# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1S
_database_code_depnum_ccdc_archive 'CCDC 2332628'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H2 N2 O2 S'
_chemical_formula_sum            'C3 H2 N2 O2 S'
_chemical_formula_weight         130.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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'

_cell_length_a                   3.68025(19)
_cell_length_b                   9.5291(6)
_cell_length_c                   13.5746(7)
_cell_angle_alpha                83.751(5)
_cell_angle_beta                 87.678(4)
_cell_angle_gamma                81.873(5)
_cell_volume                     468.32(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5413
_cell_measurement_theta_min      4.7070
_cell_measurement_theta_max      75.7340

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    5.291
_shelx_estimated_absorpt_T_min   0.226
_shelx_estimated_absorpt_T_max   0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40045
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5384
_diffrn_reflns_number            6541
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.276
_diffrn_reflns_theta_max         76.452
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1932
_reflns_number_gt                1889
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0960P)²+0.2391P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1932
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1346
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
S2A S 0.74728(13) 0.38510(5) 0.60198(4) 0.0236(2) Uani 1 1 d . . . . .
S2B S 1.00714(14) 0.12080(5) 0.10049(4) 0.0241(2) Uani 1 1 d . . . . .
O1A O 0.4187(5) 0.37315(17) 0.91163(12) 0.0281(4) Uani 1 1 d . . . . .
H1A H 0.331742 0.358284 0.969395 0.042 Uiso 1 1 calc R U . . .
O1B O 0.7607(5) 0.12591(17) 0.41403(12) 0.0290(4) Uani 1 1 d . . . . .
H1B H 0.722202 0.142320 0.473389 0.044 Uiso 1 1 calc R U . . .
O2B O 0.9804(5) 0.33548(18) 0.39953(12) 0.0310(4) Uani 1 1 d . . . . .
O2A O 0.2463(5) 0.16076(18) 0.89421(11) 0.0308(4) Uani 1 1 d . . . . .
N3B N 0.9012(5) 0.1006(2) 0.21767(13) 0.0247(4) Uani 1 1 d . . . . .
N1A N 0.6483(5) 0.22265(19) 0.59983(13) 0.0247(4) Uani 1 1 d . . . . .
N3A N 0.6352(5) 0.40339(19) 0.71702(14) 0.0242(4) Uani 1 1 d . . . . .
N1B N 1.1347(5) 0.27988(19) 0.09624(14) 0.0251(4) Uani 1 1 d . . . . .
C4A C 0.5151(5) 0.2838(2) 0.75604(15) 0.0235(4) Uani 1 1 d . . . . .
C5A C 0.5223(6) 0.1799(2) 0.68892(16) 0.0242(4) Uani 1 1 d . . . . .
H5A H 0.445060 0.089182 0.706036 0.029 Uiso 1 1 calc R U . . .
C4B C 0.9657(5) 0.2167(2) 0.25645(15) 0.0231(4) Uani 1 1 d . . . . .
C6B C 0.9045(6) 0.2329(2) 0.36416(16) 0.0246(4) Uani 1 1 d . . . . .
C5B C 1.0985(6) 0.3200(2) 0.18673(16) 0.0249(4) Uani 1 1 d . . . . .
H5B H 1.155594 0.408644 0.203145 0.030 Uiso 1 1 calc R U . . .
C6A C 0.3808(5) 0.2653(2) 0.86123(15) 0.0242(4) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S2A 0.0274(3) 0.0199(3) 0.0234(3) -0.0032(2) 0.0013(2) -0.0032(2)
S2B 0.0282(3) 0.0205(3) 0.0242(3) -0.0054(2) 0.0015(2) -0.0039(2)
O1A 0.0404(9) 0.0222(8) 0.0228(7) -0.0052(6) 0.0043(6) -0.0080(6)
O1B 0.0418(9) 0.0227(8) 0.0242(7) -0.0054(6) 0.0061(6) -0.0096(7)
O2B 0.0417(9) 0.0256(8) 0.0275(8) -0.0083(6) 0.0028(6) -0.0082(7)
O2A 0.0409(9) 0.0263(8) 0.0268(8) -0.0048(6) 0.0053(7) -0.0108(7)
N3B 0.0262(9) 0.0234(9) 0.0248(9) -0.0059(7) 0.0013(7) -0.0023(7)
N1A 0.0267(9) 0.0202(9) 0.0266(9) -0.0026(7) 0.0001(7) -0.0011(7)
N3A 0.0261(9) 0.0207(9) 0.0259(9) -0.0040(7) 0.0005(7) -0.0025(7)
N1B 0.0271(9) 0.0206(9) 0.0277(9) -0.0054(7) 0.0008(7) -0.0017(7)
C4A 0.0233(10) 0.0202(10) 0.0261(10) -0.0034(8) -0.0005(8) 0.0008(8)
C5A 0.0243(9) 0.0218(10) 0.0258(10) -0.0036(8) 0.0000(7) 0.0002(8)
C4B 0.0213(9) 0.0211(10) 0.0268(10) -0.0065(8) -0.0009(7) 0.0001(7)
C6B 0.0250(10) 0.0223(10) 0.0258(10) -0.0050(8) 0.0013(8) 0.0007(8)
C5B 0.0253(10) 0.0237(10) 0.0251(10) -0.0055(8) 0.0002(7) 0.0001(8)
C6A 0.0245(10) 0.0221(10) 0.0251(10) -0.0034(8) 0.0015(8) -0.0002(8)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S2A N3A 1.6204(18) . ?
S2A N1A 1.6432(19) . ?
S2B N3B 1.6197(18) . ?
S2B N1B 1.6438(19) . ?
O1A C6A 1.321(3) . ?
O1A H1A 0.8400 . ?
O1B C6B 1.324(3) . ?
O1B H1B 0.8400 . ?
O2B C6B 1.206(3) . ?
O2A C6A 1.209(3) . ?
N3B C4B 1.330(3) . ?
N1A C5A 1.321(3) . ?
N3A C4A 1.329(3) . ?
N1B C5B 1.322(3) . ?
C4A C5A 1.414(3) . ?
C4A C6A 1.492(3) . ?
C5A H5A 0.9500 . ?
C4B C5B 1.414(3) . ?
C4B C6B 1.492(3) . ?
C5B H5B 0.9500 . ?

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
N3A S2A N1A 97.99(9) . . ?
N3B S2B N1B 97.94(9) . . ?
C6A O1A H1A 109.5 . . ?
C6B O1B H1B 109.5 . . ?
C4B N3B S2B 107.63(15) . . ?
C5A N1A S2A 107.90(15) . . ?
C4A N3A S2A 107.45(15) . . ?
C5B N1B S2B 107.86(16) . . ?
N3A C4A C5A 114.00(19) . . ?
N3A C4A C6A 121.71(19) . . ?
C5A C4A C6A 124.28(19) . . ?
N1A C5A C4A 112.66(19) . . ?
N1A C5A H5A 123.7 . . ?
C4A C5A H5A 123.7 . . ?
N3B C4B C5B 113.83(18) . . ?
N3B C4B C6B 122.01(19) . . ?
C5B C4B C6B 124.16(19) . . ?
O2B C6B O1B 125.1(2) . . ?
O2B C6B C4B 121.5(2) . . ?
O1B C6B C4B 113.39(18) . . ?
N1B C5B C4B 112.73(19) . . ?
N1B C5B H5B 123.6 . . ?
C4B C5B H5B 123.6 . . ?
O2A C6A O1A 124.88(19) . . ?
O2A C6A C4A 121.4(2) . . ?
O1A C6A C4A 113.73(18) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1B S2B N3B C4B -0.53(16) . . . . ?
N3A S2A N1A C5A 0.56(16) . . . . ?
N1A S2A N3A C4A -0.56(16) . . . . ?
N3B S2B N1B C5B 0.31(16) . . . . ?
S2A N3A C4A C5A 0.4(2) . . . . ?
S2A N3A C4A C6A -178.70(15) . . . . ?
S2A N1A C5A C4A -0.4(2) . . . . ?
N3A C4A C5A N1A 0.0(3) . . . . ?
C6A C4A C5A N1A 179.07(18) . . . . ?
S2B N3B C4B C5B 0.6(2) . . . . ?
S2B N3B C4B C6B -178.82(15) . . . . ?
N3B C4B C6B O2B 176.4(2) . . . . ?
C5B C4B C6B O2B -3.0(3) . . . . ?
N3B C4B C6B O1B -4.0(3) . . . . ?
C5B C4B C6B O1B 176.65(19) . . . . ?
S2B N1B C5B C4B 0.0(2) . . . . ?
N3B C4B C5B N1B -0.4(3) . . . . ?
C6B C4B C5B N1B 179.00(18) . . . . ?
N3A C4A C6A O2A 174.4(2) . . . . ?
C5A C4A C6A O2A -4.7(3) . . . . ?
N3A C4A C6A O1A -4.6(3) . . . . ?
C5A C4A C6A O1A 176.41(19) . . . . ?

_refine_diff_density_max         0.871
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.097

_shelx_res_file                  
;
TITL 1S.res in P-1
    1S.res
    created by SHELXL-2019/3 at 12:22:27 on 01-Feb-2024
REM Old TITL S-COOH_auto in P-1
REM SHELXT solution in P-1: R1 0.082, Rweak 0.006, Alpha 0.057
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 N4 O4 Cl2
CELL 1.54184 3.680255 9.529075 13.574583 83.751 87.6775 81.8731
ZERR 4 0.000191 0.000556 0.000709 0.0045 0.0042 0.0046
LATT 1
SFAC C H N O S
UNIT 12 8 8 8 4

L.S. 4 0 0
PLAN  4
SIZE 0.4 0.15 0.05
TEMP -143.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
ACTA
OMIT 2 8 2
OMIT 3 9 2
REM <olex2.extras>
REM <HklSrc "%.\\1S.hkl">
REM </olex2.extras>

WGHT    0.096000    0.239100
FVAR       9.99173
S2A   5    0.747282    0.385099    0.601984    11.00000    0.02744    0.01990 =
         0.02339   -0.00317    0.00127   -0.00319
S2B   5    1.007142    0.120795    0.100490    11.00000    0.02820    0.02054 =
         0.02422   -0.00539    0.00152   -0.00387
O1A   4    0.418702    0.373145    0.911633    11.00000    0.04044    0.02215 =
         0.02285   -0.00517    0.00433   -0.00800
AFIX 147
H1A   2    0.331742    0.358284    0.969395    11.00000   -1.50000
AFIX   0

O1B   4    0.760675    0.125912    0.414033    11.00000    0.04179    0.02275 =
         0.02418   -0.00537    0.00613   -0.00963
AFIX 147
H1B   2    0.722202    0.142320    0.473389    11.00000   -1.50000
AFIX   0
O2B   4    0.980371    0.335479    0.399534    11.00000    0.04172    0.02562 =
         0.02748   -0.00826    0.00278   -0.00821

O2A   4    0.246302    0.160758    0.894205    11.00000    0.04093    0.02632 =
         0.02685   -0.00484    0.00526   -0.01082
N3B   3    0.901247    0.100619    0.217669    11.00000    0.02621    0.02342 =
         0.02476   -0.00590    0.00135   -0.00232
N1A   3    0.648307    0.222646    0.599832    11.00000    0.02671    0.02024 =
         0.02665   -0.00261    0.00014   -0.00113
N3A   3    0.635222    0.403394    0.717023    11.00000    0.02607    0.02071 =
         0.02594   -0.00395    0.00050   -0.00252
N1B   3    1.134741    0.279885    0.096236    11.00000    0.02709    0.02057 =
         0.02765   -0.00545    0.00085   -0.00166
C4A   1    0.515052    0.283805    0.756041    11.00000    0.02329    0.02025 =
         0.02615   -0.00341   -0.00046    0.00080
C5A   1    0.522349    0.179893    0.688921    11.00000    0.02427    0.02181 =
         0.02584   -0.00364    0.00002    0.00016
AFIX  43
H5A   2    0.445060    0.089182    0.706036    11.00000   -1.20000
AFIX   0

C4B   1    0.965685    0.216715    0.256449    11.00000    0.02132    0.02113 =
         0.02681   -0.00652   -0.00092    0.00008
C6B   1    0.904457    0.232940    0.364159    11.00000    0.02504    0.02229 =
         0.02576   -0.00501    0.00126    0.00066
C5B   1    1.098520    0.319985    0.186727    11.00000    0.02532    0.02372 =
         0.02513   -0.00546    0.00024    0.00011
AFIX  43
H5B   2    1.155594    0.408644    0.203145    11.00000   -1.20000
AFIX   0

C6A   1    0.380846    0.265328    0.861232    11.00000    0.02446    0.02211 =
         0.02510   -0.00341    0.00154   -0.00017
HKLF 4




REM  1S.res in P-1
REM wR2 = 0.1351, GooF = S = 1.094, Restrained GooF = 1.094 for all data
REM R1 = 0.0455 for 1889 Fo > 4sig(Fo) and 0.0459 for all 1932 data
REM 147 parameters refined using 0 restraints

END

WGHT      0.0960      0.2392

REM Highest difference peak  0.871,  deepest hole -0.529,  1-sigma level  0.097
Q1    1   0.9490  0.0994  0.1601  11.00000  0.05    0.87
Q2    1   0.6896  0.3785  0.6645  11.00000  0.05    0.82
Q3    1   0.8019  0.4169  0.5417  11.00000  0.05    0.63
Q4    1   0.9451  0.2229  0.3057  11.00000  0.05    0.46
;
_shelx_res_checksum              46908
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2S
_database_code_depnum_ccdc_archive 'CCDC 2332629'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N2 O2 S'
_chemical_formula_sum            'C7 H4 N2 O2 S'
_chemical_formula_weight         180.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   3.70347(15)
_cell_length_b                   6.3835(3)
_cell_length_c                   29.2533(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.866(4)
_cell_angle_gamma                90
_cell_volume                     690.72(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2107
_cell_measurement_theta_min      3.2400
_cell_measurement_theta_max      27.9650

