# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

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

data_ste-23-991
_database_code_depnum_ccdc_archive 'CCDC 2312246'
loop_
_audit_author_name
_audit_author_address
'Rosario Scopelliti'
;EPFL
Switzerland
;
_audit_update_record             
;
2023-12-05 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-12-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H22 O2'
_chemical_formula_sum            'C14 H22 O2'
_chemical_formula_weight         222.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H22 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.17394(11)
_cell_length_b                   8.78352(19)
_cell_length_c                   24.0129(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.6839(18)
_cell_angle_gamma                90
_cell_volume                     1301.63(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3470
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.7020
_cell_measurement_theta_min      5.3370
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.717
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0445
-2 0 -1 0.2748
0 1 0 0.0429
-1 6 -1 0.0608
1 0 1 0.3170
0 1 -2 0.0380
-1 4 -10 0.0544
0 0 -1 0.0180
0 0 1 0.0457
0 -2 1 0.0466
0 -4 12 0.0418
0 -3 13 0.0437
0 2 15 0.0475
-1 1 14 0.1045
0 -4 -10 0.0349
1 -5 -7 0.0884

_exptl_crystal_size_max          0.616
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.064
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0006 1.0000 0.9983 -0.1583 -0.0771 -0.0624
-2.0010 0.0004 -1.0015 -0.1343 -0.0499 0.4846
0.0005 0.9999 -0.0013 -0.1168 -0.1229 -0.0451
-0.8353 5.5650 -0.8743 -0.6874 -0.7251 -0.0403
1.0005 -0.0002 1.0006 0.0464 0.0478 -0.2509
0.0003 0.9997 -2.0004 -0.0337 -0.2144 -0.0106
-0.8855 4.0693 -10.2589 -0.1271 -0.9714 0.2007
-0.0001 -0.0001 -0.9996 0.0415 -0.0458 0.0173
0.0001 0.0001 0.9996 -0.0415 0.0458 -0.0173
-0.0009 -1.9998 1.0021 0.1920 0.2915 0.0729
0.0334 -3.5973 12.0860 -0.0788 0.9954 -0.0544
-0.1950 -3.1811 12.9318 -0.1827 0.9826 -0.0344
-0.2382 1.5075 15.0176 -0.8211 0.5022 -0.2713
-1.3973 1.1121 14.4365 -0.8526 0.5219 0.0272
-0.0853 -4.3441 -10.0647 0.9183 0.0724 0.3891
0.8709 -4.9350 -7.1172 0.9490 0.2818 0.1415

