# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

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

data_10
_database_code_depnum_ccdc_archive 'CCDC 2356914'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2024-05-21 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_audit_creation_date             2023-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        GS-7s-Li
_chemical_formula_moiety         'C12 H22 O2'
_chemical_formula_sum            'C12 H22 O2'
_chemical_formula_weight         198.30
_chemical_absolute_configuration ad
_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      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                   6.3202(3)
_cell_length_b                   11.5648(5)
_cell_length_c                   15.4255(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1127.48(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10153
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.56
_cell_measurement_theta_min      4.78
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.840
_exptl_absorpt_coefficient_mu    0.60
_exptl_absorpt_correction_T_max  0.9228
_exptl_absorpt_correction_T_min  0.7297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14494
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         70.531
_diffrn_reflns_theta_min         4.779
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Axo Cu'
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                1877
_reflns_number_total             2141
_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       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.189.0 (STOE, 2022)'
_computing_data_reduction        
;
X-Area Integrate 2.5.11.0 (STOE, 2022)
X-Area LANA 2.7.9.0 (STOE, 2022)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.051
_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)+(0.0584P)²+0.0661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0958
_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:
 C6(H6), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6666(2) 0.62632(14) 0.53817(10) 0.0191(4) Uani 1 1 d . . . . .
H1 H 0.623443 0.690960 0.555599 0.029 Uiso 1 1 calc GR . . . .
O2 O 0.3970(2) 0.78833(14) 0.59952(11) 0.0217(4) Uani 1 1 d . . . . .
H2 H 0.349032 0.825715 0.557180 0.033 Uiso 1 1 calc GR . . . .
C1 C 0.5077(3) 0.53839(19) 0.55691(14) 0.0160(5) Uani 1 1 d . . . . .
C2 C 0.5501(3) 0.4919(2) 0.65073(14) 0.0174(5) Uani 1 1 d . . . . .
C3 C 0.7770(3) 0.4442(2) 0.65458(14) 0.0199(5) Uani 1 1 d . . . . .
H3A H 0.878003 0.508709 0.646322 0.024 Uiso 1 1 calc R . . . .
H3B H 0.802397 0.410841 0.712757 0.024 Uiso 1 1 calc R . . . .
C4 C 0.8192(4) 0.3515(2) 0.58592(15) 0.0233(5) Uani 1 1 d . . . . .
H4A H 0.970348 0.329133 0.587916 0.028 Uiso 1 1 calc R . . . .
H4B H 0.733674 0.282058 0.599178 0.028 Uiso 1 1 calc R . . . .
C5 C 0.7650(4) 0.3943(2) 0.49506(15) 0.0225(5) Uani 1 1 d . . . . .
H5A H 0.780368 0.329521 0.453549 0.027 Uiso 1 1 calc R . . . .
H5B H 0.866682 0.455391 0.478175 0.027 Uiso 1 1 calc R . . . .
C6 C 0.5391(4) 0.4426(2) 0.48903(14) 0.0187(5) Uani 1 1 d . . . . .
H6 H 0.439605 0.378333 0.503715 0.022 Uiso 1 1 calc R . . . .
C7 C 0.2894(3) 0.5960(2) 0.55122(14) 0.0179(5) Uani 1 1 d . . . . .
H7A H 0.271118 0.629038 0.492481 0.021 Uiso 1 1 calc R . . . .
H7B H 0.178824 0.536449 0.559587 0.021 Uiso 1 1 calc R . . . .
C8 C 0.2583(3) 0.6918(2) 0.61829(15) 0.0199(5) Uani 1 1 d . . . . .
H8 H 0.108108 0.718865 0.616091 0.024 Uiso 1 1 calc R . . . .
C9 C 0.3083(3) 0.6506(2) 0.70978(14) 0.0199(5) Uani 1 1 d . . . . .
H9A H 0.198556 0.594930 0.728555 0.024 Uiso 1 1 calc R . . . .
H9B H 0.304253 0.717490 0.749831 0.024 Uiso 1 1 calc R . . . .
C10 C 0.5265(4) 0.5927(2) 0.71530(14) 0.0187(5) Uani 1 1 d . . . . .
H10A H 0.548535 0.563406 0.774914 0.022 Uiso 1 1 calc R . . . .
H10B H 0.637274 0.651122 0.703381 0.022 Uiso 1 1 calc R . . . .
C11 C 0.3939(4) 0.3961(2) 0.67739(15) 0.0202(5) Uani 1 1 d . . . . .
H11A H 0.248558 0.424313 0.670874 0.030 Uiso 1 1 calc GR . . . .
H11B H 0.418894 0.374630 0.737993 0.030 Uiso 1 1 calc GR . . . .
H11C H 0.414812 0.328259 0.640259 0.030 Uiso 1 1 calc GR . . . .
C12 C 0.4908(4) 0.4807(2) 0.39598(16) 0.0262(5) Uani 1 1 d . . . . .
H12A H 0.340566 0.500707 0.391082 0.039 Uiso 1 1 calc GR . . . .
H12B H 0.523592 0.417344 0.355959 0.039 Uiso 1 1 calc GR . . . .
H12C H 0.577156 0.548279 0.381362 0.039 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C1 1.458(3) . ?
O2 H2 0.8400 . ?
O2 C8 1.449(3) . ?
C1 C2 1.567(3) . ?
C1 C6 1.537(3) . ?
C1 C7 1.534(3) . ?
C2 C3 1.538(3) . ?
C2 C10 1.541(3) . ?
C2 C11 1.540(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.530(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.525(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.536(3) . ?
C6 H6 1.0000 . ?
C6 C12 1.532(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.528(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.523(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.535(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C1 O1 H1 109.5 . . ?
C8 O2 H2 109.5 . . ?
O1 C1 C2 107.73(16) . . ?
O1 C1 C6 106.15(16) . . ?
O1 C1 C7 107.76(17) . . ?
C6 C1 C2 111.10(18) . . ?
C7 C1 C2 110.83(17) . . ?
C7 C1 C6 112.97(17) . . ?
C3 C2 C1 108.56(17) . . ?
C3 C2 C10 109.68(18) . . ?
C3 C2 C11 109.22(18) . . ?
C10 C2 C1 108.72(18) . . ?
C11 C2 C1 112.57(17) . . ?
C11 C2 C10 108.06(18) . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 C2 112.79(19) . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 C3 111.7(2) . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C4 C5 C6 112.48(18) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C1 C6 H6 107.5 . . ?
C5 C6 C1 109.96(18) . . ?
C5 C6 H6 107.5 . . ?
C12 C6 C1 113.9(2) . . ?
C12 C6 C5 110.28(19) . . ?
C12 C6 H6 107.5 . . ?
C1 C7 H7A 109.0 . . ?
C1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C1 113.07(17) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
O2 C8 C7 110.19(17) . . ?
O2 C8 H8 109.0 . . ?
O2 C8 C9 107.47(18) . . ?
C7 C8 H8 109.0 . . ?
C9 C8 C7 111.98(19) . . ?
C9 C8 H8 109.0 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C8 C9 C10 111.98(17) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C2 C10 H10A 109.1 . . ?
C2 C10 H10B 109.1 . . ?
C9 C10 C2 112.40(18) . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ent-18
_database_code_depnum_ccdc_archive 'CCDC 2356916'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2024-05-21 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_audit_creation_date             2023-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        SGS-3
_chemical_formula_moiety         'C12 H18 O'
_chemical_formula_sum            'C12 H18 O'
_chemical_formula_weight         178.26
_chemical_absolute_configuration ad
_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      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                   7.32486(22)
_cell_length_b                   9.9130(3)
_cell_length_c                   14.0128(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1017.49(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13654
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.54
_cell_measurement_theta_min      5.47
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    0.55
_exptl_absorpt_correction_T_max  0.8823
_exptl_absorpt_correction_T_min  0.7672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9605
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         70.545
_diffrn_reflns_theta_min         5.466
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Axo Cu'
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                1845
_reflns_number_total             1918
_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       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.189.0 (STOE, 2022)'
_computing_data_reduction        
;
X-Area Integrate 2.5.11.0 (STOE, 2022)
X-Area LANA 2.7.9.0 (STOE, 2022)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1918
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.048
_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)+(0.0451P)²+0.1435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0751
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(3)
 0.1(3)
2. 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
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.29848(16) 0.41516(13) 0.45986(9) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.4593(2) 0.52724(15) 0.58126(11) 0.0191(3) Uani 1 1 d . . . . .
H1 H 0.348865 0.553419 0.611620 0.023 Uiso 1 1 calc R . . . .
C2 C 0.6176(2) 0.57027(15) 0.61931(10) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.8014(2) 0.54107(15) 0.57191(11) 0.0175(3) Uani 1 1 d . . . . .
C4 C 0.7764(2) 0.49184(17) 0.46858(11) 0.0217(4) Uani 1 1 d . . . . .
H4A H 0.749090 0.570371 0.427331 0.026 Uiso 1 1 calc R . . . .
H4B H 0.892414 0.451637 0.446171 0.026 Uiso 1 1 calc R . . . .
C5 C 0.6237(2) 0.38771(17) 0.45753(12) 0.0242(4) Uani 1 1 d . . . . .
H5A H 0.609079 0.364412 0.389251 0.029 Uiso 1 1 calc R . . . .
H5B H 0.656625 0.304438 0.492521 0.029 Uiso 1 1 calc R . . . .
C6 C 0.4468(2) 0.44226(16) 0.49563(11) 0.0218(3) Uani 1 1 d . . . . .
C7 C 0.6244(2) 0.64772(16) 0.71238(11) 0.0204(3) Uani 1 1 d . . . . .
H7 H 0.688994 0.588863 0.759488 0.024 Uiso 1 1 calc R . . . .
C8 C 0.7401(2) 0.77654(17) 0.70157(13) 0.0248(4) Uani 1 1 d . . . . .
H8A H 0.677703 0.839552 0.657521 0.030 Uiso 1 1 calc R . . . .
H8B H 0.751131 0.821470 0.764399 0.030 Uiso 1 1 calc R . . . .
C9 C 0.9299(2) 0.74531(17) 0.66330(12) 0.0254(4) Uani 1 1 d . . . . .
