# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

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

data_zhaozhx_shj_181120
_database_code_depnum_ccdc_archive 'CCDC 1945205'
loop_
_audit_author_name
_audit_author_address
'Qingfeng Ruan'
;School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou, China
China
;
_audit_update_record             
;
2019-08-04 deposited with the CCDC.	2019-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(1S,3aR,4R,7R,8aS)-4-hydroxy-1,4-dimethyl-9-methyleneoctahydro-1H-3a,7-(epoxyethano)azulen-10-one
_chemical_name_common            'Guaianelactone A'
_chemical_melting_point          412.15-414.15
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.32

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   16.79540(10)
_cell_length_b                   10.61320(10)
_cell_length_c                   16.87830(10)
_cell_angle_alpha                90
_cell_angle_beta                 119.0570(10)
_cell_angle_gamma                90
_cell_volume                     2629.93(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       monoclinic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.692
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53491
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.995
_diffrn_reflns_theta_max         72.121
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10381
_reflns_number_gt                10096
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0462P)²+0.3345P] 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_abs_structure_details 
;
 Flack x determined using 4608 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         10381
_refine_ls_number_parameters     693
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
O001 O 0.38793(8) 0.64336(13) 0.47634(8) 0.0181(3) Uani 1 1 d . . . . .
O002 O 0.33609(9) 0.56528(13) 0.34135(9) 0.0220(3) Uani 1 1 d . . . . .
O003 O 0.50268(9) 0.86396(14) 0.15325(9) 0.0224(3) Uani 1 1 d . . . . .
O004 O 0.07618(8) 0.10905(12) 0.61584(8) 0.0179(3) Uani 1 1 d . . . . .
O005 O 0.10508(8) 0.11402(12) 0.09904(8) 0.0169(2) Uani 1 1 d . . . . .
O006 O 0.40492(8) 0.78692(13) 0.02238(8) 0.0181(3) Uani 1 1 d . . . . .
O007 O 0.50889(9) 0.91653(14) 0.61417(9) 0.0223(3) Uani 1 1 d . . . . .
H007 H 0.553988 0.958801 0.620762 0.033 Uiso 1 1 calc R U . . .
O008 O 0.09309(9) 0.39535(14) -0.03063(9) 0.0222(3) Uani 1 1 d . . . . .
H008 H 0.048547 0.434902 -0.071051 0.033 Uiso 1 1 calc R U . . .
O009 O 0.11522(9) 0.38195(14) 0.50822(9) 0.0245(3) Uani 1 1 d . . . . .
H009 H 0.082270 0.425661 0.462302 0.037 Uiso 1 1 calc R U . . .
O00A O 0.04734(10) 0.03600(15) 0.17857(9) 0.0269(3) Uani 1 1 d . . . . .
O00B O -0.02289(12) 0.02927(16) 0.64909(11) 0.0341(4) Uani 1 1 d . . . . .
O00C O 0.38718(10) 0.49730(16) -0.10180(11) 0.0325(4) Uani 1 1 d . . . . .
H00C H 0.424769 0.458455 -0.112109 0.049 Uiso 1 1 calc R U . . .
C00D C 0.33447(11) 0.65390(18) 0.38609(12) 0.0170(3) Uani 1 1 d . . . . .
C00E C 0.44722(12) 0.78116(18) 0.11345(12) 0.0177(3) Uani 1 1 d . . . . .
C00F C 0.09079(12) 0.12229(19) 0.17055(12) 0.0185(4) Uani 1 1 d . . . . .
C00G C 0.23438(11) 0.25389(17) 0.11855(12) 0.0168(3) Uani 1 1 d . . . . .
H00G H 0.239296 0.340406 0.097866 0.020 Uiso 1 1 calc R U . . .
C00H C 0.47597(12) 0.84067(18) 0.53385(12) 0.0187(4) Uani 1 1 d . . . . .
C00I C 0.06296(12) 0.31875(18) 0.01982(12) 0.0176(4) Uani 1 1 d . . . . .
C00J C 0.02580(13) 0.1184(2) 0.65760(12) 0.0210(4) Uani 1 1 d . . . . .
C00K C 0.27478(12) 0.76584(18) 0.34177(12) 0.0187(4) Uani 1 1 d . . . . .
C00L C 0.27260(12) 0.63269(19) -0.05209(13) 0.0212(4) Uani 1 1 d . . . . .
H00L H 0.269247 0.542373 -0.070336 0.025 Uiso 1 1 calc R U . . .
C00M C 0.25666(12) 0.86538(19) 0.39551(12) 0.0215(4) Uani 1 1 d . . . . .
H00M H 0.196497 0.904434 0.353445 0.026 Uiso 1 1 calc R U . . .
C00N C 0.05882(12) 0.30593(18) 0.53094(12) 0.0190(4) Uani 1 1 d . . . . .
C00O C 0.12811(13) 0.22690(19) 0.23882(12) 0.0210(4) Uani 1 1 d . . . . .
C00P C 0.42435(13) 0.92424(19) 0.45002(13) 0.0208(4) Uani 1 1 d . . . . .
H00A H 0.462565 0.999314 0.458130 0.025 Uiso 1 1 calc R U . . .
H00B H 0.419788 0.877229 0.397311 0.025 Uiso 1 1 calc R U . . .
C00Q C 0.12715(12) 0.20637(18) 0.59624(12) 0.0173(3) Uani 1 1 d . . . . .
C00R C 0.02952(12) 0.23064(19) 0.71383(12) 0.0195(4) Uani 1 1 d . . . . .
C00S C 0.35583(14) 0.5816(2) 0.11680(14) 0.0253(4) Uani 1 1 d . . . . .
H00S H 0.338023 0.547790 0.161280 0.030 Uiso 1 1 calc R U . . .
C00T C 0.20790(12) 0.26190(18) 0.68246(12) 0.0194(4) Uani 1 1 d . . . . .
H00T H 0.218485 0.348360 0.665905 0.023 Uiso 1 1 calc R U . . .
C00U C 0.29396(12) 0.16804(18) 0.09465(13) 0.0207(4) Uani 1 1 d . . . . .
H00U H 0.352839 0.211265 0.110936 0.025 Uiso 1 1 calc R U . . .
C00V C 0.23533(13) 0.1618(2) -0.00836(13) 0.0231(4) Uani 1 1 d . . . . .
H00D H 0.254561 0.091550 -0.033809 0.028 Uiso 1 1 calc R U . . .
H00E H 0.238580 0.241714 -0.036966 0.028 Uiso 1 1 calc R U . . .
C00W C 0.13512(11) 0.21121(18) 0.05628(11) 0.0161(3) Uani 1 1 d . . . . .
C00X C 0.10111(12) 0.33281(19) 0.74124(12) 0.0201(4) Uani 1 1 d . . . . .
H00X H 0.107475 0.372190 0.797857 0.024 Uiso 1 1 calc R U . . .
C00Y C -0.03275(12) 0.2668(2) -0.04222(13) 0.0216(4) Uani 1 1 d . . . . .
H00F H -0.076583 0.336419 -0.064270 0.032 Uiso 1 1 calc R U . . .
H00H H -0.049310 0.207341 -0.008199 0.032 Uiso 1 1 calc R U . . .
H00I H -0.033542 0.223406 -0.093851 0.032 Uiso 1 1 calc R U . . .
C00Z C 0.19453(12) 0.32446(18) 0.23971(12) 0.0192(4) Uani 1 1 d . . . . .
H00Z H 0.228348 0.358314 0.302875 0.023 Uiso 1 1 calc R U . . .
C010 C 0.42399(13) 0.6860(2) 0.16451(13) 0.0226(4) Uani 1 1 d . . . . .
C011 C 0.36200(12) 0.68567(18) -0.04560(12) 0.0192(4) Uani 1 1 d . . . . .
C012 C 0.55654(12) 0.7826(2) 0.52794(13) 0.0219(4) Uani 1 1 d . . . . .
H01A H 0.591734 0.849573 0.519270 0.033 Uiso 1 1 calc R U . . .
H01B H 0.533708 0.724055 0.476630 0.033 Uiso 1 1 calc R U . . .
H01C H 0.595658 0.737005 0.584159 0.033 Uiso 1 1 calc R U . . .
C013 C -0.01780(13) 0.2455(2) 0.44526(13) 0.0231(4) Uani 1 1 d . . . . .
H3AA H -0.057743 0.311536 0.404980 0.035 Uiso 1 1 calc R U . . .
H H -0.053194 0.188747 0.462069 0.035 Uiso 1 1 calc R U . . .
HA H 0.008557 0.197596 0.413978 0.035 Uiso 1 1 calc R U . . .
C014 C 0.13908(12) 0.13972(19) -0.02212(12) 0.0201(4) Uani 1 1 d . . . . .
H2BA H 0.127900 0.048624 -0.019503 0.024 Uiso 1 1 calc R U . . .
HB H 0.092681 0.173005 -0.081610 0.024 Uiso 1 1 calc R U . . .
C015 C -0.03527(14) 0.2370(2) 0.73734(13) 0.0242(4) Uani 1 1 d . . . . .
C016 C 0.41763(12) 0.73889(18) 0.54906(11) 0.0176(4) Uani 1 1 d . . . . .
