# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2375411'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Universitat de les Illes Balears
Spain
;
_audit_update_record             
;
2024-08-03 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT342_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.033 Ang.  
RESPONSE: As detailed in "_refine_special_details" and in the Experimental 
section, this was a problematic crystal requiring a range of assumption in 
order to secure a reasonable chemical model.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 Hg O3 S'
_chemical_formula_sum            'C11 H8 Hg O3 S'
_chemical_formula_weight         420.82

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'
Hg Hg -4.2923 7.6849 '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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   12.7721(3)
_cell_length_b                   9.5804(2)
_cell_length_c                   19.5867(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.106(2)
_cell_angle_gamma                90
_cell_volume                     2351.78(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6202
_cell_measurement_theta_min      5.7970
_cell_measurement_theta_max      72.5490

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.377
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    25.062
_shelx_estimated_absorpt_T_min   0.117
_shelx_estimated_absorpt_T_max   0.634
_exptl_absorpt_correction_type   multi-scan

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -5 -4 0.0337
-6 -4 -1 0.0336
-7 4 4 0.1119
7 -3 -3 0.0184
4 5 1 0.0767
0 1 -12 0.0106
0 -1 12 0.0066

_exptl_absorpt_correction_T_min  0.30131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.95a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            9204
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.601
_diffrn_reflns_theta_max         72.964
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3832
_reflns_number_gt                3757
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'CrysAlisPro (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'
_refine_special_details          
;
Refined as a 2-component inversion twin, major component = 0.67(4).
The ISOR command was employed for all O and C atoms.
Distance retraints were applied for the ring, 1.38 +- 0.01 and
1.50 +- 0.01 ang.
The flat command was employed for each phenyl ring.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+21.7966P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.33(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3832
_refine_ls_number_parameters     292
_refine_ls_number_restraints     184
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_restrained_S_all      1.235
_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
Hg1 Hg 0.31856(5) 0.03567(7) 0.48674(3) 0.0387(2) Uani 1 1 d . . . . .
S1 S 0.3409(5) 0.1657(5) 0.5915(3) 0.0399(12) Uani 1 1 d . . . . .
O1 O 0.5044(18) 0.2001(19) 0.4682(12) 0.055(5) Uani 1 1 d . U . . .
