# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_2023-1228-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2337021'
loop_
_audit_author_name
_audit_author_address
'Yuanfei Zhang'
;Nanning Normal University
China
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-08-27 downloaded from the CCDC.
;
_audit_creation_date             2024-01-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
6,6-dimethyl-5,6,7,8-tetrahydrophenanthren-9-ol
_chemical_formula_moiety         'C16 H18 O'
_chemical_formula_sum            'C16 H18 O'
_chemical_formula_weight         226.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHON
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        P21/c
_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                   10.3791(2)
_cell_length_b                   18.0337(4)
_cell_length_c                   7.18597(15)
_cell_angle_alpha                90
_cell_angle_beta                 109.003(2)
_cell_angle_gamma                90
_cell_volume                     1271.73(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5144
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2150
_cell_measurement_theta_min      4.8770
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.809
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8018
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.482
_diffrn_reflns_theta_min         4.506
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  22.00   0.50    0.09    --   48.99 -19.00-120.00   94
  2  ω    -11.00  24.00   0.50    0.09    --   48.99 -19.00 -90.00   70
  3  ω     39.00  66.00   0.50    0.09    --   48.99-134.00-177.00   54
  4  ω     54.00  91.00   0.50    0.35    --  107.94 -95.00-150.00   74
  5  ω     67.00  92.00   0.50    0.35    --  107.94 -95.00-120.00   50
  6  ω     43.00 102.00   0.50    0.09    --   48.99-135.00   3.00  118
  7  ω    -21.00  26.00   0.50    0.09    --   48.99 -19.00 150.00   94
  8  ω     48.00 104.00   0.50    0.35    --  107.94 -95.00  30.00  112
  9  ω     38.00  64.00   0.50    0.35    --  107.94 -61.00  60.00   52
 10  ω     35.00  67.00   0.50    0.35    --  107.94 -61.00  30.00   64
 11  ω     38.00  70.00   0.50    0.35    --  107.94 -61.00 -30.00   64
 12  ω     95.00 171.00   0.50    0.35    --  107.94  45.00  60.00  152
 13  ω     98.00 123.00   0.50    0.35    --  107.94 135.00  68.00   50
 14  ω     70.00 104.00   0.50    0.09    --   48.99 135.00  68.00   68
 15  ω    111.00 157.00   0.50    0.35    --  107.94  30.00-120.00   92
 16  ω     70.00  95.00   0.50    0.09    --   48.99 134.00-110.00   50
 17  ω     80.00 119.00   0.50    0.09    --   48.99 125.00-120.00   78
 18  ω    -64.00 -32.00   0.50    0.35    -- -105.44  61.00 -60.00   64
 19  ω   -116.00 -74.00   0.50    0.35    -- -105.44 134.00-110.00   84
 20  ω    -68.00 -42.00   0.50    0.35    -- -105.44 134.00-110.00   52
 21  ω   -118.00 -85.00   0.50    0.35    -- -105.44 135.00  68.00   66
 22  ω    -84.00 -59.00   0.50    0.09    --  -46.49 135.00  68.00   50
 23  ω   -177.00-132.00   0.50    0.35    -- -105.44 -61.00  90.00   90
 24  ω   -152.00 -67.00   0.50    0.35    -- -105.44-135.00   3.00  170
 25  ω   -113.00 -88.00   0.50    0.35    -- -105.44 -61.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0927851000
_diffrn_orient_matrix_UB_12      -0.0688249000
_diffrn_orient_matrix_UB_13      -0.0494294000
_diffrn_orient_matrix_UB_21      0.1264916000
_diffrn_orient_matrix_UB_22      -0.0505522000
_diffrn_orient_matrix_UB_23      0.0660723000
_diffrn_orient_matrix_UB_31      -0.0063655000
_diffrn_orient_matrix_UB_32      -0.0003383000
_diffrn_orient_matrix_UB_33      0.2112637000
_diffrn_oxdiff_digest_frames     
;
019c637913c37df57617f17e501d118b1500074e149
;
_diffrn_oxdiff_digest_hkl        
;
01b419f5b9325381ec64a182345d9ede83d7e1
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2166
_reflns_number_total             2560
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.43.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_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    ?
