# 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. 
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data_toy2127_hexane_xray_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2l6tzm
_database_code_depnum_ccdc_archive 'CCDC 2389851'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2025-np2hv 2025
loop_
_audit_author_name
_audit_author_address
'Hideto Ito'
;Nagoya University
Japan
;
_audit_update_record             
;
2024-10-10 deposited with the CCDC.	2025-04-11 downloaded from the CCDC.
;
_audit_creation_date             2024-09-07
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        7k
_chemical_formula_moiety         'C24 H26'
_chemical_formula_sum            'C24 H26'
_chemical_formula_weight         314.4694
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7615(3)
_cell_length_b                   10.5013(3)
_cell_length_c                   17.8315(6)
_cell_angle_alpha                84.768(3)
_cell_angle_beta                 83.360(3)
_cell_angle_gamma                85.557(3)
_cell_volume                     1619.11(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9394
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.1090
_cell_measurement_theta_min      2.1850
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22243
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.807
_diffrn_reflns_theta_min         1.952
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  32.00   0.50    1.50    --    3.48 -99.00 -30.00   86
  2  ω      1.00  38.00   0.50    1.50    --    3.48 -99.00-120.00   74
  3  ω      8.00  38.00   0.50    1.50    --    3.48 -99.00-180.00   60
  4  ω     37.00  70.00   0.50    1.50    --   -2.85  57.00-120.00   66
  5  ω    -19.00  23.00   0.50    1.50    --   -2.85  57.00-120.00   84
  6  ω    -15.00  29.00   0.50    1.50    --   -2.85  57.00  30.00   88
  7  ω     42.00  68.00   0.50    1.50    --   -2.85  57.00  30.00   52
  8  ω     -2.00  73.00   0.50    1.50    --   -2.85  37.00 -30.00  150
  9  ω    -61.00 -28.00   0.50    1.50    --   -2.85 -77.00  30.00   66
 10  ω    -13.00  19.00   0.50    1.50    --   -2.85 -77.00  30.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0047078000
_diffrn_orient_matrix_UB_12      -0.0519111000
_diffrn_orient_matrix_UB_13      0.0282036000
_diffrn_orient_matrix_UB_21      0.0126543000
_diffrn_orient_matrix_UB_22      -0.0435846000
_diffrn_orient_matrix_UB_23      -0.0285799000
_diffrn_orient_matrix_UB_31      0.0805671000
_diffrn_orient_matrix_UB_32      0.0052152000
_diffrn_orient_matrix_UB_33      -0.0016147000
_diffrn_oxdiff_digest_frames     
;
012e3598fe0f2579736dcf657163f845890002612f4
;
_diffrn_oxdiff_digest_hkl        
;
01e9136d1680d3fe34e775bce4a27948eb10ff
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6208
_reflns_number_total             7678
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7678
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.103
_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)+(0.0692P)²+0.2305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1334
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C40(H00H), C22(H00F), C37(H00K), C19(H00M), C16(H00N), C43(H00O), C46(H00Q),
 C13(H00R)
2.b Secondary CH2 refined with riding coordinates:
 C15(H00A,H00B), C36(H00L,H00P), C48(H00S,H00T), C35(H00V,H00W), C38(H00Y,H),
 C17(H00C,H00D), C11(H00E,H00G), C14(H01A,H01B), C41(H01O,H01P), C47(H01Q,H01R),
  C20(H01C,H01D), C42(H01S,H01T), C24(H01E,H01F), C12(H01G,H01H), C44(H01U,
 H01V), C39(H01W,H01X), C45(H01Y,HA), C21(H01I,H01J), C23(H01K,H01L), C18(H01M,
 H01N)
2.c Aromatic/amide H refined with riding coordinates:
 C30(H00I), C29(H00J), C6(H00U), C5(H00X)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C32 C 0.22874(11) 0.50597(10) 0.07650(6) 0.0133(2) Uani 1 1 d . . . . .
C10 C 0.33019(11) 0.02846(9) 0.44557(6) 0.0134(2) Uani 1 1 d . . . . .
C9 C 0.26126(11) -0.03404(9) 0.51048(6) 0.0134(2) Uani 1 1 d . . . . .
C8 C 0.22527(11) 0.03255(10) 0.57735(6) 0.0138(2) Uani 1 1 d . . . . .
C33 C 0.26641(11) 0.46106(9) 0.00275(6) 0.0132(2) Uani 1 1 d . . . . .
C34 C 0.32874(11) 0.54231(10) -0.05570(6) 0.0138(2) Uani 1 1 d . . . . .
C26 C 0.30752(11) 0.72021(10) 0.02477(6) 0.0142(2) Uani 1 1 d . . . . .
C31 C 0.16779(12) 0.42369(10) 0.13911(6) 0.0152(2) Uani 1 1 d . . . . .
C1 C 0.35853(11) 0.16102(10) 0.44314(6) 0.0140(2) Uani 1 1 d . . . . .
C7 C 0.16009(12) -0.03119(10) 0.64665(6) 0.0157(2) Uani 1 1 d . . . . .
C25 C 0.34835(11) 0.67298(10) -0.04477(6) 0.0142(2) Uani 1 1 d . . . . .