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.416
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86511
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_reflns_number            5655
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.267
_diffrn_reflns_theta_max         28.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1485
_reflns_number_gt                1279
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)'
_computing_cell_refinement       
'CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)'
_computing_data_reduction        
'CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0222P)²+0.7084P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1485
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S2 S 0.57962(14) 0.08831(9) 0.70583(2) 0.01461(15) Uani 1 1 d . . . . .
O1 O 0.2720(4) 0.2437(2) 0.51051(5) 0.0215(4) Uani 1 1 d . . . . .
H1 H 0.324004 0.157856 0.490089 0.032 Uiso 1 1 calc R U . . .
O2 O 0.5640(4) 0.0107(2) 0.55558(5) 0.0190(4) Uani 1 1 d . . . . .
N1 N 0.3996(5) 0.3144(3) 0.71410(6) 0.0147(4) Uani 1 1 d . . . . .
N3 N 0.5568(4) 0.0738(3) 0.65076(6) 0.0124(4) Uani 1 1 d . . . . .
C4 C 0.3124(5) 0.3125(3) 0.58932(7) 0.0111(4) Uani 1 1 d . . . . .
C5 C 0.1501(5) 0.5042(3) 0.58198(7) 0.0132(4) Uani 1 1 d . . . . .
H5 H 0.091922 0.546845 0.551383 0.016 Uiso 1 1 calc R U . . .
C6 C 0.0660(5) 0.6408(3) 0.61814(7) 0.0136(4) Uani 1 1 d . . . . .
H6 H -0.044555 0.772091 0.611240 0.016 Uiso 1 1 calc R U . . .
C7 C 0.1412(5) 0.5868(3) 0.66246(7) 0.0138(4) Uani 1 1 d . . . . .
H7 H 0.082906 0.678378 0.686603 0.017 Uiso 1 1 calc R U . . .
C8 C 0.3087(5) 0.3906(3) 0.67201(7) 0.0123(4) Uani 1 1 d . . . . .
C9 C 0.3973(5) 0.2522(3) 0.63573(7) 0.0108(4) Uani 1 1 d . . . . .
C10 C 0.3946(5) 0.1742(3) 0.55061(7) 0.0134(4) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S2 0.0176(3) 0.0162(3) 0.0100(2) 0.0020(2) 0.00037(19) 0.0010(2)
O1 0.0358(9) 0.0205(9) 0.0080(7) -0.0022(6) -0.0004(7) 0.0133(7)
O2 0.0299(9) 0.0160(9) 0.0111(7) -0.0016(6) 0.0006(6) 0.0091(7)
N1 0.0166(9) 0.0165(10) 0.0110(9) -0.0014(7) 0.0014(7) -0.0009(7)
N3 0.0151(8) 0.0123(9) 0.0099(8) 0.0011(7) 0.0014(7) -0.0007(7)
C4 0.0119(9) 0.0118(11) 0.0096(9) -0.0003(8) 0.0018(8) -0.0009(8)
C5 0.0146(10) 0.0141(11) 0.0110(10) 0.0019(8) 0.0003(8) -0.0001(8)
C6 0.0144(10) 0.0081(11) 0.0186(11) 0.0007(8) 0.0020(8) -0.0001(8)
C7 0.0155(10) 0.0110(11) 0.0151(10) -0.0047(9) 0.0041(8) -0.0010(8)
C8 0.0121(9) 0.0137(11) 0.0114(10) -0.0015(8) 0.0024(8) -0.0035(8)
C9 0.0114(9) 0.0092(11) 0.0119(10) -0.0008(8) 0.0013(8) -0.0027(8)
C10 0.0148(10) 0.0142(11) 0.0114(10) 0.0002(8) 0.0014(8) 0.0003(9)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S2 N3 1.6117(17) . ?
S2 N1 1.6135(19) . ?
O1 C10 1.314(2) . ?
O1 H1 0.8400 . ?
O2 C10 1.223(3) . ?
N1 C8 1.351(3) . ?
N3 C9 1.347(3) . ?
C4 C5 1.376(3) . ?
C4 C9 1.431(3) . ?
C4 C10 1.479(3) . ?
C5 C6 1.417(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.357(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.419(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.431(3) . ?

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
N3 S2 N1 101.54(9) . . ?
C10 O1 H1 109.5 . . ?
C8 N1 S2 105.74(14) . . ?
C9 N3 S2 106.13(14) . . ?
C5 C4 C9 117.43(18) . . ?
C5 C4 C10 121.08(18) . . ?
C9 C4 C10 121.48(18) . . ?
C4 C5 C6 122.79(19) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C7 C6 C5 120.95(19) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 118.63(19) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
N1 C8 C7 125.70(19) . . ?
N1 C8 C9 113.45(18) . . ?
C7 C8 C9 120.85(19) . . ?
N3 C9 C4 127.51(18) . . ?
N3 C9 C8 113.14(18) . . ?
C4 C9 C8 119.35(19) . . ?
O2 C10 O1 123.16(19) . . ?
O2 C10 C4 122.82(19) . . ?
O1 C10 C4 114.01(18) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 S2 N1 C8 0.28(15) . . . . ?
N1 S2 N3 C9 -0.57(15) . . . . ?
C9 C4 C5 C6 0.0(3) . . . . ?
C10 C4 C5 C6 179.81(19) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
S2 N1 C8 C7 180.00(17) . . . . ?
S2 N1 C8 C9 0.1(2) . . . . ?
C6 C7 C8 N1 -179.84(19) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
S2 N3 C9 C4 -179.21(17) . . . . ?
S2 N3 C9 C8 0.7(2) . . . . ?
C5 C4 C9 N3 -179.61(19) . . . . ?
C10 C4 C9 N3 0.5(3) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C10 C4 C9 C8 -179.33(18) . . . . ?
N1 C8 C9 N3 -0.5(3) . . . . ?
C7 C8 C9 N3 179.57(18) . . . . ?
N1 C8 C9 C4 179.37(17) . . . . ?
C7 C8 C9 C4 -0.5(3) . . . . ?
C5 C4 C10 O2 174.0(2) . . . . ?
C9 C4 C10 O2 -6.1(3) . . . . ?
C5 C4 C10 O1 -5.5(3) . . . . ?
C9 C4 C10 O1 174.38(19) . . . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.067

_shelx_res_file                  
;
TITL s-4-cooh_1_a.res in P2(1)/n
    2S.res
    created by SHELXL-2019/3 at 12:19:01 on 01-Feb-2024
REM Old TITL S-4-COOH_1 in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.092, Rweak 0.282, Alpha 0.030
REM <I/s> 0.928 for 130 systematic absences, Orientation as input
REM Formula found by SHELXT: C7 N2 O2 Cl
CELL 0.71073 3.703465 6.383544 29.253265 90 92.8657 90
ZERR 4 0.000146 0.000284 0.001058 0 0.0035 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 28 16 8 8 4

L.S. 10
PLAN  2
SIZE 0.02 0.04 0.3
TEMP -173.1(10)
CONF
BOND $H
list 4
MORE -1
fmap 2 53
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\S-4-COOH_2.hkl">
REM </olex2.extras>

WGHT    0.022200    0.708400
FVAR       3.93870
S2    5    0.579621    0.088311    0.705829    11.00000    0.01764    0.01616 =
         0.01001    0.00199    0.00037    0.00097
O1    4    0.272038    0.243708    0.510506    11.00000    0.03575    0.02052 =
         0.00802   -0.00216   -0.00045    0.01330
AFIX 147
H1    2    0.324004    0.157856    0.490089    11.00000   -1.50000
AFIX   0
O2    4    0.563951    0.010664    0.555585    11.00000    0.02985    0.01597 =
         0.01115   -0.00157    0.00060    0.00910
N1    3    0.399552    0.314450    0.714101    11.00000    0.01656    0.01647 =
         0.01102   -0.00144    0.00140   -0.00089
N3    3    0.556790    0.073781    0.650755    11.00000    0.01508    0.01228 =
         0.00990    0.00107    0.00138   -0.00073
C4    1    0.312406    0.312465    0.589322    11.00000    0.01190    0.01185 =
         0.00963   -0.00031    0.00175   -0.00092
C5    1    0.150109    0.504196    0.581982    11.00000    0.01457    0.01411 =
         0.01098    0.00185    0.00035   -0.00013
AFIX  43
H5    2    0.091922    0.546845    0.551383    11.00000   -1.20000
AFIX   0
C6    1    0.066025    0.640806    0.618136    11.00000    0.01436    0.00806 =
         0.01855    0.00071    0.00204   -0.00007
AFIX  43
H6    2   -0.044555    0.772091    0.611240    11.00000   -1.20000
AFIX   0
C7    1    0.141208    0.586765    0.662464    11.00000    0.01551    0.01096 =
         0.01512   -0.00467    0.00408   -0.00097
AFIX  43
H7    2    0.082906    0.678378    0.686603    11.00000   -1.20000
AFIX   0
C8    1    0.308696    0.390597    0.672011    11.00000    0.01207    0.01370 =
         0.01142   -0.00150    0.00240   -0.00351
C9    1    0.397266    0.252232    0.635731    11.00000    0.01141    0.00919 =
         0.01192   -0.00080    0.00125   -0.00274
C10   1    0.394642    0.174212    0.550605    11.00000    0.01480    0.01416 =
         0.01136    0.00024    0.00139    0.00026
HKLF 4




REM  s-4-cooh_1_a.res in P2(1)/n
REM wR2 = 0.0806, GooF = S = 1.089, Restrained GooF = 1.089 for all data
REM R1 = 0.0404 for 1279 Fo > 4sig(Fo) and 0.0508 for all 1485 data
REM 110 parameters refined using 0 restraints

END

WGHT      0.0222      0.7057

REM Highest difference peak  0.355,  deepest hole -0.286,  1-sigma level  0.067
Q1    1   0.1993  0.6253  0.6413  11.00000  0.05    0.35
Q2    1   0.8194  0.0627  0.7188  11.00000  0.05    0.31
;
_shelx_res_checksum              63138
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4S
_database_code_depnum_ccdc_archive 'CCDC 2332631'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 N2 O2 S'
_chemical_formula_sum            'C8 H6 N2 O2 S'
_chemical_formula_weight         194.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   3.92200(10)
_cell_length_b                   17.4283(4)
_cell_length_c                   11.8780(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.753(2)
_cell_angle_gamma                90
_cell_volume                     811.53(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4744
_cell_measurement_theta_min      3.6840
_cell_measurement_theta_max      76.0790

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.276
_shelx_estimated_absorpt_T_min   0.266
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.56a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5384
_diffrn_reflns_number            7413
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.506
_diffrn_reflns_theta_max         76.337
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1676
_reflns_number_gt                1487
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro 1.171.42.56a (Rigaku Oxford Diffraction, 2022)'
_computing_cell_refinement       
'CrysAlisPro 1.171.42.56a (Rigaku Oxford Diffraction, 2022)'
_computing_data_reduction        
'CrysAlisPro 1.171.42.56a (Rigaku Oxford Diffraction, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+0.2335P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1676
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S2 S 0.78599(10) 0.58202(2) 0.42095(3) 0.02472(15) Uani 1 1 d . . . . .
O1 O 0.7454(3) 0.50731(7) 0.77264(9) 0.0279(3) Uani 1 1 d . . . . .
O2 O 0.6447(4) 0.59118(7) 0.90995(9) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.5832(4) 0.66246(8) 0.41694(11) 0.0261(3) Uani 1 1 d . . . . .
N3 N 0.7855(3) 0.56294(8) 0.55390(11) 0.0222(3) Uani 1 1 d . . . . .
C4 C 0.5457(4) 0.63013(8) 0.71986(12) 0.0202(3) Uani 1 1 d . . . . .
C5 C 0.3726(4) 0.69494(9) 0.75044(13) 0.0233(3) Uani 1 1 d . . . . .
H5 H 0.325130 0.702236 0.827659 0.028 Uiso 1 1 calc R U . . .
C6 C 0.2612(4) 0.75161(9) 0.67143(14) 0.0262(3) Uani 1 1 d . . . . .
H6 H 0.141396 0.795299 0.697167 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3226(4) 0.74459(9) 0.55943(14) 0.0261(3) Uani 1 1 d . . . . .
H7 H 0.248438 0.782654 0.506930 0.031 Uiso 1 1 calc R U . . .
C8 C 0.5012(4) 0.67846(9) 0.52414(12) 0.0225(3) Uani 1 1 d . . . . .
C9 C 0.6151(4) 0.62060(8) 0.60274(12) 0.0196(3) Uani 1 1 d . . . . .
C10 C 0.6506(4) 0.57545(9) 0.81101(13) 0.0216(3) Uani 1 1 d . . . . .
C11 C 0.8544(5) 0.45207(10) 0.85759(14) 0.0317(4) Uani 1 1 d . . . . .
H11A H 0.903238 0.402900 0.821449 0.048 Uiso 1 1 calc R U . . .
H11B H 0.672944 0.445078 0.911565 0.048 Uiso 1 1 calc R U . . .
H11C H 1.060753 0.470899 0.897170 0.048 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S2 0.0305(2) 0.0262(2) 0.0177(2) -0.00043(13) 0.00600(15) -0.00310(15)
O1 0.0416(7) 0.0223(6) 0.0200(5) 0.0022(4) 0.0047(5) 0.0075(5)
O2 0.0560(8) 0.0287(7) 0.0182(6) -0.0007(4) 0.0040(5) 0.0051(6)
N1 0.0302(7) 0.0260(7) 0.0223(6) 0.0033(5) 0.0037(5) -0.0048(5)
N3 0.0269(6) 0.0215(6) 0.0184(6) -0.0016(5) 0.0050(5) -0.0028(5)
C4 0.0215(7) 0.0202(7) 0.0192(7) -0.0009(5) 0.0029(5) -0.0027(5)
C5 0.0245(7) 0.0223(7) 0.0232(7) -0.0020(6) 0.0033(6) -0.0022(6)
C6 0.0258(8) 0.0207(8) 0.0319(8) -0.0009(6) 0.0013(6) 0.0006(6)
C7 0.0289(8) 0.0207(7) 0.0284(8) 0.0038(6) -0.0023(6) -0.0013(6)
C8 0.0240(7) 0.0215(7) 0.0220(7) 0.0023(6) 0.0014(6) -0.0045(6)
C9 0.0202(7) 0.0183(7) 0.0205(7) -0.0001(5) 0.0026(5) -0.0037(5)
C10 0.0240(7) 0.0203(7) 0.0208(7) -0.0004(5) 0.0049(6) -0.0011(5)
C11 0.0405(10) 0.0291(9) 0.0260(8) 0.0088(7) 0.0071(7) 0.0109(7)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S2 N1 1.6118(14) . ?
S2 N3 1.6139(13) . ?
O1 C10 1.3292(19) . ?
O1 C11 1.4495(18) . ?
O2 C10 1.2077(19) . ?
N1 C8 1.352(2) . ?
N3 C9 1.348(2) . ?
C4 C5 1.373(2) . ?
C4 C9 1.435(2) . ?
C4 C10 1.491(2) . ?
C5 C6 1.422(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.365(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.419(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.436(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
N1 S2 N3 101.12(7) . . ?
C10 O1 C11 115.75(12) . . ?
C8 N1 S2 106.43(11) . . ?
C9 N3 S2 106.43(11) . . ?
C5 C4 C9 117.50(14) . . ?
C5 C4 C10 117.49(13) . . ?
C9 C4 C10 125.01(13) . . ?
C4 C5 C6 122.78(15) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C7 C6 C5 121.41(15) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 117.67(15) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
N1 C8 C7 125.42(15) . . ?
N1 C8 C9 112.92(14) . . ?
C7 C8 C9 121.66(14) . . ?
N3 C9 C4 127.92(14) . . ?
N3 C9 C8 113.09(13) . . ?
C4 C9 C8 118.97(14) . . ?
O2 C10 O1 123.39(15) . . ?
O2 C10 C4 123.27(14) . . ?
O1 C10 C4 113.33(13) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 S2 N1 C8 -0.29(12) . . . . ?
N1 S2 N3 C9 0.90(12) . . . . ?
C9 C4 C5 C6 0.2(2) . . . . ?
C10 C4 C5 C6 179.55(14) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
S2 N1 C8 C7 179.50(13) . . . . ?
S2 N1 C8 C9 -0.40(16) . . . . ?
C6 C7 C8 N1 -179.99(15) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
S2 N3 C9 C4 -179.95(13) . . . . ?
S2 N3 C9 C8 -1.22(16) . . . . ?
C5 C4 C9 N3 178.56(15) . . . . ?
C10 C4 C9 N3 -0.7(2) . . . . ?
C5 C4 C9 C8 -0.1(2) . . . . ?
C10 C4 C9 C8 -179.39(14) . . . . ?
N1 C8 C9 N3 1.11(19) . . . . ?
C7 C8 C9 N3 -178.79(14) . . . . ?
N1 C8 C9 C4 179.96(13) . . . . ?
C7 C8 C9 C4 0.1(2) . . . . ?
C11 O1 C10 O2 -1.9(2) . . . . ?
C11 O1 C10 C4 179.23(13) . . . . ?
C5 C4 C10 O2 -13.3(2) . . . . ?
C9 C4 C10 O2 166.03(16) . . . . ?
C5 C4 C10 O1 165.61(14) . . . . ?
C9 C4 C10 O1 -15.1(2) . . . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.055

