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#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/71/7157146.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_7157146
loop_
_publ_author_name
'Heron, Bernard Mark'
'Aiken, Stuart'
'Gabbutt, Christopher'
'Rice, Craig'
'Zonidis, Dimitrios'
_publ_section_title
;
 Synthesis and Photochromism of Some Mono and Bis(Thienyl) Substituted
 Oxathiine 2,2-dioxides
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB02128K
_journal_year                    2019
_chemical_formula_moiety         'C26 H32 N O3.50 S3'
_chemical_formula_sum            'C26 H32 N O3.5 S3'
_chemical_formula_weight         510.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-03-25 deposited with the CCDC.    2019-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                113.322(17)
_cell_angle_beta                 109.14(2)
_cell_angle_gamma                90.79(2)
_cell_formula_units_Z            2
_cell_length_a                   9.869(5)
_cell_length_b                   11.897(5)
_cell_length_c                   13.181(5)
_cell_measurement_reflns_used    7588
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.41
_cell_measurement_theta_min      2.22
_cell_volume                     1324.1(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19176
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.533
_diffrn_reflns_theta_min         2.215
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       plate
_exptl_crystal_F_000             542
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.823
_refine_diff_density_min         -1.120
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         8011
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0519
_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)+(0.0674P)²+0.7738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1481
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5853
_reflns_number_total             8011
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ob02128k2.cif
_cod_data_source_block           ColourChem_DZ050_0m_a
_cod_original_formula_sum        'C26 H32 N O3.50 S3'
_cod_database_code               7157146
_shelx_shelxl_version_number     2017/1
_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, -y, -z'
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 0.58497(5) 0.65186(4) 0.95084(4) 0.02065(11) Uani 1 1 d . . . . .
S2 S 0.71976(6) 0.11741(5) 0.72467(5) 0.03134(14) Uani 1 1 d . . . . .
S3 S 0.45247(7) 0.28499(6) 0.39467(5) 0.03238(14) Uani 1 1 d . . . . .
N1 N 0.18994(18) 0.49473(16) 0.69851(15) 0.0249(3) Uani 1 1 d . . . . .
O1 O 0.63090(16) 0.71421(13) 1.07697(12) 0.0282(3) Uani 1 1 d . . . . .
O2 O 0.66356(15) 0.68777(13) 0.89138(13) 0.0262(3) Uani 1 1 d . . . . .
O3 O 0.58845(15) 0.50804(12) 0.92290(11) 0.0215(3) Uani 1 1 d . . . . .
O4 O 0.000000 1.000000 0.500000 0.0999(12) Uani 1 2 d S U P . .
C1 C 0.5418(2) 0.42454(17) 0.80027(16) 0.0189(3) Uani 1 1 d . . . . .
C2 C 0.4346(2) 0.44505(16) 0.71872(16) 0.0183(3) Uani 1 1 d . . . . .
C3 C 0.3444(2) 0.54895(17) 0.74791(16) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.355190 0.598993 0.704559 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3951(2) 0.64121(17) 0.88189(16) 0.0188(3) Uani 1 1 d . . . . .
H4 H 0.346333 0.604571 0.919995 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6310(2) 0.32586(18) 0.78573(17) 0.0203(4) Uani 1 1 d . . . . .
C6 C 0.5781(2) 0.20119(18) 0.71780(18) 0.0241(4) Uani 1 1 d . . . . .
C7 C 0.4254(3) 0.1345(2) 0.6457(2) 0.0351(5) Uani 1 1 d . . . . .
H7A H 0.359081 0.181235 0.681054 0.053 Uiso 1 1 calc R U . . .
H7B H 0.417357 0.051567 0.644126 0.053 Uiso 1 1 calc R U . . .
H7C H 0.399728 0.126876 0.564576 0.053 Uiso 1 1 calc R U . . .
C8 C 0.7857(2) 0.3507(2) 0.84509(18) 0.0255(4) Uani 1 1 d . . . . .
