# Supplementary Information (SI) for Chemical Science.
# 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_CS1JBG1250
_database_code_depnum_ccdc_archive 'CCDC 2418247'
loop_
_audit_author_name
_audit_author_address
'Guillermo Zaragoza'
;Universidade de Santiago de Compostela
Spain
;
_audit_update_record             
;
2025-01-20 deposited with the CCDC.	2025-05-08 downloaded from the CCDC.
;

_audit_creation_date             2022-11-28T08:58:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C16  H12'
_chemical_formula_sum            'C16 H12'
_chemical_formula_weight         204.26
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.4618(2)
_cell_length_b                   7.8144(2)
_cell_length_c                   22.3901(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1130.59(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    7525
_cell_measurement_theta_min      6.00
_cell_measurement_theta_max      74.55
_cell_measurement_wavelength     1.54178

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.2
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS-2016/2'
_exptl_absorpt_correction_T_min  0.8677
_exptl_absorpt_correction_T_max  0.9582
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.975

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'Incoatec multilayer mirror'
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_number            13018
_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       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         5.998
_diffrn_reflns_theta_max         69.974
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_coverage         0.678
_reflns_number_total             2140
_reflns_number_gt                1976
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APPEX3v2022.1-1 (BRUKER AXS, 2021)'
_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, 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2019/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+0.0954P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2140
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.035
_refine_ls_R_factor_gt           0.031
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 776 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(7)
_refine_diff_density_max         0.077
_refine_diff_density_min         -0.089
_refine_diff_density_rms         0.024

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.5066(3) 0.5622(2) 0.51772(8) 0.0513(4) Uani 1 1 d . . . . .
C2 C 0.5886(4) 0.6521(2) 0.56738(9) 0.0640(5) Uani 1 1 d . . . . .
H2 H 0.718915 0.701993 0.564749 0.077 Uiso 1 1 calc R U . . .
C3 C 0.4777(4) 0.6660(3) 0.61893(9) 0.0754(6) Uani 1 1 d . . . . .
H3 H 0.532893 0.725293 0.651237 0.091 Uiso 1 1 calc R U . . .
C4 C 0.2813(4) 0.5918(3) 0.62358(9) 0.0770(7) Uani 1 1 d . . . . .
H4 H 0.20696 0.602373 0.658958 0.092 Uiso 1 1 calc R U . . .
C5 C 0.1982(4) 0.5045(2) 0.57702(9) 0.0684(5) Uani 1 1 d . . . . .
H5 H 0.067851 0.455328 0.580952 0.082 Uiso 1 1 calc R U . . .
C6 C 0.3072(3) 0.4872(2) 0.52261(7) 0.0520(4) Uani 1 1 d . . . . .
C7 C 0.2285(3) 0.3965(2) 0.47308(8) 0.0522(4) Uani 1 1 d . . . . .
H7 H 0.100589 0.343038 0.476681 0.063 Uiso 1 1 calc R U . . .
C8 C 0.3324(3) 0.3838(2) 0.41987(7) 0.0470(4) Uani 1 1 d . . . . .
C9 C 0.2336(3) 0.2842(2) 0.37156(9) 0.0578(5) Uani 1 1 d . . . . .
H9 H 0.190818 0.174368 0.381728 0.069 Uiso 1 1 calc R U . . .
C10 C 0.1981(3) 0.3314(3) 0.31533(9) 0.0645(5) Uani 1 1 d . . . . .
H10 H 0.125701 0.253016 0.292066 0.077 Uiso 1 1 calc R U . . .
C11 C 0.2575(3) 0.4892(3) 0.28553(8) 0.0693(5) Uani 1 1 d . . . . .
H11 H 0.15161 0.550853 0.267407 0.083 Uiso 1 1 calc R U . . .
C12 C 0.4453(3) 0.5543(3) 0.28140(9) 0.0700(6) Uani 1 1 d . . . . .
H12 H 0.458534 0.656506 0.260448 0.084 Uiso 1 1 calc R U . . .
C13 C 0.6323(3) 0.4823(3) 0.30629(9) 0.0646(5) Uani 1 1 d . . . . .
H13 H 0.740656 0.465385 0.279592 0.078 Uiso 1 1 calc R U . . .
C14 C 0.6689(3) 0.4376(3) 0.36222(9) 0.0593(5) Uani 1 1 d . . . . .
H14 H 0.796699 0.386687 0.369224 0.071 Uiso 1 1 calc R U . . .
C15 C 0.5341(2) 0.4573(2) 0.41527(7) 0.0482(4) Uani 1 1 d . . . . .
C16 C 0.6159(3) 0.5414(2) 0.46375(8) 0.0522(4) Uani 1 1 d . . . . .
H16 H 0.748749 0.586325 0.460819 0.063 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C16 1.409(2) . ?
C1 C2 1.418(3) . ?
C1 C6 1.419(3) . ?
C2 C3 1.363(3) . ?
C2 H2 0.93 . ?
C3 C4 1.399(3) . ?
C3 H3 0.93 . ?
C4 C5 1.357(3) . ?
C4 H4 0.93 . ?
C5 C6 1.414(3) . ?
C5 H5 0.93 . ?
C6 C7 1.411(2) . ?
C7 C8 1.371(2) . ?
C7 H7 0.93 . ?
C8 C15 1.428(2) . ?
C8 C9 1.478(2) . ?
C9 C10 1.332(3) . ?
C9 H9 0.93 . ?
C10 C11 1.454(3) . ?
C10 H10 0.93 . ?
C11 C12 1.319(3) . ?
C11 H11 0.93 . ?
C12 C13 1.445(3) . ?
C12 H12 0.93 . ?
C13 C14 1.321(3) . ?
C13 H13 0.93 . ?
C14 C15 1.481(2) . ?
C14 H14 0.93 . ?
C15 C16 1.375(2) . ?
C16 H16 0.93 . ?

