# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_huochenyu_1122_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2bw59q
_database_code_depnum_ccdc_archive 'CCDC 2171063'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2SC04229K 2022
loop_
_audit_author_name
_audit_author_address
'chenyu huo'
;Lan Zhou University
China
;
_audit_update_record             
;
2022-05-06 deposited with the CCDC.	2022-11-16 downloaded from the CCDC.
;
_audit_creation_date             2021-11-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 O2'
_chemical_formula_sum            'C20 H26 O2'
_chemical_formula_weight         298.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.2191(2)
_cell_length_b                   11.57240(10)
_cell_length_c                   14.8457(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.8010(10)
_cell_angle_gamma                90
_cell_volume                     3469.50(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    31891
_cell_measurement_temperature    301.82(11)
_cell_measurement_theta_max      76.0630
_cell_measurement_theta_min      4.3630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            53861
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.229
_diffrn_reflns_theta_min         4.379
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.82(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00  49.00   0.50    0.05    --   46.32  77.00 -60.00   50
  2  ω     28.00  54.00   0.50    0.05    --   50.00  75.00-166.88   52
  3  ω     36.00  79.00   0.50    0.05    --   46.32  31.00 -57.00   86
  4  ω     84.00 118.00   0.50    0.05    --   46.32  31.00 -57.00   68
  5  ω     26.00  52.00   0.50    0.05    --   46.32  77.00 150.00   52
  6  ω     15.00  42.00   0.50    0.05    --   42.00  87.00-131.59   54
  7  ω     13.00  38.00   0.50    0.05    --   42.00  90.00  82.37   50
  8  ω    -20.00   6.00   0.50    0.05    --   14.00 101.00 160.22   52
  9  ω    -10.00  20.00   0.50    0.05    --   22.00  96.00  95.60   60
 10  ω    -30.00  -4.00   0.50    0.05    --   10.00 111.00-106.40   52
 11  ω     14.00  40.00   0.50    0.05    --   42.00  88.00 -20.51   52
 12  ω     92.00 126.00   0.50    0.05    --   54.00  77.00 -51.87   68
 13  ω     43.00  76.00   0.50    0.05    --   66.00  77.00-153.79   66
 14  ω     31.00  61.00   0.50    0.05    --   54.00  77.00 -51.87   60
 15  ω     44.00  69.00   0.50    0.05    --   66.00  76.00 -65.26   50
 16  ω     44.00  69.00   0.50    0.05    --   66.00  76.00   0.21   50
 17  ω     42.00  81.00   0.50    0.05    --   62.00  74.00 -24.19   78
 18  ω     36.00  63.00   0.50    0.05    --   58.00  75.00  71.17   54
 19  ω     33.00  59.00   0.50    0.05    --   54.00  74.00  40.97   52
 20  ω     35.00  61.00   0.50    0.05    --   58.00  77.00 103.00   52
 21  ω     47.00  73.00   0.50    0.05    --   66.00  73.00 119.88   52
 22  ω     32.00  58.00   0.50    0.05    --   54.00  75.00 167.13   52
 23  ω     42.00  75.00   0.50    0.05    --   62.00  73.00 177.49   66
 24  ω     82.00 108.00   0.50    0.05    --   54.00  75.00 167.13   52
 25  ω    113.00 139.00   0.50    0.12    --  104.25  31.00 -57.00   52
 26  ω     75.00 101.00   0.50    0.12    --  104.25 -77.00  30.00   52
 27  ω     38.00  69.00   0.50    0.12    --  104.25 -61.00  90.00   62
 28  ω     36.00  69.00   0.50    0.12    --  104.25 -77.00  30.00   66
 29  ω    -27.00  17.00   0.50    0.05    --   46.32 -31.00 142.00   88
 30  ω     43.00  68.00   0.50    0.12    --  104.25 -61.00 -60.00   50
 31  ω     40.00  72.00   0.50    0.12    --  104.25 -61.00 -90.00   64
 32  ω     32.00  73.00   0.50    0.12    --  104.25 -61.00-180.00   82
 33  ω     37.00 106.00   0.50    0.12    --  104.25 -94.00 -90.00  138
 34  ω     65.00 109.00   0.50    0.12    --  104.25-125.00-180.00   88
 35  ω     59.00 112.00   0.50    0.12    --  104.25-125.00-150.00  106
 36  ω     70.00 102.00   0.50    0.12    --  104.25 -94.00-180.00   64
 37  ω     66.00 111.00   0.50    0.12    --  104.25-125.00 -90.00   90
 38  ω     68.00 102.00   0.50    0.12    --  104.25 -94.00-120.00   68
 39  ω     32.00  57.00   0.50    0.12    --  104.25-125.00 -90.00   50
 40  ω     48.00 104.00   0.50    0.12    --  104.25 -94.00 -30.00  112
 41  ω     49.00 112.00   0.50    0.12    --  104.25-125.00  90.00  126
 42  ω     30.00  94.00   0.50    0.05    --   46.32-125.00   0.00  128
 43  ω    -10.00  19.00   0.50    0.05    --  -46.32  31.00 -57.00   58
 44  ω    -69.00 -30.00   0.50    0.05    --  -46.32  77.00  30.00   78
 45  ω    -24.00  20.00   0.50    0.05    --  -46.32  77.00  30.00   88
 46  ω    -58.00 -29.00   0.50    0.12    -- -102.00  61.00-150.00   58
 47  ω    -91.00 -30.00   0.50    0.12    -- -102.00  77.00-180.00  122
 48  ω    -64.00 -39.00   0.50    0.05    --  -62.00 -77.00-162.38   50
 49  ω   -170.00 -76.00   0.50    0.12    --  -98.00 -77.00 -96.56  188
 50  ω   -166.00-139.00   0.50    0.12    --  -94.00 -76.00   7.60   54
 51  ω   -168.00-106.00   0.50    0.12    --  -98.00 -77.00 103.38  124
 52  ω   -100.00 -75.00   0.50    0.12    --  -98.00 -77.00 103.38   50
 53  ω   -107.00 -72.00   0.50    0.12    --  -94.00 -76.00 169.24   70
 54  ω    -78.00 -51.00   0.50    0.05    --  -74.00 -76.00  39.13   54
 55  ω   -135.00 -71.00   0.50    0.12    --  -94.00 -76.00   7.60  128
 56  ω   -163.00 -79.00   0.50    0.12    -- -102.00 -77.00   0.00  168
 57  ω   -101.00 -76.00   0.50    0.12    --  -98.00 -76.00 -78.02   50
 58  ω    -89.00 -63.00   0.50    0.12    --  -86.00 -76.00-120.93   52
 59  ω    -71.00 -40.00   0.50    0.05    --  -62.00 -75.00-124.50   62
 60  ω   -161.00-111.00   0.50    0.12    --  -98.00 -76.00 -78.02  100
 61  ω    -80.00 -54.00   0.50    0.05    --  -74.00 -74.00  16.12   52
 62  ω    -89.00 -64.00   0.50    0.12    --  -86.00 -75.00 130.63   50
 63  ω    -83.00 -52.00   0.50    0.05    --  -74.00 -75.00 141.83   62
 64  ω   -123.00 -97.00   0.50    0.05    --  -74.00 -75.00 141.83   52
 65  ω   -159.00-110.00   0.50    0.12    --  -86.00 -74.00  83.87   98
 66  ω   -158.00-102.00   0.50    0.12    --  -86.00 -75.00 130.63  112
 67  ω    -86.00 -60.00   0.50    0.12    --  -82.00 -74.00 102.47   52
 68  ω    -77.00 -52.00   0.50    0.05    --  -74.00 -74.00  52.66   50
 69  ω   -125.00 -68.00   0.50    0.12    --  -90.00 -74.00  42.45  114