H9A H 0.996478 0.687890 0.709437 0.030 Uiso 1 1 calc R . . . .
H9B H 0.999228 0.830220 0.655038 0.030 Uiso 1 1 calc R . . . .
C10 C 0.9146(2) 0.67252(16) 0.56778(11) 0.0216(3) Uani 1 1 d . . . . .
H10A H 1.038979 0.650701 0.544796 0.026 Uiso 1 1 calc R . . . .
H10B H 0.858125 0.734297 0.520786 0.026 Uiso 1 1 calc R . . . .
C11 C 0.4385(2) 0.6816(2) 0.75562(13) 0.0282(4) Uani 1 1 d . . . . .
H11A H 0.369864 0.738815 0.711294 0.042 Uiso 1 1 calc GR . . . .
H11B H 0.455989 0.729659 0.816051 0.042 Uiso 1 1 calc GR . . . .
H11C H 0.370502 0.598081 0.767247 0.042 Uiso 1 1 calc GR . . . .
C12 C 0.9055(2) 0.43315(16) 0.62957(12) 0.0221(3) Uani 1 1 d . . . . .
H12A H 0.916420 0.462466 0.696115 0.033 Uiso 1 1 calc GR . . . .
H12B H 1.027510 0.420811 0.602294 0.033 Uiso 1 1 calc GR . . . .
H12C H 0.838573 0.347613 0.626938 0.033 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O C6 1.226(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.346(2) . ?
C1 C6 1.469(2) . ?
C2 C3 1.529(2) . ?
C2 C7 1.514(2) . ?
C3 C4 1.539(2) . ?
C3 C10 1.546(2) . ?
C3 C12 1.542(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.530(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.502(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.540(2) . ?
C7 C11 1.528(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.522(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.525(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C2 C1 H1 118.0 . . ?
C2 C1 C6 123.98(14) . . ?
C6 C1 H1 118.0 . . ?
C1 C2 C3 121.78(13) . . ?
C1 C2 C7 122.02(13) . . ?
C7 C2 C3 116.19(12) . . ?
C2 C3 C4 111.35(12) . . ?
C2 C3 C10 109.23(12) . . ?
C2 C3 C12 109.82(12) . . ?
C4 C3 C10 107.22(12) . . ?
C4 C3 C12 109.37(13) . . ?
C12 C3 C10 109.81(12) . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 C3 113.35(13) . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.59(13) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
O C6 C1 120.96(15) . . ?
O C6 C5 122.69(15) . . ?
C1 C6 C5 116.31(13) . . ?
C2 C7 H7 106.8 . . ?
C2 C7 C8 110.71(13) . . ?
C2 C7 C11 115.08(13) . . ?
C8 C7 H7 106.8 . . ?
C11 C7 H7 106.8 . . ?
C11 C7 C8 110.31(13) . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.64(13) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C8 C9 C10 109.81(13) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C3 C10 H10A 108.8 . . ?
C3 C10 H10B 108.8 . . ?
C9 C10 C3 113.91(13) . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(3)
2 0.1(3)
####################################################################### 
# 
# 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_18
_database_code_depnum_ccdc_archive 'CCDC 2356915'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2024-05-21 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_audit_creation_date             2023-07-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        GS-3
_chemical_formula_moiety         'C12 H18 O'
_chemical_formula_sum            'C12 H18 O'
_chemical_formula_weight         178.26
_chemical_absolute_configuration ad
_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      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                   7.3252(3)
_cell_length_b                   9.8946(3)
_cell_length_c                   14.0386(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1017.52(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12547
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.72
_cell_measurement_theta_min      5.47
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.55
_exptl_absorpt_correction_T_max  0.9299
_exptl_absorpt_correction_T_min  0.7561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8835
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         70.403
_diffrn_reflns_theta_min         5.470
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   ?
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                1837
_reflns_number_total             1918
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 740 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1918
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.037
_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)+(0.0517P)²+0.1327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0815
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.29814(17) 0.41555(14) 0.53969(10) 0.0327(3) Uani 1 1 d . . . . .
C1 C 0.4464(2) 0.44261(18) 0.50409(12) 0.0238(4) Uani 1 1 d . . . . .
C2 C 0.4592(2) 0.52744(17) 0.41849(12) 0.0209(4) Uani 1 1 d . . . . .
H2 H 0.348866 0.553608 0.388078 0.025 Uiso 1 1 calc R . . . .
C3 C 0.6174(2) 0.57035(16) 0.38053(11) 0.0184(3) Uani 1 1 d . . . . .
C4 C 0.6247(2) 0.64768(18) 0.28732(12) 0.0227(4) Uani 1 1 d . . . . .
H4 H 0.689371 0.588518 0.240465 0.027 Uiso 1 1 calc R . . . .
C5 C 0.7400(2) 0.77652(18) 0.29789(13) 0.0266(4) Uani 1 1 d . . . . .
H5A H 0.751248 0.821195 0.235064 0.032 Uiso 1 1 calc R . . . .
H5B H 0.677329 0.839863 0.341604 0.032 Uiso 1 1 calc R . . . .
C6 C 0.9297(2) 0.74552(18) 0.33642(13) 0.0275(4) Uani 1 1 d . . . . .
H6A H 0.998842 0.830687 0.344651 0.033 Uiso 1 1 calc R . . . .
H6B H 0.996666 0.687957 0.290533 0.033 Uiso 1 1 calc R . . . .
C7 C 0.9143(2) 0.67288(17) 0.43176(12) 0.0237(4) Uani 1 1 d . . . . .
H7A H 0.858025 0.735009 0.478584 0.028 Uiso 1 1 calc R . . . .
H7B H 1.038634 0.650965 0.454706 0.028 Uiso 1 1 calc R . . . .
C8 C 0.8011(2) 0.54160(16) 0.42808(11) 0.0193(4) Uani 1 1 d . . . . .
C9 C 0.7758(2) 0.49221(18) 0.53128(12) 0.0237(4) Uani 1 1 d . . . . .
H9A H 0.891746 0.451892 0.553698 0.028 Uiso 1 1 calc R . . . .
H9B H 0.748526 0.570916 0.572433 0.028 Uiso 1 1 calc R . . . .
C10 C 0.6236(2) 0.38836(18) 0.54235(13) 0.0260(4) Uani 1 1 d . . . . .
H10A H 0.656718 0.304793 0.507626 0.031 Uiso 1 1 calc R . . . .
H10B H 0.608889 0.365282 0.610536 0.031 Uiso 1 1 calc R . . . .
C11 C 0.4386(2) 0.6814(2) 0.24404(13) 0.0305(4) Uani 1 1 d . . . . .
H11A H 0.371107 0.597576 0.232081 0.046 Uiso 1 1 calc GR . . . .
H11B H 0.456043 0.729981 0.183894 0.046 Uiso 1 1 calc GR . . . .
H11C H 0.369465 0.738196 0.288395 0.046 Uiso 1 1 calc GR . . . .
C12 C 0.9049(2) 0.43323(17) 0.37058(12) 0.0238(4) Uani 1 1 d . . . . .
H12A H 0.836959 0.347939 0.372609 0.036 Uiso 1 1 calc GR . . . .
H12B H 1.026321 0.419899 0.398293 0.036 Uiso 1 1 calc GR . . . .
H12C H 0.917223 0.463005 0.304318 0.036 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O C1 1.225(2) . ?
C1 C2 1.469(2) . ?
C1 C10 1.504(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.345(2) . ?
C3 C4 1.517(2) . ?
C3 C8 1.528(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.536(2) . ?
C4 C11 1.529(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.523(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.523(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.542(2) . ?
C8 C9 1.540(2) . ?
C8 C12 1.542(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.524(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
O C1 C2 121.00(16) . . ?
O C1 C10 122.78(16) . . ?
C2 C1 C10 116.18(14) . . ?
C1 C2 H2 118.0 . . ?
C3 C2 C1 124.03(15) . . ?
C3 C2 H2 118.0 . . ?
C2 C3 C4 122.09(14) . . ?
C2 C3 C8 121.80(14) . . ?
C4 C3 C8 116.10(13) . . ?
C3 C4 H4 106.8 . . ?
C3 C4 C5 110.76(14) . . ?
C3 C4 C11 114.95(13) . . ?
C5 C4 H4 106.8 . . ?
C11 C4 H4 106.8 . . ?
C11 C4 C5 110.33(14) . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.65(14) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C5 C6 C7 109.86(14) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C6 C7 C8 114.07(13) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C3 C8 C7 109.35(13) . . ?
C3 C8 C9 111.34(13) . . ?
C3 C8 C12 109.55(13) . . ?
C7 C8 C12 109.75(13) . . ?
C9 C8 C7 107.49(13) . . ?
C9 C8 C12 109.33(14) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C8 113.45(13) . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C1 C10 C9 110.74(14) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ent-19
_database_code_depnum_ccdc_archive 'CCDC 2356917'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2024-05-21 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_audit_creation_date             2023-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        SGS-4
_chemical_formula_moiety         'C12 H20 O'
_chemical_formula_sum            'C12 H20 O'
_chemical_formula_weight         180.28
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   36.7093(10)
_cell_length_b                   26.4549(9)
_cell_length_c                   6.8153(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6618.6(3)
_cell_formula_units_Z            24
_cell_measurement_reflns_used    39213
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.78
_cell_measurement_theta_min      3.98
_shelx_estimated_absorpt_T_max   0.906
_shelx_estimated_absorpt_T_min   0.751
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_correction_T_min  0.7149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.086
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            77736
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         67.744
_diffrn_reflns_theta_min         4.819
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
 2471 frames, detector distance = 60 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   ?