O2 O 0.6429(14) 0.4686(14) 0.5454(11) 0.044(4) Uani 1 1 d . U . . .
O3 O 0.5117(15) 0.4309(19) 0.6733(10) 0.053(4) Uani 1 1 d . U . . .
C1 C 0.4440(17) 0.2659(19) 0.5799(11) 0.041(5) Uani 1 1 d D U . . .
C2 C 0.5012(15) 0.2686(18) 0.5200(10) 0.037(4) Uani 1 1 d D U . . .
C3 C 0.5670(15) 0.3899(17) 0.5539(10) 0.033(4) Uani 1 1 d D U . . .
C4 C 0.5081(17) 0.3727(19) 0.6125(10) 0.041(5) Uani 1 1 d D U . . .
C5 C 0.590(2) 0.540(2) 0.6921(14) 0.050(6) Uani 1 1 d . U . . .
H5A H 0.653275 0.517989 0.672620 0.075 Uiso 1 1 calc R U . . .
H5B H 0.609949 0.545506 0.742849 0.075 Uiso 1 1 calc R U . . .
H5C H 0.559850 0.628926 0.673443 0.075 Uiso 1 1 calc R U . . .
C6 C 0.2967(18) -0.0837(18) 0.3944(12) 0.034(4) Uani 1 1 d . U . . .
C7 C 0.2222(18) -0.194(2) 0.3844(13) 0.043(5) Uani 1 1 d . U . . .
H7 H 0.176055 -0.210769 0.416109 0.052 Uiso 1 1 calc R U . . .
C8 C 0.220(2) -0.277(2) 0.3250(16) 0.054(6) Uani 1 1 d . U . . .
H8 H 0.169395 -0.350437 0.314491 0.064 Uiso 1 1 calc R U . . .
C9 C 0.298(2) -0.247(2) 0.2780(15) 0.056(6) Uani 1 1 d . U . . .
H9 H 0.301317 -0.308145 0.240217 0.067 Uiso 1 1 calc R U . . .
C10 C 0.363(2) -0.135(2) 0.2891(14) 0.049(5) Uani 1 1 d . U . . .
H10 H 0.407612 -0.112242 0.257021 0.059 Uiso 1 1 calc R U . . .
C11 C 0.365(2) -0.055(3) 0.3480(15) 0.046(5) Uani 1 1 d . U . . .
H11 H 0.412525 0.021542 0.357044 0.055 Uiso 1 1 calc R U . . .
Hg2 Hg 0.70122(4) 0.97699(7) 0.52163(3) 0.0403(2) Uani 1 1 d . . . . .
S2 S 0.6762(5) 0.8445(5) 0.4167(4) 0.0415(12) Uani 1 1 d . . . . .
O4 O 0.5191(18) 0.820(2) 0.5411(12) 0.058(5) Uani 1 1 d . U . . .
O5 O 0.3911(19) 0.5451(17) 0.4728(12) 0.055(5) Uani 1 1 d . U . . .
O6 O 0.5244(14) 0.5601(17) 0.3457(9) 0.045(3) Uani 1 1 d . U . . .
C12 C 0.5735(14) 0.7461(15) 0.4335(9) 0.029(4) Uani 1 1 d D U . . .
C13 C 0.5056(15) 0.7472(19) 0.4875(10) 0.038(5) Uani 1 1 d D U . . .
C14 C 0.4416(12) 0.6247(15) 0.4523(9) 0.024(3) Uani 1 1 d D U . . .
C15 C 0.5160(15) 0.6331(17) 0.4018(10) 0.036(4) Uani 1 1 d D U . . .
C16 C 0.449(3) 0.443(3) 0.3292(17) 0.066(7) Uani 1 1 d . U . . .
H16A H 0.483838 0.356341 0.347897 0.099 Uiso 1 1 calc R U . . .
H16B H 0.426661 0.434938 0.278592 0.099 Uiso 1 1 calc R U . . .
H16C H 0.386386 0.460175 0.350079 0.099 Uiso 1 1 calc R U . . .
C17 C 0.718(2) 1.091(2) 0.6113(13) 0.041(5) Uani 1 1 d . U . . .
C18 C 0.7869(19) 1.201(2) 0.6249(15) 0.052(6) Uani 1 1 d . U . . .
H18 H 0.829339 1.225514 0.591850 0.063 Uiso 1 1 calc R U . . .
C19 C 0.796(2) 1.277(3) 0.685(2) 0.067(8) Uani 1 1 d . U . . .
H19 H 0.843003 1.355410 0.690840 0.080 Uiso 1 1 calc R U . . .
C20 C 0.746(2) 1.249(2) 0.7341(15) 0.053(5) Uani 1 1 d . U . . .
H20 H 0.757253 1.299853 0.776485 0.064 Uiso 1 1 calc R U . . .
C21 C 0.676(2) 1.142(2) 0.7218(15) 0.051(6) Uani 1 1 d . U . . .
H21 H 0.637779 1.118503 0.757201 0.061 Uiso 1 1 calc R U . . .
C22 C 0.656(2) 1.062(3) 0.6604(15) 0.046(5) Uani 1 1 d . U . . .
H22 H 0.602579 0.991448 0.652969 0.055 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