C017 C 0.23911(13) 0.7748(2) 0.25234(13) 0.0237(4) Uani 1 1 d . . . . .
C018 C 0.33554(14) 0.7157(2) 0.63680(13) 0.0249(4) Uani 1 1 d . . . . .
H018 H 0.309267 0.768334 0.667593 0.030 Uiso 1 1 calc R U . . .
C019 C 0.33827(12) 0.79320(19) 0.56049(12) 0.0200(4) Uani 1 1 d . . . . .
H019 H 0.357254 0.880252 0.585200 0.024 Uiso 1 1 calc R U . . .
C01A C 0.43478(13) 0.58258(19) -0.02788(14) 0.0232(4) Uani 1 1 d . . . . .
C01B C 0.19447(12) 0.2775(2) 0.76470(12) 0.0214(4) Uani 1 1 d . . . . .
H5AA H 0.242750 0.333429 0.809010 0.026 Uiso 1 1 calc R U . . .
HC H 0.201203 0.194333 0.793847 0.026 Uiso 1 1 calc R U . . .
C01C C 0.51890(13) 0.6369(2) -0.02889(14) 0.0275(4) Uani 1 1 d . . . . .
H01Q H 0.563565 0.569720 -0.015966 0.041 Uiso 1 1 calc R U . . .
H01R H 0.545982 0.702846 0.017354 0.041 Uiso 1 1 calc R U . . .
H01S H 0.500902 0.672999 -0.088696 0.041 Uiso 1 1 calc R U . . .
C01D C 0.47471(12) 0.66202(19) 0.63706(12) 0.0214(4) Uani 1 1 d . . . . .
H01F H 0.468477 0.570595 0.623746 0.026 Uiso 1 1 calc R U . . .
H01G H 0.539906 0.685058 0.664794 0.026 Uiso 1 1 calc R U . . .
C01E C 0.01269(13) 0.38917(19) 0.57157(13) 0.0214(4) Uani 1 1 d . . . . .
H6AA H -0.013006 0.463462 0.531605 0.026 Uiso 1 1 calc R U . . .
HD H -0.039297 0.341055 0.568348 0.026 Uiso 1 1 calc R U . . .
C01F C 0.32872(13) 0.97094(19) 0.42476(13) 0.0227(4) Uani 1 1 d . . . . .
H01H H 0.309060 1.032486 0.374633 0.027 Uiso 1 1 calc R U . . .
H01I H 0.331408 1.015598 0.477495 0.027 Uiso 1 1 calc R U . . .
C01G C 0.24779(12) 0.8074(2) 0.47413(13) 0.0227(4) Uani 1 1 d . . . . .
H01J H 0.207089 0.861073 0.486827 0.027 Uiso 1 1 calc R U . . .
H01K H 0.218924 0.723423 0.455433 0.027 Uiso 1 1 calc R U . . .
C01H C 0.26525(12) 0.26513(18) 0.21899(12) 0.0191(4) Uani 1 1 d . . . . .
H3BA H 0.321505 0.316486 0.247964 0.023 Uiso 1 1 calc R U . . .
HE H 0.280477 0.180065 0.246439 0.023 Uiso 1 1 calc R U . . .
C01I C 0.29199(13) 0.1827(2) 0.69955(13) 0.0256(4) Uani 1 1 d . . . . .
H7AA H 0.348816 0.233035 0.735165 0.031 Uiso 1 1 calc R U . . .
C01J C 0.05675(12) 0.40015(19) 0.09189(13) 0.0204(4) Uani 1 1 d . . . . .
H4BA H 0.024543 0.478861 0.061980 0.024 Uiso 1 1 calc R U . . .
HF H 0.017639 0.354879 0.111361 0.024 Uiso 1 1 calc R U . . .
C01K C 0.43712(14) 0.6951(2) 0.70095(13) 0.0262(4) Uani 1 1 d . . . . .
H01L H 0.447120 0.625234 0.743680 0.031 Uiso 1 1 calc R U . . .
H01M H 0.466028 0.772445 0.735925 0.031 Uiso 1 1 calc R U . . .
C01L C 0.33037(13) 0.7538(2) -0.13709(12) 0.0242(4) Uani 1 1 d . . . . .
H01T H 0.334375 0.846270 -0.128424 0.029 Uiso 1 1 calc R U . . .
H01U H 0.368809 0.728851 -0.164083 0.029 Uiso 1 1 calc R U . . .
C01M C 0.14405(13) 0.43706(18) 0.17705(13) 0.0204(4) Uani 1 1 d . . . . .
H5BA H 0.128982 0.499028 0.211610 0.024 Uiso 1 1 calc R U . . .
HG H 0.185479 0.478786 0.158956 0.024 Uiso 1 1 calc R U . . .
C01N C 0.06887(14) 0.43747(19) 0.66859(13) 0.0236(4) Uani 1 1 d . . . . .
H8AA H 0.031872 0.498972 0.680856 0.028 Uiso 1 1 calc R U . . .
HH H 0.122918 0.482469 0.673980 0.028 Uiso 1 1 calc R U . . .
C01O C 0.17302(12) 0.1316(2) 0.55001(12) 0.0217(4) Uani 1 1 d . . . . .
H9AA H 0.164047 0.039929 0.553026 0.026 Uiso 1 1 calc R U . . .
HI H 0.146803 0.156469 0.485601 0.026 Uiso 1 1 calc R U . . .
C01P C 0.26856(12) 0.6323(2) 0.03601(13) 0.0236(4) Uani 1 1 d . . . . .
H01V H 0.216353 0.580025 0.027996 0.028 Uiso 1 1 calc R U . . .
H01W H 0.257740 0.719405 0.049618 0.028 Uiso 1 1 calc R U . . .
C01Q C 0.23165(14) 0.7136(2) -0.19833(14) 0.0295(4) Uani 1 1 d . . . . .
H01X H 0.228623 0.632600 -0.228746 0.035 Uiso 1 1 calc R U . . .
H01Y H 0.197872 0.778392 -0.244948 0.035 Uiso 1 1 calc R U . . .
C01R C 0.31283(14) 0.0370(2) 0.13743(14) 0.0264(4) Uani 1 1 d . . . . .
H6BA H 0.351350 0.044401 0.203234 0.040 Uiso 1 1 calc R U . . .
HJ H 0.344137 -0.014172 0.112604 0.040 Uiso 1 1 calc R U . . .
HK H 0.255119 -0.003441 0.123886 0.040 Uiso 1 1 calc R U . . .
C01S C 0.46890(13) 0.5122(2) 0.06235(15) 0.0270(4) Uani 1 1 d . . . . .
H01Z H 0.500985 0.435528 0.059495 0.032 Uiso 1 1 calc R U . . .
HL H 0.514844 0.566345 0.110710 0.032 Uiso 1 1 calc R U . . .
C01T C 0.19334(13) 0.7001(2) -0.13309(14) 0.0258(4) Uani 1 1 d . . . . .
H01 H 0.138679 0.643906 -0.160486 0.031 Uiso 1 1 calc R U . . .
C01U C 0.29979(15) 0.0564(2) 0.74623(15) 0.0321(5) Uani 1 1 d . . . . .
H0BA H 0.314576 0.071107 0.809237 0.048 Uiso 1 1 calc R U . . .
HM H 0.348046 0.005972 0.745008 0.048 Uiso 1 1 calc R U . . .
HN H 0.241751 0.011235 0.714376 0.048 Uiso 1 1 calc R U . . .
C01V C 0.27453(13) 0.1649(2) 0.60256(14) 0.0279(4) Uani 1 1 d . . . . .
H1BA H 0.312312 0.095763 0.599093 0.033 Uiso 1 1 calc R U . . .
HO H 0.287455 0.243211 0.579030 0.033 Uiso 1 1 calc R U . . .
C01W C 0.46605(16) 0.6988(3) 0.25402(15) 0.0325(5) Uani 1 1 d . . . . .
C01X C 0.40017(15) 0.4717(2) 0.09238(16) 0.0298(5) Uani 1 1 d . . . . .
H1AA H 0.431359 0.415871 0.145815 0.036 Uiso 1 1 calc R U . . .
HP H 0.351477 0.421895 0.043048 0.036 Uiso 1 1 calc R U . . .
C01Y C 0.28369(16) 0.5917(2) 0.60631(16) 0.0331(5) Uani 1 1 d . . . . .
H01N H 0.218852 0.608978 0.566454 0.050 Uiso 1 1 calc R U . . .
H01O H 0.291450 0.544436 0.659464 0.050 Uiso 1 1 calc R U . . .
H01P H 0.307407 0.542057 0.573394 0.050 Uiso 1 1 calc R U . . .
C01Z C 0.16738(15) 0.8282(2) -0.11054(16) 0.0336(5) Uani 1 1 d . . . . .
H2AA H 0.143498 0.816344 -0.068373 0.050 Uiso 1 1 calc R U . . .
HQ H 0.120679 0.867730 -0.166304 0.050 Uiso 1 1 calc R U . . .
HR H 0.221355 0.882412 -0.082493 0.050 Uiso 1 1 calc R U . . .
C020 C 0.09962(19) 0.2294(3) 0.29980(17) 0.0378(6) Uani 1 1 d . . . . .
H01D H 0.2514(18) 0.712(3) 0.2171(17) 0.029(6) Uiso 1 1 d . . . . .
