# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1436743'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            CE(OH)2
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H26 O7'
_chemical_formula_sum            'C22 H26 O7'
_chemical_formula_weight         402.43

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                   7.7175(6)
_cell_length_b                   13.5383(11)
_cell_length_c                   18.6624(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.1320(10)
_cell_angle_gamma                90
_cell_volume                     1949.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      25.42

_exptl_crystal_description       CUBE
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20601
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.858
_diffrn_reflns_theta_max         26.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4020
_reflns_number_gt                3843
_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-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0514P)²+1.0184P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4020
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
O3 O 0.80380(11) 0.66743(7) 0.64696(5) 0.0198(2) Uani 1 1 d . . . . .
O2 O 0.38620(11) 0.64874(7) 0.72446(5) 0.0188(2) Uani 1 1 d . . . . .
O4 O 0.30496(13) 0.55472(7) 0.55384(5) 0.0255(2) Uani 1 1 d . . . . .
O6 O 0.77775(12) 0.85410(7) 0.58720(5) 0.0225(2) Uani 1 1 d . . . . .
O5 O 0.22049(12) 0.70900(7) 0.45950(5) 0.0232(2) Uani 1 1 d . . . . .
O1 O 0.50641(13) 0.33828(7) 0.82274(5) 0.0249(2) Uani 1 1 d . . . . .
O7 O 0.50364(13) 0.85721(8) 0.47365(5) 0.0275(2) Uani 1 1 d . . . . .
C14 C 0.37793(15) 0.49167(9) 0.66710(7) 0.0176(3) Uani 1 1 d . . . . .
C22 C 0.95720(16) 0.72250(10) 0.63049(7) 0.0217(3) Uani 1 1 d . . . . .
H22B H 1.0514 0.6782 0.6184 0.026 Uiso 1 1 calc R U . . .
H22A H 0.9921 0.7622 0.6713 0.026 Uiso 1 1 calc R U . . .
C11 C 0.65332(15) 0.55298(9) 0.71801(6) 0.0157(2) Uani 1 1 d . . . . .
C8 C 0.28466(16) 0.48072(9) 0.60313(7) 0.0211(3) Uani 1 1 d . . . . .
C10 C 0.48715(15) 0.58235(9) 0.68029(6) 0.0159(2) Uani 1 1 d . . . . .
H10 H 0.5143 0.6143 0.6346 0.019 Uiso 1 1 calc R U . . .
C13 C 0.37040(15) 0.41745(9) 0.71868(7) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.96288(16) 0.57419(9) 0.73819(7) 0.0208(3) Uani 1 1 d . . . . .
H1 H 1.0669 0.6057 0.7279 0.025 Uiso 1 1 calc R U . . .
C12 C 0.64973(16) 0.47927(9) 0.77024(7) 0.0178(3) Uani 1 1 d . . . . .
C1 C 0.81134(15) 0.59899(9) 0.70134(7) 0.0171(2) Uani 1 1 d . . . . .
C21 C 0.91368(17) 0.78755(10) 0.56775(7) 0.0237(3) Uani 1 1 d . . . . .
H21A H 1.0154 0.8246 0.5535 0.028 Uiso 1 1 calc R U . . .
H21B H 0.8771 0.7473 0.5275 0.028 Uiso 1 1 calc R U . . .
C9 C 0.47750(16) 0.42964(9) 0.78636(7) 0.0192(3) Uani 1 1 d . . . . .
H9 H 0.4130 0.4730 0.8188 0.023 Uiso 1 1 calc R U . . .
C20 C 0.74562(19) 0.93012(11) 0.53568(7) 0.0270(3) Uani 1 1 d . . . . .
H20A H 0.8536 0.9646 0.5267 0.032 Uiso 1 1 calc R U . . .
H20B H 0.6658 0.9773 0.5565 0.032 Uiso 1 1 calc R U . . .
C15 C 0.25294(18) 0.53675(11) 0.48180(7) 0.0259(3) Uani 1 1 d . . . . .
H15B H 0.1280 0.5296 0.4791 0.031 Uiso 1 1 calc R U . . .
H15A H 0.3058 0.4764 0.4643 0.031 Uiso 1 1 calc R U . . .
C3 C 0.95498(16) 0.50141(10) 0.79065(7) 0.0236(3) Uani 1 1 d . . . . .
H2 H 1.0553 0.4844 0.8155 0.028 Uiso 1 1 calc R U . . .
C17 C 0.25215(19) 0.79052(11) 0.41331(8) 0.0287(3) Uani 1 1 d . . . . .
H17A H 0.1846 0.8462 0.4302 0.034 Uiso 1 1 calc R U . . .
H17B H 0.2097 0.7737 0.3659 0.034 Uiso 1 1 calc R U . . .
C4 C 0.80101(17) 0.45345(10) 0.80690(7) 0.0216(3) Uani 1 1 d . . . . .
H3 H 0.7986 0.4046 0.8419 0.026 Uiso 1 1 calc R U . . .
C6 C 0.16996(17) 0.32655(10) 0.64606(9) 0.0296(3) Uani 1 1 d . . . . .
H5 H 0.0975 0.2724 0.6397 0.036 Uiso 1 1 calc R U . . .
C7 C 0.18026(17) 0.39766(10) 0.59270(8) 0.0273(3) Uani 1 1 d . . . . .
H6 H 0.1181 0.3901 0.5503 0.033 Uiso 1 1 calc R U . . .
C16 C 0.31015(18) 0.62268(11) 0.43742(8) 0.0282(3) Uani 1 1 d . . . . .
H16A H 0.4340 0.6324 0.4430 0.034 Uiso 1 1 calc R U . . .
H16B H 0.2863 0.6097 0.3872 0.034 Uiso 1 1 calc R U . . .
C19 C 0.67261(19) 0.89653(12) 0.46487(8) 0.0298(3) Uani 1 1 d . . . . .
H19B H 0.6684 0.9520 0.4320 0.036 Uiso 1 1 calc R U . . .
H19A H 0.7477 0.8465 0.4444 0.036 Uiso 1 1 calc R U . . .
C5 C 0.26540(17) 0.33468(10) 0.70858(8) 0.0249(3) Uani 1 1 d . . . . .
H4 H 0.2597 0.2857 0.7434 0.030 Uiso 1 1 calc R U . . .
C18 C 0.43863(19) 0.82303(12) 0.40666(7) 0.0293(3) Uani 1 1 d . . . . .
H18A H 0.5085 0.7680 0.3902 0.035 Uiso 1 1 calc R U . . .
H18B H 0.4469 0.8755 0.3715 0.035 Uiso 1 1 calc R U . . .
H100 H 0.422(2) 0.7026(15) 0.7142(10) 0.033(5) Uiso 1 1 d . . . . .
H99 H 0.416(3) 0.3304(16) 0.8502(11) 0.047(6) 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
O3 C1 1.3754(15) . ?
O3 C22 1.4330(15) . ?
O2 C10 1.4482(14) . ?
O2 H100 0.80(2) . ?
O4 C8 1.3694(17) . ?
O4 C15 1.4231(16) . ?
O6 C20 1.4296(16) . ?
O6 C21 1.4304(16) . ?
O5 C16 1.4197(16) . ?
O5 C17 1.4219(17) . ?
O1 C9 1.4283(15) . ?
O1 H99 0.87(2) . ?
O7 C19 1.4183(17) . ?
O7 C18 1.4234(17) . ?
C14 C13 1.3929(18) . ?
C14 C8 1.4006(18) . ?
C14 C10 1.5090(16) . ?
C22 C21 1.5024(19) . ?
C22 H22B 0.9700 . ?
C22 H22A 0.9700 . ?
C11 C12 1.3954(18) . ?
C11 C1 1.4049(17) . ?
