# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_dan10578
_database_code_depnum_ccdc_archive 'CCDC 2389699'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2025-01-28 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;

_audit_creation_method           'APEX5 v2023.9-2'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H12 F3 I O4 S, C3 H6 O'
_chemical_formula_sum            'C23 H18 F3 I O5 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         590.33

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   32.0840(11)
_cell_length_b                   6.2079(2)
_cell_length_c                   21.7596(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.7090(10)
_cell_angle_gamma                90
_cell_volume                     4151.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      6.0952
_cell_measurement_theta_max      66.7493
_cell_measurement_temperature    102.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.079
_exptl_crystal_density_diffrn    1.889
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2336

_exptl_absorpt_coefficient_mu    13.638
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.14
_exptl_absorpt_correction_T_max  0.41

_exptl_special_details           
;
;

_diffrn_ambient_temperature      102.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          'single crystal'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            33596
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_theta_min         4.39
_diffrn_reflns_theta_max         66.77
_diffrn_reflns_theta_full        66.77
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_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.

A badly disordered acetone molecule was found in the 
asymmetrical unit and could not be satisfactorily refined. The program
SQUEEZE (Spek, A.L. (2015). Acta Cryst. C71, 9-18) was therefore used 
to remove mathematically the effect of the solvent. 
The quoted formula and derived parameters are included the squeezed
acetone solvent molecule.
;

_reflns_number_total             3666
_reflns_number_gt                3373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0759
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.064
_refine_ls_number_reflns         3666
_refine_ls_number_parameters     262
_refine_ls_number_restraints     162
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+10.8751P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.766
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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'

_computing_data_collection       'Bruker APEX4 v2021.4-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.68589(2) 0.50945(3) 0.52659(2) 0.02173(9) Uani d . . . 1 . .
O O1 0.58982(7) -0.2510(4) 0.53480(11) 0.0322(5) Uani d U . . 1 . .
O O2 0.70935(8) 1.1278(4) 0.37021(11) 0.0374(6) Uani d U . . 1 . .
O O3 0.71149(7) 0.8881(4) 0.45934(10) 0.0269(5) Uani d U . . 1 . .
O O4 0.65827(7) 1.1799(4) 0.43295(11) 0.0333(5) Uani d U . . 1 . .
S S1 0.68601(2) 1.03313(12) 0.41078(3) 0.02208(16) Uani d . . . 1 . .
F F1 0.66685(7) 0.7042(4) 0.33266(11) 0.0556(6) Uani d U . . 1 . .
F F2 0.62088(8) 0.9651(4) 0.30777(10) 0.0503(6) Uani d U . . 1 . .
F F3 0.62141(6) 0.7567(3) 0.38711(10) 0.0424(5) Uani d U . . 1 . .
C C1 0.69960(9) 0.7111(5) 0.60728(13) 0.0210(6) Uani d U . . 1 . .
C C2 0.72559(9) 0.8902(5) 0.61502(14) 0.0233(6) Uani d U . . 1 . .
H H2 0.739178 0.931726 0.583398 0.028000 Uiso calc U . R 1 . .
C C3 0.73124(11) 1.0085(4) 0.67104(16) 0.0238(7) Uani d U . . 1 . .
H H3 0.748756 1.134557 0.678008 0.029000 Uiso calc U . R 1 . .
C C4 0.71146(10) 0.9434(5) 0.71682(14) 0.0249(6) Uani d U . . 1 . .
H H4 0.715929 1.024852 0.755130 0.030000 Uiso calc U . R 1 . .
C C5 0.68525(9) 0.7615(5) 0.70771(14) 0.0242(6) Uani d U . . 1 . .
H H5 0.671828 0.719985 0.739529 0.029000 Uiso calc U . R 1 . .
C C6 0.67855(9) 0.6389(5) 0.65153(13) 0.0212(6) Uani d U . . 1 . .
C C7 0.65170(10) 0.4452(5) 0.63534(14) 0.0217(6) Uani d U . . 1 . .
C C8 0.64952(9) 0.3427(5) 0.57723(13) 0.0206(6) Uani d U . . 1 . .
C C9 0.62570(9) 0.1616(5) 0.55509(14) 0.0237(6) Uani d U . . 1 . .
H H9 0.625941 0.096672 0.515661 0.028000 Uiso calc U . R 1 . .
C C10 0.60096(10) 0.0755(5) 0.59266(15) 0.0254(6) Uani d U . . 1 . .
C C11 0.60229(10) 0.1700(5) 0.65106(15) 0.0279(7) Uani d U . . 1 . .
H H11 0.585825 0.109265 0.676721 0.033000 Uiso calc U . R 1 . .
C C12 0.62738(10) 0.3520(5) 0.67235(14) 0.0259(6) Uani d U . . 1 . .
H H12 0.628041 0.414034 0.712539 0.031000 Uiso calc U . R 1 . .
C C13 0.57553(10) -0.1256(5) 0.56717(15) 0.0264(7) Uani d U . . 1 . .
C C14 0.64684(11) 0.8562(6) 0.35729(15) 0.0321(7) Uani d U . . 1 . .
C C21 0.53306(10) -0.1655(5) 0.57962(16) 0.0316(7) Uani d U . . 1 . .
C C22 0.51664(12) -0.3759(6) 0.5724(2) 0.0426(9) Uani d U . . 1 . .
H H22 0.533781 -0.489535 0.563301 0.051000 Uiso calc U . R 1 . .
C C23 0.47584(13) -0.4200(7) 0.5785(2) 0.0520(10) Uani d U . . 1 . .
H H23 0.464991 -0.563297 0.573226 0.062000 Uiso calc U . R 1 . .
C C24 0.45079(12) -0.2563(7) 0.5921(2) 0.0492(10) Uani d U . . 1 . .
H H24 0.422948 -0.287140 0.597062 0.059000 Uiso calc U . R 1 . .
C C25 0.46634(13) -0.0469(7) 0.5984(2) 0.0468(10) Uani d U . . 1 . .
H H25 0.449028 0.066225 0.607375 0.056000 Uiso calc U . R 1 . .
C C26 0.50705(13) -0.0024(5) 0.5917(2) 0.0381(9) Uani d U . . 1 . .
H H26 0.517301 0.141933 0.595522 0.046000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C8 . 2.094(3) ?
I1 C1 . 2.097(3) ?
O1 C13 . 1.224(4) ?
O2 S1 . 1.437(2) ?
O3 S1 . 1.449(2) ?
O4 S1 . 1.450(2) ?
S1 C14 . 1.816(3) ?
F1 C14 . 1.337(4) ?
F2 C14 . 1.340(4) ?
F3 C14 . 1.332(4) ?
C1 C2 . 1.371(4) ?
C1 C6 . 1.399(4) ?
C2 C3 . 1.389(4) ?
C2 H2 . 0.950000 ?
C3 C4 . 1.386(5) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.388(5) ?
C4 H4 . 0.950000 ?
C5 C6 . 1.403(4) ?
C5 H5 . 0.950000 ?
C6 C7 . 1.462(4) ?
C7 C12 . 1.397(4) ?
C7 C8 . 1.399(4) ?
C8 C9 . 1.367(4) ?
C9 C10 . 1.399(4) ?
C9 H9 . 0.950000 ?
C10 C11 . 1.389(5) ?
C10 C13 . 1.507(4) ?
C11 C12 . 1.388(5) ?
C11 H11 . 0.950000 ?
C12 H12 . 0.950000 ?
C13 C21 . 1.484(4) ?
C21 C26 . 1.385(5) ?
C21 C22 . 1.400(5) ?
C22 C23 . 1.380(5) ?
C22 H22 . 0.950000 ?
C23 C24 . 1.379(6) ?
C23 H23 . 0.950000 ?
C24 C25 . 1.385(6) ?
C24 H24 . 0.950000 ?
C25 C26 . 1.383(6) ?
C25 H25 . 0.950000 ?
C26 H26 . 0.950000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 I1 C1 . . 82.48(11) ?
O2 S1 O3 . . 114.69(13) ?
O2 S1 O4 . . 115.18(15) ?
O3 S1 O4 . . 114.81(14) ?
O2 S1 C14 . . 103.91(15) ?
O3 S1 C14 . . 103.46(14) ?
O4 S1 C14 . . 102.45(14) ?
C2 C1 C6 . . 124.9(3) ?
C2 C1 I1 . . 124.1(2) ?
C6 C1 I1 . . 111.0(2) ?
C1 C2 C3 . . 117.2(3) ?
C1 C2 H2 . . 121.400000 ?
C3 C2 H2 . . 121.400000 ?
C4 C3 C2 . . 120.3(3) ?
C4 C3 H3 . . 119.800000 ?
C2 C3 H3 . . 119.800000 ?
C3 C4 C5 . . 121.2(3) ?
C3 C4 H4 . . 119.400000 ?
C5 C4 H4 . . 119.400000 ?
C4 C5 C6 . . 120.0(3) ?
C4 C5 H5 . . 120.000000 ?
C6 C5 H5 . . 120.000000 ?
C1 C6 C5 . . 116.3(3) ?
C1 C6 C7 . . 117.7(3) ?
C5 C6 C7 . . 126.0(3) ?
C12 C7 C8 . . 116.2(3) ?
C12 C7 C6 . . 126.1(3) ?
C8 C7 C6 . . 117.7(3) ?
C9 C8 C7 . . 124.8(3) ?
C9 C8 I1 . . 124.1(2) ?
C7 C8 I1 . . 111.1(2) ?
C8 C9 C10 . . 117.5(3) ?
C8 C9 H9 . . 121.200000 ?
C10 C9 H9 . . 121.200000 ?
C11 C10 C9 . . 120.0(3) ?
C11 C10 C13 . . 123.9(3) ?
C9 C10 C13 . . 116.1(3) ?
C12 C11 C10 . . 120.8(3) ?
C12 C11 H11 . . 119.600000 ?
C10 C11 H11 . . 119.600000 ?
C11 C12 C7 . . 120.7(3) ?
C11 C12 H12 . . 119.600000 ?
C7 C12 H12 . . 119.600000 ?
O1 C13 C21 . . 120.9(3) ?
O1 C13 C10 . . 119.1(3) ?
C21 C13 C10 . . 120.0(3) ?
F3 C14 F1 . . 107.5(3) ?
F3 C14 F2 . . 107.4(3) ?
F1 C14 F2 . . 107.0(3) ?
F3 C14 S1 . . 112.1(2) ?
F1 C14 S1 . . 111.1(2) ?
F2 C14 S1 . . 111.5(2) ?
C26 C21 C22 . . 118.4(3) ?
C26 C21 C13 . . 123.2(3) ?
C22 C21 C13 . . 118.1(3) ?
C23 C22 C21 . . 120.8(4) ?
C23 C22 H22 . . 119.600000 ?
C21 C22 H22 . . 119.600000 ?
C24 C23 C22 . . 120.1(4) ?
C24 C23 H23 . . 120.000000 ?
C22 C23 H23 . . 120.000000 ?
C23 C24 C25 . . 119.8(4) ?
C23 C24 H24 . . 120.100000 ?
C25 C24 H24 . . 120.100000 ?
C26 C25 C24 . . 120.1(4) ?
C26 C25 H25 . . 120.000000 ?
C24 C25 H25 . . 120.000000 ?
C25 C26 C21 . . 120.9(3) ?
C25 C26 H26 . . 119.600000 ?
C21 C26 H26 . . 119.600000 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.2(4) ?
I1 C1 C2 C3 . . . . 179.5(2) ?
C1 C2 C3 C4 . . . . 0.7(4) ?
C2 C3 C4 C5 . . . . -0.8(5) ?
C3 C4 C5 C6 . . . . 0.4(4) ?
C2 C1 C6 C5 . . . . -0.2(4) ?
I1 C1 C6 C5 . . . . -179.9(2) ?
C2 C1 C6 C7 . . . . 179.5(3) ?
I1 C1 C6 C7 . . . . -0.2(3) ?
C4 C5 C6 C1 . . . . 0.1(4) ?
C4 C5 C6 C7 . . . . -179.6(3) ?
C1 C6 C7 C12 . . . . -178.2(3) ?
C5 C6 C7 C12 . . . . 1.5(5) ?
C1 C6 C7 C8 . . . . 1.2(4) ?
C5 C6 C7 C8 . . . . -179.1(3) ?
C12 C7 C8 C9 . . . . -0.1(4) ?
C6 C7 C8 C9 . . . . -179.5(3) ?
C12 C7 C8 I1 . . . . 177.9(2) ?
C6 C7 C8 I1 . . . . -1.6(3) ?
C7 C8 C9 C10 . . . . 1.5(4) ?
I1 C8 C9 C10 . . . . -176.2(2) ?
C8 C9 C10 C11 . . . . -2.0(4) ?
C8 C9 C10 C13 . . . . -179.3(3) ?
C9 C10 C11 C12 . . . . 1.1(5) ?
C13 C10 C11 C12 . . . . 178.2(3) ?
C10 C11 C12 C7 . . . . 0.4(5) ?
C8 C7 C12 C11 . . . . -0.9(4) ?
C6 C7 C12 C11 . . . . 178.5(3) ?
C11 C10 C13 O1 . . . . -146.7(3) ?
C9 C10 C13 O1 . . . . 30.6(4) ?
C11 C10 C13 C21 . . . . 35.4(4) ?
C9 C10 C13 C21 . . . . -147.4(3) ?
O2 S1 C14 F3 . . . . -178.8(2) ?
O3 S1 C14 F3 . . . . 61.1(3) ?
O4 S1 C14 F3 . . . . -58.5(3) ?
O2 S1 C14 F1 . . . . 61.0(3) ?
O3 S1 C14 F1 . . . . -59.1(3) ?
O4 S1 C14 F1 . . . . -178.8(2) ?
O2 S1 C14 F2 . . . . -58.3(3) ?
O3 S1 C14 F2 . . . . -178.4(2) ?
O4 S1 C14 F2 . . . . 61.9(3) ?
O1 C13 C21 C26 . . . . -152.9(3) ?
C10 C13 C21 C26 . . . . 25.0(5) ?
O1 C13 C21 C22 . . . . 20.5(5) ?
C10 C13 C21 C22 . . . . -161.6(3) ?
C26 C21 C22 C23 . . . . -1.2(6) ?
C13 C21 C22 C23 . . . . -174.9(4) ?
C21 C22 C23 C24 . . . . -0.4(7) ?
C22 C23 C24 C25 . . . . 1.3(7) ?
C23 C24 C25 C26 . . . . -0.6(7) ?
C24 C25 C26 C21 . . . . -1.0(7) ?
C22 C21 C26 C25 . . . . 1.8(6) ?
C13 C21 C26 C25 . . . . 175.3(4) ?