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
C16 C1 C2 122.83(18) . . ?
C16 C1 C6 118.27(15) . . ?
C2 C1 C6 118.89(17) . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 123.09(17) . . ?
C7 C6 C1 118.26(15) . . ?
C5 C6 C1 118.64(17) . . ?
C8 C7 C6 122.90(15) . . ?
C8 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C7 C8 C15 118.71(15) . . ?
C7 C8 C9 117.58(15) . . ?
C15 C8 C9 123.58(15) . . ?
C10 C9 C8 128.36(17) . . ?
C10 C9 H9 115.8 . . ?
C8 C9 H9 115.8 . . ?
C9 C10 C11 128.55(18) . . ?
C9 C10 H10 115.7 . . ?
C11 C10 H10 115.7 . . ?
C12 C11 C10 127.05(19) . . ?
C12 C11 H11 116.5 . . ?
C10 C11 H11 116.5 . . ?
C11 C12 C13 126.31(19) . . ?
C11 C12 H12 116.8 . . ?
C13 C12 H12 116.8 . . ?
C14 C13 C12 128.17(18) . . ?
C14 C13 H13 115.9 . . ?
C12 C13 H13 115.9 . . ?
C13 C14 C15 128.86(18) . . ?
C13 C14 H14 115.6 . . ?
C15 C14 H14 115.6 . . ?
C16 C15 C8 119.09(15) . . ?
C16 C15 C14 117.19(15) . . ?
C8 C15 C14 123.57(15) . . ?
C15 C16 C1 122.65(16) . . ?
C15 C16 H16 118.7 . . ?
C1 C16 H16 118.7 . . ?

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
C16 C1 C2 C3 -178.88(17) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 179.43(18) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C16 C1 C6 C7 -0.3(2) . . . . ?
C2 C1 C6 C7 -179.33(16) . . . . ?
C16 C1 C6 C5 178.72(16) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C5 C6 C7 C8 178.27(16) . . . . ?
C1 C6 C7 C8 -2.7(2) . . . . ?
C6 C7 C8 C15 3.6(2) . . . . ?
C6 C7 C8 C9 179.63(15) . . . . ?
C7 C8 C9 C10 128.2(2) . . . . ?
C15 C8 C9 C10 -56.0(3) . . . . ?
C8 C9 C10 C11 4.0(3) . . . . ?
C9 C10 C11 C12 54.7(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C14 -54.2(3) . . . . ?
C12 C13 C14 C15 -3.8(4) . . . . ?
C7 C8 C15 C16 -1.4(2) . . . . ?
C9 C8 C15 C16 -177.14(16) . . . . ?
C7 C8 C15 C14 173.98(17) . . . . ?
C9 C8 C15 C14 -1.8(2) . . . . ?
C13 C14 C15 C16 -125.7(2) . . . . ?
C13 C14 C15 C8 58.9(3) . . . . ?
C8 C15 C16 C1 -1.7(2) . . . . ?
C14 C15 C16 C1 -177.30(16) . . . . ?
C2 C1 C16 C15 -178.54(16) . . . . ?
C6 C1 C16 C15 2.5(2) . . . . ?