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0083(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.053
_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)+(0.0683P)²+0.1160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1266
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.00110(10) 0.19254(6) 0.88214(12) 0.0669(3) Uani 1 1 d . . . . .
H1 H -0.057456 0.214601 0.919140 0.100 Uiso 1 1 calc GR . . . .
C1 C -0.19248(12) 0.18539(7) 0.58480(18) 0.0556(3) Uani 1 1 d . . . . .
H1A H -0.247832 0.209696 0.644290 0.067 Uiso 1 1 calc R . . . .
C2 C -0.01958(11) 0.11422(6) 0.40840(15) 0.0443(3) Uani 1 1 d . . . . .
C3 C -0.24641(11) 0.16269(7) 0.38615(18) 0.0518(3) Uani 1 1 d . . . . .
C4 C -0.15976(11) 0.12777(6) 0.29492(16) 0.0468(3) Uani 1 1 d . . . . .
C5 C -0.21737(12) 0.10648(8) 0.09501(18) 0.0567(3) Uani 1 1 d . . . . .
H5 H -0.162502 0.083791 0.031973 0.068 Uiso 1 1 calc R . . . .
C6 C 0.02883(11) 0.13470(6) 0.60397(16) 0.0469(3) Uani 1 1 d . . . . .
C7 C 0.22575(11) 0.08782(6) 0.42098(17) 0.0514(3) Uani 1 1 d . . . . .
C8 C -0.05956(12) 0.17168(7) 0.68903(16) 0.0517(3) Uani 1 1 d . . . . .
C9 C 0.07337(11) 0.07700(7) 0.31250(16) 0.0507(3) Uani 1 1 d . . . . .
H9A H 0.052446 0.096089 0.179742 0.061 Uiso 1 1 calc R . . . .
H9B H 0.053831 0.024275 0.302676 0.061 Uiso 1 1 calc R . . . .
C10 C 0.17386(13) 0.12105(8) 0.73193(18) 0.0587(3) Uani 1 1 d . . . . .
H10A H 0.173595 0.099483 0.855458 0.070 Uiso 1 1 calc R . . . .
H10B H 0.221173 0.168193 0.761276 0.070 Uiso 1 1 calc R . . . .
C11 C 0.25146(13) 0.06996(7) 0.63780(18) 0.0588(3) Uani 1 1 d . . . . .
H11A H 0.224610 0.019092 0.649300 0.071 Uiso 1 1 calc R . . . .
H11B H 0.348229 0.074159 0.708747 0.071 Uiso 1 1 calc R . . . .
C12 C -0.35186(13) 0.11861(10) -0.0070(2) 0.0710(4) Uani 1 1 d . . . . .
H12 H -0.387309 0.103955 -0.137929 0.085 Uiso 1 1 calc R . . . .
C13 C -0.43678(13) 0.15293(10) 0.0839(2) 0.0753(4) Uani 1 1 d . . . . .
H13 H -0.528229 0.160940 0.013508 0.090 Uiso 1 1 calc R . . . .
C14 C -0.38530(12) 0.17452(9) 0.2752(2) 0.0666(4) Uani 1 1 d . . . . .
H14 H -0.442233 0.197468 0.334398 0.080 Uiso 1 1 calc R . . . .
C15 C 0.30662(14) 0.03455(9) 0.3360(2) 0.0714(4) Uani 1 1 d . . . . .
H15A H 0.284920 -0.015636 0.359072 0.107 Uiso 1 1 calc GR . . . .
H15B H 0.402366 0.042952 0.398506 0.107 Uiso 1 1 calc GR . . . .
H15C H 0.283392 0.042851 0.196970 0.107 Uiso 1 1 calc GR . . . .