#=============================================================================
#  end of cif data for "dan10578"  
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

####################################################################### 
# 
# 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_dan10580
_database_code_depnum_ccdc_archive 'CCDC 2389700'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2024-10-09 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 O Se'
_chemical_formula_iupac          ?
_chemical_formula_weight         335.25

_chemical_melting_point          ?

_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                   4.81200(10)
_cell_length_b                   19.7752(5)
_cell_length_c                   14.9145(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.5190(10)
_cell_angle_gamma                90
_cell_volume                     1403.58(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      3.7385
_cell_measurement_theta_max      66.6434
_cell_measurement_temperature    101.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.047
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672

_exptl_absorpt_coefficient_mu    3.568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.85

_exptl_special_details           
;
;

_diffrn_ambient_temperature      101.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            21306
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         66.67
_diffrn_reflns_theta_full        66.67
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_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.
;

_reflns_number_total             2470
_reflns_number_gt                2268
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0575
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_number_reflns         2470
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0245P)²+1.2962P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.393
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se1 0.21182(4) 0.24422(2) 0.70339(2) 0.01556(9) Uani d . . . 1 . .
O O1 0.5956(3) 0.34444(6) 0.75557(9) 0.0185(3) Uani d . . . 1 . .
C C1 0.0126(4) 0.17781(9) 0.62710(13) 0.0170(4) Uani d . . . 1 . .
C C2 -0.1784(4) 0.13133(9) 0.65256(13) 0.0197(4) Uani d . . . 1 . .
H H2 -0.226222 0.131767 0.712114 0.024000 Uiso calc U . R 1 . .
C C3 -0.2969(4) 0.08464(10) 0.58953(14) 0.0243(4) Uani d . . . 1 . .
H H3 -0.428110 0.052679 0.605832 0.029000 Uiso calc U . R 1 . .
C C4 -0.2262(4) 0.08382(10) 0.50189(14) 0.0251(4) Uani d . . . 1 . .
H H4 -0.308452 0.051051 0.459478 0.030000 Uiso calc U . R 1 . .
C C5 -0.0372(4) 0.13037(10) 0.47632(13) 0.0216(4) Uani d . . . 1 . .
H H5 0.009831 0.129656 0.416674 0.026000 Uiso calc U . R 1 . .
C C6 0.0838(4) 0.17851(9) 0.53932(13) 0.0177(4) Uani d . . . 1 . .
C C7 0.2829(4) 0.23150(9) 0.52446(13) 0.0166(4) Uani d . . . 1 . .
C C8 0.3714(4) 0.27146(9) 0.60117(12) 0.0152(4) Uani d . . . 1 . .
C C9 0.5610(4) 0.32528(9) 0.59877(12) 0.0157(4) Uani d . . . 1 . .
C C10 0.6671(4) 0.33677(9) 0.51779(13) 0.0180(4) Uani d . . . 1 . .
H H10 0.798320 0.372250 0.514574 0.022000 Uiso calc U . R 1 . .
C C11 0.5830(4) 0.29698(10) 0.44214(13) 0.0207(4) Uani d . . . 1 . .
H H11 0.658635 0.305357 0.387870 0.025000 Uiso calc U . R 1 . .
C C12 0.3896(4) 0.24499(9) 0.44440(13) 0.0193(4) Uani d . . . 1 . .
H H12 0.330449 0.218800 0.391624 0.023000 Uiso calc U . R 1 . .
C C13 0.6529(4) 0.36448(9) 0.68263(12) 0.0160(4) Uani d . . . 1 . .
C C21 0.8158(4) 0.42856(9) 0.67962(12) 0.0165(4) Uani d . . . 1 . .
C C22 0.7349(4) 0.47913(10) 0.61611(13) 0.0208(4) Uani d . . . 1 . .
H H22 0.579230 0.472043 0.569928 0.025000 Uiso calc U . R 1 . .
C C23 0.8810(4) 0.53986(10) 0.62002(14) 0.0243(4) Uani d . . . 1 . .
H H23 0.823309 0.574580 0.577273 0.029000 Uiso calc U . R 1 . .
C C24 1.1112(4) 0.54970(10) 0.68643(15) 0.0255(4) Uani d . . . 1 . .
H H24 1.212238 0.591087 0.688810 0.031000 Uiso calc U . R 1 . .
C C25 1.1946(4) 0.49929(10) 0.74950(13) 0.0241(4) Uani d . . . 1 . .
H H25 1.354315 0.505940 0.794310 0.029000 Uiso calc U . R 1 . .
C C26 1.0450(4) 0.43931(10) 0.74709(13) 0.0194(4) Uani d . . . 1 . .
H H26 1.098638 0.405447 0.791466 0.023000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Se1 C8 . 1.8844(18) ?
Se1 C1 . 1.9014(19) ?
O1 C13 . 1.227(2) ?
C1 C2 . 1.392(3) ?
C1 C6 . 1.401(3) ?
C2 C3 . 1.379(3) ?
C2 H2 . 0.950000 ?
C3 C4 . 1.399(3) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.387(3) ?
C4 H4 . 0.950000 ?
C5 C6 . 1.402(3) ?
C5 H5 . 0.950000 ?
C6 C7 . 1.459(3) ?
C7 C12 . 1.394(3) ?
C7 C8 . 1.404(3) ?
C8 C9 . 1.406(3) ?
C9 C10 . 1.398(3) ?
C9 C13 . 1.482(3) ?
C10 C11 . 1.386(3) ?
C10 H10 . 0.950000 ?
C11 C12 . 1.390(3) ?
C11 H11 . 0.950000 ?
C12 H12 . 0.950000 ?
C13 C21 . 1.494(3) ?
C21 C22 . 1.393(3) ?
C21 C26 . 1.395(3) ?
C22 C23 . 1.388(3) ?
C22 H22 . 0.950000 ?
C23 C24 . 1.386(3) ?
C23 H23 . 0.950000 ?
C24 C25 . 1.388(3) ?
C24 H24 . 0.950000 ?
C25 C26 . 1.385(3) ?
C25 H25 . 0.950000 ?
C26 H26 . 0.950000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 Se1 C1 . . 86.73(8) ?
C2 C1 C6 . . 121.61(18) ?
C2 C1 Se1 . . 125.98(15) ?
C6 C1 Se1 . . 112.39(13) ?
C3 C2 C1 . . 118.63(18) ?
C3 C2 H2 . . 120.700000 ?
C1 C2 H2 . . 120.700000 ?
C2 C3 C4 . . 120.76(18) ?
C2 C3 H3 . . 119.600000 ?
C4 C3 H3 . . 119.600000 ?
C5 C4 C3 . . 120.64(19) ?
C5 C4 H4 . . 119.700000 ?
C3 C4 H4 . . 119.700000 ?
C4 C5 C6 . . 119.38(18) ?
C4 C5 H5 . . 120.300000 ?
C6 C5 H5 . . 120.300000 ?
C1 C6 C5 . . 118.98(17) ?
C1 C6 C7 . . 113.95(16) ?
C5 C6 C7 . . 127.07(18) ?
C12 C7 C8 . . 119.00(17) ?
C12 C7 C6 . . 126.96(18) ?
C8 C7 C6 . . 114.04(17) ?
C7 C8 C9 . . 121.68(17) ?
C7 C8 Se1 . . 112.81(14) ?
C9 C8 Se1 . . 125.51(14) ?
C10 C9 C8 . . 117.81(17) ?
C10 C9 C13 . . 122.87(17) ?
C8 C9 C13 . . 119.21(17) ?
C11 C10 C9 . . 120.75(17) ?
C11 C10 H10 . . 119.600000 ?
C9 C10 H10 . . 119.600000 ?
C10 C11 C12 . . 121.05(18) ?
C10 C11 H11 . . 119.500000 ?
C12 C11 H11 . . 119.500000 ?
C11 C12 C7 . . 119.68(18) ?
C11 C12 H12 . . 120.200000 ?
C7 C12 H12 . . 120.200000 ?
O1 C13 C9 . . 120.08(17) ?
O1 C13 C21 . . 119.23(16) ?
C9 C13 C21 . . 120.69(16) ?
C22 C21 C26 . . 119.51(17) ?
C22 C21 C13 . . 122.30(17) ?
C26 C21 C13 . . 118.03(17) ?
C23 C22 C21 . . 120.26(18) ?
C23 C22 H22 . . 119.900000 ?
C21 C22 H22 . . 119.900000 ?
C24 C23 C22 . . 119.84(19) ?
C24 C23 H23 . . 120.100000 ?
C22 C23 H23 . . 120.100000 ?
C23 C24 C25 . . 120.24(18) ?
C23 C24 H24 . . 119.900000 ?
C25 C24 H24 . . 119.900000 ?
