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

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

data_ada2oh150K
_database_code_depnum_ccdc_archive 'CCDC 2129547'
loop_
_audit_author_name
_audit_author_address
'Ph. Negrier'
;Universite de Bordeaux
France
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 O'
_chemical_formula_sum            'C10 H16 O'
_chemical_formula_weight         152.23

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.4076(4)
_cell_length_b                   11.4418(5)
_cell_length_c                   11.4575(4)
_cell_angle_alpha                82.116(3)
_cell_angle_beta                 70.323(3)
_cell_angle_gamma                62.123(4)
_cell_volume                     1244.37(9)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14621
_cell_measurement_theta_min      4.0410
_cell_measurement_theta_max      75.6160

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.585
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.45590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_detector                 PILT
_diffrn_measurement_device       'AFC11 (Right): Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku PILATUS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            16978
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.099
_diffrn_reflns_theta_max         72.112
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4832
_reflns_number_gt                4420
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    'Superflip 03/15/13 12:43'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0773P)²+0.3081P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.0241(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4832
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1334
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O10 O 0.65150(9) 0.10906(8) 0.37072(8) 0.0348(2) Uani 1 1 d . . . . .
H10 H 0.661(3) 0.027(3) 0.346(2) 0.111(9) Uiso 1 1 d . . . . .
C1 C 0.55180(11) 0.21907(10) 0.32387(10) 0.0245(2) Uani 1 1 d . . . . .
H1 H 0.4648 0.2086 0.3446 0.029 Uiso 1 1 calc R U . . .
C2 C 0.51696(11) 0.34640(10) 0.38563(10) 0.0255(3) Uani 1 1 d . . . . .
H2 H 0.4800 0.3411 0.4776 0.031 Uiso 1 1 calc R U . . .
C3 C 0.64809(12) 0.36643(11) 0.35223(11) 0.0294(3) Uani 1 1 d . . . . .
H3A H 0.7201 0.2917 0.3825 0.035 Uiso 1 1 calc R U . . .
H3B H 0.6253 0.4490 0.3924 0.035 Uiso 1 1 calc R U . . .
C4 C 0.70414(12) 0.37460(12) 0.21132(11) 0.0304(3) Uani 1 1 d . . . . .
H4 H 0.7898 0.3876 0.1894 0.037 Uiso 1 1 calc R U . . .
C5 C 0.74069(12) 0.24579(12) 0.15041(11) 0.0306(3) Uani 1 1 d . . . . .
H5A H 0.8131 0.1704 0.1797 0.037 Uiso 1 1 calc R U . . .
H5B H 0.7784 0.2498 0.0593 0.037 Uiso 1 1 calc R U . . .
C6 C 0.60973(11) 0.22551(11) 0.18350(10) 0.0249(2) Uani 1 1 d . . . . .
H6 H 0.6336 0.1414 0.1437 0.030 Uiso 1 1 calc R U . . .
C7 C 0.40569(12) 0.46274(11) 0.33882(11) 0.0308(3) Uani 1 1 d . . . . .
H7A H 0.3207 0.4502 0.3606 0.037 Uiso 1 1 calc R U . . .
H7B H 0.3804 0.5461 0.3791 0.037 Uiso 1 1 calc R U . . .
C8 C 0.46189(12) 0.47128(11) 0.19827(11) 0.0296(3) Uani 1 1 d . . . . .
H8 H 0.3893 0.5475 0.1681 0.036 Uiso 1 1 calc R U . . .
C9 C 0.49820(12) 0.34249(12) 0.13722(11) 0.0286(3) Uani 1 1 d . . . . .
H9A H 0.5337 0.3474 0.0460 0.034 Uiso 1 1 calc R U . . .
H9B H 0.4135 0.3297 0.1581 0.034 Uiso 1 1 calc R U . . .
C10 C 0.59301(14) 0.49116(12) 0.16531(11) 0.0340(3) Uani 1 1 d . . . . .
H10A H 0.6294 0.4976 0.0743 0.041 Uiso 1 1 calc R U . . .
H10B H 0.5697 0.5745 0.2043 0.041 Uiso 1 1 calc R U . . .
O20 O 0.66869(9) 0.88408(8) 0.30618(9) 0.0349(2) Uani 1 1 d . . . . .
H20 H 0.581(3) 0.886(3) 0.330(2) 0.110(8) Uiso 1 1 d . . . . .
C11 C 0.76653(11) 0.76651(10) 0.34693(10) 0.0243(2) Uani 1 1 d . . . . .
H11 H 0.7290 0.7608 0.4388 0.029 Uiso 1 1 calc R U . . .
C12 C 0.79095(11) 0.64357(10) 0.28470(10) 0.0239(2) Uani 1 1 d . . . . .
H12 H 0.7005 0.6396 0.3050 0.029 Uiso 1 1 calc R U . . .
C13 C 0.85172(12) 0.64922(11) 0.14400(11) 0.0290(3) Uani 1 1 d . . . . .
H13A H 0.7851 0.7282 0.1122 0.035 Uiso 1 1 calc R U . . .
H13B H 0.8675 0.5697 0.1037 0.035 Uiso 1 1 calc R U . . .
C14 C 0.99016(12) 0.65578(12) 0.11314(10) 0.0299(3) Uani 1 1 d . . . . .
H14 H 1.0300 0.6594 0.0213 0.036 Uiso 1 1 calc R U . . .
C15 C 0.96436(12) 0.78005(11) 0.17503(11) 0.0293(3) Uani 1 1 d . . . . .
H15A H 1.0532 0.7853 0.1547 0.035 Uiso 1 1 calc R U . . .
H15B H 0.8986 0.8599 0.1434 0.035 Uiso 1 1 calc R U . . .
C16 C 0.90359(11) 0.77451(10) 0.31555(10) 0.0245(2) Uani 1 1 d . . . . .
H16 H 0.8866 0.8555 0.3559 0.029 Uiso 1 1 calc R U . . .
C17 C 0.89388(12) 0.52055(11) 0.33359(10) 0.0268(3) Uani 1 1 d . . . . .
H17A H 0.8546 0.5166 0.4245 0.032 Uiso 1 1 calc R U . . .
H17B H 0.9097 0.4398 0.2952 0.032 Uiso 1 1 calc R U . . .
C18 C 1.03236(11) 0.52687(10) 0.30222(10) 0.0272(3) Uani 1 1 d . . . . .
H18 H 1.0997 0.4465 0.3337 0.033 Uiso 1 1 calc R U . . .
C19 C 1.00632(12) 0.65107(11) 0.36415(11) 0.0276(3) Uani 1 1 d . . . . .
H19A H 1.0955 0.6553 0.3457 0.033 Uiso 1 1 calc R U . . .
H19B H 0.9675 0.6474 0.4552 0.033 Uiso 1 1 calc R U . . .
C20 C 1.09264(12) 0.53272(12) 0.16177(11) 0.0326(3) Uani 1 1 d . . . . .
H20A H 1.1100 0.4524 0.1216 0.039 Uiso 1 1 calc R U . . .
H20B H 1.1827 0.5358 0.1412 0.039 Uiso 1 1 calc R U . . .
O30 O 0.41493(8) 0.89389(9) 0.38175(8) 0.0341(2) Uani 1 1 d . . . . .
H30 H 0.386(2) 0.894(2) 0.472(2) 0.100(8) Uiso 1 1 d . . . . .
C21 C 0.31256(11) 1.00845(11) 0.34202(10) 0.0255(2) Uani 1 1 d . . . . .
H21 H 0.2943 1.0888 0.3845 0.031 Uiso 1 1 calc R U . . .
C22 C 0.36893(11) 1.02037(11) 0.20265(10) 0.0271(3) Uani 1 1 d . . . . .
H22 H 0.4585 1.0261 0.1820 0.033 Uiso 1 1 calc R U . . .
C23 C 0.39440(12) 0.89977(12) 0.13545(11) 0.0318(3) Uani 1 1 d . . . . .
H23A H 0.4644 0.8183 0.1612 0.038 Uiso 1 1 calc R U . . .
H23B H 0.4312 0.9078 0.0448 0.038 Uiso 1 1 calc R U . . .
C24 C 0.25691(12) 0.89121(12) 0.16734(12) 0.0330(3) Uani 1 1 d . . . . .
H24 H 0.2734 0.8124 0.1237 0.040 Uiso 1 1 calc R U . . .
C25 C 0.20168(12) 0.87776(11) 0.30742(12) 0.0328(3) Uani 1 1 d . . . . .
H25A H 0.2703 0.7963 0.3345 0.039 Uiso 1 1 calc R U . . .
H25B H 0.1135 0.8711 0.3285 0.039 Uiso 1 1 calc R U . . .
C26 C 0.17611(11) 0.99845(11) 0.37451(10) 0.0268(3) Uani 1 1 d . . . . .
H26 H 0.1401 0.9896 0.4661 0.032 Uiso 1 1 calc R U . . .
C27 C 0.26129(14) 1.14640(12) 0.16176(12) 0.0354(3) Uani 1 1 d . . . . .
H27A H 0.2449 1.2245 0.2048 0.043 Uiso 1 1 calc R U . . .
H27B H 0.2971 1.1568 0.0714 0.043 Uiso 1 1 calc R U . . .
C28 C 0.12426(12) 1.13757(12) 0.19286(12) 0.0335(3) Uani 1 1 d . . . . .
H28 H 0.0544 1.2195 0.1657 0.040 Uiso 1 1 calc R U . . .
C29 C 0.06891(12) 1.12431(12) 0.33279(12) 0.0328(3) Uani 1 1 d . . . . .
H29A H -0.0205 1.1198 0.3541 0.039 Uiso 1 1 calc R U . . .
H29B H 0.0516 1.2026 0.3763 0.039 Uiso 1 1 calc R U . . .
C30 C 0.15042(13) 1.01679(13) 0.12540(13) 0.0382(3) Uani 1 1 d . . . . .
H30A H 0.0619 1.0113 0.1442 0.046 Uiso 1 1 calc R U . . .
H30B H 0.1862 1.0255 0.0347 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O10 C1 1.4328(12) . ?
C1 C6 1.5251(15) . ?
C1 C2 1.5275(14) . ?
C2 C3 1.5323(16) . ?
C2 C7 1.5340(14) . ?
C3 C4 1.5308(16) . ?
C4 C10 1.5296(16) . ?
C4 C5 1.5312(16) . ?
C5 C6 1.5322(15) . ?
C6 C9 1.5358(14) . ?
C7 C8 1.5277(16) . ?
C8 C10 1.5317(16) . ?
C8 C9 1.5328(16) . ?
O20 C11 1.4310(12) . ?
C11 C16 1.5259(14) . ?
C11 C12 1.5296(14) . ?
C12 C13 1.5311(15) . ?
C12 C17 1.5346(14) . ?
C13 C14 1.5336(16) . ?
C14 C20 1.5310(16) . ?
C14 C15 1.5349(16) . ?
C15 C16 1.5291(15) . ?
C16 C19 1.5343(14) . ?
C17 C18 1.5320(15) . ?
C18 C20 1.5282(16) . ?
C18 C19 1.5334(15) . ?
O30 C21 1.4325(13) . ?
C21 C22 1.5208(15) . ?
C21 C26 1.5293(15) . ?
C22 C23 1.5321(16) . ?
C22 C27 1.5339(15) . ?
C23 C24 1.5333(17) . ?
C24 C25 1.5292(17) . ?
C24 C30 1.5305(16) . ?
C25 C26 1.5318(16) . ?
C26 C29 1.5348(15) . ?
C27 C28 1.5308(17) . ?
C28 C29 1.5275(17) . ?
C28 C30 1.5323(17) . ?

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
O10 C1 C6 110.56(8) . . ?
O10 C1 C2 109.01(9) . . ?
C6 C1 C2 110.04(8) . . ?
C1 C2 C3 109.95(9) . . ?
C1 C2 C7 108.50(9) . . ?
C3 C2 C7 109.56(9) . . ?
C2 C3 C4 109.38(9) . . ?
C10 C4 C5 109.71(9) . . ?
C10 C4 C3 109.51(9) . . ?
C5 C4 C3 109.27(9) . . ?
C4 C5 C6 109.64(9) . . ?
C1 C6 C5 109.74(9) . . ?
C1 C6 C9 108.70(8) . . ?
C5 C6 C9 109.44(9) . . ?
C8 C7 C2 109.76(9) . . ?
C7 C8 C10 109.42(10) . . ?
C7 C8 C9 109.09(9) . . ?
C10 C8 C9 109.63(9) . . ?
C8 C9 C6 109.56(9) . . ?
C4 C10 C8 109.59(9) . . ?
O20 C11 C16 108.73(8) . . ?
O20 C11 C12 110.83(9) . . ?
C16 C11 C12 110.09(8) . . ?
C11 C12 C13 109.75(8) . . ?
C11 C12 C17 108.69(8) . . ?
C13 C12 C17 109.68(9) . . ?
C12 C13 C14 109.46(9) . . ?
C20 C14 C13 109.30(9) . . ?
C20 C14 C15 109.49(9) . . ?
C13 C14 C15 109.38(9) . . ?
C16 C15 C14 109.57(8) . . ?
C11 C16 C15 109.78(9) . . ?
C11 C16 C19 108.65(8) . . ?
C15 C16 C19 109.55(9) . . ?
C18 C17 C12 109.44(8) . . ?
C20 C18 C17 109.56(9) . . ?
C20 C18 C19 109.58(9) . . ?
C17 C18 C19 109.09(9) . . ?
C18 C19 C16 109.62(8) . . ?
C18 C20 C14 109.78(9) . . ?
O30 C21 C22 108.97(9) . . ?
O30 C21 C26 110.67(8) . . ?
C22 C21 C26 109.99(9) . . ?
C21 C22 C23 109.99(9) . . ?
C21 C22 C27 108.62(9) . . ?
C23 C22 C27 109.61(9) . . ?
C22 C23 C24 109.40(9) . . ?
C25 C24 C30 109.75(10) . . ?
C25 C24 C23 109.35(9) . . ?
C30 C24 C23 109.25(10) . . ?
C24 C25 C26 109.61(9) . . ?
C21 C26 C25 109.66(9) . . ?
C21 C26 C29 108.80(9) . . ?
C25 C26 C29 109.47(9) . . ?
C28 C27 C22 109.58(9) . . ?
C29 C28 C27 109.10(10) . . ?
C29 C28 C30 109.82(10) . . ?
C27 C28 C30 109.41(10) . . ?
C28 C29 C26 109.51(9) . . ?
C24 C30 C28 109.55(9) . . ?

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
O10 C1 C2 C3 62.54(11) . . . . ?
C6 C1 C2 C3 -58.87(11) . . . . ?
O10 C1 C2 C7 -177.66(8) . . . . ?
C6 C1 C2 C7 60.93(11) . . . . ?
C1 C2 C3 C4 59.51(11) . . . . ?
C7 C2 C3 C4 -59.65(11) . . . . ?
C2 C3 C4 C10 60.05(11) . . . . ?
C2 C3 C4 C5 -60.15(11) . . . . ?
C10 C4 C5 C6 -59.79(12) . . . . ?
C3 C4 C5 C6 60.28(12) . . . . ?
O10 C1 C6 C5 -61.76(11) . . . . ?
C2 C1 C6 C5 58.72(11) . . . . ?
O10 C1 C6 C9 178.59(8) . . . . ?
C2 C1 C6 C9 -60.93(11) . . . . ?
C4 C5 C6 C1 -59.52(11) . . . . ?
C4 C5 C6 C9 59.67(11) . . . . ?
C1 C2 C7 C8 -60.43(11) . . . . ?
C3 C2 C7 C8 59.61(12) . . . . ?
C2 C7 C8 C10 -59.58(12) . . . . ?
C2 C7 C8 C9 60.34(12) . . . . ?
C7 C8 C9 C6 -60.10(11) . . . . ?
C10 C8 C9 C6 59.70(11) . . . . ?
C1 C6 C9 C8 60.17(11) . . . . ?
C5 C6 C9 C8 -59.66(11) . . . . ?
C5 C4 C10 C8 59.69(12) . . . . ?
C3 C4 C10 C8 -60.24(12) . . . . ?
C7 C8 C10 C4 59.92(12) . . . . ?
C9 C8 C10 C4 -59.68(12) . . . . ?
O20 C11 C12 C13 61.26(11) . . . . ?
C16 C11 C12 C13 -59.07(11) . . . . ?
O20 C11 C12 C17 -178.79(8) . . . . ?
C16 C11 C12 C17 60.87(11) . . . . ?
C11 C12 C13 C14 59.46(11) . . . . ?
C17 C12 C13 C14 -59.88(11) . . . . ?
C12 C13 C14 C20 59.90(12) . . . . ?
C12 C13 C14 C15 -59.97(11) . . . . ?
C20 C14 C15 C16 -59.76(11) . . . . ?
C13 C14 C15 C16 59.99(11) . . . . ?
O20 C11 C16 C15 -62.54(11) . . . . ?
C12 C11 C16 C15 59.05(11) . . . . ?
O20 C11 C16 C19 177.67(8) . . . . ?
C12 C11 C16 C19 -60.74(11) . . . . ?
C14 C15 C16 C11 -59.46(11) . . . . ?
C14 C15 C16 C19 59.77(11) . . . . ?
C11 C12 C17 C18 -60.35(11) . . . . ?
C13 C12 C17 C18 59.64(11) . . . . ?
C12 C17 C18 C20 -59.55(11) . . . . ?
C12 C17 C18 C19 60.41(11) . . . . ?
C20 C18 C19 C16 59.53(11) . . . . ?
C17 C18 C19 C16 -60.41(11) . . . . ?
C11 C16 C19 C18 60.25(11) . . . . ?
C15 C16 C19 C18 -59.68(11) . . . . ?
C17 C18 C20 C14 60.00(12) . . . . ?
C19 C18 C20 C14 -59.66(12) . . . . ?
C13 C14 C20 C18 -60.07(12) . . . . ?
C15 C14 C20 C18 59.73(12) . . . . ?
O30 C21 C22 C23 62.39(11) . . . . ?
C26 C21 C22 C23 -59.09(11) . . . . ?
O30 C21 C22 C27 -177.65(9) . . . . ?
C26 C21 C22 C27 60.87(11) . . . . ?
C21 C22 C23 C24 59.50(12) . . . . ?
C27 C22 C23 C24 -59.85(12) . . . . ?
C22 C23 C24 C25 -59.90(12) . . . . ?
C22 C23 C24 C30 60.24(12) . . . . ?
C30 C24 C25 C26 -59.72(12) . . . . ?
C23 C24 C25 C26 60.11(12) . . . . ?
O30 C21 C26 C25 -61.49(12) . . . . ?
C22 C21 C26 C25 58.97(11) . . . . ?
O30 C21 C26 C29 178.81(9) . . . . ?
C22 C21 C26 C29 -60.73(12) . . . . ?
C24 C25 C26 C21 -59.53(12) . . . . ?
C24 C25 C26 C29 59.77(11) . . . . ?
C21 C22 C27 C28 -60.59(12) . . . . ?
C23 C22 C27 C28 59.61(12) . . . . ?
C22 C27 C28 C29 60.52(13) . . . . ?
C22 C27 C28 C30 -59.64(13) . . . . ?
C27 C28 C29 C26 -60.21(12) . . . . ?
C30 C28 C29 C26 59.70(12) . . . . ?
C21 C26 C29 C28 60.06(12) . . . . ?
C25 C26 C29 C28 -59.76(12) . . . . ?
C25 C24 C30 C28 59.40(13) . . . . ?
C23 C24 C30 C28 -60.48(13) . . . . ?
C29 C28 C30 C24 -59.49(13) . . . . ?
C27 C28 C30 C24 60.22(13) . . . . ?