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6239
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.945
_diffrn_reflns_theta_min         3.683
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00   9.00   1.00    4.00    --  -40.91 105.00 -83.00   26
  2  ω     33.00  65.00   1.00    4.00    --   40.91-105.00 176.00   32
  3  ω     71.00  96.00   1.00   16.00    --  112.00-105.00 176.00   25
  4  ω    106.00 161.00   1.00   16.00    --  112.00 105.00 -83.00   55
  5  ω   -111.00 -86.00   1.00    4.00    --  -40.91 -38.00  90.00   25
  6  ω    -66.00 -17.00   1.00    4.00    --  -40.91 -38.00  90.00   49
  7  ω     18.00  98.00   1.00    4.00    --   40.91  38.00 120.00   80
  8  ω     32.00  95.00   1.00    4.00    --   40.91-125.00  30.00   63
  9  ω    112.00 158.00   1.00   16.00    --  112.00  77.00-150.00   46
 10  ω    109.00 177.00   1.00   16.00    --  112.00  77.00-120.00   68
 11  ω     40.00 136.00   1.00   16.00    --  112.00 -45.00-180.00   96
 12  ω    129.00 175.00   1.00   16.00    --  112.00 111.00 -60.00   46
 13  ω     36.00  88.00   1.00   16.00    --  112.00 -94.00-150.00   52
 14  ω     65.00  91.00   1.00   16.00    --  112.00-111.00 -30.00   26
 15  ω    140.00 175.00   1.00   16.00    --  112.00  45.00   0.00   35
 16  ω    106.00 149.00   1.00   16.00    --  112.00  77.00 -90.00   43
 17  ω     72.00 106.00   1.00   16.00    --  112.00 -94.00-120.00   34
 18  ω     48.00  73.00   1.00   16.00    --  112.00-111.00  60.00   25
 19  ω     88.00 117.00   1.00   16.00    --  112.00  45.00   0.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0878953000
_diffrn_orient_matrix_UB_12      -0.1168606000
_diffrn_orient_matrix_UB_13      -0.0415494000
_diffrn_orient_matrix_UB_21      0.0019760000
_diffrn_orient_matrix_UB_22      -0.1228121000
_diffrn_orient_matrix_UB_23      0.0458000000
_diffrn_orient_matrix_UB_31      -0.2335549000
_diffrn_orient_matrix_UB_32      -0.0450114000
_diffrn_orient_matrix_UB_33      -0.0172554000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2387
_reflns_number_total             2676
_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 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.98a 64-bit (release 24-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.070
_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)+(0.0525P)²+0.2480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1110
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.16949(16) 0.89337(11) 0.70244(4) 0.0405(2) Uani 1 1 d . . . . .
O2 O 0.69438(15) 0.43164(14) 0.60204(5) 0.0523(3) Uani 1 1 d . . . . .
C1 C 0.05972(18) 0.68588(13) 0.64380(5) 0.0294(3) Uani 1 1 d . . . . .
H1 H -0.049(2) 0.6082(18) 0.6527(6) 0.032(4) Uiso 1 1 d . . . . .
C2 C 0.13660(18) 0.75720(13) 0.69846(5) 0.0293(3) Uani 1 1 d . . . . .
C3 C 0.1716(2) 0.65302(15) 0.74805(5) 0.0337(3) Uani 1 1 d . . . . .
H3A H 0.232(3) 0.7155(19) 0.7788(7) 0.036(4) Uiso 1 1 d . . . . .
H3B H 0.030(3) 0.616(2) 0.7584(7) 0.049(5) Uiso 1 1 d . . . . .
C4 C 0.3208(2) 0.51779(14) 0.73715(5) 0.0320(3) Uani 1 1 d . . . . .
H4 H 0.369(3) 0.473(2) 0.7735(7) 0.042(4) Uiso 1 1 d . . . . .
C5 C 0.23698(19) 0.40160(13) 0.69300(5) 0.0294(3) Uani 1 1 d . . . . .
H5A H 0.295(3) 0.299(2) 0.7009(7) 0.037(4) Uiso 1 1 d . . . . .
H5B H 0.080(2) 0.3932(17) 0.6860(6) 0.029(3) Uiso 1 1 d . . . . .
C6 C 0.37423(16) 0.48529(12) 0.64895(4) 0.0247(2) Uani 1 1 d . . . . .
C7 C 0.50827(18) 0.55729(14) 0.69808(5) 0.0295(3) Uani 1 1 d . . . . .
H7A H 0.546(3) 0.6679(19) 0.6949(7) 0.038(4) Uiso 1 1 d . . . . .
H7B H 0.640(3) 0.4962(18) 0.7065(6) 0.035(4) Uiso 1 1 d . . . . .
C8 C 0.24780(18) 0.60593(13) 0.61460(5) 0.0270(3) Uani 1 1 d . . . . .
H8A H 0.187(2) 0.5596(17) 0.5802(6) 0.027(3) Uiso 1 1 d . . . . .
H8B H 0.356(3) 0.6844(19) 0.6030(7) 0.038(4) Uiso 1 1 d . . . . .
C9 C -0.0456(3) 0.80347(17) 0.60503(7) 0.0459(4) Uani 1 1 d . . . . .
H9A H -0.170(4) 0.859(3) 0.6235(9) 0.067(6) Uiso 1 1 d . . . . .
H9B H 0.062(3) 0.884(3) 0.5957(9) 0.063(6) Uiso 1 1 d . . . . .
H9C H -0.100(4) 0.755(2) 0.5712(9) 0.065(6) Uiso 1 1 d . . . . .
C10 C 0.50820(18) 0.39369(14) 0.60864(5) 0.0294(3) Uani 1 1 d . . . . .
C11 C 0.41778(18) 0.25557(13) 0.57597(5) 0.0285(3) Uani 1 1 d . . . . .
C12 C 0.1714(2) 0.24062(18) 0.57350(8) 0.0461(4) Uani 1 1 d . . . . .
H12A H 0.130(3) 0.150(2) 0.5519(7) 0.041(4) Uiso 1 1 d . . . . .
H12B H 0.112(4) 0.231(2) 0.6095(9) 0.064(6) Uiso 1 1 d . . . . .
H12C H 0.102(4) 0.331(3) 0.5555(10) 0.082(7) Uiso 1 1 d . . . . .
C13 C 0.5153(3) 0.11449(16) 0.60448(7) 0.0461(4) Uani 1 1 d . . . . .
H13A H 0.474(3) 0.023(2) 0.5819(9) 0.061(5) Uiso 1 1 d . . . . .
H13B H 0.676(4) 0.123(3) 0.6091(9) 0.069(6) Uiso 1 1 d . . . . .
H13C H 0.462(4) 0.099(3) 0.6432(11) 0.081(7) Uiso 1 1 d . . . . .
C14 C 0.5013(3) 0.2652(2) 0.51656(6) 0.0504(4) Uani 1 1 d . . . . .
H14A H 0.453(3) 0.176(2) 0.4956(9) 0.061(6) Uiso 1 1 d . . . . .
H14B H 0.437(4) 0.359(3) 0.4988(10) 0.074(7) Uiso 1 1 d . . . . .
H14C H 0.664(4) 0.274(3) 0.5172(9) 0.074(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2164(15) . ?
O2 C10 1.2117(15) . ?
C1 H1 0.984(16) . ?
C1 C2 1.5177(16) . ?
C1 C8 1.5431(16) . ?
C1 C9 1.5234(17) . ?
C2 C3 1.5122(17) . ?
C3 H3A 0.984(17) . ?
C3 H3B 0.971(19) . ?
C3 C4 1.5303(17) . ?
C4 H4 0.993(17) . ?
C4 C5 1.5495(16) . ?
C4 C7 1.5505(17) . ?
C5 H5A 0.989(17) . ?
C5 H5B 0.979(15) . ?
C5 C6 1.5588(15) . ?
C6 C7 1.5554(14) . ?
C6 C8 1.5410(15) . ?
C6 C10 1.5217(15) . ?
C7 H7A 1.002(17) . ?
C7 H7B 0.991(16) . ?
C8 H8A 0.985(15) . ?
C8 H8B 1.003(17) . ?
C9 H9A 1.02(2) . ?
C9 H9B 1.00(2) . ?
C9 H9C 0.97(2) . ?
C10 C11 1.5404(15) . ?
C11 C12 1.5265(17) . ?
C11 C13 1.5305(18) . ?
C11 C14 1.5335(19) . ?
C12 H12A 0.981(18) . ?
C12 H12B 0.95(2) . ?
C12 H12C 0.99(3) . ?
C13 H13A 1.00(2) . ?
C13 H13B 1.00(2) . ?
C13 H13C 1.01(3) . ?
C14 H14A 0.97(2) . ?
C14 H14B 1.00(2) . ?
C14 H14C 1.01(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
C2 C1 H1 107.2(9) . . ?
C2 C1 C8 111.12(9) . . ?
C2 C1 C9 111.45(10) . . ?
C8 C1 H1 108.0(9) . . ?
C9 C1 H1 108.8(9) . . ?
C9 C1 C8 110.13(11) . . ?
O1 C2 C1 121.40(11) . . ?
O1 C2 C3 120.89(11) . . ?
C3 C2 C1 117.71(10) . . ?
C2 C3 H3A 107.1(10) . . ?
C2 C3 H3B 107.0(11) . . ?
C2 C3 C4 114.07(10) . . ?
H3A C3 H3B 108.6(14) . . ?
C4 C3 H3A 110.1(10) . . ?
C4 C3 H3B 109.8(11) . . ?
C3 C4 H4 108.7(10) . . ?
C3 C4 C5 115.96(10) . . ?
C3 C4 C7 113.17(10) . . ?
C5 C4 H4 115.3(10) . . ?
C5 C4 C7 88.49(9) . . ?
C7 C4 H4 114.2(10) . . ?
C4 C5 H5A 111.1(9) . . ?
C4 C5 H5B 118.4(9) . . ?
C4 C5 C6 88.65(9) . . ?
H5A C5 H5B 108.3(13) . . ?
C6 C5 H5A 111.1(9) . . ?
C6 C5 H5B 118.2(9) . . ?
C7 C6 C5 87.98(8) . . ?
C8 C6 C5 114.24(9) . . ?
C8 C6 C7 112.10(9) . . ?
C10 C6 C5 119.92(10) . . ?
C10 C6 C7 114.23(9) . . ?
C10 C6 C8 107.42(9) . . ?
C4 C7 C6 88.74(8) . . ?
C4 C7 H7A 116.1(9) . . ?
C4 C7 H7B 112.3(9) . . ?
C6 C7 H7A 117.1(9) . . ?
C6 C7 H7B 110.5(9) . . ?
H7A C7 H7B 110.6(13) . . ?
C1 C8 H8A 107.1(8) . . ?
C1 C8 H8B 109.2(9) . . ?
C6 C8 C1 116.48(9) . . ?
C6 C8 H8A 109.9(8) . . ?
C6 C8 H8B 106.9(9) . . ?
H8A C8 H8B 106.9(12) . . ?
C1 C9 H9A 111.7(13) . . ?
C1 C9 H9B 109.9(12) . . ?
C1 C9 H9C 110.4(13) . . ?
H9A C9 H9B 106.1(17) . . ?
H9A C9 H9C 109.0(18) . . ?
H9B C9 H9C 109.6(17) . . ?
O2 C10 C6 118.25(11) . . ?
O2 C10 C11 118.75(10) . . ?
C6 C10 C11 123.00(9) . . ?
C12 C11 C10 115.68(10) . . ?
C12 C11 C13 109.04(12) . . ?
C12 C11 C14 109.30(12) . . ?
C13 C11 C10 106.14(10) . . ?
C13 C11 C14 108.80(12) . . ?
C14 C11 C10 107.67(10) . . ?
C11 C12 H12A 109.5(10) . . ?
C11 C12 H12B 112.3(13) . . ?
C11 C12 H12C 111.4(15) . . ?
H12A C12 H12B 107.9(16) . . ?
H12A C12 H12C 108.5(17) . . ?
H12B C12 H12C 107.1(19) . . ?
C11 C13 H13A 108.4(12) . . ?
C11 C13 H13B 111.3(13) . . ?
C11 C13 H13C 112.7(14) . . ?
H13A C13 H13B 111.3(17) . . ?
H13A C13 H13C 108.0(18) . . ?
H13B C13 H13C 105.1(19) . . ?
C11 C14 H14A 109.3(12) . . ?
C11 C14 H14B 107.5(14) . . ?
C11 C14 H14C 110.7(13) . . ?
H14A C14 H14B 109.3(17) . . ?
H14A C14 H14C 111.0(18) . . ?
H14B C14 H14C 109.0(19) . . ?

