# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_SH3_023
_database_code_depnum_ccdc_archive 'CCDC 1578065'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                            CHEMICAL INFORMATION                            #
#----------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H20 O5'
_chemical_formula_sum            'C20 H20 O5'
_chemical_formula_weight         340.36
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                           UNIT CELL INFORMATION                            #
#----------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_space_group_IT_number           5
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.823(2)
_cell_length_b                   6.9975(7)
_cell_length_c                   27.834(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.799(5)
_cell_angle_gamma                90
_cell_volume                     3409.9(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150
_cell_measurement_reflns_used    5719
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.17
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                            CRYSTAL INFORMATION                             #
#----------------------------------------------------------------------------#

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1440
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                           ABSORPTION CORRECTION                            #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.995

#----------------------------------------------------------------------------#
#                              DATA COLLECTION                               #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0510
_diffrn_reflns_av_uneti/neti     0.0659
_diffrn_reflns_number            18156
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.980
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             7721
_reflns_number_gt                5875
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.977

_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.
;

#----------------------------------------------------------------------------#
#                           COMPUTER PROGRAMS USED                           #
#----------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2016)'

#----------------------------------------------------------------------------#
#                           REFINEMENT INFORMATION                           #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7721
_refine_ls_number_parameters     455
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047

#...............................................................................
# .RES SHELXL file: job.res
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#              ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS              #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.34256(11) 0.7193(3) 0.05670(7) 0.0251(5) Uani 1 1 d . . . . .
C11 C 0.33674(17) 0.8698(4) 0.02067(10) 0.0210(6) Uani 1 1 d . . . . .
H11 H 0.292559 0.954097 0.023676 0.025 Uiso 1 1 calc R U . . .
C12 C 0.41133(17) 0.9847(4) 0.03446(11) 0.0221(6) Uani 1 1 d . . . . .
H12 H 0.449796 0.927397 0.016770 0.027 Uiso 1 1 calc R U . . .
C13 C 0.4027(2) 1.1943(4) 0.02043(12) 0.0302(7) Uani 1 1 d . . . . .
H13A H 0.365634 1.254268 0.037655 0.045 Uiso 1 1 calc R U . . .
H13B H 0.384602 1.205324 -0.014951 0.045 Uiso 1 1 calc R U . . .
H13C H 0.452153 1.258496 0.029510 0.045 Uiso 1 1 calc R U . . .
C14 C 0.32440(16) 0.7867(4) -0.03027(10) 0.0193(6) Uani 1 1 d . . . . .
C15 C 0.27404(17) 0.8713(4) -0.06854(12) 0.0277(7) Uani 1 1 d . . . . .
H15 H 0.246618 0.982023 -0.062246 0.033 Uiso 1 1 calc R U . . .
C16 C 0.26260(19) 0.7971(5) -0.11638(12) 0.0326(8) Uani 1 1 d . . . . .
H16 H 0.228058 0.855130 -0.142427 0.039 Uiso 1 1 calc R U . . .
C17 C 0.30317(18) 0.6388(5) -0.12359(11) 0.0268(7) Uani 1 1 d . . . . .
C18 C 0.35403(17) 0.5552(4) -0.08572(11) 0.0221(7) Uani 1 1 d . . . . .
C19 C 0.36643(16) 0.6252(4) -0.03919(11) 0.0208(6) Uani 1 1 d . . . . .
H19 H 0.402136 0.566896 -0.013789 0.025 Uiso 1 1 calc R U . . .
O20 O 0.30420(14) 0.5400(3) -0.16674(8) 0.0397(6) Uani 1 1 d . . . . .
O21 O 0.38947(13) 0.4023(3) -0.10338(8) 0.0349(6) Uani 1 1 d . . . . .
C22 C 0.3460(2) 0.3703(5) -0.15143(13) 0.0418(9) Uani 1 1 d . . . . .
H22A H 0.380581 0.339310 -0.174351 0.050 Uiso 1 1 calc R U . . .
H22B H 0.310549 0.261705 -0.150992 0.050 Uiso 1 1 calc R U . . .
C31 C 0.52083(18) 0.9827(5) 0.10876(12) 0.0319(8) Uani 1 1 d . . . . .
H31A H 0.552418 0.900410 0.092144 0.048 Uiso 1 1 calc R U . . .