C16 C 0.26668(14) 0.16741(8) 0.3942(2) 0.0683(4) Uani 1 1 d . . . . .
H16A H 0.258191 0.175508 0.258711 0.103 Uiso 1 1 calc GR . . . .
H16B H 0.359420 0.175578 0.475086 0.103 Uiso 1 1 calc GR . . . .
H16C H 0.208162 0.201194 0.432082 0.103 Uiso 1 1 calc GR . . . .


_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 C8 1.3737(14) . ?
C1 C3 1.4136(17) . ?
C1 C8 1.3611(17) . ?
C2 C4 1.4384(15) . ?
C2 C6 1.3799(15) . ?
C2 C9 1.5129(15) . ?
C3 C4 1.4210(16) . ?
C3 C14 1.4180(17) . ?
C4 C5 1.4175(16) . ?
C5 C12 1.3666(18) . ?
C6 C8 1.4231(16) . ?
C6 C10 1.5068(16) . ?
C7 C9 1.5311(15) . ?
C7 C11 1.5271(17) . ?
C7 C15 1.5279(17) . ?
C7 C16 1.5266(18) . ?
C10 C11 1.5199(18) . ?
C12 C13 1.401(2) . ?
C13 C14 1.360(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
C8 C1 C3 120.02(11) . . ?
C4 C2 C9 119.64(9) . . ?
C6 C2 C4 119.84(10) . . ?
C6 C2 C9 120.53(10) . . ?
C1 C3 C4 119.49(11) . . ?
C1 C3 C14 121.33(11) . . ?
C14 C3 C4 119.18(11) . . ?
C3 C4 C2 119.28(10) . . ?
C5 C4 C2 122.92(10) . . ?
C5 C4 C3 117.78(10) . . ?
C12 C5 C4 121.36(12) . . ?
C2 C6 C8 119.41(10) . . ?
C2 C6 C10 122.54(10) . . ?
C8 C6 C10 118.04(10) . . ?
C11 C7 C9 107.51(10) . . ?
C11 C7 C15 109.81(10) . . ?
C15 C7 C9 109.10(10) . . ?
C16 C7 C9 109.84(10) . . ?
C16 C7 C11 111.31(11) . . ?
C16 C7 C15 109.22(11) . . ?
O1 C8 C6 115.33(10) . . ?
C1 C8 O1 122.77(11) . . ?
C1 C8 C6 121.90(10) . . ?
C2 C9 C7 114.69(9) . . ?
C6 C10 C11 113.35(10) . . ?
C10 C11 C7 112.60(10) . . ?
C5 C12 C13 120.57(12) . . ?
C14 C13 C12 119.89(12) . . ?
C13 C14 C3 121.21(12) . . ?

_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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.581
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and hexane'
####################################################################### 
# 
# 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_2023-1228-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2337023'
loop_
_audit_author_name
_audit_author_address
'Yuanfei Zhang'
;Nanning Normal University
China
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-08-27 downloaded from the CCDC.