 70  ω   -154.00-129.00   0.50    0.12    --  -90.00 -74.00  42.45   50
 71  ω   -159.00-117.00   0.50    0.12    --  -90.00 -74.00 112.66   84
 72  ω    -96.00 -70.00   0.50    0.12    --  -90.00 -74.00 112.66   52
 73  ω    -89.00 -64.00   0.50    0.12    --  -86.00 -74.00  83.87   50
 74  ω   -160.00 -70.00   0.50    0.12    --  -90.00 -73.00 -38.42  180
 75  ω    -83.00 -53.00   0.50    0.05    --  -74.00 -73.00 -67.17   60
 76  ω   -102.00 -69.00   0.50    0.12    --  -90.00 -73.00-159.89   66
 77  ω    -81.00 -55.00   0.50    0.05    --  -74.00 -73.00-166.11   52
 78  ω    -91.00 -65.00   0.50    0.12    --  -86.00 -73.00 -75.28   52
 79  ω    -91.00 -58.00   0.50    0.12    --  -78.00 -73.00 -42.81   66
 80  ω   -125.00 -99.00   0.50    0.05    --  -74.00 -73.00 -67.17   52
 81  ω   -166.00-114.00   0.50    0.12    --  -94.00 -72.00-176.28  104
 82  ω   -151.00-125.00   0.50    0.12    --  -86.00 -73.00 -75.28   52
 83  ω    -96.00 -63.00   0.50    0.12    --  -82.00 -72.00 -98.21   66
 84  ω    -98.00 -61.00   0.50    0.12    --  -82.00 -72.00   2.69   74
 85  ω    -96.00 -70.00   0.50    0.12    --  -90.00 -73.00  52.49   52
 86  ω    -91.00 -58.00   0.50    0.12    --  -78.00 -73.00 137.24   66
 87  ω    -80.00 -54.00   0.50    0.05    --  -74.00 -72.00 157.80   52
 88  ω   -162.00 -69.00   0.50    0.12    --  -90.00 -73.00  30.45  186
 89  ω    -88.00 -62.00   0.50    0.12    --  -82.00 -71.00 -17.98   52
 90  ω    -95.00 -70.00   0.50    0.12    --  -90.00 -70.00 -23.15   50
 91  ω    -99.00 -73.00   0.50    0.12    --  -94.00 -72.00-176.28   52
 92  ω    -75.00 -47.00   0.50    0.05    --  -66.00 -70.00-158.94   56
 93  ω    -76.00 -50.00   0.50    0.05    --  -70.00 -70.00-144.43   52
 94  ω    -99.00 -71.00   0.50    0.12    --  -90.00 -68.00-159.32   56
 95  ω   -162.00-106.00   0.50    0.12    --  -90.00 -68.00-159.32  112
 96  ω   -100.00 -71.00   0.50    0.12    --  -90.00 -68.00-137.55   58
 97  ω    -85.00 -59.00   0.50    0.12    --  -78.00 -67.00 -88.40   52
 98  ω   -100.00 -75.00   0.50    0.12    --  -94.00 -67.00 -84.00   50
 99  ω   -167.00 -76.00   0.50    0.12    --  -94.00 -66.00 -50.18  182
100  ω   -153.00-127.00   0.50    0.12    --  -90.00 -70.00 -23.15   52
101  ω   -167.00 -76.00   0.50    0.12    --  -94.00 -64.00-151.18  182
102  ω    -83.00 -57.00   0.50    0.05    --  -74.00 -65.00  67.55   52
103  ω   -114.00 -72.00   0.50    0.12    --  -90.00 -64.00 108.53   84
104  ω   -111.00 -79.00   0.50    0.12    --  -94.00 -65.00 143.08   64
105  ω   -174.00 -82.00   0.50    0.12    -- -102.00 -69.00 140.11  184
106  ω   -152.00-127.00   0.50    0.12    --  -90.00 -54.00  47.20   50
107  ω   -144.00 -77.00   0.50    0.12    --  -94.00 -63.00  70.77  134
108  ω   -119.00 -76.00   0.50    0.12    --  -90.00 -54.00  47.20   86
109  ω   -161.00-131.00   0.50    0.12    -- -102.00 -31.00 142.00   60
110  ω   -101.00 -76.00   0.50    0.05    --  -46.32 -31.00 142.00   50
111  ω    -70.00 -37.00   0.50    0.05    --  -46.32 -37.00  60.00   66
112  ω   -103.00 -74.00   0.50    0.12    --  -90.00 -61.00-121.27   58
113  ω   -154.00-126.00   0.50    0.12    --  -90.00 -61.00-121.27   56
114  ω    -73.00 -34.00   0.50    0.12    -- -102.00 125.00 -30.00   78
115  ω    -80.00 -29.00   0.50    0.12    -- -102.00 144.00  27.81  102
116  ω   -126.00-101.00   0.50    0.12    -- -102.00 144.00  27.81   50
117  ω   -112.00 -80.00   0.50    0.12    -- -102.00 125.00 -30.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0396932000
_diffrn_orient_matrix_UB_12      0.1076016000
_diffrn_orient_matrix_UB_13      -0.0313752000
_diffrn_orient_matrix_UB_21      0.0644659000
_diffrn_orient_matrix_UB_22      0.0586491000
_diffrn_orient_matrix_UB_23      -0.0270406000
_diffrn_orient_matrix_UB_31      -0.0092653000
_diffrn_orient_matrix_UB_32      -0.0521547000
_diffrn_orient_matrix_UB_33      -0.0952505000
_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                3108
_reflns_number_total             3559
_reflns_odcompleteness_completeness 100.00
_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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3559
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.091
_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)+(0.0735P)²+0.7282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1319
_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. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C19)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: C5(0.3) H5A(0.3) H5B(0.3) H5C(0.3) C9(0.7) H9A(0.7) H9B(0.7)
 H9C(0.7) H15(0.7) H15A(0.3) C19(0.7) H19A(0.7) H19B(0.7) H19C(0.7) C21(0.3)
 H21A(0.3) H21B(0.3) H21C(0.3)
4.a Ternary CH refined with riding coordinates:
 C14(H14), C15(H15), C15(H15A)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C20(H20A,H20B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C13(H13), C18(H18)
4.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C5(H5A,H5B,H5C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C),
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
4.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.75737(4) 0.83390(8) 0.61765(6) 0.0599(3) Uani 1 1 d . . . . .
O2 O 0.64418(5) 0.53648(8) 0.46494(6) 0.0668(3) Uani 1 1 d . . . . .
H2 H 0.668459 0.582585 0.440706 0.100 Uiso 1 1 calc R U . . .
C1 C 0.63559(5) 0.72614(10) 0.66359(7) 0.0455(3) Uani 1 1 d . . . . .
C2 C 0.60313(10) 1.07358(15) 0.82761(15) 0.0896(5) Uani 1 1 d . . . . .
H2A H 0.582169 1.076823 0.768232 0.134 Uiso 1 1 calc R U . . .
H2B H 0.616481 1.149893 0.846199 0.134 Uiso 1 1 calc R U . . .
H2C H 0.572531 1.043235 0.869047 0.134 Uiso 1 1 calc R U . . .
C3 C 0.66434(7) 0.99473(13) 0.82659(10) 0.0672(4) Uani 1 1 d . . . . .
C4 C 0.72114(6) 0.88996(11) 0.66460(8) 0.0509(3) Uani 1 1 d . . . . .
C5 C 0.5213(4) 0.3594(7) 0.5520(7) 0.104(2) Uani 0.3 1 d . U P A 2
H5A H 0.493778 0.381954 0.599904 0.155 Uiso 0.3 1 calc R U P A 2
H5B H 0.514130 0.279186 0.538274 0.155 Uiso 0.3 1 calc R U P A 2
H5C H 0.510275 0.405092 0.499405 0.155 Uiso 0.3 1 calc R U P A 2
C6 C 0.64715(6) 0.68630(10) 0.57679(7) 0.0493(3) Uani 1 1 d . . . . .
H6 H 0.665977 0.736181 0.536138 0.059 Uiso 1 1 calc R U . . .
C7 C 0.71602(8) 1.05011(14) 0.77156(12) 0.0772(4) Uani 1 1 d . . . . .
H7 H 0.730514 1.123569 0.788538 0.093 Uiso 1 1 calc R U . . .