H31B H 0.532086 0.956423 0.143961 0.048 Uiso 1 1 calc R U . . .
H31C H 0.532081 1.116995 0.103020 0.048 Uiso 1 1 calc R U . . .
C32 C 0.43687(17) 0.9430(4) 0.08884(10) 0.0216(6) Uani 1 1 d . . . . .
H32 H 0.404910 1.019047 0.107824 0.026 Uiso 1 1 calc R U . . .
C33 C 0.41501(17) 0.7320(4) 0.09012(10) 0.0214(6) Uani 1 1 d . . . . .
H33 H 0.453358 0.655597 0.076272 0.026 Uiso 1 1 calc R U . . .
C34 C 0.40768(16) 0.6458(4) 0.13861(10) 0.0196(6) Uani 1 1 d . . . . .
C35 C 0.44497(17) 0.4761(4) 0.15344(11) 0.0252(7) Uani 1 1 d . . . . .
H35 H 0.475724 0.418784 0.132978 0.030 Uiso 1 1 calc R U . . .
C36 C 0.43901(18) 0.3861(5) 0.19738(11) 0.0278(7) Uani 1 1 d . . . . .
H36 H 0.465723 0.271220 0.207542 0.033 Uiso 1 1 calc R U . . .
C37 C 0.39287(17) 0.4718(4) 0.22491(10) 0.0241(7) Uani 1 1 d . . . . .
C38 C 0.35570(17) 0.6422(4) 0.21072(11) 0.0241(7) Uani 1 1 d . . . . .
C39 C 0.36206(17) 0.7333(4) 0.16837(11) 0.0250(7) Uani 1 1 d . . . . .
H39 H 0.336713 0.850925 0.159365 0.030 Uiso 1 1 calc R U . . .
O40 O 0.31457(14) 0.6966(3) 0.24574(8) 0.0380(6) Uani 1 1 d . . . . .
O41 O 0.37655(13) 0.4121(3) 0.26902(7) 0.0320(5) Uani 1 1 d . . . . .
C42 C 0.3132(2) 0.5285(5) 0.27522(13) 0.0357(8) Uani 1 1 d . . . . .
H42A H 0.317349 0.564212 0.310037 0.043 Uiso 1 1 calc R U . . .
H42B H 0.264710 0.458005 0.264678 0.043 Uiso 1 1 calc R U . . .
O51 O 0.35638(12) 0.3593(3) 0.56479(7) 0.0296(5) Uani 1 1 d . . . . .
C61 C 0.34919(17) 0.5172(4) 0.53068(11) 0.0234(7) Uani 1 1 d . . . . .
H61 H 0.306471 0.601178 0.536664 0.028 Uiso 1 1 calc R U . . .
C62 C 0.42407(17) 0.6289(4) 0.54396(11) 0.0214(6) Uani 1 1 d . . . . .
H62 H 0.462151 0.569813 0.526255 0.026 Uiso 1 1 calc R U . . .
C63 C 0.4165(2) 0.8395(4) 0.53012(12) 0.0301(7) Uani 1 1 d . . . . .
H63A H 0.379327 0.900202 0.547077 0.045 Uiso 1 1 calc R U . . .
H63B H 0.399179 0.851397 0.494694 0.045 Uiso 1 1 calc R U . . .
H63C H 0.466222 0.902330 0.539663 0.045 Uiso 1 1 calc R U . . .
C64 C 0.32973(16) 0.4425(4) 0.47891(11) 0.0204(6) Uani 1 1 d . . . . .
C65 C 0.27252(17) 0.5261(4) 0.44508(11) 0.0245(7) Uani 1 1 d . . . . .
H65 H 0.246693 0.634593 0.454533 0.029 Uiso 1 1 calc R U . . .
C66 C 0.25123(17) 0.4558(5) 0.39703(11) 0.0261(7) Uani 1 1 d . . . . .
H66 H 0.212007 0.514238 0.373880 0.031 Uiso 1 1 calc R U . . .
C67 C 0.28980(16) 0.2997(4) 0.38551(11) 0.0208(6) Uani 1 1 d . . . . .
C68 C 0.34843(17) 0.2169(4) 0.41886(11) 0.0217(6) Uani 1 1 d . . . . .