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                9654
_reflns_number_total             11933
_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       
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.189.0 (STOE, 2022)
;
_computing_data_reduction        
;
X-Area Integrate 2.5.11.0 (STOE, 2022)
X-Area LANA 2.7.9.0 (STOE, 2022)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 3497 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.00056(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     722
_refine_ls_number_reflns         11933
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0766
_refine_ls_restrained_S_all      1.027
_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)+(0.1139P)²+4.4557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1929
_refine_ls_wR_factor_ref         0.2194
_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:
 C1A(H1A), C10A(H10A), C1B(H1B), C10B(H10B), C1C(H1C), C10C(H10C), C1D(H1D),
 C10D(H10D), C1E(H1E), C10E(H10E), C1F(H1F), C10F(H10F)
2.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C3A(H3AA,H3AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C9A(H9AA,
 H9AB), C2B(H2BA,H2BB), C3B(H3BA,H3BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB),
 C9B(H9BA,H9BB), C2C(H2CA,H2CB), C3C(H3CA,H3CB), C7C(H7CA,H7CB), C8C(H8CA,H8CB),
  C9C(H9CA,H9CB), C2D(H2DA,H2DB), C3D(H3DA,H3DB), C7D(H7DA,H7DB), C8D(H8DA,
 H8DB), C9D(H9DA,H9DB), C2E(H2EA,H2EB), C3E(H3EA,H3EB), C7E(H7EA,H7EB),
 C8E(H8EA,H8EB), C9E(H9EA,H9EB), C2F(H2FA,H2FB), C3F(H3FA,H3FB), C7F(H7FA,H7FB),
  C8F(H8FA,H8FB), C9F(H9FA,H9FB)
2.c Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C6B(H6B), C6C(H6C), C6D(H6D), C6E(H6E), C6F(H6F)
2.d Idealised Me refined as rotating group:
 C11A(H11A,H11B,H11C), C12A(H12A,H12B,H12C), C11B(H11D,H11E,H11F), C12B(H12D,
 H12E,H12F), C11C(H11G,H11H,H11I), C12C(H12G,H12H,H12I), C11D(H11J,H11K,H11L),
 C12D(H12J,H12K,H12L), C11E(H11M,H11N,H11O), C12E(H12M,H12N,H12O), C11F(H11P,
 H11Q,H11R), C12F(H12P,H12Q,H12R)
2.e Idealised tetrahedral OH refined as rotating group:
 OA(HA), OB(HB), OC(HC), OD(HD), OE(HE), OF(HF)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
OA O 0.35818(9) 0.49986(15) 0.4851(6) 0.0599(9) Uani 1 1 d . . . . .
HA H 0.348007 0.486256 0.388190 0.090 Uiso 1 1 calc GR . . . .
C1A C 0.39459(13) 0.4805(2) 0.5046(9) 0.0542(12) Uani 1 1 d . . . . .
H1A H 0.404739 0.493017 0.631798 0.065 Uiso 1 1 calc R . . . .
C2A C 0.41808(16) 0.5005(2) 0.3422(10) 0.0656(15) Uani 1 1 d . . . . .
H2AA H 0.422333 0.537130 0.361506 0.079 Uiso 1 1 calc R . . . .
H2AB H 0.405615 0.495818 0.214655 0.079 Uiso 1 1 calc R . . . .
C3A C 0.45396(15) 0.4729(3) 0.3407(11) 0.0695(16) Uani 1 1 d . . . . .
H3AA H 0.465718 0.476669 0.470598 0.083 Uiso 1 1 calc R . . . .
H3AB H 0.470142 0.488544 0.241628 0.083 Uiso 1 1 calc R . . . .
C4A C 0.44972(13) 0.4165(2) 0.2942(9) 0.0584(14) Uani 1 1 d . . . . .
C5A C 0.41887(13) 0.3942(2) 0.4171(8) 0.0514(12) Uani 1 1 d . . . . .
C6A C 0.39491(13) 0.4236(2) 0.5096(8) 0.0505(12) Uani 1 1 d . . . . .
H6A H 0.376534 0.407384 0.584819 0.061 Uiso 1 1 calc R . . . .
C7A C 0.48599(14) 0.3909(3) 0.3559(10) 0.0659(16) Uani 1 1 d . . . . .
H7AA H 0.505490 0.402088 0.265442 0.079 Uiso 1 1 calc R . . . .
H7AB H 0.492541 0.402543 0.489340 0.079 Uiso 1 1 calc R . . . .
C8A C 0.48458(14) 0.3336(3) 0.3553(10) 0.0668(16) Uani 1 1 d . . . . .
H8AA H 0.508183 0.319965 0.401396 0.080 Uiso 1 1 calc R . . . .
H8AB H 0.480456 0.321398 0.219810 0.080 Uiso 1 1 calc R . . . .
C9A C 0.45402(15) 0.3147(2) 0.4884(9) 0.0628(14) Uani 1 1 d . . . . .
H9AA H 0.459236 0.324600 0.625667 0.075 Uiso 1 1 calc R . . . .
H9AB H 0.452932 0.277356 0.482532 0.075 Uiso 1 1 calc R . . . .
C10A C 0.41688(14) 0.3370(2) 0.4253(9) 0.0549(13) Uani 1 1 d . . . . .
H10A H 0.412344 0.325075 0.288132 0.066 Uiso 1 1 calc R . . . .
C11A C 0.44274(14) 0.4068(3) 0.0756(9) 0.0675(17) Uani 1 1 d . . . . .
H11A H 0.420651 0.424693 0.034653 0.101 Uiso 1 1 calc GR . . . .
H11B H 0.439577 0.370416 0.053546 0.101 Uiso 1 1 calc GR . . . .
H11C H 0.463535 0.418947 -0.001208 0.101 Uiso 1 1 calc GR . . . .
C12A C 0.38622(16) 0.3158(2) 0.5510(10) 0.0680(16) Uani 1 1 d . . . . .
H12A H 0.389448 0.326851 0.687123 0.102 Uiso 1 1 calc GR . . . .
H12B H 0.386678 0.278761 0.545460 0.102 Uiso 1 1 calc GR . . . .
H12C H 0.362771 0.328060 0.501463 0.102 Uiso 1 1 calc GR . . . .
OB O 0.32672(10) 0.46504(15) 0.1493(6) 0.0554(9) Uani 1 1 d . . . . .
HB H 0.323216 0.476306 0.035646 0.083 Uiso 1 1 calc GR . . . .
C1B C 0.31407(13) 0.4139(2) 0.1602(9) 0.0527(12) Uani 1 1 d . . . . .
H1B H 0.317362 0.402216 0.298561 0.063 Uiso 1 1 calc R . . . .
C2B C 0.33580(13) 0.3792(2) 0.0302(9) 0.0585(14) Uani 1 1 d . . . . .
H2BA H 0.361042 0.376371 0.080037 0.070 Uiso 1 1 calc R . . . .
H2BB H 0.336739 0.393018 -0.104749 0.070 Uiso 1 1 calc R . . . .
C3B C 0.31765(14) 0.3269(2) 0.0284(10) 0.0606(14) Uani 1 1 d . . . . .
H3BA H 0.316089 0.314145 0.164695 0.073 Uiso 1 1 calc R . . . .
H3BB H 0.333093 0.303249 -0.047254 0.073 Uiso 1 1 calc R . . . .
C4B C 0.27921(14) 0.3277(2) -0.0617(9) 0.0535(12) Uani 1 1 d . . . . .
C5B C 0.25797(12) 0.3742(2) 0.0120(8) 0.0482(11) Uani 1 1 d . . . . .
C6B C 0.27407(13) 0.4112(2) 0.1135(8) 0.0518(12) Uani 1 1 d . . . . .
H6B H 0.259051 0.437829 0.159966 0.062 Uiso 1 1 calc R . . . .
C7B C 0.25931(15) 0.2791(2) 0.0041(10) 0.0612(14) Uani 1 1 d . . . . .
H7BA H 0.270805 0.249730 -0.061269 0.073 Uiso 1 1 calc R . . . .
H7BB H 0.262615 0.274890 0.147321 0.073 Uiso 1 1 calc R . . . .
C8B C 0.21837(15) 0.2788(2) -0.0421(10) 0.0657(15) Uani 1 1 d . . . . .
H8BA H 0.214756 0.278178 -0.185984 0.079 Uiso 1 1 calc R . . . .
H8BB H 0.207106 0.248001 0.013713 0.079 Uiso 1 1 calc R . . . .
C9B C 0.20009(14) 0.3250(2) 0.0428(9) 0.0630(15) Uani 1 1 d . . . . .
H9BA H 0.202111 0.324224 0.187606 0.076 Uiso 1 1 calc R . . . .
H9BB H 0.173893 0.324580 0.008321 0.076 Uiso 1 1 calc R . . . .
C10B C 0.21764(13) 0.3741(2) -0.0359(8) 0.0535(12) Uani 1 1 d . . . . .
H10B H 0.215457 0.373263 -0.182112 0.064 Uiso 1 1 calc R . . . .
C11B C 0.28210(15) 0.3296(2) -0.2886(9) 0.0593(14) Uani 1 1 d . . . . .
H11D H 0.294171 0.361017 -0.328305 0.089 Uiso 1 1 calc GR . . . .
H11E H 0.257629 0.328339 -0.345837 0.089 Uiso 1 1 calc GR . . . .
H11F H 0.296326 0.300622 -0.334950 0.089 Uiso 1 1 calc GR . . . .
C12B C 0.19703(14) 0.4206(3) 0.0344(10) 0.0664(16) Uani 1 1 d . . . . .
H12D H 0.198528 0.422734 0.177714 0.100 Uiso 1 1 calc GR . . . .
H12E H 0.171438 0.417966 -0.005330 0.100 Uiso 1 1 calc GR . . . .
H12F H 0.207826 0.450937 -0.023892 0.100 Uiso 1 1 calc GR . . . .
OC O 0.31229(10) 0.49994(16) 0.7880(6) 0.0599(10) Uani 1 1 d . . . . .
HC H 0.327562 0.503655 0.697419 0.090 Uiso 1 1 calc GR . . . .
C1C C 0.27839(14) 0.5221(2) 0.7311(8) 0.0558(13) Uani 1 1 d . . . . .
H1C H 0.262151 0.522751 0.848842 0.067 Uiso 1 1 calc R . . . .
C2C C 0.25938(13) 0.4916(2) 0.5717(8) 0.0530(12) Uani 1 1 d . . . . .
H2CA H 0.252340 0.457971 0.623084 0.064 Uiso 1 1 calc R . . . .
H2CB H 0.275922 0.486637 0.458655 0.064 Uiso 1 1 calc R . . . .