H0AA H 0.5091(19) 0.765(3) 0.2840(17) 0.030(6) Uiso 1 1 d . . . . .
H01E H 0.2007(18) 0.848(3) 0.2208(17) 0.029(6) Uiso 1 1 d . . . . .
H4AA H -0.0812(19) 0.173(3) 0.7213(18) 0.030(6) Uiso 1 1 d . . . . .
HS H 0.455(2) 0.638(3) 0.292(2) 0.040(7) Uiso 1 1 d . . . . .
HT H -0.0358(19) 0.305(3) 0.7741(19) 0.034(7) Uiso 1 1 d . . . . .
H02A H 0.123(2) 0.293(4) 0.349(2) 0.047(8) Uiso 1 1 d . . . . .
H02B H 0.058(2) 0.169(3) 0.298(2) 0.045(8) Uiso 1 1 d . . . . .


_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
O001 C00D 1.346(2) . ?
O001 C016 1.479(2) . ?
O002 C00D 1.215(2) . ?
O003 C00E 1.218(2) . ?
O004 C00J 1.342(2) . ?
O004 C00Q 1.478(2) . ?
O005 C00F 1.343(2) . ?
O005 C00W 1.481(2) . ?
O006 C00E 1.345(2) . ?
O006 C011 1.479(2) . ?
O007 C00H 1.437(2) . ?
O007 H007 0.8400 . ?
O008 C00I 1.435(2) . ?
O008 H008 0.8400 . ?
O009 C00N 1.431(2) . ?
O009 H009 0.8400 . ?
O00A C00F 1.219(2) . ?
O00B C00J 1.213(3) . ?
O00C C01A 1.430(2) . ?
O00C H00C 0.8400 . ?
C00D C00K 1.499(3) . ?
C00E C010 1.497(3) . ?
C00F C00O 1.501(3) . ?
C00G C01H 1.517(2) . ?
C00G C00U 1.545(2) . ?
C00G C00W 1.545(2) . ?
C00G H00G 1.0000 . ?
C00H C00P 1.533(3) . ?
C00H C012 1.534(3) . ?
C00H C016 1.561(2) . ?
C00I C00Y 1.533(2) . ?
C00I C01J 1.536(3) . ?
C00I C00W 1.558(2) . ?
C00J C00R 1.505(3) . ?
C00K C017 1.330(3) . ?
C00K C00M 1.516(3) . ?
C00L C01P 1.521(3) . ?
C00L C01T 1.544(3) . ?
C00L C011 1.557(2) . ?
C00L H00L 1.0000 . ?
C00M C01G 1.534(3) . ?
C00M C01F 1.544(3) . ?
C00M H00M 1.0000 . ?
C00N C013 1.533(3) . ?
C00N C01E 1.538(3) . ?
C00N C00Q 1.556(2) . ?
C00O C020 1.329(3) . ?
C00O C00Z 1.517(3) . ?
C00P C01F 1.530(3) . ?
C00P H00A 0.9900 . ?
C00P H00B 0.9900 . ?
C00Q C00T 1.545(2) . ?
C00Q C01O 1.554(2) . ?
C00R C015 1.329(3) . ?
C00R C00X 1.515(3) . ?
C00S C010 1.514(3) . ?
C00S C01P 1.535(3) . ?
C00S C01X 1.544(3) . ?
C00S H00S 1.0000 . ?
C00T C01B 1.519(2) . ?
C00T C01I 1.545(3) . ?
C00T H00T 1.0000 . ?
C00U C00V 1.528(3) . ?
C00U C01R 1.528(3) . ?
C00U H00U 1.0000 . ?
C00V C014 1.536(3) . ?
C00V H00D 0.9900 . ?
C00V H00E 0.9900 . ?
C00W C014 1.555(2) . ?
C00X C01B 1.535(3) . ?
C00X C01N 1.545(3) . ?
C00X H00X 1.0000 . ?
C00Y H00F 0.9800 . ?
C00Y H00H 0.9800 . ?
C00Y H00I 0.9800 . ?
C00Z C01H 1.527(3) . ?
C00Z C01M 1.547(3) . ?
C00Z H00Z 1.0000 . ?
C010 C01W 1.328(3) . ?
C011 C01L 1.547(3) . ?
C011 C01A 1.557(3) . ?
C012 H01A 0.9800 . ?
C012 H01B 0.9800 . ?
C012 H01C 0.9800 . ?
C013 H3AA 0.9800 . ?
C013 H 0.9800 . ?
C013 HA 0.9800 . ?
C014 H2BA 0.9900 . ?
C014 HB 0.9900 . ?
C015 H4AA 0.96(3) . ?
C015 HT 0.96(3) . ?
C016 C019 1.548(2) . ?
C016 C01D 1.552(2) . ?
C017 H01D 0.98(3) . ?
C017 H01E 0.99(3) . ?
C018 C01Y 1.522(3) . ?
C018 C01K 1.528(3) . ?
C018 C019 1.548(3) . ?
C018 H018 1.0000 . ?
C019 C01G 1.518(3) . ?
C019 H019 1.0000 . ?
C01A C01C 1.534(3) . ?
C01A C01S 1.536(3) . ?
C01B H5AA 0.9900 . ?
C01B HC 0.9900 . ?
C01C H01Q 0.9800 . ?
C01C H01R 0.9800 . ?
C01C H01S 0.9800 . ?
C01D C01K 1.532(3) . ?
C01D H01F 0.9900 . ?
C01D H01G 0.9900 . ?
C01E C01N 1.528(3) . ?
C01E H6AA 0.9900 . ?
C01E HD 0.9900 . ?
C01F H01H 0.9900 . ?
C01F H01I 0.9900 . ?
C01G H01J 0.9900 . ?
C01G H01K 0.9900 . ?
C01H H3BA 0.9900 . ?
C01H HE 0.9900 . ?
C01I C01U 1.528(3) . ?
C01I C01V 1.528(3) . ?
C01I H7AA 1.0000 . ?
C01J C01M 1.524(3) . ?
C01J H4BA 0.9900 . ?
C01J HF 0.9900 . ?
C01K H01L 0.9900 . ?
C01K H01M 0.9900 . ?
C01L C01Q 1.528(3) . ?
C01L H01T 0.9900 . ?
C01L H01U 0.9900 . ?
C01M H5BA 0.9900 . ?
C01M HG 0.9900 . ?
C01N H8AA 0.9900 . ?
C01N HH 0.9900 . ?
C01O C01V 1.532(3) . ?
C01O H9AA 0.9900 . ?
C01O HI 0.9900 . ?
C01P H01V 0.9900 . ?
C01P H01W 0.9900 . ?
C01Q C01T 1.528(3) . ?
C01Q H01X 0.9900 . ?
C01Q H01Y 0.9900 . ?
C01R H6BA 0.9800 . ?
C01R HJ 0.9800 . ?
C01R HK 0.9800 . ?
C01S C01X 1.530(3) . ?
C01S H01Z 0.9900 . ?
C01S HL 0.9900 . ?
C01T C01Z 1.531(3) . ?
C01T H01 1.0000 . ?
C01U H0BA 0.9800 . ?
C01U HM 0.9800 . ?
C01U HN 0.9800 . ?
C01V H1BA 0.9900 . ?
C01V HO 0.9900 . ?
C01W H0AA 0.96(3) . ?
C01W HS 0.99(3) . ?
C01X H1AA 0.9900 . ?
C01X HP 0.9900 . ?
C01Y H01N 0.9800 . ?
C01Y H01O 0.9800 . ?
C01Y H01P 0.9800 . ?
C01Z H2AA 0.9800 . ?
C01Z HQ 0.9800 . ?
C01Z HR 0.9800 . ?
C020 H02A 0.99(3) . ?
C020 H02B 0.93(4) . ?

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
C00D O001 C016 130.77(14) . . ?
C00J O004 C00Q 130.32(15) . . ?
C00F O005 C00W 130.12(14) . . ?
C00E O006 C011 129.89(15) . . ?
C00H O007 H007 109.5 . . ?
C00I O008 H008 109.5 . . ?
C00N O009 H009 109.5 . . ?
C01A O00C H00C 109.5 . . ?
O002 C00D O001 115.81(16) . . ?
O002 C00D C00K 120.98(16) . . ?
O001 C00D C00K 123.20(16) . . ?
O003 C00E O006 115.81(16) . . ?
O003 C00E C010 120.83(16) . . ?
O006 C00E C010 123.21(16) . . ?
O00A C00F O005 115.39(17) . . ?
O00A C00F C00O 121.33(16) . . ?
O005 C00F C00O 123.24(16) . . ?
C01H C00G C00U 115.14(15) . . ?
C01H C00G C00W 116.97(14) . . ?
C00U C00G C00W 105.74(14) . . ?
C01H C00G H00G 106.1 . . ?
C00U C00G H00G 106.1 . . ?
C00W C00G H00G 106.1 . . ?
O007 C00H C00P 109.43(16) . . ?
O007 C00H C012 109.84(15) . . ?
C00P C00H C012 107.10(15) . . ?
O007 C00H C016 102.54(13) . . ?
C00P C00H C016 115.69(15) . . ?
C012 C00H C016 112.12(16) . . ?
O008 C00I C00Y 110.70(14) . . ?