C8 C 0.65144(5) 0.85153(10) 0.68863(7) 0.0470(3) Uani 1 1 d . . . . .
C9 C 0.51891(18) 0.3304(3) 0.6151(3) 0.1065(11) Uani 0.7 1 d . U P A 1
H9A H 0.526050 0.311713 0.677804 0.160 Uiso 0.7 1 calc R U P A 1
H9B H 0.504842 0.262500 0.582334 0.160 Uiso 0.7 1 calc R U P A 1
H9C H 0.485367 0.388901 0.608254 0.160 Uiso 0.7 1 calc R U P A 1
C10 C 0.60513(5) 0.65091(10) 0.72259(7) 0.0489(3) Uani 1 1 d . . . . .
C11 C 0.58820(6) 0.68612(12) 0.81652(8) 0.0576(3) Uani 1 1 d . . . . .
H11A H 0.620355 0.652734 0.859629 0.069 Uiso 1 1 calc R U . . .
H11B H 0.545010 0.655350 0.829195 0.069 Uiso 1 1 calc R U . . .
C12 C 0.63144(6) 0.57517(11) 0.54975(8) 0.0520(3) Uani 1 1 d . . . . .
C13 C 0.74254(7) 1.00248(13) 0.70074(11) 0.0709(4) Uani 1 1 d . . . . .
H13 H 0.776023 1.041895 0.672865 0.085 Uiso 1 1 calc R U . . .
C14 C 0.64991(6) 0.86969(11) 0.79262(8) 0.0520(3) Uani 1 1 d . . . . .
H14 H 0.686546 0.822913 0.818403 0.062 Uiso 1 1 calc R U . . .
C15 C 0.58458(9) 0.37608(13) 0.57754(12) 0.0795(5) Uani 1 1 d . . . . .
H15 H 0.575343 0.382327 0.512301 0.095 Uiso 0.7 1 calc R U P A 1
H15A H 0.609173 0.363773 0.523086 0.095 Uiso 0.3 1 calc R U P A 2
C16 C 0.60159(6) 0.49835(11) 0.60793(9) 0.0576(3) Uani 1 1 d . . . . .
C17 C 0.69423(10) 0.98841(19) 0.92381(12) 0.0937(6) Uani 1 1 d . . . . .
H17A H 0.663260 0.951928 0.961721 0.141 Uiso 1 1 calc R U . . .
H17B H 0.703614 1.065093 0.945540 0.141 Uiso 1 1 calc R U . . .
H17C H 0.734457 0.944265 0.924806 0.141 Uiso 1 1 calc R U . . .
C18 C 0.58930(6) 0.53965(11) 0.69308(9) 0.0574(3) Uani 1 1 d . . . . .
H18 H 0.569297 0.490124 0.732894 0.069 Uiso 1 1 calc R U . . .
C19 C 0.6384(2) 0.2955(3) 0.5873(4) 0.1232(13) Uani 0.7 1 d . U P A 1
H19A H 0.674374 0.321457 0.552609 0.185 Uiso 0.7 1 calc R U P A 1
H19B H 0.623850 0.220884 0.566007 0.185 Uiso 0.7 1 calc R U P A 1
H19C H 0.652880 0.290119 0.649662 0.185 Uiso 0.7 1 calc R U P A 1
C20 C 0.58747(6) 0.81607(12) 0.82862(8) 0.0564(3) Uani 1 1 d . . . . .
H20A H 0.584912 0.834510 0.892095 0.068 Uiso 1 1 calc R U . . .
H20B H 0.548721 0.848205 0.796656 0.068 Uiso 1 1 calc R U . . .
C21 C 0.6196(6) 0.2899(6) 0.6543(6) 0.123(3) Uani 0.3 1 d . U P A 2
H21A H 0.665312 0.311012 0.664528 0.184 Uiso 0.3 1 calc R U P A 2
H21B H 0.616837 0.211411 0.633470 0.184 Uiso 0.3 1 calc R U P A 2
H21C H 0.597227 0.297019 0.709534 0.184 Uiso 0.3 1 calc R U P A 2
C22 C 0.60200(6) 0.92935(12) 0.63365(9) 0.0596(3) Uani 1 1 d . . . . .
H22A H 0.602348 0.909030 0.570983 0.089 Uiso 1 1 calc R U . . .
H22B H 0.614705 1.008816 0.641217 0.089 Uiso 1 1 calc R U . . .
H22C H 0.558278 0.918442 0.654670 0.089 Uiso 1 1 calc R U . . .


_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 C4 1.2219(14) . ?
O2 H2 0.8200 . ?
O2 C12 1.3725(14) . ?
C1 C6 1.3989(15) . ?
C1 C8 1.5280(16) . ?
C1 C10 1.3989(15) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 C3 1.538(2) . ?
C3 C7 1.501(2) . ?
C3 C14 1.5554(18) . ?
C3 C17 1.539(2) . ?
C4 C8 1.5363(15) . ?
C4 C13 1.4656(18) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C5 C15 1.331(7) . ?
C6 H6 0.9300 . ?
C6 C12 1.3796(16) . ?
C7 H7 0.9300 . ?
C7 C13 1.324(2) . ?
C8 C14 1.5598(16) . ?
C8 C22 1.5481(17) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C15 1.557(3) . ?
C10 C11 1.5081(16) . ?
C10 C18 1.3923(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C20 1.5147(18) . ?
C12 C16 1.3971(17) . ?
C13 H13 0.9300 . ?
C14 H14 0.9800 . ?
C14 C20 1.5266(16) . ?
C15 H15 0.9800 . ?
C15 H15A 0.9800 . ?
C15 C16 1.5195(19) . ?
C15 C19 1.435(4) . ?
C15 C21 1.648(8) . ?
C16 C18 1.3852(18) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
C12 O2 H2 109.5 . . ?
C6 C1 C8 119.64(10) . . ?
C6 C1 C10 118.04(10) . . ?
C10 C1 C8 122.15(10) . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
C2 C3 C14 114.63(12) . . ?
C2 C3 C17 107.35(13) . . ?
C7 C3 C2 109.51(14) . . ?
C7 C3 C14 110.20(10) . . ?
C7 C3 C17 106.19(13) . . ?
C17 C3 C14 108.58(14) . . ?
O1 C4 C8 124.13(10) . . ?
O1 C4 C13 120.40(10) . . ?
C13 C4 C8 115.47(10) . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C15 C5 H5A 109.5 . . ?
C15 C5 H5B 109.5 . . ?
C15 C5 H5C 109.5 . . ?
C1 C6 H6 119.0 . . ?
C12 C6 C1 121.93(10) . . ?
C12 C6 H6 119.0 . . ?
C3 C7 H7 117.5 . . ?
C13 C7 C3 125.05(13) . . ?
C13 C7 H7 117.5 . . ?
C1 C8 C4 113.72(9) . . ?
C1 C8 C14 110.77(9) . . ?
C1 C8 C22 107.56(9) . . ?
C4 C8 C14 104.69(9) . . ?
C4 C8 C22 106.57(9) . . ?
C22 C8 C14 113.57(10) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C9 H9A 109.5 . . ?
C15 C9 H9B 109.5 . . ?
C15 C9 H9C 109.5 . . ?
C1 C10 C11 122.52(11) . . ?
C18 C10 C1 118.68(10) . . ?
C18 C10 C11 118.80(10) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C10 C11 C20 112.45(10) . . ?
H11A C11 H11B 107.8 . . ?
C20 C11 H11A 109.1 . . ?
C20 C11 H11B 109.1 . . ?
O2 C12 C6 121.35(10) . . ?
O2 C12 C16 117.75(11) . . ?
C6 C12 C16 120.89(11) . . ?
C4 C13 H13 118.8 . . ?
C7 C13 C4 122.47(13) . . ?
C7 C13 H13 118.8 . . ?
C3 C14 C8 115.70(11) . . ?
C3 C14 H14 105.1 . . ?
C8 C14 H14 105.1 . . ?
C20 C14 C3 114.20(10) . . ?
C20 C14 C8 110.39(9) . . ?