;
_audit_creation_date             2024-01-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        'steroid 11-carboxylate'
_chemical_formula_moiety         'C29 H35 F3 O5'
_chemical_formula_sum            'C29 H35 F3 O5'
_chemical_formula_weight         520.57
_chemical_absolute_configuration 0.03(8)
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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'
F F 0.0727 0.0534 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.5004(2)
_cell_length_b                   16.0195(2)
_cell_length_c                   16.1548(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2717.41(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6377
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7660
_cell_measurement_theta_min      3.8750
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.732
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10038
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.010
_diffrn_reflns_theta_min         3.886
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -176.00-147.00   0.50    0.29    -- -105.44 -45.00  60.00   58
  2  ω   -138.00-109.00   0.50    0.29    -- -105.44 -45.00  60.00   58
  3  ω   -103.00 -29.00   0.50    0.07    --  -46.49 -12.00  95.00  148
  4  ω    -78.00 -37.00   0.50    0.29    -- -105.44 117.00  63.00   82
  5  ω    -89.00 -27.00   0.50    0.07    --  -46.49 125.00  60.00  124
  6  ω     44.00  69.00   0.50    0.29    --  107.94 -61.00 -90.00   50
  7  ω     88.00 173.00   0.50    0.29    --  107.94  12.00 -92.00  170
  8  ω     36.00  62.00   0.50    0.29    --  107.94 -61.00 -60.00   52
  9  ω    -26.00  26.00   0.50    0.07    --   48.99 -19.00 150.00  104
 10  ω     81.00 110.00   0.50    0.29    --  107.94-125.00  30.00   58
 11  ω     51.00 111.00   0.50    0.29    --  107.94-125.00  90.00  120
 12  ω     54.00 104.00   0.50    0.29    --  107.94-128.00-107.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0496223000
_diffrn_orient_matrix_UB_12      -0.0154480000
_diffrn_orient_matrix_UB_13      0.0883819000
_diffrn_orient_matrix_UB_21      -0.1378619000
_diffrn_orient_matrix_UB_22      -0.0004569000
_diffrn_orient_matrix_UB_23      0.0326934000
_diffrn_orient_matrix_UB_31      -0.0072611000
_diffrn_orient_matrix_UB_32      -0.0949414000
_diffrn_orient_matrix_UB_33      -0.0145349000
_diffrn_oxdiff_digest_frames     
;
01c174bae33b43677aa3a12614fd5af8b0000420204
;
_diffrn_oxdiff_digest_hkl        
;
018b132c546588e9e3c01113008e065fcb0366
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_full    0.834
_reflns_Friedel_fraction_max     0.763
_reflns_number_gt                4307
_reflns_number_total             4988
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.43.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1495 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4988
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.063
_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)+(0.0979P)²+0.0264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1456
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C28, C29
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Ternary CH refined with riding coordinates:
 C14(H14), C16(H16), C19(H19), C25(H25)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B), C17(H17A,H17B), C21(H21A,H21B), C22(H22A,
 H22B), C24(H24A,H24B), C26(H26A,H26B), C28(H28A,H28B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C), C29(H29A,H29B,
 H29C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F1 F 0.8266(3) 1.02621(12) 0.67804(16) 0.0885(7) Uani 1 1 d . . . . .
F2 F 0.9309(2) 0.91513(15) 0.69889(18) 0.0902(7) Uani 1 1 d . . . . .
O1 O 0.4604(3) 0.11434(12) 0.58455(15) 0.0680(6) Uani 1 1 d . . . . .
O2 O 0.4065(2) 0.94594(12) 0.57608(18) 0.0711(6) Uani 1 1 d . . . . .
H2 H 0.415659 0.996306 0.582938 0.107 Uiso 1 1 calc GR . . . .
F3 F 0.8084(3) 0.96225(15) 0.79302(14) 0.0883(7) Uani 1 1 d . . . . .
O3 O 0.8800(2) 0.72793(16) 0.66608(16) 0.0726(6) Uani 1 1 d . . . . .
O4 O 0.5378(3) 0.22256(13) 0.51580(16) 0.0823(8) Uani 1 1 d . . . . .
O5 O 0.8361(3) 0.77015(17) 0.79525(16) 0.0836(8) Uani 1 1 d . . . . .
C1 C 0.5946(3) 0.77169(16) 0.65258(17) 0.0503(6) Uani 1 1 d . . . . .
C2 C 0.5840(3) 0.67862(16) 0.65591(18) 0.0503(6) Uani 1 1 d . . . . .
C3 C 0.5040(3) 0.14452(18) 0.5223(2) 0.0621(7) Uani 1 1 d . . . . .
C4 C 0.4977(3) 0.81736(17) 0.61522(19) 0.0538(6) Uani 1 1 d . . . . .