O008 C00I C01J 109.29(15) . . ?
C00Y C00I C01J 106.93(15) . . ?
O008 C00I C00W 102.62(13) . . ?
C00Y C00I C00W 111.28(15) . . ?
C01J C00I C00W 115.99(14) . . ?
O00B C00J O004 116.16(18) . . ?
O00B C00J C00R 120.74(17) . . ?
O004 C00J C00R 123.10(17) . . ?
C017 C00K C00D 116.51(17) . . ?
C017 C00K C00M 121.24(18) . . ?
C00D C00K C00M 122.24(15) . . ?
C01P C00L C01T 115.97(16) . . ?
C01P C00L C011 115.57(15) . . ?
C01T C00L C011 106.39(15) . . ?
C01P C00L H00L 106.0 . . ?
C01T C00L H00L 106.0 . . ?
C011 C00L H00L 106.0 . . ?
C00K C00M C01G 111.71(16) . . ?
C00K C00M C01F 110.05(15) . . ?
C01G C00M C01F 113.89(15) . . ?
C00K C00M H00M 106.9 . . ?
C01G C00M H00M 106.9 . . ?
C01F C00M H00M 106.9 . . ?
O009 C00N C013 110.16(14) . . ?
O009 C00N C01E 109.74(16) . . ?
C013 C00N C01E 106.67(15) . . ?
O009 C00N C00Q 102.49(14) . . ?
C013 C00N C00Q 112.12(16) . . ?
C01E C00N C00Q 115.61(14) . . ?
C020 C00O C00F 115.87(18) . . ?
C020 C00O C00Z 121.20(18) . . ?
C00F C00O C00Z 122.93(16) . . ?
C01F C00P C00H 119.43(15) . . ?
C01F C00P H00A 107.5 . . ?
C00H C00P H00A 107.5 . . ?
C01F C00P H00B 107.5 . . ?
C00H C00P H00B 107.5 . . ?
H00A C00P H00B 107.0 . . ?
O004 C00Q C00T 113.24(14) . . ?
O004 C00Q C01O 103.77(14) . . ?
C00T C00Q C01O 104.19(14) . . ?
O004 C00Q C00N 108.97(14) . . ?
C00T C00Q C00N 114.60(15) . . ?
C01O C00Q C00N 111.47(14) . . ?
C015 C00R C00J 116.05(18) . . ?
C015 C00R C00X 121.08(18) . . ?
C00J C00R C00X 122.86(16) . . ?
C010 C00S C01P 111.40(17) . . ?
C010 C00S C01X 110.91(16) . . ?
C01P C00S C01X 113.84(18) . . ?
C010 C00S H00S 106.7 . . ?
C01P C00S H00S 106.7 . . ?
C01X C00S H00S 106.7 . . ?
C01B C00T C00Q 116.75(15) . . ?
C01B C00T C01I 114.61(15) . . ?
C00Q C00T C01I 105.84(15) . . ?
C01B C00T H00T 106.3 . . ?
C00Q C00T H00T 106.3 . . ?
C01I C00T H00T 106.3 . . ?
C00V C00U C01R 111.70(17) . . ?
C00V C00U C00G 100.45(14) . . ?
C01R C00U C00G 115.19(15) . . ?
C00V C00U H00U 109.7 . . ?
C01R C00U H00U 109.7 . . ?
C00G C00U H00U 109.7 . . ?
C00U C00V C014 103.18(14) . . ?
C00U C00V H00D 111.1 . . ?
C014 C00V H00D 111.1 . . ?
C00U C00V H00E 111.1 . . ?
C014 C00V H00E 111.1 . . ?
H00D C00V H00E 109.1 . . ?
O005 C00W C00G 112.52(13) . . ?
O005 C00W C014 103.91(14) . . ?
C00G C00W C014 104.13(14) . . ?
O005 C00W C00I 108.61(13) . . ?
C00G C00W C00I 115.43(15) . . ?
C014 C00W C00I 111.60(14) . . ?
C00R C00X C01B 111.40(16) . . ?
C00R C00X C01N 110.62(15) . . ?
C01B C00X C01N 113.57(16) . . ?
C00R C00X H00X 107.0 . . ?
C01B C00X H00X 107.0 . . ?
C01N C00X H00X 107.0 . . ?
C00I C00Y H00F 109.5 . . ?
C00I C00Y H00H 109.5 . . ?
H00F C00Y H00H 109.5 . . ?
C00I C00Y H00I 109.5 . . ?
H00F C00Y H00I 109.5 . . ?
H00H C00Y H00I 109.5 . . ?
C00O C00Z C01H 111.49(16) . . ?
C00O C00Z C01M 111.36(15) . . ?
C01H C00Z C01M 113.00(15) . . ?
C00O C00Z H00Z 106.9 . . ?
C01H C00Z H00Z 106.9 . . ?
C01M C00Z H00Z 106.9 . . ?
C01W C010 C00E 116.27(19) . . ?
C01W C010 C00S 121.81(18) . . ?
C00E C010 C00S 121.92(17) . . ?
O006 C011 C01L 103.69(15) . . ?
O006 C011 C00L 114.03(14) . . ?
C01L C011 C00L 104.28(15) . . ?
O006 C011 C01A 108.66(14) . . ?
C01L C011 C01A 112.14(15) . . ?
C00L C011 C01A 113.58(16) . . ?
C00H C012 H01A 109.5 . . ?
C00H C012 H01B 109.5 . . ?
H01A C012 H01B 109.5 . . ?
C00H C012 H01C 109.5 . . ?
H01A C012 H01C 109.5 . . ?
H01B C012 H01C 109.5 . . ?
C00N C013 H3AA 109.5 . . ?
C00N C013 H 109.5 . . ?
H3AA C013 H 109.5 . . ?
C00N C013 HA 109.5 . . ?
H3AA C013 HA 109.5 . . ?
H C013 HA 109.5 . . ?
C00V C014 C00W 105.89(14) . . ?
C00V C014 H2BA 110.6 . . ?
C00W C014 H2BA 110.6 . . ?
C00V C014 HB 110.6 . . ?
C00W C014 HB 110.6 . . ?
H2BA C014 HB 108.7 . . ?
C00R C015 H4AA 122.7(16) . . ?
C00R C015 HT 119.9(17) . . ?
H4AA C015 HT 117(2) . . ?
O001 C016 C019 113.25(14) . . ?
O001 C016 C01D 103.68(14) . . ?
C019 C016 C01D 104.21(14) . . ?
O001 C016 C00H 108.88(13) . . ?
C019 C016 C00H 114.21(16) . . ?
C01D C016 C00H 112.08(14) . . ?
C00K C017 H01D 122.0(16) . . ?
C00K C017 H01E 119.1(15) . . ?
H01D C017 H01E 119(2) . . ?
C01Y C018 C01K 111.98(19) . . ?
C01Y C018 C019 114.91(17) . . ?
C01K C018 C019 101.04(15) . . ?
C01Y C018 H018 109.5 . . ?
C01K C018 H018 109.5 . . ?
C019 C018 H018 109.5 . . ?
C01G C019 C018 115.55(16) . . ?
C01G C019 C016 115.99(15) . . ?
C018 C019 C016 106.32(16) . . ?
C01G C019 H019 106.1 . . ?
C018 C019 H019 106.1 . . ?
C016 C019 H019 106.1 . . ?
O00C C01A C01C 110.85(16) . . ?
O00C C01A C01S 109.79(17) . . ?
C01C C01A C01S 106.97(16) . . ?
O00C C01A C011 102.88(15) . . ?
C01C C01A C011 112.02(17) . . ?
C01S C01A C011 114.35(16) . . ?
C00T C01B C00X 113.10(15) . . ?
C00T C01B H5AA 109.0 . . ?
C00X C01B H5AA 109.0 . . ?
C00T C01B HC 109.0 . . ?
C00X C01B HC 109.0 . . ?
H5AA C01B HC 107.8 . . ?
C01A C01C H01Q 109.5 . . ?
C01A C01C H01R 109.5 . . ?
H01Q C01C H01R 109.5 . . ?
C01A C01C H01S 109.5 . . ?
H01Q C01C H01S 109.5 . . ?
H01R C01C H01S 109.5 . . ?
C01K C01D C016 106.22(16) . . ?
C01K C01D H01F 110.5 . . ?
C016 C01D H01F 110.5 . . ?
C01K C01D H01G 110.5 . . ?
C016 C01D H01G 110.5 . . ?
H01F C01D H01G 108.7 . . ?
C01N C01E C00N 119.20(16) . . ?
C01N C01E H6AA 107.5 . . ?
C00N C01E H6AA 107.5 . . ?
C01N C01E HD 107.5 . . ?
C00N C01E HD 107.5 . . ?
H6AA C01E HD 107.0 . . ?
C00P C01F C00M 114.07(16) . . ?
C00P C01F H01H 108.7 . . ?
C00M C01F H01H 108.7 . . ?
C00P C01F H01I 108.7 . . ?
C00M C01F H01I 108.7 . . ?
H01H C01F H01I 107.6 . . ?
C019 C01G C00M 113.44(15) . . ?
C019 C01G H01J 108.9 . . ?
C00M C01G H01J 108.9 . . ?
C019 C01G H01K 108.9 . . ?
C00M C01G H01K 108.9 . . ?