C11 C10 1.5146(16) . ?
C8 C7 1.3966(18) . ?
C10 H10 0.9800 . ?
C13 C5 1.3955(18) . ?
C13 C9 1.5168(18) . ?
C2 C3 1.3905(19) . ?
C2 C1 1.3963(17) . ?
C2 H1 0.9300 . ?
C12 C4 1.3963(18) . ?
C12 C9 1.5200(17) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C9 H9 0.9800 . ?
C20 C19 1.506(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C15 C16 1.495(2) . ?
C15 H15B 0.9700 . ?
C15 H15A 0.9700 . ?
C3 C4 1.3882(19) . ?
C3 H2 0.9300 . ?
C17 C18 1.510(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C4 H3 0.9300 . ?
C6 C5 1.383(2) . ?
C6 C7 1.388(2) . ?
C6 H5 0.9300 . ?
C7 H6 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19A 0.9700 . ?
C5 H4 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 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
C1 O3 C22 118.37(10) . . ?
C10 O2 H100 104.2(13) . . ?
C8 O4 C15 118.49(10) . . ?
C20 O6 C21 114.14(10) . . ?
C16 O5 C17 112.23(10) . . ?
C9 O1 H99 105.2(14) . . ?
C19 O7 C18 110.05(10) . . ?
C13 C14 C8 119.38(11) . . ?
C13 C14 C10 119.89(11) . . ?
C8 C14 C10 120.73(11) . . ?
O3 C22 C21 106.78(10) . . ?
O3 C22 H22B 110.4 . . ?
C21 C22 H22B 110.4 . . ?
O3 C22 H22A 110.4 . . ?
C21 C22 H22A 110.4 . . ?
H22B C22 H22A 108.6 . . ?
C12 C11 C1 119.37(11) . . ?
C12 C11 C10 119.62(10) . . ?
C1 C11 C10 121.01(11) . . ?
O4 C8 C7 124.21(12) . . ?
O4 C8 C14 115.83(11) . . ?
C7 C8 C14 119.95(13) . . ?
O2 C10 C14 107.26(9) . . ?
O2 C10 C11 110.75(9) . . ?
C14 C10 C11 109.53(10) . . ?
O2 C10 H10 109.8 . . ?
C14 C10 H10 109.8 . . ?
C11 C10 H10 109.8 . . ?
C14 C13 C5 120.73(12) . . ?
C14 C13 C9 118.26(11) . . ?
C5 C13 C9 121.00(12) . . ?
C3 C2 C1 118.63(12) . . ?
C3 C2 H1 120.7 . . ?
C1 C2 H1 120.7 . . ?
C11 C12 C4 120.22(11) . . ?
C11 C12 C9 118.24(11) . . ?
C4 C12 C9 121.54(12) . . ?
O3 C1 C2 124.01(11) . . ?
O3 C1 C11 115.27(10) . . ?
C2 C1 C11 120.72(12) . . ?
O6 C21 C22 109.52(10) . . ?
O6 C21 H21A 109.8 . . ?
C22 C21 H21A 109.8 . . ?
O6 C21 H21B 109.8 . . ?
C22 C21 H21B 109.8 . . ?
H21A C21 H21B 108.2 . . ?
O1 C9 C13 112.70(10) . . ?
O1 C9 C12 109.95(10) . . ?
C13 C9 C12 111.01(10) . . ?
O1 C9 H9 107.7 . . ?
C13 C9 H9 107.7 . . ?
C12 C9 H9 107.7 . . ?
O6 C20 C19 115.90(12) . . ?
O6 C20 H20A 108.3 . . ?
C19 C20 H20A 108.3 . . ?
O6 C20 H20B 108.3 . . ?
C19 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
O4 C15 C16 107.89(11) . . ?
O4 C15 H15B 110.1 . . ?
C16 C15 H15B 110.1 . . ?
O4 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
H15B C15 H15A 108.4 . . ?
C4 C3 C2 121.61(12) . . ?
C4 C3 H2 119.2 . . ?
C2 C3 H2 119.2 . . ?
O5 C17 C18 116.17(12) . . ?
O5 C17 H17A 108.2 . . ?
C18 C17 H17A 108.2 . . ?
O5 C17 H17B 108.2 . . ?
C18 C17 H17B 108.2 . . ?
H17A C17 H17B 107.4 . . ?
C3 C4 C12 119.41(12) . . ?
C3 C4 H3 120.3 . . ?
C12 C4 H3 120.3 . . ?
C5 C6 C7 121.27(12) . . ?
C5 C6 H5 119.4 . . ?
C7 C6 H5 119.4 . . ?
C6 C7 C8 119.51(13) . . ?
C6 C7 H6 120.2 . . ?
C8 C7 H6 120.2 . . ?
O5 C16 C15 109.57(11) . . ?
O5 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
O5 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
O7 C19 C20 110.74(11) . . ?
O7 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
O7 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
H19B C19 H19A 108.1 . . ?
C6 C5 C13 119.08(13) . . ?
C6 C5 H4 120.5 . . ?
C13 C5 H4 120.5 . . ?
O7 C18 C17 110.90(11) . . ?
O7 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
O7 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.0 . . ?

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.071

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1436744'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            CE-ANTHRONE
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 O6'
_chemical_formula_sum            'C22 H24 O6'
_chemical_formula_weight         384.41

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.2726(5)
_cell_length_b                   13.7003(6)
_cell_length_c                   22.4713(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.7520(10)
_cell_angle_gamma                90
_cell_volume                     3752.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9808
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.79

_exptl_crystal_description       CUBE
_exptl_crystal_colour            ORANGE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45084
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.744
_diffrn_reflns_theta_max         28.973
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9382
_reflns_number_gt                7974
_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-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0514P)²+1.4023P] 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         9382
_refine_ls_number_parameters     505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
C23 C 0.32591(8) 0.52885(8) 0.52957(5) 0.0147(2) Uani 1 1 d . . . . .
C24 C 0.29609(9) 0.60074(8) 0.56828(5) 0.0181(2) Uani 1 1 d . . . . .
H24 H 0.2492 0.6509 0.5538 0.022 Uiso 1 1 calc R U . . .
C25 C 0.33707(9) 0.59719(8) 0.62904(5) 0.0205(2) Uani 1 1 d . . . . .
H25 H 0.3168 0.6449 0.6550 0.025 Uiso 1 1 calc R U . . .
C26 C 0.40716(9) 0.52364(8) 0.65056(5) 0.0194(2) Uani 1 1 d . . . . .
H26 H 0.4359 0.5229 0.6907 0.023 Uiso 1 1 calc R U . . .
C27 C 0.60521(9) 0.21445(9) 0.61864(5) 0.0202(2) Uani 1 1 d . . . . .
H27 H 0.6309 0.2123 0.6592 0.024 Uiso 1 1 calc R U . . .
C28 C 0.63373(9) 0.14226(8) 0.58055(5) 0.0220(2) Uani 1 1 d . . . . .
H28 H 0.6782 0.0910 0.5959 0.026 Uiso 1 1 calc R U . . .
C29 C 0.59684(9) 0.14488(8) 0.51920(5) 0.0206(2) Uani 1 1 d . . . . .
H29 H 0.6172 0.0963 0.4938 0.025 Uiso 1 1 calc R U . . .
C30 C 0.52927(8) 0.22117(8) 0.49663(5) 0.0168(2) Uani 1 1 d . . . . .
C31 C 0.50797(9) 0.36917(8) 0.63700(5) 0.0179(2) Uani 1 1 d . . . . .
C32 C 0.42205(8) 0.37390(7) 0.50807(4) 0.0148(2) Uani 1 1 d . . . . .
32B H 0.4554 0.4048 0.4759 0.018 Uiso 1 1 calc R U . . .