Hg1 C6 2.11(2) . ?
Hg1 S1 2.370(6) . ?
S1 C1 1.681(18) . ?
O1 C2 1.22(3) . ?
O2 C3 1.26(2) . ?
O3 C4 1.31(3) . ?
O3 C5 1.44(3) . ?
C1 C4 1.387(12) . ?
C1 C2 1.496(12) . ?
C2 C3 1.510(12) . ?
C3 C4 1.498(12) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.41(3) . ?
C6 C11 1.40(4) . ?
C7 C8 1.40(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.51(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.35(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.38(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
Hg2 C17 2.05(2) . ?
Hg2 S2 2.384(6) . ?
S2 C12 1.699(16) . ?
O4 C13 1.24(3) . ?
O5 C14 1.12(2) . ?
O6 C15 1.32(2) . ?
O6 C16 1.47(3) . ?
C12 C15 1.386(12) . ?
C12 C13 1.492(12) . ?
C13 C14 1.518(12) . ?
C13 C15 2.03(2) . ?
C14 C15 1.500(12) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C22 1.39(4) . ?
C17 C18 1.36(3) . ?
C18 C19 1.37(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.28(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.35(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.40(4) . ?
C21 H21 0.9500 . ?
C22 H22 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
C6 Hg1 S1 178.7(6) . . ?
C1 S1 Hg1 98.6(7) . . ?
C4 O3 C5 116.1(18) . . ?
C4 C1 C2 90.8(15) . . ?
C4 C1 S1 140.2(15) . . ?
C2 C1 S1 129.0(13) . . ?
O1 C2 C1 138.2(18) . . ?
O1 C2 C3 132.5(18) . . ?
C1 C2 C3 89.1(13) . . ?
O2 C3 C4 132.6(18) . . ?
O2 C3 C2 141.0(19) . . ?
C4 C3 C2 86.1(13) . . ?
O3 C4 C1 130.4(18) . . ?
O3 C4 C3 135.8(17) . . ?
C1 C4 C3 93.8(15) . . ?
O3 C5 H5A 109.5 . . ?
O3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 123(2) . . ?
C7 C6 Hg1 119.9(17) . . ?
C11 C6 Hg1 117.0(17) . . ?
C6 C7 C8 117(2) . . ?
C6 C7 H7 121.7 . . ?
C8 C7 H7 121.7 . . ?
C7 C8 C9 119(3) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 121(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C6 121(3) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C17 Hg2 S2 178.4(7) . . ?
C12 S2 Hg2 96.2(6) . . ?
C15 O6 C16 115.5(19) . . ?
C15 C12 C13 89.6(13) . . ?
C15 C12 S2 135.1(13) . . ?
C13 C12 S2 135.2(12) . . ?
O4 C13 C12 126.7(17) . . ?
O4 C13 C14 142.3(18) . . ?
C12 C13 C14 90.4(12) . . ?
O4 C13 C15 168.3(17) . . ?
C12 C13 C15 43.1(7) . . ?
C14 C13 C15 47.4(7) . . ?
O5 C14 C15 138.9(18) . . ?
O5 C14 C13 131.2(19) . . ?
C15 C14 C13 84.5(12) . . ?
O6 C15 C12 131.6(16) . . ?
O6 C15 C14 133.0(15) . . ?
C12 C15 C14 95.4(13) . . ?
O6 C15 C13 178.9(15) . . ?
C12 C15 C13 47.3(8) . . ?
C14 C15 C13 48.1(7) . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 117(2) . . ?
C22 C17 Hg2 120.4(19) . . ?
C18 C17 Hg2 122(2) . . ?
C19 C18 C17 122(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C20 C19 C18 124(3) . . ?
C20 C19 H19 118.1 . . ?
C18 C19 H19 118.1 . . ?
C19 C20 C21 116(3) . . ?
C19 C20 H20 122.1 . . ?
C21 C20 H20 122.1 . . ?
C20 C21 C22 125(3) . . ?
C20 C21 H21 117.5 . . ?
C22 C21 H21 117.5 . . ?
C17 C22 C21 116(3) . . ?
C17 C22 H22 121.8 . . ?
C21 C22 H22 121.8 . . ?

