#------------------------------------------------------------------------------
#$Date: 2022-07-26 03:46:28 +0300 (Tue, 26 Jul 2022) $
#$Revision: 276937 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158794.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158794
loop_
_publ_author_name
'Hu, Sen-Jie'
'Jiang, Li-Lin'
'Qiu, Hui'
'Luo, Chun-Mei'
'Guan, Yu-Tao'
'Li, Long'
'Dong, Youren'
'Lei, Ke-Wei'
'Wei, Wen-Ting'
_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 & 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       'φ and ω 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 λ/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/[σ²(Fo²)+(0.0390P)²+1.1273P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            d2ob01124g2.cif
_cod_data_source_block           nb_0m
_cod_database_code               7158794
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.65326(7) 0.39845(15) 0.61861(5) 0.0269(3) Uani 1 1 d . . . . .
O4 O 0.7446(2) 0.3220(5) 0.66529(15) 0.0335(7) Uani 1 1 d . . . . .
O1 O 0.3835(2) 0.2618(4) 0.53369(14) 0.0292(7) Uani 1 1 d . . . . .
O2 O 0.5198(2) 0.7923(5) 0.69729(15) 0.0390(8) Uani 1 1 d . . . . .
O3 O 0.6457(3) 0.6138(4) 0.59987(15) 0.0336(8) Uani 1 1 d . . . . .
C1 C 0.3435(3) 0.6484(6) 0.4489(2) 0.0232(9) Uani 1 1 d . . . . .
C10 C 0.4081(3) 0.4306(6) 0.5587(2) 0.0226(9) Uani 1 1 d . . . . .
C13 C 0.6241(3) 0.2553(6) 0.5376(2) 0.0257(9) Uani 1 1 d . . . . .
N1 N 0.3909(2) 0.6148(5) 0.52407(16) 0.0228(8) Uani 1 1 d . . . . .
C7 C 0.4254(3) 0.7920(6) 0.5721(2) 0.0250(9) Uani 1 1 d . . . . .
H7A H 0.368964 0.877162 0.576228 0.030 Uiso 1 1 calc R . . . .
H7B H 0.471365 0.878062 0.553927 0.030 Uiso 1 1 calc R . . . .
C8 C 0.4775(3) 0.6967(6) 0.6437(2) 0.0271(9) Uani 1 1 d . . . . .
C6 C 0.3249(3) 0.4871(6) 0.3995(2) 0.0277(10) Uani 1 1 d . . . . .
H6 H 0.341670 0.350731 0.415460 0.033 Uiso 1 1 calc R . . . .
C12 C 0.5603(3) 0.3463(6) 0.6638(2) 0.0249(9) Uani 1 1 d . . . . .
H12A H 0.544313 0.198489 0.658258 0.030 Uiso 1 1 calc R . . . .
H12B H 0.589321 0.372796 0.716064 0.030 Uiso 1 1 calc R . . . .
C18 C 0.5745(3) 0.3454(7) 0.4723(2) 0.0297(10) Uani 1 1 d . . . . .
H18 H 0.556788 0.486136 0.470281 0.036 Uiso 1 1 calc R . . . .
C11 C 0.3969(3) 0.3979(7) 0.6862(2) 0.0326(11) Uani 1 1 d . . . . .
H11A H 0.336455 0.480787 0.674103 0.049 Uiso 1 1 calc GR . . . .
H11B H 0.432174 0.416767 0.737426 0.049 Uiso 1 1 calc GR . . . .
H11C H 0.379571 0.253069 0.677040 0.049 Uiso 1 1 calc GR . . . .
C14 C 0.6517(3) 0.0506(6) 0.5412(2) 0.0290(10) Uani 1 1 d . . . . .
H14 H 0.686099 -0.009840 0.586041 0.035 Uiso 1 1 calc R . . . .
C2 C 0.3176(3) 0.8459(7) 0.4252(2) 0.0286(10) Uani 1 1 d . . . . .
H2 H 0.329143 0.956042 0.458778 0.034 Uiso 1 1 calc R . . . .
C4 C 0.2561(3) 0.7250(7) 0.3027(2) 0.0323(11) Uani 1 1 d . . . . .
H4 H 0.226039 0.751171 0.252864 0.039 Uiso 1 1 calc R . . . .
C9 C 0.4638(3) 0.4655(6) 0.6391(2) 0.0242(9) Uani 1 1 d . . . . .
C17 C 0.5513(4) 0.2265(7) 0.4100(2) 0.0343(11) Uani 1 1 d . . . . .
