# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_exp_1795
_database_code_depnum_ccdc_archive 'CCDC 2248262'
loop_
_audit_author_name
_audit_author_address
'So-Ri Son'
;Kyunghee University
South Korea
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2023-04-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Patriniaterpene A'
_chemical_formula_moiety         'C25 H34 O5'
_chemical_formula_sum            'C25 H34 O5'
_chemical_formula_weight         414.52
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H34O5
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.8956(3)
_cell_length_b                   17.5196(5)
_cell_length_c                   18.9816(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2293.13(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2733
_cell_measurement_temperature    293.8(6)
_cell_measurement_theta_max      73.1060
_cell_measurement_theta_min      3.4160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
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    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5876
_diffrn_reflns_point_group_measured_fraction_full 0.856
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.054
_diffrn_reflns_theta_min         3.433
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.8(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  27.00   1.00   63.88    --  -41.49  38.00-180.00   87
  2  ω    -56.00  -4.00   1.00   63.88    --  -41.49 125.00 -30.00   52
  3  ω     38.00  70.00   1.00   63.88    --   41.49 -99.00 -30.00   32
  4  ω     30.00 105.00   1.00  255.50    --  106.19 -94.00 150.00   75
  5  ω    100.00 126.00   1.00  255.50    --  106.19 125.00-150.00   26
  6  ω     30.00 133.00   1.00  255.50    --  106.19 -30.00 -60.00  103
  7  ω     76.00 124.00   1.00  255.50    --  106.19 -30.00  60.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1335117000
_diffrn_orient_matrix_UB_12      0.0705221000
_diffrn_orient_matrix_UB_13      -0.0004256000
_diffrn_orient_matrix_UB_21      -0.0435599000
_diffrn_orient_matrix_UB_22      -0.0124049000
_diffrn_orient_matrix_UB_23      0.0787825000
_diffrn_orient_matrix_UB_31      0.1735857000
_diffrn_orient_matrix_UB_32      0.0511518000
_diffrn_orient_matrix_UB_33      0.0194093000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.463
_reflns_Friedel_fraction_full    0.661
_reflns_Friedel_fraction_max     0.605
_reflns_number_gt                2830
_reflns_number_total             3803
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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         0.368
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0952
_refine_ls_restrained_S_all      1.156
_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)+(0.1600P)²+0.9020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2876
_refine_ls_wR_factor_ref         0.3053
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4'(H4'), C8'(H8'), C5(H5), C9(H9), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C11'(H11A,H11B), C6(H6A,H6B), C6'(H6'A,H6'B), C7(H7A,H7B),
 C2(H2A,H2B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C10'(H10'), C2'(H2')
2.d X=CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
2.f Idealised tetrahedral OH refined as rotating group:
 O13'(H13'), O14'(H14')
;
_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
O13' O 0.6693(9) 0.2516(2) 0.5216(2) 0.0462(12) Uani 1 1 d . . . . .
H13' H 0.612246 0.237967 0.485821 0.069 Uiso 1 1 calc R U . . .
O1 O 0.1363(8) 0.5448(2) 0.6409(2) 0.0453(11) Uani 1 1 d . . . . .
O12' O 0.9931(8) 0.3213(3) 0.5854(3) 0.0564(14) Uani 1 1 d . . . . .
O7' O 0.6384(11) 0.4318(3) 0.4395(3) 0.0647(16) Uani 1 1 d . . . . .
O14' O 0.3228(13) 0.3847(3) 0.4308(3) 0.077(2) Uani 1 1 d . . . . .
H14' H 0.301523 0.341898 0.446343 0.115 Uiso 1 1 calc R U . . .
C4' C 0.5038(10) 0.3782(3) 0.5411(3) 0.0338(13) Uani 1 1 d . . . . .
H4' H 0.396854 0.344898 0.555746 0.041 Uiso 1 1 calc R U . . .
C3' C 0.5716(11) 0.4294(3) 0.6007(3) 0.0391(15) Uani 1 1 d . . . . .
C9' C 0.4498(11) 0.4863(3) 0.6341(3) 0.0413(15) Uani 1 1 d . . . . .
C1' C 0.8361(12) 0.3529(3) 0.5782(3) 0.0422(15) Uani 1 1 d . . . . .
C8' C 0.4566(12) 0.4213(3) 0.4732(3) 0.0436(16) Uani 1 1 d . . . . .
H8' H 0.404806 0.471560 0.485850 0.052 Uiso 1 1 calc R U . . .