C3C C 0.22548(13) 0.5209(2) 0.5077(9) 0.0537(12) Uani 1 1 d . . . . .
H3CA H 0.209882 0.527113 0.623728 0.064 Uiso 1 1 calc R . . . .
H3CB H 0.211398 0.500068 0.413880 0.064 Uiso 1 1 calc R . . . .
C4C C 0.23490(12) 0.5720(2) 0.4105(8) 0.0497(12) Uani 1 1 d . . . . .
C5C C 0.26507(12) 0.5989(2) 0.5207(8) 0.0505(12) Uani 1 1 d . . . . .
C6C C 0.28385(14) 0.5758(2) 0.6638(8) 0.0540(12) Uani 1 1 d . . . . .
H6C H 0.302170 0.594996 0.728291 0.065 Uiso 1 1 calc R . . . .
C7C C 0.20016(13) 0.6053(2) 0.4144(9) 0.0553(13) Uani 1 1 d . . . . .
H7CA H 0.181279 0.589405 0.331068 0.066 Uiso 1 1 calc R . . . .
H7CB H 0.190682 0.606568 0.550292 0.066 Uiso 1 1 calc R . . . .
C8C C 0.20675(14) 0.6592(2) 0.3426(9) 0.0579(13) Uani 1 1 d . . . . .
H8CA H 0.213814 0.658676 0.202438 0.069 Uiso 1 1 calc R . . . .
H8CB H 0.184081 0.679199 0.355385 0.069 Uiso 1 1 calc R . . . .
C9C C 0.23697(15) 0.6836(2) 0.4637(9) 0.0590(13) Uani 1 1 d . . . . .
H9CA H 0.228924 0.686425 0.601910 0.071 Uiso 1 1 calc R . . . .
H9CB H 0.241593 0.718158 0.413852 0.071 Uiso 1 1 calc R . . . .
C10C C 0.27235(14) 0.6530(2) 0.4549(8) 0.0559(13) Uani 1 1 d . . . . .
H10C H 0.279843 0.651399 0.314005 0.067 Uiso 1 1 calc R . . . .
C11C C 0.24642(13) 0.5621(2) 0.1972(8) 0.0546(13) Uani 1 1 d . . . . .
H11G H 0.252102 0.594283 0.132959 0.082 Uiso 1 1 calc GR . . . .
H11H H 0.226484 0.545361 0.127058 0.082 Uiso 1 1 calc GR . . . .
H11I H 0.268019 0.540333 0.195662 0.082 Uiso 1 1 calc GR . . . .
C12C C 0.30283(16) 0.6801(2) 0.5658(10) 0.0656(15) Uani 1 1 d . . . . .
H12G H 0.295647 0.684757 0.703103 0.098 Uiso 1 1 calc GR . . . .
H12H H 0.307246 0.713199 0.505501 0.098 Uiso 1 1 calc GR . . . .
H12I H 0.325143 0.659840 0.559780 0.098 Uiso 1 1 calc GR . . . .
OD O 0.52900(10) 0.24322(16) -0.3197(6) 0.0588(9) Uani 1 1 d . . . . .
HD H 0.514521 0.245291 -0.224633 0.088 Uiso 1 1 calc GR . . . .
C1D C 0.56405(14) 0.2627(2) -0.2626(8) 0.0534(12) Uani 1 1 d . . . . .
H1D H 0.581019 0.257829 -0.375824 0.064 Uiso 1 1 calc R . . . .
C2D C 0.57986(14) 0.2346(2) -0.0885(8) 0.0543(12) Uani 1 1 d . . . . .
H2DA H 0.585482 0.199268 -0.125762 0.065 Uiso 1 1 calc R . . . .
H2DB H 0.562049 0.233996 0.020560 0.065 Uiso 1 1 calc R . . . .
C3D C 0.61446(13) 0.2616(2) -0.0242(8) 0.0525(12) Uani 1 1 d . . . . .
H3DA H 0.631606 0.262797 -0.136224 0.063 Uiso 1 1 calc R . . . .
H3DB H 0.626155 0.241770 0.081792 0.063 Uiso 1 1 calc R . . . .
C4D C 0.60770(12) 0.3157(2) 0.0496(7) 0.0469(11) Uani 1 1 d . . . . .
C5D C 0.58072(12) 0.3428(2) -0.0844(7) 0.0480(11) Uani 1 1 d . . . . .
C6D C 0.56181(13) 0.3185(2) -0.2227(8) 0.0505(12) Uani 1 1 d . . . . .
H6D H 0.545744 0.337897 -0.301774 0.061 Uiso 1 1 calc R . . . .
C7D C 0.64454(12) 0.3442(2) 0.0470(8) 0.0537(12) Uani 1 1 d . . . . .
H7DA H 0.660565 0.329483 0.148934 0.064 Uiso 1 1 calc R . . . .
H7DB H 0.656357 0.338560 -0.081734 0.064 Uiso 1 1 calc R . . . .
C8D C 0.64147(13) 0.4009(2) 0.0823(8) 0.0534(12) Uani 1 1 d . . . . .
H8DA H 0.632813 0.407278 0.217627 0.064 Uiso 1 1 calc R . . . .
H8DB H 0.665705 0.416901 0.067300 0.064 Uiso 1 1 calc R . . . .
C9D C 0.61492(13) 0.4240(2) -0.0641(8) 0.0527(12) Uani 1 1 d . . . . .
H9DA H 0.624477 0.419389 -0.198752 0.063 Uiso 1 1 calc R . . . .
H9DB H 0.612721 0.460694 -0.038989 0.063 Uiso 1 1 calc R . . . .
C10D C 0.57713(13) 0.3993(2) -0.0486(8) 0.0507(12) Uani 1 1 d . . . . .
H10D H 0.568710 0.403729 0.089857 0.061 Uiso 1 1 calc R . . . .
C11D C 0.59283(13) 0.3136(2) 0.2603(8) 0.0535(13) Uani 1 1 d . . . . .
H11J H 0.587451 0.347930 0.305833 0.080 Uiso 1 1 calc GR . . . .
H11K H 0.611065 0.298177 0.346614 0.080 Uiso 1 1 calc GR . . . .
H11L H 0.570494 0.293315 0.262785 0.080 Uiso 1 1 calc GR . . . .
C12D C 0.54928(14) 0.4260(2) -0.1809(9) 0.0577(13) Uani 1 1 d . . . . .
H12J H 0.547302 0.461565 -0.142166 0.087 Uiso 1 1 calc GR . . . .
H12K H 0.525481 0.409588 -0.167000 0.087 Uiso 1 1 calc GR . . . .
H12L H 0.557272 0.423873 -0.317802 0.087 Uiso 1 1 calc GR . . . .
OE O 0.51271(10) 0.20697(15) 0.3215(6) 0.0544(9) Uani 1 1 d . . . . .
HE H 0.517270 0.222017 0.427215 0.082 Uiso 1 1 calc GR . . . .
C1E C 0.52654(13) 0.1563(2) 0.3311(8) 0.0532(12) Uani 1 1 d . . . . .
H1E H 0.523090 0.140569 0.198873 0.064 Uiso 1 1 calc R . . . .
C2E C 0.50565(13) 0.1247(2) 0.4775(9) 0.0550(13) Uani 1 1 d . . . . .
H2EA H 0.480407 0.119400 0.430661 0.066 Uiso 1 1 calc R . . . .
H2EB H 0.504590 0.142402 0.605412 0.066 Uiso 1 1 calc R . . . .
C3E C 0.52490(13) 0.0738(2) 0.5011(9) 0.0554(12) Uani 1 1 d . . . . .
H3EA H 0.526307 0.057090 0.371433 0.066 Uiso 1 1 calc R . . . .
H3EB H 0.510171 0.052022 0.588496 0.066 Uiso 1 1 calc R . . . .
C4E C 0.56359(13) 0.0785(2) 0.5862(8) 0.0501(11) Uani 1 1 d . . . . .
C5E C 0.58378(13) 0.1233(2) 0.4898(8) 0.0484(11) Uani 1 1 d . . . . .
C6E C 0.56662(13) 0.1565(2) 0.3740(8) 0.0503(12) Uani 1 1 d . . . . .
H6E H 0.580915 0.182216 0.314526 0.060 Uiso 1 1 calc R . . . .
C7E C 0.58412(14) 0.0290(2) 0.5407(9) 0.0546(12) Uani 1 1 d . . . . .
H7EA H 0.573159 0.001295 0.618427 0.066 Uiso 1 1 calc R . . . .
H7EB H 0.580813 0.020725 0.400183 0.066 Uiso 1 1 calc R . . . .
C8E C 0.62499(14) 0.0314(2) 0.5856(9) 0.0576(13) Uani 1 1 d . . . . .
H8EA H 0.628693 0.036114 0.728297 0.069 Uiso 1 1 calc R . . . .
H8EB H 0.636709 -0.000722 0.546547 0.069 Uiso 1 1 calc R . . . .
C9E C 0.64238(13) 0.0749(2) 0.4750(9) 0.0575(13) Uani 1 1 d . . . . .
H9EA H 0.639655 0.069418 0.332071 0.069 Uiso 1 1 calc R . . . .
H9EB H 0.668733 0.076280 0.505464 0.069 Uiso 1 1 calc R . . . .
C10E C 0.62445(13) 0.1253(2) 0.5322(8) 0.0533(12) Uani 1 1 d . . . . .
H10E H 0.627310 0.129180 0.677330 0.064 Uiso 1 1 calc R . . . .
C11E C 0.56112(14) 0.0875(2) 0.8088(8) 0.0522(12) Uani 1 1 d . . . . .
H11M H 0.585710 0.090957 0.863159 0.078 Uiso 1 1 calc GR . . . .
H11N H 0.548837 0.058748 0.870915 0.078 Uiso 1 1 calc GR . . . .
H11O H 0.547256 0.118452 0.834077 0.078 Uiso 1 1 calc GR . . . .
C12E C 0.64438(14) 0.1698(2) 0.4360(10) 0.0613(14) Uani 1 1 d . . . . .
H12M H 0.633232 0.201658 0.478714 0.092 Uiso 1 1 calc GR . . . .