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
O1 C2 C3 C4 -126.61(13) . . . . ?
O2 C10 C11 C12 -163.70(14) . . . . ?
O2 C10 C11 C13 75.23(16) . . . . ?
O2 C10 C11 C14 -41.15(17) . . . . ?
C1 C2 C3 C4 53.28(15) . . . . ?
C2 C1 C8 C6 54.88(13) . . . . ?
C2 C3 C4 C5 -64.31(14) . . . . ?
C2 C3 C4 C7 35.85(14) . . . . ?
C3 C4 C5 C6 96.53(11) . . . . ?
C3 C4 C7 C6 -99.05(10) . . . . ?
C4 C5 C6 C7 18.56(8) . . . . ?
C4 C5 C6 C8 -94.82(10) . . . . ?
C4 C5 C6 C10 135.54(10) . . . . ?
C5 C4 C7 C6 18.66(8) . . . . ?
C5 C6 C7 C4 -18.55(8) . . . . ?
C5 C6 C8 C1 29.82(13) . . . . ?
C5 C6 C10 O2 -132.84(13) . . . . ?
C5 C6 C10 C11 47.22(15) . . . . ?
C6 C10 C11 C12 16.24(17) . . . . ?
C6 C10 C11 C13 -104.83(13) . . . . ?
C6 C10 C11 C14 138.79(13) . . . . ?
C7 C4 C5 C6 -18.62(8) . . . . ?
C7 C6 C8 C1 -68.29(12) . . . . ?
C7 C6 C10 O2 -30.45(17) . . . . ?
C7 C6 C10 C11 149.61(11) . . . . ?
C8 C1 C2 O1 102.28(13) . . . . ?
C8 C1 C2 C3 -77.61(13) . . . . ?
C8 C6 C7 C4 96.86(10) . . . . ?
C8 C6 C10 O2 94.55(14) . . . . ?
C8 C6 C10 C11 -85.39(13) . . . . ?
C9 C1 C2 O1 -20.96(17) . . . . ?
C9 C1 C2 C3 159.15(12) . . . . ?
C9 C1 C8 C6 178.88(10) . . . . ?
C10 C6 C7 C4 -140.66(10) . . . . ?
C10 C6 C8 C1 165.43(9) . . . . ?

_olex2_date_sample_data_collection 2023-12-05
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.476
_oxdiff_exptl_absorpt_empirical_full_min 0.480
####################################################################### 
# 
# 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_ste-24-1162
_database_code_depnum_ccdc_archive 'CCDC 2356953'
loop_
_audit_author_name
_audit_author_address
'Rosario Scopelliti'
;EPFL
Switzerland
;
_audit_update_record             
;
2024-05-21 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2024-05-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 O2'
_chemical_formula_sum            'C21 H22 O2'
_chemical_formula_weight         306.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H22 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   17.7615(2)
_cell_length_b                   6.40467(8)
_cell_length_c                   13.86477(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.9318(11)
_cell_angle_gamma                90
_cell_volume                     1568.76(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4923
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.3010
_cell_measurement_theta_min      5.0060
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.673
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.123a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 2 -2 0.3323
2 -2 1 0.3022
1 -2 2 0.2890
2 0 -1 0.0807
-2 -1 1 0.2571
1 2 -1 0.3215
-1 2 0 0.3093
1 0 0 0.0422
-1 0 0 0.0543
-2 -1 -1 0.3076
1 -2 -2 0.3495
9 2 2 0.1826
-11 1 1 0.0928
0 1 1 0.3027
-2 0 -1 0.0950
2 0 1 0.0487
0 0 -1 0.1318
0 0 1 0.1023
5 -2 7 0.1577
-2 -2 7 0.1878
-11 0 4 0.0672
-10 -1 4 0.1148
-11 -1 1 0.0622
-11 0 2 0.0433
1 0 -2 0.1167

_exptl_crystal_size_max          0.673
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.097
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 2.0000 -2.0000 -0.2684 0.3190 -0.3455
2.0000 -2.0000 1.0000 0.1950 -0.2413 0.4269
1.0000 -2.0000 2.0000 0.2684 -0.3190 0.3455
2.0000 -0.0000 -1.0000 -0.1379 0.0484 0.1323
-2.0000 -1.0000 1.0000 0.2954 -0.0862 0.0456
1.0000 2.0000 -1.0000 -0.3884 0.1533 -0.2744
-1.0000 2.0000 -0.0000 -0.2505 0.1049 -0.4066
1.0000 -0.0000 0.0000 -0.0645 -0.0293 0.0508
-1.0000 0.0000 -0.0000 0.0645 0.0293 -0.0508
-2.0000 -1.0000 -1.0000 0.2774 0.1280 0.1068
1.0000 -2.0000 -2.0000 0.2326 0.1093 0.4678
8.6904 2.4170 2.0457 -0.9225 -0.3827 -0.0507
-11.3654 0.7036 0.9129 0.6300 0.2622 -0.7310
-0.0000 1.0000 1.0000 -0.1485 -0.0693 -0.2085
-2.0000 -0.0000 -1.0000 0.1200 0.1657 -0.0711
2.0000 0.0000 1.0000 -0.1200 -0.1657 0.0711
0.0000 -0.0000 -1.0000 -0.0090 0.1071 0.0306
-0.0000 0.0000 1.0000 0.0090 -0.1071 -0.0306
4.5006 -1.9275 6.7544 0.0739 -0.9280 0.3651
-1.7599 -2.4400 7.2565 0.5627 -0.8175 0.1226
-10.5283 0.0667 4.4991 0.7085 -0.1704 -0.6849
-10.0519 -1.2393 4.2925 0.8816 -0.2116 -0.4220
-11.4058 -0.5546 1.4829 0.8359 0.1548 -0.5266
-11.4765 -0.0952 1.7784 0.7707 0.1426 -0.6210
1.0000 -0.0000 -2.0000 -0.0824 0.1848 0.1120

