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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/43/4034356.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.
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data_4034356
loop_
_publ_author_name
'Schneeweis, Arno P. W.'
'Hauer, Simone T.'
'Lopez, Daniel A.'
'von Dressler, Björn'
'Reiss, Guido J.'
'Müller, Thomas J J'
_publ_section_title
;
 Game of Isomers: Bifurcation in the Catalytic Formation of
 Bis[1]benzothieno[1,4]thiazines with Conformation-Dependent Electronic
 Properties.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5582
_journal_page_last               5595
_journal_paper_doi               10.1021/acs.joc.9b00517
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C18 H17 N S'
_chemical_formula_weight         279.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 98.747(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1973(5)
_cell_length_b                   31.092(3)
_cell_length_c                   7.8625(7)
_cell_measurement_reflns_used    1399
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      28.9
_cell_measurement_theta_min      3.3
_cell_volume                     1497.4(2)
_computing_cell_refinement       'CrysAlisPRO, AGILENT'
_computing_data_collection       'CrysAlisPRO, AGILENT'
_computing_data_reduction        'CrysAlisPRO, AGILENT'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 16.2711
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  Xcalibur-EOS
_diffrn_measurement_method       omega
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.1379
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6555
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.996
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         3.277
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44  
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1695
_refine_ls_R_factor_gt           0.0659
_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)+(0.0110P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1371
_reflns_number_total             2921
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b00517_si_005.cif
_cod_data_source_block           exp_1110RT_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034356
_shelx_shelxl_version_number     2018/1
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
S1 S 0.73584(15) 0.50480(3) -0.22010(11) 0.0488(3) Uani 1 1 d . .
N1 N 0.9300(5) 0.43966(9) 0.1949(4) 0.0481(9) Uani 1 1 d . .
C1 C 0.9058(5) 0.48994(11) -0.0311(4) 0.0370(9) Uani 1 1 d . .
C2 C 0.8171(6) 0.45283(11) 0.0532(4) 0.0394(9) Uani 1 1 d . .
C3 C 0.6092(6) 0.43869(11) -0.0446(4) 0.0393(9) Uani 1 1 d . .
C4 C 0.4733(6) 0.40454(12) -0.0112(4) 0.0509(11) Uani 1 1 d . .
H4 H 0.512024 0.386848 0.083893 0.061 Uiso 1 1 calc R U
C5 C 0.2818(7) 0.39768(13) -0.1220(5) 0.0607(12) Uani 1 1 d . .
H5 H 0.190971 0.375103 -0.101015 0.073 Uiso 1 1 calc R U
C6 C 0.2219(6) 0.42391(14) -0.2642(5) 0.0600(12) Uani 1 1 d . .
H6 H 0.091118 0.418986 -0.336758 0.072 Uiso 1 1 calc R U
C7 C 0.3555(6) 0.45715(13) -0.2983(5) 0.0531(11) Uani 1 1 d . .
H7 H 0.315390 0.474829 -0.393213 0.064 Uiso 1 1 calc R U
C8 C 0.5502(6) 0.46402(11) -0.1897(4) 0.0413(10) Uani 1 1 d . .
C9 C 0.8638(6) 0.40446(12) 0.2910(4) 0.0422(10) Uani 1 1 d . .
C10 C 0.9594(6) 0.36495(13) 0.2835(5) 0.0573(11) Uani 1 1 d . .
H10 H 1.061815 0.360860 0.209957 0.069 Uiso 1 1 calc R U
C11 C 0.9070(6) 0.33114(12) 0.3828(5) 0.0530(11) Uani 1 1 d . .
H11 H 0.971726 0.304482 0.372306 0.064 Uiso 1 1 calc R U
C12 C 0.7604(6) 0.33586(12) 0.4979(4) 0.0396(9) Uani 1 1 d . .
C13 C 0.6690(6) 0.37611(12) 0.5067(4) 0.0491(11) Uani 1 1 d . .
H13 H 0.569150 0.380582 0.582104 0.059 Uiso 1 1 calc R U
C14 C 0.7215(6) 0.40998(12) 0.4067(4) 0.0485(10) Uani 1 1 d . .
H14 H 0.659467 0.436868 0.418142 0.058 Uiso 1 1 calc R U
C15 C 0.7020(6) 0.29953(12) 0.6130(4) 0.0455(10) Uani 1 1 d . .
C16 C 0.4527(6) 0.29484(13) 0.5940(5) 0.0730(13) Uani 1 1 d . .
H16A H 0.394278 0.290418 0.475045 0.110 Uiso 1 1 calc R U
H16B H 0.391190 0.320500 0.634669 0.110 Uiso 1 1 calc R U
H16C H 0.416985 0.270663 0.660356 0.110 Uiso 1 1 calc R U
C17 C 0.7880(7) 0.31119(12) 0.8012(4) 0.0666(13) Uani 1 1 d . .
H17A H 0.944547 0.312446 0.817488 0.100 Uiso 1 1 calc R U
H17B H 0.742210 0.289724 0.875903 0.100 Uiso 1 1 calc R U
H17C H 0.730872 0.338681 0.827686 0.100 Uiso 1 1 calc R U
C18 C 0.7984(7) 0.25619(12) 0.5718(5) 0.0689(13) Uani 1 1 d . .
H18A H 0.748963 0.248981 0.453576 0.103 Uiso 1 1 calc R U
H18B H 0.751915 0.234389 0.644770 0.103 Uiso 1 1 calc R U
H18C H 0.954857 0.257970 0.591229 0.103 Uiso 1 1 calc R U
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'
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
C1 S1 C8 90.93(16) .
C2 N1 C9 122.7(3) .
C1 C1 C2 124.0(4) 3_765
C1 C1 S1 124.2(3) 3_765
C2 C1 S1 111.8(2) .