C20 C14 H14 105.1 . . ?
C5 C15 H15A 105.3 . . ?
C5 C15 C16 114.8(4) . . ?
C5 C15 C21 119.0(6) . . ?
C9 C15 H15 104.7 . . ?
C16 C15 C9 113.22(16) . . ?
C16 C15 H15 104.7 . . ?
C16 C15 H15A 105.3 . . ?
C16 C15 C21 106.0(3) . . ?
C19 C15 C9 113.5(2) . . ?
C19 C15 H15 104.7 . . ?
C19 C15 C16 114.6(2) . . ?
C21 C15 H15A 105.3 . . ?
C12 C16 C15 120.49(11) . . ?
C18 C16 C12 116.54(11) . . ?
C18 C16 C15 122.97(11) . . ?
C3 C17 H17A 109.5 . . ?
C3 C17 H17B 109.5 . . ?
C3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18 118.1 . . ?
C16 C18 C10 123.89(11) . . ?
C16 C18 H18 118.1 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C20 C14 110.42(10) . . ?
C11 C20 H20A 109.6 . . ?
C11 C20 H20B 109.6 . . ?
C14 C20 H20A 109.6 . . ?
C14 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 C22 H22A 109.5 . . ?
C8 C22 H22B 109.5 . . ?
C8 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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 C4 C8 C1 10.90(17) . . . . ?
O1 C4 C8 C14 131.94(12) . . . . ?
O1 C4 C8 C22 -107.43(14) . . . . ?
O1 C4 C13 C7 -159.14(16) . . . . ?
O2 C12 C16 C15 0.5(2) . . . . ?
O2 C12 C16 C18 180.00(12) . . . . ?
C1 C6 C12 O2 -178.77(11) . . . . ?
C1 C6 C12 C16 1.60(19) . . . . ?
C1 C8 C14 C3 -179.17(9) . . . . ?
C1 C8 C14 C20 -47.54(13) . . . . ?
C1 C10 C11 C20 17.87(17) . . . . ?
C1 C10 C18 C16 -0.36(19) . . . . ?
C2 C3 C7 C13 -123.0(2) . . . . ?
C2 C3 C14 C8 87.47(15) . . . . ?
C2 C3 C14 C20 -42.35(18) . . . . ?
C3 C7 C13 C4 3.4(3) . . . . ?
C3 C14 C20 C11 -162.76(11) . . . . ?
C4 C8 C14 C3 57.86(13) . . . . ?
C4 C8 C14 C20 -170.52(10) . . . . ?
C5 C15 C16 C12 -100.4(5) . . . . ?
C5 C15 C16 C18 80.1(5) . . . . ?
C6 C1 C8 C4 -49.77(14) . . . . ?
C6 C1 C8 C14 -167.34(10) . . . . ?
C6 C1 C8 C22 68.00(13) . . . . ?
C6 C1 C10 C11 -177.86(11) . . . . ?
C6 C1 C10 C18 1.52(17) . . . . ?
C6 C12 C16 C15 -179.91(14) . . . . ?
C6 C12 C16 C18 -0.36(19) . . . . ?
C7 C3 C14 C8 -36.60(16) . . . . ?
C7 C3 C14 C20 -166.41(12) . . . . ?
C8 C1 C6 C12 -177.58(11) . . . . ?
C8 C1 C10 C11 -2.57(17) . . . . ?
C8 C1 C10 C18 176.81(10) . . . . ?
C8 C4 C13 C7 21.9(2) . . . . ?
C8 C14 C20 C11 64.84(13) . . . . ?
C9 C15 C16 C12 -143.8(2) . . . . ?
C9 C15 C16 C18 36.7(3) . . . . ?
C10 C1 C6 C12 -2.17(17) . . . . ?
C10 C1 C8 C4 135.02(11) . . . . ?
C10 C1 C8 C14 17.45(14) . . . . ?
C10 C1 C8 C22 -107.21(12) . . . . ?
C10 C11 C20 C14 -48.30(14) . . . . ?
C11 C10 C18 C16 179.04(12) . . . . ?
C12 C16 C18 C10 -0.2(2) . . . . ?
C13 C4 C8 C1 -170.19(11) . . . . ?
C13 C4 C8 C14 -49.15(14) . . . . ?
C13 C4 C8 C22 71.48(14) . . . . ?
C14 C3 C7 C13 4.0(2) . . . . ?
C15 C16 C18 C10 179.29(14) . . . . ?
C17 C3 C7 C13 121.4(2) . . . . ?
C17 C3 C14 C8 -152.52(12) . . . . ?
C17 C3 C14 C20 77.66(14) . . . . ?
C18 C10 C11 C20 -161.51(11) . . . . ?
C19 C15 C16 C12 83.9(3) . . . . ?
C19 C15 C16 C18 -95.6(3) . . . . ?
C21 C15 C16 C12 126.1(5) . . . . ?
C21 C15 C16 C18 -53.4(5) . . . . ?
C22 C8 C14 C3 -58.00(13) . . . . ?
C22 C8 C14 C20 73.63(13) . . . . ?

_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 3.404
_oxdiff_exptl_absorpt_empirical_full_min 0.483
####################################################################### 
# 
# 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_huochy_1116_autored
_audit_block_doi                 10.5517/ccdc.csd.cc2bw5fv
_database_code_depnum_ccdc_archive 'CCDC 2171067'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2SC04229K 2022
loop_
_audit_author_name
_audit_author_address
'chenyu huo'
;Lanzhou University
China
;
_audit_update_record             
;
2022-06-29 deposited with the CCDC.	2022-11-16 downloaded from the CCDC.
;
_audit_creation_date             2022-06-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H30 O3'
_chemical_formula_sum            'C20 H30 O3'
_chemical_formula_weight         318.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.7444(7)
_cell_length_b                   6.0960(2)
_cell_length_c                   22.9960(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.293(2)
_cell_angle_gamma                90
_cell_volume                     3453.97(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4658
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.3670
_cell_measurement_theta_min      3.6020
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10868
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.588
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     98.00 174.00   0.50    0.05    --  107.75  57.00-180.00  152
  2  ω    133.00 168.00   0.50    0.05    --  107.75  37.00-150.00   70
  3  ω     99.00 124.00   0.50    0.05    --  107.75  37.00-150.00   50
  4  ω     95.00 168.00   0.50    0.05    --  107.75  35.00  88.00  146
  5  ω     36.00 116.00   0.50    0.05    --   47.57  35.00  88.00  160
  6  ω    -33.00  -8.00   0.50    0.05    --  -47.57  35.00  88.00   50
  7  ω    -57.00 -27.00   0.50    0.05    -- -100.00  77.00 120.00   60
  8  ω    -69.00 -33.00   0.50    0.05    -- -100.00  57.00  60.00   72
  9  ω    -69.00 -27.00   0.50    0.05    -- -100.00  77.00   0.00   84
 10  ω    -99.00 -73.00   0.50    0.05    -- -100.00  77.00   0.00   52
 11  ω    -69.00 -44.00   0.50    0.05    -- -100.00  57.00 -30.00   50
 12  ω    -66.00 -27.00   0.50    0.05    -- -100.00  57.00 -90.00   78
 13  ω    -69.00 -44.00   0.50    0.05    -- -100.00  57.00-150.00   50
 14  ω     61.00  96.00   0.50    0.05    --  107.75 -99.00 150.00   70
 15  ω   -123.00 -87.00   0.50    0.05    -- -100.00 -35.00 -68.00   72
 16  ω   -168.00-119.00   0.50    0.05    -- -100.00 -57.00   0.00   98
 17  ω   -110.00 -85.00   0.50    0.05    -- -100.00 -57.00   0.00   50
 18  ω   -106.00 -41.00   0.50    0.05    --  -47.57 -35.00 -68.00  130
 19  ω     -7.00  35.00   0.50    0.05    --   47.57 -37.00 120.00   84
 20  ω    -26.00  16.00   0.50    0.05    --   47.57 -19.00 150.00   84
 21  ω     41.00  95.00   0.50    0.05    --  107.75 -77.00 150.00  108
 22  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00   0.00   50
 23  ω     35.00  63.00   0.50    0.05    --  107.75 -57.00 -60.00   56
 24  ω     36.00  62.00   0.50    0.05    --  107.75 -57.00-150.00   52
 25  ω     37.00  63.00   0.50    0.05    --  107.75 -57.00-180.00   52
 26  ω    -26.00   7.00   0.50    0.05    --   47.57 -35.00 -68.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0498968000
_diffrn_orient_matrix_UB_12      0.1123756000
_diffrn_orient_matrix_UB_13      0.0322482000
_diffrn_orient_matrix_UB_21      -0.0304466000
_diffrn_orient_matrix_UB_22      0.0194222000
_diffrn_orient_matrix_UB_23      0.0552654000
_diffrn_orient_matrix_UB_31      0.0222236000
_diffrn_orient_matrix_UB_32      -0.2255127000
_diffrn_orient_matrix_UB_33      0.0207697000
_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                2311
_reflns_number_total             3023
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.975
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0943
_refine_ls_restrained_S_all      1.231
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2859
_refine_ls_wR_factor_ref         0.3056
_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. Restrained distances
 H1_$1-H2_$2
 2.2 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.26076(12) 0.8623(5) 0.35030(10) 0.0728(8) Uani 1 1 d . . . . .