H12N H 0.642557 0.166988 0.292961 0.092 Uiso 1 1 calc GR . . . .
H12O H 0.670080 0.169347 0.474831 0.092 Uiso 1 1 calc GR . . . .
OF O 0.48065(10) 0.23585(17) -0.0241(6) 0.0635(10) Uani 1 1 d . . . . .
HF H 0.488115 0.226063 0.085994 0.095 Uiso 1 1 calc GR . . . .
C1F C 0.44707(13) 0.2110(2) -0.0697(9) 0.0555(13) Uani 1 1 d . . . . .
H1F H 0.441633 0.215767 -0.212281 0.067 Uiso 1 1 calc R . . . .
C2F C 0.41682(17) 0.2363(3) 0.0519(12) 0.0764(18) Uani 1 1 d . . . . .
H2FA H 0.425064 0.240147 0.189372 0.092 Uiso 1 1 calc R . . . .
H2FB H 0.411729 0.270358 -0.001404 0.092 Uiso 1 1 calc R . . . .
C3F C 0.38362(17) 0.2059(3) 0.0468(12) 0.0768(18) Uani 1 1 d . . . . .
H3FA H 0.375990 0.201188 -0.091281 0.092 Uiso 1 1 calc R . . . .
H3FB H 0.363925 0.224332 0.115747 0.092 Uiso 1 1 calc R . . . .
C4F C 0.38888(14) 0.1532(2) 0.1445(9) 0.0599(14) Uani 1 1 d . . . . .
C5F C 0.42415(12) 0.1292(2) 0.0691(8) 0.0501(12) Uani 1 1 d . . . . .
C6F C 0.44922(13) 0.1556(2) -0.0263(8) 0.0505(12) Uani 1 1 d . . . . .
H6F H 0.470210 0.137991 -0.070679 0.061 Uiso 1 1 calc R . . . .
C7F C 0.35613(14) 0.1213(2) 0.0727(10) 0.0645(15) Uani 1 1 d . . . . .
H7FA H 0.333658 0.134533 0.134586 0.077 Uiso 1 1 calc R . . . .
H7FB H 0.353632 0.125729 -0.070912 0.077 Uiso 1 1 calc R . . . .
C8F C 0.35920(14) 0.0654(2) 0.1175(9) 0.0608(14) Uani 1 1 d . . . . .
H8FA H 0.338316 0.047159 0.058721 0.073 Uiso 1 1 calc R . . . .
H8FB H 0.358528 0.060041 0.261222 0.073 Uiso 1 1 calc R . . . .
C9F C 0.39454(13) 0.0447(2) 0.0350(9) 0.0574(13) Uani 1 1 d . . . . .
H9FA H 0.394033 0.047266 -0.109884 0.069 Uiso 1 1 calc R . . . .
H9FB H 0.396666 0.008445 0.069722 0.069 Uiso 1 1 calc R . . . .
C10F C 0.42786(13) 0.0731(2) 0.1134(8) 0.0530(12) Uani 1 1 d . . . . .
H10F H 0.427909 0.069226 0.259401 0.064 Uiso 1 1 calc R . . . .
C11F C 0.38908(17) 0.1558(3) 0.3685(10) 0.0711(17) Uani 1 1 d . . . . .
H11P H 0.409204 0.177382 0.412198 0.107 Uiso 1 1 calc GR . . . .
H11Q H 0.392235 0.121719 0.422209 0.107 Uiso 1 1 calc GR . . . .
H11R H 0.365943 0.169933 0.414606 0.107 Uiso 1 1 calc GR . . . .
C12F C 0.46295(14) 0.0493(2) 0.0364(10) 0.0618(14) Uani 1 1 d . . . . .
H12P H 0.464235 0.013918 0.078735 0.093 Uiso 1 1 calc GR . . . .
H12Q H 0.483964 0.067805 0.088385 0.093 Uiso 1 1 calc GR . . . .
H12R H 0.463182 0.050825 -0.107226 0.093 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
OA HA 0.8400 . ?
OA C1A 1.437(6) . ?
C1A H1A 1.0000 . ?
C1A C2A 1.500(8) . ?
C1A C6A 1.505(8) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.506(8) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.533(9) . ?
C4A C5A 1.527(7) . ?
C4A C7A 1.551(7) . ?
C4A C11A 1.534(9) . ?
C5A C6A 1.333(8) . ?
C5A C10A 1.517(8) . ?
C6A H6A 0.9500 . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.516(9) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.527(9) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.546(7) . ?
C10A H10A 1.0000 . ?
C10A C12A 1.522(8) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
OB HB 0.8400 . ?
OB C1B 1.431(6) . ?
C1B H1B 1.0000 . ?
C1B C2B 1.505(8) . ?
C1B C6B 1.504(7) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B C3B 1.535(8) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.539(7) . ?
C4B C5B 1.539(7) . ?
C4B C7B 1.546(8) . ?
C4B C11B 1.551(8) . ?
C5B C6B 1.335(8) . ?
C5B C10B 1.516(6) . ?
C6B H6B 0.9500 . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B C8B 1.535(8) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C9B 1.509(9) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9B C10B 1.547(8) . ?
C10B H10B 1.0000 . ?
C10B C12B 1.520(8) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
OC HC 0.8400 . ?
OC C1C 1.429(6) . ?
C1C H1C 1.0000 . ?
C1C C2C 1.523(8) . ?
C1C C6C 1.506(8) . ?
C2C H2CA 0.9900 . ?
C2C H2CB 0.9900 . ?
C2C C3C 1.530(7) . ?
C3C H3CA 0.9900 . ?
C3C H3CB 0.9900 . ?
C3C C4C 1.545(8) . ?
C4C C5C 1.515(7) . ?
C4C C7C 1.550(7) . ?
C4C C11C 1.536(8) . ?
C5C C6C 1.341(8) . ?
C5C C10C 1.523(8) . ?
C6C H6C 0.9500 . ?
C7C H7CA 0.9900 . ?
C7C H7CB 0.9900 . ?
C7C C8C 1.526(8) . ?
C8C H8CA 0.9900 . ?
C8C H8CB 0.9900 . ?
C8C C9C 1.526(8) . ?
C9C H9CA 0.9900 . ?
C9C H9CB 0.9900 . ?
C9C C10C 1.532(7) . ?
C10C H10C 1.0000 . ?
C10C C12C 1.530(7) . ?
C11C H11G 0.9800 . ?
C11C H11H 0.9800 . ?
C11C H11I 0.9800 . ?
C12C H12G 0.9800 . ?
C12C H12H 0.9800 . ?
C12C H12I 0.9800 . ?
OD HD 0.8400 . ?
OD C1D 1.440(6) . ?
C1D H1D 1.0000 . ?
C1D C2D 1.517(8) . ?
C1D C6D 1.501(8) . ?
C2D H2DA 0.9900 . ?
C2D H2DB 0.9900 . ?
C2D C3D 1.522(7) . ?
C3D H3DA 0.9900 . ?
C3D H3DB 0.9900 . ?
C3D C4D 1.539(7) . ?
C4D C5D 1.525(7) . ?
C4D C7D 1.548(6) . ?
C4D C11D 1.537(7) . ?
C5D C6D 1.335(7) . ?
C5D C10D 1.521(7) . ?
C6D H6D 0.9500 . ?
C7D H7DA 0.9900 . ?
C7D H7DB 0.9900 . ?
C7D C8D 1.525(8) . ?
C8D H8DA 0.9900 . ?
C8D H8DB 0.9900 . ?
C8D C9D 1.522(8) . ?
C9D H9DA 0.9900 . ?
C9D H9DB 0.9900 . ?
C9D C10D 1.537(7) . ?
C10D H10D 1.0000 . ?
C10D C12D 1.535(7) . ?
C11D H11J 0.9800 . ?
C11D H11K 0.9800 . ?
C11D H11L 0.9800 . ?
C12D H12J 0.9800 . ?
C12D H12K 0.9800 . ?
C12D H12L 0.9800 . ?
OE HE 0.8400 . ?
OE C1E 1.436(6) . ?
C1E H1E 1.0000 . ?
C1E C2E 1.510(8) . ?
C1E C6E 1.500(7) . ?
C2E H2EA 0.9900 . ?
C2E H2EB 0.9900 . ?
C2E C3E 1.529(7) . ?
C3E H3EA 0.9900 . ?
C3E H3EB 0.9900 . ?
C3E C4E 1.539(7) . ?
C4E C5E 1.544(7) . ?
C4E C7E 1.542(7) . ?
C4E C11E 1.538(8) . ?
C5E C6E 1.339(7) . ?
C5E C10E 1.522(7) . ?
C6E H6E 0.9500 . ?
C7E H7EA 0.9900 . ?
C7E H7EB 0.9900 . ?
C7E C8E 1.532(7) . ?
C8E H8EA 0.9900 . ?
C8E H8EB 0.9900 . ?
C8E C9E 1.516(8) . ?
C9E H9EA 0.9900 . ?
C9E H9EB 0.9900 . ?
C9E C10E 1.537(8) . ?
C10E H10E 1.0000 . ?
C10E C12E 1.534(7) . ?
C11E H11M 0.9800 . ?
C11E H11N 0.9800 . ?
C11E H11O 0.9800 . ?
C12E H12M 0.9800 . ?
C12E H12N 0.9800 . ?
C12E H12O 0.9800 . ?
OF HF 0.8400 . ?
OF C1F 1.431(6) . ?
C1F H1F 1.0000 . ?
C1F C2F 1.538(9) . ?
C1F C6F 1.498(8) . ?
C2F H2FA 0.9900 . ?
C2F H2FB 0.9900 . ?
C2F C3F 1.460(9) . ?
C3F H3FA 0.9900 . ?
C3F H3FB 0.9900 . ?
C3F C4F 1.557(9) . ?
C4F C5F 1.531(7) . ?
C4F C7F 1.548(8) . ?
C4F C11F 1.528(9) . ?
C5F C6F 1.326(7) . ?
C5F C10F 1.520(8) . ?
C6F H6F 0.9500 . ?
C7F H7FA 0.9900 . ?
C7F H7FB 0.9900 . ?
C7F C8F 1.516(9) . ?
