# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_3-561
_database_code_depnum_ccdc_archive 'CCDC 2018583'
loop_
_audit_author_name
_audit_author_address
'Peijun Liu'
;Zunyi Medical Univeristy
China
;
_audit_update_record             
;
2020-07-23 deposited with the CCDC.	2020-10-07 downloaded from the CCDC.
;
_audit_creation_date             2019-12-14
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 O'
_chemical_formula_sum            'C21 H24 O'
_chemical_formula_weight         292.40
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0580(13)
_cell_length_b                   10.9276(12)
_cell_length_c                   16.1095(18)
_cell_angle_alpha                88.164(9)
_cell_angle_beta                 78.300(10)
_cell_angle_gamma                88.386(10)
_cell_volume                     1732.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3752
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.4190
_cell_measurement_theta_min      2.6460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.121
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12269
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.068
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  59.00   1.00    4.00    --  -11.59  77.00   0.00  103
  2  ω     32.00  59.00   1.00    4.00    --  -11.59  77.00-120.00   27
  3  ω      0.00  79.00   1.00    4.00    --   11.74  77.00 -90.00   79
  4  ω    -20.00  80.00   1.00    4.00    --   11.74  77.00 150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0715269000
_diffrn_orient_matrix_UB_12      -0.0007331000
_diffrn_orient_matrix_UB_13      -0.0038396000
_diffrn_orient_matrix_UB_21      -0.0073526000
_diffrn_orient_matrix_UB_22      0.0380936000
_diffrn_orient_matrix_UB_23      0.0355506000
_diffrn_orient_matrix_UB_31      -0.0043509000
_diffrn_orient_matrix_UB_32      -0.0526112000
_diffrn_orient_matrix_UB_33      0.0272884000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4109
_reflns_number_total             6089
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.558
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         6089
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0859
_refine_ls_restrained_S_all      1.124
_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)+(0.1378P)²+1.0846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2449
_refine_ls_wR_factor_ref         0.2746
_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. Rigid bond restraints
 C18, C21
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C18, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C18 \\sim C20: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C18 \\sim C21: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Ternary CH refined with riding coordinates:
 C22(H22), C7(H7), C16(H16), C23(H23)
4.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C24(H24A,H24B)
4.c Aromatic/amide H refined with riding coordinates:
 C34(H34), C35(H35), C38(H38), C9(H9), C3(H3), C5(H5), C6(H6), C37(H37),
 C2(H2), C10(H10), C12(H12), C28(H28), C11(H11), C31(H31), C29(H29), C30(H30)
4.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C17(H17A,H17B,H17C), C42(H42A,H42B,H42C), C41(H41A,H41B,
 H41C), C40(H40A,H40B,H40C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), 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
C33 C 0.0683(3) 0.7586(3) 0.38281(18) 0.0428(7) Uani 1 1 d . . . . .
C8 C 0.5341(3) 0.4591(3) 0.86765(18) 0.0474(7) Uani 1 1 d . . . . .
C36 C 0.1095(3) 0.8867(3) 0.22452(18) 0.0458(7) Uani 1 1 d . . . . .
C22 C 0.0459(3) 0.6916(3) 0.46838(19) 0.0496(8) Uani 1 1 d . . . . .
H22 H -0.038360 0.646458 0.473976 0.060 Uiso 1 1 calc R U . . .
C34 C 0.1886(3) 0.8173(3) 0.35045(19) 0.0475(7) Uani 1 1 d . . . . .
H34 H 0.257264 0.814641 0.381403 0.057 Uiso 1 1 calc R U . . .
C4 C 0.3993(3) 0.2820(3) 0.83158(19) 0.0481(7) Uani 1 1 d . . . . .
C35 C 0.2090(3) 0.8800(3) 0.27283(19) 0.0473(7) Uani 1 1 d . . . . .
H35 H 0.291096 0.918366 0.252820 0.057 Uiso 1 1 calc R U . . .
C38 C -0.0313(3) 0.7657(3) 0.3347(2) 0.0511(8) Uani 1 1 d . . . . .
H38 H -0.113301 0.727105 0.354630 0.061 Uiso 1 1 calc R U . . .
C7 C 0.3981(3) 0.3955(3) 0.88406(19) 0.0505(8) Uani 1 1 d . . . . .
H7 H 0.379957 0.367822 0.943661 0.061 Uiso 1 1 calc R U . . .
C13 C 0.5415(4) 0.5834(3) 0.88353(19) 0.0539(8) Uani 1 1 d . . . . .