_shelx_res_file                  
;
TITL s-4-coome_auto_a.res in P2(1)/n
    4S.res
    created by SHELXL-2019/3 at 14:57:11 on 05-Feb-2024
REM Old TITL S-4-COOMe_auto in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.099, Rweak 0.117, Alpha 0.025
REM <I/s> 0.499 for 67 systematic absences, Orientation as input
REM Formula found by SHELXT: C8 N2 O2 Cl
CELL 1.54184 3.922 17.4283 11.878 90 91.753 90
ZERR 4 0.0001 0.0004 0.0003 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 32 24 8 8 4

L.S. 4 0 0
PLAN  2
SIZE 0.55 0.04 0.03
TEMP -143.15
CONF
list 4
MORE -1
BOND $H
fmap 2 53
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\S-4-COOMe_auto.hkl">
REM </olex2.extras>

WGHT    0.051900    0.233500
FVAR       0.96367
S2    5    0.785991    0.582021    0.420952    11.00000    0.03055    0.02617 =
         0.01775   -0.00043    0.00600   -0.00310
O1    4    0.745372    0.507308    0.772642    11.00000    0.04163    0.02233 =
         0.01997    0.00223    0.00468    0.00752
O2    4    0.644700    0.591178    0.909949    11.00000    0.05601    0.02874 =
         0.01824   -0.00074    0.00400    0.00512
N1    3    0.583198    0.662463    0.416937    11.00000    0.03020    0.02604 =
         0.02226    0.00326    0.00367   -0.00483
N3    3    0.785535    0.562935    0.553903    11.00000    0.02693    0.02152 =
         0.01844   -0.00158    0.00503   -0.00278
C4    1    0.545724    0.630127    0.719855    11.00000    0.02151    0.02016 =
         0.01915   -0.00090    0.00291   -0.00273
C5    1    0.372563    0.694936    0.750440    11.00000    0.02450    0.02226 =
         0.02320   -0.00202    0.00331   -0.00223
AFIX  43
H5    2    0.325130    0.702236    0.827659    11.00000   -1.20000
AFIX   0
C6    1    0.261162    0.751614    0.671435    11.00000    0.02582    0.02073 =
         0.03194   -0.00095    0.00132    0.00058
AFIX  43
H6    2    0.141396    0.795299    0.697167    11.00000   -1.20000
AFIX   0
C7    1    0.322638    0.744590    0.559427    11.00000    0.02893    0.02068 =
         0.02845    0.00376   -0.00229   -0.00132
AFIX  43
H7    2    0.248438    0.782654    0.506930    11.00000   -1.20000
AFIX   0
C8    1    0.501223    0.678457    0.524138    11.00000    0.02405    0.02153 =
         0.02204    0.00233    0.00139   -0.00448
C9    1    0.615133    0.620600    0.602743    11.00000    0.02020    0.01830 =
         0.02053   -0.00008    0.00258   -0.00367
C10   1    0.650612    0.575453    0.811006    11.00000    0.02399    0.02028 =
         0.02084   -0.00035    0.00485   -0.00114
C11   1    0.854406    0.452073    0.857585    11.00000    0.04054    0.02907 =
         0.02597    0.00879    0.00709    0.01090
AFIX 137
H11A  2    0.903238    0.402900    0.821449    11.00000   -1.50000
H11B  2    0.672944    0.445078    0.911565    11.00000   -1.50000
H11C  2    1.060753    0.470899    0.897170    11.00000   -1.50000
AFIX   0
HKLF 4




REM  s-4-coome_auto_a.res in P2(1)/n
REM wR2 = 0.0887, GooF = S = 1.051, Restrained GooF = 1.051 for all data
REM R1 = 0.0317 for 1487 Fo > 4sig(Fo) and 0.0363 for all 1676 data
REM 119 parameters refined using 0 restraints

END

WGHT      0.0519      0.2335

REM Highest difference peak  0.242,  deepest hole -0.379,  1-sigma level  0.055
Q1    1   0.5826  0.6228  0.6597  11.00000  0.05    0.24
Q2    1   0.5607  0.6582  0.5653  11.00000  0.05    0.23
;
_shelx_res_checksum              71689
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5S
_database_code_depnum_ccdc_archive 'CCDC 2332632'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 N2 O2 S'
_chemical_formula_sum            'C8 H6 N2 O2 S'
_chemical_formula_weight         194.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.3375(6)
_cell_length_b                   3.81288(10)
_cell_length_c                   22.5207(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.866(3)
_cell_angle_gamma                90
_cell_volume                     1642.43(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    6452
_cell_measurement_theta_min      2.0320
_cell_measurement_theta_max      75.6740

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.238
_shelx_estimated_absorpt_T_min   0.294
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75853
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5384
_diffrn_reflns_number            13639
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.310
_diffrn_reflns_theta_max         76.100
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3379
_reflns_number_gt                2983
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)'
_computing_cell_refinement       
'CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)'
_computing_data_reduction        
'CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²+0.5966P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3379
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S2A S 0.91966(2) 0.75089(13) 0.45065(2) 0.03616(15) Uani 1 1 d . . . . .
O1A O 0.59632(7) 0.6854(4) 0.43613(6) 0.0380(3) Uani 1 1 d . . . . .
O2A O 0.61645(8) 0.4128(4) 0.52914(7) 0.0458(4) Uani 1 1 d . . . . .
N1A N 0.92287(9) 0.5618(5) 0.51621(8) 0.0373(4) Uani 1 1 d . . . . .
N3A N 0.83724(8) 0.8299(4) 0.41974(7) 0.0331(3) Uani 1 1 d . . . . .
C4A C 0.73443(10) 0.7099(5) 0.45088(8) 0.0294(4) Uani 1 1 d . . . . .
H4A H 0.701792 0.813048 0.414285 0.035 Uiso 1 1 calc R U . . .
C5A C 0.71336(10) 0.5604(5) 0.49679(8) 0.0316(4) Uani 1 1 d . . . . .
C6A C 0.76228(11) 0.4126(5) 0.55259(8) 0.0331(4) Uani 1 1 d . . . . .
H6A H 0.745389 0.314158 0.583401 0.040 Uiso 1 1 calc R U . . .
C7A C 0.83252(11) 0.4078(5) 0.56326(9) 0.0356(4) Uani 1 1 d . . . . .
H7A H 0.864380 0.311374 0.600978 0.043 Uiso 1 1 calc R U . . .
C8A C 0.85639(10) 0.5525(5) 0.51581(8) 0.0326(4) Uani 1 1 d . . . . .
C9A C 0.80705(10) 0.7042(5) 0.46031(8) 0.0298(4) Uani 1 1 d . . . . .
C10A C 0.63788(10) 0.5427(5) 0.49039(9) 0.0333(4) Uani 1 1 d . . . . .
C11A C 0.52258(10) 0.6808(6) 0.42691(10) 0.0413(5) Uani 1 1 d . . . . .
H11A H 0.496736 0.796514 0.386922 0.062 Uiso 1 1 calc R U . . .
H11B H 0.514232 0.805171 0.461766 0.062 Uiso 1 1 calc R U . . .
H11C H 0.506666 0.437461 0.425790 0.062 Uiso 1 1 calc R U . . .
S2B S 0.57878(2) 0.42086(14) 0.28390(2) 0.03617(15) Uani 1 1 d . . . . .
O1B O 0.90427(7) 0.2496(4) 0.31194(6) 0.0364(3) Uani 1 1 d . . . . .
O2B O 0.89346(7) 0.4564(5) 0.21557(7) 0.0466(4) Uani 1 1 d . . . . .
N1B N 0.58355(8) 0.5901(5) 0.21920(8) 0.0358(4) Uani 1 1 d . . . . .
N3B N 0.65809(8) 0.2938(4) 0.31857(7) 0.0309(3) Uani 1 1 d . . . . .
C4B C 0.76599(9) 0.3286(5) 0.29222(8) 0.0261(3) Uani 1 1 d . . . . .
H4B H 0.794656 0.218288 0.329967 0.031 Uiso 1 1 calc R U . . .
C5B C 0.79270(9) 0.4406(5) 0.24720(8) 0.0274(4) Uani 1 1 d . . . . .
C6B C 0.74990(10) 0.6068(5) 0.19019(8) 0.0303(4) Uani 1 1 d . . . . .
H6B H 0.770844 0.680545 0.160463 0.036 Uiso 1 1 calc R U . . .
C7B C 0.68036(10) 0.6631(5) 0.17702(8) 0.0330(4) Uani 1 1 d . . . . .
H7B H 0.652589 0.771838 0.138762 0.040 Uiso 1 1 calc R U . . .
C8B C 0.65081(9) 0.5523(5) 0.22304(8) 0.0299(4) Uani 1 1 d . . . . .
C9B C 0.69349(9) 0.3849(5) 0.27987(8) 0.0271(4) Uani 1 1 d . . . . .
C10B C 0.86789(9) 0.3871(5) 0.25520(9) 0.0312(4) Uani 1 1 d . . . . .
C11B C 0.97707(9) 0.1788(6) 0.32193(10) 0.0391(4) Uani 1 1 d . . . . .
H11D H 0.980597 0.013742 0.289788 0.059 Uiso 1 1 calc R U . . .
H11E H 0.999129 0.076518 0.363951 0.059 Uiso 1 1 calc R U . . .
H11F H 1.000829 0.398046 0.318820 0.059 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S2A 0.0325(2) 0.0368(3) 0.0362(3) 0.00147(19) 0.00782(18) 0.00027(18)
O1A 0.0344(7) 0.0470(8) 0.0327(7) 0.0043(6) 0.0114(5) 0.0038(6)
O2A 0.0471(8) 0.0541(10) 0.0382(7) 0.0072(7) 0.0171(6) -0.0052(7)
N1A 0.0376(8) 0.0357(9) 0.0328(8) 0.0007(7) 0.0046(7) 0.0025(7)
N3A 0.0326(7) 0.0329(8) 0.0320(8) 0.0010(7) 0.0085(6) 0.0006(7)
C4A 0.0362(9) 0.0254(9) 0.0239(8) -0.0002(7) 0.0065(7) -0.0006(7)
C5A 0.0394(9) 0.0270(9) 0.0270(8) -0.0032(7) 0.0096(7) -0.0013(7)
C6A 0.0464(10) 0.0270(9) 0.0253(8) 0.0000(7) 0.0115(7) -0.0004(8)
C7A 0.0468(10) 0.0294(10) 0.0250(8) 0.0011(7) 0.0048(7) 0.0026(8)
C8A 0.0383(9) 0.0263(9) 0.0288(9) -0.0040(7) 0.0058(7) 0.0009(7)
C9A 0.0365(9) 0.0248(9) 0.0259(8) -0.0011(7) 0.0078(7) 0.0001(7)
C10A 0.0411(10) 0.0304(10) 0.0287(8) -0.0028(7) 0.0123(7) -0.0022(8)
C11A 0.0331(9) 0.0476(12) 0.0438(11) 0.0041(10) 0.0140(8) 0.0034(9)
S2B 0.0255(2) 0.0424(3) 0.0402(3) -0.0043(2) 0.01069(17) 0.00002(18)
O1B 0.0260(6) 0.0514(9) 0.0337(7) -0.0006(6) 0.0126(5) 0.0042(6)
O2B 0.0392(7) 0.0673(11) 0.0397(8) 0.0022(7) 0.0218(6) -0.0082(7)
N1B 0.0319(8) 0.0364(9) 0.0341(8) -0.0030(7) 0.0048(6) 0.0035(7)
N3B 0.0278(7) 0.0326(8) 0.0337(8) -0.0021(6) 0.0122(6) -0.0019(6)
C4B 0.0281(8) 0.0253(8) 0.0240(8) -0.0020(7) 0.0077(6) 0.0000(7)
C5B 0.0301(8) 0.0256(9) 0.0272(8) -0.0039(7) 0.0109(7) -0.0033(7)
C6B 0.0392(9) 0.0268(9) 0.0259(8) -0.0014(7) 0.0122(7) -0.0035(7)
C7B 0.0403(9) 0.0291(9) 0.0258(8) -0.0002(7) 0.0062(7) 0.0021(8)
C8B 0.0309(8) 0.0265(9) 0.0286(8) -0.0045(7) 0.0053(7) 0.0003(7)
C9B 0.0281(8) 0.0263(9) 0.0267(8) -0.0036(7) 0.0090(6) -0.0015(7)
C10B 0.0313(9) 0.0327(10) 0.0321(9) -0.0055(7) 0.0142(7) -0.0053(7)
C11B 0.0264(8) 0.0485(12) 0.0460(11) -0.0022(10) 0.0172(8) 0.0035(8)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S2A N3A 1.6100(16) . ?
S2A N1A 1.6243(17) . ?
O1A C10A 1.342(2) . ?
O1A C11A 1.443(2) . ?
O2A C10A 1.206(2) . ?
N1A C8A 1.350(3) . ?
N3A C9A 1.350(2) . ?
C4A C5A 1.371(3) . ?
C4A C9A 1.419(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.427(3) . ?
C5A C10A 1.494(3) . ?
C6A C7A 1.366(3) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.426(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.432(2) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
S2B N3B 1.6095(16) . ?
S2B N1B 1.6264(17) . ?
O1B C10B 1.346(2) . ?
O1B C11B 1.445(2) . ?
O2B C10B 1.205(2) . ?
N1B C8B 1.349(2) . ?
N3B C9B 1.351(2) . ?
C4B C5B 1.371(2) . ?
C4B C9B 1.421(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.431(2) . ?
C5B C10B 1.492(2) . ?
C6B C7B 1.360(3) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.427(3) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.429(2) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?

