# 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_mmcp150909
_audit_block_doi                 10.5517/ccdc.csd.cc1js7q8
_database_code_depnum_ccdc_archive 'CCDC 1423480'
_audit_update_record             
;
2015-09-10 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 O4'
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.4240(4)
_cell_length_b                   8.7348(5)
_cell_length_c                   10.9347(6)
_cell_angle_alpha                87.8550(10)
_cell_angle_beta                 80.4440(10)
_cell_angle_gamma                88.2150(10)
_cell_volume                     698.53(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9147
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      30.99

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7039
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  triumph
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14500
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.890
_diffrn_reflns_theta_max         31.008
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4428
_reflns_number_gt                3866
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0634P)²+0.1789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4428
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
C1 C -0.31081(19) -0.01442(15) 0.33907(11) 0.0423(3) Uani 1 1 d . . . . .
H1A H -0.2184 -0.0948 0.3142 0.063 Uiso 1 1 calc R U . . .
H1B H -0.3732 0.0145 0.2691 0.063 Uiso 1 1 calc R U . . .
H1C H -0.4000 -0.0527 0.4089 0.063 Uiso 1 1 calc R U . . .
C2 C -0.22025(13) 0.12286(11) 0.37745(9) 0.02453(18) Uani 1 1 d . . . . .
C3 C -0.10943(12) 0.21593(10) 0.27386(8) 0.02240(17) Uani 1 1 d . . . . .
H3A H -0.1943 0.2685 0.2242 0.027 Uiso 1 1 calc R U . . .
H3B H -0.0305 0.1448 0.2188 0.027 Uiso 1 1 calc R U . . .
C4 C 0.01090(11) 0.33595(10) 0.31557(8) 0.01834(15) Uani 1 1 d . . . . .
H4 H -0.0647 0.3916 0.3852 0.022 Uiso 1 1 calc R U . . .
C5 C 0.17364(12) 0.25749(10) 0.36656(8) 0.02188(17) Uani 1 1 d . . . . .
H5A H 0.1268 0.1994 0.4442 0.026 Uiso 1 1 calc R U . . .
H5B H 0.2343 0.1833 0.3057 0.026 Uiso 1 1 calc R U . . .
C6 C 0.31607(12) 0.37101(11) 0.39309(8) 0.02204(17) Uani 1 1 d . . . . .
H6A H 0.2684 0.4260 0.4698 0.026 Uiso 1 1 calc R U . . .
H6B H 0.4297 0.3146 0.4055 0.026 Uiso 1 1 calc R U . . .
C7 C 0.35692(11) 0.48578(10) 0.28373(8) 0.01864(16) Uani 1 1 d . . . . .
C8 C 0.50382(12) 0.60517(12) 0.28077(9) 0.02532(18) Uani 1 1 d . . . . .
H8A H 0.5066 0.6437 0.3644 0.030 Uiso 1 1 calc R U . . .
H8B H 0.6264 0.5638 0.2456 0.030 Uiso 1 1 calc R U . . .
C9 C 0.43843(12) 0.72780(11) 0.19646(8) 0.02360(18) Uani 1 1 d . . . . .
H9 H 0.5125 0.8083 0.1575 0.028 Uiso 1 1 calc R U . . .
C10 C 0.26359(11) 0.71054(10) 0.18263(8) 0.01888(16) Uani 1 1 d . . . . .
C11 C 0.18047(11) 0.57751(9) 0.26455(7) 0.01640(15) Uani 1 1 d . . . . .
C12 C 0.07377(11) 0.45597(9) 0.21018(7) 0.01679(15) Uani 1 1 d . . . . .
H12 H -0.0322 0.5028 0.1752 0.020 Uiso 1 1 calc R U . . .
C13 C 0.21999(12) 0.39102(10) 0.10814(8) 0.02000(16) Uani 1 1 d . . . . .
H13A H 0.1927 0.2849 0.0898 0.024 Uiso 1 1 calc R U . . .
H13B H 0.2295 0.4553 0.0310 0.024 Uiso 1 1 calc R U . . .
C14 C 0.39364(12) 0.39526(10) 0.16371(8) 0.02119(17) Uani 1 1 d . . . . .
C15 C 0.15865(13) 0.81327(10) 0.10812(8) 0.02277(17) Uani 1 1 d . . . . .
C16 C 0.25474(14) 0.94755(11) 0.03867(10) 0.0290(2) Uani 1 1 d . . . . .
