography for 1549237--1549239.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1549237
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.755