C1 C 0.4017(3) 0.0683(3) 0.7356(2) 0.0520(8) Uani 1 1 d . . . . .
O1 O 0.4263(4) 0.7620(3) 0.9380(2) 0.1137(12) Uani 1 1 d . . . . .
C27 C 0.1582(3) 0.5975(3) 0.4742(2) 0.0553(9) Uani 1 1 d . . . . .
C9 C 0.6565(4) 0.3953(3) 0.8387(2) 0.0576(9) Uani 1 1 d . . . . .
H9 H 0.654536 0.312111 0.828503 0.069 Uiso 1 1 calc R U . . .
C3 C 0.3829(4) 0.1681(3) 0.8695(2) 0.0593(9) Uani 1 1 d . . . . .
H3 H 0.370817 0.160856 0.928200 0.071 Uiso 1 1 calc R U . . .
C5 C 0.4181(4) 0.2875(3) 0.74422(19) 0.0556(8) Uani 1 1 d . . . . .
H5 H 0.430737 0.363182 0.716017 0.067 Uiso 1 1 calc R U . . .
C6 C 0.4186(3) 0.1834(3) 0.6976(2) 0.0581(9) Uani 1 1 d . . . . .
H6 H 0.430777 0.191081 0.638944 0.070 Uiso 1 1 calc R U . . .
C37 C -0.0114(3) 0.8284(3) 0.2579(2) 0.0549(8) Uani 1 1 d . . . . .
H37 H -0.080869 0.831997 0.227574 0.066 Uiso 1 1 calc R U . . .
C39 C 0.1305(4) 0.9551(3) 0.1385(2) 0.0579(9) Uani 1 1 d . . . . .
C16 C 0.2824(4) 0.4865(3) 0.8737(2) 0.0635(9) Uani 1 1 d . . . . .
H16 H 0.299373 0.516654 0.814598 0.076 Uiso 1 1 calc R U . . .
C2 C 0.3837(4) 0.0634(3) 0.8233(2) 0.0608(9) Uani 1 1 d . . . . .
H2 H 0.371797 -0.012180 0.851703 0.073 Uiso 1 1 calc R U . . .
C18 C 0.4062(4) -0.0458(4) 0.6819(3) 0.0862(11) Uani 1 1 d . U . . .
C14 C 0.4174(4) 0.6560(3) 0.9186(2) 0.0674(10) Uani 1 1 d . . . . .
C23 C 0.0245(4) 0.7810(3) 0.5414(2) 0.0656(10) Uani 1 1 d . . . . .
H23 H 0.105154 0.831706 0.533921 0.079 Uiso 1 1 calc R U . . .
C15 C 0.2843(4) 0.5952(4) 0.9302(2) 0.0702(10) Uani 1 1 d . . . . .
H15A H 0.216696 0.655307 0.919247 0.084 Uiso 1 1 calc R U . . .
H15B H 0.258044 0.567582 0.988908 0.084 Uiso 1 1 calc R U . . .
C10 C 0.7793(4) 0.4521(4) 0.8248(2) 0.0673(10) Uani 1 1 d . . . . .
H10 H 0.858831 0.406964 0.805736 0.081 Uiso 1 1 calc R U . . .
C12 C 0.6674(4) 0.6391(3) 0.8689(2) 0.0675(10) Uani 1 1 d . . . . .
H12 H 0.671127 0.721825 0.879842 0.081 Uiso 1 1 calc R U . . .
C28 C 0.2265(4) 0.5383(3) 0.4020(3) 0.0712(10) Uani 1 1 d . . . . .
H28 H 0.204461 0.558328 0.349841 0.085 Uiso 1 1 calc R U . . .
C26 C 0.1938(4) 0.5649(4) 0.5516(3) 0.0775(12) Uani 1 1 d . . . . .
C11 C 0.7859(4) 0.5754(4) 0.8388(2) 0.0711(10) Uani 1 1 d . . . . .
H11 H 0.868870 0.614485 0.828141 0.085 Uiso 1 1 calc R U . . .
C25 C 0.1208(7) 0.6215(5) 0.6316(3) 0.1033(18) Uani 1 1 d . . . . .
C24 C 0.0123(6) 0.7102(5) 0.6261(2) 0.0992(17) Uani 1 1 d . . . . .
H24A H 0.008270 0.768760 0.670611 0.119 Uiso 1 1 calc R U . . .