H16A H 0.1675 1.0100 -0.0011 0.044 Uiso 1 1 calc R U . . .
H16B H 0.3537 0.9102 -0.0248 0.044 Uiso 1 1 calc R U . . .
H16C H 0.3057 1.0099 0.0967 0.044 Uiso 1 1 calc R U . . .
O1 O -0.24141(11) 0.15712(10) 0.48575(7) 0.03463(19) Uani 1 1 d . . . . .
O2 O 0.07121(9) 0.63429(8) 0.37331(6) 0.02215(14) Uani 1 1 d . . . . .
O3 O 0.53967(10) 0.33622(10) 0.12179(7) 0.03445(18) Uani 1 1 d . . . . .
O4 O -0.00063(11) 0.78829(10) 0.10278(9) 0.0397(2) Uani 1 1 d . . . . .
H2 H 0.132(2) 0.696(2) 0.4088(15) 0.050(4) 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
C1 C2 1.4992(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.2159(12) . ?
C2 C3 1.5114(13) . ?
C3 C4 1.5280(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5439(12) . ?
C4 C12 1.5513(11) . ?
C4 H4 1.0000 . ?
C5 C6 1.5408(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5283(12) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5279(12) . ?
C7 C14 1.5386(12) . ?
C7 C11 1.5541(11) . ?
C8 C9 1.5084(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.3452(12) . ?
C9 H9 0.9500 . ?
C10 C15 1.4793(12) . ?
C10 C11 1.5220(11) . ?
C11 O2 1.4202(10) . ?
C11 C12 1.5376(11) . ?
C12 C13 1.5337(11) . ?
C12 H12 1.0000 . ?
C13 C14 1.5157(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O3 1.2122(11) . ?
C15 O4 1.2204(12) . ?
C15 C16 1.5056(13) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O2 H2 0.854(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 120.66(9) . . ?
O1 C2 C3 123.31(8) . . ?
C1 C2 C3 115.99(8) . . ?
C2 C3 C4 115.21(7) . . ?
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 C5 110.34(7) . . ?
C3 C4 C12 111.58(7) . . ?
C5 C4 C12 112.18(7) . . ?
C3 C4 H4 107.5 . . ?
C5 C4 H4 107.5 . . ?
C12 C4 H4 107.5 . . ?
C6 C5 C4 113.37(7) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C5 109.38(7) . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C6 120.72(7) . . ?
C8 C7 C14 109.69(7) . . ?
C6 C7 C14 107.99(7) . . ?
C8 C7 C11 105.68(7) . . ?
C6 C7 C11 110.43(7) . . ?
C14 C7 C11 100.44(6) . . ?
C9 C8 C7 100.92(7) . . ?
C9 C8 H8A 111.6 . . ?
C7 C8 H8A 111.6 . . ?
C9 C8 H8B 111.6 . . ?
C7 C8 H8B 111.6 . . ?
H8A C8 H8B 109.4 . . ?
C10 C9 C8 112.52(8) . . ?
C10 C9 H9 123.7 . . ?
C8 C9 H9 123.7 . . ?
C9 C10 C15 125.70(8) . . ?
C9 C10 C11 110.42(8) . . ?
C15 C10 C11 123.65(7) . . ?
O2 C11 C10 109.79(7) . . ?
O2 C11 C12 109.00(6) . . ?
C10 C11 C12 120.06(7) . . ?
O2 C11 C7 116.11(7) . . ?
C10 C11 C7 100.13(6) . . ?
C12 C11 C7 101.65(6) . . ?
C13 C12 C11 101.75(6) . . ?
C13 C12 C4 112.53(7) . . ?
C11 C12 C4 107.34(6) . . ?
C13 C12 H12 111.6 . . ?
C11 C12 H12 111.6 . . ?
C4 C12 H12 111.6 . . ?
C14 C13 C12 103.31(6) . . ?
C14 C13 H13A 111.1 . . ?
C12 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
O3 C14 C13 125.98(8) . . ?
O3 C14 C7 124.48(8) . . ?
C13 C14 C7 109.54(7) . . ?
O4 C15 C10 120.54(8) . . ?
O4 C15 C16 121.40(9) . . ?
C10 C15 C16 118.05(8) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 O2 H2 110.4(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 13.38(14) . . . . ?
C1 C2 C3 C4 -168.73(10) . . . . ?
C2 C3 C4 C5 71.38(10) . . . . ?
C2 C3 C4 C12 -163.21(8) . . . . ?
C3 C4 C5 C6 171.74(7) . . . . ?