C2 C 0.31785(12) 0.22919(9) 0.50577(6) 0.0139(2) Uani 1 1 d . . . . .
C40 C 0.36900(12) 0.50508(10) -0.13613(6) 0.0163(2) Uani 1 1 d . . . . .
H00H H 0.481039 0.516831 -0.150644 0.020 Uiso 1 1 calc R . . . .
C30 C 0.13377(12) 0.47006(11) 0.20914(6) 0.0184(2) Uani 1 1 d . . . . .
H00I H 0.094048 0.414843 0.250816 0.022 Uiso 1 1 calc R . . . .
C22 C 0.33579(12) 0.37285(10) 0.50104(6) 0.0173(2) Uani 1 1 d . . . . .
H00F H 0.442086 0.385429 0.512958 0.021 Uiso 1 1 calc R . . . .
C3 C 0.25409(11) 0.16506(10) 0.57509(6) 0.0141(2) Uani 1 1 d . . . . .
C28 C 0.21194(12) 0.68069(10) 0.16110(6) 0.0163(2) Uani 1 1 d . . . . .
C29 C 0.15670(13) 0.59788(11) 0.22026(6) 0.0192(2) Uani 1 1 d . . . . .
H00J H 0.133610 0.627235 0.269408 0.023 Uiso 1 1 calc R . . . .
C37 C 0.23139(12) 0.32576(10) -0.01044(6) 0.0151(2) Uani 1 1 d . . . . .
H00K H 0.324769 0.267975 -0.001296 0.018 Uiso 1 1 calc R . . . .
C15 C 0.33570(13) -0.17549(10) 0.37779(6) 0.0189(2) Uani 1 1 d . . . . .
H00A H 0.321456 -0.199496 0.326759 0.023 Uiso 1 1 calc R . . . .
H00B H 0.422835 -0.230565 0.396198 0.023 Uiso 1 1 calc R . . . .
C27 C 0.25026(11) 0.63631(10) 0.08756(6) 0.0137(2) Uani 1 1 d . . . . .
C19 C 0.42252(12) 0.22129(10) 0.36682(6) 0.0163(2) Uani 1 1 d . . . . .
H00M H 0.526694 0.178280 0.353351 0.020 Uiso 1 1 calc R . . . .
C16 C 0.37451(12) -0.03455(10) 0.37230(6) 0.0161(2) Uani 1 1 d . . . . .
H00N H 0.488702 -0.032556 0.360335 0.019 Uiso 1 1 calc R . . . .
C43 C 0.40619(12) 0.75477(10) -0.11504(6) 0.0170(2) Uani 1 1 d . . . . .
H00O H 0.511699 0.718617 -0.132925 0.020 Uiso 1 1 calc R . . . .
C4 C 0.21751(12) 0.23097(10) 0.64214(6) 0.0174(2) Uani 1 1 d . . . . .
C46 C 0.31698(12) 0.86186(10) 0.03465(6) 0.0174(2) Uani 1 1 d . . . . .
H00Q H 0.422635 0.873245 0.047911 0.021 Uiso 1 1 calc R . . . .
C13 C 0.21698(12) -0.17145(10) 0.51109(6) 0.0155(2) Uani 1 1 d . . . . .
H00R H 0.306365 -0.229340 0.526140 0.019 Uiso 1 1 calc R . . . .
C36 C 0.09839(12) 0.27990(10) 0.04597(6) 0.0177(2) Uani 1 1 d . . . . .
H00L H 0.080181 0.190361 0.038302 0.021 Uiso 1 1 calc R . . . .
H00P H 0.003212 0.334080 0.037762 0.021 Uiso 1 1 calc R . . . .
C48 C 0.22989(13) 0.81934(10) 0.17195(7) 0.0201(2) Uani 1 1 d . . . . .
H00S H 0.335034 0.828956 0.184907 0.024 Uiso 1 1 calc R . . . .
H00T H 0.155480 0.846798 0.214490 0.024 Uiso 1 1 calc R . . . .
C6 C 0.13065(13) 0.03498(11) 0.71026(6) 0.0198(2) Uani 1 1 d . . . . .
H00U H 0.090426 -0.008137 0.756648 0.024 Uiso 1 1 calc R . . . .
C35 C 0.13772(12) 0.28779(10) 0.12655(6) 0.0172(2) Uani 1 1 d . . . . .
H00V H 0.051238 0.258670 0.163228 0.021 Uiso 1 1 calc R . . . .
H00W H 0.230194 0.230420 0.135290 0.021 Uiso 1 1 calc R . . . .
C38 C 0.20251(13) 0.31961(10) -0.09286(6) 0.0190(2) Uani 1 1 d . . . . .
H00Y H 0.184924 0.230545 -0.101890 0.023 Uiso 1 1 calc R . . . .
H H 0.109495 0.374814 -0.103666 0.023 Uiso 1 1 calc R . . . .
C5 C 0.15892(13) 0.16560(11) 0.70808(6) 0.0203(2) Uani 1 1 d . . . . .
H00X H 0.137122 0.209111 0.752930 0.024 Uiso 1 1 calc R . . . .