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7738
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.026
_diffrn_reflns_theta_min         5.007
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  31.00   1.00    2.00    --  -40.91  56.00-122.00   89
  2  ω   -112.00 -19.00   1.00    2.00    --  -40.91 -56.00  95.00   93
  3  ω     91.00 171.00   1.00    8.00    --  112.00  56.00-122.00   80
  4  ω     56.00 127.00   1.00    8.00    --  112.00 -56.00  95.00   71
  5  ω     13.00  75.00   1.00    2.00    --   40.91 -99.00 -60.00   62
  6  ω     55.00  94.00   1.00    2.00    --   40.91-125.00  60.00   39
  7  ω     85.00 110.00   1.00    8.00    --  112.00  30.00-150.00   25
  8  ω    105.00 131.00   1.00    8.00    --  112.00  77.00 120.00   26
  9  ω    145.00 175.00   1.00    8.00    --  112.00  77.00 120.00   30
 10  ω    105.00 168.00   1.00    8.00    --  112.00 111.00-120.00   63
 11  ω    105.00 177.00   1.00    8.00    --  112.00  61.00 150.00   72
 12  ω    153.00 178.00   1.00    8.00    --  112.00  30.00-150.00   25
 13  ω     45.00  92.00   1.00    8.00    --  112.00-111.00  60.00   47
 14  ω     39.00 105.00   1.00    8.00    --  112.00-111.00  90.00   66
 15  ω     97.00 149.00   1.00    8.00    --  112.00  45.00-150.00   52
 16  ω    133.00 166.00   1.00    8.00    --  112.00 111.00-150.00   33
 17  ω    108.00 143.00   1.00    8.00    --  112.00 111.00 150.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0644620000
_diffrn_orient_matrix_UB_12      -0.1574801000
_diffrn_orient_matrix_UB_13      0.0089572000
_diffrn_orient_matrix_UB_21      -0.0293318000
_diffrn_orient_matrix_UB_22      0.0377697000
_diffrn_orient_matrix_UB_23      -0.1070749000
_diffrn_orient_matrix_UB_31      0.0508459000
_diffrn_orient_matrix_UB_32      -0.1779010000
_diffrn_orient_matrix_UB_33      -0.0305985000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2925
_reflns_number_total             3208
_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 1.171.43.123a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.123a 64-bit (release 20-05-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.123a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0405
_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)+(0.0660P)²+0.2959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1104
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.94179(5) 0.42003(15) 0.81419(6) 0.0342(2) Uani 1 1 d . . . . .
O2 O 0.75331(5) -0.03495(14) 0.50973(7) 0.0340(2) Uani 1 1 d . . . . .
C1 C 0.92357(6) 0.46732(17) 0.73011(8) 0.0246(2) Uani 1 1 d . . . . .
C2 C 0.97660(6) 0.43609(19) 0.65276(9) 0.0287(3) Uani 1 1 d . . . . .
H2A H 0.9919(9) 0.574(3) 0.6319(12) 0.037(4) Uiso 1 1 d . . . . .
H2B H 1.0222(10) 0.368(3) 0.6814(12) 0.038(4) Uiso 1 1 d . . . . .
C3 C 0.94332(6) 0.30487(19) 0.56628(9) 0.0273(3) Uani 1 1 d . . . . .
H3 H 0.9825(9) 0.260(2) 0.5288(11) 0.028(4) Uiso 1 1 d . . . . .
C4 C 0.89116(6) 0.12746(18) 0.59591(9) 0.0259(2) Uani 1 1 d . . . . .
H4A H 0.8988(9) 0.078(3) 0.6645(12) 0.032(4) Uiso 1 1 d . . . . .
H4B H 0.8915(9) 0.006(3) 0.5526(12) 0.033(4) Uiso 1 1 d . . . . .
C5 C 0.82125(6) 0.26943(16) 0.56652(7) 0.0203(2) Uani 1 1 d . . . . .
C6 C 0.79105(5) 0.39161(16) 0.65130(7) 0.0199(2) Uani 1 1 d . . . . .
H6 H 0.7469(8) 0.473(2) 0.6222(10) 0.021(3) Uiso 1 1 d . . . . .
C7 C 0.84621(6) 0.56099(17) 0.69800(7) 0.0221(2) Uani 1 1 d . . . . .
H7 H 0.8528(8) 0.666(2) 0.6472(11) 0.026(3) Uiso 1 1 d . . . . .
C8 C 0.87369(6) 0.39964(18) 0.50461(8) 0.0250(2) Uani 1 1 d . . . . .
H8A H 0.8680(8) 0.550(3) 0.5022(11) 0.026(3) Uiso 1 1 d . . . . .
H8B H 0.8706(9) 0.350(3) 0.4393(11) 0.030(4) Uiso 1 1 d . . . . .
C9 C 0.76563(6) 0.23945(19) 0.72677(8) 0.0266(2) Uani 1 1 d . . . . .
H9A H 0.7376(10) 0.307(3) 0.7743(13) 0.040(4) Uiso 1 1 d . . . . .
H9B H 0.7316(10) 0.132(3) 0.6958(12) 0.040(4) Uiso 1 1 d . . . . .
H9C H 0.8075(9) 0.164(3) 0.7635(11) 0.030(4) Uiso 1 1 d . . . . .
C10 C 0.81313(7) 0.6732(2) 0.78120(9) 0.0304(3) Uani 1 1 d . . . . .
H10A H 0.8111(10) 0.584(3) 0.8390(14) 0.044(4) Uiso 1 1 d . . . . .
H10B H 0.8438(10) 0.801(3) 0.8003(12) 0.040(4) Uiso 1 1 d . . . . .
H10C H 0.7600(10) 0.718(3) 0.7611(13) 0.045(5) Uiso 1 1 d . . . . .
C11 C 0.75485(6) 0.15471(17) 0.51175(7) 0.0224(2) Uani 1 1 d . . . . .
C12 C 0.68880(6) 0.27718(17) 0.46426(7) 0.0211(2) Uani 1 1 d . . . . .
C13 C 0.69458(6) 0.48820(17) 0.43464(7) 0.0230(2) Uani 1 1 d . . . . .
H13 H 0.7414(9) 0.560(3) 0.4426(11) 0.030(4) Uiso 1 1 d . . . . .
C14 C 0.63242(6) 0.59102(18) 0.39155(8) 0.0251(2) Uani 1 1 d . . . . .
H14 H 0.6365(9) 0.730(3) 0.3708(11) 0.031(4) Uiso 1 1 d . . . . .
C15 C 0.56038(6) 0.49316(19) 0.37906(7) 0.0241(2) Uani 1 1 d . . . . .
C16 C 0.49426(7) 0.5991(2) 0.33845(8) 0.0303(3) Uani 1 1 d . . . . .
H16 H 0.4994(9) 0.738(3) 0.3157(11) 0.032(4) Uiso 1 1 d . . . . .
C17 C 0.42529(7) 0.5015(2) 0.33152(9) 0.0349(3) Uani 1 1 d . . . . .
H17 H 0.3818(11) 0.579(3) 0.3056(13) 0.046(5) Uiso 1 1 d . . . . .
C18 C 0.41863(7) 0.2939(2) 0.36258(9) 0.0347(3) Uani 1 1 d . . . . .
H18 H 0.3684(11) 0.225(3) 0.3583(13) 0.046(5) Uiso 1 1 d . . . . .
C19 C 0.48166(6) 0.1856(2) 0.39952(8) 0.0290(3) Uani 1 1 d . . . . .
H19 H 0.4783(9) 0.041(3) 0.4195(11) 0.033(4) Uiso 1 1 d . . . . .
C20 C 0.55395(6) 0.28309(18) 0.40952(7) 0.0234(2) Uani 1 1 d . . . . .
C21 C 0.61972(6) 0.17744(17) 0.45028(7) 0.0225(2) Uani 1 1 d . . . . .
H21 H 0.6157(8) 0.037(2) 0.4707(10) 0.024(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2155(15) . ?
O2 C11 1.2153(15) . ?
C1 C2 1.5119(16) . ?
C1 C7 1.5231(14) . ?
C2 H2A 0.975(19) . ?
C2 H2B 0.969(18) . ?
C2 C3 1.5319(16) . ?
C3 H3 0.955(15) . ?
C3 C4 1.5480(16) . ?
C3 C8 1.5525(15) . ?
C4 H4A 0.999(16) . ?
C4 H4B 0.984(18) . ?
C4 C5 1.5589(14) . ?
C5 C6 1.5531(14) . ?
C5 C8 1.5701(14) . ?
C5 C11 1.5239(14) . ?
C6 H6 0.990(14) . ?
C6 C7 1.5571(14) . ?
C6 C9 1.5318(14) . ?
C7 H7 0.991(15) . ?
C7 C10 1.5275(15) . ?
C8 H8A 0.970(17) . ?
C8 H8B 0.956(16) . ?
C9 H9A 0.969(18) . ?
C9 H9B 0.985(19) . ?
C9 H9C 0.984(16) . ?
C10 H10A 0.987(19) . ?
C10 H10B 1.006(19) . ?
C10 H10C 0.999(19) . ?
C11 C12 1.5051(14) . ?
C12 C13 1.4194(16) . ?
C12 C21 1.3790(15) . ?
C13 H13 0.946(16) . ?
C13 C14 1.3687(16) . ?
C14 H14 0.940(17) . ?
C14 C15 1.4191(16) . ?
C15 C16 1.4212(16) . ?
C15 C20 1.4183(17) . ?
C16 H16 0.951(17) . ?
C16 C17 1.3699(19) . ?
C17 H17 0.96(2) . ?
C17 C18 1.406(2) . ?
C18 H18 0.990(19) . ?
C18 C19 1.3705(18) . ?
C19 H19 0.971(18) . ?
C19 C20 1.4216(15) . ?
C20 C21 1.4162(15) . ?
C21 H21 0.947(16) . ?