C69 C 0.36969(17) 0.2832(4) 0.46555(11) 0.0219(6) Uani 1 1 d . . . . .
H69 H 0.409694 0.224491 0.488069 0.026 Uiso 1 1 calc R U . . .
O70 O 0.28035(12) 0.2023(3) 0.34140(8) 0.0297(5) Uani 1 1 d . . . . .
C72 C 0.3320(2) 0.0456(6) 0.35015(14) 0.0463(10) Uani 1 1 d . . . . .
H72A H 0.303088 -0.075670 0.349127 0.056 Uiso 1 1 calc R U . . .
H72B H 0.363595 0.040818 0.324486 0.056 Uiso 1 1 calc R U . . .
O71 O 0.37961(13) 0.0680(3) 0.39680(8) 0.0330(6) Uani 1 1 d . . . . .
C81 C 0.53220(17) 0.6257(5) 0.61994(12) 0.0285(7) Uani 1 1 d . . . . .
H81A H 0.564726 0.547767 0.602918 0.043 Uiso 1 1 calc R U . . .
H81B H 0.542564 0.593683 0.654832 0.043 Uiso 1 1 calc R U . . .
H81C H 0.543112 0.761304 0.615785 0.043 Uiso 1 1 calc R U . . .
C82 C 0.44893(16) 0.5858(4) 0.59869(11) 0.0198(6) Uani 1 1 d . . . . .
H82 H 0.415996 0.659732 0.617456 0.024 Uiso 1 1 calc R U . . .
C83 C 0.42779(17) 0.3745(4) 0.59902(11) 0.0222(6) Uani 1 1 d . . . . .
H83 H 0.467249 0.299871 0.585782 0.027 Uiso 1 1 calc R U . . .
C84 C 0.41751(16) 0.2838(4) 0.64649(11) 0.0203(6) Uani 1 1 d . . . . .
C85 C 0.36896(17) 0.3638(4) 0.67470(11) 0.0234(6) Uani 1 1 d . . . . .
H85 H 0.345103 0.482621 0.665005 0.028 Uiso 1 1 calc R U . . .
C86 C 0.35424(18) 0.2749(4) 0.71674(11) 0.0270(7) Uani 1 1 d . . . . .
H86 H 0.321780 0.331191 0.736239 0.032 Uiso 1 1 calc R U . . .
C87 C 0.38896(18) 0.1021(4) 0.72852(11) 0.0247(7) Uani 1 1 d . . . . .
C88 C 0.43763(18) 0.0220(4) 0.70117(11) 0.0278(7) Uani 1 1 d . . . . .
C89 C 0.45309(17) 0.1091(4) 0.66021(11) 0.0248(7) Uani 1 1 d . . . . .
H89 H 0.486929 0.052780 0.641662 0.030 Uiso 1 1 calc R U . . .
O90 O 0.46581(16) -0.1483(3) 0.72200(9) 0.0462(7) Uani 1 1 d . . . . .
C92 C 0.4191(3) -0.1906(5) 0.75707(14) 0.0509(11) Uani 1 1 d . . . . .
H92A H 0.450527 -0.245690 0.786973 0.061 Uiso 1 1 calc R U . . .
H92B H 0.379110 -0.284145 0.743449 0.061 Uiso 1 1 calc R U . . .
O91 O 0.38475(15) -0.0141(3) 0.76847(8) 0.0382(6) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                             MOLECULAR GEOMETRY                             #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.444(3) . ?
O1 C33 1.446(3) . ?
C11 C14 1.510(4) . ?
C11 C12 1.540(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.518(4) . ?
C12 C32 1.525(4) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.390(4) . ?
C14 C19 1.404(4) . ?
C15 C16 1.408(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.358(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(4) . ?
C17 O20 1.389(4) . ?
C18 C19 1.364(4) . ?
C18 O21 1.379(3) . ?
C19 H19 0.9500 . ?
O20 C22 1.424(4) . ?
O21 C22 1.432(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C31 C32 1.521(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.529(4) . ?
C32 H32 1.0000 . ?
C33 C34 1.506(4) . ?
C33 H33 1.0000 . ?
C34 C35 1.386(4) . ?
C34 C39 1.405(4) . ?
C35 C36 1.397(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.363(4) . ?
C36 H36 0.9500 . ?
C37 O41 1.378(3) . ?
