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_1549238
_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         'C23 H19 N O3 S'
_chemical_formula_sum            'C23 H19 N O3 S'
_chemical_formula_weight         389.45
_chemical_name_systematic
3-(2-phenyl-2-(4-(phenylthio)phenyl)acetyl)oxazolidin-2-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_audit_update_record
;
2017-08-11 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            16
_cell_length_a                   22.362(13)
_cell_length_b                   58.28(3)
_cell_length_c                   5.779(4)
_cell_measurement_reflns_used    1696
_cell_measurement_temperature    130.0
_cell_measurement_theta_max      18.532
_cell_measurement_theta_min      2.296
_cell_volume                     7532(8)
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_collection       'APEX 2 (Bruker, 2011)'
_computing_data_reduction        'SAINT V8.32B (?, 2016)'
_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      130.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.1260
_diffrn_reflns_av_unetI/netI     0.1131
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       69
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            19341
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.296
_diffrn_source                   'sealed xray tube'
_diffrn_source_type              'Incoatec IuS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.1330 before and 0.0640 after correction. 
The Ratio of minimum to maximum transmission is 0.7939. 
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    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             3264
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.18(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3404
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0627
_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^)+(0.0634P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1412
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2253
_reflns_number_total             3404
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04736c2.cif
_cod_data_source_block           madr050_fdd2
_cod_depositor_comments
'Adding full bibliography for 1549237--1549239.cif.'
_cod_database_code               1549238
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.971