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
O1 C1 C2 121.58(10) . . ?
O1 C1 C7 121.41(10) . . ?
C2 C1 C7 117.00(9) . . ?
C1 C2 H2A 107.7(10) . . ?
C1 C2 H2B 108.9(10) . . ?
C1 C2 C3 114.17(9) . . ?
H2A C2 H2B 106.5(14) . . ?
C3 C2 H2A 111.1(10) . . ?
C3 C2 H2B 108.1(11) . . ?
C2 C3 H3 110.3(9) . . ?
C2 C3 C4 112.84(10) . . ?
C2 C3 C8 115.94(9) . . ?
C4 C3 H3 114.4(9) . . ?
C4 C3 C8 88.20(8) . . ?
C8 C3 H3 113.7(9) . . ?
C3 C4 H4A 117.3(9) . . ?
C3 C4 H4B 112.2(9) . . ?
C3 C4 C5 89.13(8) . . ?
H4A C4 H4B 108.7(13) . . ?
C5 C4 H4A 117.4(9) . . ?
C5 C4 H4B 110.9(10) . . ?
C4 C5 C8 87.20(8) . . ?
C6 C5 C4 115.09(8) . . ?
C6 C5 C8 114.64(8) . . ?
C11 C5 C4 113.80(9) . . ?
C11 C5 C6 108.06(8) . . ?
C11 C5 C8 117.13(9) . . ?
C5 C6 H6 106.1(8) . . ?
C5 C6 C7 114.46(8) . . ?
C7 C6 H6 103.9(8) . . ?
C9 C6 C5 110.23(9) . . ?
C9 C6 H6 109.6(8) . . ?
C9 C6 C7 112.11(8) . . ?
C1 C7 C6 110.91(8) . . ?
C1 C7 H7 107.8(8) . . ?
C1 C7 C10 111.74(9) . . ?
C6 C7 H7 107.1(9) . . ?
C10 C7 C6 111.56(9) . . ?
C10 C7 H7 107.4(9) . . ?
C3 C8 C5 88.57(8) . . ?
C3 C8 H8A 118.8(9) . . ?
C3 C8 H8B 110.9(9) . . ?
C5 C8 H8A 118.8(8) . . ?
C5 C8 H8B 111.2(10) . . ?
H8A C8 H8B 107.6(13) . . ?
C6 C9 H9A 112.8(11) . . ?
C6 C9 H9B 110.9(10) . . ?
C6 C9 H9C 113.9(9) . . ?
H9A C9 H9B 106.0(14) . . ?
H9A C9 H9C 106.4(13) . . ?
H9B C9 H9C 106.3(14) . . ?
C7 C10 H10A 112.9(11) . . ?
C7 C10 H10B 110.0(9) . . ?
C7 C10 H10C 110.6(10) . . ?
H10A C10 H10B 108.8(14) . . ?
H10A C10 H10C 106.3(15) . . ?
H10B C10 H10C 108.0(15) . . ?
O2 C11 C5 120.51(10) . . ?
O2 C11 C12 119.75(10) . . ?
C12 C11 C5 119.66(9) . . ?
C13 C12 C11 123.11(9) . . ?
C21 C12 C11 117.51(10) . . ?
C21 C12 C13 119.37(10) . . ?
C12 C13 H13 121.2(10) . . ?
C14 C13 C12 120.34(10) . . ?
C14 C13 H13 118.4(10) . . ?
C13 C14 H14 120.3(9) . . ?
C13 C14 C15 121.15(10) . . ?
C15 C14 H14 118.5(9) . . ?
C14 C15 C16 122.35(11) . . ?
C20 C15 C14 118.82(10) . . ?
C20 C15 C16 118.82(10) . . ?
C15 C16 H16 118.3(10) . . ?
C17 C16 C15 120.42(12) . . ?
C17 C16 H16 121.3(9) . . ?
C16 C17 H17 118.1(12) . . ?
C16 C17 C18 120.86(11) . . ?
C18 C17 H17 121.0(12) . . ?
C17 C18 H18 120.4(11) . . ?
C19 C18 C17 120.10(11) . . ?
C19 C18 H18 119.5(11) . . ?
C18 C19 H19 121.2(9) . . ?
C18 C19 C20 120.58(12) . . ?
C20 C19 H19 118.2(9) . . ?
C15 C20 C19 119.18(10) . . ?
C21 C20 C15 118.91(10) . . ?
C21 C20 C19 121.90(11) . . ?
C12 C21 C20 121.33(10) . . ?
C12 C21 H21 119.5(9) . . ?
C20 C21 H21 119.2(9) . . ?

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
O1 C1 C2 C3 124.70(12) . . . . ?
O1 C1 C7 C6 -99.59(12) . . . . ?
O1 C1 C7 C10 25.57(14) . . . . ?
O2 C11 C12 C13 -158.41(11) . . . . ?
O2 C11 C12 C21 22.18(15) . . . . ?
C1 C2 C3 C4 -35.59(13) . . . . ?
C1 C2 C3 C8 64.02(13) . . . . ?
C2 C1 C7 C6 80.46(11) . . . . ?
C2 C1 C7 C10 -154.38(10) . . . . ?
C2 C3 C4 C5 97.67(10) . . . . ?
C2 C3 C8 C5 -94.93(10) . . . . ?
C3 C4 C5 C6 -96.36(10) . . . . ?
C3 C4 C5 C8 19.61(8) . . . . ?
C3 C4 C5 C11 138.13(9) . . . . ?
C4 C3 C8 C5 19.69(8) . . . . ?
C4 C5 C6 C7 66.56(11) . . . . ?
C4 C5 C6 C9 -60.91(11) . . . . ?
C4 C5 C8 C3 -19.56(8) . . . . ?
C4 C5 C11 O2 13.48(14) . . . . ?
C4 C5 C11 C12 -169.76(9) . . . . ?
C5 C6 C7 C1 -54.25(11) . . . . ?
C5 C6 C7 C10 -179.52(9) . . . . ?
C5 C11 C12 C13 24.80(14) . . . . ?
C5 C11 C12 C21 -154.60(10) . . . . ?
C6 C5 C8 C3 96.84(9) . . . . ?
C6 C5 C11 O2 -115.68(11) . . . . ?
C6 C5 C11 C12 61.09(11) . . . . ?
C7 C1 C2 C3 -55.35(13) . . . . ?
C8 C3 C4 C5 -19.83(8) . . . . ?
C8 C5 C6 C7 -32.38(12) . . . . ?
C8 C5 C6 C9 -159.85(9) . . . . ?
C8 C5 C11 O2 113.03(12) . . . . ?
C8 C5 C11 C12 -70.20(12) . . . . ?
C9 C6 C7 C1 72.25(11) . . . . ?
C9 C6 C7 C10 -53.02(12) . . . . ?
C11 C5 C6 C7 -165.01(8) . . . . ?
C11 C5 C6 C9 67.51(10) . . . . ?
C11 C5 C8 C3 -134.96(9) . . . . ?
C11 C12 C13 C14 179.82(9) . . . . ?
C11 C12 C21 C20 177.59(9) . . . . ?
C12 C13 C14 C15 2.63(16) . . . . ?
C13 C12 C21 C20 -1.84(15) . . . . ?
C13 C14 C15 C16 177.19(10) . . . . ?
C13 C14 C15 C20 -1.85(16) . . . . ?
C14 C15 C16 C17 -177.19(11) . . . . ?
C14 C15 C20 C19 178.42(10) . . . . ?
C14 C15 C20 C21 -0.73(15) . . . . ?
C15 C16 C17 C18 -1.24(18) . . . . ?
C15 C20 C21 C12 2.57(15) . . . . ?
C16 C15 C20 C19 -0.65(15) . . . . ?
C16 C15 C20 C21 -179.80(9) . . . . ?
C16 C17 C18 C19 -0.63(19) . . . . ?
C17 C18 C19 C20 1.83(18) . . . . ?
C18 C19 C20 C15 -1.18(16) . . . . ?
C18 C19 C20 C21 177.95(10) . . . . ?
C19 C20 C21 C12 -176.55(10) . . . . ?
C20 C15 C16 C17 1.85(16) . . . . ?
C21 C12 C13 C14 -0.78(15) . . . . ?