H24B H -0.073060 0.667568 0.637389 0.119 Uiso 1 1 calc R U . . .
C31 C 0.2953(7) 0.4756(6) 0.5539(5) 0.114(2) Uani 1 1 d . . . . .
H31 H 0.318568 0.454367 0.605541 0.137 Uiso 1 1 calc R U . . .
O2 O 0.1494(6) 0.5948(5) 0.6995(3) 0.178(2) Uani 1 1 d . . . . .
C32 C -0.0976(5) 0.8659(4) 0.5415(3) 0.0942(14) Uani 1 1 d . . . . .
H32A H -0.085847 0.911130 0.488504 0.141 Uiso 1 1 calc R U . . .
H32B H -0.105961 0.921835 0.587099 0.141 Uiso 1 1 calc R U . . .
H32C H -0.178241 0.818446 0.548834 0.141 Uiso 1 1 calc R U . . .
C29 C 0.3272(5) 0.4497(4) 0.4066(4) 0.1038(17) Uani 1 1 d . . . . .
H29 H 0.371621 0.411320 0.357634 0.125 Uiso 1 1 calc R U . . .
C17 C 0.1438(4) 0.4273(5) 0.8932(3) 0.0963(15) Uani 1 1 d . . . . .
H17A H 0.127568 0.392580 0.949741 0.145 Uiso 1 1 calc R U . . .
H17B H 0.141869 0.363946 0.853557 0.145 Uiso 1 1 calc R U . . .
H17C H 0.074735 0.488091 0.888583 0.145 Uiso 1 1 calc R U . . .
C42 C 0.0903(6) 0.8762(5) 0.0716(3) 0.1032(16) Uani 1 1 d . . . . .
H42A H 0.136983 0.798281 0.070733 0.155 Uiso 1 1 calc R U . . .
H42B H 0.114635 0.916426 0.016997 0.155 Uiso 1 1 calc R U . . .
H42C H -0.005932 0.864298 0.085087 0.155 Uiso 1 1 calc R U . . .
C30 C 0.3610(6) 0.4190(6) 0.4830(6) 0.125(2) Uani 1 1 d . . . . .
H30 H 0.428266 0.359899 0.486163 0.150 Uiso 1 1 calc R U . . .
C41 C 0.2801(6) 0.9855(6) 0.1045(3) 0.118(2) Uani 1 1 d . . . . .
H41A H 0.309390 1.041033 0.141773 0.178 Uiso 1 1 calc R U . . .
H41B H 0.289879 1.022807 0.048887 0.178 Uiso 1 1 calc R U . . .
H41C H 0.334524 0.911551 0.101567 0.178 Uiso 1 1 calc R U . . .
C40 C 0.0464(7) 1.0729(5) 0.1466(3) 0.126(2) Uani 1 1 d . . . . .
H40A H -0.048168 1.054155 0.162255 0.189 Uiso 1 1 calc R U . . .
H40B H 0.063211 1.117470 0.093290 0.189 Uiso 1 1 calc R U . . .
H40C H 0.071026 1.121829 0.189354 0.189 Uiso 1 1 calc R U . . .
C19 C 0.3006(6) -0.0378(6) 0.6281(4) 0.133(2) Uani 1 1 d . . . . .
H19A H 0.322412 0.026757 0.586100 0.199 Uiso 1 1 calc R U . . .
H19B H 0.213263 -0.020976 0.663197 0.199 Uiso 1 1 calc R U . . .
H19C H 0.298592 -0.114150 0.600531 0.199 Uiso 1 1 calc R U . . .
C20 C 0.5441(5) -0.0614(5) 0.6269(4) 0.1212(16) Uani 1 1 d . U . . .
H20A H 0.542919 -0.126306 0.588361 0.182 Uiso 1 1 calc R U . . .
H20B H 0.609030 -0.081234 0.661763 0.182 Uiso 1 1 calc R U . . .
H20C H 0.568801 0.013426 0.595401 0.182 Uiso 1 1 calc R U . . .
C21 C 0.3783(8) -0.1641(5) 0.7359(4) 0.1342(17) Uani 1 1 d . U . . .
H21A H 0.288797 -0.159312 0.770669 0.201 Uiso 1 1 calc R U . . .
H21B H 0.444014 -0.174382 0.771421 0.201 Uiso 1 1 calc R U . . .
H21C H 0.384687 -0.232700 0.699407 0.201 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
C33 C22 1.519(4) . ?
C33 C34 1.382(4) . ?
