##############################################################################
# #
# This CIF contains the data for a data article accepted for #
# publication in IUCrData. It conforms to the requirements of #
# Notes for Authors for IUCrData, and has been #
# peer reviewed under the auspices of IUCrData. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. #
# #
# Software is freely available for graphical display of the structure(s) #
# in this CIF. For information consult the CIF software page #
# http://www.iucr.org/resources/cif/software. #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the data #
# article from which it was obtained. #
# #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_chemical_name_systematic
;
5,6-Dihydro-1,4-dithiine-2,3-dicarboxylic anhydride
;
_chemical_formula_moiety 'C6 H4 O3 S2'
_chemical_formula_sum 'C6 H4 O3 S2'
_chemical_formula_iupac 'C6 H4 O3 S2'
_chemical_formula_weight 188.229
_space_group_crystal_system triclinic
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
_cell_length_a 5.3980(10)
_cell_length_b 7.5537(15)
_cell_length_c 9.2566(18)
_cell_angle_alpha 89.273(6)
_cell_angle_beta 87.361(6)
_cell_angle_gamma 75.701(5)
_cell_volume 365.36(12)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 7641
_cell_measurement_theta_min 2.78
_cell_measurement_theta_max 27.35
_cell_measurement_temperature 295(2)
_exptl_crystal_description plate
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.42
_exptl_crystal_size_mid 0.38
_exptl_crystal_size_min 0.17
_exptl_crystal_density_diffrn 1.711
_exptl_crystal_F_000 192.603
_exptl_absorpt_coefficient_mu 0.675
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_absorpt_correction_T_min 0.6478
_exptl_absorpt_correction_T_max 0.7456
_diffrn_ambient_temperature 295.15
_diffrn_source_power 1.0
_diffrn_source_voltage 50.0
_diffrn_source_current 20.0
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_device_type 'Bruker D8 Quest Eco'
_diffrn_measurement_method '\f and \w scans'
_diffrn_reflns_number 16978
_diffrn_reflns_av_R_equivalents 0.0455
_diffrn_reflns_av_unetI/netI 0.0245
_diffrn_reflns_theta_min 3.55
_diffrn_reflns_theta_max 27.55
_diffrn_reflns_theta_full 25.2417
_diffrn_measured_fraction_theta_max 0.9935
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_standards_number 0
_reflns_number_total 1669
_reflns_number_gt 1338
_reflns_threshold_expression I>=2u(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0500
_refine_ls_R_factor_gt 0.0333
_refine_ls_wR_factor_gt 0.0659
_refine_ls_wR_factor_ref 0.0739
_refine_ls_goodness_of_fit_ref 1.1095
_refine_ls_restrained_S_all 1.1095
_refine_ls_number_reflns 1669
_refine_ls_number_parameters 136
_refine_ls_number_restraints 0
_refine_ls_number_constraints 0
_refine_ls_hydrogen_treatment refall
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0229P)^2^+0.1706P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary dual
_refine_ls_shift/su_max 0.0002
_refine_ls_shift/su_mean 0.0000
_refine_diff_density_max 0.4536
_refine_diff_density_min -0.2487
loop_
_atom_type_symbol