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
N3A S2A N1A 100.98(9) . . ?
C10A O1A C11A 115.36(15) . . ?
C8A N1A S2A 105.95(13) . . ?
C9A N3A S2A 106.68(13) . . ?
C5A C4A C9A 117.19(16) . . ?
C5A C4A H4A 121.4 . . ?
C9A C4A H4A 121.4 . . ?
C4A C5A C6A 121.69(18) . . ?
C4A C5A C10A 121.37(17) . . ?
C6A C5A C10A 116.94(17) . . ?
C7A C6A C5A 122.32(17) . . ?
C7A C6A H6A 118.8 . . ?
C5A C6A H6A 118.8 . . ?
C6A C7A C8A 117.70(17) . . ?
C6A C7A H7A 121.2 . . ?
C8A C7A H7A 121.2 . . ?
N1A C8A C7A 126.90(17) . . ?
N1A C8A C9A 113.48(17) . . ?
C7A C8A C9A 119.62(18) . . ?
N3A C9A C4A 125.65(16) . . ?
N3A C9A C8A 112.90(17) . . ?
C4A C9A C8A 121.44(17) . . ?
O2A C10A O1A 123.68(18) . . ?
O2A C10A C5A 124.11(18) . . ?
O1A C10A C5A 112.21(16) . . ?
O1A C11A H11A 109.5 . . ?
O1A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
O1A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
N3B S2B N1B 101.47(8) . . ?
C10B O1B C11B 115.09(14) . . ?
C8B N1B S2B 105.55(13) . . ?
C9B N3B S2B 105.99(13) . . ?
C5B C4B C9B 116.97(16) . . ?
C5B C4B H4B 121.5 . . ?
C9B C4B H4B 121.5 . . ?
C4B C5B C6B 121.90(16) . . ?
C4B C5B C10B 121.03(16) . . ?
C6B C5B C10B 117.06(15) . . ?
C7B C6B C5B 122.41(16) . . ?
C7B C6B H6B 118.8 . . ?
C5B C6B H6B 118.8 . . ?
C6B C7B C8B 117.27(16) . . ?
C6B C7B H7B 121.4 . . ?
C8B C7B H7B 121.4 . . ?
N1B C8B C7B 126.15(17) . . ?
N1B C8B C9B 113.53(16) . . ?
C7B C8B C9B 120.32(16) . . ?
N3B C9B C4B 125.43(16) . . ?
N3B C9B C8B 113.44(16) . . ?
C4B C9B C8B 121.12(16) . . ?
O2B C10B O1B 123.51(17) . . ?
O2B C10B C5B 124.27(18) . . ?
O1B C10B C5B 112.22(14) . . ?
O1B C11B H11D 109.5 . . ?
O1B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
O1B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3A S2A N1A C8A 0.31(15) . . . . ?
N1A S2A N3A C9A -0.70(15) . . . . ?
C9A C4A C5A C6A 1.5(3) . . . . ?
C9A C4A C5A C10A -178.04(17) . . . . ?
C4A C5A C6A C7A -0.7(3) . . . . ?
C10A C5A C6A C7A 178.88(18) . . . . ?
C5A C6A C7A C8A -0.9(3) . . . . ?
S2A N1A C8A C7A 179.36(17) . . . . ?
S2A N1A C8A C9A 0.2(2) . . . . ?
C6A C7A C8A N1A -177.47(19) . . . . ?
C6A C7A C8A C9A 1.7(3) . . . . ?
S2A N3A C9A C4A -178.18(16) . . . . ?
S2A N3A C9A C8A 0.87(19) . . . . ?
C5A C4A C9A N3A 178.22(18) . . . . ?
C5A C4A C9A C8A -0.8(3) . . . . ?
N1A C8A C9A N3A -0.7(2) . . . . ?
C7A C8A C9A N3A -179.96(17) . . . . ?
N1A C8A C9A C4A 178.39(17) . . . . ?
C7A C8A C9A C4A -0.9(3) . . . . ?
C11A O1A C10A O2A 1.1(3) . . . . ?
C11A O1A C10A C5A -179.45(17) . . . . ?
C4A C5A C10A O2A 179.6(2) . . . . ?
C6A C5A C10A O2A 0.0(3) . . . . ?
C4A C5A C10A O1A 0.2(3) . . . . ?
C6A C5A C10A O1A -179.38(16) . . . . ?
N3B S2B N1B C8B -0.32(15) . . . . ?
N1B S2B N3B C9B 0.65(14) . . . . ?
C9B C4B C5B C6B 0.0(3) . . . . ?
C9B C4B C5B C10B -178.79(16) . . . . ?
C4B C5B C6B C7B -0.2(3) . . . . ?
C10B C5B C6B C7B 178.62(18) . . . . ?
C5B C6B C7B C8B 0.6(3) . . . . ?
S2B N1B C8B C7B -179.78(16) . . . . ?
S2B N1B C8B C9B -0.10(19) . . . . ?
C6B C7B C8B N1B 178.80(18) . . . . ?
C6B C7B C8B C9B -0.9(3) . . . . ?
S2B N3B C9B C4B 178.82(15) . . . . ?
S2B N3B C9B C8B -0.77(19) . . . . ?
C5B C4B C9B N3B -179.78(17) . . . . ?
C5B C4B C9B C8B -0.2(3) . . . . ?
N1B C8B C9B N3B 0.6(2) . . . . ?
C7B C8B C9B N3B -179.70(17) . . . . ?
N1B C8B C9B C4B -179.01(16) . . . . ?
C7B C8B C9B C4B 0.7(3) . . . . ?
C11B O1B C10B O2B -1.8(3) . . . . ?
C11B O1B C10B C5B 177.80(16) . . . . ?
C4B C5B C10B O2B 174.47(19) . . . . ?
C6B C5B C10B O2B -4.3(3) . . . . ?
C4B C5B C10B O1B -5.1(3) . . . . ?
C6B C5B C10B O1B 176.05(16) . . . . ?

_refine_diff_density_max         0.441
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.055

_shelx_res_file                  
;
TITL s-5-coome_auto_a.res in P2(1)/c
    5S.res
    created by SHELXL-2019/3 at 14:43:43 on 05-Feb-2024
REM Old TITL S-5-COOMe_auto in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.106, Rweak 0.036, Alpha 0.021
REM <I/s> 0.488 for 529 systematic absences, Orientation as input
REM Formula found by SHELXT: C17 N3 O4 Cl2
CELL 1.54184 20.337534 3.812883 22.520661 90 109.8663 90
ZERR 8 0.000559 0.000097 0.000686 0 0.0034 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 64 48 16 16 8

L.S. 4 0 0
PLAN  4
SIZE 0.5 0.05 0.02
TEMP -143.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\5S.hkl">
REM </olex2.extras>

WGHT    0.057600    0.596600
FVAR       3.53989
S2A   5    0.919659    0.750885    0.450652    11.00000    0.03249    0.03680 =
         0.03623    0.00147    0.00782    0.00027
O1A   4    0.596318    0.685409    0.436131    11.00000    0.03439    0.04702 =
         0.03266    0.00430    0.01144    0.00375
O2A   4    0.616453    0.412811    0.529144    11.00000    0.04711    0.05411 =
         0.03819    0.00723    0.01713   -0.00516
N1A   3    0.922873    0.561763    0.516211    11.00000    0.03761    0.03570 =
         0.03276    0.00070    0.00456    0.00254
N3A   3    0.837241    0.829940    0.419741    11.00000    0.03257    0.03294 =
         0.03202    0.00105    0.00852    0.00058
C4A   1    0.734431    0.709930    0.450876    11.00000    0.03620    0.02538 =
         0.02391   -0.00016    0.00651   -0.00058
AFIX  43
H4A   2    0.701792    0.813048    0.414285    11.00000   -1.20000
AFIX   0
C5A   1    0.713361    0.560407    0.496785    11.00000    0.03942    0.02704 =
         0.02700   -0.00320    0.00956   -0.00129
C6A   1    0.762279    0.412634    0.552589    11.00000    0.04645    0.02697 =
         0.02533   -0.00001    0.01153   -0.00038
AFIX  43
H6A   2    0.745389    0.314158    0.583401    11.00000   -1.20000
AFIX   0
C7A   1    0.832521    0.407798    0.563258    11.00000    0.04677    0.02939 =
         0.02497    0.00112    0.00481    0.00256
AFIX  43
H7A   2    0.864380    0.311374    0.600978    11.00000   -1.20000
AFIX   0
C8A   1    0.856385    0.552515    0.515813    11.00000    0.03832    0.02629 =
         0.02882   -0.00398    0.00575    0.00093
C9A   1    0.807046    0.704212    0.460305    11.00000    0.03645    0.02477 =
         0.02594   -0.00110    0.00784    0.00014
C10A  1    0.637876    0.542741    0.490393    11.00000    0.04115    0.03040 =
         0.02868   -0.00282    0.01233   -0.00215
C11A  1    0.522577    0.680767    0.426913    11.00000    0.03313    0.04763 =
         0.04382    0.00412    0.01403    0.00338
AFIX 137
H11A  2    0.496736    0.796514    0.386922    11.00000   -1.50000
H11B  2    0.514232    0.805171    0.461766    11.00000   -1.50000
H11C  2    0.506666    0.437461    0.425790    11.00000   -1.50000
AFIX   0

S2B   5    0.578776    0.420864    0.283901    11.00000    0.02550    0.04244 =
         0.04020   -0.00429    0.01069    0.00002
O1B   4    0.904270    0.249640    0.311938    11.00000    0.02599    0.05145 =
         0.03371   -0.00058    0.01261    0.00416
O2B   4    0.893461    0.456449    0.215566    11.00000    0.03921    0.06727 =
         0.03975    0.00222    0.02183   -0.00825
N1B   3    0.583554    0.590134    0.219203    11.00000    0.03191    0.03636 =
         0.03414   -0.00302    0.00480    0.00355
N3B   3    0.658093    0.293789    0.318569    11.00000    0.02777    0.03261 =
         0.03369   -0.00213    0.01220   -0.00191
C4B   1    0.765987    0.328583    0.292223    11.00000    0.02814    0.02535 =
         0.02405   -0.00196    0.00770    0.00004
AFIX  43
H4B   2    0.794656    0.218288    0.329967    11.00000   -1.20000
AFIX   0
C5B   1    0.792697    0.440637    0.247200    11.00000    0.03014    0.02564 =
         0.02718   -0.00391    0.01093   -0.00329
C6B   1    0.749904    0.606841    0.190195    11.00000    0.03918    0.02682 =
         0.02588   -0.00141    0.01219   -0.00347
AFIX  43
H6B   2    0.770844    0.680545    0.160463    11.00000   -1.20000
AFIX   0
C7B   1    0.680363    0.663145    0.177024    11.00000    0.04025    0.02906 =
         0.02581   -0.00020    0.00617    0.00208
AFIX  43
H7B   2    0.652589    0.771838    0.138762    11.00000   -1.20000
AFIX   0
C8B   1    0.650805    0.552254    0.223038    11.00000    0.03087    0.02652 =
         0.02860   -0.00452    0.00528    0.00034
C9B   1    0.693488    0.384912    0.279866    11.00000    0.02807    0.02631 =
         0.02670   -0.00365    0.00904   -0.00150
C10B  1    0.867891    0.387138    0.255203    11.00000    0.03129    0.03272 =
         0.03213   -0.00552    0.01417   -0.00533
C11B  1    0.977066    0.178783    0.321928    11.00000    0.02643    0.04850 =
         0.04603   -0.00220    0.01725    0.00352
AFIX 137
H11D  2    0.980597    0.013742    0.289788    11.00000   -1.50000
H11E  2    0.999129    0.076518    0.363951    11.00000   -1.50000
H11F  2    1.000829    0.398046    0.318820    11.00000   -1.50000
AFIX   0
HKLF 4




REM  s-5-coome_auto_a.res in P2(1)/c
REM wR2 = 0.1068, GooF = S = 1.042, Restrained GooF = 1.042 for all data
REM R1 = 0.0388 for 2983 Fo > 4sig(Fo) and 0.0446 for all 3379 data
REM 237 parameters refined using 0 restraints