C33 C38 1.385(4) . ?
C8 C7 1.523(5) . ?
C8 C13 1.397(4) . ?
C8 C9 1.400(5) . ?
C36 C35 1.385(4) . ?
C36 C37 1.390(4) . ?
C36 C39 1.533(4) . ?
C22 H22 0.9800 . ?
C22 C27 1.521(5) . ?
C22 C23 1.532(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.387(4) . ?
C4 C7 1.522(4) . ?
C4 C3 1.367(5) . ?
C4 C5 1.381(4) . ?
C35 H35 0.9300 . ?
C38 H38 0.9300 . ?
C38 C37 1.375(4) . ?
C7 H7 0.9800 . ?
C7 C16 1.540(5) . ?
C13 C14 1.481(5) . ?
C13 C12 1.394(5) . ?
C1 C6 1.380(5) . ?
C1 C2 1.386(5) . ?
C1 C18 1.535(5) . ?
O1 C14 1.220(4) . ?
C27 C28 1.393(5) . ?
C27 C26 1.399(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.385(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C6 H6 0.9300 . ?
C37 H37 0.9300 . ?
C39 C42 1.523(5) . ?
C39 C41 1.535(6) . ?
C39 C40 1.514(6) . ?
C16 H16 0.9800 . ?
C16 C15 1.523(5) . ?
C16 C17 1.523(6) . ?
C2 H2 0.9300 . ?
C18 C19 1.500(7) . ?
C18 C20 1.495(7) . ?
C18 C21 1.535(8) . ?
C14 C15 1.486(6) . ?
C23 H23 0.9800 . ?
C23 C24 1.532(6) . ?
C23 C32 1.518(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C10 H10 0.9300 . ?
C10 C11 1.379(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.372(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.392(6) . ?
C26 C25 1.492(8) . ?
C26 C31 1.397(8) . ?
C11 H11 0.9300 . ?
C25 C24 1.453(8) . ?
C25 O2 1.210(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C31 H31 0.9300 . ?
C31 C30 1.356(9) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C29 H29 0.9300 . ?
C29 C30 1.372(9) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C30 H30 0.9300 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C34 C33 C22 121.2(3) . . ?
C34 C33 C38 117.2(3) . . ?
C38 C33 C22 121.6(3) . . ?
C13 C8 C7 120.9(3) . . ?
C13 C8 C9 117.4(3) . . ?
C9 C8 C7 121.7(3) . . ?
C35 C36 C37 116.7(3) . . ?
C35 C36 C39 122.1(3) . . ?
C37 C36 C39 121.2(3) . . ?
C33 C22 H22 106.9 . . ?
C33 C22 C27 112.3(3) . . ?
C33 C22 C23 111.6(3) . . ?
C27 C22 H22 106.9 . . ?
C27 C22 C23 112.0(3) . . ?
C23 C22 H22 106.9 . . ?
C33 C34 H34 119.3 . . ?
C33 C34 C35 121.5(3) . . ?
C35 C34 H34 119.3 . . ?
C3 C4 C7 120.9(3) . . ?
C3 C4 C5 116.6(3) . . ?
C5 C4 C7 122.5(3) . . ?
C36 C35 C34 121.4(3) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C33 C38 H38 119.3 . . ?
C37 C38 C33 121.4(3) . . ?
C37 C38 H38 119.3 . . ?
C8 C7 H7 106.7 . . ?
C8 C7 C16 110.9(3) . . ?
C4 C7 C8 113.2(3) . . ?
C4 C7 H7 106.7 . . ?
C4 C7 C16 112.2(2) . . ?
C16 C7 H7 106.7 . . ?
C8 C13 C14 120.8(3) . . ?
C12 C13 C8 119.7(3) . . ?
C12 C13 C14 119.4(3) . . ?
C6 C1 C2 116.1(3) . . ?
C6 C1 C18 120.7(3) . . ?
C2 C1 C18 123.3(3) . . ?
C28 C27 C22 120.5(3) . . ?
C28 C27 C26 117.8(4) . . ?
C26 C27 C22 121.7(4) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.8(3) . . ?
C10 C9 H9 119.1 . . ?
C4 C3 H3 118.9 . . ?
C4 C3 C2 122.1(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 122.0(3) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C36 C37 H37 119.1 . . ?
C38 C37 C36 121.9(3) . . ?
C38 C37 H37 119.1 . . ?
C36 C39 C41 112.0(3) . . ?
C42 C39 C36 110.8(3) . . ?