H01J C01G H01K 107.7 . . ?
C00G C01H C00Z 113.98(14) . . ?
C00G C01H H3BA 108.8 . . ?
C00Z C01H H3BA 108.8 . . ?
C00G C01H HE 108.8 . . ?
C00Z C01H HE 108.8 . . ?
H3BA C01H HE 107.7 . . ?
C01U C01I C01V 111.55(18) . . ?
C01U C01I C00T 114.52(17) . . ?
C01V C01I C00T 100.66(15) . . ?
C01U C01I H7AA 109.9 . . ?
C01V C01I H7AA 109.9 . . ?
C00T C01I H7AA 109.9 . . ?
C01M C01J C00I 119.16(15) . . ?
C01M C01J H4BA 107.5 . . ?
C00I C01J H4BA 107.5 . . ?
C01M C01J HF 107.5 . . ?
C00I C01J HF 107.5 . . ?
H4BA C01J HF 107.0 . . ?
C018 C01K C01D 103.53(15) . . ?
C018 C01K H01L 111.1 . . ?
C01D C01K H01L 111.1 . . ?
C018 C01K H01M 111.1 . . ?
C01D C01K H01M 111.1 . . ?
H01L C01K H01M 109.0 . . ?
C01Q C01L C011 106.18(16) . . ?
C01Q C01L H01T 110.5 . . ?
C011 C01L H01T 110.5 . . ?
C01Q C01L H01U 110.5 . . ?
C011 C01L H01U 110.5 . . ?
H01T C01L H01U 108.7 . . ?
C01J C01M C00Z 113.76(16) . . ?
C01J C01M H5BA 108.8 . . ?
C00Z C01M H5BA 108.8 . . ?
C01J C01M HG 108.8 . . ?
C00Z C01M HG 108.8 . . ?
H5BA C01M HG 107.7 . . ?
C01E C01N C00X 113.93(16) . . ?
C01E C01N H8AA 108.8 . . ?
C00X C01N H8AA 108.8 . . ?
C01E C01N HH 108.8 . . ?
C00X C01N HH 108.8 . . ?
H8AA C01N HH 107.7 . . ?
C01V C01O C00Q 105.98(15) . . ?
C01V C01O H9AA 110.5 . . ?
C00Q C01O H9AA 110.5 . . ?
C01V C01O HI 110.5 . . ?
C00Q C01O HI 110.5 . . ?
H9AA C01O HI 108.7 . . ?
C00L C01P C00S 113.11(16) . . ?
C00L C01P H01V 109.0 . . ?
C00S C01P H01V 109.0 . . ?
C00L C01P H01W 109.0 . . ?
C00S C01P H01W 109.0 . . ?
H01V C01P H01W 107.8 . . ?
C01L C01Q C01T 103.71(16) . . ?
C01L C01Q H01X 111.0 . . ?
C01T C01Q H01X 111.0 . . ?
C01L C01Q H01Y 111.0 . . ?
C01T C01Q H01Y 111.0 . . ?
H01X C01Q H01Y 109.0 . . ?
C00U C01R H6BA 109.5 . . ?
C00U C01R HJ 109.5 . . ?
H6BA C01R HJ 109.5 . . ?
C00U C01R HK 109.5 . . ?
H6BA C01R HK 109.5 . . ?
HJ C01R HK 109.5 . . ?
C01X C01S C01A 119.13(17) . . ?
C01X C01S H01Z 107.5 . . ?
C01A C01S H01Z 107.5 . . ?
C01X C01S HL 107.5 . . ?
C01A C01S HL 107.5 . . ?
H01Z C01S HL 107.0 . . ?
C01Q C01T C01Z 111.49(19) . . ?
C01Q C01T C00L 101.41(15) . . ?
C01Z C01T C00L 114.73(17) . . ?
C01Q C01T H01 109.6 . . ?
C01Z C01T H01 109.6 . . ?
C00L C01T H01 109.6 . . ?
C01I C01U H0BA 109.5 . . ?
C01I C01U HM 109.5 . . ?
H0BA C01U HM 109.5 . . ?
C01I C01U HN 109.5 . . ?
H0BA C01U HN 109.5 . . ?
HM C01U HN 109.5 . . ?
C01I C01V C01O 103.26(15) . . ?
C01I C01V H1BA 111.1 . . ?
C01O C01V H1BA 111.1 . . ?
C01I C01V HO 111.1 . . ?
C01O C01V HO 111.1 . . ?
H1BA C01V HO 109.1 . . ?
C010 C01W H0AA 121.6(16) . . ?
C010 C01W HS 120.8(18) . . ?
H0AA C01W HS 118(2) . . ?
C01S C01X C00S 114.55(17) . . ?
C01S C01X H1AA 108.6 . . ?
C00S C01X H1AA 108.6 . . ?
C01S C01X HP 108.6 . . ?
C00S C01X HP 108.6 . . ?
H1AA C01X HP 107.6 . . ?
C018 C01Y H01N 109.5 . . ?
C018 C01Y H01O 109.5 . . ?
H01N C01Y H01O 109.5 . . ?
C018 C01Y H01P 109.5 . . ?
H01N C01Y H01P 109.5 . . ?
H01O C01Y H01P 109.5 . . ?
C01T C01Z H2AA 109.5 . . ?
C01T C01Z HQ 109.5 . . ?
H2AA C01Z HQ 109.5 . . ?
C01T C01Z HR 109.5 . . ?
H2AA C01Z HR 109.5 . . ?
HQ C01Z HR 109.5 . . ?
C00O C020 H02A 121.2(19) . . ?
C00O C020 H02B 120(2) . . ?
H02A C020 H02B 118(3) . . ?

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
C016 O001 C00D O002 166.07(16) . . . . ?
C016 O001 C00D C00K -14.9(3) . . . . ?
C011 O006 C00E O003 155.19(16) . . . . ?
C011 O006 C00E C010 -29.3(3) . . . . ?
C00W O005 C00F O00A 164.38(16) . . . . ?
C00W O005 C00F C00O -17.9(3) . . . . ?
C00Q O004 C00J O00B 166.05(17) . . . . ?
C00Q O004 C00J C00R -15.2(3) . . . . ?
O002 C00D C00K C017 -13.3(3) . . . . ?
O001 C00D C00K C017 167.74(17) . . . . ?
O002 C00D C00K C00M 167.61(17) . . . . ?
O001 C00D C00K C00M -11.3(3) . . . . ?
C017 C00K C00M C01G 143.58(18) . . . . ?
C00D C00K C00M C01G -37.4(2) . . . . ?
C017 C00K C00M C01F -88.9(2) . . . . ?
C00D C00K C00M C01F 90.2(2) . . . . ?
O00A C00F C00O C020 -9.7(3) . . . . ?
O005 C00F C00O C020 172.8(2) . . . . ?
O00A C00F C00O C00Z 170.12(18) . . . . ?
O005 C00F C00O C00Z -7.4(3) . . . . ?
O007 C00H C00P C01F -75.1(2) . . . . ?
C012 C00H C00P C01F 165.89(17) . . . . ?
C016 C00H C00P C01F 40.1(2) . . . . ?
C00J O004 C00Q C00T 65.6(2) . . . . ?
C00J O004 C00Q C01O 177.93(16) . . . . ?
C00J O004 C00Q C00N -63.2(2) . . . . ?
O009 C00N C00Q O004 -172.05(13) . . . . ?
C013 C00N C00Q O004 -53.94(18) . . . . ?
C01E C00N C00Q O004 68.63(19) . . . . ?
O009 C00N C00Q C00T 59.91(18) . . . . ?
C013 C00N C00Q C00T 178.01(15) . . . . ?
C01E C00N C00Q C00T -59.4(2) . . . . ?
O009 C00N C00Q C01O -58.11(18) . . . . ?
C013 C00N C00Q C01O 59.99(19) . . . . ?
C01E C00N C00Q C01O -177.44(15) . . . . ?
O00B C00J C00R C015 -12.9(3) . . . . ?
O004 C00J C00R C015 168.39(18) . . . . ?
O00B C00J C00R C00X 168.24(19) . . . . ?
O004 C00J C00R C00X -10.4(3) . . . . ?
O004 C00Q C00T C01B -35.9(2) . . . . ?
C01O C00Q C00T C01B -147.93(17) . . . . ?
C00N C00Q C00T C01B 90.0(2) . . . . ?
O004 C00Q C00T C01I 93.03(17) . . . . ?
C01O C00Q C00T C01I -19.05(19) . . . . ?
C00N C00Q C00T C01I -141.11(15) . . . . ?
C01H C00G C00U C00V 171.02(15) . . . . ?
C00W C00G C00U C00V 40.28(17) . . . . ?
C01H C00G C00U C01R 50.9(2) . . . . ?
C00W C00G C00U C01R -79.87(18) . . . . ?
C01R C00U C00V C014 77.85(19) . . . . ?
C00G C00U C00V C014 -44.78(18) . . . . ?
C00F O005 C00W C00G 67.3(2) . . . . ?
C00F O005 C00W C014 179.32(15) . . . . ?
C00F O005 C00W C00I -61.8(2) . . . . ?
C01H C00G C00W O005 -37.8(2) . . . . ?
C00U C00G C00W O005 91.92(17) . . . . ?