_atom_type_scat_dispersion_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C custom 0.00310 0.00160 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
H custom 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
O custom 0.01080 0.00610 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
S custom 0.12480 0.12450 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b) and
olex2.refine (Bourhis et al., 2015)
;
_computing_molecular_graphics
;
OLEX2 1(Dolomanov et al., 2009),
Mercury (Macrae et al., 2020) and
WebMO (Schmidt & Polik, 2016)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
loop_
_atom_site_type_symbol
_atom_site_label
_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
S S1 0.87227(9) 0.35661(7) 0.38382(6) 0.04127(16) Uani 1.000000
S S2 0.45568(10) 0.23942(8) 0.13318(6) 0.04824(17) Uani 1.000000
C C1 0.8444(5) 0.1333(3) 0.3315(2) 0.0440(5) Uani 1.000000
H H1a 1.028(5) 0.039(4) 0.347(3) 0.091(10) Uani 1.000000
H H1b 0.700(5) 0.098(3) 0.400(3) 0.072(8) Uani 1.000000
C C2 0.7794(4) 0.1195(3) 0.1758(2) 0.0440(5) Uani 1.000000
H H2a 0.793(6) -0.019(4) 0.152(3) 0.086(9) Uani 1.000000
H H2b 0.909(5) 0.169(4) 0.102(3) 0.064(8) Uani 1.000000
C C3 0.6129(3) 0.4890(2) 0.3010(2) 0.0338(4) Uani 1.000000
C C4 0.4505(3) 0.4463(2) 0.2093(2) 0.0347(4) Uani 1.000000
C C5 0.5328(4) 0.6869(3) 0.3268(2) 0.0457(5) Uani 1.000000
C C6 0.2545(4) 0.6150(3) 0.1802(2) 0.0478(5) Uani 1.000000
O O1 0.6268(4) 0.7808(2) 0.3987(2) 0.0682(5) Uani 1.000000
O O2 0.3162(3) 0.75751(18) 0.25156(17) 0.0558(4) Uani 1.000000
O O3 0.0695(3) 0.6399(2) 0.11090(19) 0.0695(5) Uani 1.000000
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0364(3) 0.0389(3) 0.0489(3) -0.0100(2) -0.0021(2) -0.0005(2)
S2 0.0401(3) 0.0441(3) 0.0610(4) -0.0107(2) -0.0014(2) -0.0144(3)
C1 0.0523(14) 0.0263(10) 0.0484(13) -0.0007(10) 0.0016(11) 0.0030(9)
H1a 0.08(2) 0.057(19) 0.10(2) 0.045(17) -0.031(18) 0.019(17)
H1b 0.09(2) 0.033(15) 0.10(2) -0.030(15) 0.015(18) -0.009(15)
C2 0.0464(12) 0.0299(11) 0.0496(13) 0.0014(9) 0.0061(10) -0.0076(10)
H2a 0.13(3) 0.038(16) 0.09(2) -0.012(17) 0.007(18) -0.021(15)
H2b 0.053(17) 0.076(19) 0.060(17) -0.013(15) 0.022(13) 0.014(15)
C3 0.0335(9) 0.0236(9) 0.0427(10) -0.0055(7) 0.0074(8) -0.0008(8)
C4 0.0306(9) 0.0281(9) 0.0415(10) -0.0011(7) 0.0060(8) 0.0003(8)
C5 0.0551(13) 0.0245(10) 0.0556(13) -0.0096(9) 0.0171(10) -0.0021(9)
C6 0.0370(11) 0.0442(12) 0.0528(12) 0.0054(9) 0.0076(10) 0.0118(10)
O1 0.0867(13) 0.0358(9) 0.0862(12) -0.0262(9) 0.0178(10) -0.0185(9)
O2 0.0611(10) 0.0270(7) 0.0673(10) 0.0084(7) 0.0161(8) 0.0070(7)
O3 0.0467(9) 0.0712(12) 0.0784(12) 0.0086(8) -0.0076(9) 0.0218(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . 1.805(2) y
S1 C3 . 1.7136(19) y
S2 C2 . 1.817(2) y
S2 C4 . 1.7160(19) y
C1 H1a . 1.08(2) ?
C1 H1b . 1.06(2) ?
C1 C2 . 1.510(3) y
C2 H2a . 1.06(2) ?
C2 H2b . 1.08(2) ?
C3 C4 . 1.345(3) y
C3 C5 . 1.469(3) y
C4 C6 . 1.472(3) y
O1 C5 . 1.193(3) y
O2 C5 . 1.376(3) y
O2 C6 . 1.386(3) y
O3 C6 . 1.186(3) y
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C3 . . 99.54(10) y
C2 S2 C4 . . 98.30(10) y
S1 C1 H1a . . 107.2(15) ?
S1 C1 H1b . . 108.1(12) ?