C42 C39 C41 105.5(4) . . ?
C40 C39 C36 109.7(3) . . ?
C40 C39 C42 109.7(4) . . ?
C40 C39 C41 109.0(4) . . ?
C7 C16 H16 108.1 . . ?
C15 C16 C7 109.3(3) . . ?
C15 C16 H16 108.1 . . ?
C17 C16 C7 112.4(3) . . ?
C17 C16 H16 108.1 . . ?
C17 C16 C15 110.7(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 H2 119.2 . . ?
C19 C18 C1 111.5(4) . . ?
C19 C18 C21 105.9(5) . . ?
C20 C18 C1 109.9(4) . . ?
C20 C18 C19 109.9(5) . . ?
C20 C18 C21 106.7(5) . . ?
C21 C18 C1 112.8(4) . . ?
C13 C14 C15 118.0(3) . . ?
O1 C14 C13 120.1(4) . . ?
O1 C14 C15 121.9(4) . . ?
C22 C23 H23 107.8 . . ?
C24 C23 C22 110.0(3) . . ?
C24 C23 H23 107.8 . . ?
C32 C23 C22 112.1(3) . . ?
C32 C23 H23 107.8 . . ?
C32 C23 C24 111.2(4) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C14 C15 C16 114.8(3) . . ?
C14 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C13 C12 H12 119.0 . . ?
C11 C12 C13 121.9(3) . . ?
C11 C12 H12 119.0 . . ?
C27 C28 H28 119.4 . . ?
C29 C28 C27 121.3(4) . . ?
C29 C28 H28 119.4 . . ?
C27 C26 C25 120.4(4) . . ?
C31 C26 C27 119.4(5) . . ?
C31 C26 C25 120.1(5) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.5(4) . . ?
C12 C11 H11 120.8 . . ?
C24 C25 C26 117.9(4) . . ?
O2 C25 C26 121.8(6) . . ?
O2 C25 C24 120.4(6) . . ?
C23 C24 H24A 108.3 . . ?
C23 C24 H24B 108.3 . . ?
C25 C24 C23 115.9(4) . . ?
C25 C24 H24A 108.3 . . ?
C25 C24 H24B 108.3 . . ?
H24A C24 H24B 107.4 . . ?
C26 C31 H31 119.0 . . ?
C30 C31 C26 122.0(5) . . ?
C30 C31 H31 119.0 . . ?
C23 C32 H32A 109.5 . . ?
C23 C32 H32B 109.5 . . ?
C23 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.2(6) . . ?
C30 C29 H29 119.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C31 C30 C29 119.3(5) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C33 C22 C27 C28 -30.3(4) . . . . ?
C33 C22 C27 C26 151.5(3) . . . . ?
C33 C22 C23 C24 -176.0(3) . . . . ?
C33 C22 C23 C32 59.6(4) . . . . ?
C33 C34 C35 C36 0.1(5) . . . . ?
C33 C38 C37 C36 0.7(5) . . . . ?
C8 C7 C16 C15 -54.3(4) . . . . ?
C8 C7 C16 C17 -177.6(3) . . . . ?
C8 C13 C14 O1 174.5(4) . . . . ?
C8 C13 C14 C15 -4.5(5) . . . . ?
C8 C13 C12 C11 0.2(5) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C22 C33 C34 C35 -179.2(3) . . . . ?
C22 C33 C38 C37 178.8(3) . . . . ?
C22 C27 C28 C29 -178.4(3) . . . . ?
C22 C27 C26 C25 0.5(5) . . . . ?
C22 C27 C26 C31 178.4(3) . . . . ?
C22 C23 C24 C25 52.3(5) . . . . ?
C34 C33 C22 C27 -54.0(4) . . . . ?
C34 C33 C22 C23 72.6(4) . . . . ?
C34 C33 C38 C37 -0.1(4) . . . . ?
C4 C7 C16 C15 178.0(3) . . . . ?
C4 C7 C16 C17 54.7(4) . . . . ?
C4 C3 C2 C1 0.2(6) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C35 C36 C37 C38 -0.9(5) . . . . ?
C35 C36 C39 C42 131.4(4) . . . . ?
C35 C36 C39 C41 13.9(5) . . . . ?
C35 C36 C39 C40 -107.3(4) . . . . ?
C38 C33 C22 C27 127.2(3) . . . . ?
C38 C33 C22 C23 -106.2(3) . . . . ?
C38 C33 C34 C35 -0.3(4) . . . . ?