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

data_cs1jbg1632
_database_code_depnum_ccdc_archive 'CCDC 2427818'
loop_
_audit_author_name
_audit_author_address
'Guillermo Zaragoza'
;Universidade de Santiago de Compostela
Spain
;
_audit_update_record             
;
2025-02-28 deposited with the CCDC.	2025-05-08 downloaded from the CCDC.
;

_audit_creation_date             2025-02-10T15:53:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C24 H18'
_chemical_formula_sum            'C24 H18'
_chemical_formula_weight         306.38

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4244(4)
_cell_length_b                   9.6598(5)
_cell_length_c                   10.1931(5)
_cell_angle_alpha                75.257(5)
_cell_angle_beta                 82.012(4)
_cell_angle_gamma                67.210(4)
_cell_volume                     826.50(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12103
_cell_measurement_theta_min      4.47
_cell_measurement_theta_max      72.19
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.984

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.06213
_diffrn_orient_matrix_ub_12      0.060943
_diffrn_orient_matrix_ub_13      -0.143883
_diffrn_orient_matrix_ub_21      -0.010228
_diffrn_orient_matrix_ub_22      0.162324
_diffrn_orient_matrix_ub_23      0.002554
_diffrn_orient_matrix_ub_31      0.165947
_diffrn_orient_matrix_ub_32      -0.036894
_diffrn_orient_matrix_ub_33      -0.061337
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_number            38184
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.49
_diffrn_reflns_theta_max         70.076
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             3107
_reflns_number_gt                2581
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.44.92a (Rigaku OD, 2025)'
_computing_cell_refinement       'CrysAlisPro 1.171.44.92a (Rigaku OD, 2025)'
_computing_data_reduction        'CrysAlisPro 1.171.44.92a (Rigaku OD, 2025)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2019/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+0.2596P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3107
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C -0.09339(16) 0.74040(15) 0.75016(14) 0.0246(3) Uani 1 1 d . . . . .
C2 C 0.06014(16) 0.72578(15) 0.71005(14) 0.0231(3) Uani 1 1 d . . . . .
C3 C 0.16292(15) 0.70233(15) 0.80665(14) 0.0222(3) Uani 1 1 d . . . . .
C4 C 0.11282(15) 0.69255(15) 0.94535(13) 0.0223(3) Uani 1 1 d . . . . .
C5 C -0.03723(16) 0.70117(15) 0.98554(14) 0.0227(3) Uani 1 1 d . . . . .
C6 C -0.14268(16) 0.72808(15) 0.88689(14) 0.0236(3) Uani 1 1 d . . . . .
C7 C -0.30282(17) 0.74113(17) 0.93312(15) 0.0298(3) Uani 1 1 d . . . . .
H7 H -0.315161 0.655561 0.997263 0.036 Uiso 1 1 calc R U . . .
C8 C -0.43136(17) 0.86111(19) 0.89362(16) 0.0339(4) Uani 1 1 d . . . . .
H8 H -0.525135 0.853923 0.936632 0.041 Uiso 1 1 calc R U . . .
C9 C -0.44433(17) 1.00236(19) 0.79169(17) 0.0350(4) Uani 1 1 d . . . . .
H9 H -0.493196 1.096665 0.82058 0.042 Uiso 1 1 calc R U . . .
C10 C -0.39416(17) 1.01114(19) 0.66240(17) 0.0364(4) Uani 1 1 d . . . . .
H10 H -0.407835 1.110215 0.606798 0.044 Uiso 1 1 calc R U . . .
C11 C -0.31882(18) 0.8772(2) 0.60000(17) 0.0376(4) Uani 1 1 d . . . . .
H11 H -0.364175 0.87699 0.522481 0.045 Uiso 1 1 calc R U . . .
C12 C -0.19352(17) 0.75701(18) 0.64213(15) 0.0317(3) Uani 1 1 d . . . . .