C12 C4 C5 C6 46.66(10) . . . . ?
C4 C5 C6 C7 -45.71(10) . . . . ?
C5 C6 C7 C8 -175.65(8) . . . . ?
C5 C6 C7 C14 -48.42(9) . . . . ?
C5 C6 C7 C11 60.51(9) . . . . ?
C6 C7 C8 C9 -155.33(8) . . . . ?
C14 C7 C8 C9 78.21(9) . . . . ?
C11 C7 C8 C9 -29.27(9) . . . . ?
C7 C8 C9 C10 16.18(10) . . . . ?
C8 C9 C10 C15 178.75(8) . . . . ?
C8 C9 C10 C11 4.05(11) . . . . ?
C9 C10 C11 O2 100.63(8) . . . . ?
C15 C10 C11 O2 -74.19(10) . . . . ?
C9 C10 C11 C12 -131.92(8) . . . . ?
C15 C10 C11 C12 53.26(11) . . . . ?
C9 C10 C11 C7 -22.01(9) . . . . ?
C15 C10 C11 C7 163.16(8) . . . . ?
C8 C7 C11 O2 -86.70(8) . . . . ?
C6 C7 C11 O2 45.43(9) . . . . ?
C14 C7 C11 O2 159.25(7) . . . . ?
C8 C7 C11 C10 31.37(8) . . . . ?
C6 C7 C11 C10 163.50(7) . . . . ?
C14 C7 C11 C10 -82.68(7) . . . . ?
C8 C7 C11 C12 155.18(7) . . . . ?
C6 C7 C11 C12 -72.69(8) . . . . ?
C14 C7 C11 C12 41.13(7) . . . . ?
O2 C11 C12 C13 -171.61(6) . . . . ?
C10 C11 C12 C13 60.58(9) . . . . ?
C7 C11 C12 C13 -48.50(7) . . . . ?
O2 C11 C12 C4 -53.25(8) . . . . ?
C10 C11 C12 C4 178.94(7) . . . . ?
C7 C11 C12 C4 69.86(7) . . . . ?
C3 C4 C12 C13 -73.21(9) . . . . ?
C5 C4 C12 C13 51.18(9) . . . . ?
C3 C4 C12 C11 175.65(7) . . . . ?
C5 C4 C12 C11 -59.96(9) . . . . ?
C11 C12 C13 C14 35.54(8) . . . . ?
C4 C12 C13 C14 -79.04(8) . . . . ?
C12 C13 C14 O3 169.79(9) . . . . ?
C12 C13 C14 C7 -9.74(9) . . . . ?
C8 C7 C14 O3 49.99(12) . . . . ?
C6 C7 C14 O3 -83.38(11) . . . . ?
C11 C7 C14 O3 160.95(9) . . . . ?
C8 C7 C14 C13 -130.47(8) . . . . ?
C6 C7 C14 C13 96.16(8) . . . . ?
C11 C7 C14 C13 -19.51(8) . . . . ?
C9 C10 C15 O4 -179.14(10) . . . . ?
C11 C10 C15 O4 -5.11(14) . . . . ?
C9 C10 C15 C16 1.47(14) . . . . ?
C11 C10 C15 C16 175.50(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.854(18) 2.033(18) 2.8795(10) 171.1(16) 2_566

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mmcp151001
_audit_block_doi                 10.5517/ccdc.csd.cc1k14j8
_database_code_depnum_ccdc_archive 'CCDC 1431069'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 O4'
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4839(7)
_cell_length_b                   13.1593(10)
_cell_length_c                   21.3419(15)
_cell_angle_alpha                90
_cell_angle_beta                 103.329(2)
_cell_angle_gamma                90
_cell_volume                     2865.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7807
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      29.96

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6370
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  triumph
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33195
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.832
_diffrn_reflns_theta_max         30.031
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8280
_reflns_number_gt                5354
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0558P)²+2.3947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8280
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.1600
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_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
C1 C 0.3363(3) 0.0027(2) 0.66817(12) 0.0475(7) Uani 1 1 d . . . . .
H1A H 0.2718 0.0554 0.6709 0.071 Uiso 1 1 calc R U . . .
H1B H 0.4247 0.0287 0.6861 0.071 Uiso 1 1 calc R U . . .
H1C H 0.3206 -0.0571 0.6927 0.071 Uiso 1 1 calc R U . . .
C2 C 0.3239(2) -0.02603(16) 0.59991(10) 0.0251(4) Uani 1 1 d . . . . .