C37 C38 1.385(4) . ?
C38 C39 1.363(4) . ?
C38 O40 1.379(4) . ?
C39 H39 0.9500 . ?
O40 C42 1.437(4) . ?
O41 C42 1.429(4) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
O51 C83 1.444(4) . ?
O51 C61 1.447(3) . ?
C61 C64 1.511(4) . ?
C61 C62 1.531(4) . ?
C61 H61 1.0000 . ?
C62 C63 1.522(4) . ?
C62 C82 1.535(4) . ?
C62 H62 1.0000 . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?
C64 C65 1.382(4) . ?
C64 C69 1.410(4) . ?
C65 C66 1.409(4) . ?
C65 H65 0.9500 . ?
C66 C67 1.360(4) . ?
C66 H66 0.9500 . ?
C67 O70 1.387(4) . ?
C67 C68 1.388(4) . ?
C68 C69 1.365(4) . ?
C68 O71 1.378(4) . ?
C69 H69 0.9500 . ?
O70 C72 1.423(4) . ?
C72 O71 1.421(4) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C81 C82 1.517(4) . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C82 C83 1.526(4) . ?
C82 H82 1.0000 . ?
C83 C84 1.508(4) . ?
C83 H83 1.0000 . ?
C84 C85 1.390(4) . ?
C84 C89 1.397(4) . ?
C85 C86 1.393(4) . ?
C85 H85 0.9500 . ?
C86 C87 1.370(4) . ?
C86 H86 0.9500 . ?
C87 C88 1.376(5) . ?
C87 O91 1.391(4) . ?
C88 C89 1.366(4) . ?
C88 O90 1.378(4) . ?
C89 H89 0.9500 . ?
O90 C92 1.427(5) . ?
C92 O91 1.440(5) . ?
C92 H92A 0.9900 . ?
C92 H92B 0.9900 . ?

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
C11 O1 C33 110.0(2) . . ?
O1 C11 C14 110.5(2) . . ?
O1 C11 C12 105.2(2) . . ?
C14 C11 C12 113.7(2) . . ?
O1 C11 H11 109.1 . . ?
C14 C11 H11 109.1 . . ?
C12 C11 H11 109.1 . . ?
C13 C12 C32 116.0(3) . . ?
C13 C12 C11 113.5(3) . . ?
C32 C12 C11 103.3(2) . . ?
C13 C12 H12 107.9 . . ?
C32 C12 H12 107.9 . . ?
C11 C12 H12 107.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.8(3) . . ?
C15 C14 C11 121.0(3) . . ?
C19 C14 C11 119.2(3) . . ?
C14 C15 C16 121.8(3) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 117.0(3) . . ?
C17 C16 H16 121.5 . . ?
C15 C16 H16 121.5 . . ?
C16 C17 C18 121.5(3) . . ?
C16 C17 O20 128.9(3) . . ?
C18 C17 O20 109.6(3) . . ?
C19 C18 O21 127.9(3) . . ?
C19 C18 C17 122.5(3) . . ?
O21 C18 C17 109.6(3) . . ?
C18 C19 C14 117.4(3) . . ?
C18 C19 H19 121.3 . . ?
C14 C19 H19 121.3 . . ?
C17 O20 C22 104.3(2) . . ?
C18 O21 C22 104.5(2) . . ?
O20 C22 O21 108.1(2) . . ?
O20 C22 H22A 110.1 . . ?
O21 C22 H22A 110.1 . . ?
O20 C22 H22B 110.1 . . ?
O21 C22 H22B 110.1 . . ?
H22A C22 H22B 108.4 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C31 C32 C12 114.7(2) . . ?
C31 C32 C33 113.9(3) . . ?
C12 C32 C33 100.3(2) . . ?
C31 C32 H32 109.2 . . ?
C12 C32 H32 109.2 . . ?
C33 C32 H32 109.2 . . ?
O1 C33 C34 109.6(2) . . ?
O1 C33 C32 104.2(2) . . ?
C34 C33 C32 118.2(2) . . ?
O1 C33 H33 108.2 . . ?
C34 C33 H33 108.2 . . ?
C32 C33 H33 108.2 . . ?
C35 C34 C39 119.7(3) . . ?
C35 C34 C33 119.5(3) . . ?
C39 C34 C33 120.7(3) . . ?