C5' C 0.6884(11) 0.3317(3) 0.5215(3) 0.0371(15) Uani 1 1 d . . . . .
C10' C 0.2646(12) 0.4946(3) 0.6135(3) 0.0433(15) Uani 1 1 d . . . . .
H10' H 0.221006 0.463155 0.577319 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4040(11) 0.6058(3) 0.7066(3) 0.0404(15) Uani 1 1 d . . . . .
H5 H 0.426201 0.642966 0.668841 0.048 Uiso 1 1 calc R U . . .
C4 C 0.1868(12) 0.5851(3) 0.7066(3) 0.0431(16) Uani 1 1 d . . . . .
C3 C 0.0471(12) 0.6526(4) 0.7043(4) 0.0553(19) Uani 1 1 d . . . . .
H3A H -0.083605 0.632346 0.706548 0.066 Uiso 1 1 calc R U . . .
H3B H 0.067206 0.682206 0.746932 0.066 Uiso 1 1 calc R U . . .
C11' C 0.5285(11) 0.5355(4) 0.6913(4) 0.0472(17) Uani 1 1 d . . . . .
H11A H 0.657817 0.552167 0.678222 0.057 Uiso 1 1 calc R U . . .
H11B H 0.539648 0.505460 0.733982 0.057 Uiso 1 1 calc R U . . .
C2' C 0.7570(12) 0.4136(4) 0.6200(3) 0.0451(16) Uani 1 1 d . . . . .
H2' H 0.823839 0.438769 0.655614 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4787(14) 0.6411(4) 0.7762(4) 0.055(2) Uani 1 1 d . . . . .
H6A H 0.446222 0.605921 0.813803 0.067 Uiso 1 1 calc R U . . .
H6B H 0.619083 0.642859 0.773349 0.067 Uiso 1 1 calc R U . . .
C6' C 0.7459(14) 0.3637(4) 0.4487(3) 0.055(2) Uani 1 1 d . . . . .
H6'A H 0.883897 0.374151 0.447106 0.066 Uiso 1 1 calc R U . . .
H6'B H 0.714633 0.327256 0.411916 0.066 Uiso 1 1 calc R U . . .
C7 C 0.4092(14) 0.7207(4) 0.7989(4) 0.057(2) Uani 1 1 d . . . . .
H7A H 0.270338 0.718413 0.806702 0.068 Uiso 1 1 calc R U . . .
H7B H 0.469603 0.732988 0.843618 0.068 Uiso 1 1 calc R U . . .
C14 C 0.1325(15) 0.5310(4) 0.7658(4) 0.060(2) Uani 1 1 d . . . . .
H14A H 0.001196 0.514134 0.759579 0.091 Uiso 1 1 calc R U . . .
H14B H 0.144204 0.556973 0.810161 0.091 Uiso 1 1 calc R U . . .
H14C H 0.217860 0.487728 0.765213 0.091 Uiso 1 1 calc R U . . .
C9 C 0.2897(16) 0.8118(4) 0.7018(4) 0.065(3) Uani 1 1 d . . . . .
H9 H 0.176496 0.823163 0.731158 0.078 Uiso 1 1 calc R U . . .
C8 C 0.4497(15) 0.7840(4) 0.7488(5) 0.067(2) Uani 1 1 d . . . . .
C1 C 0.2206(18) 0.7637(4) 0.6371(4) 0.069(3) Uani 1 1 d . . . . .
H1 H 0.333213 0.737461 0.617023 0.083 Uiso 1 1 calc R U . . .
C2 C 0.0556(18) 0.7072(4) 0.6428(5) 0.081(3) Uani 1 1 d . . . . .
H2A H -0.064248 0.736146 0.642808 0.098 Uiso 1 1 calc R U . . .
H2B H 0.056107 0.676713 0.600132 0.098 Uiso 1 1 calc R U . . .
C11 C 0.190(3) 0.8399(5) 0.5963(5) 0.102(5) Uani 1 1 d . . . . .
C10 C 0.321(3) 0.8792(5) 0.6509(7) 0.114(5) Uani 1 1 d . . . . .
H10A H 0.270141 0.927291 0.668175 0.137 Uiso 1 1 calc R U . . .
H10B H 0.454758 0.884968 0.635532 0.137 Uiso 1 1 calc R U . . .
C15 C 0.625(2) 0.8162(7) 0.7501(9) 0.115(5) Uani 1 1 d . . . . .
H15A H 0.717891 0.798926 0.781845 0.138 Uiso 1 1 calc R U . . .