C3 C 0.3580(2) 0.05551(15) 0.55683(9) 0.0231(4) Uani 1 1 d . . . . .
H3A H 0.4546 0.0585 0.5637 0.028 Uiso 1 1 calc R U . . .
H3B H 0.3283 0.1218 0.5703 0.028 Uiso 1 1 calc R U . . .
C4 C 0.29910(19) 0.04152(15) 0.48489(9) 0.0202(4) Uani 1 1 d . . . . .
H4 H 0.3287 -0.0257 0.4716 0.024 Uiso 1 1 calc R U . . .
C5 C 0.1486(2) 0.04156(16) 0.46993(10) 0.0245(4) Uani 1 1 d . . . . .
H5A H 0.1191 0.0987 0.4932 0.029 Uiso 1 1 calc R U . . .
H5B H 0.1186 -0.0222 0.4865 0.029 Uiso 1 1 calc R U . . .
C6 C 0.0833(2) 0.05110(16) 0.39789(10) 0.0261(4) Uani 1 1 d . . . . .
H6A H -0.0109 0.0670 0.3928 0.031 Uiso 1 1 calc R U . . .
H6B H 0.0898 -0.0147 0.3763 0.031 Uiso 1 1 calc R U . . .
C7 C 0.14795(19) 0.13478(15) 0.36529(9) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.0844(2) 0.15878(16) 0.29471(10) 0.0257(4) Uani 1 1 d . . . . .
H8A H 0.1250 0.1187 0.2652 0.031 Uiso 1 1 calc R U . . .
H8B H -0.0110 0.1450 0.2848 0.031 Uiso 1 1 calc R U . . .
C9 C 0.1114(2) 0.26999(16) 0.28993(10) 0.0240(4) Uani 1 1 d . . . . .
H9 H 0.0989 0.3055 0.2502 0.029 Uiso 1 1 calc R U . . .
C10 C 0.15492(19) 0.31389(15) 0.34727(9) 0.0196(4) Uani 1 1 d . . . . .
C11 C 0.16141(19) 0.23843(14) 0.40194(9) 0.0186(4) Uani 1 1 d . . . . .
C12 C 0.29333(19) 0.23246(14) 0.45331(9) 0.0200(4) Uani 1 1 d . . . . .
H12A H 0.3541 0.2863 0.4458 0.024 Uiso 1 1 calc R U . . .
H12B H 0.2783 0.2410 0.4971 0.024 Uiso 1 1 calc R U . . .
C13 C 0.35078(19) 0.12627(14) 0.44589(9) 0.0196(4) Uani 1 1 d . . . . .
H13 H 0.4487 0.1274 0.4550 0.024 Uiso 1 1 calc R U . . .
C14 C 0.2901(2) 0.10152(14) 0.37620(9) 0.0212(4) Uani 1 1 d . . . . .
C15 C 0.1815(2) 0.42346(16) 0.35985(10) 0.0258(4) Uani 1 1 d . . . . .
C16 C 0.1577(2) 0.49570(17) 0.30364(11) 0.0322(5) Uani 1 1 d . . . . .
H16A H 0.1462 0.5647 0.3187 0.048 Uiso 1 1 calc R U . . .
H16B H 0.0785 0.4752 0.2720 0.048 Uiso 1 1 calc R U . . .
H16C H 0.2329 0.4943 0.2836 0.048 Uiso 1 1 calc R U . . .
C17 C -0.0217(3) 1.2532(2) 0.07884(14) 0.0482(7) Uani 1 1 d . . . . .
H17A H -0.0748 1.2250 0.1069 0.072 Uiso 1 1 calc R U . . .
H17B H -0.0668 1.2426 0.0337 0.072 Uiso 1 1 calc R U . . .
H17C H -0.0088 1.3261 0.0872 0.072 Uiso 1 1 calc R U . . .
C18 C 0.1086(3) 1.20105(17) 0.09209(11) 0.0327(5) Uani 1 1 d . . . . .
C19 C 0.1085(2) 1.09241(16) 0.06932(10) 0.0275(5) Uani 1 1 d . . . . .
H19A H 0.0812 1.0921 0.0217 0.033 Uiso 1 1 calc R U . . .
H19B H 0.0413 1.0544 0.0856 0.033 Uiso 1 1 calc R U . . .
C20 C 0.2377(2) 1.03560(15) 0.08928(10) 0.0238(4) Uani 1 1 d . . . . .
H20 H 0.3067 1.0781 0.0766 0.029 Uiso 1 1 calc R U . . .