C17 C 0.30002(13) 0.04600(11) 0.30768(6) 0.0199(2) Uani 1 1 d . . . . .
H00C H 0.347900 0.017095 0.258523 0.024 Uiso 1 1 calc R . . . .
H00D H 0.189100 0.030774 0.312202 0.024 Uiso 1 1 calc R . . . .
C11 C 0.12070(12) -0.16899(10) 0.64766(6) 0.0185(2) Uani 1 1 d . . . . .
H00E H 0.032327 -0.185455 0.686312 0.022 Uiso 1 1 calc R . . . .
H00G H 0.209635 -0.226785 0.661474 0.022 Uiso 1 1 calc R . . . .
C14 C 0.19012(12) -0.19901(10) 0.43115(6) 0.0187(2) Uani 1 1 d . . . . .
H01A H 0.164159 -0.289066 0.430995 0.022 Uiso 1 1 calc R . . . .
H01B H 0.102952 -0.142416 0.414035 0.022 Uiso 1 1 calc R . . . .
C41 C 0.27764(13) 0.59998(11) -0.18815(6) 0.0197(2) Uani 1 1 d . . . . .
H01O H 0.166643 0.585512 -0.177385 0.024 Uiso 1 1 calc R . . . .
H01P H 0.310233 0.583365 -0.241600 0.024 Uiso 1 1 calc R . . . .
C47 C 0.20221(13) 0.90400(10) 0.10017(7) 0.0207(2) Uani 1 1 d . . . . .
H01Q H 0.214613 0.994574 0.108036 0.025 Uiso 1 1 calc R . . . .
H01R H 0.095814 0.897151 0.088100 0.025 Uiso 1 1 calc R . . . .
C20 C 0.44105(13) 0.36571(10) 0.36507(7) 0.0205(2) Uani 1 1 d . . . . .
H01C H 0.545314 0.379318 0.377768 0.025 Uiso 1 1 calc R . . . .
H01D H 0.431478 0.405551 0.313184 0.025 Uiso 1 1 calc R . . . .
C42 C 0.30179(13) 0.74106(11) -0.17728(6) 0.0207(2) Uani 1 1 d . . . . .
H01S H 0.348126 0.782632 -0.225761 0.025 Uiso 1 1 calc R . . . .
H01T H 0.200354 0.786581 -0.164069 0.025 Uiso 1 1 calc R . . . .
C24 C 0.24141(14) 0.37261(10) 0.63876(7) 0.0215(2) Uani 1 1 d . . . . .
H01E H 0.345996 0.384410 0.651708 0.026 Uiso 1 1 calc R . . . .
H01F H 0.165848 0.413483 0.676463 0.026 Uiso 1 1 calc R . . . .
C12 C 0.08007(12) -0.19694(10) 0.57010(6) 0.0181(2) Uani 1 1 d . . . . .
H01G H 0.054860 -0.287428 0.571278 0.022 Uiso 1 1 calc R . . . .
H01H H -0.011101 -0.141461 0.556815 0.022 Uiso 1 1 calc R . . . .
C44 C 0.41909(13) 0.89577(11) -0.10161(7) 0.0218(2) Uani 1 1 d . . . . .
H01U H 0.522633 0.906316 -0.086894 0.026 Uiso 1 1 calc R . . . .
H01V H 0.407485 0.949757 -0.149374 0.026 Uiso 1 1 calc R . . . .
C39 C 0.34164(13) 0.36491(11) -0.14496(6) 0.0204(2) Uani 1 1 d . . . . .
H01W H 0.325427 0.355764 -0.198183 0.024 Uiso 1 1 calc R . . . .
H01X H 0.434292 0.309938 -0.133282 0.024 Uiso 1 1 calc R . . . .
C45 C 0.29749(13) 0.94113(10) -0.04002(7) 0.0212(2) Uani 1 1 d . . . . .
H01Y H 0.193551 0.932297 -0.054779 0.025 Uiso 1 1 calc R . . . .
HA H 0.307613 1.032731 -0.033854 0.025 Uiso 1 1 calc R . . . .
C21 C 0.32155(13) 0.43098(10) 0.42040(7) 0.0209(2) Uani 1 1 d . . . . .
H01I H 0.217036 0.420412 0.406922 0.025 Uiso 1 1 calc R . . . .
H01J H 0.336788 0.523838 0.417136 0.025 Uiso 1 1 calc R . . . .
C23 C 0.22224(13) 0.43687(10) 0.55991(7) 0.0215(2) Uani 1 1 d . . . . .
H01K H 0.240726 0.528935 0.558396 0.026 Uiso 1 1 calc R . . . .
H01L H 0.115647 0.430002 0.548136 0.026 Uiso 1 1 calc R . . . .
C18 C 0.31753(13) 0.19081(11) 0.30820(6) 0.0193(2) Uani 1 1 d . . . . .
H01M H 0.360754 0.224705 0.257170 0.023 Uiso 1 1 calc R . . . .
H01N H 0.214522 0.234932 0.319517 0.023 Uiso 1 1 calc R . . . .


_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
C32 C33 1.4315(15) . ?
C32 C31 1.4270(14) . ?
C32 C27 1.4303(13) . ?
C10 C9 1.3770(15) . ?