32A H 0.3542 0.3438 0.4906 0.018 Uiso 1 1 calc R U . . .
C36 C 0.39503(8) 0.45120(7) 0.55107(5) 0.01394(19) Uani 1 1 d . . . . .
C35 C 0.43534(8) 0.44955(8) 0.61187(5) 0.0157(2) Uani 1 1 d . . . . .
C34 C 0.53692(8) 0.29142(8) 0.59555(5) 0.0162(2) Uani 1 1 d . . . . .
C33 C 0.49755(8) 0.29517(8) 0.53475(5) 0.0148(2) Uani 1 1 d . . . . .
C44 C 0.52362(9) 0.16700(8) 0.39438(5) 0.0215(2) Uani 1 1 d . . . . .
H44A H 0.4974 0.1012 0.4000 0.026 Uiso 1 1 calc R U . . .
H44B H 0.6031 0.1658 0.3979 0.026 Uiso 1 1 calc R U . . .
C43 C 0.47758(9) 0.20553(9) 0.33403(5) 0.0212(2) Uani 1 1 d . . . . .
H43A H 0.4934 0.2747 0.3315 0.025 Uiso 1 1 calc R U . . .
H43B H 0.5112 0.1720 0.3028 0.025 Uiso 1 1 calc R U . . .
C42 C 0.30689(10) 0.24812(8) 0.27908(5) 0.0219(2) Uani 1 1 d . . . . .
H42A H 0.2413 0.2143 0.2617 0.026 Uiso 1 1 calc R U . . .
H42B H 0.3544 0.2566 0.2479 0.026 Uiso 1 1 calc R U . . .
C41 C 0.27532(9) 0.34758(9) 0.30139(5) 0.0209(2) Uani 1 1 d . . . . .
H41A H 0.2433 0.3415 0.3387 0.025 Uiso 1 1 calc R U . . .
H41B H 0.3391 0.3898 0.3080 0.025 Uiso 1 1 calc R U . . .
C40 C 0.17772(10) 0.48768(8) 0.25815(5) 0.0214(2) Uani 1 1 d . . . . .
H40A H 0.1526 0.5111 0.2181 0.026 Uiso 1 1 calc R U . . .
H40B H 0.2462 0.5206 0.2717 0.026 Uiso 1 1 calc R U . . .
C39 C 0.09334(9) 0.51440(9) 0.29960(5) 0.0205(2) Uani 1 1 d . . . . .
H39A H 0.0664 0.5796 0.2896 0.025 Uiso 1 1 calc R U . . .
H39B H 0.0317 0.4699 0.2922 0.025 Uiso 1 1 calc R U . . .
C38 C 0.20185(9) 0.59308(8) 0.37882(5) 0.0177(2) Uani 1 1 d . . . . .
H38A H 0.1682 0.6522 0.3614 0.021 Uiso 1 1 calc R U . . .
H38B H 0.2718 0.5844 0.3634 0.021 Uiso 1 1 calc R U . . .
C37 C 0.22018(8) 0.60297(8) 0.44574(5) 0.0166(2) Uani 1 1 d . . . . .
37B H 0.2531 0.6658 0.4566 0.020 Uiso 1 1 calc R U . . .
H37A H 0.1507 0.5988 0.4622 0.020 Uiso 1 1 calc R U . . .
C8 C 0.99633(8) 0.27897(8) 0.47188(5) 0.0168(2) Uani 1 1 d . . . . .
C7 C 1.05490(9) 0.36548(8) 0.48158(5) 0.0210(2) Uani 1 1 d . . . . .
H6 H 1.0692 0.4043 0.4494 0.025 Uiso 1 1 calc R U . . .
C6 C 1.09211(9) 0.39330(9) 0.54037(6) 0.0234(2) Uani 1 1 d . . . . .
H5 H 1.1307 0.4514 0.5472 0.028 Uiso 1 1 calc R U . . .
C5 C 1.07253(9) 0.33612(9) 0.58838(5) 0.0221(2) Uani 1 1 d . . . . .
H4 H 1.0977 0.3556 0.6272 0.027 Uiso 1 1 calc R U . . .
C4 C 0.91951(10) 0.03341(9) 0.66821(5) 0.0229(2) Uani 1 1 d . . . . .
H3 H 0.9452 0.0528 0.7070 0.027 Uiso 1 1 calc R U . . .
C3 C 0.86424(10) -0.05342(9) 0.65855(5) 0.0246(2) Uani 1 1 d . . . . .
H2 H 0.8527 -0.0925 0.6911 0.030 Uiso 1 1 calc R U . . .
C2 C 0.82507(9) -0.08384(8) 0.60065(5) 0.0223(2) Uani 1 1 d . . . . .
H1 H 0.7871 -0.1424 0.5946 0.027 Uiso 1 1 calc R U . . .
C1 C 0.84353(9) -0.02548(8) 0.55218(5) 0.0173(2) Uani 1 1 d . . . . .
C9 C 0.99403(9) 0.18746(9) 0.63069(5) 0.0193(2) Uani 1 1 d . . . . .
C10 C 0.91378(9) 0.12537(8) 0.50711(5) 0.0157(2) Uani 1 1 d . . . . .
10A H 0.8417 0.1411 0.4869 0.019 Uiso 1 1 calc R U . . .
10B H 0.9516 0.0870 0.4796 0.019 Uiso 1 1 calc R U . . .
C14 C 0.97581(8) 0.21855(8) 0.52026(5) 0.0149(2) Uani 1 1 d . . . . .
C13 C 1.01427(8) 0.24814(8) 0.57832(5) 0.0172(2) Uani 1 1 d . . . . .
C12 C 0.93721(9) 0.09293(8) 0.61922(5) 0.0178(2) Uani 1 1 d . . . . .
C11 C 0.89982(8) 0.06405(8) 0.56083(5) 0.0156(2) Uani 1 1 d . . . . .
C15 C 0.74428(9) -0.13331(8) 0.48156(5) 0.0217(2) Uani 1 1 d . . . . .
H15A H 0.6779 -0.1291 0.5009 0.026 Uiso 1 1 calc R U . . .
H15B H 0.7849 -0.1907 0.4966 0.026 Uiso 1 1 calc R U . . .
C16 C 0.71641(9) -0.13986(8) 0.41506(6) 0.0224(2) Uani 1 1 d . . . . .
H16B H 0.7827 -0.1340 0.3957 0.027 Uiso 1 1 calc R U . . .
H16A H 0.6831 -0.2026 0.4044 0.027 Uiso 1 1 calc R U . . .
C17 C 0.60361(9) -0.07159(9) 0.33333(5) 0.0248(2) Uani 1 1 d . . . . .
H17A H 0.5377 -0.0325 0.3251 0.030 Uiso 1 1 calc R U . . .
H17B H 0.5836 -0.1390 0.3245 0.030 Uiso 1 1 calc R U . . .
C18 C 0.68496(10) -0.03962(9) 0.29185(5) 0.0240(2) Uani 1 1 d . . . . .
H18B H 0.7565 -0.0674 0.3049 0.029 Uiso 1 1 calc R U . . .
H18A H 0.6616 -0.0625 0.2515 0.029 Uiso 1 1 calc R U . . .
C19 C 0.76514(10) 0.09607(9) 0.25207(5) 0.0248(2) Uani 1 1 d . . . . .
H19A H 0.7421 0.0706 0.2123 0.030 Uiso 1 1 calc R U . . .
H19B H 0.8383 0.0717 0.2650 0.030 Uiso 1 1 calc R U . . .
C20 C 0.76717(10) 0.20602(9) 0.24999(5) 0.0254(2) Uani 1 1 d . . . . .
H20A H 0.8058 0.2261 0.2168 0.031 Uiso 1 1 calc R U . . .