C34 C35 C36 122.4(3) . . ?
C34 C35 H35 118.8 . . ?
C36 C35 H35 118.8 . . ?
C37 C36 C35 116.5(3) . . ?
C37 C36 H36 121.7 . . ?
C35 C36 H36 121.7 . . ?
C36 C37 O41 128.2(3) . . ?
C36 C37 C38 121.7(3) . . ?
O41 C37 C38 110.2(3) . . ?
C39 C38 O40 128.6(3) . . ?
C39 C38 C37 122.4(3) . . ?
O40 C38 C37 109.0(3) . . ?
C38 C39 C34 117.2(3) . . ?
C38 C39 H39 121.4 . . ?
C34 C39 H39 121.4 . . ?
C38 O40 C42 104.3(2) . . ?
C37 O41 C42 103.8(2) . . ?
O41 C42 O40 107.4(3) . . ?
O41 C42 H42A 110.2 . . ?
O40 C42 H42A 110.2 . . ?
O41 C42 H42B 110.2 . . ?
O40 C42 H42B 110.2 . . ?
H42A C42 H42B 108.5 . . ?
C83 O51 C61 109.6(2) . . ?
O51 C61 C64 109.7(2) . . ?
O51 C61 C62 105.4(2) . . ?
C64 C61 C62 116.2(2) . . ?
O51 C61 H61 108.4 . . ?
C64 C61 H61 108.4 . . ?
C62 C61 H61 108.4 . . ?
C63 C62 C61 113.7(3) . . ?
C63 C62 C82 115.9(2) . . ?
C61 C62 C82 102.5(2) . . ?
C63 C62 H62 108.1 . . ?
C61 C62 H62 108.1 . . ?
C82 C62 H62 108.1 . . ?
C62 C63 H63A 109.5 . . ?
C62 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C62 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C65 C64 C69 120.0(3) . . ?
C65 C64 C61 120.8(3) . . ?
C69 C64 C61 119.2(3) . . ?
C64 C65 C66 122.1(3) . . ?
C64 C65 H65 118.9 . . ?
C66 C65 H65 118.9 . . ?
C67 C66 C65 116.5(3) . . ?
C67 C66 H66 121.8 . . ?
C65 C66 H66 121.8 . . ?
C66 C67 O70 128.3(3) . . ?
C66 C67 C68 121.9(3) . . ?
O70 C67 C68 109.8(3) . . ?
C69 C68 O71 128.2(3) . . ?
C69 C68 C67 122.3(3) . . ?
O71 C68 C67 109.5(3) . . ?
C68 C69 C64 117.1(3) . . ?
C68 C69 H69 121.4 . . ?
C64 C69 H69 121.4 . . ?
C67 O70 C72 105.0(2) . . ?
O71 C72 O70 109.1(3) . . ?
O71 C72 H72A 109.9 . . ?
O70 C72 H72A 109.9 . . ?
O71 C72 H72B 109.9 . . ?
O70 C72 H72B 109.9 . . ?
H72A C72 H72B 108.3 . . ?
C68 O71 C72 105.6(2) . . ?
C82 C81 H81A 109.5 . . ?
C82 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
C82 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
C81 C82 C83 113.6(3) . . ?
C81 C82 C62 115.5(3) . . ?
C83 C82 C62 99.8(2) . . ?
C81 C82 H82 109.2 . . ?
C83 C82 H82 109.2 . . ?
C62 C82 H82 109.2 . . ?
O51 C83 C84 108.1(2) . . ?
O51 C83 C82 104.8(2) . . ?
C84 C83 C82 118.9(3) . . ?
O51 C83 H83 108.2 . . ?
C84 C83 H83 108.2 . . ?
C82 C83 H83 108.2 . . ?
C85 C84 C89 119.8(3) . . ?
C85 C84 C83 121.1(3) . . ?
C89 C84 C83 119.0(3) . . ?
C84 C85 C86 122.0(3) . . ?
C84 C85 H85 119.0 . . ?
C86 C85 H85 119.0 . . ?
C87 C86 C85 116.6(3) . . ?
C87 C86 H86 121.7 . . ?
C85 C86 H86 121.7 . . ?
C86 C87 C88 122.0(3) . . ?
C86 C87 O91 128.2(3) . . ?
C88 C87 O91 109.8(3) . . ?