C01H C00G C00W C014 -149.65(15) . . . . ?
C00U C00G C00W C014 -19.97(18) . . . . ?
C01H C00G C00W C00I 87.66(19) . . . . ?
C00U C00G C00W C00I -142.65(15) . . . . ?
O008 C00I C00W O005 -171.87(13) . . . . ?
C00Y C00I C00W O005 -53.45(18) . . . . ?
C01J C00I C00W O005 69.07(18) . . . . ?
O008 C00I C00W C00G 60.71(17) . . . . ?
C00Y C00I C00W C00G 179.13(15) . . . . ?
C01J C00I C00W C00G -58.3(2) . . . . ?
O008 C00I C00W C014 -57.91(17) . . . . ?
C00Y C00I C00W C014 60.52(19) . . . . ?
C01J C00I C00W C014 -176.97(15) . . . . ?
C015 C00R C00X C01B 142.90(18) . . . . ?
C00J C00R C00X C01B -38.3(2) . . . . ?
C015 C00R C00X C01N -89.8(2) . . . . ?
C00J C00R C00X C01N 89.0(2) . . . . ?
C020 C00O C00Z C01H 139.8(2) . . . . ?
C00F C00O C00Z C01H -39.9(2) . . . . ?
C020 C00O C00Z C01M -93.0(2) . . . . ?
C00F C00O C00Z C01M 87.3(2) . . . . ?
O003 C00E C010 C01W 0.9(3) . . . . ?
O006 C00E C010 C01W -174.36(19) . . . . ?
O003 C00E C010 C00S -179.56(17) . . . . ?
O006 C00E C010 C00S 5.2(3) . . . . ?
C01P C00S C010 C01W 132.4(2) . . . . ?
C01X C00S C010 C01W -99.7(2) . . . . ?
C01P C00S C010 C00E -47.1(2) . . . . ?
C01X C00S C010 C00E 80.8(2) . . . . ?
C00E O006 C011 C01L -177.37(15) . . . . ?
C00E O006 C011 C00L 69.9(2) . . . . ?
C00E O006 C011 C01A -57.9(2) . . . . ?
C01P C00L C011 O006 -32.4(2) . . . . ?
C01T C00L C011 O006 97.94(18) . . . . ?
C01P C00L C011 C01L -144.75(17) . . . . ?
C01T C00L C011 C01L -14.45(19) . . . . ?
C01P C00L C011 C01A 92.9(2) . . . . ?
C01T C00L C011 C01A -136.83(16) . . . . ?
C00U C00V C014 C00W 33.4(2) . . . . ?
O005 C00W C014 C00V -126.08(15) . . . . ?
C00G C00W C014 C00V -8.09(19) . . . . ?
C00I C00W C014 C00V 117.07(16) . . . . ?
C00D O001 C016 C019 65.4(2) . . . . ?
C00D O001 C016 C01D 177.76(15) . . . . ?
C00D O001 C016 C00H -62.8(2) . . . . ?
O007 C00H C016 O001 -173.10(13) . . . . ?
C00P C00H C016 O001 67.88(19) . . . . ?
C012 C00H C016 O001 -55.34(18) . . . . ?
O007 C00H C016 C019 59.23(18) . . . . ?
C00P C00H C016 C019 -59.8(2) . . . . ?
C012 C00H C016 C019 176.99(15) . . . . ?
O007 C00H C016 C01D -58.99(18) . . . . ?
C00P C00H C016 C01D -178.02(15) . . . . ?
C012 C00H C016 C01D 58.77(19) . . . . ?
C01Y C018 C019 C01G 46.6(2) . . . . ?
C01K C018 C019 C01G 167.35(17) . . . . ?
C01Y C018 C019 C016 -83.6(2) . . . . ?
C01K C018 C019 C016 37.10(19) . . . . ?
O001 C016 C019 C01G -34.8(2) . . . . ?
C01D C016 C019 C01G -146.73(17) . . . . ?
C00H C016 C019 C01G 90.6(2) . . . . ?
O001 C016 C019 C018 95.25(17) . . . . ?
C01D C016 C019 C018 -16.73(19) . . . . ?
C00H C016 C019 C018 -139.35(15) . . . . ?
O006 C011 C01A O00C -175.25(15) . . . . ?
C01L C011 C01A O00C -61.22(19) . . . . ?
C00L C011 C01A O00C 56.7(2) . . . . ?
O006 C011 C01A C01C -56.2(2) . . . . ?
C01L C011 C01A C01C 57.9(2) . . . . ?
C00L C011 C01A C01C 175.79(16) . . . . ?
O006 C011 C01A C01S 65.76(19) . . . . ?
C01L C011 C01A C01S 179.79(16) . . . . ?
C00L C011 C01A C01S -62.3(2) . . . . ?
C00Q C00T C01B C00X -43.8(2) . . . . ?
C01I C00T C01B C00X -168.33(16) . . . . ?
C00R C00X C01B C00T 86.5(2) . . . . ?
C01N C00X C01B C00T -39.2(2) . . . . ?
O001 C016 C01D C01K -128.97(15) . . . . ?
C019 C016 C01D C01K -10.24(19) . . . . ?
C00H C016 C01D C01K 113.77(17) . . . . ?
O009 C00N C01E C01N -75.1(2) . . . . ?
C013 C00N C01E C01N 165.58(17) . . . . ?
C00Q C00N C01E C01N 40.2(2) . . . . ?
C00H C00P C01F C00M -66.2(2) . . . . ?
C00K C00M C01F C00P -36.8(2) . . . . ?
C01G C00M C01F C00P 89.6(2) . . . . ?
C018 C019 C01G C00M -170.35(17) . . . . ?
C016 C019 C01G C00M -44.9(2) . . . . ?
C00K C00M C01G C019 87.3(2) . . . . ?
C01F C00M C01G C019 -38.1(2) . . . . ?
C00U C00G C01H C00Z -166.61(15) . . . . ?
C00W C00G C01H C00Z -41.5(2) . . . . ?
C00O C00Z C01H C00G 85.66(19) . . . . ?
C01M C00Z C01H C00G -40.7(2) . . . . ?
C01B C00T C01I C01U 49.7(2) . . . . ?
C00Q C00T C01I C01U -80.40(19) . . . . ?
C01B C00T C01I C01V 169.52(17) . . . . ?
C00Q C00T C01I C01V 39.38(19) . . . . ?
O008 C00I C01J C01M -75.8(2) . . . . ?
C00Y C00I C01J C01M 164.31(16) . . . . ?
C00W C00I C01J C01M 39.5(2) . . . . ?
C01Y C018 C01K C01D 79.8(2) . . . . ?
C019 C018 C01K C01D -43.0(2) . . . . ?
C016 C01D C01K C018 33.7(2) . . . . ?
O006 C011 C01L C01Q -131.77(16) . . . . ?
C00L C011 C01L C01Q -12.1(2) . . . . ?
C01A C011 C01L C01Q 111.19(18) . . . . ?
C00I C01J C01M C00Z -66.8(2) . . . . ?
C00O C00Z C01M C01J -35.1(2) . . . . ?
C01H C00Z C01M C01J 91.32(19) . . . . ?
C00N C01E C01N C00X -66.7(2) . . . . ?
C00R C00X C01N C01E -35.6(2) . . . . ?
C01B C00X C01N C01E 90.5(2) . . . . ?
O004 C00Q C01O C01V -127.48(16) . . . . ?
C00T C00Q C01O C01V -8.7(2) . . . . ?
C00N C00Q C01O C01V 115.39(17) . . . . ?
C01T C00L C01P C00S -171.41(17) . . . . ?
C011 C00L C01P C00S -45.9(2) . . . . ?
C010 C00S C01P C00L 89.6(2) . . . . ?
C01X C00S C01P C00L -36.7(2) . . . . ?
C011 C01L C01Q C01T 34.5(2) . . . . ?
O00C C01A C01S C01X -72.6(2) . . . . ?
C01C C01A C01S C01X 167.03(18) . . . . ?
C011 C01A C01S C01X 42.4(2) . . . . ?
C01L C01Q C01T C01Z 80.1(2) . . . . ?
C01L C01Q C01T C00L -42.5(2) . . . . ?
C01P C00L C01T C01Q 165.28(17) . . . . ?
C011 C00L C01T C01Q 35.21(19) . . . . ?
C01P C00L C01T C01Z 45.0(2) . . . . ?
C011 C00L C01T C01Z -85.1(2) . . . . ?
C01U C01I C01V C01O 77.6(2) . . . . ?
C00T C01I C01V C01O -44.3(2) . . . . ?
C00Q C01O C01V C01I 33.5(2) . . . . ?
C01A C01S C01X C00S -67.7(3) . . . . ?
C010 C00S C01X C01S -37.4(2) . . . . ?
C01P C00S C01X C01S 89.2(2) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/methanol (9:1)'
_chemical_compound_source        'Lindera glauca?Lindera?Lauraceae'
_chemical_properties_physical    Efflorescent
####################################################################### 
# 
# 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_zzx_shj_181113
_database_code_depnum_ccdc_archive 'CCDC 1945206'
loop_
_audit_author_name
_audit_author_address
'Qingfeng Ruan'
;School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou, China
China
;
_audit_update_record             
;
2019-08-04 deposited with the CCDC.	2019-12-23 downloaded from the CCDC.