H20B H 0.6923 0.2295 0.2420 0.031 Uiso 1 1 calc R U . . .
C21 C 0.93379(9) 0.24271(9) 0.31087(5) 0.0226(2) Uani 1 1 d . . . . .
H21A H 0.9636 0.2684 0.2759 0.027 Uiso 1 1 calc R U . . .
H21B H 0.9544 0.1745 0.3153 0.027 Uiso 1 1 calc R U . . .
C22 C 0.97893(10) 0.29853(9) 0.36552(5) 0.0217(2) Uani 1 1 d . . . . .
H22A H 1.0577 0.3062 0.3664 0.026 Uiso 1 1 calc R U . . .
H22B H 0.9459 0.3629 0.3652 0.026 Uiso 1 1 calc R U . . .
O7 O 0.54337(7) 0.36769(7) 0.69048(4) 0.02756(19) Uani 1 1 d . . . . .
O9 O 0.48683(6) 0.23166(6) 0.43817(3) 0.01927(16) Uani 1 1 d . . . . .
O8 O 0.29162(6) 0.52579(5) 0.46944(3) 0.01683(16) Uani 1 1 d . . . . .
O10 O 0.13274(6) 0.51178(6) 0.36205(3) 0.01817(16) Uani 1 1 d . . . . .
O11 O 0.36180(6) 0.19018(6) 0.32594(4) 0.02141(17) Uani 1 1 d . . . . .
O12 O 0.19757(7) 0.38568(6) 0.25550(4) 0.02691(19) Uani 1 1 d . . . . .
O1 O 1.02347(7) 0.21550(7) 0.68207(4) 0.0297(2) Uani 1 1 d . . . . .
O2 O 0.80961(6) -0.04738(6) 0.49369(4) 0.02013(17) Uani 1 1 d . . . . .
O3 O 0.95412(7) 0.24477(6) 0.41700(3) 0.01938(16) Uani 1 1 d . . . . .
O4 O 0.64235(6) -0.06373(6) 0.39535(4) 0.02270(18) Uani 1 1 d . . . . .
O5 O 0.81758(7) 0.25149(6) 0.30324(4) 0.02238(17) Uani 1 1 d . . . . .
O6 O 0.69176(7) 0.06376(6) 0.29224(4) 0.02362(18) Uani 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
C23 O8 1.3678(12) . ?
C23 C24 1.3912(14) . ?
C23 C36 1.4101(14) . ?
C24 C25 1.3993(16) . ?
C24 H24 0.9300 . ?
C25 C26 1.3753(17) . ?
C25 H25 0.9300 . ?
C26 C35 1.4059(15) . ?
C26 H26 0.9300 . ?
C27 C28 1.3797(17) . ?
C27 C34 1.4076(15) . ?
C27 H27 0.9300 . ?
C28 C29 1.4002(16) . ?
C28 H28 0.9300 . ?
C29 C30 1.3923(15) . ?
C29 H29 0.9300 . ?
C30 O9 1.3626(13) . ?
C30 C33 1.4113(15) . ?
C31 O7 1.2290(13) . ?
C31 C34 1.4852(15) . ?
C31 C35 1.4859(15) . ?
C32 C36 1.4968(14) . ?
C32 C33 1.5002(14) . ?
C32 32B 0.9700 . ?
C32 32A 0.9700 . ?
C36 C35 1.3974(14) . ?
C34 C33 1.3956(14) . ?
C44 O9 1.4358(13) . ?
C44 C43 1.5021(16) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C43 O11 1.4268(13) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C42 O11 1.4234(14) . ?
C42 C41 1.5178(16) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C41 O12 1.4194(14) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C40 O12 1.4210(14) . ?
C40 C39 1.5170(16) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C39 O10 1.4299(13) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C38 O10 1.4236(13) . ?
C38 C37 1.5002(15) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C37 O8 1.4355(12) . ?
C37 37B 0.9700 . ?
C37 H37A 0.9700 . ?
C8 O3 1.3632(13) . ?
C8 C7 1.3900(15) . ?
C8 C14 1.4125(14) . ?
C7 C6 1.3992(17) . ?
C7 H6 0.9300 . ?
C6 C5 1.3770(17) . ?
C6 H5 0.9300 . ?
C5 C13 1.4061(15) . ?
C5 H4 0.9300 . ?
C4 C3 1.3741(18) . ?
C4 C12 1.4072(15) . ?
C4 H3 0.9300 . ?
C3 C2 1.3965(18) . ?
C3 H2 0.9300 . ?
C2 C1 1.3911(15) . ?
C2 H1 0.9300 . ?
C1 O2 1.3647(13) . ?
C1 C11 1.4099(15) . ?
C9 O1 1.2302(14) . ?
C9 C12 1.4791(16) . ?
C9 C13 1.4855(15) . ?
C10 C11 1.4969(14) . ?
C10 C14 1.4979(14) . ?
C10 10A 0.9700 . ?
C10 10B 0.9700 . ?
C14 C13 1.3944(15) . ?
C12 C11 1.3954(15) . ?
C15 O2 1.4324(13) . ?
C15 C16 1.4959(17) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O4 1.4196(14) . ?
C16 H16B 0.9700 . ?
C16 H16A 0.9700 . ?
C17 O4 1.4227(14) . ?
C17 C18 1.5088(17) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O6 1.4187(14) . ?
C18 H18B 0.9700 . ?
C18 H18A 0.9700 . ?
C19 O6 1.4188(15) . ?
C19 C20 1.5074(17) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O5 1.4243(14) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 O5 1.4214(14) . ?
C21 C22 1.4965(17) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O3 1.4340(12) . ?
C22 H22A 0.9700 . ?
C22 H22B 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
O8 C23 C24 124.49(9) . . ?
O8 C23 C36 114.72(9) . . ?
C24 C23 C36 120.78(10) . . ?
C23 C24 C25 119.64(10) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.46(10) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C35 120.04(10) . . ?
C25 C26 H26 120.0 . . ?
C35 C26 H26 120.0 . . ?
C28 C27 C34 119.47(10) . . ?
C28 C27 H27 120.3 . . ?
C34 C27 H27 120.3 . . ?
C27 C28 C29 121.07(10) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C30 C29 C28 119.19(10) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
O9 C30 C29 125.04(10) . . ?
O9 C30 C33 114.08(9) . . ?
C29 C30 C33 120.87(10) . . ?
O7 C31 C34 121.21(10) . . ?
O7 C31 C35 120.74(10) . . ?
C34 C31 C35 118.05(9) . . ?
C36 C32 C33 115.09(9) . . ?
C36 C32 32B 108.5 . . ?
C33 C32 32B 108.5 . . ?
C36 C32 32A 108.5 . . ?
C33 C32 32A 108.5 . . ?
32B C32 32A 107.5 . . ?
C35 C36 C23 118.47(9) . . ?
C35 C36 C32 122.67(9) . . ?
C23 C36 C32 118.86(9) . . ?
C36 C35 C26 120.56(10) . . ?
C36 C35 C31 120.74(9) . . ?
C26 C35 C31 118.70(9) . . ?
C33 C34 C27 120.72(10) . . ?
C33 C34 C31 120.45(9) . . ?
C27 C34 C31 118.83(10) . . ?
C34 C33 C30 118.65(9) . . ?
C34 C33 C32 122.96(9) . . ?
C30 C33 C32 118.39(9) . . ?
O9 C44 C43 106.66(9) . . ?
O9 C44 H44A 110.4 . . ?
C43 C44 H44A 110.4 . . ?
O9 C44 H44B 110.4 . . ?
C43 C44 H44B 110.4 . . ?
H44A C44 H44B 108.6 . . ?
O11 C43 C44 109.06(9) . . ?
O11 C43 H43A 109.9 . . ?
