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_4038765
_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         'C25 H27 Cl N2 O4 S'
_chemical_formula_sum            'C25 H27 Cl N2 O4 S'
_chemical_formula_weight         486.99
_chemical_name_systematic
'O-4-Chloro-2-(((4-methylphenyl)sulfonamido)(phenyl)methyl)phenyl N,N-diethylcarbamate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-30 deposited with the CCDC.	2020-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9060(6)
_cell_length_b                   13.6614(7)
_cell_length_c                   16.6806(9)
_cell_measurement_reflns_used    4356
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.39
_cell_volume                     2485.3(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29708
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.176
_diffrn_reflns_theta_max         25.176
_diffrn_reflns_theta_min         2.390
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0870 before and 0.0616 after correction. The Ratio of minimum to maximum transmission is 0.7277. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1436 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0268P)^2^+0.6366P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3827
_reflns_number_total             4403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2000155.cif
_cod_data_source_block           mo_scan_0m
_cod_depositor_comments
'Adding full bibliography for 4038765--4038772.cif.'
_cod_database_code               4038765
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.899
_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 Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C27(H27), C22(H22), C26(H26), C33(H33), C7(H7), C29(H29),
 C23(H23), C31(H31), C32(H32), C30(H30)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C25(H25A,H25B,H25C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              47630
_shelx_hkl_checksum              22693
_olex2_submission_special_instructions 'No special instructions were received'