C10 C1 1.4287(13) . ?
C10 C16 1.5153(14) . ?
C9 C8 1.4287(15) . ?
C9 C13 1.5217(13) . ?
C8 C7 1.4305(15) . ?
C8 C3 1.4295(14) . ?
C33 C34 1.3751(15) . ?
C33 C37 1.5210(13) . ?
C34 C25 1.4295(14) . ?
C34 C40 1.5160(14) . ?
C26 C25 1.3762(15) . ?
C26 C27 1.4282(14) . ?
C26 C46 1.5234(13) . ?
C31 C30 1.3739(15) . ?
C31 C35 1.5121(14) . ?
C1 C2 1.3788(15) . ?
C1 C19 1.5127(15) . ?
C7 C6 1.3727(16) . ?
C7 C11 1.5115(14) . ?
C25 C43 1.5129(14) . ?
C2 C22 1.5226(13) . ?
C2 C3 1.4284(15) . ?
C40 C41 1.5406(14) . ?
C40 C39 1.5345(14) . ?
C30 C29 1.4074(15) . ?
C22 C21 1.5248(15) . ?
C22 C23 1.5256(16) . ?
C3 C4 1.4279(15) . ?
C28 C29 1.3723(15) . ?
C28 C27 1.4265(15) . ?
C28 C48 1.5086(14) . ?
C37 C36 1.5261(15) . ?
C37 C38 1.5277(15) . ?
C15 C16 1.5361(14) . ?
C15 C14 1.5226(16) . ?
C19 C20 1.5348(14) . ?
C19 C18 1.5397(14) . ?
C16 C17 1.5428(14) . ?
C43 C42 1.5406(15) . ?
C43 C44 1.5361(14) . ?
C4 C5 1.3731(16) . ?
C4 C24 1.5129(14) . ?
C46 C47 1.5250(16) . ?
C46 C45 1.5242(15) . ?
C13 C14 1.5278(15) . ?
C13 C12 1.5245(15) . ?
C36 C35 1.5267(15) . ?
C48 C47 1.5226(16) . ?
C6 C5 1.4090(15) . ?
C38 C39 1.5240(16) . ?
C17 C18 1.5412(15) . ?
C11 C12 1.5262(15) . ?
C41 C42 1.5452(15) . ?
C20 C21 1.5208(16) . ?
C24 C23 1.5246(16) . ?
C44 C45 1.5213(17) . ?

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
C31 C32 C33 121.26(9) . . ?
C31 C32 C27 119.23(9) . . ?
C27 C32 C33 119.50(9) . . ?
C9 C10 C1 120.75(9) . . ?
C9 C10 C16 123.43(9) . . ?
C1 C10 C16 115.78(9) . . ?
C10 C9 C8 119.60(9) . . ?
C10 C9 C13 120.88(9) . . ?
C8 C9 C13 119.47(9) . . ?
C9 C8 C7 121.01(9) . . ?
C9 C8 C3 119.65(9) . . ?
C3 C8 C7 119.34(9) . . ?
C32 C33 C37 119.47(9) . . ?
C34 C33 C32 119.52(9) . . ?
C34 C33 C37 120.97(9) . . ?
C33 C34 C25 120.83(9) . . ?
C33 C34 C40 123.59(9) . . ?
C25 C34 C40 115.41(9) . . ?
C25 C26 C27 119.53(9) . . ?
C25 C26 C46 120.66(9) . . ?
C27 C26 C46 119.77(9) . . ?
C32 C31 C35 119.20(9) . . ?
C30 C31 C32 119.59(9) . . ?
C30 C31 C35 121.19(9) . . ?
C10 C1 C19 115.63(9) . . ?
C2 C1 C10 120.77(9) . . ?
C2 C1 C19 123.42(9) . . ?
C8 C7 C11 119.21(9) . . ?
C6 C7 C8 119.39(10) . . ?
C6 C7 C11 121.37(10) . . ?
C34 C25 C43 115.52(9) . . ?
C26 C25 C34 120.89(9) . . ?
C26 C25 C43 123.48(9) . . ?
C1 C2 C22 120.61(9) . . ?
C1 C2 C3 119.64(9) . . ?
C3 C2 C22 119.73(9) . . ?
C34 C40 C41 107.63(9) . . ?
C34 C40 C39 113.16(9) . . ?
C39 C40 C41 112.53(8) . . ?
C31 C30 C29 121.21(10) . . ?
C2 C22 C21 109.84(9) . . ?
C2 C22 C23 110.92(9) . . ?
C21 C22 C23 112.97(9) . . ?
C2 C3 C8 119.43(9) . . ?
C4 C3 C8 119.29(10) . . ?
C4 C3 C2 121.28(9) . . ?
C29 C28 C27 119.78(10) . . ?
C29 C28 C48 121.13(10) . . ?
C27 C28 C48 119.08(9) . . ?
C28 C29 C30 120.91(10) . . ?
C33 C37 C36 110.71(9) . . ?
C33 C37 C38 110.01(8) . . ?
C36 C37 C38 112.97(9) . . ?
C14 C15 C16 111.64(9) . . ?
C26 C27 C32 119.60(9) . . ?