C44 C43 H43A 109.9 . . ?
O11 C43 H43B 109.9 . . ?
C44 C43 H43B 109.9 . . ?
H43A C43 H43B 108.3 . . ?
O11 C42 C41 111.93(9) . . ?
O11 C42 H42A 109.2 . . ?
C41 C42 H42A 109.2 . . ?
O11 C42 H42B 109.2 . . ?
C41 C42 H42B 109.2 . . ?
H42A C42 H42B 107.9 . . ?
O12 C41 C42 105.44(9) . . ?
O12 C41 H41A 110.7 . . ?
C42 C41 H41A 110.7 . . ?
O12 C41 H41B 110.7 . . ?
C42 C41 H41B 110.7 . . ?
H41A C41 H41B 108.8 . . ?
O12 C40 C39 113.32(9) . . ?
O12 C40 H40A 108.9 . . ?
C39 C40 H40A 108.9 . . ?
O12 C40 H40B 108.9 . . ?
C39 C40 H40B 108.9 . . ?
H40A C40 H40B 107.7 . . ?
O10 C39 C40 114.84(9) . . ?
O10 C39 H39A 108.6 . . ?
C40 C39 H39A 108.6 . . ?
O10 C39 H39B 108.6 . . ?
C40 C39 H39B 108.6 . . ?
H39A C39 H39B 107.5 . . ?
O10 C38 C37 110.52(8) . . ?
O10 C38 H38A 109.5 . . ?
C37 C38 H38A 109.5 . . ?
O10 C38 H38B 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 108.1 . . ?
O8 C37 C38 108.57(8) . . ?
O8 C37 37B 110.0 . . ?
C38 C37 37B 110.0 . . ?
O8 C37 H37A 110.0 . . ?
C38 C37 H37A 110.0 . . ?
37B C37 H37A 108.4 . . ?
O3 C8 C7 124.71(10) . . ?
O3 C8 C14 114.31(9) . . ?
C7 C8 C14 120.98(10) . . ?
C8 C7 C6 119.06(10) . . ?
C8 C7 H6 120.5 . . ?
C6 C7 H6 120.5 . . ?
C5 C6 C7 121.14(11) . . ?
C5 C6 H5 119.4 . . ?
C7 C6 H5 119.4 . . ?
C6 C5 C13 119.60(11) . . ?
C6 C5 H4 120.2 . . ?
C13 C5 H4 120.2 . . ?
C3 C4 C12 119.79(11) . . ?
C3 C4 H3 120.1 . . ?
C12 C4 H3 120.1 . . ?
C4 C3 C2 121.00(10) . . ?
C4 C3 H2 119.5 . . ?
C2 C3 H2 119.5 . . ?
C1 C2 C3 119.21(11) . . ?
C1 C2 H1 120.4 . . ?
C3 C2 H1 120.4 . . ?
O2 C1 C2 124.65(10) . . ?
O2 C1 C11 114.40(9) . . ?
C2 C1 C11 120.95(10) . . ?
O1 C9 C12 121.16(10) . . ?
O1 C9 C13 120.71(11) . . ?
C12 C9 C13 118.12(9) . . ?
C11 C10 C14 115.02(9) . . ?
C11 C10 10A 108.5 . . ?
C14 C10 10A 108.5 . . ?
C11 C10 10B 108.5 . . ?
C14 C10 10B 108.5 . . ?
10A C10 10B 107.5 . . ?
C13 C14 C8 118.58(10) . . ?
C13 C14 C10 122.73(9) . . ?
C8 C14 C10 118.69(9) . . ?
C14 C13 C5 120.63(10) . . ?
C14 C13 C9 120.58(10) . . ?
C5 C13 C9 118.79(10) . . ?
C11 C12 C4 120.49(11) . . ?
C11 C12 C9 120.55(10) . . ?
C4 C12 C9 118.95(10) . . ?
C12 C11 C1 118.55(10) . . ?
C12 C11 C10 122.88(10) . . ?
C1 C11 C10 118.54(9) . . ?
O2 C15 C16 107.24(9) . . ?
O2 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
O2 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
O4 C16 C15 109.30(9) . . ?
O4 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
O4 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
H16B C16 H16A 108.3 . . ?
O4 C17 C18 114.46(9) . . ?
O4 C17 H17A 108.6 . . ?
C18 C17 H17A 108.6 . . ?
O4 C17 H17B 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
O6 C18 C17 109.19(9) . . ?
O6 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
O6 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
H18B C18 H18A 108.3 . . ?
O6 C19 C20 110.22(10) . . ?
O6 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
O6 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
O5 C20 C19 114.72(10) . . ?
O5 C20 H20A 108.6 . . ?
C19 C20 H20A 108.6 . . ?
O5 C20 H20B 108.6 . . ?
C19 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
O5 C21 C22 108.97(9) . . ?
O5 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
O5 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
O3 C22 C21 107.83(9) . . ?
O3 C22 H22A 110.1 . . ?
C21 C22 H22A 110.1 . . ?
O3 C22 H22B 110.1 . . ?
C21 C22 H22B 110.1 . . ?
H22A C22 H22B 108.5 . . ?
C30 O9 C44 118.70(8) . . ?
C23 O8 C37 116.58(8) . . ?
C38 O10 C39 111.24(8) . . ?
C42 O11 C43 112.95(9) . . ?
C41 O12 C40 115.79(9) . . ?
C1 O2 C15 117.68(8) . . ?
C8 O3 C22 117.33(9) . . ?
C16 O4 C17 112.22(9) . . ?
C21 O5 C20 113.25(9) . . ?
C18 O6 C19 110.41(9) . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1436745'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'COMPOUND 6'
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H56 N6 O9'
_chemical_formula_sum            'C52 H56 N6 O9'
_chemical_formula_weight         909.02

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'
N N 0.0061 0.0033 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.6503(6)
_cell_length_b                   26.3127(13)
_cell_length_c                   14.6567(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.0910(10)
_cell_angle_gamma                90
_cell_volume                     4467.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.44


_exptl_crystal_description       CUBE
_exptl_crystal_colour            ORANGE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             1928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49057
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.548
_diffrn_reflns_theta_max         26.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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             9256
_reflns_number_gt                6993
_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-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0501P)²+2.8432P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9256
_refine_ls_number_parameters     620
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.028
_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 -0.15503(16) 0.09533(7) 0.50012(12) 0.0235(4) Uani 1 1 d . . . . .
C2 C -0.25418(17) 0.10629(8) 0.54315(13) 0.0287(4) Uani 1 1 d . . . . .
H2 H -0.3161 0.0838 0.5373 0.034 Uiso 1 1 calc R U . . .
C3 C -0.26070(17) 0.15022(8) 0.59411(13) 0.0287(5) Uani 1 1 d . . . . .
H3 H -0.3274 0.1574 0.6213 0.034 Uiso 1 1 calc R U . . .
C4 C -0.16821(17) 0.18348(8) 0.60482(13) 0.0277(4) Uani 1 1 d . . . . .
H4 H -0.1719 0.2126 0.6404 0.033 Uiso 1 1 calc R U . . .
C5 C 0.23546(18) 0.22521(7) 0.57246(14) 0.0278(4) Uani 1 1 d . . . . .
H5 H 0.2281 0.2527 0.6113 0.033 Uiso 1 1 calc R U . . .
C6 C 0.34072(18) 0.21418(8) 0.54337(15) 0.0310(5) Uani 1 1 d . . . . .
H6 H 0.4045 0.2343 0.5621 0.037 Uiso 1 1 calc R U . . .
C7 C 0.35196(17) 0.17327(7) 0.48635(14) 0.0278(4) Uani 1 1 d . . . . .
H7 H 0.4236 0.1660 0.4669 0.033 Uiso 1 1 calc R U . . .