END

WGHT      0.0577      0.5969

REM Highest difference peak  0.441,  deepest hole -0.333,  1-sigma level  0.055
Q1    1   0.5782  0.2491  0.3031  11.00000  0.05    0.44
Q2    1   0.8530  0.7414  0.4388  11.00000  0.05    0.27
Q3    1   0.9208  0.9352  0.4923  11.00000  0.05    0.25
Q4    1   0.7206  0.5827  0.1815  11.00000  0.05    0.24
;
_shelx_res_checksum              85951
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3s
_database_code_depnum_ccdc_archive 'CCDC 2332630'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;
_audit_creation_date             2024-02-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H4 N2 O2 S'
_chemical_formula_sum            'C7 H4 N2 O2 S'
_chemical_formula_weight         180.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9301(4)
_cell_length_b                   7.3617(4)
_cell_length_c                   8.2491(4)
_cell_angle_alpha                91.500(5)
_cell_angle_beta                 107.919(5)
_cell_angle_gamma                115.929(6)
_cell_volume                     353.71(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    591
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      72.2500
_cell_measurement_theta_min      6.7830
_shelx_estimated_absorpt_T_max   0.836
_shelx_estimated_absorpt_T_min   0.524
_exptl_absorpt_coefficient_mu    3.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2715
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.607
_diffrn_reflns_theta_min         5.739
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  39.00   1.00    2.50    --  -40.98  19.00 -60.00   65
  2  ω   -121.00   0.00   1.00    2.50    --  -40.98 -19.00 120.00  121
  3  ω    -39.00  26.00   1.00    2.50    --   40.98 -19.00  60.00   65
  4  ω      6.00  97.00   1.00    2.50    --   40.98-125.00  60.00   91
  5  ω    -33.00  42.00   1.00    2.50    --   40.98 -37.00 -90.00   75
  6  ω      6.00  97.00   1.00    2.50    --   40.98-125.00-120.00   91
  7  ω     40.00  71.00   1.00   10.00    --  112.00 -61.00   0.00   31
  8  ω     40.00  71.00   1.00   10.00    --  112.00 -61.00-120.00   31
  9  ω     83.00 158.00   1.00   10.00    --  112.00 111.00 120.00   75
 10  ω     40.00  45.00   1.00   10.00    --  112.00-136.00 -22.00    5
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1354239000
_diffrn_orient_matrix_UB_12      -0.0599504000
_diffrn_orient_matrix_UB_13      -0.1967237000
_diffrn_orient_matrix_UB_21      0.2270969000
_diffrn_orient_matrix_UB_22      0.0956964000
_diffrn_orient_matrix_UB_23      -0.0346761000
_diffrn_orient_matrix_UB_31      0.0025696000
_diffrn_orient_matrix_UB_32      -0.2081993000
_diffrn_orient_matrix_UB_33      -0.0021945000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2521
_reflns_number_total             2715
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         2715
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.062
_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)+(0.0598P)²+0.0894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0965
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5865(14)
 0.4135(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
S2 S 0.05812(8) 0.77819(7) 0.07695(6) 0.02795(18) Uani 1 1 d . . . . .
O1 O 0.4046(3) 0.4462(2) 0.77393(18) 0.0316(3) Uani 1 1 d . . . . .
H1 H 0.456(8) 0.380(8) 0.876(7) 0.140(19) Uiso 1 1 d . . . . .
O2 O 0.4778(2) 0.7158(2) 0.95824(17) 0.0293(3) Uani 1 1 d . . . . .
N1 N 0.1101(3) 0.9478(3) 0.2342(2) 0.0270(4) Uani 1 1 d . . . . .
N3 N 0.1219(3) 0.6180(3) 0.1820(2) 0.0262(4) Uani 1 1 d . . . . .
C4 C 0.2662(3) 0.6066(3) 0.4917(2) 0.0221(4) Uani 1 1 d . . . . .
H4 H 0.2733 0.4822 0.4725 0.027 Uiso 1 1 calc R U . . .
C5 C 0.3288(3) 0.7069(3) 0.6565(2) 0.0216(4) Uani 1 1 d . . . . .
C6 C 0.3160(3) 0.8932(3) 0.6867(2) 0.0235(4) Uani 1 1 d . . . . .
H6 H 0.3572 0.9563 0.8026 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2464(3) 0.9819(3) 0.5541(2) 0.0247(4) Uani 1 1 d . . . . .
H7 H 0.2408 1.1065 0.5759 0.030 Uiso 1 1 calc R U . . .
C8 C 0.1821(3) 0.8830(3) 0.3816(2) 0.0221(4) Uani 1 1 d . . . . .
C9 C 0.1905(3) 0.6953(3) 0.3516(2) 0.0223(4) Uani 1 1 d . . . . .
C10 C 0.4098(3) 0.6198(3) 0.8074(2) 0.0225(4) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S2 0.0381(3) 0.0308(3) 0.0203(3) 0.00852(18) 0.01049(19) 0.0204(2)
O1 0.0454(8) 0.0269(7) 0.0220(6) 0.0038(5) 0.0060(6) 0.0206(6)
O2 0.0392(7) 0.0294(7) 0.0185(6) 0.0024(5) 0.0078(5) 0.0170(6)
N1 0.0314(8) 0.0279(8) 0.0251(8) 0.0082(6) 0.0105(6) 0.0163(7)
N3 0.0354(8) 0.0284(8) 0.0183(7) 0.0066(6) 0.0091(6) 0.0181(7)
C4 0.0259(9) 0.0206(8) 0.0202(8) 0.0040(7) 0.0084(7) 0.0110(7)
C5 0.0216(8) 0.0213(9) 0.0196(8) 0.0031(7) 0.0078(6) 0.0079(7)
C6 0.0245(8) 0.0236(9) 0.0200(8) 0.0003(7) 0.0075(7) 0.0098(7)
C7 0.0271(8) 0.0210(9) 0.0263(9) 0.0012(7) 0.0097(7) 0.0115(7)
C8 0.0223(8) 0.0234(9) 0.0217(8) 0.0057(7) 0.0085(6) 0.0110(7)
C9 0.0238(8) 0.0222(9) 0.0197(8) 0.0022(7) 0.0089(7) 0.0091(7)
C10 0.0239(8) 0.0240(9) 0.0179(8) 0.0030(7) 0.0074(6) 0.0097(7)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S2 N1 1.6146(17) . ?
S2 N3 1.6156(16) . ?
O1 H1 1.03(5) . ?
O1 C10 1.283(2) . ?
O2 C10 1.254(2) . ?
N1 C8 1.349(2) . ?
N3 C9 1.349(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(2) . ?
C4 C9 1.415(3) . ?
C5 C6 1.433(3) . ?
C5 C10 1.484(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.358(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.423(2) . ?
C8 C9 1.427(3) . ?

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
N1 S2 N3 101.18(8) . . ?
C10 O1 H1 118(3) . . ?
C8 N1 S2 106.16(13) . . ?
C9 N3 S2 105.98(13) . . ?
C5 C4 H4 121.2 . . ?
C5 C4 C9 117.53(17) . . ?
C9 C4 H4 121.2 . . ?
C4 C5 C6 121.65(17) . . ?
C4 C5 C10 119.41(17) . . ?
C6 C5 C10 118.94(16) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.67(16) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 120.9 . . ?
C6 C7 C8 118.20(17) . . ?
C8 C7 H7 120.9 . . ?
N1 C8 C7 126.77(18) . . ?
N1 C8 C9 113.20(17) . . ?
C7 C8 C9 120.03(17) . . ?
N3 C9 C4 125.62(17) . . ?
N3 C9 C8 113.47(17) . . ?
C4 C9 C8 120.91(16) . . ?
O1 C10 C5 116.78(16) . . ?
O2 C10 O1 123.50(17) . . ?
O2 C10 C5 119.72(17) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 N1 C8 C7 -179.48(15) . . . . ?
S2 N1 C8 C9 0.57(19) . . . . ?
S2 N3 C9 C4 -179.01(15) . . . . ?
S2 N3 C9 C8 0.72(19) . . . . ?
N1 S2 N3 C9 -0.35(14) . . . . ?
N1 C8 C9 N3 -0.9(2) . . . . ?
N1 C8 C9 C4 178.86(16) . . . . ?
N3 S2 N1 C8 -0.14(14) . . . . ?
C4 C5 C6 C7 -1.6(3) . . . . ?
C4 C5 C10 O1 -3.7(2) . . . . ?
C4 C5 C10 O2 176.54(16) . . . . ?
C5 C4 C9 N3 -179.78(17) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C6 C5 C10 O1 175.68(16) . . . . ?
C6 C5 C10 O2 -4.1(3) . . . . ?
C6 C7 C8 N1 -179.62(17) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 N3 179.16(15) . . . . ?
C7 C8 C9 C4 -1.1(3) . . . . ?
C9 C4 C5 C6 0.8(3) . . . . ?
C9 C4 C5 C10 -179.85(15) . . . . ?
C10 C5 C6 C7 179.05(16) . . . . ?

_shelx_res_file                  
;
    3s.res created by SHELXL-2014/7

TITL s-5-cooh_a.res in P-1
REM Old TITL S-5-COOH in P-1
REM SHELXT solution in P-1: R1 0.110, Rweak 0.017, Alpha 0.088
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C7 N2 O2 S
CELL 1.54184 6.930095 7.36167 8.249104 91.5001 107.9185 115.9294
ZERR 2 0.000385 0.000417 0.000422 0.0045 0.0048 0.0055
LATT 1
SFAC C H N O S
UNIT 14 8 4 4 2

L.S. 4 0 0
PLAN  2
SIZE 0.2 0.17 0.05
TEMP -142
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\3S.hkl">
REM </olex2.extras>

WGHT    0.059800    0.089400
BASF   0.41350
FVAR       9.94609
S2    5    0.058124    0.778188    0.076947    11.00000    0.03814    0.03079 =
         0.02027    0.00852    0.01049    0.02038
O1    4    0.404645    0.446159    0.773934    11.00000    0.04538    0.02691 =
         0.02202    0.00377    0.00599    0.02059
H1    2    0.456152    0.380287    0.876196    11.00000    0.14038
O2    4    0.477814    0.715764    0.958244    11.00000    0.03918    0.02936 =
         0.01845    0.00245    0.00776    0.01699
N1    3    0.110085    0.947838    0.234221    11.00000    0.03145    0.02788 =
         0.02514    0.00820    0.01047    0.01627
N3    3    0.121917    0.618015    0.181989    11.00000    0.03538    0.02839 =
         0.01832    0.00663    0.00909    0.01805
C4    1    0.266157    0.606593    0.491738    11.00000    0.02591    0.02058 =
         0.02020    0.00400    0.00838    0.01104
AFIX  43
H4    2    0.273285    0.482236    0.472493    11.00000   -1.20000
AFIX   0
C5    1    0.328828    0.706904    0.656456    11.00000    0.02158    0.02131 =
         0.01958    0.00305    0.00778    0.00785
C6    1    0.315968    0.893217    0.686750    11.00000    0.02453    0.02363 =
         0.02003    0.00028    0.00746    0.00975
AFIX  43
H6    2    0.357169    0.956262    0.802550    11.00000   -1.20000
AFIX   0
C7    1    0.246398    0.981878    0.554146    11.00000    0.02708    0.02100 =
         0.02629    0.00116    0.00968    0.01147
AFIX  43
H7    2    0.240809    1.106522    0.575932    11.00000   -1.20000
AFIX   0
C8    1    0.182059    0.883027    0.381594    11.00000    0.02227    0.02338 =
         0.02168    0.00566    0.00849    0.01103
C9    1    0.190513    0.695314    0.351613    11.00000    0.02380    0.02219 =
         0.01973    0.00219    0.00887    0.00909
C10   1    0.409779    0.619812    0.807377    11.00000    0.02386    0.02399 =
         0.01793    0.00298    0.00745    0.00971
HKLF 5

REM  s-5-cooh_a.res in P-1
REM R1 =  0.0347 for    2521 Fo > 4sig(Fo)  and  0.0369 for all    2715 data
REM    114 parameters refined using      0 restraints

END

WGHT      0.0598      0.0896

REM Highest difference peak  0.327,  deepest hole -0.285,  1-sigma level  0.052
Q1    1   0.3593  0.6662  0.7252  11.00000  0.05    0.33
Q2    1   0.2876  0.6361  0.5818  11.00000  0.05    0.27
;
_shelx_res_checksum              42233
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.418
_oxdiff_exptl_absorpt_empirical_full_min 0.799
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5865(14) 937 190 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4135(14) 947 190 nmt -0.9990 0.0014 0.0007 -0.0018 -1.0010 -0.0017 0.9399
0.4434 0.9996

_twin_special_details            
;
Component 2 rotated by -179.9462° 
around [0.00 -0.00 1.00] (reciprocal) or [0.42 0.20 0.89] (direct)
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4Se
_database_code_depnum_ccdc_archive 'CCDC 2332635'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 N2 O2 Se'
_chemical_formula_sum            'C8 H6 N2 O2 Se'
_chemical_formula_weight         241.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   10.02071(14)
_cell_length_b                   3.83488(5)
_cell_length_c                   21.0716(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.3939(13)
_cell_angle_gamma                90
_cell_volume                     806.16(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5694
_cell_measurement_theta_min      4.1760
_cell_measurement_theta_max      76.2840