_olex2_date_sample_data_collection 2024-05-21
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 6.825
_oxdiff_exptl_absorpt_empirical_full_min 0.492
####################################################################### 
# 
# 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_ste-24-1037
_database_code_depnum_ccdc_archive 'CCDC 2333992'
loop_
_audit_author_name
_audit_author_address
'Rosario Scopelliti'
;EPFL
Switzerland
;
_audit_update_record             
;
2024-02-20 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2024-02-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 O2'
_chemical_formula_sum            'C21 H22 O2'
_chemical_formula_weight         306.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H22 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.11476(18)
_cell_length_b                   10.4720(2)
_cell_length_c                   10.7595(4)
_cell_angle_alpha                67.728(3)
_cell_angle_beta                 74.021(2)
_cell_angle_gamma                82.9324(19)
_cell_volume                     813.23(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11017
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.3950
_cell_measurement_theta_min      4.5480
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 2 -1 0.0834
2 -2 1 0.1238
-1 0 2 0.0956
-1 -2 5 0.0904
1 -2 2 0.1133
2 -1 -1 0.0833
-1 1 6 0.0901
0 0 1 0.0987
0 0 -1 0.1046
1 6 5 0.0494
-1 -2 -2 0.0585
-5 -2 -3 0.0652
-4 4 2 0.0923
1 2 1 0.0621
-1 7 3 0.0668
-3 -5 0 0.0694
1 2 0 0.0850
1 6 0 0.0839
0 1 -1 0.0978
-1 1 0 0.0813
-3 1 -5 0.0894
2 5 6 0.0740
-5 0 -4 0.0653
-5 -3 -2 0.0652
-3 -4 1 0.0709

_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.134
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0000 2.0000 -1.0000 -0.1937 0.1689 0.4768
2.0000 -2.0000 1.0000 0.1937 -0.1689 -0.4768
-1.0000 0.0000 2.0000 0.2673 -0.2284 0.2212
-1.2270 -1.5207 5.0365 0.7084 -0.6716 0.2171
1.0000 -2.0000 2.0000 0.3188 -0.3281 -0.2787
2.0000 -1.0000 -1.0000 -0.0994 0.1094 -0.4480
-1.3374 1.0226 5.9015 0.8072 -0.3854 0.4471
-0.0000 -0.0000 1.0000 0.1421 -0.0691 0.0231
0.0000 0.0000 -1.0000 -0.1421 0.0691 -0.0231
1.4972 6.0492 5.2728 0.7220 0.6168 0.3135
-1.0000 -2.0000 -2.0000 -0.2838 -0.2317 -0.0212
-5.1616 -1.5210 -3.2021 -0.5296 -0.4564 0.7150
-3.6258 4.0836 1.7415 0.1501 0.1244 0.9808
1.0000 2.0000 1.0000 0.1416 0.3008 -0.0019
-0.5551 6.5925 2.7675 0.3262 0.6812 0.6554
-3.2992 -4.9004 -0.0747 -0.0238 -0.9778 0.2081
1.0000 2.0000 0.0000 -0.0005 0.3700 -0.0250
0.8331 6.3995 0.4673 0.0245 0.9383 0.3449
0.0000 1.0000 -1.0000 -0.1509 0.2091 0.0519
-1.0000 1.0000 0.0000 -0.0258 0.0499 0.2499
-3.0216 1.4060 -5.2433 -0.8090 0.2871 0.5129
2.1310 4.5536 6.4753 0.9168 0.3815 0.1183
-4.9768 -0.4052 -3.6969 -0.6066 -0.2494 0.7549
-4.7973 -3.2950 -1.5877 -0.2784 -0.7835 0.5556
-2.8296 -4.4133 1.3275 0.1793 -0.9643 0.1948