C8F H8FA 0.9900 . ?
C8F H8FB 0.9900 . ?
C8F C9F 1.516(8) . ?
C9F H9FA 0.9900 . ?
C9F H9FB 0.9900 . ?
C9F C10F 1.532(7) . ?
C10F H10F 1.0000 . ?
C10F C12F 1.527(7) . ?
C11F H11P 0.9800 . ?
C11F H11Q 0.9800 . ?
C11F H11R 0.9800 . ?
C12F H12P 0.9800 . ?
C12F H12Q 0.9800 . ?
C12F H12R 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
C1A OA HA 109.5 . . ?
OA C1A H1A 108.0 . . ?
OA C1A C2A 109.9(5) . . ?
OA C1A C6A 111.4(4) . . ?
C2A C1A H1A 108.0 . . ?
C2A C1A C6A 111.4(5) . . ?
C6A C1A H1A 108.0 . . ?
C1A C2A H2AA 109.7 . . ?
C1A C2A H2AB 109.7 . . ?
C1A C2A C3A 109.7(5) . . ?
H2AA C2A H2AB 108.2 . . ?
C3A C2A H2AA 109.7 . . ?
C3A C2A H2AB 109.7 . . ?
C2A C3A H3AA 109.1 . . ?
C2A C3A H3AB 109.1 . . ?
C2A C3A C4A 112.6(5) . . ?
H3AA C3A H3AB 107.8 . . ?
C4A C3A H3AA 109.1 . . ?
C4A C3A H3AB 109.1 . . ?
C3A C4A C7A 106.4(5) . . ?
C3A C4A C11A 112.4(6) . . ?
C5A C4A C3A 109.8(5) . . ?
C5A C4A C7A 108.6(5) . . ?
C5A C4A C11A 110.1(5) . . ?
C11A C4A C7A 109.5(5) . . ?
C6A C5A C4A 121.5(5) . . ?
C6A C5A C10A 122.3(5) . . ?
C10A C5A C4A 116.2(5) . . ?
C1A C6A H6A 117.3 . . ?
C5A C6A C1A 125.3(5) . . ?
C5A C6A H6A 117.3 . . ?
C4A C7A H7AA 108.8 . . ?
C4A C7A H7AB 108.8 . . ?
H7AA C7A H7AB 107.7 . . ?
C8A C7A C4A 114.0(5) . . ?
C8A C7A H7AA 108.8 . . ?
C8A C7A H7AB 108.8 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A C9A 110.5(5) . . ?
H8AA C8A H8AB 108.1 . . ?
C9A C8A H8AA 109.5 . . ?
C9A C8A H8AB 109.5 . . ?
C8A C9A H9AA 109.4 . . ?
C8A C9A H9AB 109.4 . . ?
C8A C9A C10A 111.0(5) . . ?
H9AA C9A H9AB 108.0 . . ?
C10A C9A H9AA 109.4 . . ?
C10A C9A H9AB 109.4 . . ?
C5A C10A C9A 110.3(4) . . ?
C5A C10A H10A 106.7 . . ?
C5A C10A C12A 115.1(5) . . ?
C9A C10A H10A 106.7 . . ?
C12A C10A C9A 110.8(5) . . ?
C12A C10A H10A 106.7 . . ?
C4A C11A H11A 109.5 . . ?
C4A C11A H11B 109.5 . . ?
C4A C11A H11C 109.5 . . ?
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10A C12A H12A 109.5 . . ?
C10A C12A H12B 109.5 . . ?
C10A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C1B OB HB 109.5 . . ?
OB C1B H1B 107.6 . . ?
OB C1B C2B 112.0(4) . . ?
OB C1B C6B 110.6(4) . . ?
C2B C1B H1B 107.6 . . ?
C6B C1B H1B 107.6 . . ?
C6B C1B C2B 111.3(5) . . ?
C1B C2B H2BA 109.9 . . ?
C1B C2B H2BB 109.9 . . ?
C1B C2B C3B 108.9(5) . . ?
H2BA C2B H2BB 108.3 . . ?
C3B C2B H2BA 109.9 . . ?
C3B C2B H2BB 109.9 . . ?
C2B C3B H3BA 109.0 . . ?
C2B C3B H3BB 109.0 . . ?
C2B C3B C4B 112.8(5) . . ?
H3BA C3B H3BB 107.8 . . ?
C4B C3B H3BA 109.0 . . ?
C4B C3B H3BB 109.0 . . ?
C3B C4B C5B 110.2(4) . . ?
C3B C4B C7B 107.8(5) . . ?
C3B C4B C11B 109.6(5) . . ?
C5B C4B C7B 109.3(4) . . ?
C5B C4B C11B 109.5(5) . . ?
C7B C4B C11B 110.3(5) . . ?
C6B C5B C4B 121.9(4) . . ?
C6B C5B C10B 123.0(5) . . ?
C10B C5B C4B 115.1(4) . . ?
C1B C6B H6B 117.4 . . ?
C5B C6B C1B 125.3(5) . . ?
C5B C6B H6B 117.4 . . ?
C4B C7B H7BA 108.7 . . ?
C4B C7B H7BB 108.7 . . ?
H7BA C7B H7BB 107.6 . . ?
C8B C7B C4B 114.0(5) . . ?
C8B C7B H7BA 108.7 . . ?
C8B C7B H7BB 108.7 . . ?
C7B C8B H8BA 109.5 . . ?
C7B C8B H8BB 109.5 . . ?
H8BA C8B H8BB 108.1 . . ?
C9B C8B C7B 110.7(5) . . ?
C9B C8B H8BA 109.5 . . ?
C9B C8B H8BB 109.5 . . ?
C8B C9B H9BA 109.4 . . ?
C8B C9B H9BB 109.4 . . ?
C8B C9B C10B 111.2(5) . . ?
H9BA C9B H9BB 108.0 . . ?
C10B C9B H9BA 109.4 . . ?
C10B C9B H9BB 109.4 . . ?
C5B C10B C9B 109.5(5) . . ?
C5B C10B H10B 107.0 . . ?
C5B C10B C12B 114.7(4) . . ?
C9B C10B H10B 107.0 . . ?
C12B C10B C9B 111.3(5) . . ?
C12B C10B H10B 107.0 . . ?
C4B C11B H11D 109.5 . . ?
C4B C11B H11E 109.5 . . ?
C4B C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10B C12B H12D 109.5 . . ?
C10B C12B H12E 109.5 . . ?
C10B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C1C OC HC 109.5 . . ?
OC C1C H1C 107.9 . . ?
OC C1C C2C 112.0(5) . . ?
OC C1C C6C 110.7(4) . . ?
C2C C1C H1C 107.9 . . ?
C6C C1C H1C 107.9 . . ?
C6C C1C C2C 110.1(5) . . ?
C1C C2C H2CA 110.1 . . ?
C1C C2C H2CB 110.1 . . ?
C1C C2C C3C 107.9(4) . . ?
H2CA C2C H2CB 108.4 . . ?
C3C C2C H2CA 110.1 . . ?
C3C C2C H2CB 110.1 . . ?
C2C C3C H3CA 109.1 . . ?
C2C C3C H3CB 109.1 . . ?
C2C C3C C4C 112.6(4) . . ?
H3CA C3C H3CB 107.8 . . ?
C4C C3C H3CA 109.1 . . ?
C4C C3C H3CB 109.1 . . ?
C3C C4C C7C 107.8(4) . . ?
C5C C4C C3C 111.2(4) . . ?
C5C C4C C7C 109.0(5) . . ?
C5C C4C C11C 110.4(4) . . ?
C11C C4C C3C 108.6(5) . . ?
C11C C4C C7C 109.9(4) . . ?
C4C C5C C10C 115.0(4) . . ?
C6C C5C C4C 121.5(5) . . ?
C6C C5C C10C 123.4(5) . . ?
C1C C6C H6C 117.2 . . ?
C5C C6C C1C 125.6(5) . . ?
C5C C6C H6C 117.2 . . ?
C4C C7C H7CA 108.9 . . ?
C4C C7C H7CB 108.9 . . ?
H7CA C7C H7CB 107.7 . . ?
C8C C7C C4C 113.3(4) . . ?
C8C C7C H7CA 108.9 . . ?
C8C C7C H7CB 108.9 . . ?
C7C C8C H8CA 109.7 . . ?
C7C C8C H8CB 109.7 . . ?
H8CA C8C H8CB 108.2 . . ?
C9C C8C C7C 109.7(5) . . ?
C9C C8C H8CA 109.7 . . ?
C9C C8C H8CB 109.7 . . ?
C8C C9C H9CA 109.3 . . ?
C8C C9C H9CB 109.3 . . ?
C8C C9C C10C 111.8(5) . . ?
H9CA C9C H9CB 107.9 . . ?
C10C C9C H9CA 109.3 . . ?
C10C C9C H9CB 109.3 . . ?
C5C C10C C9C 109.7(4) . . ?
C5C C10C H10C 107.0 . . ?
C5C C10C C12C 115.1(5) . . ?
C9C C10C H10C 107.0 . . ?
C12C C10C C9C 110.6(5) . . ?
C12C C10C H10C 107.0 . . ?
C4C C11C H11G 109.5 . . ?
C4C C11C H11H 109.5 . . ?
C4C C11C H11I 109.5 . . ?
H11G C11C H11H 109.5 . . ?
H11G C11C H11I 109.5 . . ?
H11H C11C H11I 109.5 . . ?
C10C C12C H12G 109.5 . . ?
C10C C12C H12H 109.5 . . ?
C10C C12C H12I 109.5 . . ?
H12G C12C H12H 109.5 . . ?
H12G C12C H12I 109.5 . . ?
H12H C12C H12I 109.5 . . ?
C1D OD HD 109.5 . . ?
OD C1D H1D 107.5 . . ?
OD C1D C2D 112.2(4) . . ?
OD C1D C6D 110.6(4) . . ?
C2D C1D H1D 107.5 . . ?
C6D C1D H1D 107.5 . . ?
C6D C1D C2D 111.2(5) . . ?
C1D C2D H2DA 110.0 . . ?
C1D C2D H2DB 110.0 . . ?
C1D C2D C3D 108.3(4) . . ?