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.042
_shelx_estimated_absorpt_T_min   0.172
_shelx_estimated_absorpt_T_max   0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5384
_diffrn_reflns_number            6542
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.215
_diffrn_reflns_theta_max         76.139
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1662
_reflns_number_gt                1604
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²+0.4479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1662
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0592
_refine_ls_wR_factor_gt          0.0585
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Se2 Se 0.34885(2) 0.95953(5) 0.44087(2) 0.01621(9) Uani 1 1 d . . . . .
O1 O 0.87935(14) 0.3859(4) 0.37390(7) 0.0259(3) Uani 1 1 d . . . . .
O2 O 0.79989(14) 0.6731(5) 0.45473(7) 0.0328(4) Uani 1 1 d . . . . .
N3 N 0.52026(15) 0.8322(4) 0.43915(7) 0.0156(3) Uani 1 1 d . . . . .
N1 N 0.30143(15) 0.8219(5) 0.36080(7) 0.0191(3) Uani 1 1 d . . . . .
C9 C 0.53270(17) 0.6955(5) 0.38211(8) 0.0146(4) Uani 1 1 d . . . . .
C7 C 0.4128(2) 0.5543(5) 0.27556(10) 0.0206(4) Uani 1 1 d . . . . .
H7 H 0.333894 0.556416 0.246776 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6536(2) 0.5537(5) 0.36051(10) 0.0162(4) Uani 1 1 d . . . . .
C8 C 0.41103(18) 0.6926(5) 0.33838(9) 0.0169(4) Uani 1 1 d . . . . .
C5 C 0.6477(2) 0.4189(5) 0.30022(9) 0.0189(4) Uani 1 1 d . . . . .
H5 H 0.726766 0.319973 0.286182 0.023 Uiso 1 1 calc R U . . .
C10 C 0.7817(2) 0.5489(5) 0.40260(10) 0.0187(4) Uani 1 1 d . . . . .
C6 C 0.5289(2) 0.4195(5) 0.25750(10) 0.0217(4) Uani 1 1 d . . . . .
H6 H 0.530781 0.324855 0.215930 0.026 Uiso 1 1 calc R U . . .
C11 C 1.0076(2) 0.3628(6) 0.41111(11) 0.0283(5) Uani 1 1 d . . . . .
H11A H 1.072704 0.251963 0.385622 0.042 Uiso 1 1 calc R U . . .
H11B H 0.998474 0.223390 0.449429 0.042 Uiso 1 1 calc R U . . .
H11C H 1.038727 0.597552 0.423518 0.042 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se2 0.01345(13) 0.02002(14) 0.01544(13) -0.00073(7) 0.00285(8) 0.00242(6)
O1 0.0201(7) 0.0365(8) 0.0216(7) -0.0022(7) 0.0047(6) 0.0117(6)
O2 0.0185(7) 0.0498(10) 0.0298(8) -0.0178(8) 0.0009(6) 0.0070(7)
N3 0.0156(7) 0.0169(8) 0.0148(7) 0.0003(6) 0.0036(5) 0.0004(6)
N1 0.0179(7) 0.0222(9) 0.0167(8) 0.0009(7) -0.0005(6) -0.0001(6)
C9 0.0172(8) 0.0133(9) 0.0136(8) 0.0016(7) 0.0036(6) -0.0012(7)
C7 0.0235(10) 0.0217(10) 0.0161(10) -0.0013(7) 0.0000(8) -0.0036(8)
C4 0.0185(9) 0.0134(9) 0.0177(9) 0.0019(7) 0.0065(7) 0.0001(7)
C8 0.0173(8) 0.0171(9) 0.0162(9) 0.0022(7) 0.0016(7) -0.0010(7)
C5 0.0243(10) 0.0156(9) 0.0182(10) 0.0014(7) 0.0094(8) 0.0002(7)
C10 0.0171(10) 0.0175(9) 0.0228(11) 0.0001(7) 0.0089(8) 0.0020(7)
C6 0.0311(11) 0.0198(10) 0.0149(9) -0.0027(7) 0.0060(8) -0.0035(8)
C11 0.0166(9) 0.0341(12) 0.0344(12) -0.0015(10) 0.0029(8) 0.0085(9)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Se2 N1 1.7889(16) . ?
Se2 N3 1.7893(15) . ?
O1 C10 1.351(2) . ?
O1 C11 1.444(2) . ?
O2 C10 1.195(3) . ?
N3 C9 1.328(2) . ?
N1 C8 1.331(2) . ?
C9 C4 1.440(3) . ?
C9 C8 1.458(2) . ?
C7 C6 1.360(3) . ?
C7 C8 1.428(3) . ?
C7 H7 0.9500 . ?
C4 C5 1.368(3) . ?
C4 C10 1.490(3) . ?
C5 C6 1.424(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
N1 Se2 N3 94.06(7) . . ?
C10 O1 C11 115.50(17) . . ?
C9 N3 Se2 107.34(12) . . ?
C8 N1 Se2 106.84(12) . . ?
N3 C9 C4 126.04(17) . . ?
N3 C9 C8 115.54(16) . . ?
C4 C9 C8 118.42(16) . . ?
C6 C7 C8 119.08(19) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C5 C4 C9 118.18(19) . . ?
C5 C4 C10 120.50(18) . . ?
C9 C4 C10 121.32(17) . . ?
N1 C8 C7 123.35(17) . . ?
N1 C8 C9 116.21(16) . . ?
C7 C8 C9 120.43(17) . . ?
C4 C5 C6 123.16(19) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
O2 C10 O1 122.8(2) . . ?
O2 C10 C4 126.18(18) . . ?
O1 C10 C4 111.04(17) . . ?
C7 C6 C5 120.70(19) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Se2 N3 C9 -0.84(13) . . . . ?
N3 Se2 N1 C8 0.34(14) . . . . ?
Se2 N3 C9 C4 -178.93(15) . . . . ?
Se2 N3 C9 C8 1.12(19) . . . . ?
N3 C9 C4 C5 179.16(18) . . . . ?
C8 C9 C4 C5 -0.9(3) . . . . ?
N3 C9 C4 C10 -0.1(3) . . . . ?
C8 C9 C4 C10 179.85(16) . . . . ?
Se2 N1 C8 C7 179.73(15) . . . . ?
Se2 N1 C8 C9 0.2(2) . . . . ?
C6 C7 C8 N1 -178.29(19) . . . . ?
C6 C7 C8 C9 1.2(3) . . . . ?
N3 C9 C8 N1 -1.0(2) . . . . ?
C4 C9 C8 N1 179.09(17) . . . . ?
N3 C9 C8 C7 179.52(17) . . . . ?
C4 C9 C8 C7 -0.4(3) . . . . ?
C9 C4 C5 C6 1.5(3) . . . . ?
C10 C4 C5 C6 -179.22(17) . . . . ?
C11 O1 C10 O2 1.5(3) . . . . ?
C11 O1 C10 C4 -179.23(17) . . . . ?
C5 C4 C10 O2 176.3(2) . . . . ?
C9 C4 C10 O2 -4.4(3) . . . . ?
C5 C4 C10 O1 -2.9(3) . . . . ?
C9 C4 C10 O1 176.32(17) . . . . ?
C8 C7 C6 C5 -0.6(3) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.091

_shelx_res_file                  
;
TITL se-4-coome_auto_a.res in P2(1)/n
    4Se.res
    created by SHELXL-2019/3 at 10:17:16 on 06-Feb-2024
REM Old TITL Se-4-COOMe_auto in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.059, Rweak 0.100, Alpha 0.038
REM <I/s> 0.775 for 237 systematic absences, Orientation as input
REM Formula found by SHELXT: C8 N2 O2 Br
CELL 1.54184 10.020711 3.834876 21.071633 90 95.3939 90
ZERR 4 0.000138 0.000051 0.00034 0 0.0013 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O Se
UNIT 32 24 8 8 4

L.S. 4 0 0
PLAN  5
SIZE 0.45 0.1 0.03
TEMP -143.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta NOHKL
OMIT -4 1 25
OMIT -1 0 1
REM <olex2.extras>
REM <HklSrc "%.\\Se-4-COOMe.hkl">
REM </olex2.extras>

WGHT    0.036300    0.447900
FVAR       7.16595
SE2   5    0.348853    0.959527    0.440873    11.00000    0.01345    0.02002 =
         0.01544   -0.00073    0.00285    0.00242
O1    4    0.879350    0.385861    0.373902    11.00000    0.02014    0.03649 =
         0.02164   -0.00219    0.00466    0.01172
O2    4    0.799893    0.673117    0.454731    11.00000    0.01848    0.04984 =
         0.02977   -0.01777    0.00095    0.00703
N3    3    0.520259    0.832203    0.439155    11.00000    0.01563    0.01686 =
         0.01483    0.00033    0.00356    0.00042
N1    3    0.301434    0.821941    0.360804    11.00000    0.01793    0.02224 =
         0.01669    0.00090   -0.00054   -0.00007
C9    1    0.532697    0.695484    0.382108    11.00000    0.01724    0.01330 =
         0.01356    0.00157    0.00360   -0.00123
C7    1    0.412765    0.554339    0.275562    11.00000    0.02350    0.02175 =
         0.01610   -0.00133   -0.00004   -0.00360
AFIX  43
H7    2    0.333894    0.556416    0.246776    11.00000   -1.20000
AFIX   0
C4    1    0.653602    0.553743    0.360511    11.00000    0.01850    0.01335 =
         0.01770    0.00194    0.00654    0.00011
C8    1    0.411027    0.692640    0.338380    11.00000    0.01735    0.01708 =
         0.01616    0.00225    0.00156   -0.00099
C5    1    0.647739    0.418868    0.300222    11.00000    0.02435    0.01556 =
         0.01824    0.00137    0.00935    0.00016
AFIX  43
H5    2    0.726766    0.319973    0.286182    11.00000   -1.20000
AFIX   0
C10   1    0.781701    0.548918    0.402600    11.00000    0.01708    0.01745 =
         0.02277    0.00008    0.00892    0.00196
C6    1    0.528925    0.419547    0.257499    11.00000    0.03113    0.01984 =
         0.01491   -0.00265    0.00600   -0.00348
AFIX  43
H6    2    0.530781    0.324855    0.215930    11.00000   -1.20000
AFIX   0
C11   1    1.007617    0.362842    0.411106    11.00000    0.01658    0.03411 =
         0.03440   -0.00152    0.00287    0.00853
AFIX 137
H11A  2    1.072704    0.251963    0.385622    11.00000   -1.50000
H11B  2    0.998474    0.223390    0.449429    11.00000   -1.50000
H11C  2    1.038727    0.597552    0.423518    11.00000   -1.50000
AFIX   0
HKLF 4




REM  se-4-coome_auto_a.res in P2(1)/n
REM wR2 = 0.0592, GooF = S = 1.078, Restrained GooF = 1.078 for all data
REM R1 = 0.0225 for 1604 Fo > 4sig(Fo) and 0.0232 for all 1662 data
REM 119 parameters refined using 0 restraints

END

WGHT      0.0363      0.4479

REM Highest difference peak  0.316,  deepest hole -0.603,  1-sigma level  0.091
Q1    1   0.2319  0.5784  0.2018  11.00000  0.05    0.32
Q2    1   1.0379  0.0755  0.3819  11.00000  0.05    0.28
Q3    1   0.3187  0.8917  0.3396  11.00000  0.05    0.28
Q4    1   0.2988  0.9643  0.4998  11.00000  0.05    0.28
Q5    1   0.4793  1.0263  0.4557  11.00000  0.05    0.27
;
_shelx_res_checksum              67978

_vrf_PLAT430_4Se                 
;
PROBLEM: Short Inter D...A Contact  Se2      ..N3       .       2.85 Ang.  
RESPONSE: An intermolecular Se...N interaction is observed between molecules 
with the formation of a planar cyclic supramolecular synthon [Se...N]2.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2Se
_database_code_depnum_ccdc_archive 'CCDC 2332633'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N2 O2 Se'
_chemical_formula_sum            'C7 H4 N2 O2 Se'
_chemical_formula_weight         227.08

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.8823(6)
_cell_length_b                   3.76622(18)
_cell_length_c                   15.6812(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.529(6)
_cell_angle_gamma                90
_cell_volume                     702.75(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2698
_cell_measurement_theta_min      2.6450
_cell_measurement_theta_max      27.9340

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_crystal_size_rad          0.067
_exptl_absorpt_coefficient_mu    5.292
_shelx_estimated_absorpt_T_min   0.226
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_correction_T_min  0.59033
_exptl_absorpt_correction_T_max  0.59779
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_reflns_number            5870
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.674
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1487
_reflns_number_gt                1217
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1487
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Se2 Se 0.54101(3) 0.86544(10) 0.40226(2) 0.01214(15) Uani 1 1 d . . . . .
O1 O 0.6826(2) 0.7741(8) 0.71449(17) 0.0184(6) Uani 1 1 d . . . . .
H1 H 0.680022 0.790066 0.767069 0.028 Uiso 1 1 calc R U . . .
O2 O 0.8513(2) 0.5435(8) 0.79465(18) 0.0193(7) Uani 1 1 d . . . . .
N1 N 0.6548(2) 0.6720(8) 0.3798(2) 0.0136(7) Uani 1 1 d . . . . .
N3 N 0.6089(3) 0.8141(8) 0.5245(2) 0.0121(7) Uani 1 1 d . . . . .
C4 C 0.7905(3) 0.5639(10) 0.6311(3) 0.0135(8) Uani 1 1 d . . . . .
C5 C 0.8870(3) 0.4016(10) 0.6353(3) 0.0131(8) Uani 1 1 d . . . . .
H5 H 0.941061 0.337221 0.694107 0.016 Uiso 1 1 calc R U . . .
C6 C 0.9104(3) 0.3248(10) 0.5562(3) 0.0151(9) Uani 1 1 d . . . . .
H6 H 0.979262 0.211961 0.563457 0.018 Uiso 1 1 calc R U . . .
C7 C 0.8364(3) 0.4093(10) 0.4699(3) 0.0141(9) Uani 1 1 d . . . . .
H7 H 0.852760 0.357366 0.417073 0.017 Uiso 1 1 calc R U . . .
C8 C 0.7334(3) 0.5779(10) 0.4608(3) 0.0121(8) Uani 1 1 d . . . . .
C9 C 0.7083(3) 0.6569(10) 0.5424(3) 0.0125(8) Uani 1 1 d . . . . .
C10 C 0.7788(3) 0.6241(10) 0.7218(3) 0.0120(8) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se2 0.0049(2) 0.0197(3) 0.0126(2) 0.00084(17) 0.00424(15) 0.00041(16)
O1 0.0085(13) 0.0386(17) 0.0093(13) -0.0002(12) 0.0047(12) 0.0066(13)
O2 0.0110(14) 0.0317(18) 0.0146(14) 0.0021(12) 0.0042(12) 0.0031(12)
N1 0.0051(14) 0.021(2) 0.0167(16) -0.0033(14) 0.0062(13) -0.0038(14)
N3 0.0074(15) 0.017(2) 0.0138(15) 0.0027(14) 0.0058(13) -0.0021(13)
C4 0.0078(17) 0.017(2) 0.0175(19) 0.0007(17) 0.0067(16) -0.0037(16)
C5 0.0060(17) 0.014(2) 0.0175(19) -0.0002(16) 0.0029(15) -0.0012(16)
C6 0.0073(17) 0.017(2) 0.023(2) -0.0005(17) 0.0077(17) -0.0002(16)
C7 0.0098(18) 0.016(2) 0.020(2) -0.0060(17) 0.0101(16) -0.0029(16)
C8 0.0065(17) 0.014(2) 0.0173(19) -0.0026(16) 0.0062(15) -0.0046(16)
C9 0.0047(16) 0.017(2) 0.0169(19) -0.0022(17) 0.0059(15) -0.0036(16)
C10 0.0082(17) 0.013(2) 0.0153(19) 0.0008(16) 0.0052(15) -0.0026(16)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Se2 N3 1.786(3) . ?
Se2 N1 1.789(3) . ?
O1 C10 1.326(4) . ?
O1 H1 0.8400 . ?
O2 C10 1.205(4) . ?
N1 C8 1.334(5) . ?
N3 C9 1.338(5) . ?
C4 C5 1.364(5) . ?
C4 C9 1.432(5) . ?
C4 C10 1.503(5) . ?
C5 C6 1.414(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.362(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.428(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.465(5) . ?

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
N3 Se2 N1 93.74(14) . . ?
C10 O1 H1 109.5 . . ?
C8 N1 Se2 107.5(2) . . ?
C9 N3 Se2 108.0(2) . . ?
C5 C4 C9 118.5(3) . . ?
C5 C4 C10 116.2(3) . . ?
C9 C4 C10 125.2(3) . . ?
C4 C5 C6 123.1(4) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 118.2(3) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
N1 C8 C7 123.4(3) . . ?
N1 C8 C9 115.9(3) . . ?
C7 C8 C9 120.8(3) . . ?
N3 C9 C4 127.2(3) . . ?
N3 C9 C8 114.8(3) . . ?
C4 C9 C8 118.0(3) . . ?
O2 C10 O1 123.2(3) . . ?
O2 C10 C4 122.5(3) . . ?
O1 C10 C4 114.3(3) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Se2 N1 C8 1.0(3) . . . . ?
N1 Se2 N3 C9 -1.0(3) . . . . ?
C9 C4 C5 C6 0.8(6) . . . . ?
C10 C4 C5 C6 179.7(3) . . . . ?
C4 C5 C6 C7 -0.2(6) . . . . ?
C5 C6 C7 C8 -0.2(6) . . . . ?
Se2 N1 C8 C7 179.1(3) . . . . ?
Se2 N1 C8 C9 -0.7(4) . . . . ?
C6 C7 C8 N1 -179.9(4) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
Se2 N3 C9 C4 -179.9(3) . . . . ?
Se2 N3 C9 C8 0.7(4) . . . . ?
C5 C4 C9 N3 179.6(4) . . . . ?
C10 C4 C9 N3 0.8(7) . . . . ?
C5 C4 C9 C8 -1.1(6) . . . . ?
C10 C4 C9 C8 -179.8(3) . . . . ?
N1 C8 C9 N3 0.0(5) . . . . ?
C7 C8 C9 N3 -179.8(3) . . . . ?
N1 C8 C9 C4 -179.4(3) . . . . ?
C7 C8 C9 C4 0.8(6) . . . . ?
C5 C4 C10 O2 1.9(6) . . . . ?
C9 C4 C10 O2 -179.3(4) . . . . ?
C5 C4 C10 O1 -178.4(3) . . . . ?
C9 C4 C10 O1 0.4(6) . . . . ?