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O10 H10 O20 0.97(3) 1.71(3) 2.6766(13) 177(3) 1_545 yes
O20 H20 O30 0.93(4) 1.75(4) 2.6790(16) 177.0(17) . yes
O30 H30 O10 0.97(2) 1.71(2) 2.6775(12) 176(2) 2_666 yes

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.066



####################################################################### 
# 
# 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_Ada2Me2ol_Pbcn130K
_database_code_depnum_ccdc_archive 'CCDC 2129550'
loop_
_audit_author_name
_audit_author_address
'Ph. Negrier'
;Universite de Bordeaux
France
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT110_Ada2Me2ol_Pbcn130K  
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: Powder diffraction has shown supplementary peaks impossible with half lattice and Pcca group
;
_vrf_PLAT112_Ada2Me2ol_Pbcn130K  
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       a/2        100 %Fit
RESPONSE: Powder diffraction has shown supplementary peaks impossible with half lattice and Pcca group
;
_vrf_PLAT113_Ada2Me2ol_Pbcn130K  
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       Pcca Check
RESPONSE: Powder diffraction has shown supplementary peaks impossible with half lattice and Pcca group
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 O'
_chemical_formula_sum            'C11 H18 O'
_chemical_formula_weight         166.25

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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.
;

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,y,1/2-z
5 -x,-y,-z
6 1/2+x,1/2+y,1/2-z
7 1/2-x,1/2+y,z
8 x,-y,1/2+z

_cell_length_a                   18.7366(2)
_cell_length_b                   9.07580(10)
_cell_length_c                   21.2147(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3607.55(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    8133
_cell_measurement_theta_min      4.7110
_cell_measurement_theta_max      73.3070

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.579
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'FRX Rotating Anode'
_diffrn_measurement_device_type  'Rigaku PILATUS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            12431
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.168
_diffrn_reflns_theta_max         73.469
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3603
_reflns_number_gt                3397
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+1.0244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3603
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
H1 H 0.2230(8) 0.5484(18) 0.4953(7) 0.048(4) Uiso 1 1 d . . . . .
H21 H 0.1982(8) 0.1955(18) 0.0149(7) 0.045(4) Uiso 1 1 d . . . . .
O1 O 0.19488(4) 0.60812(7) 0.47820(3) 0.02216(17) Uani 1 1 d . . . . .
C1 C 0.14305(5) 0.51932(10) 0.44474(4) 0.0171(2) Uani 1 1 d . . . . .
C2 C 0.18188(5) 0.43091(10) 0.39292(4) 0.0175(2) Uani 1 1 d . . . . .
H2 H 0.2165 0.3614 0.4129 0.021 Uiso 1 1 calc R U . . .
C3 C 0.22236(5) 0.53715(11) 0.34912(5) 0.0219(2) Uani 1 1 d . . . . .
H3A H 0.2580 0.5934 0.3737 0.026 Uiso 1 1 calc R U . . .
H3B H 0.2479 0.4804 0.3163 0.026 Uiso 1 1 calc R U . . .
C4 C 0.16946(5) 0.64406(11) 0.31788(5) 0.0229(2) Uani 1 1 d . . . . .
H4 H 0.1960 0.7134 0.2897 0.027 Uiso 1 1 calc R U . . .
C5 C 0.13017(5) 0.73194(10) 0.36907(4) 0.0210(2) Uani 1 1 d . . . . .
H5A H 0.0959 0.8008 0.3492 0.025 Uiso 1 1 calc R U . . .
H5B H 0.1649 0.7904 0.3938 0.025 Uiso 1 1 calc R U . . .
C6 C 0.09020(5) 0.62522(10) 0.41277(4) 0.0182(2) Uani 1 1 d . . . . .
H6 H 0.0642 0.6827 0.4458 0.022 Uiso 1 1 calc R U . . .
C7 C 0.03594(5) 0.53712(11) 0.37322(5) 0.0218(2) Uani 1 1 d . . . . .
H7A H 0.0091 0.4690 0.4009 0.026 Uiso 1 1 calc R U . . .
H7B H 0.0015 0.6055 0.3534 0.026 Uiso 1 1 calc R U . . .
C8 C 0.07504(5) 0.44905(11) 0.32201(5) 0.0224(2) Uani 1 1 d . . . . .
H8 H 0.0396 0.3916 0.2967 0.027 Uiso 1 1 calc R U . . .
C9 C 0.11512(6) 0.55623(12) 0.27882(5) 0.0257(2) Uani 1 1 d . . . . .
H9A H 0.0809 0.6245 0.2586 0.031 Uiso 1 1 calc R U . . .
H9B H 0.1401 0.5007 0.2453 0.031 Uiso 1 1 calc R U . . .
C10 C 0.12814(5) 0.34302(11) 0.35317(5) 0.0217(2) Uani 1 1 d . . . . .
H10A H 0.1538 0.2863 0.3204 0.026 Uiso 1 1 calc R U . . .
H10B H 0.1021 0.2725 0.3804 0.026 Uiso 1 1 calc R U . . .
C11 C 0.10714(6) 0.42189(11) 0.49391(5) 0.0253(2) Uani 1 1 d . . . . .
H11A H 0.1430 0.3590 0.5141 0.038 Uiso 1 1 calc R U . . .
H11B H 0.0711 0.3601 0.4734 0.038 Uiso 1 1 calc R U . . .
H11C H 0.0842 0.4839 0.5259 0.038 Uiso 1 1 calc R U . . .
O21 O 0.20976(3) 0.11435(7) 0.03453(3) 0.01975(17) Uani 1 1 d . . . . .
C21 C 0.14664(5) 0.04300(10) 0.05896(4) 0.0165(2) Uani 1 1 d . . . . .
C22 C 0.09800(5) 0.15340(10) 0.09379(4) 0.0187(2) Uani 1 1 d . . . . .
H22 H 0.0789 0.2268 0.0629 0.022 Uiso 1 1 calc R U . . .
C23 C 0.14026(5) 0.23432(11) 0.14506(5) 0.0222(2) Uani 1 1 d . . . . .
H23A H 0.1089 0.3060 0.1668 0.027 Uiso 1 1 calc R U . . .
H23B H 0.1804 0.2890 0.1257 0.027 Uiso 1 1 calc R U . . .
C24 C 0.16912(5) 0.12194(11) 0.19278(4) 0.0225(2) Uani 1 1 d . . . . .
H24 H 0.1974 0.1744 0.2258 0.027 Uiso 1 1 calc R U . . .
C25 C 0.21708(5) 0.01020(11) 0.15887(4) 0.0217(2) Uani 1 1 d . . . . .
H25A H 0.2357 -0.0624 0.1896 0.026 Uiso 1 1 calc R U . . .
H25B H 0.2582 0.0618 0.1396 0.026 Uiso 1 1 calc R U . . .
C26 C 0.17415(5) -0.06987(10) 0.10737(4) 0.0180(2) Uani 1 1 d . . . . .
H26 H 0.2057 -0.1428 0.0856 0.022 Uiso 1 1 calc R U . . .
C27 C 0.11164(5) -0.15140(11) 0.13867(4) 0.0224(2) Uani 1 1 d . . . . .
H27A H 0.0836 -0.2044 0.1062 0.027 Uiso 1 1 calc R U . . .
H27B H 0.1302 -0.2247 0.1691 0.027 Uiso 1 1 calc R U . . .
C28 C 0.06358(5) -0.04054(11) 0.17303(4) 0.0223(2) Uani 1 1 d . . . . .
H28 H 0.0227 -0.0937 0.1930 0.027 Uiso 1 1 calc R U . . .
C29 C 0.10662(5) 0.04035(12) 0.22393(4) 0.0244(2) Uani 1 1 d . . . . .
H29A H 0.1250 -0.0313 0.2552 0.029 Uiso 1 1 calc R U . . .
H29B H 0.0755 0.1115 0.2462 0.029 Uiso 1 1 calc R U . . .
C30 C 0.03520(5) 0.07218(11) 0.12536(5) 0.0225(2) Uani 1 1 d . . . . .
H30A H 0.0041 0.1442 0.1471 0.027 Uiso 1 1 calc R U . . .
H30B H 0.0064 0.0213 0.0929 0.027 Uiso 1 1 calc R U . . .
C31 C 0.10884(5) -0.02727(11) 0.00277(4) 0.0231(2) Uani 1 1 d . . . . .
H31A H 0.0935 0.0499 -0.0265 0.035 Uiso 1 1 calc R U . . .
H31B H 0.0671 -0.0824 0.0176 0.035 Uiso 1 1 calc R U . . .
H31C H 0.1417 -0.0945 -0.0188 0.035 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_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4479(11) . . yes
O1 H1 0.838(16) . . no
O21 C21 1.4445(11) . . yes
O21 H21 0.873(16) . . no
C1 C11 1.5241(14) . . no
C1 C6 1.5376(13) . . no
C1 C2 1.5433(13) . . no
C2 C10 1.5366(13) . . no
C2 C3 1.5390(13) . . no
C3 C4 1.5372(14) . . no
C4 C9 1.5358(15) . . no
C4 C5 1.5354(13) . . no
C5 C6 1.5357(13) . . no
C6 C7 1.5417(13) . . no
C7 C8 1.5349(14) . . no
C8 C10 1.5339(14) . . no
C8 C9 1.5329(15) . . no
C2 H2 1.0000 . . no
C3 H3B 0.9900 . . no
C3 H3A 0.9900 . . no
C4 H4 1.0000 . . no
C5 H5B 0.9900 . . no
C5 H5A 0.9900 . . no
C6 H6 1.0000 . . no
C7 H7B 0.9900 . . no
C7 H7A 0.9900 . . no
C8 H8 1.0000 . . no
C9 H9B 0.9900 . . no
C9 H9A 0.9900 . . no
C10 H10A 0.9900 . . no
C10 H10B 0.9900 . . no
C11 H11B 0.9800 . . no
C11 H11A 0.9800 . . no
C11 H11C 0.9800 . . no
C21 C26 1.5394(13) . . no
C21 C31 1.5262(13) . . no
C21 C22 1.5429(13) . . no
C22 C30 1.5416(13) . . no
C22 C23 1.5328(13) . . no
C23 C24 1.5354(14) . . no
C24 C29 1.5351(13) . . no
C24 C25 1.5341(13) . . no
C25 C26 1.5391(13) . . no
C26 C27 1.5363(13) . . no
C27 C28 1.5345(13) . . no
C28 C29 1.5347(13) . . no
C28 C30 1.5337(14) . . no
C22 H22 1.0000 . . no
C23 H23A 0.9900 . . no
C23 H23B 0.9900 . . no
C24 H24 1.0000 . . no
C25 H25A 0.9900 . . no
C25 H25B 0.9900 . . no
C26 H26 1.0000 . . no
C27 H27A 0.9900 . . no
C27 H27B 0.9900 . . no
C28 H28 1.0000 . . no
C29 H29A 0.9900 . . no
C29 H29B 0.9900 . . no
C30 H30A 0.9900 . . no
C30 H30B 0.9900 . . no
C31 H31A 0.9800 . . no
C31 H31B 0.9800 . . no
C31 H31C 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 105.9(11) . . . no
C21 O21 H21 110.3(10) . . . no
O1 C1 C2 108.81(7) . . . yes
C2 C1 C6 108.32(7) . . . no
C2 C1 C11 113.21(8) . . . no
O1 C1 C11 106.47(7) . . . yes
C6 C1 C11 112.35(8) . . . no
O1 C1 C6 107.47(7) . . . yes
C1 C2 C10 110.60(8) . . . no
C1 C2 C3 109.68(7) . . . no
C3 C2 C10 108.47(7) . . . no
C2 C3 C4 109.76(8) . . . no
C3 C4 C9 109.42(8) . . . no
C3 C4 C5 109.40(8) . . . no
C5 C4 C9 109.48(8) . . . no
C4 C5 C6 109.46(7) . . . no
C1 C6 C7 109.91(7) . . . no
C1 C6 C5 110.27(7) . . . no
C5 C6 C7 108.67(7) . . . no
C6 C7 C8 109.91(8) . . . no
C7 C8 C9 109.05(8) . . . no
C7 C8 C10 109.35(8) . . . no
C9 C8 C10 109.75(8) . . . no
C4 C9 C8 109.37(8) . . . no
C2 C10 C8 109.62(8) . . . no
C3 C2 H2 109.00 . . . no
C10 C2 H2 109.00 . . . no
C1 C2 H2 109.00 . . . no
C2 C3 H3B 110.00 . . . no
C4 C3 H3A 110.00 . . . no
C4 C3 H3B 110.00 . . . no
H3A C3 H3B 108.00 . . . no
C2 C3 H3A 110.00 . . . no
C3 C4 H4 110.00 . . . no
C5 C4 H4 110.00 . . . no
C9 C4 H4 109.00 . . . no
C4 C5 H5A 110.00 . . . no
C4 C5 H5B 110.00 . . . no
C6 C5 H5B 110.00 . . . no
H5A C5 H5B 108.00 . . . no
C6 C5 H5A 110.00 . . . no
C1 C6 H6 109.00 . . . no
C7 C6 H6 109.00 . . . no
C5 C6 H6 109.00 . . . no
C6 C7 H7A 110.00 . . . no
C8 C7 H7A 110.00 . . . no
C8 C7 H7B 110.00 . . . no
H7A C7 H7B 108.00 . . . no
C6 C7 H7B 110.00 . . . no
C7 C8 H8 110.00 . . . no
C10 C8 H8 110.00 . . . no
C9 C8 H8 110.00 . . . no
C4 C9 H9A 110.00 . . . no
C8 C9 H9A 110.00 . . . no
C8 C9 H9B 110.00 . . . no
H9A C9 H9B 108.00 . . . no
C4 C9 H9B 110.00 . . . no
C2 C10 H10B 110.00 . . . no
C8 C10 H10A 110.00 . . . no
C2 C10 H10A 110.00 . . . no
H10A C10 H10B 108.00 . . . no
C8 C10 H10B 110.00 . . . no
C1 C11 H11B 109.00 . . . no
C1 C11 H11C 110.00 . . . no
H11A C11 H11B 109.00 . . . no
H11A C11 H11C 109.00 . . . no
H11B C11 H11C 109.00 . . . no
C1 C11 H11A 110.00 . . . no
O21 C21 C22 111.37(7) . . . yes
O21 C21 C31 106.68(7) . . . yes
C22 C21 C26 108.09(7) . . . no
C22 C21 C31 111.80(8) . . . no
C26 C21 C31 113.48(8) . . . no
O21 C21 C26 105.28(7) . . . yes
C21 C22 C23 110.24(8) . . . no
C21 C22 C30 110.39(7) . . . no
C23 C22 C30 108.37(7) . . . no
C22 C23 C24 109.36(8) . . . no
C23 C24 C29 109.61(8) . . . no
C25 C24 C29 109.26(8) . . . no
C23 C24 C25 109.65(7) . . . no
C24 C25 C26 109.81(7) . . . no
C21 C26 C25 109.54(7) . . . no
C21 C26 C27 110.71(8) . . . no
C25 C26 C27 108.60(7) . . . no
C26 C27 C28 109.69(8) . . . no
C27 C28 C29 109.85(8) . . . no
C27 C28 C30 109.12(7) . . . no
C29 C28 C30 109.09(8) . . . no
C24 C29 C28 109.19(7) . . . no
C22 C30 C28 109.93(8) . . . no
C21 C22 H22 109.00 . . . no
C23 C22 H22 109.00 . . . no
C30 C22 H22 109.00 . . . no
C22 C23 H23A 110.00 . . . no
C22 C23 H23B 110.00 . . . no
C24 C23 H23A 110.00 . . . no
C24 C23 H23B 110.00 . . . no
H23A C23 H23B 108.00 . . . no
C23 C24 H24 109.00 . . . no
C25 C24 H24 109.00 . . . no
C29 C24 H24 109.00 . . . no
C24 C25 H25A 110.00 . . . no
C24 C25 H25B 110.00 . . . no
C26 C25 H25A 110.00 . . . no
C26 C25 H25B 110.00 . . . no
H25A C25 H25B 108.00 . . . no
C21 C26 H26 109.00 . . . no
C25 C26 H26 109.00 . . . no
C27 C26 H26 109.00 . . . no
C26 C27 H27A 110.00 . . . no
C26 C27 H27B 110.00 . . . no
C28 C27 H27A 110.00 . . . no
C28 C27 H27B 110.00 . . . no
H27A C27 H27B 108.00 . . . no
C27 C28 H28 110.00 . . . no
C29 C28 H28 110.00 . . . no
C30 C28 H28 110.00 . . . no
C24 C29 H29A 110.00 . . . no
C24 C29 H29B 110.00 . . . no
C28 C29 H29A 110.00 . . . no
C28 C29 H29B 110.00 . . . no
H29A C29 H29B 108.00 . . . no
C22 C30 H30A 110.00 . . . no
C22 C30 H30B 110.00 . . . no
C28 C30 H30A 110.00 . . . no
C28 C30 H30B 110.00 . . . no
H30A C30 H30B 108.00 . . . no
C21 C31 H31A 109.00 . . . no
C21 C31 H31B 109.00 . . . no
C21 C31 H31C 109.00 . . . no
H31A C31 H31B 110.00 . . . no
H31A C31 H31C 109.00 . . . no
H31B C31 H31C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -56.51(9) . . . . no
O1 C1 C2 C10 -176.11(7) . . . . no
C6 C1 C2 C3 60.04(9) . . . . no
C6 C1 C2 C10 -59.56(9) . . . . no
C11 C1 C2 C3 -174.67(8) . . . . no
C11 C1 C2 C10 65.74(10) . . . . no
O1 C1 C6 C5 57.09(9) . . . . no
O1 C1 C6 C7 176.87(7) . . . . no
C2 C1 C6 C5 -60.32(9) . . . . no
C2 C1 C6 C7 59.46(9) . . . . no
C11 C1 C6 C5 173.88(7) . . . . no
C11 C1 C6 C7 -66.34(10) . . . . no
C1 C2 C3 C4 -60.32(10) . . . . no
C10 C2 C3 C4 60.58(10) . . . . no
C1 C2 C10 C8 59.83(10) . . . . no
C3 C2 C10 C8 -60.49(10) . . . . no
C2 C3 C4 C5 59.53(10) . . . . no
C2 C3 C4 C9 -60.39(10) . . . . no
C3 C4 C5 C6 -59.26(10) . . . . no
C9 C4 C5 C6 60.63(10) . . . . no
C3 C4 C9 C8 59.42(11) . . . . no
C5 C4 C9 C8 -60.46(10) . . . . no
C4 C5 C6 C1 60.40(9) . . . . no
C4 C5 C6 C7 -60.13(9) . . . . no
C1 C6 C7 C8 -60.40(10) . . . . no
C5 C6 C7 C8 60.35(10) . . . . no
C6 C7 C8 C9 -60.47(10) . . . . no
C6 C7 C8 C10 59.54(10) . . . . no
C7 C8 C9 C4 60.14(10) . . . . no
C10 C8 C9 C4 -59.63(11) . . . . no
C7 C8 C10 C2 -59.04(10) . . . . no
C9 C8 C10 C2 60.55(10) . . . . no
O21 C21 C22 C23 -54.36(9) . . . . no
O21 C21 C22 C30 -174.05(7) . . . . no
C26 C21 C22 C23 60.82(9) . . . . no
C26 C21 C22 C30 -58.87(9) . . . . no
C31 C21 C22 C23 -173.60(8) . . . . no
C31 C21 C22 C30 66.72(9) . . . . no
O21 C21 C26 C25 58.65(9) . . . . no
O21 C21 C26 C27 178.39(7) . . . . no
C22 C21 C26 C25 -60.46(9) . . . . no
C22 C21 C26 C27 59.28(9) . . . . no
C31 C21 C26 C25 174.95(7) . . . . no
C31 C21 C26 C27 -65.31(10) . . . . no
C21 C22 C23 C24 -60.32(9) . . . . no
C30 C22 C23 C24 60.59(10) . . . . no
C21 C22 C30 C28 59.98(10) . . . . no
C23 C22 C30 C28 -60.83(10) . . . . no
C22 C23 C24 C25 58.94(10) . . . . no
C22 C23 C24 C29 -60.99(10) . . . . no
C23 C24 C25 C26 -59.30(10) . . . . no
C29 C24 C25 C26 60.85(9) . . . . no
C23 C24 C29 C28 60.25(10) . . . . no
C25 C24 C29 C28 -59.93(10) . . . . no
C24 C25 C26 C21 60.51(9) . . . . no
C24 C25 C26 C27 -60.51(10) . . . . no
C21 C26 C27 C28 -60.40(9) . . . . no
C25 C26 C27 C28 59.89(9) . . . . no
C26 C27 C28 C29 -60.11(9) . . . . no
C26 C27 C28 C30 59.44(9) . . . . no
C27 C28 C29 C24 59.75(10) . . . . no
C30 C28 C29 C24 -59.82(10) . . . . no
C27 C28 C30 C22 -59.38(10) . . . . no
C29 C28 C30 C22 60.64(10) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 O21 2.8018(9) . 8_565 no
O1 O21 2.9491(9) . 2_555 no
O21 O1 2.9491(9) . 2_554 no
O21 O1 2.8018(9) . 8_564 no
O1 H5B 2.5000 . . no
O1 H21 1.946(16) . 8_565 no
O1 H3A 2.5200 . . no
O21 H25B 2.4500 . . no
O21 H11A 2.8000 . 2_554 no
O21 H23B 2.5600 . . no
O21 H1 2.112(16) . 2_554 no
C1 C9 3.5744(14) . . no
C3 C7 3.5301(13) . . no
C5 C10 3.5460(13) . . no
C7 C3 3.5301(13) . . no
C9 C1 3.5744(14) . . no
C10 C5 3.5460(13) . . no
C11 C31 3.5866(14) . 8_555 no
C21 C29 3.5793(12) . . no
C23 C27 3.5441(14) . . no
C25 C30 3.5263(13) . . no
C27 C23 3.5441(14) . . no
C29 C21 3.5793(12) . . no
C30 C25 3.5263(13) . . no
C31 C11 3.5866(14) . 8_554 no
C5 H31A 3.0500 . 8_565 no
C7 H11B 2.7400 . . no
C9 H27B 3.0700 . 1_565 no
C10 H30A 3.0700 . 4_555 no
C10 H11B 2.7700 . . no
C11 H31C 3.0500 . 8_555 no
C11 H7A 2.7300 . . no
C11 H10B 2.7700 . . no
C21 H1 2.912(15) . 2_554 no
C23 H21 2.988(15) . . no
C25 H23B 2.8700 . 7_545 no
C26 H23B 3.0400 . 7_545 no
C26 H1 3.067(15) . 2_554 no
C27 H31B 2.7700 . . no
C27 H7B 3.0600 . 4_545 no
C30 H31B 2.7500 . . no
C31 H30B 2.7400 . . no
C31 H30B 2.9600 . 5_555 no
C31 H11A 3.0900 . 8_554 no
C31 H27A 2.7600 . . no
H1 H2 2.4400 . . no
H1 H11A 2.3200 . . no
H1 O21 2.112(16) . 2_555 no
H1 C26 3.067(15) . 2_555 no
H1 H26 2.4900 . 2_555 no
H1 H31C 2.5900 . 2_555 no
H1 H21 2.41(2) . 8_565 no
H1 C21 2.912(15) . 2_555 no
H2 H11A 2.5500 . . no
H2 H5B 2.3500 . 7_545 no
H2 H1 2.4400 . . no
H3A O1 2.5200 . . no
H3A H5B 2.5300 . . no
H3B H9B 2.5300 . . no
H3B H10A 2.4900 . . no
H4 H24 2.4400 . 7_555 no
H5A H7B 2.5100 . . no
H5A H9A 2.5200 . . no
H5A H28 2.5800 . 4_565 no
H5A H29A 2.5700 . 1_565 no
H5B H31A 2.6000 . 8_565 no
H5B O1 2.5000 . . no
H5B H2 2.3500 . 7_555 no
H5B H3A 2.5300 . . no
H6 H11C 2.5100 . . no
H6 H31A 2.5600 . 8_565 no
H7A C11 2.7300 . . no
H7A H10B 2.5300 . . no
H7A H11C 2.3800 . 5_566 no
H7A H11B 2.1700 . . no
H7B H5A 2.5100 . . no
H7B H9A 2.5100 . . no
H7B H27A 2.5000 . 4_565 no
H7B C27 3.0600 . 4_565 no
H8 H8 2.4800 . 4_555 no
H9A H27B 2.5200 . 1_565 no
H9A H7B 2.5100 . . no
H9A H5A 2.5200 . . no
H9B H10A 2.5300 . . no
H9B H3B 2.5300 . . no
H9B H23A 2.5000 . . no
H10A H9B 2.5300 . . no
H10A H3B 2.4900 . . no
H10A H24 2.3900 . . no
H10B H7A 2.5300 . . no
H10B H11B 2.2100 . . no
H10B C11 2.7700 . . no
H10B H30A 2.3800 . 4_555 no
H11A H1 2.3200 . . no
H11A H2 2.5500 . . no
H11A H31C 2.5000 . 8_555 no
H11A C31 3.0900 . 8_555 no
H11A O21 2.8000 . 2_555 no
H11B H7A 2.1700 . . no
H11B C10 2.7700 . . no
H11B C7 2.7400 . . no
H11B H10B 2.2100 . . no
H11C H6 2.5100 . . no
H11C H7A 2.3800 . 5_566 no
H21 C23 2.988(15) . . no
H21 H22 2.4700 . . no
H21 H23B 2.5200 . . no
H21 H31A 2.5200 . . no
H21 O1 1.946(16) . 8_564 no
H21 H1 2.41(2) . 8_564 no
H22 H21 2.4700 . . no
H22 H31A 2.5000 . . no
H23A H9B 2.5000 . . no
H23A H29B 2.5200 . . no
H23A H30A 2.4900 . . no
H23B O21 2.5600 . . no
H23B H21 2.5200 . . no
H23B H25B 2.5400 . . no
H23B C25 2.8700 . 7_555 no
H23B C26 3.0400 . 7_555 no
H23B H25A 2.4800 . 7_555 no
H23B H26 2.3800 . 7_555 no
H24 H10A 2.3900 . . no
H24 H4 2.4400 . 7_545 no
H25A H27B 2.5000 . . no
H25A H29A 2.5100 . . no
H25A H23B 2.4800 . 7_545 no
H25B O21 2.4500 . . no
H25B H23B 2.5400 . . no
H26 H31C 2.5600 . . no
H26 H1 2.4900 . 2_554 no
H26 H23B 2.3800 . 7_545 no
H27A C31 2.7600 . . no
H27A H30B 2.5200 . . no
H27A H31B 2.2000 . . no
H27A H7B 2.5000 . 4_545 no
H27B C9 3.0700 . 1_545 no
H27B H9A 2.5200 . 1_545 no
H27B H25A 2.5000 . . no
H27B H29A 2.5400 . . no
H28 H5A 2.5800 . 4_545 no
H28 H28 2.5600 . 4_555 no
H29A H5A 2.5700 . 1_545 no
H29A H25A 2.5100 . . no
H29A H27B 2.5400 . . no
H29B H23A 2.5200 . . no
H29B H30A 2.5100 . . no
H30A H23A 2.4900 . . no
H30A H29B 2.5100 . . no
H30A C10 3.0700 . 4_555 no
H30A H10B 2.3800 . 4_555 no
H30B C31 2.7400 . . no
H30B H27A 2.5200 . . no
H30B H31B 2.1800 . . no
H30B C31 2.9600 . 5_555 no
H30B H31A 2.4300 . 5_555 no
H31A H21 2.5200 . . no
H31A H22 2.5000 . . no
H31A H30B 2.4300 . 5_555 no
H31A C5 3.0500 . 8_564 no
H31A H5B 2.6000 . 8_564 no
H31A H6 2.5600 . 8_564 no
H31B C27 2.7700 . . no
H31B C30 2.7500 . . no
H31B H27A 2.2000 . . no
H31B H30B 2.1800 . . no
H31C H26 2.5600 . . no
H31C H1 2.5900 . 2_554 no
H31C C11 3.0500 . 8_554 no
H31C H11A 2.5000 . 8_554 no