H2DA C2D H2DB 108.4 . . ?
C3D C2D H2DA 110.0 . . ?
C3D C2D H2DB 110.0 . . ?
C2D C3D H3DA 108.9 . . ?
C2D C3D H3DB 108.9 . . ?
C2D C3D C4D 113.3(4) . . ?
H3DA C3D H3DB 107.7 . . ?
C4D C3D H3DA 108.9 . . ?
C4D C3D H3DB 108.9 . . ?
C3D C4D C7D 108.0(4) . . ?
C5D C4D C3D 110.2(4) . . ?
C5D C4D C7D 109.4(4) . . ?
C5D C4D C11D 110.2(4) . . ?
C11D C4D C3D 109.2(4) . . ?
C11D C4D C7D 109.8(4) . . ?
C6D C5D C4D 122.3(5) . . ?
C6D C5D C10D 122.8(5) . . ?
C10D C5D C4D 114.9(4) . . ?
C1D C6D H6D 117.6 . . ?
C5D C6D C1D 124.9(5) . . ?
C5D C6D H6D 117.6 . . ?
C4D C7D H7DA 108.7 . . ?
C4D C7D H7DB 108.7 . . ?
H7DA C7D H7DB 107.6 . . ?
C8D C7D C4D 114.4(4) . . ?
C8D C7D H7DA 108.7 . . ?
C8D C7D H7DB 108.7 . . ?
C7D C8D H8DA 109.7 . . ?
C7D C8D H8DB 109.7 . . ?
H8DA C8D H8DB 108.2 . . ?
C9D C8D C7D 109.8(4) . . ?
C9D C8D H8DA 109.7 . . ?
C9D C8D H8DB 109.7 . . ?
C8D C9D H9DA 109.4 . . ?
C8D C9D H9DB 109.4 . . ?
C8D C9D C10D 111.3(4) . . ?
H9DA C9D H9DB 108.0 . . ?
C10D C9D H9DA 109.4 . . ?
C10D C9D H9DB 109.4 . . ?
C5D C10D C9D 109.2(4) . . ?
C5D C10D H10D 107.1 . . ?
C5D C10D C12D 114.6(5) . . ?
C9D C10D H10D 107.1 . . ?
C12D C10D C9D 111.4(5) . . ?
C12D C10D H10D 107.1 . . ?
C4D C11D H11J 109.5 . . ?
C4D C11D H11K 109.5 . . ?
C4D C11D H11L 109.5 . . ?
H11J C11D H11K 109.5 . . ?
H11J C11D H11L 109.5 . . ?
H11K C11D H11L 109.5 . . ?
C10D C12D H12J 109.5 . . ?
C10D C12D H12K 109.5 . . ?
C10D C12D H12L 109.5 . . ?
H12J C12D H12K 109.5 . . ?
H12J C12D H12L 109.5 . . ?
H12K C12D H12L 109.5 . . ?
C1E OE HE 109.5 . . ?
OE C1E H1E 107.6 . . ?
OE C1E C2E 111.5(4) . . ?
OE C1E C6E 110.6(4) . . ?
C2E C1E H1E 107.6 . . ?
C6E C1E H1E 107.6 . . ?
C6E C1E C2E 111.8(4) . . ?
C1E C2E H2EA 109.9 . . ?
C1E C2E H2EB 109.9 . . ?
C1E C2E C3E 108.7(4) . . ?
H2EA C2E H2EB 108.3 . . ?
C3E C2E H2EA 109.9 . . ?
C3E C2E H2EB 109.9 . . ?
C2E C3E H3EA 108.9 . . ?
C2E C3E H3EB 108.9 . . ?
C2E C3E C4E 113.3(4) . . ?
H3EA C3E H3EB 107.7 . . ?
C4E C3E H3EA 108.9 . . ?
C4E C3E H3EB 108.9 . . ?
C3E C4E C5E 110.1(4) . . ?
C3E C4E C7E 107.9(4) . . ?
C7E C4E C5E 109.3(4) . . ?
C11E C4E C3E 109.2(4) . . ?
C11E C4E C5E 109.2(5) . . ?
C11E C4E C7E 111.0(4) . . ?
C6E C5E C4E 121.9(4) . . ?
C6E C5E C10E 123.4(5) . . ?
C10E C5E C4E 114.7(4) . . ?
C1E C6E H6E 117.5 . . ?
C5E C6E C1E 125.0(5) . . ?
C5E C6E H6E 117.5 . . ?
C4E C7E H7EA 108.8 . . ?
C4E C7E H7EB 108.8 . . ?
H7EA C7E H7EB 107.7 . . ?
C8E C7E C4E 113.8(4) . . ?
C8E C7E H7EA 108.8 . . ?
C8E C7E H7EB 108.8 . . ?
C7E C8E H8EA 109.6 . . ?
C7E C8E H8EB 109.6 . . ?
H8EA C8E H8EB 108.1 . . ?
C9E C8E C7E 110.2(4) . . ?
C9E C8E H8EA 109.6 . . ?
C9E C8E H8EB 109.6 . . ?
C8E C9E H9EA 109.5 . . ?
C8E C9E H9EB 109.5 . . ?
C8E C9E C10E 110.6(4) . . ?
H9EA C9E H9EB 108.1 . . ?
C10E C9E H9EA 109.5 . . ?
C10E C9E H9EB 109.5 . . ?
C5E C10E C9E 109.9(5) . . ?
C5E C10E H10E 107.1 . . ?
C5E C10E C12E 114.5(4) . . ?
C9E C10E H10E 107.1 . . ?
C12E C10E C9E 110.7(4) . . ?
C12E C10E H10E 107.1 . . ?
C4E C11E H11M 109.5 . . ?
C4E C11E H11N 109.5 . . ?
C4E C11E H11O 109.5 . . ?
H11M C11E H11N 109.5 . . ?
H11M C11E H11O 109.5 . . ?
H11N C11E H11O 109.5 . . ?
C10E C12E H12M 109.5 . . ?
C10E C12E H12N 109.5 . . ?
C10E C12E H12O 109.5 . . ?
H12M C12E H12N 109.5 . . ?
H12M C12E H12O 109.5 . . ?
H12N C12E H12O 109.5 . . ?
C1F OF HF 109.5 . . ?
OF C1F H1F 109.0 . . ?
OF C1F C2F 107.8(5) . . ?
OF C1F C6F 111.2(4) . . ?
C2F C1F H1F 109.0 . . ?
C6F C1F H1F 109.0 . . ?
C6F C1F C2F 110.9(5) . . ?
C1F C2F H2FA 109.5 . . ?
C1F C2F H2FB 109.5 . . ?
H2FA C2F H2FB 108.1 . . ?
C3F C2F C1F 110.6(6) . . ?
C3F C2F H2FA 109.5 . . ?
C3F C2F H2FB 109.5 . . ?
C2F C3F H3FA 109.2 . . ?
C2F C3F H3FB 109.2 . . ?
C2F C3F C4F 112.2(5) . . ?
H3FA C3F H3FB 107.9 . . ?
C4F C3F H3FA 109.2 . . ?
C4F C3F H3FB 109.2 . . ?
C5F C4F C3F 109.5(5) . . ?
C5F C4F C7F 108.9(5) . . ?
C7F C4F C3F 104.9(5) . . ?
C11F C4F C3F 112.8(6) . . ?
C11F C4F C5F 110.5(5) . . ?
C11F C4F C7F 110.1(5) . . ?
C6F C5F C4F 122.2(5) . . ?
C6F C5F C10F 123.4(5) . . ?
C10F C5F C4F 114.5(4) . . ?
C1F C6F H6F 117.4 . . ?
C5F C6F C1F 125.2(5) . . ?
C5F C6F H6F 117.4 . . ?
C4F C7F H7FA 108.7 . . ?
C4F C7F H7FB 108.7 . . ?
H7FA C7F H7FB 107.6 . . ?
C8F C7F C4F 114.3(5) . . ?
C8F C7F H7FA 108.7 . . ?
C8F C7F H7FB 108.7 . . ?
C7F C8F H8FA 109.7 . . ?
C7F C8F H8FB 109.7 . . ?
C7F C8F C9F 110.0(5) . . ?
H8FA C8F H8FB 108.2 . . ?
C9F C8F H8FA 109.7 . . ?
C9F C8F H8FB 109.7 . . ?
C8F C9F H9FA 109.2 . . ?
C8F C9F H9FB 109.2 . . ?
C8F C9F C10F 112.1(5) . . ?
H9FA C9F H9FB 107.9 . . ?
C10F C9F H9FA 109.2 . . ?
C10F C9F H9FB 109.2 . . ?
C5F C10F C9F 109.8(4) . . ?
C5F C10F H10F 107.3 . . ?
C5F C10F C12F 114.2(5) . . ?
C9F C10F H10F 107.3 . . ?
C12F C10F C9F 110.5(5) . . ?
C12F C10F H10F 107.3 . . ?
C4F C11F H11P 109.5 . . ?
C4F C11F H11Q 109.5 . . ?
C4F C11F H11R 109.5 . . ?
H11P C11F H11Q 109.5 . . ?
H11P C11F H11R 109.5 . . ?
H11Q C11F H11R 109.5 . . ?
C10F C12F H12P 109.5 . . ?
C10F C12F H12Q 109.5 . . ?
C10F C12F H12R 109.5 . . ?
H12P C12F H12Q 109.5 . . ?
H12P C12F H12R 109.5 . . ?
H12Q C12F H12R 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
OA HA OB 0.84 1.89 2.724(5) 171.1 . yes
OB HB OC 0.84 1.84 2.682(5) 176.2 1_554 yes
OC HC OA 0.84 1.83 2.665(6) 169.2 . yes
OD HD OF 0.84 1.86 2.692(6) 168.2 . yes
OE HE OD 0.84 1.86 2.694(5) 169.2 1_556 yes
OF HF OE 0.84 1.91 2.742(5) 170.7 . yes

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
OA C1A C2A C3A -169.5(5) . . . . ?
OA C1A C6A C5A 138.2(5) . . . . ?
C1A C2A C3A C4A 64.2(7) . . . . ?
C2A C1A C6A C5A 15.1(7) . . . . ?
