#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:41:40 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290263 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/97/7159771.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_7159771
loop_
_publ_author_name
'Qin, Hong'
'Chen, Feng'
'Du, Jinze'
'Yang, Xiaobing'
'Huang, Yiping'
'Zhu, Kai'
'Yue, Changhai'
'Fang, Zheng'
'Guo, Kai'
_publ_section_title
;
 Thiocyanate promoted difunctionalization and cyclization of unsaturated
 C--C bonds to construct 1-sulfur-2-nitrogen-functionalized alkenes and
 2-thiocyanate indolines
;
_journal_issue                   6
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1213
_journal_page_last               1218
_journal_paper_doi               10.1039/D3OB01864D
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C26 H23 N3 O2 S3'
_chemical_formula_sum            'C26 H23 N3 O2 S3'
_chemical_formula_weight         505.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-19 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.0630(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.0220(3)
_cell_length_b                   11.6268(2)
_cell_length_c                   22.3898(3)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.916
_cell_measurement_theta_min      3.871
_cell_volume                     4982.74(13)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      173.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20255
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.954
_diffrn_reflns_theta_min         3.870
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.920
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1217 before and 0.0452 after correction. The Ratio of minimum to maximum transmission is 0.8183. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0326P)²+5.3909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4184
_reflns_number_total             4675
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01864d2.cif
_cod_data_source_block           2104011479_0m
_cod_depositor_comments          'Adding full bibliography for 7159771.cif.'
_cod_database_code               7159771
_shelx_shelxl_version_number     2016/6
_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   0.910
_shelx_estimated_absorpt_t_min   0.877
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15),
 C16(H16), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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'
'-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 0.84678(2) 0.10417(3) 0.23243(2) 0.03179(11) Uani 1 1 d . . . . .
S2 S 0.91776(4) 0.48790(6) 0.15996(3) 0.0725(2) Uani 1 1 d . . . . .
S3 S 0.92463(2) 0.42276(4) 0.38695(2) 0.03779(12) Uani 1 1 d . . . . .
O1 O 0.79853(7) 0.01199(10) 0.22678(6) 0.0435(3) Uani 1 1 d . . . . .
O2 O 0.91471(6) 0.10058(11) 0.27648(6) 0.0444(3) Uani 1 1 d . . . . .
N1 N 0.80867(6) 0.22020(11) 0.25156(6) 0.0279(3) Uani 1 1 d . . . . .
N2 N 0.88940(7) 0.37722(13) 0.25731(6) 0.0375(3) Uani 1 1 d . . . . .
N3 N 0.87317(10) 0.50826(16) 0.48318(9) 0.0580(5) Uani 1 1 d . . . . .
C1 C 0.85209(8) 0.30802(13) 0.28664(7) 0.0274(3) Uani 1 1 d . . . . .
C2 C 0.85963(7) 0.32223(13) 0.34761(7) 0.0257(3) Uani 1 1 d . . . . .
C3 C 0.82076(7) 0.25700(13) 0.38328(7) 0.0238(3) Uani 1 1 d . . . . .
C4 C 0.85520(8) 0.17781(14) 0.42820(7) 0.0294(3) Uani 1 1 d . . . . .
H4 H 0.904096 0.166512 0.436716 0.035 Uiso 1 1 calc R . . . .
C5 C 0.81826(9) 0.11541(15) 0.46053(8) 0.0366(4) Uani 1 1 d . . . . .
H5 H 0.841837 0.060806 0.491008 0.044 Uiso 1 1 calc R . . . .
C6 C 0.74739(9) 0.13201(16) 0.44880(8) 0.0386(4) Uani 1 1 d . . . . .
H6 H 0.722078 0.088512 0.470823 0.046 Uiso 1 1 calc R . . . .
C7 C 0.71351(9) 0.21186(17) 0.40503(9) 0.0408(4) Uani 1 1 d . . . . .
H7 H 0.664749 0.223687 0.397200 0.049 Uiso 1 1 calc R . . . .