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1 O21 0.838(16) 2.112(16) 2.9491(9) 175.8(16) 2_555 yes
O21 H21 O1 0.873(16) 1.946(16) 2.8018(9) 166.2(14) 8_564 yes
C3 H3A O1 0.9900 2.5200 2.8599(12) 100.00 . yes
C5 H5B O1 0.9900 2.5000 2.8448(11) 100.00 . yes
C23 H23B O21 0.9900 2.5600 2.8948(12) 100.00 . yes
C25 H25B O21 0.9900 2.4500 2.8054(11) 100.00 . yes

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.059



####################################################################### 
# 
# 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_ada2oh293K
_database_code_depnum_ccdc_archive 'CCDC 2129549'
loop_
_audit_author_name
_audit_author_address
'Ph. Negrier'
;Universite de Bordeaux
France
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 O'
_chemical_formula_sum            'C10 H16 O'
_chemical_formula_weight         152.23

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.5770(5)
_cell_length_b                   11.5948(5)
_cell_length_c                   11.5876(4)
_cell_angle_alpha                81.718(3)
_cell_angle_beta                 70.661(3)
_cell_angle_gamma                61.489(4)
_cell_volume                     1289.50(10)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12314
_cell_measurement_theta_min      4.3060
_cell_measurement_theta_max      75.0000

_cell_special_details            
;
PLAT155  The Triclinic Unitcell is NOT Reduced
Reply : To follow the evolution of the cell parameters as a function of temperature in the different
crystalline phases they are kept in the same order as in the low temperature phase.
;
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.565
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_detector                 PILT
_diffrn_measurement_device       'AFC11 (Right): Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku PILATUS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            20346
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.044
_diffrn_reflns_theta_max         72.108
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5015
_reflns_number_gt                4318
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    'Superflip 03/15/13 12:43'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0812P)²+0.4813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_extinction_coef       0.0118(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5015
_refine_ls_number_parameters     317
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1836
_refine_ls_wR_factor_gt          0.1791
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O10 O 0.64482(17) 0.11294(12) 0.38059(13) 0.0736(4) Uani 1 1 d D . . . .
C1 C 0.54691(19) 0.22710(16) 0.33629(16) 0.0542(4) Uani 1 1 d . . . . .
H1 H 0.4578 0.2259 0.3643 0.065 Uiso 1 1 calc R U . . .
C2 C 0.52965(19) 0.35107(16) 0.38569(15) 0.0553(4) Uani 1 1 d . . . . .
H2 H 0.4998 0.3509 0.4753 0.066 Uiso 1 1 calc R U . . .
C3 C 0.6655(2) 0.3566(2) 0.3394(2) 0.0687(5) Uani 1 1 d . . . . .
H3A H 0.6551 0.4347 0.3719 0.082 Uiso 1 1 calc R U . . .
H3B H 0.7349 0.2805 0.3672 0.082 Uiso 1 1 calc R U . . .
C4 C 0.7109(2) 0.3589(2) 0.2009(2) 0.0737(6) Uani 1 1 d . . . . .
H4 H 0.7982 0.3637 0.1713 0.088 Uiso 1 1 calc R U . . .
C5 C 0.7302(2) 0.2328(2) 0.15266(19) 0.0738(6) Uani 1 1 d . . . . .
H5A H 0.7617 0.2313 0.0639 0.089 Uiso 1 1 calc R U . . .
H5B H 0.7996 0.1572 0.1810 0.089 Uiso 1 1 calc R U . . .
C6 C 0.5952(2) 0.22600(17) 0.19720(16) 0.0568(4) Uani 1 1 d . . . . .
H6 H 0.6075 0.1456 0.1657 0.068 Uiso 1 1 calc R U . . .
C7 C 0.4215(2) 0.46883(19) 0.34067(19) 0.0707(6) Uani 1 1 d . . . . .
H7A H 0.4071 0.5489 0.3730 0.085 Uiso 1 1 calc R U . . .
H7B H 0.3347 0.4647 0.3698 0.085 Uiso 1 1 calc R U . . .
C8 C 0.4674(2) 0.47096(18) 0.20137(19) 0.0674(5) Uani 1 1 d . . . . .
H8 H 0.3978 0.5477 0.1726 0.081 Uiso 1 1 calc R U . . .
C9 C 0.4861(2) 0.3451(2) 0.1536(2) 0.0720(6) Uani 1 1 d . . . . .
H9A H 0.3993 0.3411 0.1829 0.086 Uiso 1 1 calc R U . . .
H9B H 0.5139 0.3451 0.0649 0.086 Uiso 1 1 calc R U . . .
C10 C 0.6028(3) 0.4751(2) 0.1568(2) 0.0793(6) Uani 1 1 d . . . . .
H10A H 0.5913 0.5553 0.1861 0.095 Uiso 1 1 calc R U . . .
H10B H 0.6328 0.4753 0.0681 0.095 Uiso 1 1 calc R U . . .
H10 H 0.615(7) 0.120(7) 0.4631(18) 0.119 Uiso 0.5 1 d D U P A 1
H10' H 0.654(7) 0.039(4) 0.355(5) 0.119 Uiso 0.5 1 d D U P B -1
O20 O 0.67451(13) 0.88973(12) 0.30361(16) 0.0721(4) Uani 1 1 d D . . . .
C11 C 0.77560(16) 0.77480(15) 0.34292(16) 0.0510(4) Uani 1 1 d . . . . .
H11 H 0.7466 0.7735 0.4325 0.061 Uiso 1 1 calc R U . . .
C12 C 0.78957(16) 0.65199(15) 0.29411(17) 0.0515(4) Uani 1 1 d . . . . .
H12 H 0.7001 0.6516 0.3227 0.062 Uiso 1 1 calc R U . . .
C13 C 0.8386(2) 0.65000(19) 0.15584(18) 0.0643(5) Uani 1 1 d . . . . .
H13A H 0.7725 0.7268 0.1254 0.077 Uiso 1 1 calc R U . . .
H13B H 0.8462 0.5725 0.1249 0.077 Uiso 1 1 calc R U . . .
C14 C 0.9785(2) 0.6491(2) 0.11135(17) 0.0680(5) Uani 1 1 d . . . . .
H14 H 1.0106 0.6471 0.0217 0.082 Uiso 1 1 calc R U . . .
C15 C 0.9628(2) 0.7733(2) 0.15873(19) 0.0682(5) Uani 1 1 d . . . . .
H15A H 1.0505 0.7755 0.1295 0.082 Uiso 1 1 calc R U . . .
H15B H 0.8965 0.8499 0.1282 0.082 Uiso 1 1 calc R U . . .
C16 C 0.91434(17) 0.77636(16) 0.29743(17) 0.0540(4) Uani 1 1 d . . . . .
H16 H 0.9051 0.8560 0.3277 0.065 Uiso 1 1 calc R U . . .
C17 C 0.8937(2) 0.53222(18) 0.34211(19) 0.0633(5) Uani 1 1 d . . . . .
H17A H 0.9022 0.4530 0.3138 0.076 Uiso 1 1 calc R U . . .
H17B H 0.8621 0.5339 0.4308 0.076 Uiso 1 1 calc R U . . .
C18 C 1.03374(18) 0.53144(17) 0.29733(18) 0.0602(5) Uani 1 1 d . . . . .
H18 H 1.1009 0.4538 0.3277 0.072 Uiso 1 1 calc R U . . .
C19 C 1.0177(2) 0.65572(19) 0.3456(2) 0.0658(5) Uani 1 1 d . . . . .
H19A H 0.9860 0.6573 0.4343 0.079 Uiso 1 1 calc R U . . .
H19B H 1.1062 0.6563 0.3194 0.079 Uiso 1 1 calc R U . . .
C20 C 1.0813(2) 0.5298(2) 0.1593(2) 0.0714(5) Uani 1 1 d . . . . .
H20A H 1.0914 0.4508 0.1288 0.086 Uiso 1 1 calc R U . . .
H20B H 1.1705 0.5290 0.1302 0.086 Uiso 1 1 calc R U . . .
H20 H 0.661(6) 0.961(4) 0.338(5) 0.107 Uiso 0.5 1 d D U P C 1
H20' H 0.595(4) 0.884(6) 0.325(5) 0.107 Uiso 0.5 1 d D U P D -1
O30 O 0.42605(14) 0.89570(16) 0.37427(13) 0.0748(4) Uani 1 1 d D . . . .
C21 C 0.32551(19) 1.00743(19) 0.32996(17) 0.0595(5) Uani 1 1 d . . . . .
H21 H 0.3147 1.0874 0.3610 0.071 Uiso 1 1 calc R U . . .
C22 C 0.3733(2) 1.0083(2) 0.19126(18) 0.0626(5) Uani 1 1 d . . . . .
H22 H 0.4628 1.0089 0.1622 0.075 Uiso 1 1 calc R U . . .
C23 C 0.3859(2) 0.8869(2) 0.1425(2) 0.0782(6) Uani 1 1 d . . . . .
H23A H 0.4529 0.8089 0.1709 0.094 Uiso 1 1 calc R U . . .
H23B H 0.4180 0.8857 0.0538 0.094 Uiso 1 1 calc R U . . .
C24 C 0.2471(3) 0.8862(2) 0.1858(2) 0.0799(6) Uani 1 1 d . . . . .
H24 H 0.2553 0.8083 0.1532 0.096 Uiso 1 1 calc R U . . .
C25 C 0.2019(2) 0.8847(2) 0.3250(2) 0.0783(6) Uani 1 1 d . . . . .
H25A H 0.1145 0.8818 0.3548 0.094 Uiso 1 1 calc R U . . .
H25B H 0.2696 0.8067 0.3527 0.094 Uiso 1 1 calc R U . . .
C26 C 0.18683(19) 1.0056(2) 0.37601(17) 0.0624(5) Uani 1 1 d . . . . .
H26 H 0.1566 1.0047 0.4656 0.075 Uiso 1 1 calc R U . . .
C27 C 0.2676(3) 1.1294(2) 0.1487(2) 0.0863(7) Uani 1 1 d . . . . .
H27A H 0.2980 1.1325 0.0601 0.104 Uiso 1 1 calc R U . . .
H27B H 0.2584 1.2070 0.1811 0.104 Uiso 1 1 calc R U . . .
C28 C 0.1278(2) 1.1288(2) 0.1916(2) 0.0815(7) Uani 1 1 d . . . . .
H28 H 0.0597 1.2071 0.1628 0.098 Uiso 1 1 calc R U . . .
C29 C 0.0834(2) 1.1274(2) 0.3311(2) 0.0850(7) Uani 1 1 d . . . . .
H29A H 0.0757 1.2048 0.3624 0.102 Uiso 1 1 calc R U . . .
H29B H -0.0064 1.1295 0.3616 0.102 Uiso 1 1 calc R U . . .
C30 C 0.1435(3) 1.0077(3) 0.1439(3) 0.0908(7) Uani 1 1 d . . . . .
H30A H 0.1721 1.0085 0.0552 0.109 Uiso 1 1 calc R U . . .
H30B H 0.0551 1.0069 0.1716 0.109 Uiso 1 1 calc R U . . .
H30 H 0.504(4) 0.901(7) 0.359(7) 0.136 Uiso 0.5 1 d D U P E 1
H30' H 0.409(8) 0.893(7) 0.456(2) 0.136 Uiso 0.5 1 d D U P F -1


_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
O10 C1 1.435(2) . ?
C1 C6 1.521(2) . ?
C1 C2 1.523(2) . ?
C2 C3 1.514(3) . ?
C2 C7 1.517(2) . ?
C3 C4 1.514(3) . ?
C4 C10 1.503(3) . ?
C4 C5 1.530(3) . ?
C5 C6 1.513(3) . ?
C6 C9 1.521(3) . ?
C7 C8 1.524(3) . ?
C8 C10 1.501(3) . ?
C8 C9 1.528(3) . ?
O20 C11 1.429(2) . ?
C11 C16 1.524(2) . ?
C11 C12 1.525(2) . ?
C12 C13 1.512(3) . ?
C12 C17 1.521(2) . ?
C13 C14 1.523(3) . ?
C14 C20 1.511(3) . ?
C14 C15 1.523(3) . ?
C15 C16 1.516(3) . ?
C16 C19 1.523(2) . ?
C17 C18 1.526(3) . ?
C18 C20 1.509(3) . ?
C18 C19 1.527(3) . ?
O30 C21 1.436(2) . ?
C21 C22 1.517(3) . ?
C21 C26 1.524(3) . ?
C22 C27 1.508(3) . ?
C22 C23 1.517(3) . ?
C23 C24 1.520(3) . ?
C24 C30 1.495(3) . ?
C24 C25 1.522(3) . ?
C25 C26 1.512(3) . ?
C26 C29 1.511(3) . ?
C27 C28 1.530(3) . ?
C28 C30 1.491(3) . ?
C28 C29 1.526(3) . ?

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
O10 C1 C6 109.85(14) . . ?
O10 C1 C2 110.16(14) . . ?
C6 C1 C2 109.95(13) . . ?
C3 C2 C7 109.73(15) . . ?
C3 C2 C1 109.53(14) . . ?
C7 C2 C1 108.32(15) . . ?
C4 C3 C2 109.93(15) . . ?
C10 C4 C3 110.12(18) . . ?
C10 C4 C5 109.08(18) . . ?
C3 C4 C5 108.37(17) . . ?
C6 C5 C4 109.84(15) . . ?
C5 C6 C1 109.51(15) . . ?
C5 C6 C9 109.69(16) . . ?
C1 C6 C9 108.33(16) . . ?
C2 C7 C8 110.24(14) . . ?
C10 C8 C7 109.34(18) . . ?
C10 C8 C9 109.11(18) . . ?
C7 C8 C9 108.23(16) . . ?
C6 C9 C8 110.05(15) . . ?
C8 C10 C4 111.04(15) . . ?
O20 C11 C16 109.99(14) . . ?
O20 C11 C12 110.17(14) . . ?
C16 C11 C12 109.63(13) . . ?
C13 C12 C17 109.84(15) . . ?
C13 C12 C11 109.81(14) . . ?
C17 C12 C11 108.45(14) . . ?
C12 C13 C14 109.62(14) . . ?
C20 C14 C15 109.70(17) . . ?
C20 C14 C13 109.72(16) . . ?
C15 C14 C13 108.59(16) . . ?
C16 C15 C14 109.83(14) . . ?
C15 C16 C11 109.49(14) . . ?
C15 C16 C19 109.83(15) . . ?
C11 C16 C19 108.50(14) . . ?
C12 C17 C18 109.98(13) . . ?
C20 C18 C17 109.18(16) . . ?
C20 C18 C19 109.68(16) . . ?
C17 C18 C19 108.40(15) . . ?
C16 C19 C18 109.83(14) . . ?
C18 C20 C14 110.35(15) . . ?
O30 C21 C22 110.29(15) . . ?
O30 C21 C26 110.18(15) . . ?
C22 C21 C26 110.29(14) . . ?
C27 C22 C21 108.60(18) . . ?
C27 C22 C23 109.55(17) . . ?
C21 C22 C23 108.96(16) . . ?
C22 C23 C24 110.22(16) . . ?
C30 C24 C23 109.5(2) . . ?
C30 C24 C25 109.3(2) . . ?
C23 C24 C25 108.07(17) . . ?
C26 C25 C24 110.33(16) . . ?
C25 C26 C29 109.77(17) . . ?
C25 C26 C21 108.90(16) . . ?
C29 C26 C21 108.23(17) . . ?
C22 C27 C28 110.54(16) . . ?
C30 C28 C29 109.4(2) . . ?
C30 C28 C27 109.2(2) . . ?
C29 C28 C27 107.34(19) . . ?
C26 C29 C28 110.51(16) . . ?
C28 C30 C24 111.74(17) . . ?