C28 C27 C32 119.26(9) . . ?
C28 C27 C26 121.14(9) . . ?
C1 C19 C20 114.15(9) . . ?
C1 C19 C18 107.53(8) . . ?
C20 C19 C18 111.71(9) . . ?
C10 C16 C15 113.24(9) . . ?
C10 C16 C17 109.15(8) . . ?
C15 C16 C17 112.04(8) . . ?
C25 C43 C42 108.35(8) . . ?
C25 C43 C44 113.91(9) . . ?
C44 C43 C42 111.86(9) . . ?
C3 C4 C24 119.21(10) . . ?
C5 C4 C3 119.64(10) . . ?
C5 C4 C24 121.14(10) . . ?
C26 C46 C47 110.77(9) . . ?
C26 C46 C45 109.94(9) . . ?
C45 C46 C47 113.30(9) . . ?
C9 C13 C14 109.58(8) . . ?
C9 C13 C12 110.64(9) . . ?
C12 C13 C14 113.60(9) . . ?
C37 C36 C35 109.42(8) . . ?
C28 C48 C47 110.63(9) . . ?
C7 C6 C5 121.29(10) . . ?
C31 C35 C36 110.59(8) . . ?
C39 C38 C37 109.38(9) . . ?
C4 C5 C6 121.00(10) . . ?
C18 C17 C16 112.99(8) . . ?
C7 C11 C12 110.47(9) . . ?
C15 C14 C13 109.08(9) . . ?
C40 C41 C42 112.30(8) . . ?
C48 C47 C46 109.54(9) . . ?
C21 C20 C19 112.18(9) . . ?
C43 C42 C41 112.98(9) . . ?
C4 C24 C23 110.76(9) . . ?
C13 C12 C11 109.09(9) . . ?
C45 C44 C43 111.94(9) . . ?
C38 C39 C40 111.91(9) . . ?
C44 C45 C46 109.95(9) . . ?
C20 C21 C22 110.20(9) . . ?
C24 C23 C22 110.02(9) . . ?
C19 C18 C17 112.67(8) . . ?

_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.260
_oxdiff_exptl_absorpt_empirical_full_min 0.380


####################################################################### 
# 
# 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_toy2011a_hydrogenated-ruburene_chcl3-pentane_xray_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2l6v0p
_database_code_depnum_ccdc_archive 'CCDC 2389852'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2025-np2hv 2025
loop_
_audit_author_name
_audit_author_address
'Hideto Ito'
;Nagoya University
Japan
;
_audit_update_record             
;
2024-10-10 deposited with the CCDC.	2025-04-11 downloaded from the CCDC.
;
_audit_creation_date             2024-08-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        7e
_chemical_formula_moiety         'C42 H36'
_chemical_formula_sum            'C42 H36'
_chemical_formula_weight         540.7464
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H Cl'
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'

_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      orthorhombic
_space_group_IT_number           68
_space_group_name_H-M_alt        'C c c e'
_space_group_name_Hall           '-C 2b 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1, -y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'x+1, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x, y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
'-x, y+1/2, z-1/2'

_cell_length_a                   25.7173(12)
_cell_length_b                   13.4757(6)
_cell_length_c                   8.5134(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2950.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4611
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.4650
_cell_measurement_theta_min      2.9210
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/pentane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8767
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.557
_diffrn_reflns_theta_min         2.939
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  26.00   0.50  120.00    --   -2.54 -87.00 115.00   64
  2  ω     14.00  46.00   0.50  120.00    --    3.16  57.00 -90.00   64
  3  ω    -13.00  69.00   0.50  120.00    --    3.16  57.00 -30.00  164
  4  ω      3.00  38.00   0.50  120.00    --    3.16 -99.00 -60.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0041695000
_diffrn_orient_matrix_UB_12      0.0221610000
_diffrn_orient_matrix_UB_13      -0.0745103000
_diffrn_orient_matrix_UB_21      0.0270610000
_diffrn_orient_matrix_UB_22      -0.0092238000
_diffrn_orient_matrix_UB_23      0.0069866000
_diffrn_orient_matrix_UB_31      -0.0033655000
_diffrn_orient_matrix_UB_32      -0.0468330000
_diffrn_orient_matrix_UB_33      -0.0366178000
_diffrn_oxdiff_digest_frames     
;
0157a7e0762ce4822625fc3f3800e3b1ee000250ab9
;
_diffrn_oxdiff_digest_hkl        
;
010905d7a748f4b8756d30f356e6c735c1f45b
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1523
_reflns_number_total             1797
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1797
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.044
_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)+(0.0578P)²+1.6299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H00A,H00B), C5(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H006), C11(H007), C10(H009), C8(H00E), C9(H00F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.44580(4) 0.65723(6) 0.27240(11) 0.0154(2) Uani 1 1 d . . . . .
C1 C 0.47217(5) 0.750000 0.250000 0.0143(3) Uani 1 2 d S T P . .
C3 C 0.47299(3) 0.56847(7) 0.26855(11) 0.0159(2) Uani 1 1 d . . . . .
C6 C 0.38976(4) 0.65291(7) 0.32084(12) 0.0176(2) Uani 1 1 d . . . . .