H8 H 0.838815 0.431910 0.896664 0.031 Uiso 1 1 calc R U . . .
C9 C 0.8497(2) 0.2475(2) 0.8209(2) 0.0294(4) Uani 1 1 d . . . . .
C10 C 0.4091(2) 0.37510(17) 0.59032(16) 0.0194(3) Uani 1 1 d . . . . .
C11 C 0.2713(2) 0.31163(17) 0.49818(17) 0.0227(4) Uani 1 1 d . . . . .
H11 H 0.183973 0.307700 0.513218 0.027 Uiso 1 1 calc R U . . .
C12 C 0.2762(2) 0.25759(19) 0.38751(18) 0.0273(4) Uani 1 1 d . . . . .
C13 C 0.1559(3) 0.1857(2) 0.27035(19) 0.0380(5) Uani 1 1 d . . . . .
H13A H 0.063614 0.181144 0.282579 0.057 Uiso 1 1 calc R U . . .
H13B H 0.176142 0.101618 0.233572 0.057 Uiso 1 1 calc R U . . .
H13C H 0.149398 0.227339 0.218345 0.057 Uiso 1 1 calc R U . . .
C14 C 0.5186(2) 0.37100(19) 0.54645(17) 0.0244(4) Uani 1 1 d . . . . .
C15 C 0.6753(2) 0.4298(2) 0.6086(2) 0.0309(5) Uani 1 1 d . . . . .
H15A H 0.688418 0.498572 0.684986 0.046 Uiso 1 1 calc R U . . .
H15B H 0.705572 0.461257 0.559617 0.046 Uiso 1 1 calc R U . . .
H15C H 0.734639 0.367943 0.621777 0.046 Uiso 1 1 calc R U . . .
C16 C 0.3527(2) 0.76848(17) 0.90341(16) 0.0208(4) Uani 1 1 d . . . . .
C17 C 0.3926(2) 0.84106(19) 0.85351(18) 0.0272(4) Uani 1 1 d . . . . .
H17 H 0.451209 0.812228 0.806788 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3475(3) 0.9552(2) 0.8716(2) 0.0337(5) Uani 1 1 d . . . . .
H18 H 0.375911 1.004620 0.838022 0.040 Uiso 1 1 calc R U . . .
C19 C 0.2607(3) 0.9968(2) 0.9387(2) 0.0377(6) Uani 1 1 d . . . . .
H19 H 0.227627 1.073911 0.949718 0.045 Uiso 1 1 calc R U . . .
C20 C 0.2224(3) 0.9260(2) 0.9895(2) 0.0383(5) Uani 1 1 d . . . . .
H20 H 0.163901 0.955242 1.036257 0.046 Uiso 1 1 calc R U . . .
C21 C 0.2685(2) 0.8122(2) 0.97313(19) 0.0293(4) Uani 1 1 d . . . . .
H21 H 0.242706 0.764590 1.009296 0.035 Uiso 1 1 calc R U . . .
C22 C 0.1473(3) 0.4331(2) 0.7615(2) 0.0370(5) Uani 1 1 d . . . . .
H22A H 0.140287 0.495478 0.834460 0.056 Uiso 1 1 calc R U . . .
H22B H 0.220112 0.382566 0.781381 0.056 Uiso 1 1 calc R U . . .
H22C H 0.052604 0.379683 0.711119 0.056 Uiso 1 1 calc R U . . .
C23 C 0.0886(3) 0.5751(2) 0.6693(2) 0.0424(6) Uani 1 1 d . . . . .
H23A H -0.007849 0.525355 0.617609 0.064 Uiso 1 1 calc R U . . .
H23B H 0.122899 0.615740 0.628433 0.064 Uiso 1 1 calc R U . . .
H23C H 0.082606 0.638272 0.742370 0.064 Uiso 1 1 calc R U . . .