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
O10 C1 C2 C3 62.52(18) . . . . ?
C6 C1 C2 C3 -58.69(19) . . . . ?
O10 C1 C2 C7 -177.82(14) . . . . ?
C6 C1 C2 C7 60.97(19) . . . . ?
C7 C2 C3 C4 -58.5(2) . . . . ?
C1 C2 C3 C4 60.3(2) . . . . ?
C2 C3 C4 C10 58.3(2) . . . . ?
C2 C3 C4 C5 -60.9(2) . . . . ?
C10 C4 C5 C6 -59.1(2) . . . . ?
C3 C4 C5 C6 60.8(2) . . . . ?
C4 C5 C6 C1 -59.9(2) . . . . ?
C4 C5 C6 C9 58.9(2) . . . . ?
O10 C1 C6 C5 -62.78(19) . . . . ?
C2 C1 C6 C5 58.61(19) . . . . ?
O10 C1 C6 C9 177.63(14) . . . . ?
C2 C1 C6 C9 -60.98(19) . . . . ?
C3 C2 C7 C8 58.7(2) . . . . ?
C1 C2 C7 C8 -60.8(2) . . . . ?
C2 C7 C8 C10 -58.3(2) . . . . ?
C2 C7 C8 C9 60.4(2) . . . . ?
C5 C6 C9 C8 -58.8(2) . . . . ?
C1 C6 C9 C8 60.7(2) . . . . ?
C10 C8 C9 C6 58.6(2) . . . . ?
C7 C8 C9 C6 -60.3(2) . . . . ?
C7 C8 C10 C4 58.4(2) . . . . ?
C9 C8 C10 C4 -59.8(2) . . . . ?
C3 C4 C10 C8 -58.8(2) . . . . ?
C5 C4 C10 C8 60.0(2) . . . . ?
O20 C11 C12 C13 62.19(18) . . . . ?
C16 C11 C12 C13 -58.98(18) . . . . ?
O20 C11 C12 C17 -177.78(14) . . . . ?
C16 C11 C12 C17 61.05(18) . . . . ?
C17 C12 C13 C14 -58.96(19) . . . . ?
C11 C12 C13 C14 60.22(19) . . . . ?
C12 C13 C14 C20 59.2(2) . . . . ?
C12 C13 C14 C15 -60.7(2) . . . . ?
C20 C14 C15 C16 -59.1(2) . . . . ?
C13 C14 C15 C16 60.8(2) . . . . ?
C14 C15 C16 C11 -60.11(19) . . . . ?
C14 C15 C16 C19 58.9(2) . . . . ?
O20 C11 C16 C15 -62.57(18) . . . . ?
C12 C11 C16 C15 58.71(18) . . . . ?
O20 C11 C16 C19 177.58(14) . . . . ?
C12 C11 C16 C19 -61.14(18) . . . . ?
C13 C12 C17 C18 59.15(19) . . . . ?
C11 C12 C17 C18 -60.86(19) . . . . ?
C12 C17 C18 C20 -58.9(2) . . . . ?
C12 C17 C18 C19 60.5(2) . . . . ?
C15 C16 C19 C18 -58.7(2) . . . . ?
C11 C16 C19 C18 60.9(2) . . . . ?
C20 C18 C19 C16 58.6(2) . . . . ?
C17 C18 C19 C16 -60.5(2) . . . . ?
C17 C18 C20 C14 59.4(2) . . . . ?
C19 C18 C20 C14 -59.2(2) . . . . ?
C15 C14 C20 C18 59.4(2) . . . . ?
C13 C14 C20 C18 -59.8(2) . . . . ?
O30 C21 C22 C27 -177.97(16) . . . . ?
C26 C21 C22 C27 60.1(2) . . . . ?
O30 C21 C22 C23 62.8(2) . . . . ?
C26 C21 C22 C23 -59.2(2) . . . . ?
C27 C22 C23 C24 -58.4(2) . . . . ?
C21 C22 C23 C24 60.3(2) . . . . ?
C22 C23 C24 C30 58.2(2) . . . . ?
C22 C23 C24 C25 -60.7(2) . . . . ?
C30 C24 C25 C26 -58.3(2) . . . . ?
C23 C24 C25 C26 60.8(2) . . . . ?
C24 C25 C26 C29 58.2(2) . . . . ?
C24 C25 C26 C21 -60.1(2) . . . . ?
O30 C21 C26 C25 -62.8(2) . . . . ?
C22 C21 C26 C25 59.2(2) . . . . ?
O30 C21 C26 C29 177.89(16) . . . . ?
C22 C21 C26 C29 -60.1(2) . . . . ?
C21 C22 C27 C28 -60.7(2) . . . . ?
C23 C22 C27 C28 58.2(3) . . . . ?
C22 C27 C28 C30 -57.9(3) . . . . ?
C22 C27 C28 C29 60.6(2) . . . . ?
C25 C26 C29 C28 -57.8(2) . . . . ?
C21 C26 C29 C28 60.9(2) . . . . ?
C30 C28 C29 C26 57.5(3) . . . . ?
C27 C28 C29 C26 -60.8(2) . . . . ?
C29 C28 C30 C24 -58.7(3) . . . . ?
C27 C28 C30 C24 58.5(3) . . . . ?
C23 C24 C30 C28 -59.0(3) . . . . ?
C25 C24 C30 C28 59.1(3) . . . . ?

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O10 H10 O30 0.90(2) 1.79(2) 2.684(2) 170(7) 2_666 yes
O10 H10' O20 0.89(5) 1.79(6) 2.688(2) 179(9) 1_545 yes
O20 H20 O10 0.89(5) 1.81(5) 2.688(2) 170(5) 1_565 yes
O20 H20' O30 0.90(6) 1.79(6) 2.686(3) 172(5) . yes
O30 H30 O20 0.89(7) 1.81(7) 2.686(3) 169(8) . yes
O30 H30' O10 0.90(3) 1.79(2) 2.684(2) 173(10) 2_666 yes

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_Ada2Me2ol_Pbcn345K
_database_code_depnum_ccdc_archive 'CCDC 2129552'
loop_
_audit_author_name
_audit_author_address
'Ph. Negrier'
;Universite de Bordeaux
France
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT110_Ada2Me2ol_Pbcn345K  
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: Powder diffraction has shown supplementary peaks impossible with half lattice and Pcca group
;
_vrf_PLAT112_Ada2Me2ol_Pbcn345K  
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       a/2        100 %Fit
RESPONSE: Powder diffraction has shown supplementary peaks impossible with half lattice and Pcca group
;
_vrf_PLAT113_Ada2Me2ol_Pbcn345K  
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       Pcca Check
RESPONSE: Powder diffraction has shown supplementary peaks impossible with half lattice and Pcca group
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 O'
_chemical_formula_sum            'C11 H18 O'
_chemical_formula_weight         166.25

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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.
;

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,y,1/2-z
5 -x,-y,-z
6 1/2+x,1/2+y,1/2-z
7 1/2-x,1/2+y,z
8 x,-y,1/2+z

_cell_length_a                   18.9657(5)
_cell_length_b                   9.2178(2)
_cell_length_c                   21.3293(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3728.83(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    345(2)
_cell_measurement_reflns_used    4525
_cell_measurement_theta_min      4.1610
_cell_measurement_theta_max      73.1750

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.560
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67395
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      345(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'FRX Rotating Anode'
_diffrn_measurement_device_type  'Rigaku PILATUS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            8719
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.145
_diffrn_reflns_theta_max         73.771
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             3461
_reflns_number_gt                2830
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0960P)²+0.4329P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00084(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3461
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1707
_refine_ls_wR_factor_gt          0.1607
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.19429(6) 0.11148(11) 0.47575(5) 0.0572(3) Uani 1 1 d . . . . .
C1 C 0.14273(7) 0.02385(13) 0.44346(6) 0.0416(3) Uani 1 1 d . . . . .
C2 C 0.09157(7) 0.12784(14) 0.41102(6) 0.0477(4) Uani 1 1 d . . . . .
H2 H 0.0670 0.1857 0.4427 0.057 Uiso 1 1 calc R U . . .
C3 C 0.03728(7) 0.04169(18) 0.37259(8) 0.0574(4) Uani 1 1 d . . . . .
H3A H 0.0107 -0.0216 0.4002 0.069 Uiso 1 1 calc R U . . .
H3B H 0.0045 0.1081 0.3527 0.069 Uiso 1 1 calc R U . . .
C4 C 0.07456(9) -0.04839(17) 0.32282(7) 0.0596(4) Uani 1 1 d . . . . .
H4 H 0.0397 -0.1039 0.2988 0.072 Uiso 1 1 calc R U . . .
C5 C 0.12613(9) -0.15255(16) 0.35454(7) 0.0581(4) Uani 1 1 d . . . . .
H5A H 0.1005 -0.2183 0.3818 0.070 Uiso 1 1 calc R U . . .
H5B H 0.1504 -0.2098 0.3230 0.070 Uiso 1 1 calc R U . . .
C6 C 0.17974(7) -0.06629(14) 0.39281(6) 0.0444(3) Uani 1 1 d . . . . .
H6 H 0.2130 -0.1334 0.4127 0.053 Uiso 1 1 calc R U . . .
C7 C 0.21991(8) 0.03454(18) 0.34843(7) 0.0589(4) Uani 1 1 d . . . . .
H7A H 0.2548 0.0892 0.3718 0.071 Uiso 1 1 calc R U . . .
H7B H 0.2443 -0.0224 0.3169 0.071 Uiso 1 1 calc R U . . .
C8 C 0.16862(8) 0.13873(19) 0.31666(7) 0.0615(4) Uani 1 1 d . . . . .
H8 H 0.1947 0.2034 0.2885 0.074 Uiso 1 1 calc R U . . .
C9 C 0.11442(10) 0.0528(2) 0.27901(7) 0.0688(5) Uani 1 1 d . . . . .
H9A H 0.0817 0.1188 0.2588 0.083 Uiso 1 1 calc R U . . .
H9B H 0.1380 -0.0032 0.2467 0.083 Uiso 1 1 calc R U . . .
C10 C 0.13124(8) 0.22867(15) 0.36675(7) 0.0563(4) Uani 1 1 d . . . . .
H10A H 0.1655 0.2850 0.3901 0.068 Uiso 1 1 calc R U . . .
H10B H 0.0985 0.2954 0.3470 0.068 Uiso 1 1 calc R U . . .
C11 C 0.10718(10) -0.0684(2) 0.49339(7) 0.0671(5) Uani 1 1 d . . . . .
H11A H 0.1417 -0.1291 0.5133 0.101 Uiso 1 1 calc R U . . .
H11B H 0.0716 -0.1279 0.4743 0.101 Uiso 1 1 calc R U . . .
H11C H 0.0858 -0.0064 0.5241 0.101 Uiso 1 1 calc R U . . .
H1 H 0.2225(12) 0.053(3) 0.4911(11) 0.101 Uiso 1 1 d . U . . .
O21 O 0.29153(6) -0.11122(11) 0.53351(5) 0.0530(3) Uani 1 1 d . . . . .
C21 C 0.35298(7) -0.04059(13) 0.55873(6) 0.0408(3) Uani 1 1 d . . . . .
C22 C 0.32524(7) 0.06722(14) 0.60735(6) 0.0456(3) Uani 1 1 d . . . . .
H22 H 0.2941 0.1374 0.5867 0.055 Uiso 1 1 calc R U . . .
C23 C 0.28368(8) -0.01460(19) 0.65778(7) 0.0588(4) Uani 1 1 d . . . . .
H23A H 0.2650 0.0537 0.6881 0.071 Uiso 1 1 calc R U . . .
H23B H 0.2443 -0.0652 0.6386 0.071 Uiso 1 1 calc R U . . .
C24 C 0.33167(8) -0.12316(19) 0.69069(7) 0.0607(4) Uani 1 1 d . . . . .
H24 H 0.3046 -0.1758 0.7225 0.073 Uiso 1 1 calc R U . . .
C25 C 0.36055(8) -0.23041(16) 0.64270(7) 0.0581(4) Uani 1 1 d . . . . .
H25A H 0.3913 -0.2996 0.6633 0.070 Uiso 1 1 calc R U . . .
H25B H 0.3220 -0.2834 0.6235 0.070 Uiso 1 1 calc R U . . .
C26 C 0.40141(7) -0.14850(15) 0.59260(6) 0.0476(4) Uani 1 1 d . . . . .
H26 H 0.4205 -0.2177 0.5621 0.057 Uiso 1 1 calc R U . . .
C27 C 0.46268(7) -0.06814(19) 0.62472(8) 0.0595(4) Uani 1 1 d . . . . .
H27A H 0.4931 -0.1375 0.6456 0.071 Uiso 1 1 calc R U . . .
H27B H 0.4904 -0.0172 0.5935 0.071 Uiso 1 1 calc R U . . .
C28 C 0.43396(8) 0.03959(18) 0.67241(7) 0.0597(4) Uani 1 1 d . . . . .
H28 H 0.4731 0.0915 0.6923 0.072 Uiso 1 1 calc R U . . .
C29 C 0.39236(9) -0.0429(2) 0.72205(7) 0.0668(5) Uani 1 1 d . . . . .
H29A H 0.4229 -0.1115 0.7432 0.080 Uiso 1 1 calc R U . . .
H29B H 0.3741 0.0244 0.7530 0.080 Uiso 1 1 calc R U . . .
C30 C 0.38579(9) 0.14770(17) 0.63895(7) 0.0603(4) Uani 1 1 d . . . . .
H30A H 0.3671 0.2168 0.6690 0.072 Uiso 1 1 calc R U . . .
H30B H 0.4126 0.2009 0.6078 0.072 Uiso 1 1 calc R U . . .
C31 C 0.38956(10) 0.03217(19) 0.50341(7) 0.0641(5) Uani 1 1 d . . . . .
H31A H 0.4053 -0.0406 0.4744 0.096 Uiso 1 1 calc R U . . .
H31B H 0.4294 0.0866 0.5182 0.096 Uiso 1 1 calc R U . . .
H31C H 0.3571 0.0963 0.4828 0.096 Uiso 1 1 calc R U . . .
H21 H 0.3037(11) -0.191(3) 0.5131(10) 0.096 Uiso 1 1 d . 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_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4433(17) . . yes
O1 H1 0.83(3) . . no
O21 C21 1.4393(17) . . yes
O21 H21 0.89(3) . . no
C1 C11 1.521(2) . . no
C1 C6 1.5330(18) . . no
C1 C2 1.5294(18) . . no
C2 C10 1.524(2) . . no
C2 C3 1.537(2) . . no
C3 C4 1.522(2) . . no
C4 C9 1.521(2) . . no
C4 C5 1.529(2) . . no
C5 C6 1.527(2) . . no
C6 C7 1.530(2) . . no
C7 C8 1.526(2) . . no
C8 C10 1.527(2) . . no
C8 C9 1.526(2) . . no
C2 H2 0.9800 . . no
C3 H3B 0.9700 . . no
C3 H3A 0.9700 . . no
C4 H4 0.9800 . . no
C5 H5B 0.9700 . . no
C5 H5A 0.9700 . . no
C6 H6 0.9800 . . no
C7 H7B 0.9700 . . no
C7 H7A 0.9700 . . no
C8 H8 0.9800 . . no
C9 H9B 0.9700 . . no
C9 H9A 0.9700 . . no
C10 H10A 0.9700 . . no
C10 H10B 0.9700 . . no
C11 H11B 0.9600 . . no
C11 H11A 0.9600 . . no
C11 H11C 0.9600 . . no
C21 C26 1.5346(18) . . no
C21 C31 1.524(2) . . no
C21 C22 1.5296(18) . . no
C22 C30 1.524(2) . . no
C22 C23 1.532(2) . . no
C23 C24 1.524(2) . . no
C24 C29 1.523(2) . . no
C24 C25 1.525(2) . . no
C25 C26 1.521(2) . . no
C26 C27 1.539(2) . . no
C27 C28 1.522(2) . . no
C28 C29 1.524(2) . . no
C28 C30 1.529(2) . . no
C22 H22 0.9800 . . no
C23 H23A 0.9700 . . no
C23 H23B 0.9700 . . no
C24 H24 0.9800 . . no
C25 H25A 0.9700 . . no
C25 H25B 0.9700 . . no
C26 H26 0.9800 . . no
C27 H27A 0.9700 . . no
C27 H27B 0.9700 . . no
C28 H28 0.9800 . . no
C29 H29A 0.9700 . . no
C29 H29B 0.9700 . . no
C30 H30A 0.9700 . . no
C30 H30B 0.9700 . . no
C31 H31A 0.9600 . . no
C31 H31B 0.9600 . . no
C31 H31C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 105.2(18) . . . no
C21 O21 H21 110.4(14) . . . no
O1 C1 C2 107.16(10) . . . yes
C2 C1 C6 108.14(10) . . . no
C2 C1 C11 112.71(12) . . . no
O1 C1 C11 106.21(11) . . . yes
C6 C1 C11 113.17(11) . . . no
O1 C1 C6 109.23(11) . . . yes
C1 C2 C10 110.45(11) . . . no
C1 C2 C3 110.03(11) . . . no
C3 C2 C10 108.39(11) . . . no
C2 C3 C4 110.04(11) . . . no
C3 C4 C9 108.95(13) . . . no
C3 C4 C5 109.34(12) . . . no
C5 C4 C9 109.82(14) . . . no
C4 C5 C6 109.61(12) . . . no
C1 C6 C7 109.56(11) . . . no
C1 C6 C5 110.73(11) . . . no
C5 C6 C7 108.49(11) . . . no
C6 C7 C8 109.86(12) . . . no
C7 C8 C9 109.66(14) . . . no
C7 C8 C10 109.09(12) . . . no
C9 C8 C10 109.71(13) . . . no
C4 C9 C8 109.25(12) . . . no
C2 C10 C8 109.37(12) . . . no
C3 C2 H2 109.00 . . . no
C10 C2 H2 109.00 . . . no
C1 C2 H2 109.00 . . . no
C2 C3 H3B 110.00 . . . no
C4 C3 H3A 110.00 . . . no
C4 C3 H3B 110.00 . . . no
H3A C3 H3B 108.00 . . . no
C2 C3 H3A 110.00 . . . no
C3 C4 H4 110.00 . . . no
C5 C4 H4 110.00 . . . no
C9 C4 H4 110.00 . . . no
C4 C5 H5A 110.00 . . . no
C4 C5 H5B 110.00 . . . no
C6 C5 H5B 110.00 . . . no
H5A C5 H5B 108.00 . . . no
C6 C5 H5A 110.00 . . . no
C1 C6 H6 109.00 . . . no
C7 C6 H6 109.00 . . . no
C5 C6 H6 109.00 . . . no
C6 C7 H7A 110.00 . . . no
C8 C7 H7A 110.00 . . . no
C8 C7 H7B 110.00 . . . no
H7A C7 H7B 108.00 . . . no
C6 C7 H7B 110.00 . . . no
C7 C8 H8 109.00 . . . no
C10 C8 H8 109.00 . . . no
C9 C8 H8 109.00 . . . no
C4 C9 H9A 110.00 . . . no
C8 C9 H9A 110.00 . . . no
C8 C9 H9B 110.00 . . . no
H9A C9 H9B 108.00 . . . no
C4 C9 H9B 110.00 . . . no
C2 C10 H10B 110.00 . . . no
C8 C10 H10A 110.00 . . . no
C2 C10 H10A 110.00 . . . no
H10A C10 H10B 108.00 . . . no
C8 C10 H10B 110.00 . . . no
C1 C11 H11B 110.00 . . . no
C1 C11 H11C 109.00 . . . no
H11A C11 H11B 110.00 . . . no
H11A C11 H11C 109.00 . . . no
H11B C11 H11C 109.00 . . . no
C1 C11 H11A 109.00 . . . no
O21 C21 C22 105.59(10) . . . yes
O21 C21 C31 106.16(11) . . . yes
C22 C21 C26 107.93(10) . . . no
C22 C21 C31 113.30(11) . . . no
C26 C21 C31 112.16(12) . . . no
O21 C21 C26 111.56(10) . . . yes
C21 C22 C23 109.46(11) . . . no
C21 C22 C30 110.91(11) . . . no
C23 C22 C30 108.47(11) . . . no
C22 C23 C24 109.84(12) . . . no
C23 C24 C29 109.55(14) . . . no
C25 C24 C29 109.77(13) . . . no
C23 C24 C25 109.33(12) . . . no
C24 C25 C26 109.44(12) . . . no
C21 C26 C25 110.34(11) . . . no
C21 C26 C27 110.46(12) . . . no
C25 C26 C27 108.12(11) . . . no
C26 C27 C28 109.95(11) . . . no
C27 C28 C29 108.91(14) . . . no
C27 C28 C30 109.09(12) . . . no
C29 C28 C30 109.89(13) . . . no
C24 C29 C28 109.18(12) . . . no
C22 C30 C28 109.84(12) . . . no
C21 C22 H22 109.00 . . . no
C23 C22 H22 109.00 . . . no
C30 C22 H22 109.00 . . . no
C22 C23 H23A 110.00 . . . no
C22 C23 H23B 110.00 . . . no
C24 C23 H23A 110.00 . . . no
C24 C23 H23B 110.00 . . . no
H23A C23 H23B 108.00 . . . no
C23 C24 H24 109.00 . . . no
C25 C24 H24 109.00 . . . no
C29 C24 H24 109.00 . . . no
C24 C25 H25A 110.00 . . . no
C24 C25 H25B 110.00 . . . no
C26 C25 H25A 110.00 . . . no
C26 C25 H25B 110.00 . . . no
H25A C25 H25B 108.00 . . . no
C21 C26 H26 109.00 . . . no
C25 C26 H26 109.00 . . . no
C27 C26 H26 109.00 . . . no
C26 C27 H27A 110.00 . . . no
C26 C27 H27B 110.00 . . . no
C28 C27 H27A 110.00 . . . no
C28 C27 H27B 110.00 . . . no
H27A C27 H27B 108.00 . . . no
C27 C28 H28 110.00 . . . no
C29 C28 H28 110.00 . . . no
C30 C28 H28 110.00 . . . no
C24 C29 H29A 110.00 . . . no
C24 C29 H29B 110.00 . . . no
C28 C29 H29A 110.00 . . . no
C28 C29 H29B 110.00 . . . no
H29A C29 H29B 108.00 . . . no
C22 C30 H30A 110.00 . . . no
C22 C30 H30B 110.00 . . . no
C28 C30 H30A 110.00 . . . no
C28 C30 H30B 110.00 . . . no
H30A C30 H30B 108.00 . . . no
C21 C31 H31A 109.00 . . . no
C21 C31 H31B 109.00 . . . no
C21 C31 H31C 109.00 . . . no
H31A C31 H31B 109.00 . . . no
H31A C31 H31C 110.00 . . . no
H31B C31 H31C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 176.95(11) . . . . no
O1 C1 C2 C10 57.33(13) . . . . no
C6 C1 C2 C3 59.31(14) . . . . no
C6 C1 C2 C10 -60.31(13) . . . . no
C11 C1 C2 C3 -66.57(15) . . . . no
C11 C1 C2 C10 173.81(12) . . . . no
O1 C1 C6 C5 -176.02(10) . . . . no
O1 C1 C6 C7 -56.39(13) . . . . no
C2 C1 C6 C5 -59.72(13) . . . . no
C2 C1 C6 C7 59.91(14) . . . . no
C11 C1 C6 C5 65.88(15) . . . . no
C11 C1 C6 C7 -174.49(12) . . . . no
C1 C2 C3 C4 -60.22(15) . . . . no
C10 C2 C3 C4 60.65(15) . . . . no
C1 C2 C10 C8 60.58(14) . . . . no
C3 C2 C10 C8 -60.03(15) . . . . no
C2 C3 C4 C5 59.22(16) . . . . no
C2 C3 C4 C9 -60.81(17) . . . . no
C3 C4 C5 C6 -58.93(16) . . . . no
C9 C4 C5 C6 60.57(16) . . . . no
C3 C4 C9 C8 60.16(17) . . . . no
C5 C4 C9 C8 -59.58(17) . . . . no
C4 C5 C6 C1 60.02(15) . . . . no
C4 C5 C6 C7 -60.25(15) . . . . no
C1 C6 C7 C8 -60.69(15) . . . . no
C5 C6 C7 C8 60.30(15) . . . . no
C6 C7 C8 C9 -60.25(16) . . . . no
C6 C7 C8 C10 59.92(16) . . . . no
C7 C8 C9 C4 59.38(17) . . . . no
C10 C8 C9 C4 -60.42(18) . . . . no
C7 C8 C10 C2 -59.47(16) . . . . no
C9 C8 C10 C2 60.67(16) . . . . no
O21 C21 C22 C23 59.10(13) . . . . no
O21 C21 C22 C30 178.74(10) . . . . no
C26 C21 C22 C23 -60.32(14) . . . . no
C26 C21 C22 C30 59.32(14) . . . . no
C31 C21 C22 C23 174.86(12) . . . . no
C31 C21 C22 C30 -65.49(15) . . . . no
O21 C21 C26 C25 -54.83(14) . . . . no
O21 C21 C26 C27 -174.32(11) . . . . no
C22 C21 C26 C25 60.74(14) . . . . no
C22 C21 C26 C27 -58.75(14) . . . . no
C31 C21 C26 C25 -173.77(12) . . . . no
C31 C21 C26 C27 66.74(15) . . . . no
C21 C22 C23 C24 60.79(15) . . . . no
C30 C22 C23 C24 -60.34(16) . . . . no
C21 C22 C30 C28 -60.43(15) . . . . no
C23 C22 C30 C28 59.81(15) . . . . no
C22 C23 C24 C25 -59.59(16) . . . . no
C22 C23 C24 C29 60.74(16) . . . . no
C23 C24 C25 C26 59.21(16) . . . . no
C29 C24 C25 C26 -60.99(16) . . . . no
C23 C24 C29 C28 -59.74(17) . . . . no
C25 C24 C29 C28 60.32(17) . . . . no
C24 C25 C26 C21 -60.53(15) . . . . no
C24 C25 C26 C27 60.36(15) . . . . no
C21 C26 C27 C28 59.90(16) . . . . no
C25 C26 C27 C28 -60.93(16) . . . . no
C26 C27 C28 C29 60.90(16) . . . . no
C26 C27 C28 C30 -59.04(17) . . . . no
C27 C28 C29 C24 -60.03(17) . . . . no
C30 C28 C29 C24 59.42(17) . . . . no
C27 C28 C30 C22 59.26(16) . . . . no
C29 C28 C30 C22 -60.08(16) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 O21 3.0221(15) . . no
O1 O21 2.8502(15) . 7_555 no
O21 O1 2.8502(15) . 7_545 no
O21 O1 3.0221(15) . . no
O1 H7A 2.5100 . . no
O1 H10A 2.4900 . . no
O1 H21 1.99(3) . 7_555 no
O21 H25B 2.5600 . . no
O21 H11A 2.8800 . . no
O21 H23B 2.4500 . . no
O21 H1 2.20(3) . . no
C1 C9 3.559(2) . . no
C3 C7 3.503(2) . . no
C5 C10 3.525(2) . . no
C7 C3 3.503(2) . . no
C9 C1 3.559(2) . . no
C10 C5 3.525(2) . . no
C21 C29 3.563(2) . . no
C23 C27 3.502(2) . . no
C25 C30 3.519(2) . . no
C27 C23 3.502(2) . . no
C29 C21 3.563(2) . . no
C30 C25 3.519(2) . . no
C3 H11B 2.7500 . . no
C5 H11B 2.7700 . . no
C7 H1 3.05(2) . . no
C11 H3A 2.7400 . . no
C11 H5A 2.7600 . . no
C21 H1 2.99(2) . . no
C23 H25B 3.0200 . 7_555 no
C25 H21 2.99(2) . . no
C27 H31B 2.7600 . . no
C30 H31B 2.7600 . . no
C31 H27B 3.0800 . 5_656 no
C31 H27B 2.7500 . . no
C31 H30B 2.7500 . . no
H1 O21 2.20(3) . . no
H1 H31C 2.5900 . . no
H1 H21 2.46(4) . 7_555 no
H1 H22 2.5700 . . no
H1 C21 2.99(2) . . no
H1 H6 2.4000 . . no
H1 C7 3.05(2) . . no
H1 H11A 2.3200 . . no
H2 H11C 2.5100 . . no
H3A H5A 2.5200 . . no
H3A C11 2.7400 . . no
H3A H11C 2.4500 . 5_556 no
H3A H11B 2.1900 . . no
H3B H9A 2.4800 . . no
H3B H10B 2.4800 . . no
H4 H4 2.5700 . 4_555 no
H5A H3A 2.5200 . . no
H5A C11 2.7600 . . no
H5A H11B 2.2100 . . no
H5A H27A 2.5000 . 3_446 no
H5B H24 2.5400 . 2_544 no
H5B H7B 2.4800 . . no
H5B H9B 2.5200 . . no
H6 H11A 2.5400 . . no
H6 H10A 2.4700 . 7_545 no
H6 H1 2.4000 . . no
H7A O1 2.5100 . . no
H7A H10A 2.5100 . . no
H7B H5B 2.4800 . . no
H7B H9B 2.5200 . . no
H8 H24 2.5300 . 8_554 no
H9A H3B 2.4800 . . no
H9A H10B 2.5100 . . no
H9B H5B 2.5200 . . no
H9B H7B 2.5200 . . no
H10A H6 2.4700 . 7_555 no
H10A O1 2.4900 . . no
H10A H7A 2.5100 . . no
H10B H3B 2.4800 . . no
H10B H9A 2.5100 . . no
H11A H1 2.3200 . . no
H11A O21 2.8800 . . no
H11A H6 2.5400 . . no
H11B C3 2.7500 . . no
H11B C5 2.7700 . . no
H11B H5A 2.2100 . . no
H11B H3A 2.1900 . . no
H11C H3A 2.4500 . 5_556 no
H11C H2 2.5100 . . no
H21 C25 2.99(2) . . no
H21 H25B 2.5300 . . no
H21 H26 2.4600 . . no
H21 H31A 2.5100 . . no
H21 O1 1.99(3) . 7_545 no
H21 H1 2.46(4) . 7_545 no
H22 H1 2.5700 . . no
H22 H31C 2.5500 . . no
H22 H25B 2.4500 . 7_555 no
H23A H29B 2.5000 . . no
H23A H30A 2.4900 . . no
H23B O21 2.4500 . . no
H23B H25B 2.5100 . . no
H24 H5B 2.5400 . 2_545 no
H24 H8 2.5300 . 8_555 no
H25A H27A 2.4700 . . no
H25A H29A 2.5000 . . no
H25B O21 2.5600 . . no
H25B H21 2.5300 . . no
H25B H23B 2.5100 . . no
H25B C23 3.0200 . 7_545 no
H25B H22 2.4500 . 7_545 no
H26 H21 2.4600 . . no
H26 H31A 2.5000 . . no
H27A H25A 2.4700 . . no
H27A H29A 2.4800 . . no
H27A H5A 2.5000 . 3_546 no
H27B C31 2.7500 . . no
H27B H30B 2.5100 . . no
H27B H31B 2.2000 . . no
H27B C31 3.0800 . 5_656 no
H27B H31A 2.5100 . 5_656 no
H29A H25A 2.5000 . . no
H29A H27A 2.4800 . . no
H29B H23A 2.5000 . . no
H29B H30A 2.5200 . . no
H30A H23A 2.4900 . . no
H30A H29B 2.5200 . . no
H30B C31 2.7500 . . no
H30B H27B 2.5100 . . no
H30B H31B 2.2100 . . no
H31A H21 2.5100 . . no
H31A H26 2.5000 . . no
H31A H27B 2.5100 . 5_656 no
H31B C27 2.7600 . . no
H31B C30 2.7600 . . no
H31B H27B 2.2000 . . no
H31B H30B 2.2100 . . no
H31C H1 2.5900 . . no
H31C H22 2.5500 . . no