C5 C 0.7091(3) 0.90117(17) 0.67795(18) 0.0533(6) Uani 1 1 d . . . . .
C6 C 0.7023(3) 0.81403(17) 0.68380(17) 0.0519(6) Uani 1 1 d . . . . .
C7 C 0.8185(4) 0.95051(18) 0.7115(2) 0.0623(7) Uani 1 1 d . . . . .
C8 C 0.5063(3) 0.90452(17) 0.61110(19) 0.0563(7) Uani 1 1 d . . . . .
C9 C 0.6110(3) 0.94577(16) 0.6419(2) 0.0575(7) Uani 1 1 d . . . . .
H9 H 0.615793 1.003637 0.638526 0.069 Uiso 1 1 calc R . . . .
C10 C 0.5759(4) 0.65595(17) 0.50246(19) 0.0595(7) Uani 1 1 d . . . . .
H10A H 0.603460 0.713060 0.500533 0.089 Uiso 1 1 calc GR . . . .
H10B H 0.518581 0.645317 0.457398 0.089 Uiso 1 1 calc GR . . . .
H10C H 0.648526 0.619801 0.497929 0.089 Uiso 1 1 calc GR . . . .
C11 C 0.6308(4) 0.63379(17) 0.71746(19) 0.0607(7) Uani 1 1 d . . . . .
H11 H 0.663983 0.662076 0.762877 0.073 Uiso 1 1 calc R . . . .
C12 C 0.4147(4) 0.40604(19) 0.5327(3) 0.0718(9) Uani 1 1 d . . . . .
H12A H 0.349348 0.394919 0.573719 0.086 Uiso 1 1 calc R . . . .
H12B H 0.387989 0.381287 0.480726 0.086 Uiso 1 1 calc R . . . .
C13 C 0.5404(4) 0.36730(17) 0.5604(2) 0.0636(8) Uani 1 1 d . . . . .
C14 C 0.5782(4) 0.40780(17) 0.6423(2) 0.0622(7) Uani 1 1 d . . . . .
H14 H 0.504332 0.401934 0.678904 0.075 Uiso 1 1 calc R . . . .
C15 C 0.6339(4) 0.53992(18) 0.7187(2) 0.0674(8) Uani 1 1 d . . . . .
H15A H 0.572948 0.519918 0.759237 0.081 Uiso 1 1 calc R . . . .
H15B H 0.717872 0.521662 0.736098 0.081 Uiso 1 1 calc R . . . .
C16 C 0.4854(3) 0.54463(16) 0.5994(2) 0.0567(7) Uani 1 1 d . . . . .
H16 H 0.419213 0.540743 0.641986 0.068 Uiso 1 1 calc R . . . .
C17 C 0.3765(3) 0.68326(18) 0.5874(2) 0.0634(8) Uani 1 1 d . . . . .
H17A H 0.322556 0.659720 0.544579 0.076 Uiso 1 1 calc R . . . .
H17B H 0.336873 0.671733 0.640360 0.076 Uiso 1 1 calc R . . . .
C18 C 0.5079(3) 0.63949(16) 0.58445(18) 0.0509(6) Uani 1 1 d . . . . .
C19 C 0.6035(3) 0.50134(16) 0.6354(2) 0.0569(7) Uani 1 1 d . . . . .
H19 H 0.675725 0.510368 0.598037 0.068 Uiso 1 1 calc R . . . .
C20 C 0.5257(5) 0.0977(2) 0.4434(3) 0.0857(12) Uani 1 1 d . . . . .
H20A H 0.601874 0.064897 0.448121 0.129 Uiso 1 1 calc GR . . . .
H20B H 0.534719 0.136564 0.398512 0.129 Uiso 1 1 calc GR . . . .
H20C H 0.454513 0.061654 0.432879 0.129 Uiso 1 1 calc GR . . . .
C21 C 0.3837(3) 0.77708(18) 0.5753(2) 0.0624(7) Uani 1 1 d . . . . .