C26 C25 C24 . . 120.02(18) ?
C26 C25 H25 . . 120.000000 ?
C24 C25 H25 . . 120.000000 ?
C25 C26 C21 . . 120.10(18) ?
C25 C26 H26 . . 119.900000 ?
C21 C26 H26 . . 119.900000 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.7(3) ?
Se1 C1 C2 C3 . . . . -177.50(14) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . -0.6(3) ?
C3 C4 C5 C6 . . . . 0.1(3) ?
C2 C1 C6 C5 . . . . -1.1(3) ?
Se1 C1 C6 C5 . . . . 177.28(14) ?
C2 C1 C6 C7 . . . . 178.87(17) ?
Se1 C1 C6 C7 . . . . -2.7(2) ?
C4 C5 C6 C1 . . . . 0.7(3) ?
C4 C5 C6 C7 . . . . -179.29(18) ?
C1 C6 C7 C12 . . . . -179.33(18) ?
C5 C6 C7 C12 . . . . 0.7(3) ?
C1 C6 C7 C8 . . . . 1.1(2) ?
C5 C6 C7 C8 . . . . -178.88(18) ?
C12 C7 C8 C9 . . . . 1.0(3) ?
C6 C7 C8 C9 . . . . -179.37(16) ?
C12 C7 C8 Se1 . . . . -178.55(14) ?
C6 C7 C8 Se1 . . . . 1.0(2) ?
C1 Se1 C8 C7 . . . . -2.06(14) ?
C1 Se1 C8 C9 . . . . 178.37(16) ?
C7 C8 C9 C10 . . . . -2.0(3) ?
Se1 C8 C9 C10 . . . . 177.55(13) ?
C7 C8 C9 C13 . . . . -178.32(16) ?
Se1 C8 C9 C13 . . . . 1.2(2) ?
C8 C9 C10 C11 . . . . 1.2(3) ?
C13 C9 C10 C11 . . . . 177.39(17) ?
C9 C10 C11 C12 . . . . 0.5(3) ?
C10 C11 C12 C7 . . . . -1.5(3) ?
C8 C7 C12 C11 . . . . 0.7(3) ?
C6 C7 C12 C11 . . . . -178.83(18) ?
C10 C9 C13 O1 . . . . -166.07(17) ?
C8 C9 C13 O1 . . . . 10.1(3) ?
C10 C9 C13 C21 . . . . 13.9(3) ?
C8 C9 C13 C21 . . . . -169.98(16) ?
O1 C13 C21 C22 . . . . -132.39(19) ?
C9 C13 C21 C22 . . . . 47.7(3) ?
O1 C13 C21 C26 . . . . 43.1(2) ?
C9 C13 C21 C26 . . . . -136.85(18) ?
C26 C21 C22 C23 . . . . -0.1(3) ?
C13 C21 C22 C23 . . . . 175.29(17) ?
C21 C22 C23 C24 . . . . 1.1(3) ?
C22 C23 C24 C25 . . . . -0.6(3) ?
C23 C24 C25 C26 . . . . -1.0(3) ?
C24 C25 C26 C21 . . . . 2.0(3) ?
C22 C21 C26 C25 . . . . -1.5(3) ?
C13 C21 C26 C25 . . . . -177.07(17) ?

####################################################################### 
# 
# 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_lh_075_2m_neu

_database_code_depnum_ccdc_archive 'CCDC 2403911'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2025-04-02 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 F3 I O4 S'
_chemical_formula_weight         532.26

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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/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                   10.160(5)
_cell_length_b                   15.349(7)
_cell_length_c                   13.056(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.40(2)
_cell_angle_gamma                90
_cell_volume                     1920.4(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5996
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      33.07

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    1.830
_shelx_estimated_absorpt_T_min   0.545
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   'SADABS, Blessing, Acta Cryst 1995 A51 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 KAPPA II (APEX II detector)'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            137648
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.506
_diffrn_reflns_theta_max         33.333
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7402
_reflns_number_gt                6346
_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       'BRUKER APEX3(v2019.1-0)'
_computing_cell_refinement       'BRUKER APEX3(v2019.1-0)'
_computing_data_reduction        'BRUKER APEX3(v2019.1-0)'
_computing_structure_solution    'BRUKER APEX3(v2019.1-0)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+1.3269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7402
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.002
_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
I1 I 0.57028(2) 0.15468(2) 0.94665(2) 0.02787(5) Uani 1 1 d . . . . .
O1 O 0.3261(2) 0.20173(12) 0.79519(15) 0.0418(4) Uani 1 1 d . . . . .
C1 C 0.4887(2) 0.05156(13) 0.84285(17) 0.0277(4) Uani 1 1 d . . . . .
C2 C 0.3684(2) 0.05796(14) 0.75377(18) 0.0308(4) Uani 1 1 d . . . . .
C3 C 0.3192(3) -0.01809(16) 0.6957(2) 0.0377(5) Uani 1 1 d . . . . .
H3 H 0.234989 -0.017095 0.635597 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3929(3) -0.09548(16) 0.7255(2) 0.0409(5) Uani 1 1 d . . . . .
H4 H 0.357218 -0.147181 0.686018 0.049 Uiso 1 1 calc R U . . .
C5 C 0.5165(3) -0.09884(15) 0.8107(2) 0.0363(5) Uani 1 1 d . . . . .
H5 H 0.567153 -0.151917 0.828022 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5676(2) -0.02351(13) 0.87228(17) 0.0297(4) Uani 1 1 d . . . . .
C7 C 0.6967(2) -0.01743(14) 0.96432(18) 0.0308(4) Uani 1 1 d . . . . .
C8 C 0.7926(3) -0.08482(17) 1.0041(2) 0.0427(6) Uani 1 1 d . . . . .
H8 H 0.775055 -0.140759 0.971230 0.051 Uiso 1 1 calc R U . . .
C9 C 0.9122(3) -0.0705(2) 1.0906(3) 0.0518(7) Uani 1 1 d . . . . .
H9 H 0.976933 -0.116658 1.116861 0.062 Uiso 1 1 calc R U . . .
C10 C 0.9394(3) 0.0101(2) 1.1398(3) 0.0511(7) Uani 1 1 d . . . . .
H10 H 1.023125 0.018809 1.199048 0.061 Uiso 1 1 calc R U . . .
C11 C 0.8466(3) 0.07871(18) 1.1044(2) 0.0418(5) Uani 1 1 d . . . . .
H11 H 0.864131 0.134133 1.138635 0.050 Uiso 1 1 calc R U . . .
C12 C 0.7278(2) 0.06284(14) 1.01715(18) 0.0305(4) Uani 1 1 d . . . . .
C13 C 0.2982(3) 0.14397(15) 0.7264(2) 0.0325(4) Uani 1 1 d . . . . .
C14 C 0.1993(2) 0.15918(14) 0.6160(2) 0.0321(4) Uani 1 1 d . . . . .
C15 C 0.0714(3) 0.19950(19) 0.6017(2) 0.0426(6) Uani 1 1 d . . . . .
H15 H 0.046138 0.215576 0.662926 0.051 Uiso 1 1 calc R U . . .
C16 C -0.0182(3) 0.2159(2) 0.4981(3) 0.0493(7) Uani 1 1 d . . . . .
H16 H -0.105882 0.242654 0.488159 0.059 Uiso 1 1 calc R U . . .
C17 C 0.0185(3) 0.19377(19) 0.4088(2) 0.0454(6) Uani 1 1 d . . . . .
H17 H -0.044273 0.204862 0.337790 0.055 Uiso 1 1 calc R U . . .
C18 C 0.1461(3) 0.15559(18) 0.4221(2) 0.0433(6) Uani 1 1 d . . . . .
H18 H 0.172556 0.142375 0.360566 0.052 Uiso 1 1 calc R U . . .
C19 C 0.2352(3) 0.13665(18) 0.5252(2) 0.0375(5) Uani 1 1 d . . . . .
H19 H 0.321345 0.108140 0.534362 0.045 Uiso 1 1 calc R U . . .
S1 S 0.68553(5) 0.31968(3) 1.17784(4) 0.02695(10) Uani 1 1 d . . . . .
F1 F 0.6521(3) 0.48797(13) 1.1595(2) 0.0860(8) Uani 1 1 d . . . . .
F2 F 0.8141(3) 0.43961(14) 1.1063(2) 0.0716(6) Uani 1 1 d . . . . .
F3 F 0.6012(3) 0.4200(2) 1.00930(18) 0.0919(9) Uani 1 1 d . . . . .
O2 O 0.7762(3) 0.33477(16) 1.28632(17) 0.0537(6) Uani 1 1 d . . . . .
O3 O 0.54252(19) 0.30779(13) 1.16772(18) 0.0441(4) Uani 1 1 d . . . . .
O4 O 0.7371(2) 0.25911(13) 1.1163(2) 0.0490(5) Uani 1 1 d . . . . .
C20 C 0.6894(3) 0.42249(18) 1.1106(2) 0.0451(6) Uani 1 1 d . . . . .