C21 C 0.2315(2) 0.93390(16) 0.05343(10) 0.0261(4) Uani 1 1 d . . . . .
H21A H 0.1525 0.8963 0.0583 0.031 Uiso 1 1 calc R U . . .
H21B H 0.2220 0.9476 0.0070 0.031 Uiso 1 1 calc R U . . .
C22 C 0.3522(2) 0.86658(17) 0.07731(10) 0.0276(5) Uani 1 1 d . . . . .
H22A H 0.4266 0.8941 0.0613 0.033 Uiso 1 1 calc R U . . .
H22B H 0.3335 0.7973 0.0595 0.033 Uiso 1 1 calc R U . . .
C23 C 0.3913(2) 0.86071(16) 0.15153(10) 0.0225(4) Uani 1 1 d . . . . .
C24 C 0.5053(2) 0.79156(18) 0.18197(12) 0.0320(5) Uani 1 1 d . . . . .
H24A H 0.5075 0.7302 0.1554 0.038 Uiso 1 1 calc R U . . .
H24B H 0.5902 0.8276 0.1881 0.038 Uiso 1 1 calc R U . . .
C25 C 0.4754(2) 0.76497(17) 0.24520(11) 0.0299(5) Uani 1 1 d . . . . .
H25 H 0.5369 0.7345 0.2798 0.036 Uiso 1 1 calc R U . . .
C26 C 0.3527(2) 0.78880(15) 0.24772(10) 0.0222(4) Uani 1 1 d . . . . .
C27 C 0.27709(19) 0.83280(14) 0.18365(9) 0.0191(4) Uani 1 1 d . . . . .
C28 C 0.2017(2) 0.93315(14) 0.18765(9) 0.0202(4) Uani 1 1 d . . . . .
H28A H 0.1118 0.9292 0.1602 0.024 Uiso 1 1 calc R U . . .
H28B H 0.1960 0.9466 0.2326 0.024 Uiso 1 1 calc R U . . .
C29 C 0.2806(2) 1.01756(15) 0.16360(9) 0.0220(4) Uani 1 1 d . . . . .
H29 H 0.2822 1.0820 0.1886 0.026 Uiso 1 1 calc R U . . .
C30 C 0.4141(2) 0.97109(16) 0.17254(9) 0.0236(4) Uani 1 1 d . . . . .
C31 C 0.2918(2) 0.77071(16) 0.30270(10) 0.0268(5) Uani 1 1 d . . . . .
C32 C 0.3769(3) 0.7343(2) 0.36563(11) 0.0376(6) Uani 1 1 d . . . . .
H32A H 0.3287 0.7408 0.3997 0.056 Uiso 1 1 calc R U . . .
H32B H 0.4568 0.7756 0.3766 0.056 Uiso 1 1 calc R U . . .
H32C H 0.4004 0.6629 0.3615 0.056 Uiso 1 1 calc R U . . .
O1 O 0.29158(18) -0.11103(12) 0.58002(8) 0.0373(4) Uani 1 1 d . . . . .
O2 O 0.05915(15) 0.25937(11) 0.43419(7) 0.0229(3) Uani 1 1 d . . . . .
O3 O 0.34214(16) 0.05966(12) 0.33802(7) 0.0321(4) Uani 1 1 d . . . . .
O4 O 0.2204(2) 0.45475(13) 0.41416(8) 0.0487(5) Uani 1 1 d . . . . .
O5 O 0.2091(2) 1.24433(13) 0.11871(9) 0.0474(5) Uani 1 1 d . . . . .
O6 O 0.18768(14) 0.75810(11) 0.14947(7) 0.0233(3) Uani 1 1 d . . . . .
O7 O 0.51948(16) 1.01313(13) 0.18899(8) 0.0363(4) Uani 1 1 d . . . . .
O8 O 0.17484(17) 0.78517(15) 0.29723(8) 0.0412(4) Uani 1 1 d . . . . .
H2 H -0.014(3) 0.263(2) 0.4052(14) 0.043(8) Uiso 1 1 d . . . . .
H6 H 0.225(3) 0.714(2) 0.1320(14) 0.048(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
C1 C2 1.481(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.216(3) . ?
C2 C3 1.509(3) . ?
C3 C4 1.528(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.536(3) . ?
C4 C13 1.561(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.537(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.541(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C14 1.519(3) . ?
C7 C8 1.533(3) . ?
C7 C11 1.562(3) . ?
C8 C9 1.499(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.335(3) . ?