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1 O21 0.83(3) 2.20(3) 3.0221(15) 176(2) . yes
O21 H21 O1 0.89(3) 1.99(3) 2.8502(15) 164(2) 7_545 yes
C7 H7A O1 0.9700 2.5100 2.8485(18) 101.00 . yes
C10 H10A O1 0.9700 2.4900 2.8288(18) 100.00 . yes
C23 H23B O21 0.9700 2.4500 2.8002(19) 101.00 . yes
C25 H25B O21 0.9700 2.5600 2.8887(18) 100.00 . yes


_refine_diff_density_max         0.133
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.041



####################################################################### 
# 
# 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_Ada2Me2ol_Pbcn293K
_database_code_depnum_ccdc_archive 'CCDC 2129551'
loop_
_audit_author_name
_audit_author_address
'Ph. Negrier'
;Universite de Bordeaux
France
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT110_Ada2Me2ol_Pbcn293K  
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: Powder diffraction has shown supplementary peaks impossible with half lattice and Pcca group
;
_vrf_PLAT112_Ada2Me2ol_Pbcn293K  
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       a/2        100 %Fit
RESPONSE: Powder diffraction has shown supplementary peaks impossible with half lattice and Pcca group
;
_vrf_PLAT113_Ada2Me2ol_Pbcn293K  
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       Pcca Check
RESPONSE: Powder diffraction has shown supplementary peaks impossible with half lattice and Pcca group
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 O'
_chemical_formula_sum            'C11 H18 O'
_chemical_formula_weight         166.25

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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.
;

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,y,1/2-z
5 -x,-y,-z
6 1/2+x,1/2+y,1/2-z
7 1/2-x,1/2+y,z
8 x,-y,1/2+z

_cell_length_a                   18.90920(10)
_cell_length_b                   9.17610(10)
_cell_length_c                   21.2981(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3695.49(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      4.1330
_cell_measurement_theta_max      73.2720