_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
I1 C1 2.069(2) . ?
I1 C12 2.102(2) . ?
O1 C13 1.226(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.383(3) . ?
C2 C3 1.391(3) . ?
C2 C13 1.486(3) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.458(3) . ?
C7 C12 1.396(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.375(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(4) . ?
C11 H11 0.9500 . ?
C13 C14 1.477(3) . ?
C14 C19 1.394(4) . ?
C14 C15 1.395(3) . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S1 O3 1.426(2) . ?
S1 O2 1.429(2) . ?
S1 O4 1.437(2) . ?
S1 C20 1.813(3) . ?
F1 C20 1.312(3) . ?
F2 C20 1.313(4) . ?
F3 C20 1.329(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 I1 C12 81.65(9) . . ?
C6 C1 C2 124.2(2) . . ?
C6 C1 I1 112.73(16) . . ?
C2 C1 I1 123.11(16) . . ?
C1 C2 C3 117.1(2) . . ?
C1 C2 C13 119.0(2) . . ?
C3 C2 C13 123.9(2) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 117.2(2) . . ?
C1 C6 C7 117.08(19) . . ?
C5 C6 C7 125.8(2) . . ?
C12 C7 C8 117.0(2) . . ?
C12 C7 C6 117.26(19) . . ?
C8 C7 C6 125.8(2) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 121.1(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 117.0(3) . . ?
C12 C11 H11 121.5 . . ?
C10 C11 H11 121.5 . . ?
C11 C12 C7 123.8(2) . . ?
C11 C12 I1 125.02(18) . . ?
C7 C12 I1 111.15(16) . . ?
O1 C13 C14 121.2(2) . . ?
O1 C13 C2 119.4(2) . . ?
C14 C13 C2 119.4(2) . . ?
C19 C14 C15 119.4(2) . . ?
C19 C14 C13 120.3(2) . . ?
C15 C14 C13 120.2(2) . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 120.3(2) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
O3 S1 O2 114.46(15) . . ?
O3 S1 O4 114.53(13) . . ?
O2 S1 O4 115.09(15) . . ?
O3 S1 C20 104.58(14) . . ?
O2 S1 C20 103.22(15) . . ?
O4 S1 C20 102.83(14) . . ?
F1 C20 F2 107.8(3) . . ?
F1 C20 F3 107.4(3) . . ?
F2 C20 F3 107.7(3) . . ?
F1 C20 S1 112.0(2) . . ?
F2 C20 S1 111.8(2) . . ?
F3 C20 S1 110.0(2) . . ?

_refine_diff_density_max         0.992
_refine_diff_density_min         -1.378
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_lh_032_2m_neu

_database_code_depnum_ccdc_archive 'CCDC 2403915'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2025-04-02 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H7 Br Se'
_chemical_formula_weight         310.05

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'
Br Br -0.6763 1.2805 '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/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                   17.2909(14)
_cell_length_b                   4.0044(3)
_cell_length_c                   14.8721(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.3747(19)
_cell_angle_gamma                90
_cell_volume                     992.89(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9491
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      79.62

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.074
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    9.420
_shelx_estimated_absorpt_T_min   0.167
_shelx_estimated_absorpt_T_max   0.671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   'SADABS, Blessing, Acta Cryst 1995 A51 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture (Photon II detector)'
_diffrn_source_type              'INCOATEC I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            32849
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.650
_diffrn_reflns_theta_max         80.217
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2133
_reflns_number_gt                2072
_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       'Bruker APEX3(v2017.3-0)'
_computing_cell_refinement       'Bruker APEX3(v2017.3-0)'
_computing_data_reduction        'Bruker APEX3(v2017.3-0)'
_computing_structure_solution    'Bruker APEX3(v2017.3-0)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²+1.8054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2133
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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
Br1 Br 0.43451(2) 0.66961(8) 0.90071(2) 0.01960(13) Uani 1 1 d . . . . .
Se1 Se 0.13211(2) 0.78943(8) 0.62622(2) 0.01469(13) Uani 1 1 d . . . . .
C1 C 0.24065(15) 0.6612(6) 0.66872(18) 0.0119(5) Uani 1 1 d . . . . .
C2 C 0.28928(16) 0.7137(6) 0.75888(18) 0.0135(5) Uani 1 1 d . . . . .
H2 H 0.269487 0.823217 0.804926 0.016 Uiso 1 1 calc R U . . .
C3 C 0.36721(16) 0.6000(7) 0.77821(18) 0.0146(5) Uani 1 1 d . . . . .
C4 C 0.39815(16) 0.4407(7) 0.71156(19) 0.0160(5) Uani 1 1 d . . . . .
H4 H 0.452316 0.367259 0.727048 0.019 Uiso 1 1 calc R U . . .
C5 C 0.34880(16) 0.3917(7) 0.62288(19) 0.0156(5) Uani 1 1 d . . . . .
H5 H 0.369252 0.284020 0.577089 0.019 Uiso 1 1 calc R U . . .
C6 C 0.26884(15) 0.4997(7) 0.59989(17) 0.0123(5) Uani 1 1 d . . . . .
C7 C 0.20846(15) 0.4633(6) 0.51100(17) 0.0122(5) Uani 1 1 d . . . . .
C8 C 0.21734(18) 0.3043(7) 0.43042(19) 0.0150(5) Uani 1 1 d . . . . .
H8 H 0.267289 0.207498 0.429511 0.018 Uiso 1 1 calc R U . . .
C9 C 0.15274(18) 0.2894(7) 0.3521(2) 0.0169(6) Uani 1 1 d . . . . .
H9 H 0.158745 0.181482 0.297461 0.020 Uiso 1 1 calc R U . . .
C10 C 0.07893(17) 0.4305(7) 0.35221(18) 0.0164(5) Uani 1 1 d . . . . .
H10 H 0.035487 0.419807 0.297585 0.020 Uiso 1 1 calc R U . . .
C11 C 0.06857(16) 0.5867(7) 0.43181(18) 0.0150(5) Uani 1 1 d . . . . .
H11 H 0.018458 0.682781 0.432345 0.018 Uiso 1 1 calc R U . . .
C12 C 0.13334(16) 0.5986(7) 0.51044(17) 0.0121(5) Uani 1 1 d . . . . .


_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
Br1 C3 1.905(3) . ?
Se1 C1 1.886(3) . ?
Se1 C12 1.889(2) . ?
C1 C2 1.397(4) . ?
C1 C6 1.403(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(4) . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.458(4) . ?
C7 C8 1.401(4) . ?
C7 C12 1.405(4) . ?
C8 C9 1.385(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 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
C1 Se1 C12 86.83(11) . . ?
C2 C1 C6 122.2(2) . . ?
C2 C1 Se1 125.0(2) . . ?
C6 C1 Se1 112.86(19) . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 122.6(2) . . ?
C2 C3 Br1 117.8(2) . . ?
C4 C3 Br1 119.6(2) . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 127.8(2) . . ?
C1 C6 C7 113.8(2) . . ?
C8 C7 C12 118.7(2) . . ?
C8 C7 C6 127.3(2) . . ?
C12 C7 C6 113.9(2) . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 118.3(2) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C7 122.0(2) . . ?
C11 C12 Se1 125.4(2) . . ?
C7 C12 Se1 112.60(19) . . ?

_refine_diff_density_max         0.855
_refine_diff_density_min         -1.133
_refine_diff_density_rms         0.143

####################################################################### 
# 
# 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_lh_056_1m_neu

_database_code_depnum_ccdc_archive 'CCDC 2403909'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2025-04-02 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 O S'
_chemical_formula_weight         288.35

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'
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                   4.7662(3)
_cell_length_b                   19.7037(11)
_cell_length_c                   14.7618(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.564(3)
_cell_angle_gamma                90
_cell_volume                     1377.22(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9866
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      79.32