C9 H9 0.9500 . ?
C10 C15 1.481(3) . ?
C10 C11 1.522(3) . ?
C11 O2 1.428(2) . ?
C11 C12 1.556(3) . ?
C12 C13 1.544(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.512(3) . ?
C13 H13 1.0000 . ?
C14 O3 1.213(2) . ?
C15 O4 1.209(3) . ?
C15 C16 1.506(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.496(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O5 1.217(3) . ?
C18 C19 1.510(3) . ?
C19 C20 1.520(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.536(3) . ?
C20 C29 1.564(3) . ?
C20 H20 1.0000 . ?
C21 C22 1.533(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.544(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C30 1.523(3) . ?
C23 C24 1.524(3) . ?
C23 C27 1.554(3) . ?
C24 C25 1.496(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.338(3) . ?
C25 H25 0.9500 . ?
C26 C31 1.478(3) . ?
C26 C27 1.527(3) . ?
C27 O6 1.436(2) . ?
C27 C28 1.551(3) . ?
C28 C29 1.541(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.499(3) . ?
C29 H29 1.0000 . ?
C30 O7 1.212(3) . ?
C31 O8 1.220(3) . ?
C31 C32 1.509(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
O2 H2 0.87(3) . ?
O6 H6 0.83(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 122.1(2) . . ?
O1 C2 C3 121.83(19) . . ?
C1 C2 C3 116.01(19) . . ?
C2 C3 C4 115.41(17) . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 C5 111.49(16) . . ?
C3 C4 C13 109.89(16) . . ?
C5 C4 C13 110.79(16) . . ?
C3 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C13 C4 H4 108.2 . . ?
C4 C5 C6 114.06(16) . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 C7 111.64(16) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C14 C7 C8 113.51(16) . . ?
C14 C7 C6 104.07(16) . . ?
C8 C7 C6 117.00(17) . . ?
C14 C7 C11 101.70(15) . . ?
C8 C7 C11 106.31(15) . . ?
C6 C7 C11 113.34(16) . . ?
C9 C8 C7 102.81(16) . . ?
C9 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C10 C9 C8 112.97(18) . . ?
C10 C9 H9 123.5 . . ?
C8 C9 H9 123.5 . . ?
C9 C10 C15 126.70(18) . . ?
C9 C10 C11 111.47(17) . . ?
C15 C10 C11 121.53(17) . . ?
O2 C11 C10 109.75(15) . . ?
O2 C11 C12 108.32(15) . . ?
C10 C11 C12 116.64(16) . . ?
O2 C11 C7 114.74(16) . . ?
C10 C11 C7 101.70(15) . . ?
C12 C11 C7 105.76(15) . . ?
C13 C12 C11 106.13(15) . . ?
C13 C12 H12A 110.5 . . ?
C11 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C14 C13 C12 102.13(15) . . ?
C14 C13 C4 104.55(15) . . ?
C12 C13 C4 113.59(16) . . ?
C14 C13 H13 112.0 . . ?
C12 C13 H13 112.0 . . ?
C4 C13 H13 112.0 . . ?
O3 C14 C13 127.32(19) . . ?
O3 C14 C7 127.27(19) . . ?
C13 C14 C7 105.32(16) . . ?
O4 C15 C10 120.87(19) . . ?
O4 C15 C16 120.4(2) . . ?
C10 C15 C16 118.71(19) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C18 C17 121.9(2) . . ?
O5 C18 C19 122.0(2) . . ?
C17 C18 C19 116.1(2) . . ?
C18 C19 C20 116.16(19) . . ?
C18 C19 H19A 108.2 . . ?
C20 C19 H19A 108.2 . . ?
C18 C19 H19B 108.2 . . ?
C20 C19 H19B 108.2 . . ?
H19A C19 H19B 107.4 . . ?
C19 C20 C21 110.88(18) . . ?
C19 C20 C29 112.85(17) . . ?
C21 C20 C29 110.02(16) . . ?
C19 C20 H20 107.6 . . ?
C21 C20 H20 107.6 . . ?
C29 C20 H20 107.6 . . ?
C22 C21 C20 113.65(18) . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 C23 111.92(16) . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C30 C23 C24 112.90(18) . . ?
C30 C23 C22 103.94(16) . . ?
C24 C23 C22 117.62(17) . . ?
C30 C23 C27 100.41(15) . . ?
C24 C23 C27 106.21(16) . . ?
C22 C23 C27 114.55(17) . . ?