H17 H 0.517416 0.287138 0.365029 0.041 Uiso 1 1 calc R . . . .
C5 C 0.2815(3) 0.5275(7) 0.3266(2) 0.0320(11) Uani 1 1 d . . . . .
H5 H 0.269198 0.417964 0.292705 0.038 Uiso 1 1 calc R . . . .
C3 C 0.2747(4) 0.8831(7) 0.3518(2) 0.0362(11) Uani 1 1 d . . . . .
H3 H 0.258028 1.019304 0.335515 0.043 Uiso 1 1 calc R . . . .
C15 C 0.6281(4) -0.0643(7) 0.4779(2) 0.0329(10) Uani 1 1 d . . . . .
H15 H 0.647641 -0.203950 0.479544 0.039 Uiso 1 1 calc R . . . .
C16 C 0.5765(3) 0.0215(7) 0.4122(2) 0.0310(10) Uani 1 1 d . . . . .
C19 C 0.5465(4) -0.1116(8) 0.3450(2) 0.0403(12) Uani 1 1 d . . . . .
H19A H 0.479292 -0.163654 0.338879 0.060 Uiso 1 1 calc GR . . . .
H19B H 0.592541 -0.227015 0.350271 0.060 Uiso 1 1 calc GR . . . .
H19C H 0.548319 -0.030260 0.302578 0.060 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O3 118.93(19) . . ?
O4 S1 C13 108.43(19) . . ?
O4 S1 C12 106.12(18) . . ?
O3 S1 C13 108.16(18) . . ?
O3 S1 C12 106.98(19) . . ?
C13 S1 C12 107.74(19) . . ?
C6 C1 N1 121.3(3) . . ?
C2 C1 N1 118.9(3) . . ?
C2 C1 C6 119.8(3) . . ?
O1 C10 N1 128.0(4) . . ?
O1 C10 C9 122.7(3) . . ?
N1 C10 C9 109.3(3) . . ?
C18 C13 S1 120.7(3) . . ?
C18 C13 C14 121.1(4) . . ?
C14 C13 S1 118.3(3) . . ?
C1 N1 C7 119.5(3) . . ?
C10 N1 C1 126.8(3) . . ?
C10 N1 C7 113.7(3) . . ?
N1 C7 H7A 111.0 . . ?
N1 C7 H7B 111.0 . . ?
N1 C7 C8 104.0(3) . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 H7A 111.0 . . ?
C8 C7 H7B 111.0 . . ?
O2 C8 C7 124.5(4) . . ?
O2 C8 C9 125.9(4) . . ?
C7 C8 C9 109.6(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
S1 C12 H12A 108.0 . . ?
S1 C12 H12B 108.0 . . ?
H12A C12 H12B 107.2 . . ?
C9 C12 S1 117.4(3) . . ?
C9 C12 H12A 108.0 . . ?
C9 C12 H12B 108.0 . . ?
C13 C18 H18 120.5 . . ?
C13 C18 C17 118.9(4) . . ?
C17 C18 H18 120.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.8(4) . . ?
C15 C14 H14 120.6 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.9(4) . . ?
C3 C2 H2 120.1 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(4) . . ?
C8 C9 C10 103.0(3) . . ?
C8 C9 C12 113.6(4) . . ?
C8 C9 C11 109.8(3) . . ?
C12 C9 C10 113.4(3) . . ?
C12 C9 C11 107.9(3) . . ?
C11 C9 C10 108.9(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 C18 121.2(4) . . ?
C16 C17 H17 119.4 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 118.9(4) . . ?
C17 C16 C19 121.4(4) . . ?
C15 C16 C19 119.7(4) . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.438(3) . ?
S1 O3 1.448(3) . ?
S1 C13 1.764(4) . ?
S1 C12 1.790(4) . ?
O1 C10 1.213(5) . ?
O2 C8 1.210(5) . ?
C1 N1 1.430(5) . ?
C1 C6 1.394(6) . ?
C1 C2 1.382(6) . ?
C10 N1 1.363(5) . ?
C10 C9 1.545(5) . ?
C13 C18 1.387(6) . ?
C13 C14 1.388(6) . ?
N1 C7 1.476(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.503(5) . ?
C8 C9 1.521(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C9 1.521(6) . ?
C18 H18 0.9500 . ?
C18 C17 1.389(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C9 1.538(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(6) . ?
C4 C3 1.373(6) . ?
C17 H17 0.9500 . ?
C17 C16 1.382(7) . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.389(6) . ?
C16 C19 1.516(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