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17602
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.563
_diffrn_reflns_theta_min         4.564
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -34.00   0.50    0.20    --  -76.25 132.00  74.01  148
  2  ω   -108.00 -34.00   0.50    0.20    --  -76.25 132.00  74.01  148
  3  ω   -108.00 -33.00   0.50    0.20    --  -70.95   0.00 -60.00  150
  4  ω   -108.00 -33.00   0.50    0.20    --  -70.95   0.00 -60.00  150
  5  ω   -112.00 -80.00   0.50    0.20    --  -76.25 -76.00 -62.27   64
  6  ω   -118.00 -86.00   0.50    0.20    --  -76.25 -60.00   7.60   64
  7  ω    -74.00 -43.00   0.50    0.20    --  -36.00 -69.00 132.42   62
  8  ω   -115.00 -84.00   0.50    0.20    --  -76.25 -67.00 149.39   62
  9  ω   -119.00 -86.00   0.50    0.20    --  -76.25 -56.00 139.53   66
 10  ω   -112.00 -79.00   0.50    0.20    --  -68.00 -52.00 104.70   66
 11  ω   -118.00 -85.00   0.50    0.20    --  -72.00 -41.00  65.33   66
 12  ω   -123.00 -86.00   0.50    0.20    --  -76.25 -36.00  71.26   74
 13  ω   -114.00 -81.00   0.50    0.20    --  -68.00 -41.00  27.86   66
 14  ω    -74.00 -43.00   0.50    0.20    --  -36.00 -69.00-154.64   62
 15  ω   -121.00 -87.00   0.50    0.20    --  -76.25 -50.00-175.47   68
 16  ω   -112.00 -79.00   0.50    0.20    --  -76.25 -90.00 -16.61   66
 17  ω     46.00  77.00   0.50    0.20    --   40.00  72.00-136.17   62
 18  ω     40.00  72.00   0.50    0.20    --   36.00  76.00  54.40   64
 19  ω     45.00  77.00   0.50    0.20    --   40.00  74.00 113.73   64
 20  ω     51.00  84.00   0.50    0.20    --   40.00  53.00  29.85   66
 21  ω     47.00  74.00   0.50    0.20    --   79.75   2.00 -37.28   54
 22  ω     62.00  94.00   0.50    0.20    --   52.00  58.00 -51.26   64
 23  ω     69.00 101.00   0.50    0.20    --   60.00  62.00-132.95   64
 24  ω     62.00  95.00   0.50    0.20    --   52.00  57.00 -93.10   66
 25  ω     91.00 116.00   0.50    0.20    --   79.75  49.00 -36.70   50
 26  ω     94.00 125.00   0.50    0.20    --   79.75  35.00 -51.64   62
 27  ω     77.00 105.00   0.50    0.20    --   79.75  26.00 -78.77   56
 28  ω     73.00 106.00   0.50    0.20    --   79.75  25.00 -44.42   66
 29  ω    100.00 126.00   0.50    0.20    --   79.75  32.00  -7.85   52
 30  ω     45.00 110.00   0.50    0.20    --   79.75   3.00-131.14  130
 31  ω     79.00 110.00   0.50    0.20    --   79.75   3.00-101.06   62
 32  ω     97.00 124.00   0.50    0.20    --   79.75  46.00  25.36   54
 33  ω     94.00 121.00   0.50    0.20    --   79.75   6.00 152.15   54
 34  ω     58.00  88.00   0.50    0.20    --   79.75   6.00 152.15   60
 35  ω     35.00 103.00   0.50    0.20    --   76.40-125.00  90.00  136
 36  ω     35.00 103.00   0.50    0.20    --   76.40-125.00 150.00  136
 37  ω     35.00 103.00   0.50    0.20    --   76.40-125.00 120.00  136
 38  ω     35.00 103.00   0.50    0.20    --   76.40-125.00  90.00  136
 39  ω     35.00 103.00   0.50    0.20    --   76.40-125.00 -30.00  136
 40  ω     35.00 103.00   0.50    0.20    --   76.40-125.00 -90.00  136
 41  ω     49.00 103.00   0.50    0.20    --   76.40-125.00-150.00  108
 42  ω     40.00 105.00   0.50    0.20    --   79.75-123.00-137.96  130
 43  ω     38.00  84.00   0.50    0.20    --   75.71 -95.00-150.00   92
 44  ω     48.00  99.00   0.50    0.20    --   79.75-113.00 -76.36  102
 45  ω     39.00  85.00   0.50    0.20    --   76.40 -95.00 -30.00   92
 46  ω     39.00  85.00   0.50    0.20    --   76.40 -95.00-120.00   92
 47  ω     41.00 105.00   0.50    0.20    --   79.75-122.00  36.50  128
 48  ω     46.00  91.00   0.50    0.20    --   79.75-100.00  71.83   90
 49  ω     39.00  85.00   0.50    0.20    --   76.40 -95.00  90.00   92
 50  ω     39.00  85.00   0.50    0.20    --   76.40 -95.00 150.00   92
 51  ω     39.00  85.00   0.50    0.20    --   76.40 -95.00 120.00   92
 52  ω     38.00  84.00   0.50    0.20    --   75.71 -95.00  30.00   92
 53  ω     39.00  85.00   0.50    0.20    --   76.40 -95.00   0.00   92
 54  ω     26.00  72.00   0.50    0.20    --   63.71 -95.00 -30.00   92
 55  ω     38.00  84.00   0.50    0.20    --   75.71 -95.00 -60.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0170050000
_diffrn_orient_matrix_UB_12      -0.0087649000
_diffrn_orient_matrix_UB_13      0.1421478000
_diffrn_orient_matrix_UB_21      0.0900846000
_diffrn_orient_matrix_UB_22      0.1399457000
_diffrn_orient_matrix_UB_23      -0.0691481000
_diffrn_orient_matrix_UB_31      -0.1749574000
_diffrn_orient_matrix_UB_32      0.0749796000
_diffrn_orient_matrix_UB_33      0.0231179000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2901
_reflns_number_total             3274
_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 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.105a 64-bit (release 11-01-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0025(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.070
_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)+(0.0571P)²+0.2306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1140
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.37508(14) 0.03002(10) 0.35708(11) 0.0461(3) Uani 1 1 d . . . . .
O2 O -0.13783(13) 0.39961(10) 0.65978(11) 0.0444(3) Uani 1 1 d . . . . .
C1 C 0.35861(17) 0.14264(13) 0.36918(14) 0.0327(3) Uani 1 1 d . . . . .
C2 C 0.21963(16) 0.16594(12) 0.48636(13) 0.0292(3) Uani 1 1 d . . . . .
C3 C 0.15014(19) 0.03314(13) 0.61030(14) 0.0342(3) Uani 1 1 d . . . . .
H3A H 0.237(2) -0.0409(16) 0.6175(16) 0.037(4) Uiso 1 1 d . . . . .
H3B H 0.040(2) -0.0024(16) 0.6119(16) 0.039(4) Uiso 1 1 d . . . . .
C4 C 0.14871(18) 0.10796(13) 0.71014(14) 0.0347(3) Uani 1 1 d . . . . .
H4 H 0.1922(19) 0.0511(16) 0.7910(16) 0.035(4) Uiso 1 1 d . . . . .
C5 C -0.01908(18) 0.17820(14) 0.76212(14) 0.0365(3) Uani 1 1 d . . . . .
H5 H 0.002(2) 0.2287(16) 0.8236(16) 0.038(4) Uiso 1 1 d . . . . .
C6 C -0.08771(16) 0.28965(13) 0.64762(14) 0.0327(3) Uani 1 1 d . . . . .
C7 C -0.09989(16) 0.25783(13) 0.52437(14) 0.0329(3) Uani 1 1 d . . . . .
H7 H -0.145(2) 0.1630(17) 0.5611(16) 0.039(4) Uiso 1 1 d . . . . .
C8 C 0.07712(16) 0.25788(12) 0.42419(13) 0.0296(3) Uani 1 1 d . . . . .
H8A H 0.113(2) 0.3554(16) 0.3777(16) 0.038(4) Uiso 1 1 d . . . . .
H8B H 0.058(2) 0.2284(16) 0.3526(17) 0.037(4) Uiso 1 1 d . . . . .
C9 C 0.27608(17) 0.21179(14) 0.59066(14) 0.0328(3) Uani 1 1 d . . . . .
H9A H 0.255(2) 0.3116(17) 0.5817(16) 0.038(4) Uiso 1 1 d . . . . .
H9B H 0.394(2) 0.1819(15) 0.5939(16) 0.037(4) Uiso 1 1 d . . . . .
C10 C -0.1606(2) 0.07523(17) 0.85509(16) 0.0456(4) Uani 1 1 d . . . . .
H10A H -0.197(2) 0.0249(18) 0.7985(19) 0.054(5) Uiso 1 1 d . . . . .
H10B H -0.269(2) 0.1272(19) 0.8911(19) 0.057(5) Uiso 1 1 d . . . . .
H10C H -0.115(2) 0.007(2) 0.935(2) 0.062(5) Uiso 1 1 d . . . . .
C11 C -0.21862(19) 0.35861(17) 0.44348(17) 0.0424(3) Uani 1 1 d . . . . .
H11A H -0.175(2) 0.452(2) 0.4049(19) 0.054(5) Uiso 1 1 d . . . . .
H11B H -0.335(3) 0.3627(19) 0.500(2) 0.058(5) Uiso 1 1 d . . . . .
H11C H -0.229(2) 0.3309(19) 0.368(2) 0.055(5) Uiso 1 1 d . . . . .
C12 C 0.47203(15) 0.25818(13) 0.26561(13) 0.0306(3) Uani 1 1 d . . . . .
C13 C 0.46486(16) 0.38593(13) 0.27511(13) 0.0306(3) Uani 1 1 d . . . . .
H13 H 0.3879(18) 0.4093(14) 0.3493(15) 0.029(3) Uiso 1 1 d . . . . .
C14 C 0.57639(16) 0.49239(13) 0.17503(13) 0.0306(3) Uani 1 1 d . . . . .
C15 C 0.57308(18) 0.62316(14) 0.18534(14) 0.0358(3) Uani 1 1 d . . . . .
H15 H 0.489(2) 0.6433(15) 0.2594(17) 0.037(4) Uiso 1 1 d . . . . .
C16 C 0.68406(19) 0.72330(15) 0.08861(15) 0.0409(3) Uani 1 1 d . . . . .
H16 H 0.678(2) 0.8160(18) 0.0959(17) 0.047(4) Uiso 1 1 d . . . . .
C17 C 0.80326(19) 0.69581(16) -0.02192(15) 0.0432(4) Uani 1 1 d . . . . .
H17 H 0.885(2) 0.7696(19) -0.093(2) 0.057(5) Uiso 1 1 d . . . . .
C18 C 0.80873(19) 0.57120(16) -0.03519(15) 0.0410(3) Uani 1 1 d . . . . .
H18 H 0.891(2) 0.5482(17) -0.1086(18) 0.045(4) Uiso 1 1 d . . . . .
C19 C 0.69539(17) 0.46516(14) 0.06331(13) 0.0342(3) Uani 1 1 d . . . . .
C20 C 0.69774(19) 0.33361(15) 0.05402(15) 0.0399(3) Uani 1 1 d . . . . .
H20 H 0.779(2) 0.3181(18) -0.0248(19) 0.051(5) Uiso 1 1 d . . . . .
C21 C 0.59022(18) 0.23318(14) 0.15164(14) 0.0370(3) Uani 1 1 d . . . . .
H21 H 0.591(2) 0.1405(19) 0.1424(19) 0.055(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2223(16) . ?
O2 C6 1.2158(16) . ?
C1 C2 1.5177(18) . ?
C1 C12 1.4967(18) . ?
C2 C3 1.5504(17) . ?
C2 C8 1.5412(17) . ?
C2 C9 1.5638(18) . ?
C3 H3A 0.975(16) . ?
C3 H3B 1.001(16) . ?
C3 C4 1.5482(19) . ?
C4 H4 0.981(16) . ?
C4 C5 1.5342(19) . ?
C4 C9 1.5456(18) . ?
C5 H5 1.048(16) . ?
C5 C6 1.5224(18) . ?
C5 C10 1.529(2) . ?
C6 C7 1.5148(19) . ?
C7 H7 0.996(16) . ?
C7 C8 1.5402(18) . ?
C7 C11 1.5215(18) . ?
C8 H8A 0.993(16) . ?
C8 H8B 0.984(16) . ?
C9 H9A 1.010(16) . ?
C9 H9B 0.976(16) . ?
C10 H10A 1.057(19) . ?
C10 H10B 1.036(19) . ?
C10 H10C 1.01(2) . ?
C11 H11A 0.976(19) . ?
C11 H11B 0.98(2) . ?
C11 H11C 0.991(19) . ?
C12 C13 1.3728(18) . ?
C12 C21 1.4234(19) . ?
C13 H13 0.961(15) . ?
C13 C14 1.4224(18) . ?
C14 C15 1.4116(19) . ?
C14 C19 1.4183(19) . ?
C15 H15 0.969(16) . ?
C15 C16 1.3722(19) . ?
C16 H16 0.997(17) . ?
C16 C17 1.411(2) . ?
C17 H17 1.008(19) . ?
C17 C18 1.360(2) . ?
C18 H18 0.971(17) . ?
C18 C19 1.4230(19) . ?
C19 C20 1.416(2) . ?
C20 H20 0.974(18) . ?
C20 C21 1.362(2) . ?
C21 H21 1.011(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
O1 C1 C2 119.87(12) . . ?
O1 C1 C12 119.76(12) . . ?
C12 C1 C2 120.34(11) . . ?
C1 C2 C3 115.23(10) . . ?
C1 C2 C8 108.24(10) . . ?
C1 C2 C9 117.78(10) . . ?
C3 C2 C9 87.54(9) . . ?
C8 C2 C3 112.89(10) . . ?
C8 C2 C9 114.15(10) . . ?
C2 C3 H3A 110.6(9) . . ?
C2 C3 H3B 116.6(9) . . ?
H3A C3 H3B 108.8(12) . . ?
C4 C3 C2 88.95(9) . . ?
C4 C3 H3A 111.3(9) . . ?
C4 C3 H3B 119.3(9) . . ?
C3 C4 H4 114.0(9) . . ?
C5 C4 C3 118.18(12) . . ?
C5 C4 H4 107.6(9) . . ?
C5 C4 C9 112.36(10) . . ?
C9 C4 C3 88.27(10) . . ?
C9 C4 H4 115.7(9) . . ?
C4 C5 H5 109.0(9) . . ?
C6 C5 C4 114.32(11) . . ?
C6 C5 H5 105.3(8) . . ?
C6 C5 C10 109.06(12) . . ?
C10 C5 C4 112.71(12) . . ?
C10 C5 H5 105.8(8) . . ?
O2 C6 C5 119.45(12) . . ?
O2 C6 C7 121.59(12) . . ?
C7 C6 C5 118.89(11) . . ?
C6 C7 H7 107.1(9) . . ?
C6 C7 C8 111.87(10) . . ?
C6 C7 C11 112.43(12) . . ?
C8 C7 H7 107.5(9) . . ?
C11 C7 H7 109.2(9) . . ?
C11 C7 C8 108.62(11) . . ?
C2 C8 H8A 110.3(9) . . ?
C2 C8 H8B 108.9(9) . . ?
C7 C8 C2 117.18(10) . . ?
C7 C8 H8A 106.8(9) . . ?
C7 C8 H8B 106.2(9) . . ?
H8A C8 H8B 107.0(13) . . ?
C2 C9 H9A 117.5(9) . . ?
C2 C9 H9B 110.7(9) . . ?
C4 C9 C2 88.55(9) . . ?
C4 C9 H9A 115.8(9) . . ?
C4 C9 H9B 110.6(9) . . ?
H9A C9 H9B 111.7(13) . . ?
C5 C10 H10A 110.8(10) . . ?
C5 C10 H10B 109.7(10) . . ?
C5 C10 H10C 107.5(11) . . ?
H10A C10 H10B 106.6(14) . . ?
H10A C10 H10C 111.4(14) . . ?
H10B C10 H10C 110.9(15) . . ?
C7 C11 H11A 110.7(11) . . ?
C7 C11 H11B 113.3(11) . . ?
C7 C11 H11C 110.0(11) . . ?
H11A C11 H11B 106.3(15) . . ?
H11A C11 H11C 109.6(15) . . ?
H11B C11 H11C 106.9(15) . . ?
C13 C12 C1 123.02(12) . . ?
C13 C12 C21 119.32(12) . . ?
C21 C12 C1 117.66(12) . . ?
C12 C13 H13 123.3(8) . . ?
C12 C13 C14 121.14(12) . . ?
C14 C13 H13 115.5(8) . . ?
C15 C14 C13 121.71(12) . . ?
C15 C14 C19 119.43(12) . . ?
C19 C14 C13 118.86(12) . . ?
C14 C15 H15 119.6(9) . . ?
C16 C15 C14 120.52(13) . . ?
C16 C15 H15 119.8(9) . . ?
C15 C16 H16 119.6(10) . . ?
C15 C16 C17 120.03(14) . . ?
C17 C16 H16 120.3(10) . . ?
C16 C17 H17 119.7(11) . . ?
C18 C17 C16 120.82(13) . . ?
C18 C17 H17 119.5(11) . . ?
C17 C18 H18 122.8(10) . . ?
C17 C18 C19 120.56(14) . . ?
C19 C18 H18 116.6(10) . . ?
C14 C19 C18 118.64(13) . . ?
C20 C19 C14 118.97(12) . . ?
C20 C19 C18 122.39(13) . . ?
C19 C20 H20 117.5(10) . . ?
C21 C20 C19 121.01(13) . . ?
C21 C20 H20 121.5(10) . . ?
C12 C21 H21 119.2(10) . . ?
C20 C21 C12 120.68(13) . . ?
C20 C21 H21 120.1(10) . . ?