C8 C 0.25701(16) 0.14256(7) 0.45734(13) 0.0230(4) Uani 1 1 d . . . . .
C9 C 0.02922(17) 0.20875(7) 0.57918(13) 0.0247(4) Uani 1 1 d . . . . .
C10 C 0.04439(16) 0.12061(7) 0.45902(12) 0.0222(4) Uani 1 1 d . . . . .
C11 C -0.06141(16) 0.12947(7) 0.50761(12) 0.0226(4) Uani 1 1 d . . . . .
C12 C -0.06960(16) 0.17318(7) 0.56204(12) 0.0235(4) Uani 1 1 d . . . . .
C13 C 0.13978(17) 0.19551(7) 0.54415(13) 0.0235(4) Uani 1 1 d . . . . .
C14 C 0.14783(16) 0.15326(7) 0.48594(12) 0.0217(4) Uani 1 1 d . . . . .
C15 C 0.38242(16) 0.08429(7) 0.39507(14) 0.0260(4) Uani 1 1 d . . . . .
H15A H 0.4223 0.0788 0.4558 0.031 Uiso 1 1 calc R U . . .
H15B H 0.4242 0.1100 0.3646 0.031 Uiso 1 1 calc R U . . .
C16 C 0.38016(17) 0.03578(8) 0.34142(13) 0.0256(4) Uani 1 1 d . . . . .
C17 C 0.27146(17) -0.02562(8) 0.24346(14) 0.0291(5) Uani 1 1 d . . . . .
H17A H 0.3275 -0.0511 0.2662 0.035 Uiso 1 1 calc R U . . .
H17B H 0.2918 -0.0139 0.1845 0.035 Uiso 1 1 calc R U . . .
C18 C 0.15322(18) -0.04961(7) 0.23046(14) 0.0280(4) Uani 1 1 d . . . . .
H18A H 0.1501 -0.0726 0.1786 0.034 Uiso 1 1 calc R U . . .
H18B H 0.1427 -0.0697 0.2844 0.034 Uiso 1 1 calc R U . . .
C19 C -0.05224(18) -0.04147(7) 0.19603(13) 0.0273(4) Uani 1 1 d . . . . .
H19A H -0.0425 -0.0678 0.1511 0.033 Uiso 1 1 calc R U . . .
H19B H -0.1116 -0.0184 0.1697 0.033 Uiso 1 1 calc R U . . .
C20 C -0.0915(2) -0.06565(8) 0.28083(15) 0.0353(5) Uani 1 1 d . . . . .
H20A H -0.1607 -0.0855 0.2641 0.042 Uiso 1 1 calc R U . . .
H20B H -0.0320 -0.0883 0.3083 0.042 Uiso 1 1 calc R U . . .
C21 C -0.20692(17) -0.03026(8) 0.39354(14) 0.0291(5) Uani 1 1 d . . . . .
C22 C -0.23397(18) 0.01417(8) 0.45201(14) 0.0303(5) Uani 1 1 d . . . . .
H22A H -0.3077 0.0288 0.4285 0.036 Uiso 1 1 calc R U . . .
H22B H -0.2395 0.0028 0.5144 0.036 Uiso 1 1 calc R U . . .
C23 C 0.06997(16) 0.02321(7) 0.14182(12) 0.0197(4) Uani 1 1 d . . . . .
H23A H 0.0364 0.0096 0.0835 0.024 Uiso 1 1 calc R U . . .
H23B H 0.1513 0.0294 0.1377 0.024 Uiso 1 1 calc R U . . .
C24 C 0.01013(15) 0.07285(6) 0.16181(12) 0.0175(4) Uani 1 1 d . . . . .
H24A H -0.0711 0.0663 0.1657 0.021 Uiso 1 1 calc R U . . .
H24B H 0.0431 0.0859 0.2207 0.021 Uiso 1 1 calc R U . . .
C25 C -0.05183(14) 0.11381(6) 0.01325(11) 0.0157(4) Uani 1 1 d . . . . .
C26 C -0.01758(14) 0.15965(6) -0.03682(12) 0.0163(4) Uani 1 1 d . . . . .
C27 C -0.06199(15) 0.17969(7) -0.12114(12) 0.0199(4) Uani 1 1 d . . . . .
H27 H -0.1232 0.1640 -0.1562 0.024 Uiso 1 1 calc R U . . .
C28 C -0.01248(16) 0.22369(7) -0.15160(12) 0.0218(4) Uani 1 1 d . . . . .
H28 H -0.0401 0.2375 -0.2081 0.026 Uiso 1 1 calc R U . . .
C29 C 0.07847(16) 0.24732(7) -0.09798(13) 0.0221(4) Uani 1 1 d . . . . .
H29 H 0.1105 0.2769 -0.1191 0.026 Uiso 1 1 calc R U . . .
C30 C 0.12196(15) 0.22731(7) -0.01343(12) 0.0189(4) Uani 1 1 d . . . . .
H30 H 0.1822 0.2432 0.0224 0.023 Uiso 1 1 calc R U . . .
C31 C 0.07310(14) 0.18309(6) 0.01578(11) 0.0152(3) Uani 1 1 d . . . . .
C32 C 0.10384(14) 0.15397(6) 0.10497(11) 0.0147(3) Uani 1 1 d . . . . .
C33 C 0.22911(14) 0.13676(6) 0.11602(11) 0.0150(3) Uani 1 1 d . . . . .
C34 C 0.31050(14) 0.16091(6) 0.17687(11) 0.0153(3) Uani 1 1 d . . . . .
C35 C 0.42711(14) 0.14787(7) 0.18475(12) 0.0167(4) Uani 1 1 d . . . . .
H35 H 0.4791 0.1652 0.2261 0.020 Uiso 1 1 calc R U . . .
C36 C 0.46686(14) 0.10884(7) 0.13102(12) 0.0169(4) Uani 1 1 d . . . . .
C37 C 0.38345(15) 0.08291(7) 0.07130(12) 0.0184(4) Uani 1 1 d . . . . .
H37 H 0.4057 0.0556 0.0370 0.022 Uiso 1 1 calc R U . . .
C38 C 0.26926(15) 0.09776(7) 0.06336(12) 0.0180(4) Uani 1 1 d . . . . .
H38 H 0.2170 0.0811 0.0212 0.022 Uiso 1 1 calc R U . . .
C39 C 0.67026(15) 0.13041(7) 0.18058(13) 0.0213(4) Uani 1 1 d . . . . .
H39A H 0.6405 0.1649 0.1795 0.026 Uiso 1 1 calc R U . . .
H39B H 0.7376 0.1303 0.1470 0.026 Uiso 1 1 calc R U . . .
C40 C 0.70757(18) 0.11578(8) 0.27928(14) 0.0308(5) Uani 1 1 d . . . . .
H40A H 0.7650 0.1393 0.3053 0.046 Uiso 1 1 calc R U . . .
H40B H 0.7393 0.0821 0.2812 0.046 Uiso 1 1 calc R U . . .
H40C H 0.6420 0.1167 0.3138 0.046 Uiso 1 1 calc R U . . .
C41 C 0.62301(16) 0.05094(7) 0.09136(13) 0.0234(4) Uani 1 1 d . . . . .
H41A H 0.7044 0.0546 0.0842 0.028 Uiso 1 1 calc R U . . .
H41B H 0.5820 0.0472 0.0306 0.028 Uiso 1 1 calc R U . . .
C42 C 0.60627(19) 0.00283(8) 0.14615(14) 0.0305(5) Uani 1 1 d . . . . .
H42A H 0.6340 -0.0259 0.1146 0.046 Uiso 1 1 calc R U . . .
H42B H 0.5257 -0.0016 0.1525 0.046 Uiso 1 1 calc R U . . .
