# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_AP_4
_database_code_depnum_ccdc_archive 'CCDC 1866974'
loop_
_audit_author_name
_audit_author_address
'Zhang Jia'
;Beijing University of Chinese Medicine
China
;
_audit_update_record             
;
2018-09-11 deposited with the CCDC.	2019-02-14 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         ?
_chemical_formula_sum            'C9.23 H13.23 O3.69'
_chemical_formula_weight         183.27

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   32.1461(4)
_cell_length_b                   11.48300(10)
_cell_length_c                   8.01620(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2959.05(6)
_cell_formula_units_Z            13
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    20279
_cell_measurement_theta_min      2.7210
_cell_measurement_theta_max      73.4170

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             1276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.862
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67547
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27626
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.749
_diffrn_reflns_theta_max         73.611
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5896
_reflns_number_gt                5815
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    ?
_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)+(0.0451P)²+1.6619P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5896
_refine_ls_number_parameters     393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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
C11 C 0.36132(8) 0.5750(2) 0.5739(3) 0.0164(5) Uani 1 1 d . . . . .
O1 O 0.32540(5) 0.65210(16) 0.2690(2) 0.0188(4) Uani 1 1 d . . . . .
H2 H 0.3187 0.6300 0.1754 0.028 Uiso 1 1 calc R U . . .
O2 O 0.34770(6) 0.59318(16) 0.7138(2) 0.0217(4) Uani 1 1 d . . . . .
O3 O 0.33914(6) 0.37576(15) 0.5970(2) 0.0181(4) Uani 1 1 d . . . . .
H4 H 0.3432 0.3895 0.6961 0.027 Uiso 1 1 calc R U . . .
O4 O 0.37468(6) 0.50278(15) 0.0662(2) 0.0183(4) Uani 1 1 d . . . . .
O5 O 0.35057(6) 0.34629(17) -0.0695(2) 0.0240(4) Uani 1 1 d . . . . .
O6 O 0.40867(6) 0.24143(16) 0.5062(3) 0.0220(4) Uani 1 1 d . . . . .
H7 H 0.4237 0.2408 0.5889 0.033 Uiso 1 1 calc R U . . .
O7 O 0.43293(6) 0.19184(18) 0.7878(3) 0.0288(5) Uani 1 1 d . . . . .
O8 O 0.33963(6) -0.05004(17) 0.8225(2) 0.0254(4) Uani 1 1 d . . . . .
O9 O 0.29770(6) 0.03908(16) 0.2660(3) 0.0242(4) Uani 1 1 d . . . . .
H10 H 0.2873 -0.0260 0.2723 0.036 Uiso 1 1 calc R U . . .
C1 C 0.42604(8) 0.7454(2) 0.7019(3) 0.0195(5) Uani 1 1 d . . . . .
H1A H 0.4041 0.8019 0.7200 0.023 Uiso 1 1 calc R U . . .
H1B H 0.4206 0.6789 0.7734 0.023 Uiso 1 1 calc R U . . .
C2 C 0.46779(8) 0.7995(3) 0.7502(3) 0.0242(6) Uani 1 1 d . . . . .
H2A H 0.4668 0.8243 0.8657 0.029 Uiso 1 1 calc R U . . .
H2B H 0.4896 0.7415 0.7395 0.029 Uiso 1 1 calc R U . . .
C3 C 0.47788(9) 0.9036(3) 0.6393(4) 0.0259(6) Uani 1 1 d . . . . .
H3A H 0.5052 0.9327 0.6693 0.031 Uiso 1 1 calc R U . . .
H3B H 0.4579 0.9649 0.6624 0.031 Uiso 1 1 calc R U . . .
C4 C 0.47741(8) 0.8784(2) 0.4510(4) 0.0216(6) Uani 1 1 d . . . . .
C5 C 0.43666(7) 0.8123(2) 0.4059(3) 0.0169(5) Uani 1 1 d . . . . .
H5 H 0.4144 0.8688 0.4255 0.020 Uiso 1 1 calc R U . . .
C6 C 0.43291(8) 0.7804(2) 0.2208(3) 0.0188(5) Uani 1 1 d . . . . .
H6A H 0.4424 0.8453 0.1532 0.023 Uiso 1 1 calc R U . . .
H6B H 0.4506 0.7140 0.1970 0.023 Uiso 1 1 calc R U . . .