C89 C88 C87 121.8(3) . . ?
C89 C88 O90 128.5(3) . . ?
C87 C88 O90 109.7(3) . . ?
C88 C89 C84 117.8(3) . . ?
C88 C89 H89 121.1 . . ?
C84 C89 H89 121.1 . . ?
C88 O90 C92 104.7(3) . . ?
O90 C92 O91 107.4(3) . . ?
O90 C92 H92A 110.2 . . ?
O91 C92 H92A 110.2 . . ?
O90 C92 H92B 110.2 . . ?
O91 C92 H92B 110.2 . . ?
H92A C92 H92B 108.5 . . ?
C87 O91 C92 103.7(2) . . ?

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
C33 O1 C11 C14 121.8(2) . . . . ?
C33 O1 C11 C12 -1.3(3) . . . . ?
O1 C11 C12 C13 -150.4(2) . . . . ?
C14 C11 C12 C13 88.6(3) . . . . ?
O1 C11 C12 C32 -23.9(3) . . . . ?
C14 C11 C12 C32 -145.0(2) . . . . ?
O1 C11 C14 C15 139.9(3) . . . . ?
C12 C11 C14 C15 -102.1(3) . . . . ?
O1 C11 C14 C19 -42.2(3) . . . . ?
C12 C11 C14 C19 75.8(3) . . . . ?
C19 C14 C15 C16 1.2(4) . . . . ?
C11 C14 C15 C16 179.2(3) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C15 C16 C17 O20 -178.4(3) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
O20 C17 C18 C19 178.3(3) . . . . ?
C16 C17 C18 O21 -177.6(3) . . . . ?
O20 C17 C18 O21 0.5(4) . . . . ?
O21 C18 C19 C14 178.3(3) . . . . ?
C17 C18 C19 C14 0.9(4) . . . . ?
C15 C14 C19 C18 -1.6(4) . . . . ?
C11 C14 C19 C18 -179.6(3) . . . . ?
C16 C17 O20 C22 -170.4(3) . . . . ?
C18 C17 O20 C22 11.6(4) . . . . ?
C19 C18 O21 C22 170.0(3) . . . . ?
C17 C18 O21 C22 -12.3(3) . . . . ?
C17 O20 C22 O21 -19.2(4) . . . . ?
C18 O21 C22 O20 19.6(4) . . . . ?
C13 C12 C32 C31 -74.4(4) . . . . ?
C11 C12 C32 C31 160.7(3) . . . . ?
C13 C12 C32 C33 163.1(3) . . . . ?
C11 C12 C32 C33 38.3(3) . . . . ?
C11 O1 C33 C34 153.5(2) . . . . ?
C11 O1 C33 C32 26.1(3) . . . . ?
C31 C32 C33 O1 -162.6(2) . . . . ?
C12 C32 C33 O1 -39.6(3) . . . . ?
C31 C32 C33 C34 75.6(3) . . . . ?
C12 C32 C33 C34 -161.4(2) . . . . ?
O1 C33 C34 C35 111.1(3) . . . . ?
C32 C33 C34 C35 -129.9(3) . . . . ?
O1 C33 C34 C39 -67.4(3) . . . . ?
C32 C33 C34 C39 51.6(4) . . . . ?
C39 C34 C35 C36 0.2(4) . . . . ?
C33 C34 C35 C36 -178.4(3) . . . . ?
C34 C35 C36 C37 1.4(5) . . . . ?
C35 C36 C37 O41 179.2(3) . . . . ?
C35 C36 C37 C38 -1.9(5) . . . . ?
C36 C37 C38 C39 0.8(5) . . . . ?
O41 C37 C38 C39 179.9(3) . . . . ?
C36 C37 C38 O40 -178.9(3) . . . . ?
O41 C37 C38 O40 0.2(3) . . . . ?
O40 C38 C39 C34 -179.6(3) . . . . ?
C37 C38 C39 C34 0.8(5) . . . . ?
C35 C34 C39 C38 -1.3(4) . . . . ?
C33 C34 C39 C38 177.2(3) . . . . ?
C39 C38 O40 C42 166.3(3) . . . . ?
C37 C38 O40 C42 -14.1(3) . . . . ?
C36 C37 O41 C42 -167.2(3) . . . . ?