;
_audit_creation_date             2018-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            'Guaianelactone C'
_chemical_name_systematic        
(4R,7S,7aS,10R,10aR)-10-hydroxy-7,10-dimethyl-3-methyleneoctahydro-4,10a-methanocyclopenta[b]oxonin-2(3H)-one
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.32
_chemical_absolute_configuration ad
_chemical_melting_point          418.15-419.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   9.72709(4)
_cell_length_b                   9.72709(4)
_cell_length_c                   28.60837(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2706.82(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    25792
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.8010
_cell_measurement_theta_min      4.7790
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.824
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tetragonal
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            28910
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.071
_diffrn_reflns_theta_min         4.802
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  -1.00   0.50    0.05    --  -46.62  94.00-117.00   50
  2  ω     11.00  36.00   0.50    0.05    --   46.62 -38.00-114.00   50
  3  ω     52.00  77.00   0.50    0.05    --   46.62  38.00  40.00   50
  4  ω      7.00  32.00   0.50    0.05    --   46.62-100.00  37.00   50
  5  ω    -25.00  44.00   0.50    0.05    --   46.62 -94.00 131.00  138
  6  ω    -92.00 -67.00   0.50    0.10    -- -100.00  94.00-117.00   50
  7  ω   -151.00-126.00   0.50    0.10    -- -100.00 -94.00 131.00   50
  8  ω   -154.00-129.00   0.50    0.10    -- -100.00 -38.00-114.00   50
  9  ω    111.00 137.00   0.50    0.10    --  107.00  38.00  40.00   52
 10  ω     35.00  86.00   0.50    0.10    --  107.00 -94.00 131.00  102
 11  ω     77.00 108.00   0.50    0.10    --  107.00 -38.00-114.00   62
 12  ω    104.00 134.00   0.50    0.10    --  107.00 100.00 142.00   60
 13  ω    126.00 152.00   0.50    0.10    --  107.00  94.00-117.00   52
 14  ω     35.00  64.00   0.50    0.05    --   46.62  57.00 150.00   58
 15  ω     32.00 119.00   0.50    0.05    --   46.62  38.00 120.00  174
 16  ω     75.00 120.00   0.50    0.05    --   46.62  77.00-180.00   90
 17  ω     26.00  69.00   0.50    0.05    --   46.62  77.00-180.00   86
 18  ω   -104.00 -78.00   0.50    0.10    -- -100.00 -73.00 153.98   52
 19  ω   -111.00 -75.00   0.50    0.10    -- -100.00 -79.00 170.04   72
 20  ω   -104.00 -78.00   0.50    0.10    -- -100.00 -72.00 178.37   52
 21  ω   -154.00-128.00   0.50    0.10    -- -100.00 -77.00 150.00   52
 22  ω   -102.00 -76.00   0.50    0.10    -- -100.00 -77.00-180.00   52
 23  ω   -105.00 -79.00   0.50    0.10    -- -100.00 -77.00 150.00   52
 24  ω   -172.00 -81.00   0.50    0.10    -- -100.00 -65.00 122.13  182
 25  ω   -157.00-127.00   0.50    0.10    -- -100.00 -55.00 151.17   60
 26  ω   -164.00 -81.00   0.50    0.10    -- -100.00 -66.00 148.59  166
 27  ω   -103.00 -77.00   0.50    0.10    -- -100.00 -78.00 154.44   52
 28  ω   -167.00 -85.00   0.50    0.10    -- -100.00 -45.00   0.00  164
 29  ω   -154.00-122.00   0.50    0.10    -- -100.00 -77.00-180.00   64
 30  ω   -102.00 -76.00   0.50    0.10    -- -100.00 -77.00 120.00   52
 31  ω   -123.00 -87.00   0.50    0.10    -- -100.00 -55.00 151.17   72
 32  ω   -115.00 -80.00   0.50    0.10    -- -100.00 -70.00 135.90   70
 33  ω     36.00 121.00   0.50    0.10    --  107.00 -45.00  30.00  170
 34  ω     93.00 176.00   0.50    0.10    --  107.00  45.00 -90.00  166
 35  ω     34.00 109.00   0.50    0.10    --  107.00 -94.00 -30.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1460968000
_diffrn_orient_matrix_UB_12      0.0004073000
_diffrn_orient_matrix_UB_13      -0.0208342000
_diffrn_orient_matrix_UB_21      0.0185865000
_diffrn_orient_matrix_UB_22      0.1505538000
_diffrn_orient_matrix_UB_23      0.0154601000
_diffrn_orient_matrix_UB_31      0.0583392000
_diffrn_orient_matrix_UB_32      -0.0491144000
_diffrn_orient_matrix_UB_33      0.0471830000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.636
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2616
_reflns_number_total             2656
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1018 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2656
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+0.4839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0690
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C008(H008), C00A(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00H,H00I), C00E(H00J,H00K), C00G(H00N,H00O), C00H(H00P,H00Q), C00I(H00R,
 H00S)
2.c Idealised Me refined as rotating group:
 C006(H00A,H00B,H00C), C00B(H00E,H00F,H00G)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.55056(9) 0.93319(9) 0.39427(3) 0.0157(2) Uani 1 1 d . . . . .
O002 O 0.67726(10) 1.05730(10) 0.34759(3) 0.0208(2) Uani 1 1 d . . . . .
O003 O 0.27057(11) 0.71282(11) 0.42772(4) 0.0234(2) Uani 1 1 d . . . . .
H003 H 0.249133 0.634346 0.420203 0.035 Uiso 1 1 calc GR . . . .
C004 C 0.56861(14) 1.04644(14) 0.36860(4) 0.0167(3) Uani 1 1 d . . . . .
C005 C 0.40702(15) 0.74140(15) 0.41180(5) 0.0185(3) Uani 1 1 d . . . . .
C006 C 0.42643(16) 0.69414(15) 0.36151(5) 0.0222(3) Uani 1 1 d . . . . .
H00A H 0.412071 0.596650 0.359631 0.033 Uiso 1 1 calc GR . . . .
H00B H 0.518081 0.715626 0.351433 0.033 Uiso 1 1 calc GR . . . .
H00C H 0.361381 0.740323 0.341758 0.033 Uiso 1 1 calc GR . . . .
C007 C 0.54771(15) 1.02903(15) 0.48947(5) 0.0206(3) Uani 1 1 d . . . . .
H007 H 0.531349 1.038070 0.523130 0.025 Uiso 1 1 calc R . . . .
C008 C 0.45004(15) 0.91322(15) 0.47305(5) 0.0191(3) Uani 1 1 d . . . . .
H008 H 0.360500 0.933132 0.487218 0.023 Uiso 1 1 calc R . . . .
C009 C 0.42343(14) 0.89849(14) 0.41968(5) 0.0168(3) Uani 1 1 d . . . . .
C00A C 0.33972(15) 1.13606(15) 0.40048(5) 0.0206(3) Uani 1 1 d . . . . .
H00D H 0.260557 1.185310 0.387488 0.025 Uiso 1 1 calc R . . . .
C00B C 0.70207(16) 1.00077(16) 0.48462(5) 0.0238(3) Uani 1 1 d . . . . .
H00E H 0.724775 0.917353 0.500807 0.036 Uiso 1 1 calc GR . . . .
H00F H 0.752984 1.075797 0.497876 0.036 Uiso 1 1 calc GR . . . .
H00G H 0.725128 0.991471 0.452148 0.036 Uiso 1 1 calc GR . . . .
C00C C 0.45755(15) 1.15218(15) 0.36685(5) 0.0194(3) Uani 1 1 d . . . . .
C00D C 0.51119(16) 0.68134(15) 0.44608(5) 0.0224(3) Uani 1 1 d . . . . .
H00H H 0.604157 0.690550 0.434218 0.027 Uiso 1 1 calc R . . . .
H00I H 0.492499 0.584979 0.452060 0.027 Uiso 1 1 calc R . . . .
C00E C 0.30377(15) 0.98326(15) 0.40180(5) 0.0198(3) Uani 1 1 d . . . . .
H00J H 0.224778 0.969340 0.421944 0.024 Uiso 1 1 calc R . . . .
H00K H 0.279302 0.952668 0.370620 0.024 Uiso 1 1 calc R . . . .
C00F C 0.46815(18) 1.25183(16) 0.33517(6) 0.0256(3) Uani 1 1 d . . . . .
C00G C 0.49096(17) 0.76745(16) 0.49035(5) 0.0244(3) Uani 1 1 d . . . . .
H00N H 0.575284 0.771175 0.508402 0.029 Uiso 1 1 calc R . . . .
H00O H 0.418898 0.728617 0.509709 0.029 Uiso 1 1 calc R . . . .
C00H C 0.37219(17) 1.19934(16) 0.44892(5) 0.0253(3) Uani 1 1 d . . . . .
H00P H 0.359318 1.298036 0.446800 0.030 Uiso 1 1 calc R . . . .
H00Q H 0.305228 1.164751 0.471120 0.030 Uiso 1 1 calc R . . . .
C00I C 0.51565(17) 1.17233(15) 0.46869(5) 0.0236(3) Uani 1 1 d . . . . .
H00R H 0.532597 1.240019 0.492912 0.028 Uiso 1 1 calc R . . . .