C7 C 0.38800(8) 0.7510(2) 0.1753(3) 0.0181(5) Uani 1 1 d . . . . .
H7A H 0.3869 0.7279 0.0590 0.022 Uiso 1 1 calc R U . . .
H7B H 0.3710 0.8202 0.1882 0.022 Uiso 1 1 calc R U . . .
C8 C 0.36996(8) 0.6534(2) 0.2826(3) 0.0165(5) Uani 1 1 d . . . . .
C9 C 0.37890(8) 0.6739(2) 0.4702(3) 0.0160(5) Uani 1 1 d . . . . .
H9 H 0.3624 0.7425 0.5007 0.019 Uiso 1 1 calc R U . . .
C10 C 0.42523(7) 0.7056(2) 0.5181(3) 0.0172(5) Uani 1 1 d . . . . .
C12 C 0.35842(7) 0.4570(2) 0.5032(3) 0.0160(5) Uani 1 1 d . . . . .
C13 C 0.36913(7) 0.4367(2) 0.3427(3) 0.0166(5) Uani 1 1 d . . . . .
C14 C 0.38640(7) 0.5332(2) 0.2355(3) 0.0157(5) Uani 1 1 d . . . . .
H14 H 0.4168 0.5332 0.2443 0.019 Uiso 1 1 calc R U . . .
C15 C 0.35978(8) 0.3412(2) 0.2318(3) 0.0175(5) Uani 1 1 d . . . . .
C16 C 0.36050(8) 0.3911(2) 0.0607(3) 0.0189(5) Uani 1 1 d . . . . .
C17 C 0.34875(8) 0.2276(2) 0.2495(3) 0.0189(5) Uani 1 1 d . . . . .
H17 H 0.3391 0.1924 0.1525 0.023 Uiso 1 1 calc R U . . .
C18 C 0.51721(8) 0.8145(3) 0.3965(4) 0.0249(6) Uani 1 1 d . . . . .
H18A H 0.5410 0.8623 0.4203 0.037 Uiso 1 1 calc R U . . .
H18B H 0.5160 0.7990 0.2789 0.037 Uiso 1 1 calc R U . . .
H18C H 0.5195 0.7423 0.4563 0.037 Uiso 1 1 calc R U . . .
C19 C 0.47699(9) 0.9974(3) 0.3624(4) 0.0272(6) Uani 1 1 d . . . . .
H19A H 0.4512 1.0363 0.3850 0.041 Uiso 1 1 calc R U . . .
H19B H 0.4799 0.9860 0.2443 0.041 Uiso 1 1 calc R U . . .
H19C H 0.4997 1.0440 0.4026 0.041 Uiso 1 1 calc R U . . .
C20 C 0.45488(8) 0.6006(2) 0.5018(3) 0.0191(5) Uani 1 1 d . . . . .
H20A H 0.4631 0.5916 0.3874 0.029 Uiso 1 1 calc R U . . .
H20B H 0.4409 0.5313 0.5387 0.029 Uiso 1 1 calc R U . . .
H20C H 0.4791 0.6134 0.5694 0.029 Uiso 1 1 calc R U . . .
C21 C 0.34954(8) 0.1531(2) 0.3934(3) 0.0179(5) Uani 1 1 d . . . . .
C22 C 0.37787(8) 0.1655(2) 0.5264(3) 0.0180(5) Uani 1 1 d . . . . .
C23 C 0.37529(8) 0.0965(2) 0.6735(3) 0.0186(5) Uani 1 1 d . . . . .
C24 C 0.34352(8) 0.0096(2) 0.6782(3) 0.0200(5) Uani 1 1 d . . . . .
C25 C 0.31830(8) -0.0112(2) 0.5420(4) 0.0202(5) Uani 1 1 d . . . . .
H25 H 0.2990 -0.0715 0.5448 0.024 Uiso 1 1 calc R U . . .
C26 C 0.32187(8) 0.0582(2) 0.4007(3) 0.0188(5) Uani 1 1 d . . . . .
C27 C 0.40517(9) 0.1171(2) 0.8075(3) 0.0229(6) Uani 1 1 d . . . . .
C28 C 0.40542(10) 0.0506(3) 0.9679(4) 0.0305(6) Uani 1 1 d . . . . .
H28A H 0.4263 0.0822 1.0407 0.046 Uiso 1 1 calc R U . . .