_exptl_crystal_description       prism #cut needle 
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    2.030
_shelx_estimated_absorpt_T_min   0.610
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   'SADABS, Blessing, Acta Cryst 1995 A51 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture (Photon II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            22425
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.757
_diffrn_reflns_theta_max         80.311
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2814
_reflns_number_gt                2260
_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       'Bruker APEX3(v2017.3-0)'
_computing_cell_refinement       'Bruker APEX3(v2017.3-0)'
_computing_data_reduction        'Bruker APEX3(v2017.3-0)'
_computing_structure_solution    'Bruker APEX3(v2017.3-0)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+2.9223P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2814
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1400
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
S1 S 0.21351(14) 0.26004(3) 0.18835(4) 0.02223(19) Uani 1 1 d . . . . .
O1 O 0.5973(4) 0.16252(9) 0.25188(12) 0.0248(4) Uani 1 1 d . . . . .
C1 C 0.0288(6) 0.32285(13) 0.12223(18) 0.0228(5) Uani 1 1 d . . . . .
C2 C -0.1638(6) 0.36856(14) 0.15263(19) 0.0259(6) Uani 1 1 d . . . . .
H2 H -0.210867 0.366703 0.213409 0.031 Uiso 1 1 calc R U . . .
C3 C -0.2844(6) 0.41667(14) 0.0918(2) 0.0284(6) Uani 1 1 d . . . . .
H3 H -0.416789 0.448095 0.110992 0.034 Uiso 1 1 calc R U . . .
C4 C -0.2141(6) 0.41958(14) 0.0027(2) 0.0299(6) Uani 1 1 d . . . . .
H4 H -0.297221 0.453440 -0.037586 0.036 Uiso 1 1 calc R U . . .
C5 C -0.0258(6) 0.37406(14) -0.02775(19) 0.0257(6) Uani 1 1 d . . . . .
H5 H 0.019612 0.376180 -0.088702 0.031 Uiso 1 1 calc R U . . .
C6 C 0.0975(6) 0.32472(13) 0.03243(18) 0.0232(6) Uani 1 1 d . . . . .
C7 C 0.2976(6) 0.27222(13) 0.01608(18) 0.0213(5) Uani 1 1 d . . . . .
C8 C 0.4163(6) 0.25770(14) -0.06372(18) 0.0250(6) Uani 1 1 d . . . . .
H8 H 0.363677 0.283630 -0.117217 0.030 Uiso 1 1 calc R U . . .
C9 C 0.6101(6) 0.20579(14) -0.06533(18) 0.0255(6) Uani 1 1 d . . . . .
H9 H 0.692619 0.196732 -0.119697 0.031 Uiso 1 1 calc R U . . .
C10 C 0.6858(6) 0.16656(13) 0.01222(18) 0.0235(6) Uani 1 1 d . . . . .
H10 H 0.818092 0.130732 0.009722 0.028 Uiso 1 1 calc R U . . .
C11 C 0.5708(6) 0.17893(13) 0.09351(17) 0.0210(5) Uani 1 1 d . . . . .
C12 C 0.3783(6) 0.23302(13) 0.09489(17) 0.0208(5) Uani 1 1 d . . . . .
C13 C 0.6572(6) 0.14076(13) 0.17852(17) 0.0213(5) Uani 1 1 d . . . . .
C14 C 0.8175(6) 0.07607(13) 0.17641(17) 0.0217(5) Uani 1 1 d . . . . .
C15 C 1.0445(6) 0.06526(14) 0.24355(18) 0.0245(6) Uani 1 1 d . . . . .
H15 H 1.099454 0.099927 0.286678 0.029 Uiso 1 1 calc R U . . .
C16 C 1.1899(6) 0.00417(15) 0.2476(2) 0.0295(6) Uani 1 1 d . . . . .
H16 H 1.347659 -0.002505 0.292137 0.035 Uiso 1 1 calc R U . . .
C17 C 1.1041(7) -0.04726(15) 0.1861(2) 0.0310(6) Uani 1 1 d . . . . .
H17 H 1.201632 -0.089396 0.189438 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8773(7) -0.03740(15) 0.1201(2) 0.0305(6) Uani 1 1 d . . . . .
H18 H 0.818831 -0.072873 0.078601 0.037 Uiso 1 1 calc R U . . .
C19 C 0.7351(6) 0.02419(14) 0.11440(19) 0.0265(6) Uani 1 1 d . . . . .
H19 H 0.581580 0.031096 0.068337 0.032 Uiso 1 1 calc R U . . .


_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
S1 C12 1.747(3) . ?
S1 C1 1.750(3) . ?
O1 C13 1.228(3) . ?
C1 C2 1.396(4) . ?
C1 C6 1.402(4) . ?
C2 C3 1.385(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.446(4) . ?
C7 C8 1.394(4) . ?
C7 C12 1.413(4) . ?
C8 C9 1.380(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.397(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.408(4) . ?
C11 C13 1.480(4) . ?
C13 C14 1.488(4) . ?
C14 C15 1.397(4) . ?
C14 C19 1.398(4) . ?
C15 C16 1.387(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(4) . ?
C18 H18 0.9500 . ?
C19 H19 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
C12 S1 C1 91.03(13) . . ?
C2 C1 C6 121.3(3) . . ?
C2 C1 S1 125.7(2) . . ?
C6 C1 S1 112.9(2) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 128.9(3) . . ?
C1 C6 C7 111.6(2) . . ?
C8 C7 C12 119.0(2) . . ?
C8 C7 C6 128.9(2) . . ?
C12 C7 C6 112.1(2) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 121.2(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 117.7(2) . . ?
C10 C11 C13 122.8(2) . . ?
C12 C11 C13 119.4(2) . . ?
C11 C12 C7 121.2(2) . . ?
C11 C12 S1 126.5(2) . . ?
C7 C12 S1 112.3(2) . . ?
O1 C13 C11 120.0(2) . . ?
O1 C13 C14 119.3(2) . . ?
C11 C13 C14 120.7(2) . . ?
C15 C14 C19 119.3(2) . . ?
C15 C14 C13 118.3(2) . . ?
C19 C14 C13 122.2(2) . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_lh_058_3m_neu

_database_code_depnum_ccdc_archive 'CCDC 2403912'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2025-04-02 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 O S'
_chemical_formula_weight         288.35

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'
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                   3.9473(2)
_cell_length_b                   29.7393(16)
_cell_length_c                   11.4521(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.572(3)
_cell_angle_gamma                90
_cell_volume                     1343.86(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      79.96

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    2.081
_shelx_estimated_absorpt_T_min   0.648
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   'SADABS, Blessing, Acta Cryst 1995 A51 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture (Photon II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            47736
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.972
_diffrn_reflns_theta_max         80.243
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2900
_reflns_number_gt                2408
_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       'Bruker APEX3(v2017.3-0)'
_computing_cell_refinement       'Bruker APEX3(v2017.3-0)'
_computing_data_reduction        'Bruker APEX3(v2017.3-0)'
_computing_structure_solution    'Bruker APEX3(v2017.3-0)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+1.3774P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2900
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
S1 S 0.78565(11) 0.08937(2) 0.49110(4) 0.02057(12) Uani 1 1 d . . . . .
O1 O 1.0981(4) 0.26380(5) 0.58997(11) 0.0274(3) Uani 1 1 d . . . . .
C1 C 0.9055(4) 0.05893(6) 0.36806(16) 0.0209(4) Uani 1 1 d . . . . .
C2 C 1.0571(4) 0.08628(6) 0.28411(16) 0.0191(3) Uani 1 1 d . . . . .
C3 C 1.1689(4) 0.06680(6) 0.18037(16) 0.0215(4) Uani 1 1 d . . . . .
H3 H 1.273141 0.084795 0.122965 0.026 Uiso 1 1 calc R U . . .
C4 C 1.1255(5) 0.02097(7) 0.16256(17) 0.0257(4) Uani 1 1 d . . . . .
H4 H 1.200441 0.007523 0.092587 0.031 Uiso 1 1 calc R U . . .
C5 C 0.9724(5) -0.00550(6) 0.24693(18) 0.0265(4) Uani 1 1 d . . . . .
H5 H 0.943578 -0.036786 0.233184 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8617(4) 0.01287(6) 0.35003(18) 0.0240(4) Uani 1 1 d . . . . .
H6 H 0.758613 -0.005397 0.407109 0.029 Uiso 1 1 calc R U . . .
C7 C 0.9371(4) 0.13949(6) 0.43123(15) 0.0183(3) Uani 1 1 d . . . . .
C8 C 1.0781(4) 0.13282(6) 0.32060(15) 0.0181(3) Uani 1 1 d . . . . .
C9 C 1.2170(4) 0.16940(6) 0.26232(15) 0.0187(3) Uani 1 1 d . . . . .
H9 H 1.316657 0.165282 0.188501 0.022 Uiso 1 1 calc R U . . .
C10 C 1.2090(4) 0.21155(6) 0.31246(15) 0.0183(3) Uani 1 1 d . . . . .
H10 H 1.300339 0.236490 0.272137 0.022 Uiso 1 1 calc R U . . .
C11 C 1.0671(4) 0.21808(6) 0.42259(15) 0.0179(3) Uani 1 1 d . . . . .
C12 C 0.9316(4) 0.18169(6) 0.48270(15) 0.0183(3) Uani 1 1 d . . . . .
H12 H 0.837523 0.185769 0.557430 0.022 Uiso 1 1 calc R U . . .
C13 C 1.0798(4) 0.26251(6) 0.48309(15) 0.0194(3) Uani 1 1 d . . . . .
C14 C 1.0740(4) 0.30544(6) 0.41492(15) 0.0181(3) Uani 1 1 d . . . . .
C15 C 0.9272(4) 0.30903(6) 0.30277(15) 0.0186(3) Uani 1 1 d . . . . .
H15 H 0.834332 0.283208 0.264987 0.022 Uiso 1 1 calc R U . . .
C16 C 0.9175(4) 0.35055(6) 0.24668(15) 0.0202(4) Uani 1 1 d . . . . .
H16 H 0.814524 0.353103 0.171009 0.024 Uiso 1 1 calc R U . . .
C17 C 1.0575(4) 0.38825(6) 0.30072(16) 0.0214(4) Uani 1 1 d . . . . .
H17 H 1.053964 0.416385 0.261429 0.026 Uiso 1 1 calc R U . . .
C18 C 1.2030(5) 0.38484(6) 0.41249(17) 0.0227(4) Uani 1 1 d . . . . .
H18 H 1.297455 0.410676 0.449729 0.027 Uiso 1 1 calc R U . . .
C19 C 1.2099(4) 0.34383(6) 0.46916(15) 0.0201(4) Uani 1 1 d . . . . .
H19 H 1.307875 0.341666 0.545661 0.024 Uiso 1 1 calc R U . . .


_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
S1 C1 1.7508(19) . ?
S1 C7 1.7525(18) . ?
O1 C13 1.225(2) . ?
C1 C6 1.395(3) . ?
C1 C2 1.406(2) . ?
C2 C3 1.404(3) . ?
C2 C8 1.448(2) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.387(2) . ?
C7 C8 1.412(2) . ?
C8 C9 1.396(2) . ?
C9 C10 1.380(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.407(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(2) . ?
C11 C13 1.492(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.496(2) . ?
C14 C15 1.399(2) . ?
C14 C19 1.400(2) . ?
C15 C16 1.392(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C19 H19 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
C1 S1 C7 91.27(9) . . ?
C6 C1 C2 121.35(17) . . ?
C6 C1 S1 126.27(15) . . ?
C2 C1 S1 112.38(14) . . ?
C3 C2 C1 119.32(17) . . ?
C3 C2 C8 128.47(17) . . ?
C1 C2 C8 112.21(16) . . ?
C4 C3 C2 119.28(18) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.38(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 121.41(18) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 118.26(18) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
C12 C7 C8 121.30(16) . . ?
C12 C7 S1 126.43(14) . . ?
C8 C7 S1 112.26(13) . . ?
C9 C8 C7 119.30(16) . . ?
C9 C8 C2 128.83(16) . . ?
C7 C8 C2 111.87(16) . . ?
C10 C9 C8 119.67(16) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.84(16) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.12(16) . . ?
C12 C11 C13 117.75(15) . . ?
C10 C11 C13 121.95(16) . . ?
C7 C12 C11 118.75(16) . . ?
C7 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
O1 C13 C11 119.47(16) . . ?
O1 C13 C14 119.64(16) . . ?
C11 C13 C14 120.89(15) . . ?
C15 C14 C19 119.30(16) . . ?
C15 C14 C13 122.98(16) . . ?
C19 C14 C13 117.66(16) . . ?
C16 C15 C14 119.80(16) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.34(16) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.02(17) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.90(17) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.61(16) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_lh_066_1m_neu

