Experimental and Computational Study of the 1,5-O → N Carbamoyl Snieckus-Fries-Type Rearrangement.
Feberero, Claudia; Sedano, Carlos; Suárez-Pantiga, Samuel; López, Carlos Silva; Sanz, Roberto; The Journal of organic chemistry 85 (2020) 12561–12578; doi:10.1021/acs.joc.0c01732

data_4038766
_publ_section_title
;
 Experimental and Computational Study of the 1,5-O \\rightarrow N
 Carbamoyl Snieckus-Fries-Type Rearrangement.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12561
_journal_page_last               12578
_journal_paper_doi               10.1021/acs.joc.0c01732
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C19 H22 N2 O3 S'
_chemical_formula_sum            'C19 H22 N2 O3 S'
_chemical_formula_weight         358.44
_chemical_name_systematic
'O-4-Methoxy-2-(phenylcarbamothioyl)phenyl N,N-diethylcarbamate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-08 deposited with the CCDC.	2020-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                107.170(4)
_cell_angle_beta                 97.829(4)
_cell_angle_gamma                103.488(4)
_cell_formula_units_Z            2
_cell_length_a                   8.596(3)
_cell_length_b                   10.656(4)
_cell_length_c                   11.508(4)
_cell_measurement_reflns_used    4718
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.311
_cell_measurement_theta_min      2.297
_cell_volume                     955.2(6)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10160
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_min         1.899
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1523 before and 0.0337 after correction. The Ratio of minimum to maximum transmission is 0.7715. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0666P)^2^+0.2156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3232
_reflns_number_total             3872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2002776.cif
_cod_data_source_block           1_a
_cod_depositor_comments
'Adding full bibliography for 4038765--4038772.cif.'
_cod_original_cell_volume        955.3(6)
_cod_database_code               4038766
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C4(H4), C14(H14), C10(H10), C13(H13), C12(H12), C11(H11)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              21020
_shelx_hkl_checksum              83215
_olex2_submission_special_instructions 'No special instructions were received'