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
O1 C1 C2 C3 20.29(18) . . . . ?
O1 C1 C2 C8 -107.15(13) . . . . ?
O1 C1 C2 C9 121.52(14) . . . . ?
O1 C1 C12 C13 -177.75(12) . . . . ?
O1 C1 C12 C21 3.19(19) . . . . ?
O2 C6 C7 C8 107.85(14) . . . . ?
O2 C6 C7 C11 -14.70(17) . . . . ?
C1 C2 C3 C4 139.01(11) . . . . ?
C1 C2 C8 C7 161.02(11) . . . . ?
C1 C2 C9 C4 -136.71(11) . . . . ?
C1 C12 C13 C14 179.35(11) . . . . ?
C1 C12 C21 C20 -179.68(12) . . . . ?
C2 C1 C12 C13 4.22(19) . . . . ?
C2 C1 C12 C21 -174.84(11) . . . . ?
C2 C3 C4 C5 95.02(12) . . . . ?
C2 C3 C4 C9 -19.53(10) . . . . ?
C3 C2 C8 C7 32.25(15) . . . . ?
C3 C2 C9 C4 -19.34(9) . . . . ?
C3 C4 C5 C6 -59.27(16) . . . . ?
C3 C4 C5 C10 66.01(15) . . . . ?
C3 C4 C9 C2 19.36(9) . . . . ?
C4 C5 C6 O2 -134.40(13) . . . . ?
C4 C5 C6 C7 48.60(16) . . . . ?
C5 C4 C9 C2 -100.54(12) . . . . ?
C5 C6 C7 C8 -75.22(14) . . . . ?
C5 C6 C7 C11 162.24(12) . . . . ?
C6 C7 C8 C2 53.21(15) . . . . ?
C8 C2 C3 C4 -95.93(12) . . . . ?
C8 C2 C9 C4 94.70(11) . . . . ?
C9 C2 C3 C4 19.31(10) . . . . ?
C9 C2 C8 C7 -65.70(14) . . . . ?
C9 C4 C5 C6 41.30(16) . . . . ?
C9 C4 C5 C10 166.57(12) . . . . ?
C10 C5 C6 O2 98.43(15) . . . . ?
C10 C5 C6 C7 -78.58(15) . . . . ?
C11 C7 C8 C2 177.90(11) . . . . ?
C12 C1 C2 C3 -161.68(11) . . . . ?
C12 C1 C2 C8 70.88(14) . . . . ?
C12 C1 C2 C9 -60.45(15) . . . . ?
C12 C13 C14 C15 -178.50(12) . . . . ?
C12 C13 C14 C19 0.58(18) . . . . ?
C13 C12 C21 C20 1.2(2) . . . . ?
C13 C14 C15 C16 178.91(12) . . . . ?
C13 C14 C19 C18 -178.91(12) . . . . ?
C13 C14 C19 C20 0.83(18) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C14 C19 C20 C21 -1.2(2) . . . . ?
C15 C14 C19 C18 0.20(18) . . . . ?
C15 C14 C19 C20 179.94(12) . . . . ?
C15 C16 C17 C18 0.8(2) . . . . ?
C16 C17 C18 C19 -0.7(2) . . . . ?
C17 C18 C19 C14 0.3(2) . . . . ?
C17 C18 C19 C20 -179.47(13) . . . . ?
C18 C19 C20 C21 178.51(13) . . . . ?
C19 C14 C15 C16 -0.2(2) . . . . ?
C19 C20 C21 C12 0.2(2) . . . . ?
C21 C12 C13 C14 -1.61(19) . . . . ?

_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.814
_oxdiff_exptl_absorpt_empirical_full_min 0.519