_refine_diff_density_max         0.823
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.143

_shelx_res_file                  
;
TITL se-4-cooh_1_a.res in P2(1)/c
    2Se.res
    created by SHELXL-2019/3 at 12:40:07 on 01-Feb-2024
REM Old TITL Se-4-COOH_1 in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.085, Rweak 0.651, Alpha 0.026
REM <I/s> 0.582 for 220 systematic absences, Orientation as input
REM Formula found by SHELXT: C10 N1 O2 Se
CELL 0.71073 12.882324 3.76622 15.68117 90 112.5294 90
ZERR 4 0.000614 0.000183 0.000781 0 0.0058 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O Se
UNIT 28 16 8 8 4

L.S. 10 0 0
PLAN  5
SIZE 0.4 0.03 0.02
TEMP -173.1(10)
CONF
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\2Se.hkl">
REM </olex2.extras>

WGHT    0.040900
FVAR       2.63848
SE2   5    0.541008    0.865438    0.402256    11.00000    0.00492    0.01969 =
         0.01261    0.00084    0.00424    0.00041
O1    4    0.682618    0.774116    0.714493    11.00000    0.00852    0.03863 =
         0.00926   -0.00023    0.00467    0.00661
AFIX 147
H1    2    0.680022    0.790066    0.767069    11.00000   -1.50000
AFIX   0
O2    4    0.851260    0.543492    0.794655    11.00000    0.01099    0.03165 =
         0.01459    0.00205    0.00421    0.00307
N1    3    0.654830    0.672003    0.379849    11.00000    0.00510    0.02095 =
         0.01672   -0.00328    0.00624   -0.00376
N3    3    0.608949    0.814143    0.524468    11.00000    0.00742    0.01676 =
         0.01383    0.00266    0.00583   -0.00212
C4    1    0.790511    0.563915    0.631105    11.00000    0.00777    0.01709 =
         0.01746    0.00073    0.00674   -0.00373
C5    1    0.887021    0.401650    0.635273    11.00000    0.00595    0.01445 =
         0.01751   -0.00024    0.00288   -0.00120
AFIX  43
H5    2    0.941061    0.337221    0.694107    11.00000   -1.20000
AFIX   0
C6    1    0.910437    0.324824    0.556213    11.00000    0.00729    0.01719 =
         0.02262   -0.00050    0.00775   -0.00019
AFIX  43
H6    2    0.979262    0.211961    0.563457    11.00000   -1.20000
AFIX   0
C7    1    0.836366    0.409273    0.469878    11.00000    0.00981    0.01646 =
         0.02005   -0.00600    0.01008   -0.00293
AFIX  43
H7    2    0.852760    0.357366    0.417073    11.00000   -1.20000
AFIX   0
C8    1    0.733415    0.577897    0.460844    11.00000    0.00652    0.01384 =
         0.01731   -0.00259    0.00623   -0.00461
C9    1    0.708264    0.656894    0.542398    11.00000    0.00473    0.01748 =
         0.01693   -0.00218    0.00589   -0.00358
C10   1    0.778785    0.624095    0.721758    11.00000    0.00820    0.01304 =
         0.01528    0.00077    0.00518   -0.00260
HKLF 4




REM  se-4-cooh_1_a.res in P2(1)/c
REM wR2 = 0.0832, GooF = S = 1.051, Restrained GooF = 1.051 for all data
REM R1 = 0.0376 for 1217 Fo > 4sig(Fo) and 0.0510 for all 1487 data
REM 110 parameters refined using 0 restraints

END

WGHT      0.0409      0.0000

REM Highest difference peak  0.823,  deepest hole -1.018,  1-sigma level  0.143
Q1    1   0.5802  0.8389  0.4628  11.00000  0.05    0.82
Q2    1   0.5016  0.8761  0.3506  11.00000  0.05    0.73
Q3    1   0.5358  1.0588  0.4383  11.00000  0.05    0.70
Q4    1   0.5174  0.9891  0.3433  11.00000  0.05    0.69
Q5    1   0.5387  1.3633  0.4351  11.00000  0.05    0.65
;
_shelx_res_checksum              86148

_vrf_PLAT430_2Se                 
;
PROBLEM: Short Inter D...A Contact  Se2      ..N3       .       2.86 Ang.  
RESPONSE: An intermolecular Se...N interaction is observed between molecules 
with the formation of a planar cyclic supramolecular synthon [Se...N]2.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5Se
_database_code_depnum_ccdc_archive 'CCDC 2332636'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;
_audit_creation_date             2024-02-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 N2 O2 Se'
_chemical_formula_sum            'C8 H6 N2 O2 Se'
_chemical_formula_weight         241.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H6 N2 O2 Se'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   3.97381(10)
_cell_length_b                   6.41163(17)
_cell_length_c                   33.4053(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.357(2)
_cell_angle_gamma                90
_cell_volume                     850.40(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8849
_cell_measurement_temperature    130
_cell_measurement_theta_max      74.3170
_cell_measurement_theta_min      5.2580
_shelx_estimated_absorpt_T_max   0.763
_shelx_estimated_absorpt_T_min   0.130
_exptl_absorpt_coefficient_mu    5.728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0048
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            2689
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.551
_diffrn_reflns_theta_min         2.648
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      .
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0170245000
_diffrn_orient_matrix_UB_12      0.0208565000
_diffrn_orient_matrix_UB_13      0.0459783000
_diffrn_orient_matrix_UB_21      -0.3324851000
_diffrn_orient_matrix_UB_22      -0.1221946000
_diffrn_orient_matrix_UB_23      0.0021823000
_diffrn_orient_matrix_UB_31      0.1992637000
_diffrn_orient_matrix_UB_32      -0.2058587000
_diffrn_orient_matrix_UB_33      0.0033479000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2664
_reflns_number_total             2689
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    .
_computing_publication_material  .
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       0.0021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.211
_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)+(0.0189P)²+5.6927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1142
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8830(11)
 0.1170(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Se2 Se 0.77011(15) 0.25577(10) 0.49476(2) 0.0208(2) Uani 1 1 d . . . . .
O1 O 0.0456(12) 0.5087(8) 0.31986(12) 0.0348(11) Uani 1 1 d . . . . .
O2 O 0.0586(13) 0.1910(9) 0.29189(13) 0.0421(13) Uani 1 1 d . . . . .
N1 N 0.8205(13) 0.0426(8) 0.46080(14) 0.0229(10) Uani 1 1 d . . . . .
N3 N 0.5345(12) 0.4107(8) 0.45898(13) 0.0214(10) Uani 1 1 d . . . . .
C4 C 0.3302(15) 0.3705(10) 0.38983(15) 0.0223(12) Uani 1 1 d . . . . .
H4 H 0.2357 0.5065 0.3884 0.027 Uiso 1 1 calc R U . . .
C5 C 0.3040(14) 0.2386(11) 0.35777(15) 0.0254(12) Uani 1 1 d . . . . .
C6 C 0.4434(16) 0.0339(11) 0.35927(17) 0.0288(14) Uani 1 1 d . . . . .
H6 H 0.4144 -0.0544 0.3365 0.035 Uiso 1 1 calc R U . . .
C7 C 0.6159(16) -0.0381(10) 0.39213(17) 0.0264(13) Uani 1 1 d . . . . .
H7 H 0.7102 -0.1742 0.3924 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6540(14) 0.0945(9) 0.42659(16) 0.0204(12) Uani 1 1 d . . . . .
C9 C 0.5036(15) 0.2985(9) 0.42558(16) 0.0206(12) Uani 1 1 d . . . . .
C10 C 0.1229(16) 0.3057(11) 0.31941(17) 0.0300(15) Uani 1 1 d . . . . .
C11 C -0.1244(19) 0.5876(14) 0.28373(18) 0.0424(19) Uani 1 1 d . . . . .
H11A H 0.0162 0.5629 0.2608 0.064 Uiso 1 1 calc R U . . .
H11B H -0.1640 0.7376 0.2866 0.064 Uiso 1 1 calc R U . . .
H11C H -0.3405 0.5156 0.2794 0.064 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se2 0.0238(4) 0.0172(3) 0.0211(3) -0.0003(2) -0.0033(2) 0.0016(3)
O1 0.037(3) 0.044(3) 0.023(2) 0.0043(19) -0.0048(17) 0.004(2)
O2 0.047(3) 0.054(4) 0.024(2) -0.007(2) -0.0082(19) -0.002(3)
N1 0.027(3) 0.017(2) 0.025(2) 0.0005(19) -0.0002(18) 0.000(2)
N3 0.021(3) 0.020(3) 0.023(2) -0.0010(18) -0.0046(18) 0.004(2)
C4 0.024(3) 0.022(3) 0.021(3) 0.000(2) -0.003(2) -0.001(2)
C5 0.022(3) 0.034(3) 0.021(2) 0.000(3) -0.001(2) -0.007(3)
C6 0.029(3) 0.033(4) 0.024(3) -0.009(2) 0.002(2) -0.005(3)
C7 0.029(3) 0.021(3) 0.029(3) -0.006(2) 0.001(2) 0.001(3)
C8 0.017(3) 0.020(3) 0.024(3) 0.000(2) -0.001(2) -0.003(2)
C9 0.020(3) 0.019(3) 0.023(3) 0.000(2) 0.000(2) -0.002(2)
C10 0.026(3) 0.043(4) 0.021(3) 0.001(2) 0.001(2) -0.003(3)
C11 0.039(4) 0.062(5) 0.025(3) 0.013(3) -0.005(3) 0.009(4)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Se2 N1 1.793(5) . ?
Se2 N3 1.789(5) . ?
O1 C10 1.338(8) . ?
O1 C11 1.450(7) . ?
O2 C10 1.197(8) . ?
N1 C8 1.339(7) . ?
N3 C9 1.329(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.365(8) . ?
C4 C9 1.430(8) . ?
C5 C6 1.425(10) . ?
C5 C10 1.506(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.351(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.434(8) . ?
C8 C9 1.438(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
N3 Se2 N1 94.0(2) . . ?
C10 O1 C11 115.4(5) . . ?
C8 N1 Se2 106.7(4) . . ?
C9 N3 Se2 106.7(4) . . ?
C5 C4 H4 120.9 . . ?
C5 C4 C9 118.3(6) . . ?
C9 C4 H4 120.9 . . ?
C4 C5 C6 121.7(5) . . ?
C4 C5 C10 120.6(6) . . ?
C6 C5 C10 117.7(5) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.8(6) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.9(6) . . ?
C8 C7 H7 120.6 . . ?
N1 C8 C7 124.8(6) . . ?
N1 C8 C9 115.9(5) . . ?
C7 C8 C9 119.4(5) . . ?
N3 C9 C4 123.4(5) . . ?
N3 C9 C8 116.7(5) . . ?
C4 C9 C8 119.9(5) . . ?
O1 C10 C5 111.7(5) . . ?
O2 C10 O1 124.4(6) . . ?
O2 C10 C5 123.9(7) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se2 N1 C8 C7 -176.6(5) . . . . ?
Se2 N1 C8 C9 2.9(6) . . . . ?
Se2 N3 C9 C4 -179.8(5) . . . . ?
Se2 N3 C9 C8 0.5(6) . . . . ?
N1 Se2 N3 C9 1.0(4) . . . . ?
N1 C8 C9 N3 -2.4(8) . . . . ?
N1 C8 C9 C4 177.9(5) . . . . ?
N3 Se2 N1 C8 -2.2(4) . . . . ?
C4 C5 C6 C7 -1.7(9) . . . . ?
C4 C5 C10 O1 9.0(8) . . . . ?
C4 C5 C10 O2 -171.4(6) . . . . ?
C5 C4 C9 N3 -177.7(5) . . . . ?
C5 C4 C9 C8 2.0(8) . . . . ?
C5 C6 C7 C8 1.1(9) . . . . ?
C6 C5 C10 O1 -171.3(5) . . . . ?
C6 C5 C10 O2 8.2(9) . . . . ?
C6 C7 C8 N1 -179.5(6) . . . . ?
C6 C7 C8 C9 1.0(9) . . . . ?
C7 C8 C9 N3 177.1(5) . . . . ?
C7 C8 C9 C4 -2.6(8) . . . . ?
C9 C4 C5 C6 0.1(9) . . . . ?
C9 C4 C5 C10 179.7(5) . . . . ?
C10 C5 C6 C7 178.7(6) . . . . ?
C11 O1 C10 O2 -0.6(9) . . . . ?
C11 O1 C10 C5 179.0(5) . . . . ?