H1 H 0.260246 0.905037 0.315521 0.109 Uiso 1 1 calc R U . . .
O2 O 0.27768(13) 0.6318(5) 0.25037(11) 0.0825(9) Uani 1 1 d . . . . .
H2 H 0.244679 0.660727 0.252101 0.124 Uiso 1 1 calc R U . . .
O3 O 0.31258(10) 0.3238(5) 0.62908(9) 0.0647(7) Uani 1 1 d . . . . .
H3 H 0.301224 0.451698 0.633995 0.097 Uiso 1 1 calc R U . . .
C1 C 0.34594(12) 0.5837(5) 0.43173(11) 0.0422(7) Uani 1 1 d . . . . .
C2 C 0.28492(13) 0.5521(7) 0.41304(14) 0.0591(9) Uani 1 1 d . . . . .
H2A H 0.276424 0.393710 0.415059 0.071 Uiso 1 1 calc R U . . .
H2B H 0.263973 0.628236 0.441657 0.071 Uiso 1 1 calc R U . . .
C3 C 0.26550(16) 0.6347(7) 0.35224(16) 0.0675(10) Uani 1 1 d . . . . .
H3A H 0.228218 0.573856 0.342545 0.081 Uiso 1 1 calc R U . . .
C4 C 0.30045(15) 0.5488(6) 0.30609(13) 0.0606(9) Uani 1 1 d . . . . .
H4 H 0.295351 0.386123 0.304797 0.073 Uiso 1 1 calc R U . . .
C5 C 0.36071(14) 0.5883(5) 0.31883(12) 0.0493(8) Uani 1 1 d . . . . .
C6 C 0.37732(12) 0.4952(5) 0.38100(11) 0.0425(7) Uani 1 1 d . . . . .
H6 H 0.367684 0.335979 0.378166 0.051 Uiso 1 1 calc R U . . .
C7 C 0.43851(13) 0.4982(5) 0.39954(13) 0.0505(8) Uani 1 1 d . . . . .
H7A H 0.458900 0.465448 0.365493 0.061 Uiso 1 1 calc R U . . .
H7B H 0.449503 0.645357 0.414497 0.061 Uiso 1 1 calc R U . . .
C8 C 0.45136(13) 0.3280(5) 0.44667(13) 0.0486(7) Uani 1 1 d . . . . .
H8A H 0.450743 0.180668 0.428507 0.058 Uiso 1 1 calc R U . . .
H8B H 0.488483 0.353995 0.465314 0.058 Uiso 1 1 calc R U . . .
C9 C 0.41202(12) 0.3317(4) 0.49297(11) 0.0403(7) Uani 1 1 d . . . . .
C10 C 0.36269(11) 0.4440(5) 0.48615(11) 0.0409(7) Uani 1 1 d . . . . .
C11 C 0.32996(12) 0.4369(5) 0.53223(12) 0.0480(8) Uani 1 1 d . . . . .
H11 H 0.296408 0.513652 0.528512 0.058 Uiso 1 1 calc R U . . .
C12 C 0.34447(12) 0.3221(5) 0.58329(12) 0.0489(8) Uani 1 1 d . . . . .
C13 C 0.39212(12) 0.2011(5) 0.58997(12) 0.0453(7) Uani 1 1 d . . . . .
C14 C 0.42516(12) 0.2113(5) 0.54418(11) 0.0432(7) Uani 1 1 d . . . . .
H14 H 0.458393 0.132238 0.547886 0.052 Uiso 1 1 calc R U . . .
C15 C 0.40642(13) 0.0585(6) 0.64276(12) 0.0512(8) Uani 1 1 d . . . . .
H15 H 0.379235 0.090231 0.671244 0.061 Uiso 1 1 calc R U . . .
C16 C 0.4005(3) -0.1827(6) 0.62641(17) 0.0853(14) Uani 1 1 d . . . . .
H16A H 0.363834 -0.209449 0.607744 0.128 Uiso 1 1 calc R U . . .
H16B H 0.406488 -0.272892 0.661693 0.128 Uiso 1 1 calc R U . . .
H16C H 0.427234 -0.221242 0.599242 0.128 Uiso 1 1 calc R U . . .
C17 C 0.46139(19) 0.1122(9) 0.67266(17) 0.0842(14) Uani 1 1 d . . . . .
H17A H 0.488967 0.093134 0.645098 0.126 Uiso 1 1 calc R U . . .
H17B H 0.469345 0.013863 0.706075 0.126 Uiso 1 1 calc R U . . .
H17C H 0.461725 0.264503 0.686296 0.126 Uiso 1 1 calc R U . . .
C18 C 0.39062(19) 0.4534(6) 0.27426(14) 0.0698(11) Uani 1 1 d . . . . .
H18A H 0.429343 0.490055 0.278573 0.105 Uiso 1 1 calc R U . . .
H18B H 0.375367 0.488697 0.234508 0.105 Uiso 1 1 calc R U . . .
H18C H 0.386003 0.296475 0.281571 0.105 Uiso 1 1 calc R U . . .
C19 C 0.37819(15) 0.8278(5) 0.31070(13) 0.0543(8) Uani 1 1 d . . . . .
H19A H 0.356678 0.924622 0.333581 0.081 Uiso 1 1 calc R U . . .
H19B H 0.372273 0.867397 0.269298 0.081 Uiso 1 1 calc R U . . .
H19C H 0.416760 0.843854 0.324034 0.081 Uiso 1 1 calc R U . . .
C20 C 0.35755(17) 0.8227(5) 0.44941(13) 0.0574(9) Uani 1 1 d . . . . .
H20A H 0.340405 0.855862 0.485147 0.086 Uiso 1 1 calc R U . . .
H20B H 0.342830 0.920269 0.417973 0.086 Uiso 1 1 calc R U . . .
H20C H 0.396838 0.844853 0.456420 0.086 Uiso 1 1 calc R U . . .


_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 H1 0.8400 . ?
O1 C3 1.393(5) . ?
O2 H2 0.8400 . ?
O2 C4 1.443(4) . ?
O3 H3 0.8400 . ?
O3 C12 1.373(4) . ?
C1 C2 1.543(4) . ?
C1 C6 1.556(4) . ?
C1 C10 1.539(4) . ?
C1 C20 1.533(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.522(5) . ?
C3 H3A 1.0000 . ?
C3 C4 1.522(5) . ?
C4 H4 1.0000 . ?
C4 C5 1.512(5) . ?
C5 C6 1.558(4) . ?
C5 C18 1.554(5) . ?
C5 C19 1.539(5) . ?
C6 H6 1.0000 . ?
C6 C7 1.535(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.513(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.508(4) . ?
C9 C10 1.396(4) . ?
C9 C14 1.400(4) . ?