C7 C8 C13 C14 1.4(4) . . . . ?
C7 C8 C13 C12 179.3(3) . . . . ?
C7 C8 C9 C10 -179.2(3) . . . . ?
C7 C4 C3 C2 -180.0(3) . . . . ?
C7 C4 C5 C6 -179.9(3) . . . . ?
C7 C16 C15 C14 53.1(4) . . . . ?
C13 C8 C7 C4 156.0(3) . . . . ?
C13 C8 C7 C16 28.8(4) . . . . ?
C13 C8 C9 C10 -1.1(5) . . . . ?
C13 C14 C15 C16 -23.9(5) . . . . ?
C13 C12 C11 C10 -1.5(6) . . . . ?
O1 C14 C15 C16 157.1(4) . . . . ?
C27 C22 C23 C24 -49.3(4) . . . . ?
C27 C22 C23 C32 -173.6(3) . . . . ?
C27 C28 C29 C30 0.0(7) . . . . ?
C27 C26 C25 C24 0.3(6) . . . . ?
C27 C26 C25 O2 179.9(4) . . . . ?
C27 C26 C31 C30 0.0(7) . . . . ?
C9 C8 C7 C4 -25.9(4) . . . . ?
C9 C8 C7 C16 -153.1(3) . . . . ?
C9 C8 C13 C14 -176.8(3) . . . . ?
C9 C8 C13 C12 1.1(4) . . . . ?
C9 C10 C11 C12 1.6(6) . . . . ?
C3 C4 C7 C8 114.4(3) . . . . ?
C3 C4 C7 C16 -119.1(4) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C5 C4 C7 C8 -64.9(4) . . . . ?
C5 C4 C7 C16 61.6(4) . . . . ?
C5 C4 C3 C2 -0.6(5) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
C6 C1 C18 C19 -58.2(6) . . . . ?
C6 C1 C18 C20 63.8(5) . . . . ?
C6 C1 C18 C21 -177.2(4) . . . . ?
C37 C36 C35 C34 0.5(4) . . . . ?
C37 C36 C39 C42 -48.8(4) . . . . ?
C37 C36 C39 C41 -166.4(4) . . . . ?
C37 C36 C39 C40 72.4(5) . . . . ?
C39 C36 C35 C34 -179.8(3) . . . . ?
C39 C36 C37 C38 179.4(3) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C2 C1 C18 C19 123.1(5) . . . . ?
C2 C1 C18 C20 -114.8(5) . . . . ?
C2 C1 C18 C21 4.2(6) . . . . ?
C18 C1 C6 C5 -178.5(3) . . . . ?
C18 C1 C2 C3 178.7(3) . . . . ?
C14 C13 C12 C11 178.1(3) . . . . ?
C23 C22 C27 C28 -156.7(3) . . . . ?
C23 C22 C27 C26 25.1(4) . . . . ?
C12 C13 C14 O1 -3.4(6) . . . . ?
C12 C13 C14 C15 177.6(3) . . . . ?
C28 C27 C26 C25 -177.7(3) . . . . ?
C28 C27 C26 C31 0.1(5) . . . . ?
C28 C29 C30 C31 0.1(8) . . . . ?
C26 C27 C28 C29 -0.1(5) . . . . ?
C26 C25 C24 C23 -27.6(6) . . . . ?
C26 C31 C30 C29 -0.1(9) . . . . ?
C25 C26 C31 C30 177.8(5) . . . . ?
C31 C26 C25 C24 -177.5(4) . . . . ?
C31 C26 C25 O2 2.1(7) . . . . ?
O2 C25 C24 C23 152.8(4) . . . . ?
C32 C23 C24 C25 177.1(4) . . . . ?
C17 C16 C15 C14 177.4(4) . . . . ?

_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 1.484
_oxdiff_exptl_absorpt_empirical_full_min 0.659
####################################################################### 
# 
# 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_218
_database_code_depnum_ccdc_archive 'CCDC 2018584'
loop_
_audit_author_name
_audit_author_address
'Peijun Liu'
;Zunyi Medical Univeristy
China
;
_audit_update_record             
;
2020-07-23 deposited with the CCDC.	2020-10-07 downloaded from the CCDC.