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.565
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'FRX Rotating Anode'
_diffrn_measurement_device_type  'Rigaku PILATUS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            15637
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.151
_diffrn_reflns_theta_max         73.704
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3696
_reflns_number_gt                3412
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+0.5820P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00107(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3696
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
H21 H 0.2219(8) 0.4468(18) 0.4925(7) 0.077(5) Uiso 1 1 d . . . . .
H1 H 0.1969(8) 0.8083(19) 0.0154(7) 0.072(4) Uiso 1 1 d . . . . .
O1 O 0.20893(4) 0.88781(8) 0.03384(3) 0.0406(2) Uani 1 1 d . . . . .
C1 C 0.14695(5) 0.95873(9) 0.05867(4) 0.0315(2) Uani 1 1 d . . . . .
C2 C 0.17466(5) 1.06809(10) 0.10738(4) 0.0353(2) Uani 1 1 d . . . . .
H2 H 0.2057 1.1386 0.0866 0.042 Uiso 1 1 calc R U . . .
C3 C 0.21656(5) 0.98666(13) 0.15810(5) 0.0452(3) Uani 1 1 d . . . . .
H3A H 0.2562 0.9361 0.1390 0.054 Uiso 1 1 calc R U . . .
H3B H 0.2351 1.0557 0.1884 0.054 Uiso 1 1 calc R U . . .
C4 C 0.16848(5) 0.87701(13) 0.19125(5) 0.0465(3) Uani 1 1 d . . . . .
H4 H 0.1957 0.8247 0.2233 0.056 Uiso 1 1 calc R U . . .
C5 C 0.13968(6) 0.76827(11) 0.14332(5) 0.0455(3) Uani 1 1 d . . . . .
H5A H 0.1785 0.7151 0.1242 0.055 Uiso 1 1 calc R U . . .
H5B H 0.1089 0.6987 0.1641 0.055 Uiso 1 1 calc R U . . .
C6 C 0.09839(5) 0.85010(10) 0.09281(5) 0.0368(2) Uani 1 1 d . . . . .
H6 H 0.0795 0.7801 0.0624 0.044 Uiso 1 1 calc R U . . .
C7 C 0.03670(5) 0.93071(13) 0.12466(5) 0.0462(3) Uani 1 1 d . . . . .
H7A H 0.0089 0.9814 0.0932 0.055 Uiso 1 1 calc R U . . .
H7B H 0.0062 0.8610 0.1456 0.055 Uiso 1 1 calc R U . . .
C8 C 0.06527(6) 1.03994(12) 0.17245(5) 0.0459(3) Uani 1 1 d . . . . .
H8 H 0.0258 1.0918 0.1922 0.055 Uiso 1 1 calc R U . . .
C9 C 0.10729(6) 0.95791(14) 0.22257(5) 0.0518(3) Uani 1 1 d . . . . .
H9A H 0.1255 1.0261 0.2534 0.062 Uiso 1 1 calc R U . . .
H9B H 0.0767 0.8890 0.2440 0.062 Uiso 1 1 calc R U . . .
C10 C 0.11341(6) 1.14912(11) 0.13887(5) 0.0465(3) Uani 1 1 d . . . . .
H10A H 0.1318 1.2189 0.1689 0.056 Uiso 1 1 calc R U . . .
H10B H 0.0865 1.2020 0.1075 0.056 Uiso 1 1 calc R U . . .
C11 C 0.11005(6) 1.03097(13) 0.00317(5) 0.0493(3) Uani 1 1 d . . . . .
H11A H 0.1426 1.0950 -0.0178 0.074 Uiso 1 1 calc R U . . .
H11B H 0.0702 1.0860 0.0180 0.074 Uiso 1 1 calc R U . . .
H11C H 0.0942 0.9575 -0.0256 0.074 Uiso 1 1 calc R U . . .
O21 O 0.19461(4) 0.38932(8) 0.47638(3) 0.0444(2) Uani 1 1 d . . . . .
C21 C 0.14280(5) 0.47738(10) 0.44393(4) 0.0323(2) Uani 1 1 d . . . . .
C22 C 0.18034(5) 0.56729(10) 0.39288(4) 0.0341(2) Uani 1 1 d . . . . .
H22 H 0.2137 0.6347 0.4127 0.041 Uiso 1 1 calc R U . . .
C23 C 0.22066(5) 0.46510(13) 0.34851(5) 0.0455(3) Uani 1 1 d . . . . .
H23A H 0.2451 0.5219 0.3168 0.055 Uiso 1 1 calc R U . . .
H23B H 0.2557 0.4104 0.3720 0.055 Uiso 1 1 calc R U . . .
C24 C 0.16892(6) 0.35987(13) 0.31689(5) 0.0477(3) Uani 1 1 d . . . . .
H24 H 0.1950 0.2944 0.2888 0.057 Uiso 1 1 calc R U . . .
C25 C 0.13109(6) 0.27018(11) 0.36733(5) 0.0437(3) Uani 1 1 d . . . . .
H25A H 0.0982 0.2031 0.3477 0.052 Uiso 1 1 calc R U . . .
H25B H 0.1654 0.2138 0.3910 0.052 Uiso 1 1 calc R U . . .
C26 C 0.09113(5) 0.37270(10) 0.41152(4) 0.0361(2) Uani 1 1 d . . . . .
H26 H 0.0664 0.3151 0.4434 0.043 Uiso 1 1 calc R U . . .
C27 C 0.03683(5) 0.45946(12) 0.37295(5) 0.0447(3) Uani 1 1 d . . . . .
H27A H 0.0038 0.3929 0.3532 0.054 Uiso 1 1 calc R U . . .
H27B H 0.0104 0.5237 0.4005 0.054 Uiso 1 1 calc R U . . .
C28 C 0.07456(6) 0.54926(12) 0.32270(5) 0.0464(3) Uani 1 1 d . . . . .
H28 H 0.0397 0.6049 0.2985 0.056 Uiso 1 1 calc R U . . .
C29 C 0.11459(7) 0.44640(15) 0.27892(5) 0.0544(3) Uani 1 1 d . . . . .
H29A H 0.1384 0.5021 0.2465 0.065 Uiso 1 1 calc R U . . .
H29B H 0.0817 0.3801 0.2588 0.065 Uiso 1 1 calc R U . . .
C30 C 0.12657(6) 0.65412(11) 0.35419(5) 0.0452(3) Uani 1 1 d . . . . .
H30A H 0.1011 0.7208 0.3813 0.054 Uiso 1 1 calc R U . . .
H30B H 0.1510 0.7109 0.3225 0.054 Uiso 1 1 calc R U . . .
C31 C 0.10719(6) 0.57108(14) 0.49368(5) 0.0524(3) Uani 1 1 d . . . . .
H31A H 0.0855 0.5094 0.5246 0.079 Uiso 1 1 calc R U . . .
H31B H 0.0717 0.6308 0.4743 0.079 Uiso 1 1 calc R U . . .
H31C H 0.1419 0.6321 0.5135 0.079 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_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4411(12) . . yes
O1 H1 0.859(17) . . no
O21 C21 1.4458(12) . . yes
O21 H21 0.814(16) . . no
C1 C11 1.5243(14) . . no
C1 C6 1.5380(13) . . no
C1 C2 1.5355(12) . . no
C2 C10 1.5310(14) . . no
C2 C3 1.5339(14) . . no
C3 C4 1.5289(15) . . no
C4 C9 1.5280(16) . . no
C4 C5 1.5278(15) . . no
C5 C6 1.5267(15) . . no
C6 C7 1.5388(14) . . no
C7 C8 1.5272(16) . . no
C8 C10 1.5310(15) . . no
C8 C9 1.5289(16) . . no
C2 H2 0.9800 . . no
C3 H3B 0.9700 . . no
C3 H3A 0.9700 . . no
C4 H4 0.9800 . . no
C5 H5B 0.9700 . . no
C5 H5A 0.9700 . . no
C6 H6 0.9800 . . no
C7 H7B 0.9700 . . no
C7 H7A 0.9700 . . no
C8 H8 0.9800 . . no
C9 H9B 0.9700 . . no
C9 H9A 0.9700 . . no
C10 H10A 0.9700 . . no
C10 H10B 0.9700 . . no
C11 H11B 0.9600 . . no
C11 H11A 0.9600 . . no
C11 H11C 0.9600 . . no
C21 C26 1.5342(13) . . no
C21 C31 1.5216(15) . . no
C21 C22 1.5384(13) . . no
C22 C30 1.5322(14) . . no
C22 C23 1.5341(14) . . no
C23 C24 1.5307(16) . . no
C24 C29 1.5297(17) . . no
C24 C25 1.5307(15) . . no
C25 C26 1.5303(14) . . no
C26 C27 1.5372(14) . . no
C27 C28 1.5275(15) . . no
C28 C29 1.5275(17) . . no
C28 C30 1.5306(15) . . no
C22 H22 0.9800 . . no
C23 H23A 0.9700 . . no
C23 H23B 0.9700 . . no
C24 H24 0.9800 . . no
C25 H25A 0.9700 . . no
C25 H25B 0.9700 . . no
C26 H26 0.9800 . . no
C27 H27A 0.9700 . . no
C27 H27B 0.9700 . . no
C28 H28 0.9800 . . no
C29 H29A 0.9700 . . no
C29 H29B 0.9700 . . no
C30 H30A 0.9700 . . no
C30 H30B 0.9700 . . no
C31 H31A 0.9600 . . no
C31 H31B 0.9600 . . no
C31 H31C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.6(10) . . . no
C21 O21 H21 105.6(11) . . . no
O1 C1 C2 105.40(7) . . . yes
C2 C1 C6 107.93(7) . . . no
C2 C1 C11 113.32(8) . . . no
O1 C1 C11 106.50(7) . . . yes
C6 C1 C11 112.04(8) . . . no
O1 C1 C6 111.49(7) . . . yes
C1 C2 C10 110.81(8) . . . no
C1 C2 C3 109.49(8) . . . no
C3 C2 C10 108.59(8) . . . no
C2 C3 C4 109.79(8) . . . no
C3 C4 C9 109.40(10) . . . no
C3 C4 C5 109.46(9) . . . no
C5 C4 C9 109.82(8) . . . no
C4 C5 C6 109.38(8) . . . no
C1 C6 C7 110.45(8) . . . no
C1 C6 C5 110.28(8) . . . no
C5 C6 C7 108.27(9) . . . no
C6 C7 C8 109.94(8) . . . no
C7 C8 C9 109.03(9) . . . no
C7 C8 C10 109.18(9) . . . no
C9 C8 C10 109.84(9) . . . no
C4 C9 C8 109.14(9) . . . no
C2 C10 C8 109.67(8) . . . no
C3 C2 H2 109.00 . . . no
C10 C2 H2 109.00 . . . no
C1 C2 H2 109.00 . . . no
C2 C3 H3B 110.00 . . . no
C4 C3 H3A 110.00 . . . no
C4 C3 H3B 110.00 . . . no
H3A C3 H3B 108.00 . . . no
C2 C3 H3A 110.00 . . . no
C3 C4 H4 109.00 . . . no
C5 C4 H4 109.00 . . . no
C9 C4 H4 109.00 . . . no
C4 C5 H5A 110.00 . . . no
C4 C5 H5B 110.00 . . . no
C6 C5 H5B 110.00 . . . no
H5A C5 H5B 108.00 . . . no
C6 C5 H5A 110.00 . . . no
C1 C6 H6 109.00 . . . no
C7 C6 H6 109.00 . . . no
C5 C6 H6 109.00 . . . no
C6 C7 H7A 110.00 . . . no
C8 C7 H7A 110.00 . . . no
C8 C7 H7B 110.00 . . . no
H7A C7 H7B 108.00 . . . no
C6 C7 H7B 110.00 . . . no
C7 C8 H8 110.00 . . . no
C10 C8 H8 110.00 . . . no
C9 C8 H8 110.00 . . . no
C4 C9 H9A 110.00 . . . no
C8 C9 H9A 110.00 . . . no
C8 C9 H9B 110.00 . . . no
H9A C9 H9B 108.00 . . . no
C4 C9 H9B 110.00 . . . no
C2 C10 H10B 110.00 . . . no
C8 C10 H10A 110.00 . . . no
C2 C10 H10A 110.00 . . . no
H10A C10 H10B 108.00 . . . no
C8 C10 H10B 110.00 . . . no
C1 C11 H11B 109.00 . . . no
C1 C11 H11C 109.00 . . . no
H11A C11 H11B 110.00 . . . no
H11A C11 H11C 109.00 . . . no
H11B C11 H11C 110.00 . . . no
C1 C11 H11A 109.00 . . . no
O21 C21 C22 108.96(7) . . . yes
O21 C21 C31 106.43(7) . . . yes
C22 C21 C26 108.16(7) . . . no
C22 C21 C31 113.16(8) . . . no
C26 C21 C31 112.66(8) . . . no
O21 C21 C26 107.26(7) . . . yes
C21 C22 C23 109.69(8) . . . no
C21 C22 C30 110.66(8) . . . no
C23 C22 C30 108.44(8) . . . no
C22 C23 C24 109.81(8) . . . no
C23 C24 C29 109.54(10) . . . no
C25 C24 C29 109.65(9) . . . no
C23 C24 C25 109.21(9) . . . no
C24 C25 C26 109.38(8) . . . no
C21 C26 C25 110.31(8) . . . no
C21 C26 C27 109.97(8) . . . no
C25 C26 C27 108.64(8) . . . no
C26 C27 C28 109.99(8) . . . no
C27 C28 C29 109.01(9) . . . no
C27 C28 C30 109.40(9) . . . no
C29 C28 C30 109.73(9) . . . no
C24 C29 C28 109.32(9) . . . no
C22 C30 C28 109.58(8) . . . no
C21 C22 H22 109.00 . . . no
C23 C22 H22 109.00 . . . no
C30 C22 H22 109.00 . . . no
C22 C23 H23A 110.00 . . . no
C22 C23 H23B 110.00 . . . no
C24 C23 H23A 110.00 . . . no
C24 C23 H23B 110.00 . . . no
H23A C23 H23B 108.00 . . . no
C23 C24 H24 109.00 . . . no
C25 C24 H24 109.00 . . . no
C29 C24 H24 109.00 . . . no
C24 C25 H25A 110.00 . . . no
C24 C25 H25B 110.00 . . . no
C26 C25 H25A 110.00 . . . no
C26 C25 H25B 110.00 . . . no
H25A C25 H25B 108.00 . . . no
C21 C26 H26 109.00 . . . no
C25 C26 H26 109.00 . . . no
C27 C26 H26 109.00 . . . no
C26 C27 H27A 110.00 . . . no
C26 C27 H27B 110.00 . . . no
C28 C27 H27A 110.00 . . . no
C28 C27 H27B 110.00 . . . no
H27A C27 H27B 108.00 . . . no
C27 C28 H28 110.00 . . . no
C29 C28 H28 110.00 . . . no
C30 C28 H28 110.00 . . . no
C24 C29 H29A 110.00 . . . no
C24 C29 H29B 110.00 . . . no
C28 C29 H29A 110.00 . . . no
C28 C29 H29B 110.00 . . . no
H29A C29 H29B 108.00 . . . no
C22 C30 H30A 110.00 . . . no
C22 C30 H30B 110.00 . . . no
C28 C30 H30A 110.00 . . . no
C28 C30 H30B 110.00 . . . no
H30A C30 H30B 108.00 . . . no
C21 C31 H31A 109.00 . . . no
C21 C31 H31B 109.00 . . . no
C21 C31 H31C 109.00 . . . no
H31A C31 H31B 109.00 . . . no
H31A C31 H31C 110.00 . . . no
H31B C31 H31C 110.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -58.84(9) . . . . no
O1 C1 C2 C10 -178.60(7) . . . . no
C6 C1 C2 C3 60.40(9) . . . . no
C6 C1 C2 C10 -59.36(9) . . . . no
C11 C1 C2 C3 -174.92(8) . . . . no
C11 C1 C2 C10 65.32(10) . . . . no
O1 C1 C6 C5 54.53(10) . . . . no
O1 C1 C6 C7 174.17(7) . . . . no
C2 C1 C6 C5 -60.77(10) . . . . no
C2 C1 C6 C7 58.87(10) . . . . no
C11 C1 C6 C5 173.79(8) . . . . no
C11 C1 C6 C7 -66.57(10) . . . . no
C1 C2 C3 C4 -60.70(10) . . . . no
C10 C2 C3 C4 60.40(11) . . . . no
C1 C2 C10 C8 60.42(10) . . . . no
C3 C2 C10 C8 -59.87(11) . . . . no
C2 C3 C4 C5 59.57(11) . . . . no
C2 C3 C4 C9 -60.81(11) . . . . no
C3 C4 C5 C6 -59.19(11) . . . . no
C9 C4 C5 C6 60.94(11) . . . . no
C3 C4 C9 C8 59.94(11) . . . . no
C5 C4 C9 C8 -60.22(12) . . . . no
C4 C5 C6 C1 60.54(10) . . . . no
C4 C5 C6 C7 -60.41(10) . . . . no
C1 C6 C7 C8 -59.98(11) . . . . no
C5 C6 C7 C8 60.86(11) . . . . no
C6 C7 C8 C9 -60.76(11) . . . . no
C6 C7 C8 C10 59.24(11) . . . . no
C7 C8 C9 C4 59.83(12) . . . . no
C10 C8 C9 C4 -59.76(12) . . . . no
C7 C8 C10 C2 -59.33(11) . . . . no
C9 C8 C10 C2 60.17(11) . . . . no
O21 C21 C22 C23 56.36(9) . . . . no
O21 C21 C22 C30 175.96(7) . . . . no
C26 C21 C22 C23 -59.93(10) . . . . no
C26 C21 C22 C30 59.67(10) . . . . no
C31 C21 C22 C23 174.53(8) . . . . no
C31 C21 C22 C30 -65.87(10) . . . . no
O21 C21 C26 C25 -57.05(9) . . . . no
O21 C21 C26 C27 -176.85(7) . . . . no
C22 C21 C26 C25 60.34(10) . . . . no
C22 C21 C26 C27 -59.47(9) . . . . no
C31 C21 C26 C25 -173.83(8) . . . . no
C31 C21 C26 C27 66.37(10) . . . . no
C21 C22 C23 C24 60.48(10) . . . . no
C30 C22 C23 C24 -60.47(11) . . . . no
C21 C22 C30 C28 -59.90(10) . . . . no
C23 C22 C30 C28 60.45(11) . . . . no
C22 C23 C24 C25 -59.76(11) . . . . no
C22 C23 C24 C29 60.34(11) . . . . no
C23 C24 C25 C26 59.51(11) . . . . no
C29 C24 C25 C26 -60.52(11) . . . . no
C23 C24 C29 C28 -59.44(12) . . . . no
C25 C24 C29 C28 60.40(12) . . . . no
C24 C25 C26 C21 -60.65(10) . . . . no
C24 C25 C26 C27 59.97(11) . . . . no
C21 C26 C27 C28 60.37(10) . . . . no
C25 C26 C27 C28 -60.45(11) . . . . no
C26 C27 C28 C29 60.60(11) . . . . no
C26 C27 C28 C30 -59.39(11) . . . . no
C27 C28 C29 C24 -60.12(12) . . . . no
C30 C28 C29 C24 59.67(12) . . . . no
C27 C28 C30 C22 58.92(11) . . . . no
C29 C28 C30 C22 -60.63(11) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 O21 3.0012(10) . 2_564 no
O1 O21 2.8351(10) . 8_564 no
O21 O1 2.8351(10) . 8_565 no
O21 O1 3.0012(10) . 2_565 no
O1 H21 2.188(16) . 2_564 no
O1 H5A 2.5600 . . no
O1 H31C 2.8600 . 2_564 no
O1 H3A 2.4500 . . no
O21 H25B 2.4900 . . no
O21 H1 1.995(17) . 8_565 no
O21 H23B 2.5100 . . no
C1 C9 3.5704(14) . . no
C3 C7 3.5125(14) . . no
C5 C10 3.5311(14) . . no
C7 C3 3.5125(14) . . no
C9 C1 3.5704(14) . . no
C10 C5 3.5311(14) . . no
C21 C29 3.5660(14) . . no
C23 C27 3.5152(13) . . no
C25 C30 3.5352(14) . . no
C27 C23 3.5152(13) . . no
C29 C21 3.5660(14) . . no
C30 C25 3.5352(14) . . no
C1 H21 2.981(15) . 2_564 no
C3 H5A 2.9800 . 7_555 no
C5 H1 2.954(15) . . no
C7 H11B 2.7600 . . no
C10 H11B 2.7600 . . no
C11 H7A 3.0500 . 5_575 no
C11 H7A 2.7500 . . no
C11 H10B 2.7600 . . no
C23 H21 3.071(15) . . no
C27 H31B 2.7500 . . no
C30 H31B 2.7700 . . no
C31 H30A 2.7600 . . no
C31 H27B 2.7300 . . no
H1 H21 2.44(2) . 8_564 no
H1 C5 2.954(15) . . no
H1 H5A 2.4900 . . no
H1 H6 2.4500 . . no
H1 H11C 2.5300 . . no
H1 O21 1.995(17) . 8_564 no
H2 H5A 2.4300 . 7_555 no
H2 H11A 2.5500 . . no
H2 H21 2.5500 . 2_564 no
H3A H5A 2.5200 . . no
H3A O1 2.4500 . . no
H3B H10A 2.5000 . . no
H3B H5A 2.5800 . 7_555 no
H3B H9A 2.5100 . . no
H4 H24 2.5100 . 7_555 no
H4 H30B 2.5000 . . no
H5A O1 2.5600 . . no
H5A H3A 2.5200 . . no
H5A C3 2.9800 . 7_545 no
H5A H2 2.4300 . 7_545 no
H5A H3B 2.5800 . 7_545 no
H5A H1 2.4900 . . no
H5B H7B 2.4800 . . no
H5B H9B 2.5100 . . no
H5B H29A 2.5800 . . no
H6 H1 2.4500 . . no
H6 H11C 2.5000 . . no
H7A C11 2.7500 . . no
H7A H10B 2.5200 . . no
H7A H11B 2.2000 . . no
H7A C11 3.0500 . 5_575 no
H7A H11C 2.4900 . 5_575 no
H7B H5B 2.4800 . . no
H7B H9B 2.5000 . . no
H7B H30A 2.4700 . 4_555 no
H9A H3B 2.5100 . . no
H9A H10A 2.5300 . . no
H9B H5B 2.5100 . . no
H9B H7B 2.5000 . . no
H10A H9A 2.5300 . . no
H10A H29B 2.6000 . 1_565 no
H10A H3B 2.5000 . . no
H10B H7A 2.5200 . . no
H10B H11B 2.2000 . . no
H10B C11 2.7600 . . no
H10B H27A 2.5900 . 4_565 no
H11A H2 2.5500 . . no
H11A H31C 2.5900 . 8_574 no
H11B C10 2.7600 . . no
H11B H7A 2.2000 . . no
H11B H10B 2.2000 . . no
H11B C7 2.7600 . . no
H11C H6 2.5000 . . no
H11C H7A 2.4900 . 5_575 no
H11C H1 2.5300 . . no
H21 C23 3.071(15) . . no
H21 H22 2.4300 . . no
H21 H31C 2.3200 . . no
H21 O1 2.188(16) . 2_565 no
H21 C1 2.981(15) . 2_565 no
H21 H2 2.5500 . 2_565 no
H21 H1 2.44(2) . 8_565 no
H22 H21 2.4300 . . no
H22 H31C 2.5400 . . no
H22 H25B 2.4400 . 7_555 no
H23A H29A 2.5200 . . no
H23A H30B 2.4900 . . no
H23B O21 2.5100 . . no
H23B H25B 2.5200 . . no
H24 H4 2.5100 . 7_545 no
H25A H27A 2.5000 . . no
H25A H29B 2.5100 . . no
H25B O21 2.4900 . . no
H25B H23B 2.5200 . . no
H25B H22 2.4400 . 7_545 no
H26 H31A 2.5100 . . no
H27A H25A 2.5000 . . no
H27A H29B 2.5000 . . no
H27A H10B 2.5900 . 4_545 no
H27B C31 2.7300 . . no
H27B H30A 2.5300 . . no
H27B H31B 2.1900 . . no
H27B H31A 2.4300 . 5_566 no
H28 H28 2.5500 . 4_555 no
H29A H5B 2.5800 . . no
H29A H23A 2.5200 . . no
H29A H30B 2.5200 . . no
H29B H10A 2.6000 . 1_545 no
H29B H25A 2.5100 . . no
H29B H27A 2.5000 . . no
H30A C31 2.7600 . . no
H30A H27B 2.5300 . . no
H30A H31B 2.2200 . . no
H30A H7B 2.4700 . 4_555 no
H30B H4 2.5000 . . no
H30B H23A 2.4900 . . no
H30B H29A 2.5200 . . no
H31A H26 2.5100 . . no
H31A H27B 2.4300 . 5_566 no
H31B C27 2.7500 . . no
H31B C30 2.7700 . . no
H31B H27B 2.1900 . . no
H31B H30A 2.2200 . . no
H31C H21 2.3200 . . no
H31C H22 2.5400 . . no
H31C O1 2.8600 . 2_565 no
H31C H11A 2.5900 . 8_575 no

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1 O21 0.859(17) 1.995(17) 2.8351(10) 165.4(15) 8_564 yes
O21 H21 O1 0.814(16) 2.188(16) 3.0012(10) 176.5(16) 2_565 yes
C3 H3A O1 0.9700 2.4500 2.8014(13) 101.00 . yes
C5 H5A O1 0.9700 2.5600 2.8905(13) 100.00 . yes
C23 H23B O21 0.9700 2.5100 2.8536(13) 100.00 . yes
C25 H25B O21 0.9700 2.4900 2.8341(13) 101.00 . yes

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.028



####################################################################### 
# 
# 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_2-AdamantanolRietveld330K
_database_code_depnum_ccdc_archive 'CCDC 2152769'
loop_
_audit_author_name
_audit_author_address
'Ph. Negrier'
;Universite de Bordeaux
France
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;

_vrf_ATOM007_2-AdamantanolRietveld330K 
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: Powder Rigid body Global Isotropic Factor
;
_vrf_PLAT029_2-AdamantanolRietveld330K 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.000 Why?
RESPONSE: Powder diffraction - no monocrystal
;
_vrf_PLAT183_2-AdamantanolRietveld330K 
;
PROBLEM: Missing _cell_measurement_reflns_used Value ....     Please Do !
RESPONSE: Powder diffraction - no monocrystal
;
_vrf_PLAT201_2-AdamantanolRietveld330K 
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         13 Report
RESPONSE: Powder Rigid body Global Isotropic Factor
;
_vrf_PLAT880_2-AdamantanolRietveld330K 
;
PROBLEM: N0 datum for _diffrn_reflns_number .............     Please Do !
RESPONSE: Global Powder Pattern diffraction Refinement
;
_vrf_PLAT881_2-AdamantanolRietveld330K 
;
PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do !
RESPONSE: Global Powder Pattern diffraction Refinement
;
_vrf_PLAT430_2-AdamantanolRietveld330K 
;
PROBLEM: Short Inter D...A Contact O15 ..O16	 .		Check
RESPONSE: Disordered Atoms- Occupancy factor 0.5 each;
;

_audit_creation_date             2020-07-10
_audit_creation_method           'Materials Studio'
_chemical_name_common            2-Adamantanol
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 O'
_chemical_formula_weight         152.23

_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 2/M'
_symmetry_Int_Tables_number      12
_symmetry_cell_setting           monoclinic

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,-z
3 -x,-y,-z
4 x,-y,z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,z

_cell_length_a                   11.716(2)
_cell_length_b                   20.381(8)
_cell_length_c                   11.709(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.58(3)
_cell_angle_gamma                90.0000
_cell_volume                     2634(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    330
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      40

_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       Powder
_exptl_crystal_colour            White
_diffrn_ambient_temperature      330(1)
_diffrn_radiation_wavelength     1.540562
_diffrn_radiation_type           CuK\a~1~
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Curved Quartz'
_diffrn_measurement_device_type  'Inel CPS120'