N1 C2 C3 132.6(3) .
N1 C2 C1 116.5(3) .
C3 C2 C1 110.9(3) .
C8 C3 C4 119.4(3) .
C8 C3 C2 111.2(3) .
C4 C3 C2 129.3(3) .
C5 C4 C3 118.8(4) .
C5 C4 H4 120.6 .
C3 C4 H4 120.6 .
C4 C5 C6 121.1(4) .
C4 C5 H5 119.4 .
C6 C5 H5 119.4 .
C7 C6 C5 120.2(4) .
C7 C6 H6 119.9 .
C5 C6 H6 119.9 .
C6 C7 C8 119.3(4) .
C6 C7 H7 120.3 .
C8 C7 H7 120.3 .
C7 C8 C3 121.0(3) .
C7 C8 S1 123.8(3) .
C3 C8 S1 115.2(3) .
C10 C9 C14 117.9(3) .
C10 C9 N1 120.3(3) .
C14 C9 N1 121.5(3) .
C9 C10 C11 121.3(3) .
C9 C10 H10 119.4 .
C11 C10 H10 119.4 .
C10 C11 C12 121.6(4) .
C10 C11 H11 119.2 .
C12 C11 H11 119.2 .
C13 C12 C11 116.4(3) .
C13 C12 C15 120.4(3) .
C11 C12 C15 123.2(3) .
C12 C13 C14 121.9(3) .
C12 C13 H13 119.0 .
C14 C13 H13 119.0 .
C9 C14 C13 120.9(4) .
C9 C14 H14 119.6 .
C13 C14 H14 119.6 .
C12 C15 C18 113.1(3) .
C12 C15 C16 109.8(3) .
C18 C15 C16 108.4(3) .
C12 C15 C17 108.5(3) .
C18 C15 C17 108.8(3) .
C16 C15 C17 108.2(3) .
C15 C16 H16A 109.5 .
C15 C16 H16B 109.5 .
H16A C16 H16B 109.5 .
C15 C16 H16C 109.5 .
H16A C16 H16C 109.5 .
H16B C16 H16C 109.5 .
C15 C17 H17A 109.5 .
C15 C17 H17B 109.5 .
H17A C17 H17B 109.5 .
C15 C17 H17C 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
C15 C18 H18A 109.5 .
C15 C18 H18B 109.5 .
H18A C18 H18B 109.5 .
C15 C18 H18C 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.748(3) .
S1 C8 1.753(4) .
N1 C2 1.289(4) .
N1 C9 1.425(4) .
C1 C1 1.349(6) 3_765
C1 C2 1.478(4) .
C2 C3 1.464(4) .
C3 C8 1.389(4) .
C3 C4 1.405(4) .
C4 C5 1.378(5) .
C4 H4 0.9300 .
C5 C6 1.388(5) .
C5 H5 0.9300 .
C6 C7 1.376(5) .
C6 H6 0.9300 .
C7 C8 1.384(4) .
C7 H7 0.9300 .
C9 C10 1.369(5) .
C9 C14 1.371(4) .
C10 C11 1.378(4) .
C10 H10 0.9300 .
C11 C12 1.384(4) .
C11 H11 0.9300 .
C12 C13 1.380(4) .
C12 C15 1.525(4) .
C13 C14 1.382(4) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 C18 1.529(5) .
C15 C16 1.536(5) .
C15 C17 1.538(4) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C8 S1 C1 C1 -178.8(4) . 3_765
C8 S1 C1 C2 0.7(3) . .
C9 N1 C2 C3 0.7(6) . .
C9 N1 C2 C1 179.5(3) . .
C1 C1 C2 N1 0.1(6) 3_765 .
S1 C1 C2 N1 -179.4(2) . .
C1 C1 C2 C3 179.2(4) 3_765 .
S1 C1 C2 C3 -0.3(3) . .
N1 C2 C3 C8 178.5(4) . .
C1 C2 C3 C8 -0.4(4) . .
N1 C2 C3 C4 -2.1(6) . .
C1 C2 C3 C4 179.0(3) . .
C8 C3 C4 C5 -1.5(5) . .
C2 C3 C4 C5 179.2(3) . .
C3 C4 C5 C6 -0.1(6) . .
C4 C5 C6 C7 0.7(6) . .
C5 C6 C7 C8 0.3(5) . .
C6 C7 C8 C3 -1.9(5) . .
C6 C7 C8 S1 179.3(3) . .
C4 C3 C8 C7 2.5(5) . .
C2 C3 C8 C7 -178.0(3) . .
C4 C3 C8 S1 -178.6(3) . .
C2 C3 C8 S1 0.9(4) . .
C1 S1 C8 C7 178.0(3) . .
C1 S1 C8 C3 -0.9(3) . .
C2 N1 C9 C10 102.5(4) . .
C2 N1 C9 C14 -84.6(4) . .
C14 C9 C10 C11 3.1(6) . .
N1 C9 C10 C11 176.2(3) . .
C9 C10 C11 C12 -1.9(6) . .
C10 C11 C12 C13 0.4(5) . .
C10 C11 C12 C15 -178.6(3) . .
C11 C12 C13 C14 -0.3(5) . .
C15 C12 C13 C14 178.7(3) . .
C10 C9 C14 C13 -3.0(5) . .
N1 C9 C14 C13 -176.0(3) . .
C12 C13 C14 C9 1.6(6) . .
C13 C12 C15 C18 173.6(3) . .
C11 C12 C15 C18 -7.4(5) . .
C13 C12 C15 C16 52.4(4) . .
C11 C12 C15 C16 -128.6(4) . .
C13 C12 C15 C17 -65.6(4) . .
C11 C12 C15 C17 113.3(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328269