_database_code_depnum_ccdc_archive 'CCDC 2403913'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2025-04-02 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 O Se'
_chemical_formula_weight         335.25

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'
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                   3.9799(4)
_cell_length_b                   29.881(3)
_cell_length_c                   11.4398(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.136(2)
_cell_angle_gamma                90
_cell_volume                     1359.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      4.14
_cell_measurement_theta_max      79.13

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.041
_exptl_absorpt_coefficient_mu    3.684
_shelx_estimated_absorpt_T_min   0.407
_shelx_estimated_absorpt_T_max   0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   'SADABS, Blessing, Acta Cryst 1995 A51 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture (Photon II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            45438
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.958
_diffrn_reflns_theta_max         79.447
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2932
_reflns_number_gt                2818
_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       'Bruker APEX3(v2017.3-0)'
_computing_cell_refinement       'Bruker APEX3(v2017.3-0)'
_computing_data_reduction        'Bruker APEX3(v2017.3-0)'
_computing_structure_solution    'Bruker APEX3(v2017.3-0)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.9339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2932
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
Se1 Se 0.26320(4) 0.41267(2) 0.49897(2) 0.01889(9) Uani 1 1 d . . . . .
O1 O 0.5799(4) 0.23498(4) 0.59113(10) 0.0264(3) Uani 1 1 d . . . . .
C1 C 0.4043(4) 0.44194(5) 0.36227(14) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.5487(4) 0.41222(5) 0.28322(15) 0.0186(3) Uani 1 1 d . . . . .
C3 C 0.6665(4) 0.42893(6) 0.17814(14) 0.0218(3) Uani 1 1 d . . . . .
H3 H 0.765632 0.409360 0.123788 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6375(5) 0.47430(6) 0.15386(15) 0.0241(3) Uani 1 1 d . . . . .
H4 H 0.716532 0.485757 0.082471 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4927(5) 0.50327(6) 0.23372(16) 0.0251(4) Uani 1 1 d . . . . .
H5 H 0.474412 0.534241 0.215850 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3756(4) 0.48750(5) 0.33833(15) 0.0226(3) Uani 1 1 d . . . . .
H6 H 0.278044 0.507269 0.392544 0.027 Uiso 1 1 calc R U . . .
C7 C 0.4204(4) 0.35881(5) 0.43287(14) 0.0179(3) Uani 1 1 d . . . . .
C8 C 0.5598(4) 0.36589(5) 0.32280(13) 0.0174(3) Uani 1 1 d . . . . .
C9 C 0.6960(4) 0.32937(5) 0.26455(13) 0.0184(3) Uani 1 1 d . . . . .
H9 H 0.794478 0.333552 0.190962 0.022 Uiso 1 1 calc R U . . .
C10 C 0.6874(4) 0.28719(5) 0.31398(13) 0.0183(3) Uani 1 1 d . . . . .
H10 H 0.776688 0.262413 0.273351 0.022 Uiso 1 1 calc R U . . .
C11 C 0.5482(4) 0.28061(5) 0.42359(14) 0.0180(3) Uani 1 1 d . . . . .
C12 C 0.4140(4) 0.31683(5) 0.48379(13) 0.0179(3) Uani 1 1 d . . . . .
H12 H 0.320263 0.312669 0.558176 0.021 Uiso 1 1 calc R U . . .
C13 C 0.5612(4) 0.23640(5) 0.48436(14) 0.0190(3) Uani 1 1 d . . . . .
C14 C 0.5533(4) 0.19358(5) 0.41585(14) 0.0181(3) Uani 1 1 d . . . . .
C15 C 0.6866(4) 0.15532(6) 0.47107(14) 0.0200(3) Uani 1 1 d . . . . .
H15 H 0.785210 0.157492 0.547771 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6754(4) 0.11433(5) 0.41442(14) 0.0216(3) Uani 1 1 d . . . . .
H16 H 0.768362 0.088552 0.451902 0.026 Uiso 1 1 calc R U . . .
C17 C 0.5277(4) 0.11097(5) 0.30256(15) 0.0214(3) Uani 1 1 d . . . . .
H17 H 0.519741 0.082878 0.263660 0.026 Uiso 1 1 calc R U . . .
C18 C 0.3919(4) 0.14871(5) 0.24777(14) 0.0200(3) Uani 1 1 d . . . . .
H18 H 0.289578 0.146261 0.171688 0.024 Uiso 1 1 calc R U . . .
C19 C 0.4050(4) 0.18997(5) 0.30354(14) 0.0188(3) Uani 1 1 d . . . . .
H19 H 0.313245 0.215699 0.265462 0.023 Uiso 1 1 calc R U . . .


_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
Se1 C7 1.8944(15) . ?
Se1 C1 1.8952(17) . ?
O1 C13 1.222(2) . ?
C1 C6 1.392(2) . ?
C1 C2 1.405(2) . ?
C2 C3 1.399(2) . ?
C2 C8 1.457(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.384(2) . ?
C7 C8 1.411(2) . ?
C8 C9 1.398(2) . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.404(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.399(2) . ?
C11 C13 1.493(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.500(2) . ?
C14 C19 1.398(2) . ?
C14 C15 1.401(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 H19 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
C7 Se1 C1 87.15(7) . . ?
C6 C1 C2 121.58(15) . . ?
C6 C1 Se1 126.08(13) . . ?
C2 C1 Se1 112.35(12) . . ?
C3 C2 C1 119.06(14) . . ?
C3 C2 C8 126.80(15) . . ?
C1 C2 C8 114.13(15) . . ?
C4 C3 C2 119.51(15) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.48(16) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.98(15) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.39(16) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
C12 C7 C8 121.71(14) . . ?
C12 C7 Se1 126.20(12) . . ?
C8 C7 Se1 112.07(12) . . ?
C9 C8 C7 118.73(14) . . ?
C9 C8 C2 126.96(15) . . ?
C7 C8 C2 114.30(14) . . ?
C10 C9 C8 120.04(15) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.65(14) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.13(14) . . ?
C12 C11 C13 117.54(14) . . ?
C10 C11 C13 122.15(14) . . ?
C7 C12 C11 118.73(14) . . ?
C7 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
O1 C13 C11 119.76(14) . . ?
O1 C13 C14 119.46(14) . . ?
C11 C13 C14 120.78(14) . . ?
C19 C14 C15 119.43(15) . . ?
C19 C14 C13 123.08(14) . . ?
C15 C14 C13 117.40(15) . . ?
C16 C15 C14 120.35(16) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.94(15) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 119.98(15) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.41(15) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 119.88(15) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_lh_076_2m_neu

_database_code_depnum_ccdc_archive 'CCDC 2403910'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2025-04-02 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 O Te'
_chemical_formula_weight         383.89

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Te Te -0.1759 6.3531 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   19.670(2)
_cell_length_b                   8.7121(9)
_cell_length_c                   16.4513(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.509(2)
_cell_angle_gamma                90
_cell_volume                     2818.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9564
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      79.21

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    16.612
_shelx_estimated_absorpt_T_min   0.061
_shelx_estimated_absorpt_T_max   0.515
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.01
_exptl_absorpt_correction_T_max  0.15
_exptl_absorpt_process_details   'SADABS, Blessing, Acta Cryst 1995 A51 33-38'
_exptl_absorpt_special_details   
;
 Crystal faces:

     H       K       L      d(mm)

   0.000   0.000   1.000   0.19100
  -1.000   1.000   1.000   0.09300
   0.000   1.000   1.000   0.09600
   0.000  -1.000  -1.000   0.14000
   0.000  -1.000   0.000   0.11100
   0.000   1.000  -1.000   0.12200
   1.000   1.000   1.000   0.09100
   1.000   1.000   0.000   0.11000
  -1.000   0.000  -1.000   0.07800
   1.000   0.000   0.000   0.02300
  -1.000   0.000   0.000   0.01700
  -2.000   0.000  -1.000   0.04800
  -2.000   1.000  -2.000   0.09700
   1.000   1.000   2.000   0.11600
   0.000   1.000   2.000   0.11700
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture (Photon II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            43827
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.497
_diffrn_reflns_theta_max         79.758
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3043
_reflns_number_gt                3001
_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       'Bruker APEX3(v2017.3-0)'
_computing_cell_refinement       'Bruker APEX3(v2017.3-0)'
_computing_data_reduction        'Bruker APEX3(v2017.3-0)'
_computing_structure_solution    'Bruker APEX3(v2017.3-0)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+5.1822P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
Te1 Te 0.09900(2) 0.34223(2) 0.18863(2) 0.02510(9) Uani 1 1 d . . . . .
O1 O 0.00434(11) 0.1482(2) 0.10962(13) 0.0293(4) Uani 1 1 d . . . . .
C1 C 0.12983(13) 0.5643(3) 0.22404(15) 0.0267(5) Uani 1 1 d . . . . .
C2 C 0.08522(16) 0.6793(3) 0.19378(17) 0.0259(5) Uani 1 1 d . . . . .
C3 C 0.09849(17) 0.8318(3) 0.2130(2) 0.0324(6) Uani 1 1 d . . . . .
H3 H 0.068684 0.909940 0.193282 0.039 Uiso 1 1 calc R U . . .
C4 C 0.15479(16) 0.8705(4) 0.26067(19) 0.0342(6) Uani 1 1 d . . . . .
H4 H 0.163612 0.975209 0.273092 0.041 Uiso 1 1 calc R U . . .
C5 C 0.19863(15) 0.7575(4) 0.29060(18) 0.0348(6) Uani 1 1 d . . . . .
H5 H 0.236904 0.785358 0.323810 0.042 Uiso 1 1 calc R U . . .
C6 C 0.18673(14) 0.6039(4) 0.27214(16) 0.0308(6) Uani 1 1 d . . . . .
H6 H 0.216977 0.526738 0.292029 0.037 Uiso 1 1 calc R U . . .
C7 C 0.01927(13) 0.4653(3) 0.13587(15) 0.0244(5) Uani 1 1 d . . . . .
C8 C 0.02629(13) 0.6240(3) 0.14548(15) 0.0250(5) Uani 1 1 d . . . . .
C9 C -0.02342(13) 0.7198(3) 0.10925(16) 0.0272(5) Uani 1 1 d . . . . .
H9 H -0.020055 0.827948 0.115432 0.033 Uiso 1 1 calc R U . . .
C10 C -0.07722(15) 0.6572(3) 0.06463(18) 0.0283(6) Uani 1 1 d . . . . .
H10 H -0.109689 0.723114 0.038889 0.034 Uiso 1 1 calc R U . . .
C11 C -0.08428(14) 0.4994(3) 0.05708(15) 0.0261(5) Uani 1 1 d . . . . .
H11 H -0.121602 0.458033 0.026499 0.031 Uiso 1 1 calc R U . . .
C12 C -0.03672(13) 0.4009(3) 0.09426(15) 0.0239(5) Uani 1 1 d . . . . .
C13 C -0.04360(13) 0.2325(3) 0.08933(15) 0.0256(5) Uani 1 1 d . . . . .
C14 C -0.10972(15) 0.1621(3) 0.06159(17) 0.0256(6) Uani 1 1 d . . . . .
C15 C -0.10880(14) 0.0477(3) 0.00239(16) 0.0284(5) Uani 1 1 d . . . . .
H15 H -0.067212 0.019544 -0.021627 0.034 Uiso 1 1 calc R U . . .
C16 C -0.16892(15) -0.0250(3) -0.02130(19) 0.0343(6) Uani 1 1 d . . . . .
H16 H -0.168628 -0.100178 -0.063138 0.041 Uiso 1 1 calc R U . . .
C17 C -0.22941(15) 0.0113(3) 0.0157(2) 0.0348(6) Uani 1 1 d . . . . .
H17 H -0.269970 -0.042032 0.000727 0.042 Uiso 1 1 calc R U . . .
C18 C -0.23080(15) 0.1250(4) 0.07434(18) 0.0314(6) Uani 1 1 d . . . . .
H18 H -0.272252 0.149907 0.099606 0.038 Uiso 1 1 calc R U . . .
C19 C -0.17117(14) 0.2028(3) 0.09622(16) 0.0284(5) Uani 1 1 d . . . . .
H19 H -0.172364 0.283830 0.134815 0.034 Uiso 1 1 calc R U . . .