H21A H 0.385442 0.788961 0.516461 0.075 Uiso 1 1 calc R . . . .
H21B H 0.307122 0.802148 0.597895 0.075 Uiso 1 1 calc R . . . .
C22 C 0.4309(4) 0.50132(19) 0.5218(2) 0.0730(9) Uani 1 1 d . . . . .
H22A H 0.487305 0.511710 0.475394 0.088 Uiso 1 1 calc R . . . .
H22B H 0.348828 0.525750 0.508784 0.088 Uiso 1 1 calc R . . . .
C23 C 0.8120(3) 0.76868(17) 0.7227(2) 0.0611(7) Uani 1 1 d . . . . .
C24 C 0.6399(6) 0.2629(2) 0.6490(3) 0.0906(13) Uani 1 1 d . . . . .
H24A H 0.709896 0.234468 0.621758 0.109 Uiso 1 1 calc R . . . .
H24B H 0.612554 0.229436 0.695850 0.109 Uiso 1 1 calc R . . . .
C25 C 0.5291(4) 0.27630(18) 0.5885(2) 0.0710(9) Uani 1 1 d . . . . .
H25 H 0.447688 0.267416 0.616730 0.085 Uiso 1 1 calc R . . . .
C26 C 0.6815(5) 0.3504(2) 0.6780(3) 0.0791(10) Uani 1 1 d . . . . .
H26A H 0.683830 0.353671 0.737885 0.095 Uiso 1 1 calc R . . . .
H26B H 0.764762 0.364614 0.656163 0.095 Uiso 1 1 calc R . . . .
C27 C 0.6441(5) 0.3751(2) 0.4939(3) 0.0819(11) Uani 1 1 d . . . . .
H27A H 0.613597 0.351868 0.442809 0.123 Uiso 1 1 calc GR . . . .
H27B H 0.718763 0.345298 0.511379 0.123 Uiso 1 1 calc GR . . . .
H27C H 0.664855 0.432862 0.485893 0.123 Uiso 1 1 calc GR . . . .
C28 C 0.9846(6) 0.6779(4) 0.6975(4) 0.1155(18) Uani 1 1 d . U . . .
H28A H 1.054235 0.713510 0.715052 0.139 Uiso 1 1 calc R . . . .
H28B H 0.956824 0.644883 0.744501 0.139 Uiso 1 1 calc R . . . .
C29 C 1.0252(10) 0.6239(5) 0.6305(6) 0.165(3) Uani 1 1 d . U . . .
H29A H 1.068884 0.656350 0.589432 0.247 Uiso 1 1 calc GR . . . .
H29B H 0.952137 0.597692 0.606021 0.247 Uiso 1 1 calc GR . . . .
H29C H 1.081550 0.581818 0.651775 0.247 Uiso 1 1 calc GR . . . .


_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
F1 C7 1.330(4) . ?
F2 C7 1.325(5) . ?
O1 C3 1.206(4) . ?
O2 C8 1.363(4) . ?
F3 C7 1.334(4) . ?
O3 C23 1.332(4) . ?
O3 C28 1.451(5) . ?
O4 C3 1.304(4) . ?
O4 C25 1.458(4) . ?
O5 C23 1.199(4) . ?
C1 C2 1.496(3) . ?
C1 C4 1.392(4) . ?
C1 C6 1.411(4) . ?
C2 C11 1.322(4) . ?
C2 C18 1.538(4) . ?
C3 C20 1.496(5) . ?
C4 C8 1.401(4) . ?
C4 C21 1.505(4) . ?
C5 C6 1.401(4) . ?
C5 C7 1.497(4) . ?
C5 C9 1.382(5) . ?
C6 C23 1.500(4) . ?
C8 C9 1.376(5) . ?
C10 C18 1.528(4) . ?
C11 C15 1.504(4) . ?
C12 C13 1.526(6) . ?
C12 C22 1.546(4) . ?
C13 C14 1.527(5) . ?