H28B H 0.4115 -0.0298 0.9458 0.046 Uiso 1 1 calc R U . . .
H28C H 0.3786 0.0567 1.0202 0.046 Uiso 1 1 calc R U . . .
C29 C 0.30747(9) -0.1357(3) 0.8365(4) 0.0276(6) Uani 1 1 d . . . . .
H29A H 0.2810 -0.1004 0.8130 0.041 Uiso 1 1 calc R U . . .
H29B H 0.3073 -0.1668 0.9476 0.041 Uiso 1 1 calc R U . . .
H29C H 0.3125 -0.1974 0.7582 0.041 Uiso 1 1 calc R U . . .
O1M O 0.26892(6) 0.82782(17) 0.2764(3) 0.0321(5) Uani 1 1 d . . . . .
H1M H 0.2876 0.7806 0.2919 0.048 Uiso 1 1 calc R U . . .
O2M O 0.29180(6) 0.5740(2) 0.9787(3) 0.0325(5) Uani 1 1 d . . . . .
H2M H 0.3089 0.5671 0.9034 0.049 Uiso 1 1 calc R U . . .
C1M C 0.23138(10) 0.7844(3) 0.3453(5) 0.0375(8) Uani 1 1 d . . . . .
H1M1 H 0.2368 0.7127 0.4029 0.056 Uiso 1 1 calc R U . . .
H1M2 H 0.2117 0.7707 0.2574 0.056 Uiso 1 1 calc R U . . .
H1M3 H 0.2202 0.8403 0.4221 0.056 Uiso 1 1 calc R U . . .
C2M C 0.25183(10) 0.5918(4) 0.9093(5) 0.0473(9) Uani 1 1 d . . . . .
H2M1 H 0.2330 0.6168 0.9951 0.071 Uiso 1 1 calc R U . . .
H2M2 H 0.2420 0.5203 0.8616 0.071 Uiso 1 1 calc R U . . .
H2M3 H 0.2534 0.6504 0.8241 0.071 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
C11 O2 1.222(3) . ?
C11 C12 1.472(4) . ?
C11 C9 1.516(3) . ?
O1 C8 1.437(3) . ?
O1 H2 0.8200 . ?
O3 C12 1.349(3) . ?
O3 H4 0.8200 . ?
O4 C16 1.362(3) . ?
O4 C14 1.451(3) . ?
O5 C16 1.207(3) . ?
O6 C22 1.329(3) . ?
O6 H7 0.8200 . ?
O7 C27 1.248(3) . ?
O8 C24 1.350(3) . ?
O8 C29 1.432(3) . ?
O9 C26 1.348(3) . ?
O9 H10 0.8200 . ?
C1 C2 1.529(4) . ?
C1 C10 1.543(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.525(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.537(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C18 1.538(4) . ?
C4 C19 1.540(4) . ?
C4 C5 1.557(3) . ?
C5 C6 1.533(4) . ?
C5 C10 1.564(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.527(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.527(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.526(3) . ?
C8 C9 1.549(3) . ?
C9 C10 1.580(3) . ?
C9 H9 0.9800 . ?
C10 C20 1.543(3) . ?
C12 C13 1.352(4) . ?
C13 C15 1.443(4) . ?
C13 C14 1.508(3) . ?
C14 H14 0.9800 . ?
C15 C17 1.359(4) . ?
C15 C16 1.486(4) . ?
C17 C21 1.437(4) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C26 1.408(4) . ?
C21 C22 1.410(4) . ?
C22 C23 1.423(4) . ?
C23 C24 1.429(4) . ?
C23 C27 1.460(4) . ?
C24 C25 1.381(4) . ?
C25 C26 1.390(4) . ?
C25 H25 0.9300 . ?
C27 C28 1.496(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
O1M C1M 1.418(4) . ?
O1M H1M 0.8200 . ?
O2M C2M 1.415(4) . ?
O2M H2M 0.8200 . ?
C1M H1M1 0.9600 . ?
C1M H1M2 0.9600 . ?
C1M H1M3 0.9600 . ?
C2M H2M1 0.9600 . ?
C2M H2M2 0.9600 . ?
C2M H2M3 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C11 C12 119.2(2) . . ?
O2 C11 C9 120.6(2) . . ?
C12 C11 C9 120.1(2) . . ?
C8 O1 H2 109.5 . . ?