C4 C 0.44531(4) 0.47168(7) 0.30699(12) 0.0209(2) Uani 1 1 d . . . . .
H00A H 0.426487 0.479603 0.407653 0.025 Uiso 1 1 calc R . . . .
H00B H 0.419189 0.458137 0.224297 0.025 Uiso 1 1 calc R . . . .
C7 C 0.37601(4) 0.67997(7) 0.47314(12) 0.0233(2) Uani 1 1 d . . . . .
H006 H 0.401763 0.705243 0.542410 0.028 Uiso 1 1 calc R . . . .
C11 C 0.35141(4) 0.61458(8) 0.22236(13) 0.0239(2) Uani 1 1 d . . . . .
H007 H 0.360196 0.594585 0.118702 0.029 Uiso 1 1 calc R . . . .
C5 C 0.48155(4) 0.38302(7) 0.31984(12) 0.0228(2) Uani 1 1 d . . . . .
H00C H 0.461056 0.320832 0.321007 0.027 Uiso 1 1 calc R . . . .
H00D H 0.501634 0.386896 0.418847 0.027 Uiso 1 1 calc R . . . .
C10 C 0.30053(4) 0.60538(10) 0.27436(15) 0.0333(3) Uani 1 1 d . . . . .
H009 H 0.274694 0.579549 0.205882 0.040 Uiso 1 1 calc R . . . .
C8 C 0.32488(5) 0.67035(10) 0.52496(14) 0.0334(3) Uani 1 1 d . . . . .
H00E H 0.315921 0.689123 0.629064 0.040 Uiso 1 1 calc R . . . .
C9 C 0.28718(4) 0.63353(10) 0.42508(16) 0.0378(3) Uani 1 1 d . . . . .
H00F H 0.252223 0.627593 0.459914 0.045 Uiso 1 1 calc R . . . .


_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
C2 C1 1.4350(10) . ?
C2 C3 1.3858(12) . ?
C2 C6 1.5003(13) . ?
C1 C1 1.431(2) 6_565 ?
C3 C3 1.4247(18) 3_655 ?
C3 C4 1.5216(12) . ?
C6 C7 1.3925(14) . ?
C6 C11 1.3936(14) . ?
C4 C5 1.5192(13) . ?
C7 C8 1.3930(15) . ?
C11 C10 1.3869(15) . ?
C5 C5 1.521(2) 3_655 ?
C10 C9 1.381(2) . ?
C8 C9 1.3818(18) . ?

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 C2 C6 121.63(8) . . ?
C3 C2 C1 120.68(9) . . ?
C3 C2 C6 117.24(8) . . ?
C2 C1 C2 123.59(11) . 8_465 ?
C1 C1 C2 118.20(6) 6_565 8_465 ?
C1 C1 C2 118.20(6) 6_565 . ?
C2 C3 C3 119.82(5) . 3_655 ?
C2 C3 C4 119.92(8) . . ?
C3 C3 C4 120.26(5) 3_655 . ?
C7 C6 C2 119.32(9) . . ?
C7 C6 C11 118.52(9) . . ?
C11 C6 C2 121.93(9) . . ?
C5 C4 C3 113.74(8) . . ?
C6 C7 C8 120.68(10) . . ?
C10 C11 C6 120.58(10) . . ?
C4 C5 C5 109.05(7) . 3_655 ?
C9 C10 C11 120.43(11) . . ?
C9 C8 C7 120.05(11) . . ?
C10 C9 C8 119.73(11) . . ?

_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.582
_oxdiff_exptl_absorpt_empirical_full_min 0.742




_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_hry091a_ad_biphenyl_red_chcl3_meoh_xray_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2mf76j
_database_code_depnum_ccdc_archive 'CCDC 2425787'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2025-np2hv 2025
loop_
_audit_author_name
_audit_author_address
'Hideto Ito'
;Nagoya University
Japan
;
_audit_update_record             
;
2025-02-21 deposited with the CCDC.	2025-04-11 downloaded from the CCDC.
;
_audit_creation_date             2024-10-30
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        compound_6c
_chemical_formula_moiety         'C22 H32'
_chemical_formula_sum            'C22 H32'
_chemical_formula_weight         296.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
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'

_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           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                   9.5878(7)
_cell_length_b                   17.3304(17)
_cell_length_c                   20.2331(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.886(8)
_cell_angle_gamma                90
_cell_volume                     3277.3(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2772
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.9480
_cell_measurement_theta_min      2.3430
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_unetI/netI     0.1010
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10234
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.467
_diffrn_reflns_theta_min         2.350
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.841
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  19.00   0.50  150.00    --   -2.70 -77.00-150.00  120
  2  ω    -60.00  63.00   0.50  150.00    --    3.32   0.00 -90.00  246
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0610811000
_diffrn_orient_matrix_UB_12      -0.0240323000
_diffrn_orient_matrix_UB_13      0.0034319000
_diffrn_orient_matrix_UB_21      0.0449078000
_diffrn_orient_matrix_UB_22      0.0320984000
_diffrn_orient_matrix_UB_23      0.0113041000
_diffrn_orient_matrix_UB_31      -0.0032617000
_diffrn_orient_matrix_UB_32      -0.0082266000
_diffrn_orient_matrix_UB_33      0.0339578000
_diffrn_oxdiff_digest_frames     
;
010e4ca2ddac9212ef7e4d30797b81da1b00025e4c5
;
_diffrn_oxdiff_digest_hkl        
;
016ad7067bf4750654ad37b4d1721859452dc9
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2696
_reflns_number_total             3835
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3835
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1226P)²+0.2299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1933
_refine_ls_wR_factor_ref         0.2108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10), C9(H9), C17(H17), C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C4(H4A,H4B), C22(H22A,H22B), C7(H7A,H7B), C18(H18A,H18B),
 C6(H6A,H6B), C5(H5A,H5B), C19(H19A,H19B), C20(H20A,H20B), C14(H14A,H14B),
 C21(H21A,H21B), C16(H16A,H16B), C12(H12A,H12B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.47157(14) 0.35220(11) 0.61505(7) 0.0168(4) Uani 1 1 d . . . . .