C10 C11 1.392(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(4) . ?
C12 C13 1.387(5) . ?
C13 C14 1.393(4) . ?
C13 C15 1.509(4) . ?
C14 H14 0.9500 . ?
C15 H15 1.0000 . ?
C15 C16 1.522(5) . ?
C15 C17 1.503(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C3 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C12 O3 H3 109.5 . . ?
C2 C1 C6 106.9(2) . . ?
C10 C1 C2 109.9(2) . . ?
C10 C1 C6 107.6(2) . . ?
C20 C1 C2 110.3(3) . . ?
C20 C1 C6 115.7(3) . . ?
C20 C1 C10 106.3(2) . . ?
C1 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 C1 115.6(3) . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
O1 C3 C2 112.2(3) . . ?
O1 C3 H3A 106.8 . . ?
O1 C3 C4 111.8(3) . . ?
C2 C3 H3A 106.8 . . ?
C2 C3 C4 112.0(3) . . ?
C4 C3 H3A 106.8 . . ?
O2 C4 C3 107.3(3) . . ?
O2 C4 H4 106.5 . . ?
O2 C4 C5 114.4(3) . . ?
C3 C4 H4 106.5 . . ?
C5 C4 C3 115.1(3) . . ?
C5 C4 H4 106.5 . . ?
C4 C5 C6 107.0(3) . . ?
C4 C5 C18 108.0(3) . . ?
C4 C5 C19 114.3(3) . . ?
C18 C5 C6 108.1(2) . . ?
C19 C5 C6 113.8(2) . . ?
C19 C5 C18 105.4(3) . . ?
C1 C6 C5 117.0(2) . . ?
C1 C6 H6 104.6 . . ?
C5 C6 H6 104.6 . . ?
C7 C6 C1 109.6(2) . . ?
C7 C6 C5 114.9(2) . . ?
C7 C6 H6 104.6 . . ?
C6 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 C6 109.1(2) . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.9(2) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C10 C9 C8 122.9(2) . . ?
C10 C9 C14 119.0(3) . . ?
C14 C9 C8 118.1(3) . . ?
C9 C10 C1 122.0(2) . . ?
C11 C10 C1 120.3(2) . . ?
C11 C10 C9 117.6(2) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 C10 122.5(3) . . ?
C12 C11 H11 118.8 . . ?
O3 C12 C11 121.6(3) . . ?
O3 C12 C13 117.5(2) . . ?
C11 C12 C13 120.9(3) . . ?
C12 C13 C14 116.4(2) . . ?
C12 C13 C15 122.0(3) . . ?
C14 C13 C15 121.6(3) . . ?
C9 C14 H14 118.2 . . ?
C13 C14 C9 123.5(3) . . ?
C13 C14 H14 118.2 . . ?
C13 C15 H15 107.1 . . ?
C13 C15 C16 110.4(3) . . ?
C16 C15 H15 107.1 . . ?
C17 C15 C13 112.2(3) . . ?
C17 C15 H15 107.1 . . ?
C17 C15 C16 112.7(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C5 C19 H19A 109.5 . . ?
C5 C19 H19B 109.5 . . ?
C5 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 C20 H20A 109.5 . . ?
C1 C20 H20B 109.5 . . ?
C1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 C3 C4 O2 -54.6(4) . . . . ?
O1 C3 C4 C5 74.0(4) . . . . ?
O2 C4 C5 C6 178.2(3) . . . . ?
O2 C4 C5 C18 -65.6(4) . . . . ?
O2 C4 C5 C19 51.3(4) . . . . ?
O3 C12 C13 C14 -176.7(3) . . . . ?
O3 C12 C13 C15 5.8(4) . . . . ?
C1 C2 C3 O1 -76.0(4) . . . . ?
C1 C2 C3 C4 50.7(5) . . . . ?
C1 C6 C7 C8 68.7(3) . . . . ?
C1 C10 C11 C12 -176.9(3) . . . . ?
C2 C1 C6 C5 53.2(3) . . . . ?
C2 C1 C6 C7 -173.8(2) . . . . ?
C2 C1 C10 C9 140.2(3) . . . . ?
C2 C1 C10 C11 -43.7(4) . . . . ?
C2 C3 C4 O2 178.5(3) . . . . ?
C2 C3 C4 C5 -52.9(4) . . . . ?
C3 C4 C5 C6 53.2(4) . . . . ?
C3 C4 C5 C18 169.3(3) . . . . ?
C3 C4 C5 C19 -73.8(4) . . . . ?
C4 C5 C6 C1 -55.5(3) . . . . ?
C4 C5 C6 C7 173.9(3) . . . . ?
C5 C6 C7 C8 -157.2(2) . . . . ?
C6 C1 C2 C3 -49.3(4) . . . . ?
C6 C1 C10 C9 24.1(4) . . . . ?
C6 C1 C10 C11 -159.8(3) . . . . ?
C6 C7 C8 C9 -45.0(3) . . . . ?
C7 C8 C9 C10 13.6(4) . . . . ?
C7 C8 C9 C14 -168.4(3) . . . . ?
C8 C9 C10 C1 -3.3(4) . . . . ?
C8 C9 C10 C11 -179.4(3) . . . . ?
C8 C9 C14 C13 -179.8(3) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C1 C2 C3 -165.8(3) . . . . ?
C10 C1 C6 C5 171.2(2) . . . . ?
C10 C1 C6 C7 -55.7(3) . . . . ?
C10 C9 C14 C13 -1.7(4) . . . . ?
C10 C11 C12 O3 177.5(3) . . . . ?
C10 C11 C12 C13 -2.3(5) . . . . ?
C11 C12 C13 C14 3.1(4) . . . . ?
C11 C12 C13 C15 -174.4(3) . . . . ?
C12 C13 C14 C9 -1.2(4) . . . . ?
C12 C13 C15 C16 107.6(4) . . . . ?
C12 C13 C15 C17 -125.8(4) . . . . ?
C14 C9 C10 C1 178.7(2) . . . . ?
C14 C9 C10 C11 2.5(4) . . . . ?
C14 C13 C15 C16 -69.8(4) . . . . ?
C14 C13 C15 C17 56.9(4) . . . . ?
C15 C13 C14 C9 176.3(3) . . . . ?
C18 C5 C6 C1 -171.5(3) . . . . ?
C18 C5 C6 C7 57.8(4) . . . . ?
C19 C5 C6 C1 71.7(4) . . . . ?
C19 C5 C6 C7 -58.9(3) . . . . ?
C20 C1 C2 C3 77.3(4) . . . . ?
C20 C1 C6 C5 -70.1(3) . . . . ?
C20 C1 C6 C7 62.9(3) . . . . ?
C20 C1 C10 C9 -100.4(3) . . . . ?
C20 C1 C10 C11 75.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.760
_oxdiff_exptl_absorpt_empirical_full_min 0.495
####################################################################### 
# 
# 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_huochenyu-wsh_1223_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2bw5cs
_database_code_depnum_ccdc_archive 'CCDC 2171065'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2SC04229K 2022
loop_
_audit_author_name
_audit_author_address
'chenyu huo'
;Lan Zhou University
China
;
_audit_update_record             
;
2022-05-06 deposited with the CCDC.	2022-11-16 downloaded from the CCDC.