C38 C37 O41 C42 13.8(3) . . . . ?
C37 O41 C42 O40 -22.4(3) . . . . ?
C38 O40 C42 O41 22.7(3) . . . . ?
C83 O51 C61 C64 129.0(2) . . . . ?
C83 O51 C61 C62 3.2(3) . . . . ?
O51 C61 C62 C63 -153.7(3) . . . . ?
C64 C61 C62 C63 84.6(3) . . . . ?
O51 C61 C62 C82 -27.8(3) . . . . ?
C64 C61 C62 C82 -149.6(2) . . . . ?
O51 C61 C64 C65 133.9(3) . . . . ?
C62 C61 C64 C65 -106.7(3) . . . . ?
O51 C61 C64 C69 -44.8(3) . . . . ?
C62 C61 C64 C69 74.6(3) . . . . ?
C69 C64 C65 C66 1.0(4) . . . . ?
C61 C64 C65 C66 -177.8(3) . . . . ?
C64 C65 C66 C67 0.3(4) . . . . ?
C65 C66 C67 O70 179.9(3) . . . . ?
C65 C66 C67 C68 -1.7(4) . . . . ?
C66 C67 C68 C69 1.8(5) . . . . ?
O70 C67 C68 C69 -179.5(3) . . . . ?
C66 C67 C68 O71 -177.0(3) . . . . ?
O70 C67 C68 O71 1.7(3) . . . . ?
O71 C68 C69 C64 178.2(3) . . . . ?
C67 C68 C69 C64 -0.5(4) . . . . ?
C65 C64 C69 C68 -0.9(4) . . . . ?
C61 C64 C69 C68 177.9(3) . . . . ?
C66 C67 O70 C72 -176.9(3) . . . . ?
C68 C67 O70 C72 4.5(3) . . . . ?
C67 O70 C72 O71 -8.9(4) . . . . ?
C69 C68 O71 C72 174.1(3) . . . . ?
C67 C68 O71 C72 -7.1(3) . . . . ?
O70 C72 O71 C68 9.9(4) . . . . ?
C63 C62 C82 C81 -73.3(3) . . . . ?
C61 C62 C82 C81 162.4(3) . . . . ?
C63 C62 C82 C83 164.5(3) . . . . ?
C61 C62 C82 C83 40.2(3) . . . . ?
C61 O51 C83 C84 150.8(2) . . . . ?
C61 O51 C83 C82 23.1(3) . . . . ?
C81 C82 C83 O51 -162.6(2) . . . . ?
C62 C82 C83 O51 -39.1(3) . . . . ?
C81 C82 C83 C84 76.5(3) . . . . ?
C62 C82 C83 C84 -160.0(2) . . . . ?
O51 C83 C84 C85 -66.6(3) . . . . ?
C82 C83 C84 C85 52.6(4) . . . . ?
O51 C83 C84 C89 108.5(3) . . . . ?
C82 C83 C84 C89 -132.3(3) . . . . ?
C89 C84 C85 C86 0.0(5) . . . . ?
C83 C84 C85 C86 175.1(3) . . . . ?
C84 C85 C86 C87 -1.2(5) . . . . ?
C85 C86 C87 C88 1.7(4) . . . . ?
C85 C86 C87 O91 179.1(3) . . . . ?
C86 C87 C88 C89 -1.1(5) . . . . ?
O91 C87 C88 C89 -178.8(3) . . . . ?
C86 C87 C88 O90 178.3(3) . . . . ?
O91 C87 C88 O90 0.6(4) . . . . ?
C87 C88 C89 C84 -0.2(4) . . . . ?
O90 C88 C89 C84 -179.5(3) . . . . ?
C85 C84 C89 C88 0.7(4) . . . . ?
C83 C84 C89 C88 -174.5(3) . . . . ?
C89 C88 O90 C92 -167.9(3) . . . . ?
C87 C88 O90 C92 12.7(4) . . . . ?
C88 O90 C92 O91 -21.0(4) . . . . ?
C86 C87 O91 C92 169.0(3) . . . . ?
C88 C87 O91 C92 -13.4(4) . . . . ?
O90 C92 O91 C87 21.2(4) . . . . ?

#----------------------------------------------------------------------------#
#===END OF CIF FILE FOR SH3_023                                              #
#----------------------------------------------------------------------------#