H00S H 0.581502 1.189484 0.443903 0.028 Uiso 1 1 calc R . . . .
H00L H 0.397(2) 1.321(2) 0.3329(7) 0.031(5) Uiso 1 1 d . . . . .
H00M H 0.548(2) 1.255(2) 0.3141(7) 0.030(5) Uiso 1 1 d . . . . .


_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
O001 C004 1.3356(16) . ?
O001 C009 1.4736(16) . ?
O002 C004 1.2203(17) . ?
O003 H003 0.8200 . ?
O003 C005 1.4305(17) . ?
C004 C00C 1.4925(19) . ?
C005 C006 1.5220(19) . ?
C005 C009 1.5528(19) . ?
C005 C00D 1.526(2) . ?
C006 H00A 0.9600 . ?
C006 H00B 0.9600 . ?
C006 H00C 0.9600 . ?
C007 H007 0.9800 . ?
C007 C008 1.547(2) . ?
C007 C00B 1.533(2) . ?
C007 C00I 1.547(2) . ?
C008 H008 0.9800 . ?
C008 C009 1.5552(18) . ?
C008 C00G 1.554(2) . ?
C009 C00E 1.5154(19) . ?
C00A H00D 0.9800 . ?
C00A C00C 1.505(2) . ?
C00A C00E 1.527(2) . ?
C00A C00H 1.549(2) . ?
C00B H00E 0.9600 . ?
C00B H00F 0.9600 . ?
C00B H00G 0.9600 . ?
C00C C00F 1.331(2) . ?
C00D H00H 0.9700 . ?
C00D H00I 0.9700 . ?
C00D C00G 1.531(2) . ?
C00E H00J 0.9700 . ?
C00E H00K 0.9700 . ?
C00F H00L 0.97(2) . ?
C00F H00M 0.98(2) . ?
C00G H00N 0.9700 . ?
C00G H00O 0.9700 . ?
C00H H00P 0.9700 . ?
C00H H00Q 0.9700 . ?
C00H C00I 1.529(2) . ?
C00I H00R 0.9700 . ?
C00I H00S 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C004 O001 C009 124.79(11) . . ?
C005 O003 H003 109.5 . . ?
O001 C004 C00C 119.45(12) . . ?
O002 C004 O001 117.13(12) . . ?
O002 C004 C00C 123.42(13) . . ?
O003 C005 C006 110.94(12) . . ?
O003 C005 C009 103.91(11) . . ?
O003 C005 C00D 109.69(12) . . ?
C006 C005 C009 114.95(12) . . ?
C006 C005 C00D 114.17(13) . . ?
C00D C005 C009 102.42(11) . . ?
C005 C006 H00A 109.5 . . ?
C005 C006 H00B 109.5 . . ?
C005 C006 H00C 109.5 . . ?
H00A C006 H00B 109.5 . . ?
H00A C006 H00C 109.5 . . ?
H00B C006 H00C 109.5 . . ?
C008 C007 H007 105.3 . . ?
C008 C007 C00I 114.57(12) . . ?
C00B C007 H007 105.3 . . ?
C00B C007 C008 116.34(12) . . ?
C00B C007 C00I 108.92(12) . . ?
C00I C007 H007 105.3 . . ?
C007 C008 H008 106.0 . . ?
C007 C008 C009 117.87(11) . . ?
C007 C008 C00G 114.25(12) . . ?
C009 C008 H008 106.0 . . ?
C00G C008 H008 106.0 . . ?
C00G C008 C009 105.74(11) . . ?
O001 C009 C005 103.89(10) . . ?
O001 C009 C008 108.88(11) . . ?
O001 C009 C00E 110.69(11) . . ?
C005 C009 C008 104.50(11) . . ?
C00E C009 C005 114.05(12) . . ?
C00E C009 C008 114.14(11) . . ?
C00C C00A H00D 107.8 . . ?
C00C C00A C00E 106.95(11) . . ?
C00C C00A C00H 112.04(12) . . ?
C00E C00A H00D 107.8 . . ?
C00E C00A C00H 114.28(12) . . ?
C00H C00A H00D 107.8 . . ?
C007 C00B H00E 109.5 . . ?
C007 C00B H00F 109.5 . . ?
C007 C00B H00G 109.5 . . ?
H00E C00B H00F 109.5 . . ?
H00E C00B H00G 109.5 . . ?
H00F C00B H00G 109.5 . . ?
C004 C00C C00A 117.28(12) . . ?
C00F C00C C004 117.94(14) . . ?
C00F C00C C00A 124.77(14) . . ?
C005 C00D H00H 111.0 . . ?
C005 C00D H00I 111.0 . . ?
C005 C00D C00G 103.70(12) . . ?
H00H C00D H00I 109.0 . . ?
C00G C00D H00H 111.0 . . ?
C00G C00D H00I 111.0 . . ?
C009 C00E C00A 111.23(12) . . ?
C009 C00E H00J 109.4 . . ?
C009 C00E H00K 109.4 . . ?
C00A C00E H00J 109.4 . . ?
C00A C00E H00K 109.4 . . ?
H00J C00E H00K 108.0 . . ?
C00C C00F H00L 119.7(12) . . ?
C00C C00F H00M 119.9(12) . . ?
H00L C00F H00M 120.4(17) . . ?
C008 C00G H00N 110.6 . . ?
C008 C00G H00O 110.6 . . ?
C00D C00G C008 105.59(11) . . ?
C00D C00G H00N 110.6 . . ?
C00D C00G H00O 110.6 . . ?
H00N C00G H00O 108.8 . . ?
C00A C00H H00P 108.1 . . ?
C00A C00H H00Q 108.1 . . ?
H00P C00H H00Q 107.3 . . ?
C00I C00H C00A 116.68(12) . . ?
C00I C00H H00P 108.1 . . ?
C00I C00H H00Q 108.1 . . ?
C007 C00I H00R 107.6 . . ?
C007 C00I H00S 107.6 . . ?
C00H C00I C007 118.76(13) . . ?
C00H C00I H00R 107.6 . . ?
C00H C00I H00S 107.6 . . ?
H00R C00I H00S 107.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C004 C00C C00A 9.67(19) . . . . ?
O001 C004 C00C C00F -168.91(13) . . . . ?
O001 C009 C00E C00A -50.46(14) . . . . ?
O002 C004 C00C C00A -170.29(12) . . . . ?
O002 C004 C00C C00F 11.1(2) . . . . ?
O003 C005 C009 O001 -168.23(10) . . . . ?
O003 C005 C009 C008 77.68(13) . . . . ?
O003 C005 C009 C00E -47.63(14) . . . . ?
O003 C005 C00D C00G -67.09(14) . . . . ?
C004 O001 C009 C005 139.73(11) . . . . ?
C004 O001 C009 C008 -109.34(13) . . . . ?
C004 O001 C009 C00E 16.91(16) . . . . ?
C005 C009 C00E C00A -167.17(11) . . . . ?
C005 C00D C00G C008 -32.68(15) . . . . ?
C006 C005 C009 O001 -46.81(15) . . . . ?
C006 C005 C009 C008 -160.91(12) . . . . ?
C006 C005 C009 C00E 73.78(16) . . . . ?
C006 C005 C00D C00G 167.70(12) . . . . ?
C007 C008 C009 O001 35.18(16) . . . . ?
C007 C008 C009 C005 145.69(12) . . . . ?
C007 C008 C009 C00E -89.06(15) . . . . ?
C007 C008 C00G C00D -121.61(13) . . . . ?
C008 C007 C00I C00H 20.27(18) . . . . ?
C008 C009 C00E C00A 72.80(15) . . . . ?
C009 O001 C004 O002 -176.20(11) . . . . ?
C009 O001 C004 C00C 3.84(18) . . . . ?
C009 C005 C00D C00G 42.80(14) . . . . ?
C009 C008 C00G C00D 9.66(15) . . . . ?
C00A C00H C00I C007 -76.03(18) . . . . ?
C00B C007 C008 C009 -79.11(16) . . . . ?
C00B C007 C008 C00G 45.97(16) . . . . ?
C00B C007 C00I C00H 152.52(13) . . . . ?
C00C C00A C00E C009 62.03(14) . . . . ?
C00C C00A C00H C00I -42.62(19) . . . . ?
C00D C005 C009 O001 77.57(12) . . . . ?
C00D C005 C009 C008 -36.52(14) . . . . ?
C00D C005 C009 C00E -161.83(11) . . . . ?
C00E C00A C00C C004 -41.23(16) . . . . ?
C00E C00A C00C C00F 137.25(15) . . . . ?
C00E C00A C00H C00I 79.24(17) . . . . ?
C00G C008 C009 O001 -93.99(13) . . . . ?
C00G C008 C009 C005 16.52(14) . . . . ?
C00G C008 C009 C00E 141.77(12) . . . . ?
C00H C00A C00C C004 84.73(15) . . . . ?
C00H C00A C00C C00F -96.79(17) . . . . ?
C00H C00A C00E C009 -62.58(15) . . . . ?
C00I C007 C008 C009 49.51(18) . . . . ?
C00I C007 C008 C00G 174.58(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.723
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/methanol/water (9:1:0.5)'
_chemical_compound_source        'Lindera glauca, Lindera, Lauraceae'
_chemical_properties_physical    Efflorescent