;
_audit_creation_date             2021-12-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24'
_chemical_formula_sum            'C22 H24'
_chemical_formula_weight         288.41
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'

_cell_length_a                   17.4778(4)
_cell_length_b                   17.4778(4)
_cell_length_c                   9.9640(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2635.95(13)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.4540
_cell_measurement_theta_min      2.8870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.454
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14286
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.110
_diffrn_reflns_theta_min         2.919
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     45.00  85.00   0.50    0.45    --  107.75-125.00 -30.00   80
  2  ω     35.00  63.00   0.50    0.45    --  107.75 -57.00   0.00   56
  3  ω     36.00  61.00   0.50    0.45    --  107.75 -57.00 -30.00   50
  4  ω     59.00 122.00   0.50    0.45    --  107.75 150.00  96.00  126
  5  ω    128.00 166.00   0.50    0.45    --  107.75 150.00  96.00   76
  6  ω    -21.00  17.00   0.50    0.15    --   47.57 -19.00-180.00   76
  7  ω    -23.00  23.00   0.50    0.15    --   47.57 -19.00-150.00   92
  8  ω   -170.00 -80.00   0.50    0.45    -- -100.00-128.00-102.00  180
  9  ω    -99.00 -71.00   0.50    0.15    --  -47.57-146.00  70.00   56
 10  ω    -84.00 -58.00   0.50    0.15    --  -47.57 124.00 -45.00   52
 11  ω    -65.00 -27.00   0.50    0.45    -- -100.00 122.00 -65.00   76
 12  ω   -104.00 -72.00   0.50    0.45    -- -100.00 122.00 -65.00   64
 13  ω   -109.00 -82.00   0.50    0.45    -- -100.00 121.00 -84.00   54
 14  ω    -76.00 -28.00   0.50    0.45    -- -100.00 121.00 -84.00   96
 15  ω    -26.00  -1.00   0.50    0.15    --  -47.57   8.00 140.00   50
 16  ω     68.00  93.00   0.50    0.15    --   47.57 142.00 143.00   50
 17  ω     51.00  76.00   0.50    0.15    --   47.57   8.00 140.00   50
 18  ω   -128.00-103.00   0.50    0.45    -- -100.00  -8.00 -34.00   50
 19  ω    102.00 127.00   0.50    0.45    --  107.75 122.00 -65.00   50
 20  ω    132.00 158.00   0.50    0.45    --  107.75  57.00 -90.00   52
 21  ω   -104.00 -36.00   0.50    0.15    --  -47.57 -19.00-150.00  136
 22  ω    -61.00 -33.00   0.50    0.15    --  -47.57 -57.00-150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0419720000
_diffrn_orient_matrix_UB_12      0.1010538000
_diffrn_orient_matrix_UB_13      -0.0105775000
_diffrn_orient_matrix_UB_21      -0.0926061000
_diffrn_orient_matrix_UB_22      -0.0104167000
_diffrn_orient_matrix_UB_23      -0.0124400000
_diffrn_orient_matrix_UB_31      -0.0045823000
_diffrn_orient_matrix_UB_32      0.0061524000
_diffrn_orient_matrix_UB_33      0.1537465000
_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         0.567
_reflns_Friedel_fraction_full    0.670
_reflns_Friedel_fraction_max     0.614
_reflns_number_gt                2805
_reflns_number_total             2980
_reflns_odcompleteness_completeness 100.00
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 910 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2980
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.082
_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)+(0.0690P)²+0.2275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1125
_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
2.a Ternary CH refined with riding coordinates:
 C6(H6), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C11(H11), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18),
 C20(H20), C22(H22)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.37495(15) -0.36096(14) -0.4790(2) 0.0276(4) Uani 1 1 d . . . . .
C2 C -0.34144(14) -0.41830(14) -0.4960(2) 0.0249(4) Uani 1 1 d . . . . .
C3 C -0.65275(14) -0.67569(13) -0.4807(2) 0.0253(4) Uani 1 1 d . . . . .
C4 C -0.67711(14) -0.68005(14) -0.6146(2) 0.0288(4) Uani 1 1 d . . . . .
H4 H -0.633817 -0.664510 -0.682823 0.035 Uiso 1 1 calc R U . . .
C5 C -0.39808(13) -0.51817(13) -0.4718(2) 0.0239(4) Uani 1 1 d . . . . .
C6 C -0.49709(13) -0.54663(13) -0.4765(2) 0.0231(4) Uani 1 1 d . . . . .
H6 H -0.510250 -0.538022 -0.571131 0.028 Uiso 1 1 calc R U . . .
C7 C -0.45015(14) -0.66762(13) -0.5839(2) 0.0262(4) Uani 1 1 d . . . . .
C8 C -0.52663(14) -0.70064(14) -0.5189(2) 0.0287(5) Uani 1 1 d . . . . .
H8 H -0.564493 -0.762920 -0.519297 0.034 Uiso 1 1 calc R U . . .
C9 C -0.51781(14) -0.48771(14) -0.3895(2) 0.0281(4) Uani 1 1 d . . . . .
H9A H -0.582397 -0.511072 -0.388143 0.034 Uiso 1 1 calc R U . . .
H9B H -0.498132 -0.487549 -0.296236 0.034 Uiso 1 1 calc R U . . .
C10 C -0.55706(13) -0.64537(14) -0.4445(2) 0.0256(4) Uani 1 1 d . . . . .
H10 H -0.553736 -0.654221 -0.345952 0.031 Uiso 1 1 calc R U . . .
C11 C -0.25284(14) -0.38236(15) -0.5314(2) 0.0302(4) Uani 1 1 d . . . . .
H11 H -0.229799 -0.420817 -0.544857 0.036 Uiso 1 1 calc R U . . .
C12 C -0.38170(13) -0.57038(13) -0.5817(2) 0.0258(4) Uani 1 1 d . . . . .
H12A H -0.381128 -0.544368 -0.670176 0.031 Uiso 1 1 calc R U . . .
H12B H -0.322703 -0.563975 -0.567517 0.031 Uiso 1 1 calc R U . . .
C13 C -0.76398(16) -0.70685(15) -0.6503(3) 0.0348(5) Uani 1 1 d . . . . .
H13 H -0.779612 -0.709004 -0.742099 0.042 Uiso 1 1 calc R U . . .
C14 C -0.23090(16) -0.23548(15) -0.5279(3) 0.0363(5) Uani 1 1 d . . . . .
H14 H -0.193673 -0.173436 -0.537241 0.044 Uiso 1 1 calc R U . . .
C15 C -0.19717(15) -0.29184(16) -0.5477(3) 0.0337(5) Uani 1 1 d . . . . .
H15 H -0.137036 -0.268846 -0.572026 0.040 Uiso 1 1 calc R U . . .
C16 C -0.47116(15) -0.39409(15) -0.4444(3) 0.0317(5) Uani 1 1 d . . . . .
H16A H -0.474271 -0.354140 -0.376915 0.038 Uiso 1 1 calc R U . . .
H16B H -0.502442 -0.392037 -0.525922 0.038 Uiso 1 1 calc R U . . .
C17 C -0.31857(16) -0.27022(15) -0.4945(2) 0.0329(5) Uani 1 1 d . . . . .
H17 H -0.341262 -0.231410 -0.481788 0.039 Uiso 1 1 calc R U . . .
C18 C -0.71761(15) -0.69916(15) -0.3826(2) 0.0318(5) Uani 1 1 d . . . . .
H18 H -0.702150 -0.696202 -0.290576 0.038 Uiso 1 1 calc R U . . .
C19 C -0.37141(15) -0.53822(14) -0.3345(2) 0.0297(4) Uani 1 1 d . . . . .
H19A H -0.307791 -0.516818 -0.333893 0.045 Uiso 1 1 calc R U . . .
H19B H -0.403844 -0.602120 -0.318715 0.045 Uiso 1 1 calc R U . . .
H19C H -0.385629 -0.508465 -0.263614 0.045 Uiso 1 1 calc R U . . .
C20 C -0.82705(16) -0.73019(16) -0.5519(3) 0.0375(5) Uani 1 1 d . . . . .
H20 H -0.886408 -0.748735 -0.575946 0.045 Uiso 1 1 calc R U . . .
C21 C -0.42735(16) -0.72564(16) -0.6662(3) 0.0359(5) Uani 1 1 d . . . . .
H21A H -0.478004 -0.785872 -0.668109 0.054 Uiso 1 1 calc R U . . .
H21B H -0.376473 -0.726275 -0.626065 0.054 Uiso 1 1 calc R U . . .
H21C H -0.412713 -0.702574 -0.757913 0.054 Uiso 1 1 calc R U . . .
C22 C -0.80438(16) -0.72676(16) -0.4176(3) 0.0382(5) Uani 1 1 d . . . . .
H22 H -0.848147 -0.743257 -0.349889 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.401(3) . ?