C25 C24 C23 102.54(17) . . ?
C25 C24 H24A 111.3 . . ?
C23 C24 H24A 111.3 . . ?
C25 C24 H24B 111.3 . . ?
C23 C24 H24B 111.3 . . ?
H24A C24 H24B 109.2 . . ?
C26 C25 C24 112.66(19) . . ?
C26 C25 H25 123.7 . . ?
C24 C25 H25 123.7 . . ?
C25 C26 C31 126.1(2) . . ?
C25 C26 C27 110.99(18) . . ?
C31 C26 C27 122.82(18) . . ?
O6 C27 C26 109.78(15) . . ?
O6 C27 C28 109.24(16) . . ?
C26 C27 C28 116.05(16) . . ?
O6 C27 C23 114.62(16) . . ?
C26 C27 C23 101.02(16) . . ?
C28 C27 C23 106.07(15) . . ?
C29 C28 C27 106.03(15) . . ?
C29 C28 H28A 110.5 . . ?
C27 C28 H28A 110.5 . . ?
C29 C28 H28B 110.5 . . ?
C27 C28 H28B 110.5 . . ?
H28A C28 H28B 108.7 . . ?
C30 C29 C28 102.74(16) . . ?
C30 C29 C20 103.45(16) . . ?
C28 C29 C20 113.34(17) . . ?
C30 C29 H29 112.2 . . ?
C28 C29 H29 112.2 . . ?
C20 C29 H29 112.2 . . ?
O7 C30 C29 127.8(2) . . ?
O7 C30 C23 126.3(2) . . ?
C29 C30 C23 105.81(17) . . ?
O8 C31 C26 120.47(19) . . ?
O8 C31 C32 120.6(2) . . ?
C26 C31 C32 118.9(2) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C11 O2 H2 107.7(18) . . ?
C27 O6 H6 112(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
O1 C2 C3 C4 23.6(3) . . . . ?
C1 C2 C3 C4 -158.3(2) . . . . ?
C2 C3 C4 C5 61.1(2) . . . . ?
C2 C3 C4 C13 -175.69(17) . . . . ?
C3 C4 C5 C6 167.43(17) . . . . ?
C13 C4 C5 C6 44.7(2) . . . . ?
C4 C5 C6 C7 -45.6(2) . . . . ?
C5 C6 C7 C14 59.2(2) . . . . ?
C5 C6 C7 C8 -174.72(17) . . . . ?
C5 C6 C7 C11 -50.5(2) . . . . ?
C14 C7 C8 C9 -90.58(19) . . . . ?
C6 C7 C8 C9 148.13(18) . . . . ?
C11 C7 C8 C9 20.4(2) . . . . ?
C7 C8 C9 C10 -12.2(2) . . . . ?
C8 C9 C10 C15 -175.2(2) . . . . ?
C8 C9 C10 C11 -1.5(2) . . . . ?
C9 C10 C11 O2 -107.68(19) . . . . ?
C15 C10 C11 O2 66.4(2) . . . . ?
C9 C10 C11 C12 128.70(19) . . . . ?
C15 C10 C11 C12 -57.2(2) . . . . ?
C9 C10 C11 C7 14.2(2) . . . . ?
C15 C10 C11 C7 -171.68(18) . . . . ?
C14 C7 C11 O2 -143.62(16) . . . . ?
C8 C7 C11 O2 97.36(19) . . . . ?
C6 C7 C11 O2 -32.5(2) . . . . ?
C14 C7 C11 C10 98.00(16) . . . . ?
C8 C7 C11 C10 -21.02(19) . . . . ?
C6 C7 C11 C10 -150.92(16) . . . . ?
C14 C7 C11 C12 -24.30(18) . . . . ?
C8 C7 C11 C12 -143.32(16) . . . . ?
C6 C7 C11 C12 86.79(19) . . . . ?
O2 C11 C12 C13 122.55(16) . . . . ?
C10 C11 C12 C13 -113.10(18) . . . . ?
C7 C11 C12 C13 -0.93(19) . . . . ?
C11 C12 C13 C14 25.95(19) . . . . ?
C11 C12 C13 C4 -86.03(19) . . . . ?
C3 C4 C13 C14 177.86(16) . . . . ?
C5 C4 C13 C14 -58.5(2) . . . . ?
C3 C4 C13 C12 -71.6(2) . . . . ?
C5 C4 C13 C12 52.0(2) . . . . ?
C12 C13 C14 O3 140.4(2) . . . . ?