;
_audit_creation_date             2019-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 O'
_chemical_formula_sum            'C20 H20 O'
_chemical_formula_weight         276.36
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4699(8)
_cell_length_b                   7.4654(6)
_cell_length_c                   17.2634(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.445(6)
_cell_angle_gamma                90
_cell_volume                     1468.88(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2580
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0130
_cell_measurement_theta_min      2.8060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6549
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.375
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  24.00   1.00    3.50    --  -11.59 -99.00-150.00   39
  2  ω     34.00  84.00   1.00    3.50    --   11.74-178.00-180.00   50
  3  ω    -52.00  65.00   1.00    3.50    --   11.74   0.00 -60.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0244118000
_diffrn_orient_matrix_UB_12      0.0841050000
_diffrn_orient_matrix_UB_13      -0.0120182000
_diffrn_orient_matrix_UB_21      -0.0572716000
_diffrn_orient_matrix_UB_22      -0.0354151000
_diffrn_orient_matrix_UB_23      0.0006393000
_diffrn_orient_matrix_UB_31      0.0008121000
_diffrn_orient_matrix_UB_32      0.0261797000
_diffrn_orient_matrix_UB_33      0.0395709000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2160
_reflns_number_total             2583
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.041
_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)+(0.0450P)²+0.6119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1118
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B), C20(H20A,H20B), C19(H19A,H19B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C12(H12), C6(H6), C2(H2), C5(H5), C4(H4), C3(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 0.60434(11) 1.00891(17) 0.68124(7) 0.0272(3) Uani 1 1 d . . . . .
C8 C 0.47117(14) 0.4127(2) 0.62500(9) 0.0175(4) Uani 1 1 d . . . . .
H8 H 0.485521 0.290193 0.628341 0.021 Uiso 1 1 calc R . . . .
C9 C 0.55477(14) 0.5308(2) 0.66033(9) 0.0173(4) Uani 1 1 d . . . . .
C13 C 0.62140(15) 0.8476(2) 0.68863(9) 0.0207(4) Uani 1 1 d . . . . .
C10 C 0.53347(14) 0.7149(2) 0.65483(9) 0.0181(4) Uani 1 1 d . . . . .
C7 C 0.36638(14) 0.4735(2) 0.58471(9) 0.0182(4) Uani 1 1 d . . . . .
C1 C 0.27898(14) 0.3466(2) 0.54570(9) 0.0188(4) Uani 1 1 d . . . . .
C11 C 0.42784(15) 0.7763(2) 0.61440(10) 0.0212(4) Uani 1 1 d . . . . .
H11 H 0.413388 0.898742 0.610708 0.025 Uiso 1 1 calc R . . . .
C16 C 0.66773(14) 0.4578(2) 0.70255(9) 0.0187(4) Uani 1 1 d . . . . .
H16 H 0.648066 0.348431 0.729677 0.022 Uiso 1 1 calc R . . . .
C12 C 0.34578(15) 0.6586(2) 0.58032(9) 0.0205(4) Uani 1 1 d . . . . .
H12 H 0.276118 0.701755 0.554157 0.025 Uiso 1 1 calc R . . . .
C14 C 0.73460(15) 0.7757(2) 0.72964(10) 0.0222(4) Uani 1 1 d . . . . .
H14A H 0.762903 0.857601 0.771177 0.027 Uiso 1 1 calc R . . . .
H14B H 0.792687 0.772014 0.692933 0.027 Uiso 1 1 calc R . . . .
C6 C 0.31468(15) 0.1941(2) 0.50794(9) 0.0208(4) Uani 1 1 d . . . . .
H6 H 0.394211 0.167853 0.509840 0.025 Uiso 1 1 calc R . . . .
C2 C 0.15824(15) 0.3797(3) 0.54328(9) 0.0222(4) Uani 1 1 d . . . . .
H2 H 0.132308 0.478520 0.569295 0.027 Uiso 1 1 calc R . . . .
C17 C 0.75241(14) 0.4049(3) 0.64358(10) 0.0225(4) Uani 1 1 d . . . . .
H17A H 0.715151 0.316729 0.607666 0.027 Uiso 1 1 calc R . . . .
H17B H 0.770134 0.509452 0.613659 0.027 Uiso 1 1 calc R . . . .
C15 C 0.72351(15) 0.5886(2) 0.76425(9) 0.0203(4) Uani 1 1 d . . . . .
H15 H 0.670721 0.597869 0.804941 0.024 Uiso 1 1 calc R . . . .
C5 C 0.23334(16) 0.0814(3) 0.46774(10) 0.0254(4) Uani 1 1 d . . . . .
H5 H 0.258538 -0.019844 0.443003 0.031 Uiso 1 1 calc R . . . .