C24 C 0.0814(8) 0.9418(7) 0.5821(7) 0.0723(13) Uani 0.539(6) 1 d . U P A 2
H24A H 0.158021 1.008077 0.650498 0.087 Uiso 0.539(6) 1 calc R U P A 2
H24B H 0.011832 0.919226 0.613309 0.087 Uiso 0.539(6) 1 calc R U P A 2
C25 C 0.1477(18) 0.8383(15) 0.5427(12) 0.074(2) Uani 0.539(6) 1 d . U P A 2
H25A H 0.073742 0.768006 0.479350 0.111 Uiso 0.539(6) 1 calc R U P A 2
H25B H 0.196854 0.816939 0.608796 0.111 Uiso 0.539(6) 1 calc R U P A 2
H25C H 0.219113 0.857411 0.512348 0.111 Uiso 0.539(6) 1 calc R U P A 2
C26 C 0.0542(10) 0.8944(8) 0.4716(8) 0.0731(13) Uani 0.461(6) 1 d . U P A 1
H26A H 0.125916 0.903642 0.436469 0.088 Uiso 0.461(6) 1 calc R U P A 1
H26B H -0.026511 0.828626 0.407361 0.088 Uiso 0.461(6) 1 calc R U P A 1
C27 C 0.1281(19) 0.8432(19) 0.5630(14) 0.069(2) Uani 0.461(6) 1 d . U P A 1
H27A H 0.214275 0.902578 0.625027 0.103 Uiso 0.461(6) 1 calc R U P A 1
H27B H 0.157269 0.763936 0.523499 0.103 Uiso 0.461(6) 1 calc R U P A 1
H27C H 0.059824 0.830523 0.598775 0.103 Uiso 0.461(6) 1 calc R U P A 1
C28 C 1.0071(3) 0.2382(3) 0.8706(3) 0.0439(6) Uani 1 1 d . . . . .
H28A H 1.065453 0.321488 0.912876 0.066 Uiso 1 1 calc R U . . .
H28B H 1.038610 0.187721 0.805723 0.066 Uiso 1 1 calc R U . . .
H28C H 1.020179 0.199356 0.925508 0.066 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'
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
O1 S1 O2 119.33(10) . .
O1 S1 O3 104.79(8) . .
O2 S1 O3 109.40(8) . .
O1 S1 C4 111.51(9) . .
O2 S1 C4 111.22(9) . .
O3 S1 C4 98.24(9) . .
C9 S2 C6 93.45(11) . .
C14 S3 C12 93.32(10) . .
C22 N1 C23 112.51(19) . .
C22 N1 C3 115.09(17) . .
C23 N1 C3 115.21(18) . .
C1 O3 S1 115.64(12) . .
C26 O4 C26 180.0 2_576 .
C26 O4 C24 51.9(4) 2_576 2_576
C26 O4 C24 128.1(4) . 2_576
C24 O4 C24 180.0(4) 2_576 .
C2 C1 O3 120.74(16) . .
C2 C1 C5 130.12(17) . .
O3 C1 C5 109.11(15) . .
C1 C2 C10 120.16(16) . .
C1 C2 C3 124.30(16) . .
C10 C2 C3 115.12(16) . .
N1 C3 C2 109.40(15) . .
N1 C3 C4 112.30(15) . .
C2 C3 C4 115.10(15) . .
N1 C3 H3 106.5 . .
C2 C3 H3 106.5 . .
C4 C3 H3 106.5 . .
C16 C4 C3 113.95(15) . .
C16 C4 S1 111.41(13) . .
C3 C4 S1 109.74(12) . .
C16 C4 H4 107.1 . .
C3 C4 H4 107.1 . .
S1 C4 H4 107.1 . .
C6 C5 C8 112.55(18) . .
C6 C5 C1 125.06(18) . .
C8 C5 C1 122.36(17) . .
C5 C6 C7 130.40(19) . .
C5 C6 S2 110.05(16) . .
C7 C6 S2 119.55(16) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C8 C5 113.92(19) . .