H1a C1 H1b . . 110(2) ?
S1 C1 C2 . . 114.41(15) y
C2 C1 H1a . . 107.8(16) ?
C2 C1 H1b . . 108.9(15) ?
C1 C2 S2 . . 115.01(15) y
S2 C2 H2a . . 105.1(17) ?
S2 C2 H2b . . 107.5(13) ?
C1 C2 H2a . . 108.8(16) ?
C1 C2 H2b . . 111.8(14) ?
H2a C2 H2b . . 108(2) ?
S1 C3 C4 . . 131.57(14) y
S1 C3 C5 . . 120.60(16) y
C4 C3 C5 . . 107.83(17) y
C3 C4 S2 . . 129.27(14) y
C6 C4 S2 . . 123.28(16) y
C3 C4 C6 . . 107.44(17) y
O1 C5 C3 . . 129.7(2) y
O2 C5 C3 . . 108.36(18) y
O1 C5 O2 . . 121.98(19) y
O2 C6 C4 . . 108.13(18) y
O3 C6 C4 . . 130.7(2) y
O2 C6 O3 . . 121.2(2) y
C5 O2 C6 . . 108.14(15) y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S1 C1 C2 S2 . . . . -70.39(17) ?
S1 C3 C4 S2 . . . . -3.9(2) ?
S1 C3 C4 C6 . . . . 176.69(19) ?
S1 C3 C5 O1 . . . . 1.95(19) ?
S1 C3 C5 O2 . . . . -177.86(15) ?
S2 C4 C3 C5 . . . . 176.57(18) ?
S2 C4 C6 O2 . . . . -176.39(17) ?
S2 C4 C6 O3 . . . . 4.1(2) ?
C3 C4 C6 O2 . . . . 3.05(16) ?
C3 C4 C6 O3 . . . . -176.50(17) ?
C3 C5 O2 C6 . . . . 0.24(18) ?
C4 C6 O2 C5 . . . . -1.95(18) ?
C5 O2 C6 O3 . . . . 177.65(17) ?
_iucr_refine_instructions_details
;
TITL TeamSO01_0m_a.res in P-1
CELL 0.71073 5.398 7.5537 9.2566 89.273 87.361 75.701
ZERR 2 0.001 0.0015 0.0018 0.006 0.006 0.005
LATT 1
SFAC C H O S
DISP C 0.0031 0.0016 11.5003
DISP H 0 0 0.624
DISP O 0.0108 0.0061 32.4922
DISP S 0.1248 0.1245 532.097
UNIT 12 8 6 4
L.S. 4
PLAN 20
TEMP 22
CONF
FMAP 2
ACTA
BOND $H
LIST 4
MORE -1
MERG 2
OMIT 0 1 0
WGHT 0.022859 0.170605
FVAR 0.813546
REM
REM
REM
S1 4 0.87227 0.35661 0.38382 11.00000 0.03636 0.03895 0.04891 =
-0.00050 -0.00213 -0.01002
S2 4 0.45568 0.23942 0.13318 11.00000 0.04013 0.04406 0.06100 =
-0.01444 -0.00141 -0.01072
C1 1 0.84440 0.13325 0.33147 11.00000 0.05229 0.02626 0.04835 =
0.00299 0.00164 -0.00067
H1a 2 1.02761 0.03878 0.34709 11.00000 0.08275 0.05696 0.10403 =
0.01931 -0.03124 0.04457
H1b 2 0.69976 0.09792 0.39974 11.00000 0.08887 0.03287 0.09934 =
-0.00918 0.01481 -0.03015
C2 1 0.77940 0.11949 0.17578 11.00000 0.04644 0.02986 0.04955 =
-0.00763 0.00606 0.00141
H2a 2 0.79289 -0.01938 0.15153 11.00000 0.12772 0.03845 0.08805 =
-0.02101 0.00718 -0.01184
H2b 2 0.90932 0.16868 0.10208 11.00000 0.05300 0.07552 0.05962 =
0.01426 0.02165 -0.01270
C3 1 0.61291 0.48903 0.30096 11.00000 0.03353 0.02356 0.04274 =
-0.00079 0.00743 -0.00546
C4 1 0.45048 0.44634 0.20930 11.00000 0.03056 0.02814 0.04152 =
0.00031 0.00597 -0.00108
C5 1 0.53284 0.68690 0.32678 11.00000 0.05505 0.02451 0.05562 =
-0.00212 0.01707 -0.00959
C6 1 0.25450 0.61504 0.18017 11.00000 0.03703 0.04421 0.05281 =
0.01182 0.00759 0.00536