C4 C 0.11427(16) 0.1188(3) 0.46415(10) 0.0264(4) Uani 1 1 d . . . . .
H4 H 0.059819 0.044544 0.436030 0.032 Uiso 1 1 calc R . . . .
C3 C 0.07717(15) 0.2671(3) 0.50266(10) 0.0260(4) Uani 1 1 d . . . . .
H3 H -0.002576 0.291246 0.501265 0.031 Uiso 1 1 calc R . . . .
C20 C 0.84136(15) 0.5155(3) 0.80263(10) 0.0251(4) Uani 1 1 d . . . . .
H20A H 0.879062 0.606538 0.836892 0.030 Uiso 1 1 calc R . . . .
H20B H 0.826672 0.412492 0.834364 0.030 Uiso 1 1 calc R . . . .
C19 C 0.92451(15) 0.4607(3) 0.74379(11) 0.0268(4) Uani 1 1 d . . . . .
H19A H 0.948121 0.566277 0.716721 0.032 Uiso 1 1 calc R . . . .
H19B H 0.994432 0.407029 0.771066 0.032 Uiso 1 1 calc R . . . .
C18 C 0.86618(15) 0.3275(3) 0.68463(10) 0.0263(4) Uani 1 1 d . . . . .
H18A H 0.849381 0.217326 0.710994 0.032 Uiso 1 1 calc R . . . .
H18B H 0.919268 0.299661 0.646364 0.032 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.224(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.392(2) . ?
C8 C7 1.395(2) . ?
C9 C10 1.397(2) . ?
C9 C16 1.515(2) . ?
C13 C10 1.486(2) . ?
C13 C14 1.506(2) . ?
C10 C11 1.405(2) . ?
C7 C1 1.485(2) . ?
C7 C12 1.403(2) . ?
C1 C6 1.396(2) . ?
C1 C2 1.403(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(2) . ?
C16 H16 0.9800 . ?
C16 C17 1.535(2) . ?
C16 C15 1.531(2) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.531(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.384(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.527(2) . ?
C15 H15 0.9800 . ?
C15 C20 1.537(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.388(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.383(3) . ?
C3 H3 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.525(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.525(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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
C9 C8 H8 119.2 . . ?
C9 C8 C7 121.67(16) . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 119.11(15) . . ?
C8 C9 C16 119.53(15) . . ?
C10 C9 C16 121.35(15) . . ?
O1 C13 C10 121.44(16) . . ?
O1 C13 C14 121.25(16) . . ?
C10 C13 C14 117.27(15) . . ?
C9 C10 C13 121.57(15) . . ?
C9 C10 C11 119.29(16) . . ?
C11 C10 C13 119.12(16) . . ?
C8 C7 C1 121.24(16) . . ?
C8 C7 C12 118.55(16) . . ?
C12 C7 C1 120.20(15) . . ?
C6 C1 C7 120.91(15) . . ?
C6 C1 C2 118.03(16) . . ?
C2 C1 C7 121.01(16) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.07(17) . . ?
C12 C11 H11 119.5 . . ?
C9 C16 H16 107.4 . . ?
C9 C16 C17 110.13(13) . . ?
C9 C16 C15 111.92(14) . . ?
C17 C16 H16 107.4 . . ?
C15 C16 H16 107.4 . . ?
C15 C16 C17 112.28(14) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.31(16) . . ?
C11 C12 H12 119.8 . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C13 C14 C15 113.81(14) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.90(16) . . ?
C5 C6 H6 119.6 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.86(17) . . ?
C3 C2 H2 119.6 . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 111.15(14) . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C16 C15 H15 107.5 . . ?
C16 C15 C20 110.63(14) . . ?
C14 C15 C16 110.92(14) . . ?
C14 C15 H15 107.5 . . ?
C14 C15 C20 112.61(14) . . ?
C20 C15 H15 107.5 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.31(18) . . ?
C4 C5 H5 119.8 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.59(17) . . ?
C3 C4 H4 120.2 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.28(16) . . ?
C4 C3 H3 119.9 . . ?
C15 C20 H20A 108.9 . . ?
C15 C20 H20B 108.9 . . ?
H20A C20 H20B 107.8 . . ?
C19 C20 C15 113.17(14) . . ?
C19 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C18 C19 C20 111.15(14) . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 C17 110.61(15) . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?

_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 1.441
_oxdiff_exptl_absorpt_empirical_full_min 0.641