H42C H 0.6486 0.0057 0.2058 0.046 Uiso 1 1 calc R U . . .
C43 C 0.07967(14) 0.18574(6) 0.18689(11) 0.0148(3) Uani 1 1 d . . . . .
C44 C 0.16778(14) 0.20928(6) 0.24276(11) 0.0151(3) Uani 1 1 d . . . . .
C45 C 0.14695(15) 0.24334(7) 0.31112(12) 0.0169(4) Uani 1 1 d . . . . .
H45 H 0.2087 0.2590 0.3456 0.020 Uiso 1 1 calc R U . . .
C46 C 0.03324(15) 0.25449(6) 0.32897(11) 0.0162(4) Uani 1 1 d . . . . .
C47 C -0.05667(15) 0.22892(7) 0.27493(12) 0.0198(4) Uani 1 1 d . . . . .
H47 H -0.1329 0.2342 0.2860 0.024 Uiso 1 1 calc R U . . .
C48 C -0.03254(15) 0.19630(7) 0.20624(12) 0.0182(4) Uani 1 1 d . . . . .
H48 H -0.0937 0.1806 0.1711 0.022 Uiso 1 1 calc R U . . .
C49 C 0.09839(16) 0.32366(7) 0.43553(13) 0.0224(4) Uani 1 1 d . . . . .
H49A H 0.1698 0.3053 0.4524 0.027 Uiso 1 1 calc R U . . .
H49B H 0.0741 0.3382 0.4911 0.027 Uiso 1 1 calc R U . . .
C50 C 0.12241(18) 0.36667(8) 0.37088(15) 0.0310(5) Uani 1 1 d . . . . .
H50A H 0.1808 0.3886 0.4006 0.046 Uiso 1 1 calc R U . . .
H50B H 0.0529 0.3858 0.3551 0.046 Uiso 1 1 calc R U . . .
H50C H 0.1487 0.3528 0.3162 0.046 Uiso 1 1 calc R U . . .
C51 C -0.10884(16) 0.29831(7) 0.41483(13) 0.0223(4) Uani 1 1 d . . . . .
H51A H -0.1083 0.3116 0.4766 0.027 Uiso 1 1 calc R U . . .
H51B H -0.1514 0.2666 0.4122 0.027 Uiso 1 1 calc R U . . .
C52 C -0.17351(17) 0.33577(8) 0.34844(14) 0.0275(4) Uani 1 1 d . . . . .
H52A H -0.2504 0.3405 0.3649 0.041 Uiso 1 1 calc R U . . .
H52B H -0.1770 0.3226 0.2871 0.041 Uiso 1 1 calc R U . . .
H52C H -0.1338 0.3678 0.3516 0.041 Uiso 1 1 calc R U . . .
N1 N -0.11535(16) -0.02671(7) 0.34687(12) 0.0305(4) Uani 1 1 d . . . . .
N2 N 0.27783(15) 0.01721(6) 0.30746(11) 0.0255(4) Uani 1 1 d . . . . .
N3 N 0.05667(13) -0.01342(6) 0.21496(10) 0.0212(3) Uani 1 1 d . . . . .
N4 N 0.02171(12) 0.11096(5) 0.09155(9) 0.0145(3) Uani 1 1 d . . . . .
N5 N 0.01060(12) 0.28749(6) 0.39795(10) 0.0199(3) Uani 1 1 d . . . . .
N6 N 0.58293(12) 0.09743(6) 0.13322(10) 0.0199(3) Uani 1 1 d . . . . .
O1 O 0.02068(13) 0.24733(5) 0.62511(10) 0.0337(3) Uani 1 1 d . . . . .
O2 O 0.04515(12) 0.08790(5) 0.39994(9) 0.0313(3) Uani 1 1 d . . . . .
O3 O 0.26748(11) 0.10141(5) 0.40274(9) 0.0251(3) Uani 1 1 d . . . . .
O4 O -0.14577(11) 0.05154(5) 0.45153(9) 0.0274(3) Uani 1 1 d . . . . .
O5 O -0.27094(13) -0.06754(6) 0.38917(11) 0.0408(4) Uani 1 1 d . . . . .
O6 O 0.47314(12) 0.01527(6) 0.33133(11) 0.0396(4) Uani 1 1 d . . . . .
O7 O -0.13102(10) 0.08379(5) -0.00877(9) 0.0214(3) Uani 1 1 d . . . . .
O8 O 0.28342(10) 0.20051(5) 0.23309(8) 0.0185(3) Uani 1 1 d . . . . .
O200 O 0.49537(16) -0.08978(9) 0.37197(16) 0.0630(6) Uani 1 1 d D . . . .
H201 H 0.5767(18) -0.0908(18) 0.370(3) 0.151(18) Uiso 1 1 d D . . . .
H200 H 0.485(4) -0.0524(8) 0.374(3) 0.137(17) Uiso 1 1 d D . . . .
H101 H 0.217(2) 0.0348(9) 0.3198(15) 0.034(6) Uiso 1 1 d . . . . .
H100 H -0.069(2) 0.0016(9) 0.3552(16) 0.038(6) 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 O4 1.365(2) . ?
C1 C2 1.403(3) . ?
C1 C11 1.408(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C12 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(3) . ?
C5 C13 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.399(3) . ?
C7 H7 0.9300 . ?
C8 O3 1.360(2) . ?
C8 C14 1.409(3) . ?
C9 O1 1.228(2) . ?
C9 C13 1.478(3) . ?
C9 C12 1.484(3) . ?
C10 O2 1.222(2) . ?
C10 C14 1.498(3) . ?
C10 C11 1.506(3) . ?
C11 C12 1.409(3) . ?
C13 C14 1.411(3) . ?
C15 O3 1.429(2) . ?
C15 C16 1.498(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O6 1.233(2) . ?
C16 N2 1.335(3) . ?
C17 N2 1.463(2) . ?
C17 C18 1.509(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N3 1.473(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N3 1.469(2) . ?
C19 C20 1.510(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N1 1.456(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 O5 1.230(2) . ?
C21 N1 1.330(3) . ?
C21 C22 1.503(3) . ?
C22 O4 1.423(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 N3 1.462(2) . ?
C23 C24 1.523(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 N4 1.454(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O7 1.231(2) . ?
C25 N4 1.359(2) . ?
C25 C26 1.488(2) . ?
C26 C31 1.385(2) . ?
C26 C27 1.392(2) . ?
C27 C28 1.388(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.396(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.391(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.383(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.525(2) . ?
C32 N4 1.481(2) . ?
C32 C43 1.514(2) . ?
C32 C33 1.520(2) . ?
C33 C34 1.385(2) . ?
C33 C38 1.394(2) . ?
C34 O8 1.386(2) . ?
C34 C35 1.394(2) . ?
C35 C36 1.402(2) . ?
C35 H35 0.9300 . ?
C36 N6 1.382(2) . ?
C36 C37 1.413(2) . ?
C37 C38 1.380(2) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 N6 1.456(2) . ?
C39 C40 1.515(3) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 N6 1.467(2) . ?
C41 C42 1.523(3) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 C44 1.389(2) . ?
C43 C48 1.395(2) . ?
C44 C45 1.385(2) . ?
C44 O8 1.3888(19) . ?
C45 C46 1.408(2) . ?
C45 H45 0.9300 . ?
C46 N5 1.379(2) . ?
C46 C47 1.415(2) . ?
C47 C48 1.375(2) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
C49 N5 1.461(2) . ?
C49 C50 1.521(3) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C51 N5 1.467(2) . ?
C51 C52 1.527(3) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
N1 H100 0.92(2) . ?
N2 H101 0.88(2) . ?
O200 H201 0.952(19) . ?
O200 H200 0.991(19) . ?