_refine_diff_density_max         1.129
_refine_diff_density_min         -1.999
_refine_diff_density_rms         0.176



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2375412'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Universitat de les Illes Balears
Spain
;
_audit_update_record             
;
2024-08-03 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT215_shelx               
;
PROBLEM: Disordered C6        has ADP max/min Ratio .....        4.7 Note  
RESPONSE: Disorder was noted and resolved in two regions of the molecule, 
namely the Hg-bound phenyl ring and O-bound ethyl group. These were modelled
statistically with independent ADPs. 
;
_vrf_PLAT220_shelx               
;
PROBLEM: NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range       10.0 Ratio 
RESPONSE: Disorder was noted and resolved in two regions of the molecule, 
namely the Hg-bound phenyl ring and O-bound ethyl group. These were modelled
statistically with independent ADPs. The carbon atoms of the phenyl ring were
refined with the ISOR command of SHELX.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 Hg O3 S'
_chemical_formula_sum            'C12 H10 Hg O3 S'
_chemical_formula_weight         434.85

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'
Hg Hg -2.3894 9.2266 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1120(2)
_cell_length_b                   7.8713(3)
_cell_length_c                   14.3546(8)
_cell_angle_alpha                101.423(4)
_cell_angle_beta                 102.236(4)
_cell_angle_gamma                90.002(3)
_cell_volume                     660.90(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4506
_cell_measurement_theta_min      3.2700
_cell_measurement_theta_max      26.2800

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.185
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    11.794
_shelx_estimated_absorpt_T_min   0.189
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_type   analytical

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 11 -6 0.0785
-2 -11 6 0.0785
-9 1 1 0.0855
8 -1 -1 0.1065
0 1 19 0.0076
0 -1 -19 0.0076

_exptl_absorpt_correction_T_min  0.151
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.95a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            10155
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.966
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2707
_reflns_number_gt                2393
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'
_refine_special_details          
;
Each of the phenyl and ethyl groups was statistically disordered. Each
component was refined independently with ADPs. The ISOR command was employed
for each phenyl ring.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0301P)²] 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         2707
_refine_ls_number_parameters     228
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0750
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.066