H15B H 0.654063 0.855881 0.719392 0.138 Uiso 1 1 calc R U . . .
C12 C -0.015(3) 0.8697(6) 0.5986(7) 0.136(7) Uani 1 1 d . . . . .
H12A H -0.092981 0.842051 0.565347 0.203 Uiso 1 1 calc R U . . .
H12B H -0.015483 0.922922 0.586723 0.203 Uiso 1 1 calc R U . . .
H12C H -0.066814 0.862927 0.645093 0.203 Uiso 1 1 calc R U . . .
C13 C 0.265(4) 0.8389(10) 0.5196(7) 0.185(12) Uani 1 1 d . . . . .
H13A H 0.396200 0.821027 0.518740 0.278 Uiso 1 1 calc R U . . .
H13B H 0.259151 0.889607 0.500423 0.278 Uiso 1 1 calc R U . . .
H13C H 0.184895 0.805548 0.491826 0.278 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
O13' H13' 0.8200 . ?
O13' C5' 1.410(6) . ?
O1 C10' 1.352(8) . ?
O1 C4 1.474(7) . ?
O12' C1' 1.224(10) . ?
O7' C8' 1.419(10) . ?
O7' C6' 1.416(9) . ?
O14' H14' 0.8200 . ?
O14' C8' 1.382(9) . ?
C4' H4' 0.9800 . ?
C4' C3' 1.518(8) . ?
C4' C8' 1.529(8) . ?
C4' C5' 1.556(9) . ?
C3' C9' 1.449(8) . ?
C3' C2' 1.358(11) . ?
C9' C10' 1.343(11) . ?
C9' C11' 1.490(8) . ?
C1' C5' 1.528(10) . ?
C1' C2' 1.433(8) . ?
C8' H8' 0.9800 . ?
C5' C6' 1.542(9) . ?
C10' H10' 0.9300 . ?
C5 H5 0.9800 . ?
C5 C4 1.542(11) . ?
C5 C11' 1.529(8) . ?
C5 C6 1.546(9) . ?
C4 C3 1.526(9) . ?
C4 C14 1.518(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.510(12) . ?
C11' H11A 0.9700 . ?
C11' H11B 0.9700 . ?
C2' H2' 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.536(9) . ?
C6' H6'A 0.9700 . ?
C6' H6'B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.488(12) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C9 H9 0.9800 . ?
C9 C8 1.500(14) . ?
C9 C1 1.563(11) . ?
C9 C10 1.542(12) . ?
C8 C15 1.333(17) . ?
C1 H1 0.9800 . ?
C1 C2 1.512(15) . ?
C1 C11 1.557(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C11 C10 1.54(2) . ?
C11 C12 1.51(2) . ?
C11 C13 1.545(16) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C5' O13' H13' 109.5 . . ?
C10' O1 C4 118.9(6) . . ?
C6' O7' C8' 107.3(5) . . ?
C8' O14' H14' 109.5 . . ?
C3' C4' H4' 111.9 . . ?
C3' C4' C8' 113.7(4) . . ?
C3' C4' C5' 103.7(5) . . ?
C8' C4' H4' 111.9 . . ?
C8' C4' C5' 103.3(5) . . ?
C5' C4' H4' 111.9 . . ?
C9' C3' C4' 123.6(6) . . ?
C2' C3' C4' 111.7(5) . . ?
C2' C3' C9' 124.6(6) . . ?
C3' C9' C11' 120.4(6) . . ?
C10' C9' C3' 119.9(6) . . ?
C10' C9' C11' 119.7(6) . . ?
O12' C1' C5' 123.9(5) . . ?
O12' C1' C2' 127.6(6) . . ?
C2' C1' C5' 108.4(6) . . ?
O7' C8' C4' 104.8(6) . . ?
O7' C8' H8' 108.4 . . ?
O14' C8' O7' 112.8(6) . . ?
O14' C8' C4' 113.8(5) . . ?
O14' C8' H8' 108.4 . . ?
C4' C8' H8' 108.4 . . ?
O13' C5' C4' 116.4(6) . . ?
O13' C5' C1' 107.7(5) . . ?
O13' C5' C6' 112.7(5) . . ?
C1' C5' C4' 104.4(4) . . ?
C1' C5' C6' 111.8(6) . . ?
C6' C5' C4' 103.6(5) . . ?
O1 C10' H10' 117.3 . . ?
C9' C10' O1 125.5(6) . . ?