C4 C13 C14 O3 -101.0(2) . . . . ?
C12 C13 C14 C7 -42.71(18) . . . . ?
C4 C13 C14 C7 75.89(18) . . . . ?
C8 C7 C14 O3 -27.5(3) . . . . ?
C6 C7 C14 O3 100.8(2) . . . . ?
C11 C7 C14 O3 -141.2(2) . . . . ?
C8 C7 C14 C13 155.65(16) . . . . ?
C6 C7 C14 C13 -76.07(18) . . . . ?
C11 C7 C14 C13 41.90(18) . . . . ?
C9 C10 C15 O4 179.7(2) . . . . ?
C11 C10 C15 O4 6.5(3) . . . . ?
C9 C10 C15 C16 0.4(3) . . . . ?
C11 C10 C15 C16 -172.75(18) . . . . ?
O5 C18 C19 C20 7.9(3) . . . . ?
C17 C18 C19 C20 -173.4(2) . . . . ?
C18 C19 C20 C21 -169.78(17) . . . . ?
C18 C19 C20 C29 66.3(2) . . . . ?
C19 C20 C21 C22 -172.76(17) . . . . ?
C29 C20 C21 C22 -47.2(2) . . . . ?
C20 C21 C22 C23 46.2(2) . . . . ?
C21 C22 C23 C30 -57.7(2) . . . . ?
C21 C22 C23 C24 176.69(19) . . . . ?
C21 C22 C23 C27 50.9(2) . . . . ?
C30 C23 C24 C25 85.2(2) . . . . ?
C22 C23 C24 C25 -153.74(19) . . . . ?
C27 C23 C24 C25 -23.9(2) . . . . ?
C23 C24 C25 C26 13.9(3) . . . . ?
C24 C25 C26 C31 178.8(2) . . . . ?
C24 C25 C26 C27 2.2(3) . . . . ?
C25 C26 C27 O6 104.5(2) . . . . ?
C31 C26 C27 O6 -72.3(2) . . . . ?
C25 C26 C27 C28 -131.10(19) . . . . ?
C31 C26 C27 C28 52.2(3) . . . . ?
C25 C26 C27 C23 -17.0(2) . . . . ?
C31 C26 C27 C23 166.34(18) . . . . ?
C30 C23 C27 O6 149.13(16) . . . . ?
C24 C23 C27 O6 -93.1(2) . . . . ?
C22 C23 C27 O6 38.4(2) . . . . ?
C30 C23 C27 C26 -92.93(17) . . . . ?
C24 C23 C27 C26 24.8(2) . . . . ?
C22 C23 C27 C26 156.39(17) . . . . ?
C30 C23 C27 C28 28.51(19) . . . . ?
C24 C23 C27 C28 146.25(17) . . . . ?
C22 C23 C27 C28 -82.2(2) . . . . ?
O6 C27 C28 C29 -128.96(16) . . . . ?
C26 C27 C28 C29 106.31(19) . . . . ?
C23 C27 C28 C29 -4.9(2) . . . . ?
C27 C28 C29 C30 -21.26(19) . . . . ?
C27 C28 C29 C20 89.68(19) . . . . ?
C19 C20 C29 C30 -174.42(17) . . . . ?
C21 C20 C29 C30 61.2(2) . . . . ?
C19 C20 C29 C28 75.1(2) . . . . ?
C21 C20 C29 C28 -49.3(2) . . . . ?
C28 C29 C30 O7 -143.5(2) . . . . ?
C20 C29 C30 O7 98.3(2) . . . . ?
C28 C29 C30 C23 40.88(19) . . . . ?
C20 C29 C30 C23 -77.27(18) . . . . ?
C24 C23 C30 O7 28.3(3) . . . . ?
C22 C23 C30 O7 -100.3(2) . . . . ?
C27 C23 C30 O7 141.0(2) . . . . ?
C24 C23 C30 C29 -156.03(17) . . . . ?
C22 C23 C30 C29 75.40(19) . . . . ?
C27 C23 C30 C29 -43.34(18) . . . . ?
C25 C26 C31 O8 -171.8(2) . . . . ?
C27 C26 C31 O8 4.4(3) . . . . ?
C25 C26 C31 C32 8.3(3) . . . . ?
C27 C26 C31 C32 -175.50(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O6 0.87(3) 1.92(3) 2.785(2) 171(3) 2_545
O6 H6 O1 0.83(3) 1.98(3) 2.806(2) 172(3) 4_565

_refine_diff_density_max         0.524
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4