C8 C 0.74968(8) 0.27515(15) 0.37229(8) 0.0335(4) Uani 1 1 d . . . . .
H8 H 0.725976 0.330701 0.342460 0.040 Uiso 1 1 calc R . . . .
C9 C 0.89131(9) 0.47061(15) 0.44335(8) 0.0345(4) Uani 1 1 d . . . . .
C10 C 0.90053(9) 0.42330(15) 0.21458(8) 0.0346(4) Uani 1 1 d . . . . .
C11 C 0.73742(8) 0.24653(13) 0.21596(7) 0.0264(3) Uani 1 1 d . . . . .
C12 C 0.68347(9) 0.18348(15) 0.22697(8) 0.0357(4) Uani 1 1 d . . . . .
H12 H 0.693456 0.123374 0.257031 0.043 Uiso 1 1 calc R . . . .
C13 C 0.61522(8) 0.20835(15) 0.19409(8) 0.0357(4) Uani 1 1 d . . . . .
H13 H 0.578592 0.163903 0.201431 0.043 Uiso 1 1 calc R . . . .
C14 C 0.59860(8) 0.29743(13) 0.15020(7) 0.0273(3) Uani 1 1 d . . . . .
C15 C 0.65362(8) 0.35872(14) 0.14014(7) 0.0286(3) Uani 1 1 d . . . . .
H15 H 0.643870 0.419673 0.110586 0.034 Uiso 1 1 calc R . . . .
C16 C 0.72269(8) 0.33348(13) 0.17210(7) 0.0278(3) Uani 1 1 d . . . . .
H16 H 0.759559 0.375837 0.163803 0.033 Uiso 1 1 calc R . . . .
C17 C 0.52211(8) 0.32296(14) 0.11547(7) 0.0290(3) Uani 1 1 d . . . . .
C18 C 0.51485(9) 0.42951(16) 0.07407(9) 0.0402(4) Uani 1 1 d . . . . .
H18A H 0.534828 0.496199 0.099918 0.060 Uiso 1 1 calc GR . . . .
H18B H 0.465309 0.443679 0.052815 0.060 Uiso 1 1 calc GR . . . .
H18C H 0.539753 0.416964 0.042917 0.060 Uiso 1 1 calc GR . . . .
C19 C 0.49065(9) 0.21958(15) 0.07422(8) 0.0359(4) Uani 1 1 d . . . . .
H19A H 0.516221 0.206826 0.043596 0.054 Uiso 1 1 calc GR . . . .
H19B H 0.441408 0.234947 0.052340 0.054 Uiso 1 1 calc GR . . . .
H19C H 0.494211 0.150938 0.100370 0.054 Uiso 1 1 calc GR . . . .
C20 C 0.48102(9) 0.34477(17) 0.16249(8) 0.0399(4) Uani 1 1 d . . . . .
H20A H 0.481374 0.275046 0.187176 0.060 Uiso 1 1 calc GR . . . .
H20B H 0.432697 0.365157 0.139943 0.060 Uiso 1 1 calc GR . . . .
H20C H 0.502754 0.408029 0.190362 0.060 Uiso 1 1 calc GR . . . .
C21 C 0.85450(8) 0.13172(13) 0.15748(7) 0.0304(3) Uani 1 1 d . . . . .
C22 C 0.79621(9) 0.11574(15) 0.10612(8) 0.0364(4) Uani 1 1 d . . . . .
H22 H 0.753998 0.086477 0.111398 0.044 Uiso 1 1 calc R . . . .
C23 C 0.80046(11) 0.14299(17) 0.04730(8) 0.0448(4) Uani 1 1 d . . . . .
H23 H 0.760954 0.132501 0.011833 0.054 Uiso 1 1 calc R . . . .
C24 C 0.86179(12) 0.18530(18) 0.03992(10) 0.0523(5) Uani 1 1 d . . . . .