C2 C 0.37908(15) 0.39701(10) 0.65410(7) 0.0165(4) Uani 1 1 d . . . . .
H2 H 0.439694 0.404257 0.700754 0.020 Uiso 1 1 calc R . . . .
C8 C 0.47576(15) 0.27558(11) 0.61514(7) 0.0187(4) Uani 1 1 d . . . . .
C1 C 0.24543(15) 0.35101(11) 0.66345(7) 0.0181(4) Uani 1 1 d . . . . .
C15 C 0.13409(15) 0.34993(11) 0.59586(8) 0.0196(4) Uani 1 1 d . . . . .
H15A H 0.174229 0.322659 0.561312 0.024 Uiso 1 1 calc R . . . .
H15B H 0.048203 0.321345 0.601647 0.024 Uiso 1 1 calc R . . . .
C10 C 0.29847(16) 0.27165(11) 0.69262(7) 0.0192(4) Uani 1 1 d . . . . .
H10 H 0.372567 0.283529 0.734617 0.023 Uiso 1 1 calc R . . . .
C4 C 0.57345(16) 0.40083(11) 0.58417(8) 0.0224(4) Uani 1 1 d . . . . .
H4A H 0.637577 0.429939 0.620857 0.027 Uiso 1 1 calc R . . . .
H4B H 0.516824 0.438828 0.552678 0.027 Uiso 1 1 calc R . . . .
C9 C 0.37940(16) 0.22512(11) 0.64753(7) 0.0207(4) Uani 1 1 d . . . . .
H9 H 0.444838 0.189520 0.678925 0.025 Uiso 1 1 calc R . . . .
C17 C 0.33551(17) 0.47846(11) 0.62754(8) 0.0224(4) Uani 1 1 d . . . . .
H17 H 0.422005 0.506599 0.620395 0.027 Uiso 1 1 calc R . . . .
C22 C 0.28448(18) 0.17308(11) 0.59425(9) 0.0245(4) Uani 1 1 d . . . . .
H22A H 0.223609 0.205761 0.559179 0.029 Uiso 1 1 calc R . . . .
H22B H 0.346039 0.141160 0.571807 0.029 Uiso 1 1 calc R . . . .
C7 C 0.58432(17) 0.23104(12) 0.58581(9) 0.0260(4) Uani 1 1 d . . . . .
H7A H 0.615438 0.184869 0.614066 0.031 Uiso 1 1 calc R . . . .
H7B H 0.538581 0.213297 0.539546 0.031 Uiso 1 1 calc R . . . .
C11 C 0.09104(16) 0.43212(12) 0.57121(8) 0.0257(4) Uani 1 1 d . . . . .
H11 H 0.018124 0.429798 0.527391 0.031 Uiso 1 1 calc R . . . .
C18 C 0.22419(18) 0.47499(11) 0.56063(8) 0.0257(4) Uani 1 1 d . . . . .
H18A H 0.264638 0.447881 0.526097 0.031 Uiso 1 1 calc R . . . .
H18B H 0.197790 0.527942 0.544128 0.031 Uiso 1 1 calc R . . . .
C6 C 0.71418(17) 0.27989(12) 0.58281(8) 0.0265(4) Uani 1 1 d . . . . .
H6A H 0.768825 0.291498 0.629301 0.032 Uiso 1 1 calc R . . . .
H6B H 0.777590 0.251399 0.558842 0.032 Uiso 1 1 calc R . . . .
C5 C 0.66483(18) 0.35387(12) 0.54581(8) 0.0283(5) Uani 1 1 d . . . . .
H5A H 0.608251 0.341855 0.499768 0.034 Uiso 1 1 calc R . . . .
H5B H 0.749040 0.384664 0.541106 0.034 Uiso 1 1 calc R . . . .
C19 C 0.19021(18) 0.21801(13) 0.71684(8) 0.0296(5) Uani 1 1 d . . . . .
H19A H 0.244278 0.183800 0.752748 0.035 Uiso 1 1 calc R . . . .
H19B H 0.126696 0.250464 0.737713 0.035 Uiso 1 1 calc R . . . .
C20 C 0.09740(19) 0.16806(12) 0.66301(9) 0.0311(5) Uani 1 1 d . . . . .