H12 H -0.164718 0.673 0.599063 0.038 Uiso 1 1 calc R U . . .
C13 C 0.10393(17) 0.74132(17) 0.56227(14) 0.0294(3) Uani 1 1 d . . . . .
H13 H 0.052731 0.837675 0.50397 0.035 Uiso 1 1 calc R U . . .
C14 C 0.20812(17) 0.63259(18) 0.50466(14) 0.0307(3) Uani 1 1 d . . . . .
H14 H 0.21592 0.654619 0.408227 0.037 Uiso 1 1 calc R U . . .
C15 C 0.31175(17) 0.48280(17) 0.57462(14) 0.0287(3) Uani 1 1 d . . . . .
H15 H 0.308842 0.394119 0.552623 0.034 Uiso 1 1 calc R U . . .
C16 C 0.40989(17) 0.46057(17) 0.66668(15) 0.0289(3) Uani 1 1 d . . . . .
H16 H 0.470839 0.357164 0.705652 0.035 Uiso 1 1 calc R U . . .
C17 C 0.43194(16) 0.58239(17) 0.71315(14) 0.0284(3) Uani 1 1 d . . . . .
H17 H 0.533078 0.584056 0.702105 0.034 Uiso 1 1 calc R U . . .
C18 C 0.32492(16) 0.69031(17) 0.76897(14) 0.0264(3) Uani 1 1 d . . . . .
H18 H 0.354369 0.767214 0.786578 0.032 Uiso 1 1 calc R U . . .
C19 C 0.22798(16) 0.66958(17) 1.04237(14) 0.0262(3) Uani 1 1 d . . . . .
H19 H 0.320057 0.581301 1.044927 0.031 Uiso 1 1 calc R U . . .
C20 C 0.21583(17) 0.75976(17) 1.12630(14) 0.0286(3) Uani 1 1 d . . . . .
H20 H 0.305914 0.734967 1.173095 0.034 Uiso 1 1 calc R U . . .
C21 C 0.08264(18) 0.89184(17) 1.15629(14) 0.0302(3) Uani 1 1 d . . . . .
H21 H 0.096937 0.986454 1.144368 0.036 Uiso 1 1 calc R U . . .
C22 C -0.05679(19) 0.88983(17) 1.19889(14) 0.0308(3) Uani 1 1 d . . . . .
H22 H -0.133408 0.982628 1.216649 0.037 Uiso 1 1 calc R U . . .
C23 C -0.10162(17) 0.75645(17) 1.22059(14) 0.0296(3) Uani 1 1 d . . . . .
H23 H -0.144076 0.726139 1.308254 0.036 Uiso 1 1 calc R U . . .
C24 C -0.08961(16) 0.67305(16) 1.13149(14) 0.0265(3) Uani 1 1 d . . . . .
H24 H -0.117566 0.585398 1.164395 0.032 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C6 1.3967(19) . ?
C1 C2 1.410(2) . ?
C1 C12 1.4868(19) . ?
C2 C3 1.3931(19) . ?
C2 C13 1.4907(19) . ?
C3 C4 1.4183(18) . ?
C3 C18 1.4881(19) . ?
C4 C5 1.3927(19) . ?
C4 C19 1.4851(19) . ?
C5 C6 1.4181(19) . ?
C5 C24 1.4915(19) . ?
C6 C7 1.484(2) . ?
C7 C8 1.335(2) . ?
C8 C9 1.463(2) . ?
C9 C10 1.330(2) . ?
C10 C11 1.471(2) . ?
C11 C12 1.324(2) . ?
C13 C14 1.329(2) . ?
C14 C15 1.459(2) . ?
C15 C16 1.329(2) . ?
C16 C17 1.467(2) . ?
C17 C18 1.325(2) . ?
C19 C20 1.334(2) . ?
C20 C21 1.466(2) . ?
C21 C22 1.331(2) . ?
C22 C23 1.462(2) . ?
C23 C24 1.327(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
C6 C1 C2 120.44(12) . . ?
C6 C1 C12 122.71(13) . . ?
C2 C1 C12 116.68(12) . . ?
C3 C2 C1 120.01(12) . . ?
C3 C2 C13 122.61(12) . . ?
C1 C2 C13 117.36(12) . . ?
C2 C3 C4 119.82(12) . . ?
C2 C3 C18 122.04(12) . . ?
C4 C3 C18 118.13(12) . . ?
C5 C4 C3 120.11(12) . . ?
C5 C4 C19 122.99(12) . . ?
C3 C4 C19 116.88(12) . . ?
C4 C5 C6 119.99(12) . . ?
C4 C5 C24 122.00(12) . . ?
C6 C5 C24 117.90(12) . . ?
C1 C6 C5 119.54(12) . . ?
C1 C6 C7 121.98(13) . . ?
C5 C6 C7 118.47(12) . . ?
C8 C7 C6 126.52(14) . . ?
C7 C8 C9 127.46(14) . . ?
C10 C9 C8 126.12(15) . . ?
C9 C10 C11 124.18(16) . . ?
C12 C11 C10 125.87(14) . . ?
C11 C12 C1 126.47(14) . . ?
C14 C13 C2 125.92(13) . . ?
C13 C14 C15 126.56(13) . . ?
C16 C15 C14 125.19(14) . . ?
C15 C16 C17 125.46(14) . . ?
C18 C17 C16 126.52(13) . . ?
C17 C18 C3 126.10(13) . . ?
C20 C19 C4 126.89(13) . . ?
C19 C20 C21 128.92(13) . . ?
C22 C21 C20 125.22(13) . . ?
C21 C22 C23 125.33(14) . . ?
C24 C23 C22 127.24(13) . . ?
C23 C24 C5 127.43(13) . . ?