C12 O3 H4 109.5 . . ?
C16 O4 C14 110.08(19) . . ?
C22 O6 H7 109.5 . . ?
C24 O8 C29 118.9(2) . . ?
C26 O9 H10 109.5 . . ?
C2 C1 C10 112.1(2) . . ?
C2 C1 H1A 109.2 . . ?
C10 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C10 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C3 C2 C1 111.0(2) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 115.0(2) . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 C18 111.1(2) . . ?
C3 C4 C19 106.6(2) . . ?
C18 C4 C19 107.4(2) . . ?
C3 C4 C5 109.1(2) . . ?
C18 C4 C5 113.7(2) . . ?
C19 C4 C5 108.6(2) . . ?
C6 C5 C4 114.0(2) . . ?
C6 C5 C10 110.5(2) . . ?
C4 C5 C10 116.5(2) . . ?
C6 C5 H5 104.8 . . ?
C4 C5 H5 104.8 . . ?
C10 C5 H5 104.8 . . ?
C7 C6 C5 111.0(2) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 112.7(2) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 C14 108.5(2) . . ?
O1 C8 C7 110.1(2) . . ?
C14 C8 C7 113.1(2) . . ?
O1 C8 C9 105.10(19) . . ?
C14 C8 C9 108.3(2) . . ?
C7 C8 C9 111.4(2) . . ?
C11 C9 C8 110.5(2) . . ?
C11 C9 C10 113.0(2) . . ?
C8 C9 C10 116.5(2) . . ?
C11 C9 H9 105.3 . . ?
C8 C9 H9 105.3 . . ?
C10 C9 H9 105.3 . . ?
C20 C10 C1 107.6(2) . . ?
C20 C10 C5 114.8(2) . . ?
C1 C10 C5 108.2(2) . . ?
C20 C10 C9 112.4(2) . . ?
C1 C10 C9 108.4(2) . . ?
C5 C10 C9 105.2(2) . . ?
O3 C12 C13 121.9(2) . . ?
O3 C12 C11 116.8(2) . . ?
C13 C12 C11 120.6(2) . . ?
C12 C13 C15 131.6(2) . . ?
C12 C13 C14 120.6(2) . . ?
C15 C13 C14 106.5(2) . . ?
O4 C14 C13 105.11(19) . . ?
O4 C14 C8 111.06(19) . . ?
C13 C14 C8 113.3(2) . . ?
O4 C14 H14 109.1 . . ?
C13 C14 H14 109.1 . . ?
C8 C14 H14 109.1 . . ?
C17 C15 C13 136.0(2) . . ?
C17 C15 C16 118.0(2) . . ?
C13 C15 C16 105.8(2) . . ?
O5 C16 O4 121.2(2) . . ?
O5 C16 C15 129.0(2) . . ?
O4 C16 C15 109.8(2) . . ?
C15 C17 C21 130.6(2) . . ?
C15 C17 H17 114.7 . . ?
C21 C17 H17 114.7 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 117.1(2) . . ?
C26 C21 C17 118.9(2) . . ?
C22 C21 C17 124.0(2) . . ?
O6 C22 C21 117.1(2) . . ?
O6 C22 C23 120.6(2) . . ?
C21 C22 C23 122.2(2) . . ?
C22 C23 C24 116.9(2) . . ?
C22 C23 C27 118.8(2) . . ?
C24 C23 C27 124.3(2) . . ?
O8 C24 C25 122.4(2) . . ?
O8 C24 C23 116.3(2) . . ?
C25 C24 C23 121.3(2) . . ?
C24 C25 C26 119.8(2) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
O9 C26 C25 120.8(2) . . ?
O9 C26 C21 117.2(2) . . ?
C25 C26 C21 122.0(2) . . ?
O7 C27 C23 119.2(2) . . ?
O7 C27 C28 117.1(2) . . ?
C23 C27 C28 123.6(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O8 C29 H29A 109.5 . . ?
O8 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O8 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C1M O1M H1M 109.5 . . ?
C2M O2M H2M 109.5 . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
O2M C2M H2M1 109.5 . . ?
O2M C2M H2M2 109.5 . . ?
H2M1 C2M H2M2 109.5 . . ?
O2M C2M H2M3 109.5 . . ?
H2M1 C2M H2M3 109.5 . . ?
H2M2 C2M H2M3 109.5 . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.047