C2A C3A C4A C5A -46.8(7) . . . . ?
C2A C3A C4A C7A -164.1(6) . . . . ?
C2A C3A C4A C11A 76.1(6) . . . . ?
C3A C4A C5A C6A 14.7(7) . . . . ?
C3A C4A C5A C10A -166.0(5) . . . . ?
C3A C4A C7A C8A 169.5(5) . . . . ?
C4A C5A C6A C1A 0.7(8) . . . . ?
C4A C5A C10A C9A 52.9(6) . . . . ?
C4A C5A C10A C12A 179.2(5) . . . . ?
C4A C7A C8A C9A -56.8(7) . . . . ?
C5A C4A C7A C8A 51.4(7) . . . . ?
C6A C1A C2A C3A -45.5(7) . . . . ?
C6A C5A C10A C9A -127.9(5) . . . . ?
C6A C5A C10A C12A -1.6(8) . . . . ?
C7A C4A C5A C6A 130.6(5) . . . . ?
C7A C4A C5A C10A -50.1(6) . . . . ?
C7A C8A C9A C10A 57.1(7) . . . . ?
C8A C9A C10A C5A -54.5(7) . . . . ?
C8A C9A C10A C12A 176.9(5) . . . . ?
C10A C5A C6A C1A -178.5(5) . . . . ?
C11A C4A C5A C6A -109.5(6) . . . . ?
C11A C4A C5A C10A 69.7(6) . . . . ?
C11A C4A C7A C8A -68.8(7) . . . . ?
OB C1B C2B C3B -172.6(4) . . . . ?
OB C1B C6B C5B 142.3(6) . . . . ?
C1B C2B C3B C4B 63.8(7) . . . . ?
C2B C1B C6B C5B 17.2(8) . . . . ?
C2B C3B C4B C5B -42.6(7) . . . . ?
C2B C3B C4B C7B -161.9(5) . . . . ?
C2B C3B C4B C11B 78.0(6) . . . . ?
C3B C4B C5B C6B 9.7(7) . . . . ?
C3B C4B C5B C10B -169.1(5) . . . . ?
C3B C4B C7B C8B 169.3(5) . . . . ?
C4B C5B C6B C1B 3.1(9) . . . . ?
C4B C5B C10B C9B 55.1(6) . . . . ?
C4B C5B C10B C12B -179.0(5) . . . . ?
C4B C7B C8B C9B -54.5(7) . . . . ?
C5B C4B C7B C8B 49.5(7) . . . . ?
C6B C1B C2B C3B -48.3(6) . . . . ?
C6B C5B C10B C9B -123.7(6) . . . . ?
C6B C5B C10B C12B 2.2(8) . . . . ?
C7B C4B C5B C6B 128.0(6) . . . . ?
C7B C4B C5B C10B -50.8(6) . . . . ?
C7B C8B C9B C10B 57.5(7) . . . . ?
C8B C9B C10B C5B -57.5(6) . . . . ?
C8B C9B C10B C12B 174.7(5) . . . . ?
C10B C5B C6B C1B -178.2(5) . . . . ?
C11B C4B C5B C6B -111.0(6) . . . . ?
C11B C4B C5B C10B 70.2(6) . . . . ?
C11B C4B C7B C8B -71.0(7) . . . . ?
OC C1C C2C C3C -174.7(4) . . . . ?
OC C1C C6C C5C 145.4(5) . . . . ?
C1C C2C C3C C4C 64.5(6) . . . . ?
C2C C1C C6C C5C 20.9(7) . . . . ?
C2C C3C C4C C5C -42.3(6) . . . . ?
C2C C3C C4C C7C -161.7(5) . . . . ?
C2C C3C C4C C11C 79.3(5) . . . . ?
C3C C4C C5C C6C 9.5(7) . . . . ?
C3C C4C C5C C10C -171.2(4) . . . . ?
C3C C4C C7C C8C 173.7(5) . . . . ?
C4C C5C C6C C1C 0.9(8) . . . . ?
C4C C5C C10C C9C 54.6(6) . . . . ?
C4C C5C C10C C12C -179.9(5) . . . . ?
C4C C7C C8C C9C -56.2(6) . . . . ?
C5C C4C C7C C8C 52.9(6) . . . . ?
C6C C1C C2C C3C -51.0(6) . . . . ?
C6C C5C C10C C9C -126.1(5) . . . . ?
C6C C5C C10C C12C -0.6(8) . . . . ?
C7C C4C C5C C6C 128.2(5) . . . . ?
C7C C4C C5C C10C -52.4(6) . . . . ?
C7C C8C C9C C10C 57.3(6) . . . . ?
C8C C9C C10C C5C -55.8(6) . . . . ?
C8C C9C C10C C12C 176.1(5) . . . . ?
C10C C5C C6C C1C -178.4(5) . . . . ?
C11C C4C C5C C6C -111.0(6) . . . . ?
C11C C4C C5C C10C 68.3(6) . . . . ?
C11C C4C C7C C8C -68.1(6) . . . . ?
OD C1D C2D C3D -173.5(4) . . . . ?
OD C1D C6D C5D 144.7(5) . . . . ?
C1D C2D C3D C4D 63.6(6) . . . . ?
C2D C1D C6D C5D 19.3(7) . . . . ?
C2D C3D C4D C5D -42.9(6) . . . . ?
C2D C3D C4D C7D -162.3(4) . . . . ?
C2D C3D C4D C11D 78.4(5) . . . . ?
C3D C4D C5D C6D 10.5(6) . . . . ?
C3D C4D C5D C10D -169.4(4) . . . . ?
C3D C4D C7D C8D 169.9(5) . . . . ?
C4D C5D C6D C1D 0.8(8) . . . . ?
C4D C5D C10D C9D 55.6(6) . . . . ?
C4D C5D C10D C12D -178.6(4) . . . . ?
C4D C7D C8D C9D -54.6(6) . . . . ?
C5D C4D C7D C8D 50.0(6) . . . . ?
C6D C1D C2D C3D -49.0(6) . . . . ?
C6D C5D C10D C9D -124.3(5) . . . . ?
C6D C5D C10D C12D 1.5(7) . . . . ?
C7D C4D C5D C6D 129.1(5) . . . . ?
C7D C4D C5D C10D -50.8(5) . . . . ?
C7D C8D C9D C10D 58.1(6) . . . . ?
C8D C9D C10D C5D -58.3(6) . . . . ?
C8D C9D C10D C12D 174.2(5) . . . . ?
C10D C5D C6D C1D -179.3(5) . . . . ?
C11D C4D C5D C6D -110.1(5) . . . . ?
C11D C4D C5D C10D 70.1(5) . . . . ?
C11D C4D C7D C8D -71.1(6) . . . . ?
OE C1E C2E C3E -172.3(4) . . . . ?
OE C1E C6E C5E 142.1(5) . . . . ?
C1E C2E C3E C4E 63.3(6) . . . . ?
C2E C1E C6E C5E 17.2(8) . . . . ?
C2E C3E C4E C5E -42.6(6) . . . . ?
C2E C3E C4E C7E -161.9(5) . . . . ?
C2E C3E C4E C11E 77.3(6) . . . . ?
C3E C4E C5E C6E 9.7(7) . . . . ?
C3E C4E C5E C10E -168.6(5) . . . . ?
C3E C4E C7E C8E 170.2(5) . . . . ?
C4E C5E C6E C1E 2.9(8) . . . . ?
C4E C5E C10E C9E 54.7(6) . . . . ?
C4E C5E C10E C12E 180.0(5) . . . . ?
C4E C7E C8E C9E -56.2(6) . . . . ?
C5E C4E C7E C8E 50.4(6) . . . . ?
C6E C1E C2E C3E -47.9(6) . . . . ?
C6E C5E C10E C9E -123.6(6) . . . . ?
C6E C5E C10E C12E 1.7(8) . . . . ?
C7E C4E C5E C6E 128.1(5) . . . . ?
C7E C4E C5E C10E -50.2(6) . . . . ?
C7E C8E C9E C10E 58.9(6) . . . . ?
C8E C9E C10E C5E -58.0(6) . . . . ?
C8E C9E C10E C12E 174.5(5) . . . . ?
C10E C5E C6E C1E -179.0(5) . . . . ?
C11E C4E C5E C6E -110.3(6) . . . . ?
C11E C4E C5E C10E 71.5(6) . . . . ?
C11E C4E C7E C8E -70.2(6) . . . . ?
OF C1F C2F C3F -167.2(6) . . . . ?
OF C1F C6F C5F 133.6(5) . . . . ?
C1F C2F C3F C4F 63.9(8) . . . . ?
C2F C1F C6F C5F 13.7(8) . . . . ?
C2F C3F C4F C5F -46.9(8) . . . . ?
C2F C3F C4F C7F -163.6(6) . . . . ?
C2F C3F C4F C11F 76.5(7) . . . . ?
C3F C4F C5F C6F 14.4(8) . . . . ?
C3F C4F C5F C10F -165.8(5) . . . . ?
C3F C4F C7F C8F 168.8(5) . . . . ?
C4F C5F C6F C1F 1.1(9) . . . . ?
C4F C5F C10F C9F 54.8(6) . . . . ?
C4F C5F C10F C12F 179.5(5) . . . . ?
C4F C7F C8F C9F -55.0(7) . . . . ?
C5F C4F C7F C8F 51.7(7) . . . . ?
C6F C1F C2F C3F -45.3(7) . . . . ?
C6F C5F C10F C9F -125.4(6) . . . . ?
C6F C5F C10F C12F -0.7(8) . . . . ?
C7F C4F C5F C6F 128.5(6) . . . . ?
C7F C4F C5F C10F -51.7(6) . . . . ?
C7F C8F C9F C10F 56.7(7) . . . . ?
C8F C9F C10F C5F -56.4(6) . . . . ?
C8F C9F C10F C12F 176.8(5) . . . . ?
C10F C5F C6F C1F -178.7(5) . . . . ?
C11F C4F C5F C6F -110.4(6) . . . . ?
C11F C4F C5F C10F 69.3(6) . . . . ?
C11F C4F C7F C8F -69.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#END---------------------------------------------------------------------------
