Cyclization/hydrolysis of 1,5-enenitriles initiated by sulfonyl radicals in the aqueous phase in the presence of the I2/TBHP system
Hu, Sen-Jie; Jiang, Li-Lin; Qiu, Hui; Luo, Chun-Mei; Guan, Yu-Tao; Li, Long; Dong, Youren; Lei, Ke-Wei; Wei, Wen-Ting; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01124G

data_7158794
_publ_section_title
;
 Cyclization/hydrolysis of 1,5-enenitriles initiated by sulfonyl radicals
 in the aqueous phase in the presence of the I2/TBHP system
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01124G
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H19 N O4 S'
_chemical_formula_sum            'C19 H19 N O4 S'
_chemical_formula_weight         357.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-21 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.051(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0585(9)
_cell_length_b                   6.5274(3)
_cell_length_c                   19.2202(11)
_cell_measurement_reflns_used    2823
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.390
_cell_measurement_theta_min      3.015
_cell_volume                     1694.99(17)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7146
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.435
_diffrn_reflns_theta_min         3.015
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1081 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.8958. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 932 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2980
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0390P)^2^+1.1273P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.742
_reflns_Friedel_fraction_max     0.712
_reflns_number_gt                2604
_reflns_number_total             2980
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01124g2.cif
_cod_data_source_block           nb_0m
_cod_database_code               7158794
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C18(H18), C14(H14), C2(H2), C4(H4), C17(H17), C5(H5), C3(H3), C15(H15)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'