_shelx_res_file                  
;
    hklf5.res created by SHELXL-2014/7

TITL t_twin1_hklf4_a.res in P2(1)/n
REM Old TITL t_twin1_hklf4 in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.105, Rweak 0.005, Alpha 0.105
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C8 N O3 Se
CELL 1.54184 3.973812 6.411626 33.405255 90 92.3568 90
ZERR 4 0.000102 0.000173 0.000731 0 0.0021 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O Se
UNIT 32 24 8 8 4

L.S. 4 0 0
PLAN  5
SIZE 0.6 0.05 0.05
TEMP -143.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
OMIT 0 0 2
REM <olex2.extras>
REM <HklSrc "%.\\hklf5.hkl">
REM </olex2.extras>

WGHT    0.018900    5.692700
EXTI    0.002100
BASF   0.11699
FVAR       7.71253
SE2   5    0.770114    0.255769    0.494763    11.00000    0.02380    0.01720 =
         0.02109   -0.00030   -0.00328    0.00163
O1    4    0.045610    0.508712    0.319862    11.00000    0.03743    0.04359 =
         0.02276    0.00426   -0.00477    0.00436
O2    4    0.058579    0.190962    0.291892    11.00000    0.04702    0.05448 =
         0.02391   -0.00659   -0.00818   -0.00153
N1    3    0.820477    0.042614    0.460801    11.00000    0.02651    0.01748 =
         0.02465    0.00047   -0.00019   -0.00038
N3    3    0.534471    0.410722    0.458979    11.00000    0.02087    0.01996 =
         0.02284   -0.00104   -0.00462    0.00358
C4    1    0.330199    0.370451    0.389826    11.00000    0.02378    0.02194 =
         0.02085    0.00034   -0.00288   -0.00071
AFIX  43
H4    2    0.235700    0.506487    0.388429    11.00000   -1.20000
AFIX   0
C5    1    0.304023    0.238591    0.357766    11.00000    0.02156    0.03381 =
         0.02064   -0.00007   -0.00066   -0.00745
C6    1    0.443448    0.033915    0.359267    11.00000    0.02933    0.03347 =
         0.02370   -0.00930    0.00189   -0.00489
AFIX  43
H6    2    0.414420   -0.054356    0.336546    11.00000   -1.20000
AFIX   0
C7    1    0.615855   -0.038081    0.392128    11.00000    0.02867    0.02115 =
         0.02934   -0.00609    0.00069    0.00104
AFIX  43
H7    2    0.710236   -0.174231    0.392399    11.00000   -1.20000
AFIX   0
C8    1    0.653951    0.094513    0.426588    11.00000    0.01691    0.02036 =
         0.02392    0.00018   -0.00101   -0.00301
C9    1    0.503577    0.298527    0.425579    11.00000    0.01998    0.01881 =
         0.02296   -0.00008    0.00031   -0.00231
C10   1    0.122937    0.305662    0.319410    11.00000    0.02580    0.04306 =
         0.02101    0.00073    0.00083   -0.00308
C11   1   -0.124434    0.587602    0.283733    11.00000    0.03950    0.06197 =
         0.02510    0.01255   -0.00473    0.00870
AFIX 137
H11A  2    0.016230    0.562864    0.260787    11.00000   -1.50000
H11B  2   -0.164020    0.737646    0.286564    11.00000   -1.50000
H11C  2   -0.340453    0.515623    0.279428    11.00000   -1.50000
AFIX   0
HKLF 5

REM  t_twin1_hklf4_a.res in P2(1)/n
REM R1 =  0.0476 for    2664 Fo > 4sig(Fo)  and  0.0486 for all    2689 data
REM    121 parameters refined using      0 restraints

END

WGHT      0.0189      5.6952

REM Highest difference peak  0.746,  deepest hole -0.784,  1-sigma level  0.143
Q1    1   1.0202  0.1792  0.4972  11.00000  0.05    0.75
Q2    1   0.5085  0.1917  0.4954  11.00000  0.05    0.64
Q3    1   1.0211  0.2968  0.5143  11.00000  0.05    0.55
Q4    1   0.4707  0.0192  0.4812  11.00000  0.05    0.51
Q5    1   0.4638  0.5551  0.3800  11.00000  0.05    0.47
;
_shelx_res_checksum              11338
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.711
_oxdiff_exptl_absorpt_empirical_full_min 0.567
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.8830(11) 2546 10399 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.1170(11) 2539 10399 nmt 1.0005 0.0001 0.0000 0.0000 -0.9998 -0.0000 -0.7041
-0.0002 -0.9996

_twin_special_details            
;
Component 2 rotated by -179.9997° 
around [0.94 0.00 -0.33] (reciprocal) or [1.00 -0.00 -0.00] (direct)
;

_vrf_PLAT430_5Se                 
;
PROBLEM: Short Inter D...A Contact  Se2      ..N1       .       2.88 Ang.  
RESPONSE: An intermolecular Se...N interaction is observed between molecules 
with the formation of a planar cyclic supramolecular synthon [Se...N]2.
;

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3Se
_database_code_depnum_ccdc_archive 'CCDC 2332634'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N2 O2 Se'
_chemical_formula_sum            'C7 H4 N2 O2 Se'
_chemical_formula_weight         227.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   8.0711(3)
_cell_length_b                   7.5844(2)
_cell_length_c                   12.2026(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.733(3)
_cell_angle_gamma                90
_cell_volume                     718.99(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    6682
_cell_measurement_theta_min      5.8820
_cell_measurement_theta_max      75.5300

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.098
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    6.724
_shelx_estimated_absorpt_T_min   0.553
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72930
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5384
_diffrn_reflns_number            11740
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.916
_diffrn_reflns_theta_max         76.341
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1498
_reflns_number_gt                1462
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro 1.171.42.95a (Rigaku Oxford Diffraction, 2023)'
_computing_cell_refinement       
'CrysAlisPro 1.171.42.95a (Rigaku Oxford Diffraction, 2023)'
_computing_data_reduction        
'CrysAlisPro 1.171.42.95a (Rigaku Oxford Diffraction, 2023)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+1.1059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1498
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_restrained_S_all      1.196
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002

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
Se2 Se 0.74088(5) 0.53477(5) 0.26471(3) 0.02717(19) Uani 1 1 d . . . . .
O1 O 0.1853(4) 1.0057(4) 0.4540(3) 0.0332(6) Uani 1 1 d . . . . .
H1 H 0.126(10) 1.104(10) 0.483(6) 0.08(2) Uiso 1 1 d . . . . .
O2 O 0.0287(4) 0.7774(4) 0.4882(2) 0.0328(6) Uani 1 1 d . . . . .
N1 N 0.5877(4) 0.3845(4) 0.2970(3) 0.0278(6) Uani 1 1 d . . . . .
N3 N 0.6450(4) 0.7247(4) 0.3072(3) 0.0302(7) Uani 1 1 d . . . . .
C4 C 0.4018(5) 0.7880(5) 0.3818(3) 0.0278(7) Uani 1 1 d . . . . .
H4 H 0.423066 0.911370 0.386162 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2666(5) 0.7188(5) 0.4141(3) 0.0262(7) Uani 1 1 d . . . . .
C6 C 0.2336(5) 0.5316(5) 0.4093(3) 0.0261(8) Uani 1 1 d . . . . .
H6 H 0.138482 0.487312 0.432677 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3361(5) 0.4172(5) 0.3717(3) 0.0274(7) Uani 1 1 d . . . . .
H7 H 0.313391 0.294143 0.369471 0.033 Uiso 1 1 calc R U . . .
C8 C 0.4789(5) 0.4845(5) 0.3357(3) 0.0262(7) Uani 1 1 d . . . . .
C9 C 0.5114(5) 0.6711(5) 0.3412(3) 0.0274(7) Uani 1 1 d . . . . .
C10 C 0.1508(5) 0.8399(5) 0.4552(3) 0.0266(7) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se2 0.0254(3) 0.0225(3) 0.0373(3) -0.00127(14) 0.01482(18) 0.00203(13)
O1 0.0349(15) 0.0246(12) 0.0467(17) -0.0035(12) 0.0224(13) 0.0012(11)
O2 0.0314(14) 0.0305(13) 0.0403(15) -0.0001(11) 0.0163(12) 0.0024(11)
N1 0.0260(15) 0.0263(15) 0.0335(16) 0.0015(12) 0.0119(12) -0.0039(12)
N3 0.0296(16) 0.0234(15) 0.0422(18) 0.0011(13) 0.0174(14) 0.0044(12)
C4 0.0277(18) 0.0245(18) 0.0336(18) -0.0006(13) 0.0126(15) -0.0004(13)
C5 0.0266(18) 0.0248(18) 0.0287(17) 0.0008(13) 0.0098(14) 0.0030(13)
C6 0.0236(18) 0.0268(19) 0.0300(18) 0.0018(13) 0.0109(14) -0.0019(13)
C7 0.0251(17) 0.0263(17) 0.0313(17) 0.0000(14) 0.0085(14) -0.0008(15)
C8 0.0259(19) 0.0264(17) 0.0267(17) -0.0008(13) 0.0080(14) 0.0009(14)
C9 0.0272(17) 0.0245(16) 0.0314(18) 0.0022(14) 0.0097(14) -0.0007(14)
C10 0.0267(17) 0.0261(17) 0.0294(17) 0.0022(13) 0.0116(14) -0.0005(14)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Se2 N3 1.777(3) . ?
Se2 N1 1.802(3) . ?
O1 C10 1.289(5) . ?
O1 H1 1.01(8) . ?
O2 C10 1.254(5) . ?
N1 C8 1.340(5) . ?
N3 C9 1.320(5) . ?
C4 C5 1.362(5) . ?
C4 C9 1.432(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.443(5) . ?
C5 C10 1.491(5) . ?
C6 C7 1.361(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.434(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.438(5) . ?

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
N3 Se2 N1 94.03(15) . . ?
C10 O1 H1 127(5) . . ?
C8 N1 Se2 105.9(3) . . ?
C9 N3 Se2 107.4(3) . . ?
C5 C4 C9 118.7(3) . . ?
C5 C4 H4 120.7 . . ?
C9 C4 H4 120.7 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 C10 119.0(3) . . ?
C6 C5 C10 119.6(3) . . ?
C7 C6 C5 121.2(4) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.2(4) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
N1 C8 C7 124.4(4) . . ?
N1 C8 C9 116.4(3) . . ?
C7 C8 C9 119.2(4) . . ?
N3 C9 C4 123.5(3) . . ?
N3 C9 C8 116.3(3) . . ?
C4 C9 C8 120.2(3) . . ?
O2 C10 O1 124.2(3) . . ?
O2 C10 C5 119.6(3) . . ?
O1 C10 C5 116.1(3) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Se2 N1 C8 0.2(3) . . . . ?
N1 Se2 N3 C9 -0.1(3) . . . . ?
C9 C4 C5 C6 0.7(6) . . . . ?
C9 C4 C5 C10 -179.3(3) . . . . ?
C4 C5 C6 C7 -0.2(6) . . . . ?
C10 C5 C6 C7 179.7(3) . . . . ?
C5 C6 C7 C8 -0.4(6) . . . . ?
Se2 N1 C8 C7 -179.8(3) . . . . ?
Se2 N1 C8 C9 -0.2(4) . . . . ?
C6 C7 C8 N1 -179.8(4) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
Se2 N3 C9 C4 180.0(3) . . . . ?
Se2 N3 C9 C8 0.0(4) . . . . ?
C5 C4 C9 N3 179.6(4) . . . . ?
C5 C4 C9 C8 -0.4(6) . . . . ?
N1 C8 C9 N3 0.2(5) . . . . ?
C7 C8 C9 N3 179.8(3) . . . . ?
N1 C8 C9 C4 -179.8(3) . . . . ?
C7 C8 C9 C4 -0.2(5) . . . . ?
C4 C5 C10 O2 -178.0(4) . . . . ?
C6 C5 C10 O2 2.1(5) . . . . ?
C4 C5 C10 O1 1.9(5) . . . . ?
C6 C5 C10 O1 -178.0(4) . . . . ?

_refine_diff_density_max         1.596
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.121

_shelx_res_file                  
;
TITL se-5-cooh_auto_a.res in P2(1)/n
    3Se.res
    created by SHELXL-2019/3 at 09:08:29 on 02-Feb-2024
REM Old TITL Se-5-COOH_auto in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.090, Rweak 0.041, Alpha 0.040
REM <I/s> 1.120 for 120 systematic absences, Orientation as input
REM Formula found by SHELXT: C7 N2 O2 Br
CELL 1.54184 8.071149 7.584383 12.202604 90 105.7326 90
ZERR 4 0.000255 0.000197 0.000353 0 0.0032 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O Se
UNIT 28 16 8 8 4

L.S. 4 0 0
PLAN  5
SIZE 0.1 0.02 0.01
TEMP -143.15
CONF
list 4
MORE -1
BOND $H
fmap 2 53
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\Se-5-COOH_2.hkl">
REM </olex2.extras>

WGHT    0.063300    1.105900
FVAR       3.10302
SE2   5    0.740881    0.534765    0.264708    11.00000    0.02538    0.02253 =
         0.03730   -0.00127    0.01482    0.00203
O1    4    0.185253    1.005668    0.454017    11.00000    0.03485    0.02457 =
         0.04673   -0.00351    0.02244    0.00124
H1    2    0.125971    1.104397    0.483454    11.00000    0.08389
O2    4    0.028744    0.777409    0.488230    11.00000    0.03144    0.03051 =
         0.04026   -0.00009    0.01627    0.00243
N1    3    0.587718    0.384491    0.296977    11.00000    0.02598    0.02631 =
         0.03347    0.00151    0.01187   -0.00386
N3    3    0.645019    0.724666    0.307167    11.00000    0.02957    0.02342 =
         0.04218    0.00108    0.01737    0.00439
C4    1    0.401843    0.788016    0.381826    11.00000    0.02770    0.02445 =
         0.03363   -0.00059    0.01263   -0.00038
AFIX  43
H4    2    0.423066    0.911370    0.386162    11.00000   -1.20000
AFIX   0
C5    1    0.266637    0.718813    0.414127    11.00000    0.02664    0.02478 =
         0.02866    0.00080    0.00983    0.00304
C6    1    0.233590    0.531560    0.409260    11.00000    0.02360    0.02677 =
         0.03000    0.00179    0.01087   -0.00187
AFIX  43
H6    2    0.138482    0.487312    0.432677    11.00000   -1.20000
AFIX   0
C7    1    0.336124    0.417183    0.371750    11.00000    0.02509    0.02632 =
         0.03134   -0.00005    0.00849   -0.00075
AFIX  43
H7    2    0.313391    0.294143    0.369471    11.00000   -1.20000
AFIX   0
C8    1    0.478868    0.484523    0.335707    11.00000    0.02591    0.02641 =
         0.02669   -0.00082    0.00804    0.00093
C9    1    0.511391    0.671133    0.341192    11.00000    0.02723    0.02446 =
         0.03142    0.00221    0.00969   -0.00067
C10   1    0.150791    0.839869    0.455152    11.00000    0.02666    0.02606 =
         0.02935    0.00217    0.01160   -0.00052
HKLF 4




REM  se-5-cooh_auto_a.res in P2(1)/n
REM wR2 = 0.1106, GooF = S = 1.196, Restrained GooF = 1.196 for all data
REM R1 = 0.0410 for 1462 Fo > 4sig(Fo) and 0.0421 for all 1498 data
REM 113 parameters refined using 0 restraints

END

WGHT      0.0677      1.1385

REM Highest difference peak  1.596,  deepest hole -0.670,  1-sigma level  0.121
Q1    1   0.7002  0.4308  0.2686  11.00000  0.05    1.60
Q2    1   0.7942  0.5343  0.3352  11.00000  0.05    0.93
Q3    1   0.6905  0.5354  0.1865  11.00000  0.05    0.91
Q4    1   0.6995  0.6478  0.2737  11.00000  0.05    0.65
Q5    1   0.4752  0.5806  0.3395  11.00000  0.05    0.53
;
_shelx_res_checksum              76288

_vrf_PLAT430_3Se                 
;
PROBLEM: Short Inter D...A Contact  Se2      ..N3       .       2.76 Ang.  
RESPONSE: An intermolecular Se...N interaction is observed between molecules 
with the formation of a planar cyclic supramolecular synthon [Se...N]2.
;