O1 3 0.62679 0.78081 0.39868 11.00000 0.08668 0.03580 0.08623 =
-0.01850 0.01777 -0.02616
O2 3 0.31621 0.75751 0.25156 11.00000 0.06113 0.02696 0.06726 =
0.00700 0.01613 0.00840
O3 3 0.06951 0.63990 0.11090 11.00000 0.04665 0.07120 0.07844 =
0.02181 -0.00760 0.00865
HKLF 4
END
Q1 1 0.888889 0.36 0.28125 11 0.05 0.45
Q2 1 0.444444 0.24 0.21875 11 0.05 0.42
Q8 1 0.722222 0.44 0.375 11 0.05 0.24
Q3 1 0.5 0.32 0.125 11 0.05 0.37
Q4 1 0.944444 0.2 0.21875 11 0.05 0.28
Q5 1 0.333333 0.28 0.09375 11 0.05 0.26
Q6 1 0.555556 0.76 0.5 11 0.05 0.26
Q7 1 0.555556 0.16 0.09375 11 0.05 0.25
Q9 1 0.166667 0.56 0.03125 11 0.05 0.24
Q10 1 0.666667 0.76 0.40625 11 0.05 0.24
REM The information below was added by Olex2.
REM
REM R1 = 0.0333 for 1338 Fo > 4sig(Fo) and 0.0500 for all 1669 data
REM 136 parameters refined using 0 restraints
REM Highest difference peak 0.4536, deepest hole -0.2487
REM Mean Shift 0.0000, Max Shift -0.0002.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0500
REM R1_gt = 0.0333
REM wR_ref = 0.0739
REM GOOF = 1.1095
REM Shift_max = -0.0002
REM Shift_mean = 0.0000
REM Reflections_all = 1669
REM Reflections_gt = 1338
REM Parameters = 136
REM Hole = -0.2487
REM Peak = 0.4536
REM Flack = n/a
;
data_global
_journal_data_validation_number ?
_journal_date_recd_electronic 2023-07-19
_journal_date_accepted 2023-07-25
_journal_name_full 'IUCrData'
_journal_year 2023
_journal_volume 8
_journal_issue 8
_journal_page_first 0
_journal_page_last 0
_journal_paper_category HO
_journal_paper_doi 10.1107/S2414314623006478
_journal_coeditor_code HB4438
_publ_contact_author_name 'Marcus R. Bond'
_publ_contact_author_address
;
Department of Chemistry and Physics
Southeast Missouri State University
Cape Girardeau, MO 63701, USA
;
_publ_contact_author_email mbond@semo.edu
_publ_contact_author_fax ?
_publ_contact_author_phone '1-573-651-2580'
_publ_section_title
;
5,6-Dihydro-1,4-dithiine-2,3-dicarboxylic anhydride
;
_publ_section_title_footnote .
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Bullock, Olivia' .
;
Department of Chemistry and Physics
Southeast Missouri State University
Cape Girardeau
MO 63701
USA
;
'Rice, Sarah' .
;
Department of Chemistry and Physics
Southeast Missouri State University
Cape Girardeau
MO 63701
USA
;
'Bond, Marcus R.' .
;
Department of Chemistry and Physics
Southeast Missouri State University
Cape Girardeau
MO 63701
USA
;
_publ_section_synopsis
;
The heterocyclic fused ring geometry of the title compound coincides with the
geometries of related molecules but without directed intermolecular contacts
determining the crystal packing.
;