_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
Hg Hg 0.29869(5) 0.98842(3) 0.59766(2) 0.02843(11) Uani 1 1 d . . . . .
S1 S 0.2147(3) 0.8576(2) 0.42872(14) 0.0245(4) Uani 1 1 d . . . . .
C1 C 0.2183(11) 0.6441(8) 0.4372(6) 0.0276(17) Uani 1 1 d . . . . .
C2 C 0.2627(11) 0.5625(8) 0.5250(6) 0.0272(17) Uani 1 1 d . . . . .
O1 O 0.3045(9) 0.6201(6) 0.6123(4) 0.0353(13) Uani 1 1 d . . . . .
C3 C 0.2259(11) 0.3872(9) 0.4535(6) 0.0309(18) Uani 1 1 d . . . . .
O2 O 0.2311(9) 0.2371(6) 0.4622(5) 0.0453(16) Uani 1 1 d . . . . .
C4 C 0.1883(11) 0.4836(8) 0.3754(6) 0.0305(18) Uani 1 1 d . . . . .
O3 O 0.1404(10) 0.4319(7) 0.2812(5) 0.0468(15) Uani 1 1 d . . . . .
C5 C 0.129(5) 0.256(2) 0.2479(17) 0.084(8) Uani 0.5 1 d . . P A 1
H5A H 0.277182 0.208328 0.268048 0.101 Uiso 0.5 1 calc R U P A 1
H5B H 0.019676 0.201461 0.276229 0.101 Uiso 0.5 1 calc R U P A 1
C6 C 0.069(10) 0.224(3) 0.156(2) 0.27(4) Uani 0.5 1 d . . P A 1
H6A H -0.087621 0.253813 0.137202 0.398 Uiso 0.5 1 calc R U P A 1
H6B H 0.082925 0.099729 0.131559 0.398 Uiso 0.5 1 calc R U P A 1
H6C H 0.164285 0.291806 0.129243 0.398 Uiso 0.5 1 calc R U P A 1
C5A C 0.113(4) 0.547(2) 0.2141(15) 0.062(6) Uani 0.5 1 d . . P A 2
H5A1 H 0.253486 0.616412 0.223677 0.074 Uiso 0.5 1 calc R U P A 2
H5A2 H -0.007313 0.627323 0.226151 0.074 Uiso 0.5 1 calc R U P A 2
C6A C 0.054(6) 0.447(4) 0.1144(19) 0.129(12) Uani 0.5 1 d . . P A 2
H6A1 H 0.180265 0.376463 0.100478 0.194 Uiso 0.5 1 calc R U P A 2
H6A2 H 0.020997 0.526002 0.069036 0.194 Uiso 0.5 1 calc R U P A 2
H6A3 H -0.077804 0.370386 0.106817 0.194 Uiso 0.5 1 calc R U P A 2
C7 C 0.356(6) 1.096(5) 0.740(3) 0.023(8) Uani 0.5 1 d . U P B 1
C8 C 0.249(3) 1.023(2) 0.8042(14) 0.055(5) Uani 0.5 1 d . U P B 1
H8 H 0.146264 0.926860 0.777325 0.066 Uiso 0.5 1 calc R U P B 1
C9 C 0.292(4) 1.090(3) 0.9070(19) 0.084(7) Uani 0.5 1 d . U P B 1
H9 H 0.220967 1.037547 0.947826 0.101 Uiso 0.5 1 calc R U P B 1
C10 C 0.439(5) 1.233(4) 0.945(2) 0.062(8) Uani 0.5 1 d . U P B 1
H10 H 0.462890 1.283549 1.012906 0.075 Uiso 0.5 1 calc R U P B 1
C11 C 0.549(4) 1.303(3) 0.8874(18) 0.076(6) Uani 0.5 1 d . U P B 1
H11 H 0.652118 1.398568 0.914977 0.091 Uiso 0.5 1 calc R U P B 1
C12 C 0.509(4) 1.231(3) 0.7844(17) 0.070(6) Uani 0.5 1 d . U P B 1
H12 H 0.591520 1.278595 0.745897 0.085 Uiso 0.5 1 calc R U P B 1
C7A C 0.386(6) 1.089(6) 0.750(3) 0.036(11) Uani 0.5 1 d . U P B 2
C8A C 0.278(3) 1.233(2) 0.7854(15) 0.059(5) Uani 0.5 1 d . U P B 2
H8A H 0.170306 1.285354 0.743071 0.071 Uiso 0.5 1 calc R U P B 2
C9A C 0.331(4) 1.300(3) 0.8881(19) 0.079(7) Uani 0.5 1 d . U P B 2
H9A H 0.253474 1.392586 0.918025 0.095 Uiso 0.5 1 calc R U P B 2
C10A C 0.513(5) 1.217(4) 0.944(3) 0.074(10) Uani 0.5 1 d . U P B 2
H10A H 0.555829 1.259046 1.012205 0.088 Uiso 0.5 1 calc R U P B 2
C11A C 0.615(4) 1.094(3) 0.9061(18) 0.077(6) Uani 0.5 1 d . U P B 2
H11A H 0.733113 1.045582 0.945728 0.092 Uiso 0.5 1 calc R U P B 2
C12A C 0.556(3) 1.026(3) 0.8051(15) 0.059(5) Uani 0.5 1 d . U P B 2
H12A H 0.638250 0.934484 0.776791 0.070 Uiso 0.5 1 calc R U P B 2


