# Supplementary Information (SI) for Chemical Communications.
# 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_drr_ligand_0m
_database_code_depnum_ccdc_archive 'CCDC 2359798'
loop_
_audit_author_name
_audit_author_address
'Sheridon N. Kelly'
;UC Berkeley
United States of America
;
_audit_update_record             
;
2024-05-31 deposited with the CCDC.	2024-12-19 downloaded from the CCDC.
;
_audit_creation_date             2024-04-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            hdcCOT
_chemical_name_systematic        
(4Z,9Z)-1,2,3,6,7,8-hexahydrodicyclopenta[a,e][8]annulene
_chemical_formula_moiety         'C14 H16'
_chemical_formula_sum            'C14 H16'
_chemical_formula_weight         184.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.6889(8)
_cell_length_b                   21.463(3)
_cell_length_c                   7.9961(11)
_cell_angle_alpha                90
_cell_angle_beta                 113.643(5)
_cell_angle_gamma                90
_cell_volume                     1051.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15072
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.197
_cell_measurement_theta_min      3.013
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.997
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0911 before and 0.0776 after correction.
The Ratio of minimum to maximum transmission is 0.8333.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15072
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.930
_diffrn_reflns_theta_max         27.197
_diffrn_reflns_theta_min         3.013
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source, station 12.2.1'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON-II CPAD detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1755
_reflns_number_total             2164
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A Bruker, Madison WI'
_computing_data_collection       'Bruker APEX3 Bruker, Madison WI'
_computing_data_reduction        'SAINT V8.38A Bruker, Madison WI'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+0.2864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1215
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C10(H10A,H10B)
1.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C3(H3), C7(H7), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
C2 C 0.3212(2) 0.59213(6) 0.36992(19) 0.0201(3) Uani 1 1 d . . . . .
C8 C 0.7178(2) 0.57690(6) 0.5745(2) 0.0223(3) Uani 1 1 d . . . . .
H8 H 0.798781 0.539422 0.613571 0.027 Uiso 1 1 calc R U . . .
C1 C 0.5247(2) 0.57413(6) 0.40180(19) 0.0203(3) Uani 1 1 d . . . . .
C3 C 0.2373(2) 0.61521(6) 0.50250(19) 0.0218(3) Uani 1 1 d . . . . .
H3 H 0.115632 0.593616 0.507188 0.026 Uiso 1 1 calc R U . . .
C6 C 0.6964(2) 0.68910(6) 0.65605(18) 0.0202(3) Uani 1 1 d . . . . .
C7 C 0.7918(2) 0.62623(7) 0.68241(19) 0.0223(3) Uani 1 1 d . . . . .
H7 H 0.921448 0.620165 0.788994 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4923(2) 0