H24 H 0.864114 0.205639 -0.000519 0.063 Uiso 1 1 calc R . . . .
C25 C 0.91961(12) 0.19821(19) 0.09079(11) 0.0547(5) Uani 1 1 d . . . . .
H25 H 0.961982 0.225791 0.085082 0.066 Uiso 1 1 calc R . . . .
C26 C 0.91688(9) 0.17146(16) 0.15040(9) 0.0418(4) Uani 1 1 d . . . . .
H26 H 0.956923 0.180229 0.185560 0.050 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 '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
O1 S1 O2 121.58(8) . . ?
O1 S1 N1 106.41(7) . . ?
O1 S1 C21 107.43(8) . . ?
O2 S1 N1 105.16(7) . . ?
O2 S1 C21 109.38(8) . . ?
N1 S1 C21 105.83(7) . . ?
C9 S3 C2 101.23(7) . . ?
C1 N1 S1 118.18(10) . . ?
C1 N1 C11 119.80(13) . . ?
C11 N1 S1 118.76(10) . . ?
C10 N2 C1 155.26(16) . . ?
N2 C1 N1 118.86(13) . . ?
C2 C1 N1 121.36(13) . . ?
C2 C1 N2 119.73(14) . . ?
C1 C2 S3 115.66(11) . . ?
C1 C2 C3 124.61(13) . . ?
C3 C2 S3 119.65(11) . . ?
C4 C3 C2 120.23(13) . . ?
C8 C3 C2 120.11(14) . . ?
C8 C3 C4 119.66(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.93(14) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.37(16) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.67(15) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.73(15) . . ?
C8 C7 H7 119.6 . . ?
C3 C8 H8 120.2 . . ?
C7 C8 C3 119.62(15) . . ?
C7 C8 H8 120.2 . . ?
N3 C9 S3 174.74(16) . . ?
N2 C10 S2 177.43(18) . . ?
C12 C11 N1 118.92(13) . . ?
C16 C11 N1 121.13(13) . . ?
C16 C11 C12 119.94(14) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.74(15) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.61(15) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C17 119.80(14) . . ?
C15 C14 C13 117.30(14) . . ?
C15 C14 C17 122.89(14) . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.78(14) . . ?
C16 C15 H15 119.1 . . ?
C11 C16 C15 119.60(14) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C14 C17 C19 109.09(13) . . ?
C14 C17 C20 109.97(13) . . ?
C18 C17 C14 111.62(13) . . ?
C18 C17 C19 108.70(13) . . ?
C18 C17 C20 107.89(14) . . ?
C19 C17 C20 109.53(13) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 S1 118.52(13) . . ?
C26 C21 S1 120.33(13) . . ?
C26 C21 C22 121.13(16) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 C21 119.11(17) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.20(18) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.25(19) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.79(19) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 118.48(18) . . ?
C21 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
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 O1 1.4234(12) . ?
S1 O2 1.4272(12) . ?
S1 N1 1.6665(14) . ?
S1 C21 1.7593(17) . ?
S2 C10 1.5576(17) . ?
S3 C2 1.7785(15) . ?
S3 C9 1.6865(17) . ?
N1 C1 1.4193(19) . ?
N1 C11 1.4481(19) . ?
N2 C1 1.3873(19) . ?
N2 C10 1.173(2) . ?
N3 C9 1.144(2) . ?
C1 C2 1.339(2) . ?
C2 C3 1.478(2) . ?
C3 C4 1.389(2) . ?
C3 C8 1.387(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.375(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(2) . ?
C8 H8 0.9500 . ?
C11 C12 1.386(2) . ?
C11 C16 1.380(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.399(2) . ?
C14 C15 1.385(2) . ?
C14 C17 1.530(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.528(2) . ?
C17 C19 1.534(2) . ?
C17 C20 1.535(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.390(2) . ?
C21 C26 1.384(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.381(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.377(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.373(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(3) . ?
C26 H26 0.9500 . ?