_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
Hg C7 2.00(4) . ?
Hg C7A 2.12(4) . ?
Hg S1 2.3850(19) . ?
S1 C1 1.709(6) . ?
C1 C4 1.380(10) . ?
C1 C2 1.500(11) . ?
C2 O1 1.216(9) . ?
C2 C3 1.533(10) . ?
C3 O2 1.212(8) . ?
C3 C4 1.453(10) . ?
C4 O3 1.303(10) . ?
O3 C5 1.367(18) . ?
O3 C5A 1.43(2) . ?
C5 C6 1.26(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C5A C6A 1.46(3) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A H6A1 0.9800 . ?
C6A H6A2 0.9800 . ?
C6A H6A3 0.9800 . ?
C7 C12 1.37(4) . ?
C7 C8 1.44(4) . ?
C8 C9 1.43(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.39(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.37(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.44(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C7A C12A 1.33(4) . ?
C7A C8A 1.38(4) . ?
C8A C9A 1.43(3) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.46(4) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.25(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.41(3) . ?
C11A H11A 0.9500 . ?
C12A H12A 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 Hg S1 177.6(10) . . ?
C7A Hg S1 175.9(11) . . ?
C1 S1 Hg 99.4(3) . . ?
C4 C1 C2 91.5(6) . . ?
C4 C1 S1 138.1(7) . . ?
C2 C1 S1 130.4(6) . . ?
O1 C2 C1 133.8(6) . . ?
O1 C2 C3 139.5(7) . . ?
C1 C2 C3 86.6(6) . . ?
O2 C3 C4 138.0(8) . . ?
O2 C3 C2 134.5(8) . . ?
C4 C3 C2 87.4(5) . . ?
O3 C4 C1 134.1(7) . . ?
O3 C4 C3 131.5(6) . . ?
C1 C4 C3 94.5(7) . . ?
C4 O3 C5 115.6(11) . . ?
C4 O3 C5A 123.9(9) . . ?
C6 C5 O3 109(2) . . ?
C6 C5 H5A 109.8 . . ?
O3 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
O3 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C5A C6A 109.8(17) . . ?
O3 C5A H5A1 109.7 . . ?
C6A C5A H5A1 109.7 . . ?
O3 C5A H5A2 109.7 . . ?
C6A C5A H5A2 109.7 . . ?
H5A1 C5A H5A2 108.2 . . ?
C5A C6A H6A1 109.5 . . ?
C5A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 109.5 . . ?
C5A C6A H6A3 109.5 . . ?
H6A1 C6A H6A3 109.5 . . ?
H6A2 C6A H6A3 109.5 . . ?
C12 C7 C8 115(3) . . ?
C12 C7 Hg 124(3) . . ?
C8 C7 Hg 120(2) . . ?
C9 C8 C7 123(2) . . ?
C9 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
C10 C9 C8 118(2) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C11 C10 C9 121(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 122(2) . . ?
C7 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C12A C7A C8A 122(3) . . ?
C12A C7A Hg 120(3) . . ?
C8A C7A Hg 117(3) . . ?
C7A C8A C9A 118(2) . . ?
C7A C8A H8A 120.9 . . ?
C9A C8A H8A 120.9 . . ?
C8A C9A C10A 116(2) . . ?
C8A C9A H9A 122.2 . . ?
C10A C9A H9A 122.2 . . ?
C11A C10A C9A 123(3) . . ?
C11A C10A H10A 118.4 . . ?
C9A C10A H10A 118.4 . . ?
C10A C11A C12A 121(3) . . ?
C10A C11A H11A 119.7 . . ?
C12A C11A H11A 119.7 . . ?
C7A C12A C11A 120(3) . . ?
C7A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Hg S1 C1 C4 -179.6(8) . . . . ?
Hg S1 C1 C2 -0.3(6) . . . . ?
C4 C1 C2 O1 -179.4(8) . . . . ?
S1 C1 C2 O1 1.1(12) . . . . ?
C4 C1 C2 C3 -0.4(5) . . . . ?
S1 C1 C2 C3 -180.0(6) . . . . ?
O1 C2 C3 O2 -1.6(15) . . . . ?
C1 C2 C3 O2 179.5(8) . . . . ?
O1 C2 C3 C4 179.3(9) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C1 C4 O3 179.6(8) . . . . ?
S1 C1 C4 O3 -1.0(15) . . . . ?
C2 C1 C4 C3 0.5(6) . . . . ?
S1 C1 C4 C3 179.9(7) . . . . ?
O2 C3 C4 O3 1.4(15) . . . . ?
C2 C3 C4 O3 -179.6(8) . . . . ?
O2 C3 C4 C1 -179.5(9) . . . . ?
C2 C3 C4 C1 -0.5(6) . . . . ?
C1 C4 O3 C5 179.0(15) . . . . ?
C3 C4 O3 C5 -2.2(17) . . . . ?
C1 C4 O3 C5A 2.4(17) . . . . ?
C3 C4 O3 C5A -178.8(13) . . . . ?
C4 O3 C5 C6 176(4) . . . . ?
C4 O3 C5A C6A -178.5(18) . . . . ?
C12 C7 C8 C9 2(4) . . . . ?
Hg C7 C8 C9 177.2(19) . . . . ?
C7 C8 C9 C10 1(4) . . . . ?
C8 C9 C10 C11 -3(4) . . . . ?
C9 C10 C11 C12 2(4) . . . . ?
C8 C7 C12 C11 -4(4) . . . . ?
Hg C7 C12 C11 -179(2) . . . . ?
C10 C11 C12 C7 2(4) . . . . ?
C12A C7A C8A C9A -8(5) . . . . ?
Hg C7A C8A C9A 179(2) . . . . ?
C7A C8A C9A C10A 5(4) . . . . ?
C8A C9A C10A C11A -1(4) . . . . ?
C9A C10A C11A C12A -1(5) . . . . ?
C8A C7A C12A C11A 7(5) . . . . ?
Hg C7A C12A C11A 180(2) . . . . ?
C10A C11A C12A C7A -2(4) . . . . ?

_refine_diff_density_max         1.179
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.185