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
C1 C 0.3337(5) 0.1123(4) 0.3639(7) 0.05000 Uiso 1.00000
H111 H 0.3497(5) 0.1127(6) 0.4614(6) 0.05000 Uiso 0.50000
H112 H 0.4308(5) 0.1140(6) 0.4148(7) 0.05000 Uiso 0.50000
C2 C 0.3876(5) 0.1757(3) 0.3266(4) 0.05000 Uiso 0.50000
H2 H 0.4849(5) 0.1782(6) 0.3767(4) 0.05000 Uiso 0.50000
C3 C 0.3659(5) 0.17379(19) 0.1875(4) 0.05000 Uiso 1.00000
H31 H 0.4046(6) 0.21758(19) 0.1607(6) 0.05000 Uiso 0.50000
H32 H 0.4118(5) 0.13127(18) 0.1659(6) 0.05000 Uiso 0.50000
H33 H 0.3529(5) 0.1725(4) 0.0906(4) 0.05000 Uiso 0.50000
H34 H 0.4635(5) 0.1763(2) 0.2359(4) 0.05000 Uiso 0.50000
C4 C 0.2271(5) 0.1701(5) 0.1158(4) 0.05000 Uiso 0.50000
H4 H 0.2121(5) 0.1688(7) 0.0184(4) 0.05000 Uiso 0.50000
C5 C 0.1736(6) 0.1068(4) 0.1535(7) 0.05000 Uiso 1.00000
H51 H 0.2166(9) 0.0633(4) 0.1314(11) 0.05000 Uiso 0.50000
H52 H 0.0767(6) 0.1033(7) 0.1027(7) 0.05000 Uiso 0.50000
H53 H 0.1578(7) 0.1045(7) 0.0562(7) 0.05000 Uiso 0.50000
H54 H 0.1355(8) 0.0620(4) 0.1779(10) 0.05000 Uiso 0.50000
C6 C 0.1948(6) 0.10851(18) 0.2925(6) 0.05000 Uiso 0.50000
H6 H 0.1572(8) 0.06406(18) 0.3188(10) 0.05000 Uiso 0.50000
C7 C 0.1844(8) 0.23379(19) 0.2849(8) 0.05000 Uiso 0.50000
H7 H 0.1396(11) 0.27701(19) 0.3059(12) 0.05000 Uiso 0.50000
C8 C 0.3233(8) 0.2373(3) 0.3563(8) 0.05000 Uiso 1.00000
H81 H 0.3391(8) 0.2396(6) 0.4537(8) 0.05000 Uiso 0.50000
H82 H 0.3614(11) 0.2820(3) 0.3320(12) 0.05000 Uiso 0.50000
H83 H 0.4203(8) 0.2408(6) 0.4072(8) 0.05000 Uiso 0.50000
H84 H 0.2803(11) 0.2808(3) 0.3785(12) 0.05000 Uiso 0.50000
C9 C 0.1632(7) 0.2318(5) 0.1460(8) 0.05000 Uiso 1.00000
H91 H 0.1990(10) 0.2764(5) 0.1185(12) 0.05000 Uiso 0.50000
H92 H 0.0661(7) 0.2301(7) 0.0951(8) 0.05000 Uiso 0.50000
H93 H 0.1178(10) 0.2752(5) 0.1651(12) 0.05000 Uiso 0.50000
H94 H 0.1472(7) 0.2313(7) 0.0485(8) 0.05000 Uiso 0.50000
C10 C 0.1310(5) 0.17028(18) 0.3224(4) 0.05000 Uiso 1.00000
H101 H 0.0334(5) 0.1677(3) 0.2740(4) 0.05000 Uiso 0.50000
H102 H 0.1440(5) 0.1716(3) 0.4192(4) 0.05000 Uiso 0.50000
H103 H 0.0923(5) 0.12648(18) 0.3492(5) 0.05000 Uiso 0.50000
H104 H 0.0851(7) 0.21280(18) 0.3440(7) 0.05000 Uiso 0.50000
C11 C 0.2698(5) 0.1739(3) 0.3941(4) 0.05000 Uiso 0.50000
H11 H 0.2848(5) 0.1753(6) 0.4915(4) 0.05000 Uiso 0.50000
C12 C 0.3021(7) 0.2355(2) 0.2174(8) 0.05000 Uiso 0.50000
H12 H 0.3397(10) 0.2800(2) 0.1911(11) 0.05000 Uiso 0.50000
C13 C 0.3125(6) 0.11028(18) 0.2249(7) 0.05000 Uiso 0.50000
H13 H 0.3574(8) 0.06706(18) 0.2039(11) 0.05000 Uiso 0.50000
C14 C 0.1094(5) 0.1684(5) 0.1833(4) 0.05000 Uiso 0.50000
H14 H 0.0120(5) 0.1658(7) 0.1332(4) 0.05000 Uiso 0.50000
O15 O 0.3937(9) 0.0552(4) 0.3406(12) 0.05000 Uiso 0.50000
H151 H 0.3554(11) 0.0178(4) 0.3661(15) 0.05000 Uiso 0.25000
H152 H 0.4777(8) 0.0684(6) 0.3546(12) 0.05000 Uiso 0.25000
O16 O 0.2885(8) 0.0536(4) 0.4009(12) 0.05000 Uiso 0.50000
H161 H 0.3048(8) 0.0584(6) 0.4883(11) 0.05000 Uiso 0.25000
H162 H 0.3324(11) 0.0174(4) 0.3792(15) 0.05000 Uiso 0.25000
O21 O 0.4025(5) 0.05566(0) 0.6546(4) 0.05000 Uiso 0.50000
H211 H 0.4823(5) 0.04101(0) 0.6550(4) 0.05000 Uiso 0.25000
H212 H 0.3820(5) 0.05212(0) 0.5664(4) 0.05000 Uiso 0.25000
C21 C 0.3476(5) 0.00000(0) 0.6899(4) 0.05000 Uiso 1.00000
H21 H 0.3880(5) 0.04339(0) 0.6640(4) 0.05000 Uiso 0.50000
C22 C 0.3743(5) 0.00000(0) 0.8300(4) 0.05000 Uiso 1.00000
H22 H 0.4723(5) 0.00000(0) 0.8770(4) 0.05000 Uiso 1.00000
C23 C 0.3172(5) 0.06251(0) 0.8661(4) 0.05000 Uiso 1.00000
H232 H 0.3366(5) 0.06343(0) 0.9643(4) 0.05000 Uiso 1.00000
H231 H 0.3576(5) 0.10659(0) 0.8425(4) 0.05000 Uiso 1.00000
C24 C 0.1773(5) 0.06265(0) 0.7993(4) 0.05000 Uiso 1.00000
H24 H 0.1376(5) 0.10649(0) 0.8249(4) 0.05000 Uiso 1.00000
C25 C 0.1511(5) 0.06250(0) 0.6593(4) 0.05000 Uiso 1.00000
H251 H 0.1889(5) 0.10659(0) 0.6325(4) 0.05000 Uiso 1.00000
H252 H 0.0533(5) 0.06343(0) 0.6113(4) 0.05000 Uiso 1.00000
C26 C 0.2077(5) 0.00000(0) 0.6225(4) 0.05000 Uiso 1.00000
H26 H 0.1892(5) 0.00000(0) 0.5244(4) 0.05000 Uiso 1.00000
C27 C 0.1207(5) 0.00000(0) 0.8355(4) 0.05000 Uiso 1.00000
H271 H 0.1372(5) 0.00000(0) 0.9332(4) 0.05000 Uiso 1.00000
H272 H 0.0225(5) 0.00000(0) 0.7902(4) 0.05000 Uiso 1.00000

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O15 O16 1.613(16) . . yes
O15 C1 1.432(12) . . yes
O16 C1 1.433(12) . . yes
O21 C21 1.432(5) . . yes
O15 H162 1.237(16) . . no
O15 H151 0.981(15) . . no
O15 H152 0.980(16) . . no
O16 H162 0.980(15) . . no
O16 H151 1.236(16) . . no
O16 H161 0.981(18) . . no
O21 H21 0.341(6) . . no
O21 H211 0.980(8) . . no
O21 H212 0.981(6) . . no
C1 C2 1.563(10) . . no
C1 C6 1.563(10) . . no
C1 C11 1.562(10) . . no
C1 C13 1.563(11) . . no
C2 C3 1.563(6) . . no
C2 C8 1.562(10) . . no
C3 C4 1.562(8) . . no
C3 C12 1.562(8) . . no
C3 C13 1.563(7) . . no
C4 C5 1.561(12) . . no
C4 C9 1.563(13) . . no
C5 C13 1.562(11) . . no
C5 C14 1.562(12) . . no
C5 C6 1.562(10) . . no
C6 C10 1.563(7) . . no
C7 C9 1.561(13) . . no
C7 C8 1.562(14) . . no
C7 C10 1.563(8) . . no
C8 C12 1.561(13) . . no
C8 C11 1.564(10) . . no
C9 C12 1.562(12) . . no
C9 C14 1.563(13) . . no
C10 C11 1.562(8) . . no
C10 C14 1.563(6) . . no
C21 C26 1.563(8) . . no
C21 C22 1.564(6) . . no
C22 C23 1.562(5) . 4_555 no
C22 C23 1.562(5) . . no
C23 C24 1.562(8) . . no
C24 C25 1.563(6) . . no
C24 C27 1.562(5) . . no
C25 C26 1.562(5) . . no
C1 H111 1.093(10) . . no
C1 H112 1.094(10) . . no
C2 H2 1.095(8) . . no
C3 H31 1.094(7) . . no
C3 H32 1.093(7) . . no
C3 H33 1.093(6) . . no
C3 H34 1.094(8) . . no
C4 H4 1.095(6) . . no
C5 H51 1.093(12) . . no
C5 H52 1.093(11) . . no
C5 H53 1.092(11) . . no
C5 H54 1.096(12) . . no
C6 H6 1.096(8) . . no
C7 H7 1.095(11) . . no
C8 H81 1.093(13) . . no
C8 H82 1.093(12) . . no
C8 H83 1.095(14) . . no
C8 H84 1.093(12) . . no
C9 H91 1.094(15) . . no
C9 H92 1.094(12) . . no
C9 H93 1.093(15) . . no
C9 H94 1.093(12) . . no
C10 H101 1.094(8) . . no
C10 H102 1.092(6) . . no
C10 H103 1.094(6) . . no
C10 H104 1.093(8) . . no
C11 H11 1.095(6) . . no
C12 H12 1.097(10) . . no
C13 H13 1.095(9) . . no
C14 H14 1.096(8) . . no
C21 H21 1.093(5) . . no
C21 H21 1.093(5) . 4_555 no
C22 H22 1.094(8) . . no
C23 H231 1.093(5) . . no
C23 H232 1.095(6) . . no
C24 H24 1.095(5) . . no
C25 H251 1.093(5) . . no
C25 H252 1.094(8) . . no
C26 H26 1.095(6) . . no
C27 H271 1.094(6) . . no
C27 H272 1.094(8) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O16 O15 C1 55.8(6) . . . yes
O15 O16 C1 55.7(6) . . . yes
C1 O15 H152 105.9(10) . . . no
C1 O15 H162 93.1(9) . . . no
C1 O15 H151 105.7(12) . . . no
C1 O16 H162 105.7(12) . . . no
C1 O16 H151 93.1(9) . . . no
C1 O16 H161 105.7(11) . . . no
C21 O21 H212 105.7(4) . . . no
C21 O21 H211 106.1(3) . . . no
C21 O21 H21 5.2(9) . . . no
O15 C1 C6 110.3(7) . . . yes
O15 C1 C11 178.0(8) . . . yes
O15 C1 C13 72.4(7) . . . yes
O16 C1 C2 178.0(7) . . . yes
O16 C1 C6 72.3(6) . . . yes
O16 C1 C11 110.4(6) . . . yes
O16 C1 C13 110.3(7) . . . yes
O15 C1 O16 68.5(7) . . . yes
O15 C1 C2 110.4(6) . . . yes
C2 C1 C11 70.6(5) . . . no
C2 C1 C13 70.7(4) . . . no
C6 C1 C11 70.6(4) . . . no
C6 C1 C13 70.6(5) . . . no
C11 C1 C13 109.6(5) . . . no
C2 C1 C6 109.7(5) . . . no
C1 C2 C3 109.3(5) . . . no
C3 C2 C8 109.3(5) . . . no
C1 C2 C8 109.4(5) . . . no
C2 C3 C12 70.7(4) . . . no
C2 C3 C13 70.7(4) . . . no
C4 C3 C13 70.6(5) . . . no
C12 C3 C13 109.7(5) . . . no
C4 C3 C12 70.7(5) . . . no
C2 C3 C4 109.8(5) . . . no
C5 C4 C9 109.4(6) . . . no
C3 C4 C5 109.4(6) . . . no
C3 C4 C9 109.3(6) . . . no
C13 C5 C14 109.7(6) . . . no
C4 C5 C6 109.7(5) . . . no
C4 C5 C13 70.7(4) . . . no
C4 C5 C14 70.6(5) . . . no
C6 C5 C13 70.6(5) . . . no
C6 C5 C14 70.7(4) . . . no
C5 C6 C10 109.3(5) . . . no
C1 C6 C5 109.4(6) . . . no
C1 C6 C10 109.3(5) . . . no
C8 C7 C10 109.3(5) . . . no
C8 C7 C9 109.4(7) . . . no
C9 C7 C10 109.4(6) . . . no
C2 C8 C11 70.6(4) . . . no
C2 C8 C7 109.7(5) . . . no
C7 C8 C11 70.7(5) . . . no
C7 C8 C12 70.6(6) . . . no
C11 C8 C12 109.7(5) . . . no
C2 C8 C12 70.7(5) . . . no
C4 C9 C12 70.6(5) . . . no
C4 C9 C14 70.5(6) . . . no
C4 C9 C7 109.6(6) . . . no
C12 C9 C14 109.6(6) . . . no
C7 C9 C14 70.7(5) . . . no
C7 C9 C12 70.6(6) . . . no
C6 C10 C11 70.6(4) . . . no
C6 C10 C7 109.7(5) . . . no
C7 C10 C14 70.6(5) . . . no
C6 C10 C14 70.7(5) . . . no
C7 C10 C11 70.7(5) . . . no
C11 C10 C14 109.7(5) . . . no
C1 C11 C8 109.4(5) . . . no
C1 C11 C10 109.4(4) . . . no
C8 C11 C10 109.3(5) . . . no
C3 C12 C8 109.4(5) . . . no
C3 C12 C9 109.4(6) . . . no
C8 C12 C9 109.4(7) . . . no
C3 C13 C5 109.3(5) . . . no
C1 C13 C5 109.4(6) . . . no
C1 C13 C3 109.3(5) . . . no
C5 C14 C10 109.3(6) . . . no
C9 C14 C10 109.4(6) . . . no
C5 C14 C9 109.4(6) . . . no
O21 C21 O21 104.8(4) . . 4_555 yes
O21 C21 C22 110.6(3) . . . yes
O21 C21 C26 110.5(3) . . . yes
O21 C21 C22 110.6(3) 4_555 . . yes
O21 C21 C26 110.5(3) 4_555 . . yes
C22 C21 C26 109.7(4) . . . no
C21 C22 C23 109.3(3) . . . no
C23 C22 C23 109.3(4) . . 4_555 no
C21 C22 C23 109.3(3) . . 4_555 no
C22 C23 C24 109.8(3) . . . no
C25 C24 C27 109.3(3) . . . no
C23 C24 C27 109.4(3) . . . no
C23 C24 C25 109.2(4) . . . no
C24 C25 C26 109.8(3) . . . no
C21 C26 C25 109.3(3) . . . no
C21 C26 C25 109.3(3) . . 4_555 no
C25 C26 C25 109.3(4) . . 4_555 no
C24 C27 C24 109.7(4) . . 4_555 no
O15 C1 H111 106.4(10) . . . no
O15 C1 H112 69.0(9) . . . no
O16 C1 H111 69.0(9) . . . no
O16 C1 H112 106.5(9) . . . no
C2 C1 H111 110.0(8) . . . no
C2 C1 H112 71.5(7) . . . no
C6 C1 H111 110.0(6) . . . no
C6 C1 H112 178.8(9) . . . no
C11 C1 H111 71.6(7) . . . no
C11 C1 H112 110.0(9) . . . no
C13 C1 H111 178.7(9) . . . no
C13 C1 H112 110.0(7) . . . no
H111 C1 H112 69.4(7) . . . no
C1 C2 H2 109.5(7) . . . no
C3 C2 H2 109.7(5) . . . no
C8 C2 H2 109.7(8) . . . no
C2 C3 H31 109.9(5) . . . no
C2 C3 H32 109.9(5) . . . no
C2 C3 H33 178.7(7) . . . no
C2 C3 H34 71.5(4) . . . no
C4 C3 H31 110.0(6) . . . no
C4 C3 H32 110.0(6) . . . no
C4 C3 H33 71.5(5) . . . no
C4 C3 H34 178.8(5) . . . no
C12 C3 H31 71.5(5) . . . no
C12 C3 H32 178.8(6) . . . no
C12 C3 H33 110.0(6) . . . no
C12 C3 H34 110.0(5) . . . no
C13 C3 H31 178.8(6) . . . no
C13 C3 H32 71.5(4) . . . no
C13 C3 H33 110.0(6) . . . no
C13 C3 H34 109.9(5) . . . no
H31 C3 H32 107.3(7) . . . no
H31 C3 H33 69.4(6) . . . no
H31 C3 H34 69.4(5) . . . no
H32 C3 H33 69.5(6) . . . no
H32 C3 H34 69.3(5) . . . no
H33 C3 H34 107.3(6) . . . no
C3 C4 H4 109.6(6) . . . no
C5 C4 H4 109.6(10) . . . no
C9 C4 H4 109.5(9) . . . no
C4 C5 H51 110.1(8) . . . no
C4 C5 H52 110.0(9) . . . no
C4 C5 H53 71.6(8) . . . no
C4 C5 H54 178.7(9) . . . no
C6 C5 H51 109.9(9) . . . no
C6 C5 H52 110.0(7) . . . no
C6 C5 H53 178.7(10) . . . no
C6 C5 H54 71.5(7) . . . no
C13 C5 H51 71.5(7) . . . no
C13 C5 H52 178.7(10) . . . no
C13 C5 H53 110.0(8) . . . no
C13 C5 H54 109.9(8) . . . no
C14 C5 H51 178.8(9) . . . no
C14 C5 H52 71.6(8) . . . no
C14 C5 H53 110.0(9) . . . no
C14 C5 H54 110.1(8) . . . no
H51 C5 H52 107.2(11) . . . no
H51 C5 H53 69.4(10) . . . no
H51 C5 H54 69.3(9) . . . no
H52 C5 H53 69.4(8) . . . no
H52 C5 H54 69.4(10) . . . no
H53 C5 H54 107.2(11) . . . no
C1 C6 H6 109.6(7) . . . no
C5 C6 H6 109.6(7) . . . no
C10 C6 H6 109.6(7) . . . no
C8 C7 H7 109.6(9) . . . no
C9 C7 H7 109.5(9) . . . no
C10 C7 H7 109.6(9) . . . no
C2 C8 H81 109.9(8) . . . no
C2 C8 H82 110.0(10) . . . no
C2 C8 H83 71.5(8) . . . no
C2 C8 H84 178.7(10) . . . no
C7 C8 H81 110.0(9) . . . no
C7 C8 H82 110.0(9) . . . no
C7 C8 H83 178.7(9) . . . no
C7 C8 H84 71.6(9) . . . no
C11 C8 H81 71.6(8) . . . no
C11 C8 H82 178.7(11) . . . no
C11 C8 H83 110.0(8) . . . no
C11 C8 H84 110.0(10) . . . no
C12 C8 H81 178.8(8) . . . no
C12 C8 H82 71.6(8) . . . no
C12 C8 H83 110.0(9) . . . no
C12 C8 H84 110.0(9) . . . no
H81 C8 H82 107.1(11) . . . no
H81 C8 H83 69.4(9) . . . no
H81 C8 H84 69.4(10) . . . no
H82 C8 H83 69.4(11) . . . no
H82 C8 H84 69.3(9) . . . no
H83 C8 H84 107.2(11) . . . no
C4 C9 H91 110.0(9) . . . no
C4 C9 H92 109.9(10) . . . no
C4 C9 H93 178.8(11) . . . no
C4 C9 H94 71.6(9) . . . no
C7 C9 H91 110.0(10) . . . no
C7 C9 H92 110.0(9) . . . no
C7 C9 H93 71.6(9) . . . no
C7 C9 H94 178.8(10) . . . no
C12 C9 H91 71.6(8) . . . no
C12 C9 H92 178.9(10) . . . no
C12 C9 H93 110.0(10) . . . no
C12 C9 H94 110.0(9) . . . no
C14 C9 H91 178.8(10) . . . no
C14 C9 H92 71.5(9) . . . no
C14 C9 H93 110.0(9) . . . no
C14 C9 H94 109.9(10) . . . no
H91 C9 H92 107.3(12) . . . no
H91 C9 H93 69.4(11) . . . no
H91 C9 H94 69.4(11) . . . no
H92 C9 H93 69.4(11) . . . no
H92 C9 H94 69.4(8) . . . no
H93 C9 H94 107.2(13) . . . no
C6 C10 H101 109.9(5) . . . no
C6 C10 H102 110.0(5) . . . no
C6 C10 H103 71.5(4) . . . no
C6 C10 H104 178.8(6) . . . no
C7 C10 H101 110.0(5) . . . no
C7 C10 H102 110.0(5) . . . no
C7 C10 H103 178.8(6) . . . no
C7 C10 H104 71.5(5) . . . no
C11 C10 H101 178.8(5) . . . no
C11 C10 H102 71.5(5) . . . no
C11 C10 H103 110.0(5) . . . no
C11 C10 H104 110.0(6) . . . no
C14 C10 H101 71.5(4) . . . no
C14 C10 H102 178.8(7) . . . no
C14 C10 H103 109.9(5) . . . no
C14 C10 H104 109.9(6) . . . no
H101 C10 H102 107.3(6) . . . no
H101 C10 H103 69.4(5) . . . no
H101 C10 H104 69.4(6) . . . no
H102 C10 H103 69.5(5) . . . no
H102 C10 H104 69.4(6) . . . no
H103 C10 H104 107.3(7) . . . no
C1 C11 H11 109.6(8) . . . no
C8 C11 H11 109.5(8) . . . no
C10 C11 H11 109.6(6) . . . no
C3 C12 H12 109.6(9) . . . no
C8 C12 H12 109.5(8) . . . no
C9 C12 H12 109.5(9) . . . no
C1 C13 H13 109.5(8) . . . no
C3 C13 H13 109.6(7) . . . no
C5 C13 H13 109.6(8) . . . no
C5 C14 H14 109.6(10) . . . no
C9 C14 H14 109.6(9) . . . no
C10 C14 H14 109.6(5) . . . no
O21 C21 H21 1.6(3) . . . no
O21 C21 H21 106.4(5) . . 4_555 no
C22 C21 H21 109.8(4) . . . no
C22 C21 H21 109.8(4) . . 4_555 no
C26 C21 H21 109.8(4) . . . no
C26 C21 H21 109.8(4) . . 4_555 no
O21 C21 H21 106.4(5) 4_555 . . no
H21 C21 H21 108.0(6) . . 4_555 no
O21 C21 H21 1.6(3) 4_555 . 4_555 no
C21 C22 H22 109.6(5) . . . no
C23 C22 H22 109.7(3) . . . no
C23 C22 H22 109.7(3) 4_555 . . no
C22 C23 H231 109.9(5) . . . no
C22 C23 H232 110.0(3) . . . no
C24 C23 H231 110.0(4) . . . no
C24 C23 H232 109.9(6) . . . no
H231 C23 H232 107.2(4) . . . no
C23 C24 H24 109.6(4) . . . no
C25 C24 H24 109.7(4) . . . no
C27 C24 H24 109.6(5) . . . no
C24 C25 H251 110.1(4) . . . no
C24 C25 H252 110.0(5) . . . no
C26 C25 H251 109.9(5) . . . no
C26 C25 H252 109.9(3) . . . no
H251 C25 H252 107.1(4) . . . no
C21 C26 H26 109.6(6) . . . no
C25 C26 H26 109.7(3) . . . no
C25 C26 H26 109.7(3) 4_555 . . no
C24 C27 H271 110.0(3) . . . no
C24 C27 H272 110.0(3) . . . no
H271 C27 H272 107.2(6) . . . no
C24 C27 H271 110.0(3) 4_555 . . no
C24 C27 H272 110.0(3) 4_555 . . no