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
C6 C1 C2 C3 -1.4(2) . . . . ?
C12 C1 C2 C3 -176.91(12) . . . . ?
C6 C1 C2 C13 -179.61(12) . . . . ?
C12 C1 C2 C13 4.94(18) . . . . ?
C1 C2 C3 C4 0.28(19) . . . . ?
C13 C2 C3 C4 178.34(12) . . . . ?
C1 C2 C3 C18 -178.36(12) . . . . ?
C13 C2 C3 C18 -0.3(2) . . . . ?
C2 C3 C4 C5 2.15(19) . . . . ?
C18 C3 C4 C5 -179.15(12) . . . . ?
C2 C3 C4 C19 -179.19(12) . . . . ?
C18 C3 C4 C19 -0.50(18) . . . . ?
C3 C4 C5 C6 -3.41(19) . . . . ?
C19 C4 C5 C6 178.03(12) . . . . ?
C3 C4 C5 C24 172.65(12) . . . . ?
C19 C4 C5 C24 -5.9(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C12 C1 C6 C5 175.38(12) . . . . ?
C2 C1 C6 C7 -179.33(12) . . . . ?
C12 C1 C6 C7 -4.1(2) . . . . ?
C4 C5 C6 C1 2.23(19) . . . . ?
C24 C5 C6 C1 -173.98(12) . . . . ?
C4 C5 C6 C7 -178.22(12) . . . . ?
C24 C5 C6 C7 5.56(18) . . . . ?
C1 C6 C7 C8 -58.6(2) . . . . ?
C5 C6 C7 C8 121.87(16) . . . . ?
C6 C7 C8 C9 3.4(2) . . . . ?
C7 C8 C9 C10 57.6(2) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C9 C10 C11 C12 -56.7(3) . . . . ?
C10 C11 C12 C1 -7.5(3) . . . . ?
C6 C1 C12 C11 67.7(2) . . . . ?
C2 C1 C12 C11 -116.97(18) . . . . ?
C3 C2 C13 C14 64.6(2) . . . . ?
C1 C2 C13 C14 -117.31(17) . . . . ?
C2 C13 C14 C15 -7.0(3) . . . . ?
C13 C14 C15 C16 -56.0(2) . . . . ?
C14 C15 C16 C17 -0.5(2) . . . . ?
C15 C16 C17 C18 57.8(2) . . . . ?
C16 C17 C18 C3 5.5(2) . . . . ?
C2 C3 C18 C17 -63.2(2) . . . . ?
C4 C3 C18 C17 118.17(16) . . . . ?
C5 C4 C19 C20 -58.8(2) . . . . ?
C3 C4 C19 C20 122.60(16) . . . . ?
C4 C19 C20 C21 7.7(2) . . . . ?
C19 C20 C21 C22 54.7(2) . . . . ?
C20 C21 C22 C23 -1.2(2) . . . . ?
C21 C22 C23 C24 -55.6(2) . . . . ?
C22 C23 C24 C5 -4.3(3) . . . . ?
C4 C5 C24 C23 65.2(2) . . . . ?
C6 C5 C24 C23 -118.68(17) . . . . ?