C1 C16 1.519(3) . ?
C1 C17 1.395(3) . ?
C2 C5 1.535(3) . ?
C2 C11 1.395(3) . ?
C3 C4 1.392(3) . ?
C3 C10 1.524(3) . ?
C3 C18 1.394(3) . ?
C4 H4 0.9500 . ?
C4 C13 1.393(3) . ?
C5 C6 1.544(3) . ?
C5 C12 1.541(3) . ?
C5 C19 1.541(3) . ?
C6 H6 1.0000 . ?
C6 C9 1.522(3) . ?
C6 C10 1.539(3) . ?
C7 C8 1.330(3) . ?
C7 C12 1.512(3) . ?
C7 C21 1.504(3) . ?
C8 H8 0.9500 . ?
C8 C10 1.510(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C16 1.519(3) . ?
C10 H10 1.0000 . ?
C11 H11 0.9500 . ?
C11 C15 1.392(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 0.9500 . ?
C13 C20 1.376(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(4) . ?
C14 C17 1.377(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C18 C22 1.387(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C22 1.388(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 0.9500 . ?

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 C16 122.25(19) . . ?
C17 C1 C2 119.3(2) . . ?
C17 C1 C16 118.45(19) . . ?
C1 C2 C5 122.13(19) . . ?
C11 C2 C1 118.40(19) . . ?
C11 C2 C5 119.43(18) . . ?
C4 C3 C10 119.91(18) . . ?
C4 C3 C18 118.3(2) . . ?
C18 C3 C10 121.7(2) . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C13 121.0(2) . . ?
C13 C4 H4 119.5 . . ?
C2 C5 C6 110.07(15) . . ?
C2 C5 C12 110.89(17) . . ?
C2 C5 C19 107.55(17) . . ?
C12 C5 C6 107.33(16) . . ?
C19 C5 C6 111.81(17) . . ?
C19 C5 C12 109.22(16) . . ?
C5 C6 H6 106.6 . . ?
C9 C6 C5 111.86(17) . . ?
C9 C6 H6 106.6 . . ?
C9 C6 C10 112.44(17) . . ?
C10 C6 C5 112.34(16) . . ?
C10 C6 H6 106.6 . . ?
C8 C7 C12 122.63(18) . . ?
C8 C7 C21 121.4(2) . . ?
C21 C7 C12 116.00(19) . . ?
C7 C8 H8 117.9 . . ?
C7 C8 C10 124.11(19) . . ?
C10 C8 H8 117.9 . . ?
C6 C9 H9A 109.7 . . ?
C6 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C16 C9 C6 110.03(18) . . ?
C16 C9 H9A 109.7 . . ?
C16 C9 H9B 109.7 . . ?
C3 C10 C6 110.76(16) . . ?
C3 C10 H10 108.5 . . ?
C6 C10 H10 108.5 . . ?
C8 C10 C3 109.74(18) . . ?
C8 C10 C6 110.82(17) . . ?
C8 C10 H10 108.5 . . ?
C2 C11 H11 119.0 . . ?
C15 C11 C2 122.0(2) . . ?
C15 C11 H11 119.0 . . ?
C5 C12 H12A 108.9 . . ?
C5 C12 H12B 108.9 . . ?
C7 C12 C5 113.53(17) . . ?
C7 C12 H12A 108.9 . . ?
C7 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C4 C13 H13 120.2 . . ?
C20 C13 C4 119.7(2) . . ?
C20 C13 H13 120.2 . . ?
C15 C14 H14 120.2 . . ?
C17 C14 H14 120.2 . . ?
C17 C14 C15 119.6(2) . . ?
C11 C15 C14 119.0(2) . . ?
C11 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C1 C16 H16A 109.0 . . ?
C1 C16 H16B 109.0 . . ?
C9 C16 C1 112.83(17) . . ?
C9 C16 H16A 109.0 . . ?
C9 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C1 C17 H17 119.1 . . ?
C14 C17 C1 121.7(2) . . ?
C14 C17 H17 119.1 . . ?
C3 C18 H18 119.6 . . ?
C22 C18 C3 120.9(2) . . ?
C22 C18 H18 119.6 . . ?
C5 C19 H19A 109.5 . . ?
C5 C19 H19B 109.5 . . ?
C5 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C20 H20 119.8 . . ?
C13 C20 C22 120.3(2) . . ?
C22 C20 H20 119.8 . . ?
C7 C21 H21A 109.5 . . ?
C7 C21 H21B 109.5 . . ?
C7 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 C20 119.7(2) . . ?
C18 C22 H22 120.1 . . ?
C20 C22 H22 120.1 . . ?

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
C1 C2 C5 C6 19.4(3) . . . . ?
C1 C2 C5 C12 137.97(19) . . . . ?
C1 C2 C5 C19 -102.7(2) . . . . ?
C1 C2 C11 C15 1.2(3) . . . . ?
C2 C1 C16 C9 17.6(3) . . . . ?
C2 C1 C17 C14 0.8(3) . . . . ?
C2 C5 C6 C9 -49.0(2) . . . . ?
C2 C5 C6 C10 -176.60(17) . . . . ?
C2 C5 C12 C7 -165.98(16) . . . . ?
C2 C11 C15 C14 0.1(4) . . . . ?
C3 C4 C13 C20 -0.6(3) . . . . ?
C3 C18 C22 C20 -0.8(4) . . . . ?
C4 C3 C10 C6 68.6(2) . . . . ?
C4 C3 C10 C8 -54.1(3) . . . . ?
C4 C3 C18 C22 0.4(3) . . . . ?
C4 C13 C20 C22 0.3(4) . . . . ?
C5 C2 C11 C15 -176.6(2) . . . . ?
C5 C6 C9 C16 64.5(2) . . . . ?
C5 C6 C10 C3 -167.11(17) . . . . ?
C5 C6 C10 C8 -45.1(2) . . . . ?
C6 C5 C12 C7 -45.7(2) . . . . ?
C6 C9 C16 C1 -46.4(2) . . . . ?
C7 C8 C10 C3 133.5(2) . . . . ?
C7 C8 C10 C6 10.9(3) . . . . ?
C8 C7 C12 C5 14.2(3) . . . . ?
C9 C6 C10 C3 65.6(2) . . . . ?
C9 C6 C10 C8 -172.31(17) . . . . ?
C10 C3 C4 C13 -179.47(19) . . . . ?
C10 C3 C18 C22 -179.9(2) . . . . ?
C10 C6 C9 C16 -167.98(17) . . . . ?
C11 C2 C5 C6 -162.98(18) . . . . ?
C11 C2 C5 C12 -44.4(2) . . . . ?
C11 C2 C5 C19 75.0(2) . . . . ?
C12 C5 C6 C9 -169.82(17) . . . . ?
C12 C5 C6 C10 62.6(2) . . . . ?
C12 C7 C8 C10 4.7(3) . . . . ?
C13 C20 C22 C18 0.4(4) . . . . ?
C15 C14 C17 C1 0.5(4) . . . . ?
C16 C1 C2 C5 -4.1(3) . . . . ?
C16 C1 C2 C11 178.2(2) . . . . ?
C16 C1 C17 C14 -179.0(2) . . . . ?
C17 C1 C2 C5 176.07(19) . . . . ?
C17 C1 C2 C11 -1.6(3) . . . . ?
C17 C1 C16 C9 -162.5(2) . . . . ?
C17 C14 C15 C11 -0.9(4) . . . . ?
C18 C3 C4 C13 0.2(3) . . . . ?
C18 C3 C10 C6 -111.1(2) . . . . ?
C18 C3 C10 C8 126.2(2) . . . . ?
C19 C5 C6 C9 70.4(2) . . . . ?
C19 C5 C6 C10 -57.1(2) . . . . ?
C19 C5 C12 C7 75.7(2) . . . . ?
C21 C7 C8 C10 -174.6(2) . . . . ?
C21 C7 C12 C5 -166.56(19) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.296 255.8 62.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_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 3.805
_oxdiff_exptl_absorpt_empirical_full_min 0.166