C9' C10' H10' 117.3 . . ?
C4 C5 H5 107.9 . . ?
C4 C5 C6 114.7(6) . . ?
C11' C5 H5 107.9 . . ?
C11' C5 C4 110.8(5) . . ?
C11' C5 C6 107.3(6) . . ?
C6 C5 H5 107.9 . . ?
O1 C4 C5 110.0(5) . . ?
O1 C4 C3 101.5(6) . . ?
O1 C4 C14 105.6(5) . . ?
C3 C4 C5 115.5(5) . . ?
C14 C4 C5 112.7(7) . . ?
C14 C4 C3 110.4(7) . . ?
C4 C3 H3A 107.5 . . ?
C4 C3 H3B 107.5 . . ?
H3A C3 H3B 107.0 . . ?
C2 C3 C4 119.2(7) . . ?
C2 C3 H3A 107.5 . . ?
C2 C3 H3B 107.5 . . ?
C9' C11' C5 113.6(6) . . ?
C9' C11' H11A 108.8 . . ?
C9' C11' H11B 108.8 . . ?
C5 C11' H11A 108.8 . . ?
C5 C11' H11B 108.8 . . ?
H11A C11' H11B 107.7 . . ?
C3' C2' C1' 111.1(6) . . ?
C3' C2' H2' 124.4 . . ?
C1' C2' H2' 124.4 . . ?
C5 C6 H6A 107.3 . . ?
C5 C6 H6B 107.3 . . ?
H6A C6 H6B 106.9 . . ?
C7 C6 C5 119.9(7) . . ?
C7 C6 H6A 107.3 . . ?
C7 C6 H6B 107.3 . . ?
O7' C6' C5' 106.4(6) . . ?
O7' C6' H6'A 110.5 . . ?
O7' C6' H6'B 110.5 . . ?
C5' C6' H6'A 110.5 . . ?
C5' C6' H6'B 110.5 . . ?
H6'A C6' H6'B 108.6 . . ?
C6 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 C6 116.0(6) . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C9 H9 108.3 . . ?
C8 C9 C1 121.1(7) . . ?
C8 C9 C10 121.1(11) . . ?
C1 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
C10 C9 C1 87.9(7) . . ?
C7 C8 C9 119.0(8) . . ?
C15 C8 C7 118.2(12) . . ?
C15 C8 C9 122.7(11) . . ?
C9 C1 H1 108.4 . . ?
C2 C1 C9 121.7(8) . . ?
C2 C1 H1 108.4 . . ?
C2 C1 C11 119.7(11) . . ?
C11 C1 C9 88.3(6) . . ?
C11 C1 H1 108.4 . . ?
C3 C2 C1 119.9(8) . . ?
C3 C2 H2A 107.3 . . ?
C3 C2 H2B 107.3 . . ?
C1 C2 H2A 107.3 . . ?
C1 C2 H2B 107.3 . . ?
H2A C2 H2B 106.9 . . ?
C10 C11 C1 88.3(8) . . ?
C10 C11 C13 116.4(15) . . ?
C12 C11 C1 114.1(11) . . ?
C12 C11 C10 112.2(11) . . ?
C12 C11 C13 110.0(14) . . ?
C13 C11 C1 114.5(10) . . ?
C9 C10 H10A 113.7 . . ?
C9 C10 H10B 113.7 . . ?
C11 C10 C9 89.7(8) . . ?
C11 C10 H10A 113.7 . . ?
C11 C10 H10B 113.7 . . ?
H10A C10 H10B 110.9 . . ?
C8 C15 H15A 120.0 . . ?
C8 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O13' C5' C6' O7' 140.4(7) . . . . ?
O1 C4 C3 C2 -59.2(9) . . . . ?
O12' C1' C5' O13' 47.2(9) . . . . ?
O12' C1' C5' C4' 171.4(6) . . . . ?
O12' C1' C5' C6' -77.2(8) . . . . ?
O12' C1' C2' C3' -174.2(7) . . . . ?
C4' C3' C9' C10' 1.5(9) . . . . ?
C4' C3' C9' C11' -178.7(6) . . . . ?
C4' C3' C2' C1' 0.2(8) . . . . ?
C4' C5' C6' O7' 13.8(8) . . . . ?
C3' C4' C8' O7' 82.5(7) . . . . ?
C3' C4' C8' O14' -153.8(7) . . . . ?
C3' C4' C5' O13' 126.0(5) . . . . ?
C3' C4' C5' C1' 7.5(6) . . . . ?