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
O4 C1 C2 121.48(18) . . ?
O4 C1 C11 118.40(16) . . ?
C2 C1 C11 120.11(18) . . ?
C3 C2 C1 120.63(19) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.21(18) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C12 119.69(19) . . ?
C3 C4 H4 120.2 . . ?
C12 C4 H4 120.2 . . ?
C6 C5 C13 120.27(19) . . ?
C6 C5 H5 119.9 . . ?
C13 C5 H5 119.9 . . ?
C5 C6 C7 119.98(19) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 120.85(19) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
O3 C8 C7 121.43(17) . . ?
O3 C8 C14 118.32(17) . . ?
C7 C8 C14 120.25(17) . . ?
O1 C9 C13 120.63(19) . . ?
O1 C9 C12 120.50(18) . . ?
C13 C9 C12 118.79(17) . . ?
O2 C10 C14 121.63(17) . . ?
O2 C10 C11 120.80(17) . . ?
C14 C10 C11 117.56(16) . . ?
C1 C11 C12 117.80(17) . . ?
C1 C11 C10 122.05(17) . . ?
C12 C11 C10 120.15(17) . . ?
C4 C12 C11 121.51(19) . . ?
C4 C12 C9 117.59(18) . . ?
C11 C12 C9 120.85(17) . . ?
C5 C13 C14 121.44(18) . . ?
C5 C13 C9 117.73(17) . . ?
C14 C13 C9 120.81(17) . . ?
C8 C14 C13 117.22(17) . . ?
C8 C14 C10 122.23(17) . . ?
C13 C14 C10 120.52(17) . . ?
O3 C15 C16 110.22(15) . . ?
O3 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
O3 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
O6 C16 N2 123.80(19) . . ?
O6 C16 C15 117.98(18) . . ?
N2 C16 C15 118.22(17) . . ?
N2 C17 C18 112.75(16) . . ?
N2 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
N2 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
N3 C18 C17 114.89(16) . . ?
N3 C18 H18A 108.5 . . ?
C17 C18 H18A 108.5 . . ?
N3 C18 H18B 108.5 . . ?
C17 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
N3 C19 C20 112.81(16) . . ?
N3 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
N3 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
N1 C20 C19 110.27(17) . . ?
N1 C20 H20A 109.6 . . ?
C19 C20 H20A 109.6 . . ?
N1 C20 H20B 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
O5 C21 N1 123.0(2) . . ?
O5 C21 C22 119.18(19) . . ?
N1 C21 C22 117.83(18) . . ?
O4 C22 C21 109.85(16) . . ?
O4 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
O4 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
N3 C23 C24 109.75(14) . . ?
N3 C23 H23A 109.7 . . ?
C24 C23 H23A 109.7 . . ?
N3 C23 H23B 109.7 . . ?
C24 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
N4 C24 C23 112.11(14) . . ?
N4 C24 H24A 109.2 . . ?
C23 C24 H24A 109.2 . . ?
N4 C24 H24B 109.2 . . ?
C23 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
O7 C25 N4 125.01(16) . . ?
O7 C25 C26 128.55(15) . . ?
N4 C25 C26 106.44(14) . . ?
C31 C26 C27 121.01(16) . . ?
C31 C26 C25 108.37(15) . . ?
C27 C26 C25 130.62(16) . . ?
C28 C27 C26 118.26(17) . . ?
C28 C27 H27 120.9 . . ?
C26 C27 H27 120.9 . . ?
C27 C28 C29 120.44(17) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C30 C29 C28 121.04(17) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C29 118.10(17) . . ?
C31 C30 H30 121.0 . . ?
C29 C30 H30 121.0 . . ?
C30 C31 C26 121.14(16) . . ?
C30 C31 C32 128.41(15) . . ?
C26 C31 C32 110.44(15) . . ?
N4 C32 C43 110.81(13) . . ?
N4 C32 C33 112.70(13) . . ?
C43 C32 C33 109.71(13) . . ?
N4 C32 C31 100.40(13) . . ?
C43 C32 C31 110.84(13) . . ?
C33 C32 C31 112.12(14) . . ?
C34 C33 C38 116.56(15) . . ?
C34 C33 C32 121.06(15) . . ?
C38 C33 C32 122.33(15) . . ?
C33 C34 O8 122.98(15) . . ?
C33 C34 C35 122.34(16) . . ?
O8 C34 C35 114.66(14) . . ?
C34 C35 C36 120.71(16) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
N6 C36 C35 121.77(16) . . ?
N6 C36 C37 121.10(16) . . ?
C35 C36 C37 117.08(15) . . ?
C38 C37 C36 120.62(16) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 H37 119.7 . . ?
C37 C38 C33 122.60(16) . . ?
C37 C38 H38 118.7 . . ?
C33 C38 H38 118.7 . . ?
N6 C39 C40 114.76(15) . . ?
N6 C39 H39A 108.6 . . ?
C40 C39 H39A 108.6 . . ?
N6 C39 H39B 108.6 . . ?
C40 C39 H39B 108.6 . . ?
H39A C39 H39B 107.6 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N6 C41 C42 114.11(15) . . ?
N6 C41 H41A 108.7 . . ?
C42 C41 H41A 108.7 . . ?
N6 C41 H41B 108.7 . . ?
C42 C41 H41B 108.7 . . ?
H41A C41 H41B 107.6 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 C48 116.19(15) . . ?
C44 C43 C32 121.72(15) . . ?
C48 C43 C32 121.90(15) . . ?
C45 C44 O8 115.32(14) . . ?
C45 C44 C43 122.67(15) . . ?
O8 C44 C43 122.01(15) . . ?
C44 C45 C46 120.65(15) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
N5 C46 C45 121.62(15) . . ?
N5 C46 C47 121.47(15) . . ?
C45 C46 C47 116.88(15) . . ?
C48 C47 C46 120.68(16) . . ?
C48 C47 H47 119.7 . . ?
C46 C47 H47 119.7 . . ?
C47 C48 C43 122.84(16) . . ?
C47 C48 H48 118.6 . . ?
C43 C48 H48 118.6 . . ?
N5 C49 C50 114.68(15) . . ?
N5 C49 H49A 108.6 . . ?
C50 C49 H49A 108.6 . . ?
N5 C49 H49B 108.6 . . ?
C50 C49 H49B 108.6 . . ?
H49A C49 H49B 107.6 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
N5 C51 C52 115.51(16) . . ?
N5 C51 H51A 108.4 . . ?
C52 C51 H51A 108.4 . . ?
N5 C51 H51B 108.4 . . ?
C52 C51 H51B 108.4 . . ?
H51A C51 H51B 107.5 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C21 N1 C20 120.81(18) . . ?
C21 N1 H100 118.6(15) . . ?
C20 N1 H100 120.5(15) . . ?
C16 N2 C17 120.23(17) . . ?
C16 N2 H101 116.0(15) . . ?
C17 N2 H101 123.2(15) . . ?
C23 N3 C19 110.46(14) . . ?
C23 N3 C18 113.63(15) . . ?
C19 N3 C18 109.54(15) . . ?
C25 N4 C24 122.57(14) . . ?
C25 N4 C32 114.23(14) . . ?
C24 N4 C32 122.68(13) . . ?
C46 N5 C49 120.37(14) . . ?
C46 N5 C51 120.30(15) . . ?
C49 N5 C51 116.65(14) . . ?
C36 N6 C39 120.94(15) . . ?
C36 N6 C41 121.70(15) . . ?
C39 N6 C41 117.32(14) . . ?
C8 O3 C15 116.16(15) . . ?
C1 O4 C22 118.93(15) . . ?
C34 O8 C44 118.04(13) . . ?
H201 O200 H200 99(4) . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.049

_shelxl_version_number           2014-1