C9 C8 H8 123.0 . .
C5 C8 H8 123.0 . .
C8 C9 C28 128.3(2) . .
C8 C9 S2 110.00(16) . .
C28 C9 S2 121.59(19) . .
C14 C10 C11 112.14(17) . .
C14 C10 C2 122.05(17) . .
C11 C10 C2 125.71(16) . .
C12 C11 C10 114.34(18) . .
C12 C11 H11 122.8 . .
C10 C11 H11 122.8 . .
C11 C12 C13 129.8(2) . .
C11 C12 S3 109.74(16) . .
C13 C12 S3 120.44(16) . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C10 C14 C15 130.37(18) . .
C10 C14 S3 110.41(15) . .
C15 C14 S3 119.20(15) . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C21 C16 C17 119.37(19) . .
C21 C16 C4 118.56(18) . .
C17 C16 C4 122.05(17) . .
C18 C17 C16 120.5(2) . .
C18 C17 H17 119.7 . .
C16 C17 H17 119.7 . .
C19 C18 C17 119.8(2) . .
C19 C18 H18 120.1 . .
C17 C18 H18 120.1 . .
C20 C19 C18 119.9(2) . .
C20 C19 H19 120.1 . .
C18 C19 H19 120.1 . .
C19 C20 C21 120.8(2) . .
C19 C20 H20 119.6 . .
C21 C20 H20 119.6 . .
C20 C21 C16 119.7(2) . .
C20 C21 H21 120.2 . .
C16 C21 H21 120.2 . .
N1 C22 H22A 109.5 . .
N1 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
N1 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
N1 C23 H23A 109.5 . .
N1 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
N1 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C25 C24 O4 121.8(8) . .
C25 C24 H24A 106.9 . .
O4 C24 H24A 106.9 . .
C25 C24 H24B 106.9 . .
O4 C24 H24B 106.9 . .
H24A C24 H24B 106.7 . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
O4 C26 C27 122.6(9) . .
O4 C26 H26A 106.7 . .
C27 C26 H26A 106.7 . .
O4 C26 H26B 106.7 . .
C27 C26 H26B 106.7 . .
H26A C26 H26B 106.6 . .
C26 C27 H27A 109.5 . .
C26 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C26 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C9 C28 H28A 109.5 . .
C9 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C9 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4283(15) .
S1 O2 1.4327(15) .
S1 O3 1.6049(16) .
S1 C4 1.772(2) .
S2 C9 1.724(3) .
S2 C6 1.727(2) .
S3 C14 1.726(2) .
S3 C12 1.730(2) .
N1 C22 1.451(3) .
N1 C23 1.459(3) .
N1 C3 1.467(3) .
O3 C1 1.428(2) .
O4 C26 1.335(9) 2_576
O4 C26 1.335(9) .
O4 C24 1.528(7) 2_576
O4 C24 1.528(7) .
C1 C2 1.343(3) .
C1 C5 1.467(3) .
C2 C10 1.490(2) .
C2 C3 1.532(3) .
C3 C4 1.563(3) .
C3 H3 1.0000 .
C4 C16 1.518(3) .
C4 H4 1.0000 .
C5 C6 1.377(3) .
C5 C8 1.432(3) .
C6 C7 1.495(3) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C9 1.362(3) .
C8 H8 0.9500 .
C9 C28 1.499(3) .
C10 C14 1.376(3) .
C10 C11 1.434(3) .
C11 C12 1.359(3) .
C11 H11 0.9500 .
C12 C13 1.500(3) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C15 1.496(3) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C21 1.393(3) .
C16 C17 1.394(3) .
C17 C18 1.389(3) .
C17 H17 0.9500 .
C18 C19 1.387(4) .
C18 H18 0.9500 .
C19 C20 1.381(4) .
C19 H19 0.9500 .
C20 C21 1.391(3) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 C25 1.397(18) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 C27 1.54(2) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353097