_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
Te1 C7 2.072(2) . ?
Te1 C1 2.105(3) . ?
O1 C13 1.234(3) . ?
C1 C6 1.397(4) . ?
C1 C2 1.414(4) . ?
C2 C3 1.389(4) . ?
C2 C8 1.469(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.398(4) . ?
C7 C12 1.399(4) . ?
C8 C9 1.406(4) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.475(4) . ?
C13 C14 1.498(4) . ?
C14 C15 1.394(4) . ?
C14 C19 1.396(4) . ?
C15 C16 1.388(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.394(4) . ?
C18 H18 0.9500 . ?
C19 H19 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
C7 Te1 C1 81.35(10) . . ?
C6 C1 C2 120.3(3) . . ?
C6 C1 Te1 127.2(2) . . ?
C2 C1 Te1 112.47(19) . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 C8 125.3(3) . . ?
C1 C2 C8 115.6(2) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C8 C7 C12 121.8(2) . . ?
C8 C7 Te1 113.16(18) . . ?
C12 C7 Te1 125.07(19) . . ?
C7 C8 C9 118.2(2) . . ?
C7 C8 C2 117.3(2) . . ?
C9 C8 C2 124.4(3) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 118.5(2) . . ?
C11 C12 C13 121.8(2) . . ?
C7 C12 C13 119.7(2) . . ?
O1 C13 C12 120.6(2) . . ?
O1 C13 C14 119.3(2) . . ?
C12 C13 C14 120.1(2) . . ?
C15 C14 C19 119.6(3) . . ?
C15 C14 C13 118.6(2) . . ?
C19 C14 C13 121.7(2) . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?

_refine_diff_density_max         1.005
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_lh_061_5m

_database_code_depnum_ccdc_archive 'CCDC 2403914'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2024-11-19 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;
_vrf_PLAT094_lh_061_5m           
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.69 Report
RESPONSE: Likely disorder of Te1 in residue 1. For details see
_refine_special_details
;
_vrf_PLAT971_lh_061_5m           
;
PROBLEM: Check Calcd Resid. Dens.  0.80Ang From O1_1            3.17 eA-3  
RESPONSE: Likely disorder of Te1 in residue 1. For details see
_refine_special_details
;
_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 O Te'
_chemical_formula_weight         383.89

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Te Te -0.5308 1.6751 '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                   10.6483(11)
_cell_length_b                   20.468(2)
_cell_length_c                   13.8551(13)
_cell_angle_alpha                90
_cell_angle_beta                 110.162(3)
_cell_angle_gamma                90
_cell_volume                     2834.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9040
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      36.36

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.116
_exptl_absorpt_coefficient_mu    2.094
_shelx_estimated_absorpt_T_min   0.624
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.63
_exptl_absorpt_process_details   'SADABS, Blessing, Acta Cryst 1995 A51 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_measurement_device_type  'Bruker D8 KAPPA II (APEX II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            70437
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         36.377
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             13772
_reflns_number_gt                12848
_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       'BRUKER APEX3(v2019.1-0)'
_computing_cell_refinement       'BRUKER APEX3(v2019.1-0)'
_computing_data_reduction        'BRUKER APEX3(v2019.1-0)'
_computing_structure_solution    'BRUKER APEX3(v2019.1-0)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 Residual electron density:
 Q1 modelled as alternate position of O1\_1 lead to n. p. d. displacement
 parameters and an occupancy close to 0. Fixing the occupancies at 0.5 leads
 to both positions joining at one point with unrealistic displacement
 parameters for both positions. The long C--O bond length also supports the
 idea that Q1 is not an alternate position of O1\_1. The most likely
 explanation is a full body disorder of residue 1 and Q1 being the alternate
 position of Te1\_1. An attempt to refine this accordingly lead to a reduction
 of the negative residual density at Te1\_1, however, since no other atoms of
 the proposed orientation can be identified we prefer to leave Q1 unmodelled.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0212P)²+3.2166P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13772
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0600
_refine_ls_wR_factor_gt          0.0589
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.006
_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
Te1_1 Te 0.35907(2) 0.59465(2) 0.16513(2) 0.01302(2) Uani 1 1 d . . . . .
O1_1 O 0.69588(12) 0.48876(7) 0.55751(9) 0.0218(2) Uani 1 1 d . . . . .
C1_1 C 0.32007(13) 0.53116(7) 0.03975(10) 0.0134(2) Uani 1 1 d . . . . .
C2_1 C 0.23952(15) 0.54388(8) -0.06237(11) 0.0166(2) Uani 1 1 d . . . . .
H2_1 H 0.192070 0.583938 -0.080136 0.020 Uiso 1 1 calc R U . . .
C3_1 C 0.23015(15) 0.49708(8) -0.13707(11) 0.0180(2) Uani 1 1 d . . . . .
H3_1 H 0.175897 0.505209 -0.206449 0.022 Uiso 1 1 calc R U . . .
C4_1 C 0.29982(15) 0.43815(8) -0.11108(12) 0.0177(2) Uani 1 1 d . . . . .
H4_1 H 0.293129 0.406656 -0.162989 0.021 Uiso 1 1 calc R U . . .
C5_1 C 0.37854(14) 0.42528(7) -0.01024(11) 0.0152(2) Uani 1 1 d . . . . .
H5_1 H 0.425041 0.384928 0.006732 0.018 Uiso 1 1 calc R U . . .
C6_1 C 0.38996(13) 0.47158(7) 0.06699(10) 0.0125(2) Uani 1 1 d . . . . .
C7_1 C 0.47987(13) 0.51681(7) 0.24103(10) 0.0121(2) Uani 1 1 d . . . . .
C8_1 C 0.47427(13) 0.46382(6) 0.17477(10) 0.01158(19) Uani 1 1 d . . . . .
C9_1 C 0.55105(14) 0.40813(7) 0.21532(11) 0.0132(2) Uani 1 1 d . . . . .
H9_1 H 0.545536 0.371145 0.172630 0.016 Uiso 1 1 calc R U . . .
C10_1 C 0.63500(14) 0.40662(7) 0.31729(11) 0.0135(2) Uani 1 1 d . . . . .
H10_1 H 0.688992 0.369262 0.343339 0.016 Uiso 1 1 calc R U . . .
C11_1 C 0.64052(13) 0.46024(7) 0.38234(10) 0.0131(2) Uani 1 1 d . . . . .
C12_1 C 0.55996(13) 0.51473(7) 0.34451(10) 0.0134(2) Uani 1 1 d . . . . .
H12_1 H 0.559672 0.550085 0.388854 0.016 Uiso 1 1 calc R U . . .
C13_1 C 0.72944(14) 0.46054(7) 0.49204(10) 0.0137(2) Uani 1 1 d . . . . .
C14_1 C 0.86329(14) 0.42820(7) 0.52253(10) 0.0129(2) Uani 1 1 d . . . . .
C15_1 C 0.92250(15) 0.40704(7) 0.62401(11) 0.0156(2) Uani 1 1 d . . . . .
H15_1 H 0.874312 0.409840 0.670194 0.019 Uiso 1 1 calc R U . . .
C16_1 C 1.05194(15) 0.38183(8) 0.65774(12) 0.0187(3) Uani 1 1 d . . . . .
H16_1 H 1.091035 0.366486 0.726335 0.022 Uiso 1 1 calc R U . . .
C17_1 C 1.12406(15) 0.37913(8) 0.59092(12) 0.0192(3) Uani 1 1 d . . . . .
H17_1 H 1.213620 0.363596 0.614699 0.023 Uiso 1 1 calc R U . . .
C18_1 C 1.06474(16) 0.39922(9) 0.48913(13) 0.0205(3) Uani 1 1 d . . . . .
H18_1 H 1.113181 0.396359 0.443119 0.025 Uiso 1 1 calc R U . . .
C19_1 C 0.93485(15) 0.42344(8) 0.45484(11) 0.0165(2) Uani 1 1 d . . . . .
H19_1 H 0.894466 0.436804 0.385301 0.020 Uiso 1 1 calc R U . . .
Te1_2 Te 0.14855(2) 0.44117(2) 0.22444(2) 0.01177(2) Uani 1 1 d . . . . .
O1_2 O 0.47072(11) 0.33301(5) 0.61160(8) 0.01482(17) Uani 1 1 d . . . . .
C1_2 C 0.12042(13) 0.38146(7) 0.09627(10) 0.0125(2) Uani 1 1 d . . . . .
C2_2 C 0.03579(14) 0.39395(8) -0.00458(10) 0.0150(2) Uani 1 1 d . . . . .
H2_2 H -0.018693 0.431973 -0.019786 0.018 Uiso 1 1 calc R U . . .
C3_2 C 0.03222(15) 0.35021(8) -0.08219(11) 0.0178(2) Uani 1 1 d . . . . .
H3_2 H -0.026244 0.357999 -0.150500 0.021 Uiso 1 1 calc R U . . .
C4_2 C 0.11415(15) 0.29476(8) -0.06044(11) 0.0173(2) Uani 1 1 d . . . . .
H4_2 H 0.112257 0.265616 -0.114290 0.021 Uiso 1 1 calc R U . . .
C5_2 C 0.19821(14) 0.28210(7) 0.03944(10) 0.0145(2) Uani 1 1 d . . . . .
H5_2 H 0.253985 0.244525 0.053552 0.017 Uiso 1 1 calc R U . . .
C6_2 C 0.20100(13) 0.32475(7) 0.11971(10) 0.0118(2) Uani 1 1 d . . . . .
C7_2 C 0.27928(12) 0.36570(6) 0.29664(10) 0.01090(19) Uani 1 1 d . . . . .
C8_2 C 0.28319(12) 0.31519(7) 0.22791(10) 0.01108(19) Uani 1 1 d . . . . .
C9_2 C 0.36345(13) 0.26026(7) 0.26775(10) 0.0126(2) Uani 1 1 d . . . . .
H9_2 H 0.365581 0.225371 0.223127 0.015 Uiso 1 1 calc R U . . .
C10_2 C 0.43973(13) 0.25633(7) 0.37156(10) 0.0128(2) Uani 1 1 d . . . . .
H10_2 H 0.493185 0.218783 0.397459 0.015 Uiso 1 1 calc R U . . .
C11_2 C 0.43808(13) 0.30784(6) 0.43858(10) 0.01093(19) Uani 1 1 d . . . . .
C12_2 C 0.35639(13) 0.36215(6) 0.40087(10) 0.01142(19) Uani 1 1 d . . . . .
H12_2 H 0.353345 0.396548 0.446045 0.014 Uiso 1 1 calc R U . . .
C13_2 C 0.51552(13) 0.30574(6) 0.55084(10) 0.01109(19) Uani 1 1 d . . . . .
C14_2 C 0.64782(13) 0.27194(6) 0.59154(10) 0.01114(19) Uani 1 1 d . . . . .
C15_2 C 0.69380(13) 0.25266(7) 0.69507(10) 0.0135(2) Uani 1 1 d . . . . .
H15_2 H 0.638220 0.258304 0.735338 0.016 Uiso 1 1 calc R U . . .
C16_2 C 0.82027(14) 0.22534(7) 0.73899(11) 0.0164(2) Uani 1 1 d . . . . .
H16_2 H 0.850640 0.211944 0.808920 0.020 Uiso 1 1 calc R U . . .
C17_2 C 0.90281(14) 0.21760(8) 0.68011(12) 0.0175(2) Uani 1 1 d . . . . .
H17_2 H 0.989582 0.199316 0.710370 0.021 Uiso 1 1 calc R U . . .
C18_2 C 0.85831(14) 0.23654(8) 0.57758(12) 0.0172(2) Uani 1 1 d . . . . .
H18_2 H 0.914623 0.231230 0.537823 0.021 Uiso 1 1 calc R U . . .
C19_2 C 0.73057(14) 0.26343(7) 0.53289(11) 0.0143(2) Uani 1 1 d . . . . .
H19_2 H 0.699864 0.275958 0.462562 0.017 Uiso 1 1 calc R U . . .