H20A H 0.031872 0.201234 0.630192 0.037 Uiso 1 1 calc R . . . .
H20B H 0.038591 0.133239 0.684482 0.037 Uiso 1 1 calc R . . . .
C14 C 0.18068(18) 0.39650(13) 0.71533(8) 0.0282(5) Uani 1 1 d . . . . .
H14A H 0.094413 0.369287 0.722423 0.034 Uiso 1 1 calc R . . . .
H14B H 0.250984 0.398297 0.759324 0.034 Uiso 1 1 calc R . . . .
C13 C 0.14042(19) 0.47852(13) 0.69140(10) 0.0335(5) Uani 1 1 d . . . . .
H13 H 0.099554 0.506170 0.726135 0.040 Uiso 1 1 calc R . . . .
C21 C 0.1891(2) 0.12021(12) 0.62570(10) 0.0323(5) Uani 1 1 d . . . . .
H21A H 0.126513 0.089477 0.589651 0.039 Uiso 1 1 calc R . . . .
H21B H 0.249304 0.084063 0.657771 0.039 Uiso 1 1 calc R . . . .
C16 C 0.27304(19) 0.52155(13) 0.68059(10) 0.0319(5) Uani 1 1 d . . . . .
H16A H 0.345341 0.524594 0.723889 0.038 Uiso 1 1 calc R . . . .
H16B H 0.246690 0.574768 0.664824 0.038 Uiso 1 1 calc R . . . .
C12 C 0.02861(19) 0.47519(14) 0.62423(10) 0.0356(5) Uani 1 1 d . . . . .
H12A H 0.001155 0.528176 0.608166 0.043 Uiso 1 1 calc R . . . .
H12B H -0.058181 0.448239 0.631004 0.043 Uiso 1 1 calc R . . . .


_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
C3 C2 1.5251(19) . ?
C3 C8 1.328(3) . ?
C3 C4 1.5255(19) . ?
C2 C1 1.556(2) . ?
C2 C17 1.535(3) . ?
C8 C9 1.522(2) . ?
C8 C7 1.519(2) . ?
C1 C15 1.536(2) . ?
C1 C10 1.538(3) . ?
C1 C14 1.549(2) . ?
C15 C11 1.535(3) . ?
C10 C9 1.549(2) . ?
C10 C19 1.552(2) . ?
C4 C5 1.528(2) . ?
C9 C22 1.538(2) . ?
C17 C18 1.527(2) . ?
C17 C16 1.535(2) . ?
C22 C21 1.530(2) . ?
C7 C6 1.518(3) . ?
C11 C18 1.533(2) . ?
C11 C12 1.534(2) . ?
C6 C5 1.507(3) . ?
C19 C20 1.515(3) . ?
C20 C21 1.525(3) . ?
C14 C13 1.523(3) . ?
C13 C16 1.531(3) . ?
C13 C12 1.533(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C3 C4 115.49(15) . . ?
C8 C3 C2 121.95(13) . . ?
C8 C3 C4 122.06(13) . . ?
C3 C2 C1 113.08(14) . . ?
C3 C2 C17 115.55(11) . . ?
C17 C2 C1 110.27(13) . . ?
C3 C8 C9 123.62(13) . . ?
C3 C8 C7 122.04(14) . . ?
C7 C8 C9 114.26(15) . . ?
C15 C1 C2 109.00(12) . . ?
C15 C1 C10 115.81(14) . . ?
C15 C1 C14 107.79(13) . . ?
C10 C1 C2 107.10(12) . . ?
C10 C1 C14 110.09(12) . . ?
C14 C1 C2 106.69(14) . . ?
C11 C15 C1 111.16(14) . . ?
C1 C10 C9 113.94(11) . . ?
C1 C10 C19 118.01(13) . . ?
C9 C10 C19 109.41(15) . . ?
C3 C4 C5 113.94(15) . . ?
C8 C9 C10 112.72(14) . . ?
C8 C9 C22 110.86(12) . . ?
C22 C9 C10 114.97(12) . . ?
C18 C17 C2 110.86(14) . . ?
C18 C17 C16 109.55(14) . . ?
C16 C17 C2 108.72(13) . . ?
C21 C22 C9 112.01(13) . . ?
C6 C7 C8 111.83(16) . . ?
C18 C11 C15 108.85(13) . . ?
C18 C11 C12 109.20(16) . . ?
C12 C11 C15 110.05(14) . . ?
C17 C18 C11 109.54(13) . . ?
C5 C6 C7 108.96(14) . . ?
C6 C5 C4 110.67(12) . . ?
C20 C19 C10 116.24(12) . . ?
C19 C20 C21 110.84(14) . . ?
C13 C14 C1 111.77(13) . . ?
C14 C13 C16 109.89(15) . . ?
C14 C13 C12 108.92(17) . . ?
C16 C13 C12 109.30(15) . . ?
C20 C21 C22 110.14(16) . . ?
C13 C16 C17 109.20(16) . . ?
C13 C12 C11 109.48(13) . . ?

_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.219
_oxdiff_exptl_absorpt_empirical_full_min 0.106
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/MeOH'