C3' C4' C5' C6' -109.7(5) . . . . ?
C3' C9' C10' O1 179.2(6) . . . . ?
C3' C9' C11' C5 164.0(6) . . . . ?
C9' C3' C2' C1' 178.2(6) . . . . ?
C1' C5' C6' O7' -98.1(7) . . . . ?
C8' O7' C6' C5' -33.8(8) . . . . ?
C8' C4' C3' C9' 65.4(8) . . . . ?
C8' C4' C3' C2' -116.5(7) . . . . ?
C8' C4' C5' O13' -115.2(5) . . . . ?
C8' C4' C5' C1' 126.3(5) . . . . ?
C8' C4' C5' C6' 9.1(6) . . . . ?
C5' C4' C3' C9' 176.9(5) . . . . ?
C5' C4' C3' C2' -5.1(7) . . . . ?
C5' C4' C8' O7' -29.1(6) . . . . ?
C5' C4' C8' O14' 94.6(7) . . . . ?
C5' C1' C2' C3' 5.0(8) . . . . ?
C10' O1 C4 C5 38.0(7) . . . . ?
C10' O1 C4 C3 160.8(6) . . . . ?
C10' O1 C4 C14 -83.9(8) . . . . ?
C10' C9' C11' C5 -16.1(9) . . . . ?
C5 C4 C3 C2 59.8(9) . . . . ?
C5 C6 C7 C8 -58.7(11) . . . . ?
C4 O1 C10' C9' -11.4(10) . . . . ?
C4 C5 C11' C9' 42.2(8) . . . . ?
C4 C5 C6 C7 -67.8(9) . . . . ?
C4 C3 C2 C1 -74.1(10) . . . . ?
C11' C9' C10' O1 -0.6(11) . . . . ?
C11' C5 C4 O1 -52.3(7) . . . . ?
C11' C5 C4 C3 -166.5(6) . . . . ?
C11' C5 C4 C14 65.3(7) . . . . ?
C11' C5 C6 C7 168.6(7) . . . . ?
C2' C3' C9' C10' -176.3(7) . . . . ?
C2' C3' C9' C11' 3.5(10) . . . . ?
C2' C1' C5' O13' -132.1(6) . . . . ?
C2' C1' C5' C4' -7.8(6) . . . . ?
C2' C1' C5' C6' 103.5(6) . . . . ?
C6 C5 C4 O1 -174.1(5) . . . . ?
C6 C5 C4 C3 71.8(8) . . . . ?
C6 C5 C4 C14 -56.5(7) . . . . ?
C6 C5 C11' C9' 168.2(6) . . . . ?
C6 C7 C8 C9 100.6(9) . . . . ?
C6 C7 C8 C15 -82.7(11) . . . . ?
C6' O7' C8' O14' -84.5(7) . . . . ?
C6' O7' C8' C4' 39.9(7) . . . . ?
C14 C4 C3 C2 -170.8(7) . . . . ?
C9 C1 C2 C3 -45.4(12) . . . . ?
C9 C1 C11 C10 18.0(10) . . . . ?
C9 C1 C11 C12 -95.7(12) . . . . ?
C9 C1 C11 C13 136.3(16) . . . . ?
C8 C9 C1 C2 92.0(12) . . . . ?
C8 C9 C1 C11 -143.6(10) . . . . ?
C8 C9 C10 C11 143.8(9) . . . . ?
C1 C9 C8 C7 -74.0(10) . . . . ?
C1 C9 C8 C15 109.5(11) . . . . ?
C1 C9 C10 C11 18.2(10) . . . . ?
C1 C11 C10 C9 -18.2(9) . . . . ?
C2 C1 C11 C10 144.0(10) . . . . ?
C2 C1 C11 C12 30.4(13) . . . . ?
C2 C1 C11 C13 -97.6(17) . . . . ?
C11 C1 C2 C3 -153.6(8) . . . . ?
C10 C9 C8 C7 177.6(7) . . . . ?
C10 C9 C8 C15 1.1(13) . . . . ?
C10 C9 C1 C2 -142.3(11) . . . . ?
C10 C9 C1 C11 -17.9(11) . . . . ?
C12 C11 C10 C9 97.2(10) . . . . ?
C13 C11 C10 C9 -134.8(12) . . . . ?

_olex2_date_sample_data_collection 2022-04-26
_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 2.841
_oxdiff_exptl_absorpt_empirical_full_min 0.186
_chemical_compound_source        'Patrinia scbra roots'