_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
Te1_1 C7_1 2.0896(13) . ?
Te1_1 C1_1 2.0933(14) . ?
O1_1 C13_1 1.2279(17) . ?
C1_1 C2_1 1.403(2) . ?
C1_1 C6_1 1.4106(19) . ?
C2_1 C3_1 1.388(2) . ?
C3_1 C4_1 1.397(2) . ?
C4_1 C5_1 1.384(2) . ?
C5_1 C6_1 1.403(2) . ?
C6_1 C8_1 1.4619(19) . ?
C7_1 C12_1 1.3935(19) . ?
C7_1 C8_1 1.4088(19) . ?
C8_1 C9_1 1.4024(19) . ?
C9_1 C10_1 1.3877(19) . ?
C10_1 C11_1 1.4084(19) . ?
C11_1 C12_1 1.3944(19) . ?
C11_1 C13_1 1.4882(19) . ?
C13_1 C14_1 1.4944(19) . ?
C14_1 C15_1 1.3967(19) . ?
C14_1 C19_1 1.401(2) . ?
C15_1 C16_1 1.393(2) . ?
C16_1 C17_1 1.393(2) . ?
C17_1 C18_1 1.394(2) . ?
C18_1 C19_1 1.390(2) . ?
Te1_2 C7_2 2.0891(13) . ?
Te1_2 C1_2 2.0905(14) . ?
O1_2 C13_2 1.2347(16) . ?
C1_2 C2_2 1.4006(19) . ?
C1_2 C6_2 1.4131(19) . ?
C2_2 C3_2 1.390(2) . ?
C3_2 C4_2 1.400(2) . ?
C4_2 C5_2 1.389(2) . ?
C5_2 C6_2 1.4061(19) . ?
C6_2 C8_2 1.4653(18) . ?
C7_2 C12_2 1.3957(18) . ?
C7_2 C8_2 1.4158(18) . ?
C8_2 C9_2 1.4050(19) . ?
C9_2 C10_2 1.3891(19) . ?
C10_2 C11_2 1.4091(18) . ?
C11_2 C12_2 1.3971(18) . ?
C11_2 C13_2 1.4888(18) . ?
C13_2 C14_2 1.4946(18) . ?
C14_2 C19_2 1.4002(19) . ?
C14_2 C15_2 1.4032(19) . ?
C15_2 C16_2 1.3898(19) . ?
C16_2 C17_2 1.399(2) . ?
C17_2 C18_2 1.389(2) . ?
C18_2 C19_2 1.399(2) . ?

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
C7_1 Te1_1 C1_1 81.71(5) . . ?
C2_1 C1_1 C6_1 120.86(13) . . ?
C2_1 C1_1 Te1_1 126.81(11) . . ?
C6_1 C1_1 Te1_1 112.29(9) . . ?
C3_1 C2_1 C1_1 119.05(14) . . ?
C2_1 C3_1 C4_1 120.55(14) . . ?
C5_1 C4_1 C3_1 120.50(14) . . ?
C4_1 C5_1 C6_1 120.29(14) . . ?
C5_1 C6_1 C1_1 118.75(12) . . ?
C5_1 C6_1 C8_1 124.54(13) . . ?
C1_1 C6_1 C8_1 116.66(12) . . ?
C12_1 C7_1 C8_1 121.35(12) . . ?
C12_1 C7_1 Te1_1 126.40(10) . . ?
C8_1 C7_1 Te1_1 112.25(9) . . ?
C9_1 C8_1 C7_1 118.48(12) . . ?
C9_1 C8_1 C6_1 124.43(12) . . ?
C7_1 C8_1 C6_1 117.08(12) . . ?
C10_1 C9_1 C8_1 120.53(12) . . ?
C9_1 C10_1 C11_1 120.28(12) . . ?
C12_1 C11_1 C10_1 119.88(12) . . ?
C12_1 C11_1 C13_1 118.23(12) . . ?
C10_1 C11_1 C13_1 121.89(12) . . ?
C7_1 C12_1 C11_1 119.36(12) . . ?
O1_1 C13_1 C11_1 120.78(13) . . ?
O1_1 C13_1 C14_1 119.44(12) . . ?
C11_1 C13_1 C14_1 119.74(12) . . ?
C15_1 C14_1 C19_1 119.43(13) . . ?
C15_1 C14_1 C13_1 118.53(12) . . ?
C19_1 C14_1 C13_1 121.83(12) . . ?
C16_1 C15_1 C14_1 120.25(14) . . ?
C15_1 C16_1 C17_1 120.01(14) . . ?
C16_1 C17_1 C18_1 119.96(14) . . ?
C19_1 C18_1 C17_1 120.10(15) . . ?
C18_1 C19_1 C14_1 120.19(14) . . ?
C7_2 Te1_2 C1_2 81.44(5) . . ?
C2_2 C1_2 C6_2 120.67(13) . . ?
C2_2 C1_2 Te1_2 126.53(11) . . ?
C6_2 C1_2 Te1_2 112.77(9) . . ?
C3_2 C2_2 C1_2 119.40(14) . . ?
C2_2 C3_2 C4_2 120.47(13) . . ?
C5_2 C4_2 C3_2 120.37(14) . . ?
C4_2 C5_2 C6_2 120.19(14) . . ?
C5_2 C6_2 C1_2 118.85(12) . . ?
C5_2 C6_2 C8_2 124.66(12) . . ?
C1_2 C6_2 C8_2 116.49(12) . . ?
C12_2 C7_2 C8_2 120.97(12) . . ?
C12_2 C7_2 Te1_2 126.25(10) . . ?
C8_2 C7_2 Te1_2 112.77(9) . . ?
C9_2 C8_2 C7_2 118.36(11) . . ?
C9_2 C8_2 C6_2 125.22(12) . . ?
C7_2 C8_2 C6_2 116.41(12) . . ?
C10_2 C9_2 C8_2 120.84(12) . . ?
C9_2 C10_2 C11_2 120.22(12) . . ?
C12_2 C11_2 C10_2 119.77(12) . . ?
C12_2 C11_2 C13_2 117.57(11) . . ?
C10_2 C11_2 C13_2 122.59(12) . . ?
C7_2 C12_2 C11_2 119.79(12) . . ?
O1_2 C13_2 C11_2 119.62(12) . . ?
O1_2 C13_2 C14_2 119.17(12) . . ?
C11_2 C13_2 C14_2 121.21(11) . . ?
C19_2 C14_2 C15_2 119.38(12) . . ?
C19_2 C14_2 C13_2 122.58(12) . . ?
C15_2 C14_2 C13_2 117.86(12) . . ?
C16_2 C15_2 C14_2 120.32(13) . . ?
C15_2 C16_2 C17_2 119.93(13) . . ?
C18_2 C17_2 C16_2 120.22(13) . . ?
C17_2 C18_2 C19_2 119.97(13) . . ?
C18_2 C19_2 C14_2 120.17(13) . . ?

_refine_diff_density_max         3.193
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.103