C13 C25 1.531(4) . ?
C13 C27 1.535(5) . ?
C14 C19 1.526(4) . ?
C14 C26 1.534(5) . ?
C15 C19 1.515(5) . ?
C16 C18 1.557(3) . ?
C16 C19 1.535(5) . ?
C16 C22 1.543(5) . ?
C17 C18 1.548(4) . ?
C17 C21 1.517(4) . ?
C24 C25 1.536(7) . ?
C24 C26 1.540(5) . ?
C28 C29 1.450(9) . ?

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
C23 O3 C28 115.9(4) . . ?
C3 O4 C25 119.0(3) . . ?
C4 C1 C2 119.0(3) . . ?
C4 C1 C6 119.2(2) . . ?
C6 C1 C2 121.7(3) . . ?
C1 C2 C18 114.7(2) . . ?
C11 C2 C1 122.7(3) . . ?
C11 C2 C18 122.5(2) . . ?
O1 C3 O4 123.7(3) . . ?
O1 C3 C20 124.6(3) . . ?
O4 C3 C20 111.7(3) . . ?
C1 C4 C8 119.8(3) . . ?
C1 C4 C21 122.8(2) . . ?
C8 C4 C21 117.3(3) . . ?
C6 C5 C7 122.8(3) . . ?
C9 C5 C6 120.4(3) . . ?
C9 C5 C7 116.9(2) . . ?
C1 C6 C23 122.1(2) . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 C23 118.1(3) . . ?
F1 C7 F3 106.1(3) . . ?
F1 C7 C5 112.5(3) . . ?
F2 C7 F1 105.7(3) . . ?
F2 C7 F3 106.4(3) . . ?
F2 C7 C5 113.7(2) . . ?
F3 C7 C5 111.8(3) . . ?
O2 C8 C4 117.1(3) . . ?
O2 C8 C9 122.0(2) . . ?
C9 C8 C4 120.8(3) . . ?
C8 C9 C5 120.0(2) . . ?
C2 C11 C15 124.2(3) . . ?
C13 C12 C22 109.8(3) . . ?
C12 C13 C14 107.8(3) . . ?
C12 C13 C25 114.0(3) . . ?
C12 C13 C27 112.1(3) . . ?
C14 C13 C25 99.6(3) . . ?
C14 C13 C27 112.8(3) . . ?
C25 C13 C27 109.8(3) . . ?
C13 C14 C26 104.7(3) . . ?
C19 C14 C13 113.5(3) . . ?
C19 C14 C26 119.6(3) . . ?
C11 C15 C19 113.0(3) . . ?
C19 C16 C18 112.2(2) . . ?
C19 C16 C22 113.9(3) . . ?
C22 C16 C18 111.7(2) . . ?
C21 C17 C18 113.6(3) . . ?
C2 C18 C16 111.1(2) . . ?
C2 C18 C17 104.8(2) . . ?
C10 C18 C2 109.7(2) . . ?
C10 C18 C16 112.0(2) . . ?
C10 C18 C17 111.4(3) . . ?
C17 C18 C16 107.6(2) . . ?
C14 C19 C16 109.3(3) . . ?
C15 C19 C14 111.9(3) . . ?
C15 C19 C16 108.8(3) . . ?
C4 C21 C17 114.2(3) . . ?
C16 C22 C12 113.1(3) . . ?
O3 C23 C6 111.2(3) . . ?
O5 C23 O3 124.6(3) . . ?
O5 C23 C6 124.2(3) . . ?
C25 C24 C26 106.3(3) . . ?
O4 C25 C13 108.6(3) . . ?
O4 C25 C24 112.5(3) . . ?
C13 C25 C24 105.3(3) . . ?
C14 C26 C24 103.4(4) . . ?
C29 C28 O3 106.9(5) . . ?

_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 1.154
_oxdiff_exptl_absorpt_empirical_full_min 0.846
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and hexane'