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
O16 O15 C1 C2 178.2(8) . . . . no
O16 O15 C1 C6 -60.4(8) . . . . no
O16 O15 C1 C13 -121.1(8) . . . . no
O15 O16 C1 C6 121.2(8) . . . . no
O15 O16 C1 C11 -178.2(8) . . . . no
O15 O16 C1 C13 60.5(8) . . . . no
O15 C1 C2 C3 62.0(8) . . . . no
O15 C1 C2 C8 -178.4(8) . . . . no
C6 C1 C2 C3 -59.8(7) . . . . no
C6 C1 C2 C8 59.8(7) . . . . no
C11 C1 C2 C3 -119.8(5) . . . . no
C11 C1 C2 C8 -0.2(5) . . . . no
C13 C1 C2 C3 0.2(5) . . . . no
C13 C1 C2 C8 119.8(6) . . . . no
O15 C1 C6 C5 -62.0(8) . . . . no
O15 C1 C6 C10 178.4(7) . . . . no
O16 C1 C6 C5 -120.1(7) . . . . no
O16 C1 C6 C10 120.2(7) . . . . no
C2 C1 C6 C5 59.8(6) . . . . no
C2 C1 C6 C10 -59.8(7) . . . . no
C11 C1 C6 C5 119.9(5) . . . . no
C11 C1 C6 C10 0.2(5) . . . . no
C13 C1 C6 C5 -0.3(5) . . . . no
C13 C1 C6 C10 -119.9(4) . . . . no
O16 C1 C11 C8 178.4(7) . . . . no
O16 C1 C11 C10 -61.9(8) . . . . no
C2 C1 C11 C8 0.2(5) . . . . no
C2 C1 C11 C10 120.0(4) . . . . no
C6 C1 C11 C8 -119.9(5) . . . . no
C6 C1 C11 C10 -0.2(5) . . . . no
C13 C1 C11 C8 -59.9(7) . . . . no
C13 C1 C11 C10 59.9(6) . . . . no
O15 C1 C13 C3 -120.2(7) . . . . no
O15 C1 C13 C5 120.2(6) . . . . no
O16 C1 C13 C3 -178.3(6) . . . . no
O16 C1 C13 C5 62.0(7) . . . . no
C2 C1 C13 C3 -0.2(5) . . . . no
C2 C1 C13 C5 -119.9(5) . . . . no
C6 C1 C13 C3 119.9(5) . . . . no
C6 C1 C13 C5 0.3(5) . . . . no
C11 C1 C13 C3 59.9(7) . . . . no
C11 C1 C13 C5 -59.8(6) . . . . no
C1 C2 C3 C4 59.8(6) . . . . no
C1 C2 C3 C12 119.9(5) . . . . no
C1 C2 C3 C13 -0.2(5) . . . . no
C8 C2 C3 C4 -59.9(7) . . . . no
C8 C2 C3 C12 0.2(6) . . . . no
C8 C2 C3 C13 -119.9(6) . . . . no
C1 C2 C8 C7 -59.8(7) . . . . no
C1 C2 C8 C11 0.2(5) . . . . no
C1 C2 C8 C12 -119.9(5) . . . . no
C3 C2 C8 C7 59.8(7) . . . . no
C3 C2 C8 C11 119.9(5) . . . . no
C3 C2 C8 C12 -0.2(6) . . . . no
C2 C3 C4 C5 -59.9(6) . . . . no
C2 C3 C4 C9 60.0(7) . . . . no
C12 C3 C4 C5 -120.0(6) . . . . no
C12 C3 C4 C9 -0.1(6) . . . . no
C13 C3 C4 C5 0.2(5) . . . . no
C13 C3 C4 C9 120.0(6) . . . . no
C2 C3 C12 C8 -0.2(6) . . . . no
C2 C3 C12 C9 -120.0(6) . . . . no
C4 C3 C12 C8 119.9(6) . . . . no
C4 C3 C12 C9 0.1(6) . . . . no
C13 C3 C12 C8 59.9(7) . . . . no
C13 C3 C12 C9 -59.9(7) . . . . no
C2 C3 C13 C1 0.2(5) . . . . no
C2 C3 C13 C5 120.0(6) . . . . no
C4 C3 C13 C1 -120.0(6) . . . . no
C4 C3 C13 C5 -0.2(5) . . . . no
C12 C3 C13 C1 -59.9(7) . . . . no
C12 C3 C13 C5 59.9(7) . . . . no
C3 C4 C5 C6 59.8(7) . . . . no
C3 C4 C5 C13 -0.2(5) . . . . no
C3 C4 C5 C14 119.9(5) . . . . no
C9 C4 C5 C6 -59.9(7) . . . . no
C9 C4 C5 C13 -120.0(5) . . . . no
C9 C4 C5 C14 0.2(5) . . . . no
C3 C4 C9 C7 -59.9(8) . . . . no
C3 C4 C9 C12 0.1(6) . . . . no
C3 C4 C9 C14 -120.0(5) . . . . no
C5 C4 C9 C7 59.9(8) . . . . no
C5 C4 C9 C12 119.9(6) . . . . no
C5 C4 C9 C14 -0.2(5) . . . . no
C4 C5 C6 C1 -59.8(7) . . . . no
C4 C5 C6 C10 59.8(7) . . . . no
C13 C5 C6 C1 0.2(5) . . . . no
C13 C5 C6 C10 119.9(5) . . . . no
C14 C5 C6 C1 -119.9(5) . . . . no
C14 C5 C6 C10 -0.2(5) . . . . no
C4 C5 C13 C1 119.9(5) . . . . no
C4 C5 C13 C3 0.2(5) . . . . no
C6 C5 C13 C1 -0.2(5) . . . . no
C6 C5 C13 C3 -120.0(5) . . . . no
C14 C5 C13 C1 59.9(7) . . . . no
C14 C5 C13 C3 -59.8(7) . . . . no
C4 C5 C14 C9 -0.2(5) . . . . no
C4 C5 C14 C10 -119.9(5) . . . . no
C6 C5 C14 C9 120.0(6) . . . . no
C6 C5 C14 C10 0.2(5) . . . . no
C13 C5 C14 C9 59.9(7) . . . . no
C13 C5 C14 C10 -59.9(7) . . . . no
C1 C6 C10 C7 59.9(7) . . . . no
C1 C6 C10 C11 -0.2(5) . . . . no
C1 C6 C10 C14 119.9(6) . . . . no
C5 C6 C10 C7 -59.8(7) . . . . no
C5 C6 C10 C11 -119.9(5) . . . . no
C5 C6 C10 C14 0.2(5) . . . . no
C9 C7 C8 C2 -59.9(7) . . . . no
C9 C7 C8 C11 -120.0(6) . . . . no
C9 C7 C8 C12 0.2(5) . . . . no
C10 C7 C8 C2 59.8(8) . . . . no
C10 C7 C8 C11 -0.2(5) . . . . no
C10 C7 C8 C12 119.9(5) . . . . no
C8 C7 C9 C4 59.9(7) . . . . no
C8 C7 C9 C12 -0.2(5) . . . . no
C8 C7 C9 C14 119.9(5) . . . . no
C10 C7 C9 C4 -59.8(9) . . . . no
C10 C7 C9 C12 -119.9(6) . . . . no
C10 C7 C9 C14 0.2(6) . . . . no
C8 C7 C10 C6 -59.9(7) . . . . no
C8 C7 C10 C11 0.2(5) . . . . no
C8 C7 C10 C14 -120.0(7) . . . . no
C9 C7 C10 C6 59.9(8) . . . . no
C9 C7 C10 C11 120.0(7) . . . . no
C9 C7 C10 C14 -0.2(6) . . . . no
C2 C8 C11 C1 -0.2(5) . . . . no
C2 C8 C11 C10 -120.0(4) . . . . no
C7 C8 C11 C1 120.0(5) . . . . no
C7 C8 C11 C10 0.2(5) . . . . no
C12 C8 C11 C1 59.9(8) . . . . no
C12 C8 C11 C10 -59.9(7) . . . . no
C2 C8 C12 C3 0.2(6) . . . . no
C2 C8 C12 C9 120.0(6) . . . . no
C7 C8 C12 C3 -120.0(5) . . . . no
C7 C8 C12 C9 -0.2(5) . . . . no
C11 C8 C12 C3 -59.8(8) . . . . no
C11 C8 C12 C9 60.0(7) . . . . no
C4 C9 C12 C3 -0.1(6) . . . . no
C4 C9 C12 C8 -119.9(5) . . . . no
C7 C9 C12 C3 119.9(5) . . . . no
C7 C9 C12 C8 0.2(5) . . . . no
C14 C9 C12 C3 59.8(8) . . . . no
C14 C9 C12 C8 -60.0(7) . . . . no
C4 C9 C14 C5 0.2(5) . . . . no
C4 C9 C14 C10 119.9(5) . . . . no
C7 C9 C14 C5 -119.9(6) . . . . no
C7 C9 C14 C10 -0.2(6) . . . . no
C12 C9 C14 C5 -59.8(7) . . . . no
C12 C9 C14 C10 59.9(8) . . . . no
C6 C10 C11 C1 0.2(5) . . . . no
C6 C10 C11 C8 120.0(5) . . . . no
C7 C10 C11 C1 -120.0(5) . . . . no
C7 C10 C11 C8 -0.2(5) . . . . no
C14 C10 C11 C1 -59.9(6) . . . . no
C14 C10 C11 C8 59.9(6) . . . . no
C6 C10 C14 C5 -0.2(5) . . . . no
C6 C10 C14 C9 -120.0(6) . . . . no
C7 C10 C14 C5 120.0(6) . . . . no
C7 C10 C14 C9 0.2(6) . . . . no
C11 C10 C14 C5 59.9(7) . . . . no
C11 C10 C14 C9 -59.9(7) . . . . no
O21 C21 C22 C23 62.4(6) . . . . no
O21 C21 C22 C23 -178.0(4) . . . 4_555 no
C26 C21 C22 C23 -59.8(3) . . . . no
O21 C21 C22 C23 178.0(4) 4_555 . . . no
O21 C21 C26 C25 -62.4(5) . . . . no
O21 C21 C26 C25 178.0(3) . . . 4_555 no
C22 C21 C26 C25 59.8(3) . . . . no
O21 C21 C26 C25 -178.0(3) 4_555 . . . no
C21 C22 C23 C24 59.9(5) . . . . no
C23 C22 C23 C24 -59.7(4) 4_555 . . . no
C22 C23 C24 C25 -59.9(3) . . . . no
C22 C23 C24 C27 59.8(5) . . . . no
C23 C24 C25 C26 59.9(3) . . . . no
C27 C24 C25 C26 -59.9(6) . . . . no
C23 C24 C27 C24 -59.7(4) . . . 4_555 no
C25 C24 C27 C24 59.9(5) . . . 4_555 no
C24 C25 C26 C21 -59.9(5) . . . . no
C24 C25 C26 C25 59.8(5) . . . 4_555 no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O15 C21 3.362(13) . 2_656 no
O15 C21 3.362(13) . 2_656 no
O16 O21 2.820(14) . . no
O16 C26 3.236(13) . . no
O16 C21 3.399(14) . . no
O21 C1 3.374(9) . 2_656 no
O21 O16 2.820(14) . . no
O15 H51 2.632(18) . . no
O15 H32 2.631(13) . . no
O16 H21 2.913(14) . . no
O16 H54 2.631(17) . . no
O16 H103 2.631(11) . . no
O16 H26 2.401(12) . . no
O21 H231 2.640(7) . . no
O21 H251 2.641(8) . . no
O21 H111 2.432(9) . . no
C1 O21 3.374(9) . 2_656 no
C2 C14 3.130(8) . . no
C4 C11 3.128(7) . . no
C6 C12 3.129(8) . . no
C7 C13 3.129(9) . . no
C11 C4 3.128(7) . . no
C12 C6 3.129(8) . . no
C13 C7 3.129(9) . . no
C14 C2 3.130(8) . . no
C21 O15 3.362(13) . 3_656 no
C21 O15 3.362(13) . 2_656 no
C21 O16 3.399(14) . 4_555 no
C21 O16 3.399(14) . . no
C26 O16 3.236(13) . 4_555 no
C26 O16 3.236(13) . . no
C1 H112 3.088(10) . 2_656 no
C3 H152 2.905(13) . . no
C8 H11 3.077(12) . 7_556 no
C26 H161 2.526(12) . . no
C26 H161 2.526(12) . 4_555 no
H2 H152 2.251(17) . . no
H4 H24 2.487(9) . 1_554 no
H6 H151 2.393(17) . . no
H6 H161 2.155(16) . . no
H6 H162 2.155(16) . . no
H6 H272 2.442(10) . 2_556 no
H6 H272 2.442(10) . 3_556 no
H11 H161 2.396(17) . . no
H11 C8 3.077(12) . 7_556 no
H12 H24 2.343(5) . 7_556 no
H13 H151 2.155(18) . . no
H13 H152 1.853(17) . . no
H13 H162 2.393(19) . . no
H14 H24 2.313(10) . 2_556 no
H21 O16 2.913(14) . . no
H21 H231 2.579(6) . . no
H21 H251 2.581(8) . . no
H24 H4 2.487(9) . 1_556 no
H24 H14 2.313(10) . 2_556 no
H24 H101 2.314(8) . 2_556 no
H24 H12 2.343(5) . 7_556 no
H26 O16 2.401(12) . . no
H26 H161 1.953(12) . . no
H26 H212 2.393(8) . . no
H26 O16 2.401(12) . 4_555 no
H26 H161 1.953(12) . 4_555 no
H26 H212 2.393(8) . 4_555 no
H31 H82 2.585(14) . . no
H31 H91 2.586(14) . . no
H32 O15 2.631(13) . . no
H32 H51 2.587(12) . . no
H32 H152 2.445(14) . . no
H33 H53 2.587(13) . . no
H33 H94 2.587(12) . . no
H34 H83 2.586(11) . . no
H34 H112 2.586(10) . . no
H34 H152 2.577(13) . . no
H51 O15 2.632(18) . . no
H51 H32 2.587(12) . . no
H51 H271 2.543(12) . 1_554 no
H51 H271 2.543(12) . 4_554 no
H52 H92 2.59(2) . . no
H52 H101 2.586(11) . . no
H53 H33 2.587(13) . . no
H53 H94 2.59(2) . . no
H53 H271 2.537(13) . 1_554 no
H53 H271 2.537(13) . 4_554 no
H54 O16 2.631(17) . . no
H54 H103 2.586(12) . . no
H54 H272 2.372(11) . 2_556 no
H54 H272 2.372(11) . 3_556 no
H81 H102 2.587(12) . . no
H81 H111 2.590(17) . . no
H82 H31 2.585(14) . . no
H82 H91 2.587(19) . . no
H82 H251 2.417(8) . 7_556 no
H83 H34 2.586(11) . . no
H83 H112 2.587(17) . . no
H84 H93 2.587(19) . . no
H84 H104 2.588(14) . . no
H84 H251 2.334(7) . 7_556 no
H91 H31 2.586(14) . . no
H91 H82 2.587(19) . . no
H91 H231 2.557(11) . 7_556 no
H92 H52 2.59(2) . . no
H92 H101 2.587(12) . . no
H93 H84 2.587(19) . . no
H93 H104 2.587(14) . . no
H93 H231 2.432(10) . 7_556 no
H94 H33 2.587(12) . . no
H94 H53 2.59(2) . . no
H101 H52 2.586(11) . . no
H101 H92 2.587(12) . . no
H101 H24 2.314(8) . 2_556 no
H102 H81 2.587(12) . . no
H102 H111 2.588(10) . . no
H103 O16 2.631(11) . . no
H103 H54 2.586(12) . . no
H103 H252 2.303(8) . 2_556 no
H104 H84 2.588(14) . . no
H104 H93 2.587(14) . . no
H111 O21 2.432(9) . . no
H111 H81 2.590(17) . . no
H111 H102 2.588(10) . . no
H111 H212 1.693(11) . . no
H112 H34 2.586(10) . . no
H112 H83 2.587(17) . . no
H112 H212 2.398(10) . . no
H112 C1 3.088(10) . 2_656 no
H151 C13 3.040(12) . 4_555 no
H151 H13 2.575(16) . 4_555 no
H151 H211 2.330(14) . 3_656 no
H151 H6 2.393(17) . . no
H151 H13 2.155(18) . . no
H152 C3 2.905(13) . . no
H152 H2 2.251(17) . . no
H152 H13 1.853(17) . . no
H152 H32 2.445(14) . . no
H152 H211 2.289(12) . 3_656 no
H152 O15 2.689(15) . 4_555 no
H152 H111 2.574(15) . 2_656 no
H152 O21 2.911(12) . 3_656 no
H152 H34 2.577(13) . . no
H161 C26 2.526(12) . . no
H161 H6 2.155(16) . . no
H161 H161 2.381(17) . 4_555 no
H161 H212 2.485(12) . 4_555 no
H161 H11 2.396(17) . . no
H161 H26 1.953(12) . . no
H161 O16 2.483(15) . 4_555 no
H162 H6 2.155(16) . . no
H162 H13 2.393(19) . . no
H162 C6 3.020(12) . 4_555 no
H162 H6 2.549(15) . 4_555 no
H162 H212 2.509(15) . 4_555 no
H211 H13 2.112(12) . 2_656 no
H211 H151 2.330(14) . 3_656 no
H211 H112 2.116(11) . 2_656 no
H211 O15 2.431(10) . 3_656 no
H211 C13 2.736(8) . 2_656 no
H211 H212 2.290(4) . 4_555 no
H211 H211 1.6717(10) . 4_555 no
H211 H152 2.289(12) . 3_656 no
H212 O15 2.486(13) . 2_656 no
H212 H112 2.398(10) . . no
H212 H161 2.485(12) . 4_555 no
H212 H112 2.475(10) . 2_656 no
H212 O16 2.859(11) . 4_555 no
H212 H212 2.1245(13) . 4_555 no
H212 H26 2.393(8) . . no
H212 H162 2.509(15) . 4_555 no
H212 H211 2.290(4) . 4_555 no
H212 H111 1.693(11) . . no
H231 O21 2.640(7) . . no
H231 H21 2.579(6) . . no
H231 H251 2.588(7) . . no
H231 H91 2.557(11) . 7_556 no
H231 H93 2.432(10) . 7_556 no
H232 H232 2.5855(15) . 4_555 no
H232 H271 2.587(8) . . no
H251 H82 2.417(8) . 7_556 no
H251 H84 2.334(7) . 7_556 no
H251 H21 2.581(8) . . no
H251 H231 2.588(7) . . no
H251 O21 2.641(8) . . no
H252 H272 2.588(6) . . no
H252 H252 2.484(6) . 2_556 no
H252 H252 2.5855(15) . 4_555 no
H252 H103 2.303(8) . 2_556 no
H271 H232 2.587(8) . . no
H271 H51 2.543(12) . 4_556 no
H271 H51 2.543(12) . 1_556 no
H271 H53 2.537(13) . 1_556 no
H271 H232 2.587(8) . 4_555 no
H271 H53 2.537(13) . 4_556 no
H272 H252 2.588(6) . 4_555 no
H272 H54 2.372(11) . 3_556 no
H272 H252 2.588(6) . . no
H272 H6 2.442(10) . 2_556 no
H272 H54 2.372(11) . 2_556 no
H272 H6 2.442(10) . 3_556 no

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O16 H161 O21 0.981(18) 1.900(13) 2.820(14) 154.9(11) . yes
O21 H212 O16 0.981(6) 1.880(14) 2.820(14) 159.4(7) . yes
O21 H211 O15 0.980(8) 1.465(13) 2.370(13) 150.9(4) 2_656 yes
O15 H152 O21 0.980(16) 1.467(12) 2.370(13) 150.6(13) 2_656 yes
O15 H151 O16 0.981(15) 1.764(14) 2.742(13) 174.7(15) 4_555 yes
O16 H162 O15 0.980(15) 1.768(14) 2.742(13) 171.6(13) 4_555 yes
C26 H26 O16 1.095(6) 2.401(12) 3.236(13) 131.8(5) . yes
C26 H26 O16 1.095(6) 2.401(12) 3.236(13) 131.8(5) 4_555 yes
C1 H111 O21 1.093(10) 2.432(9) 3.425(9) 150.4(10) . yes
