# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1556207'
_audit_update_record             
;
2017-06-15 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H25 N O8'
_chemical_formula_sum            'C26 H25 N O8'
_chemical_formula_weight         479.47

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/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                   10.1470(9)
_cell_length_b                   20.9021(16)
_cell_length_c                   11.8600(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.529(2)
_cell_angle_gamma                90
_cell_volume                     2370.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8766
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.81

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21159
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.066
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4651
_reflns_number_gt                3275
_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-2014/7 (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)+(0.0967P)²+0.3599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4651
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1674
_refine_ls_wR_factor_gt          0.1555
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.4251(2) 0.71488(9) 0.09191(19) 0.0417(5) Uani 1 1 d . . . . .
C2 C 0.3208(2) 0.72449(10) -0.02707(19) 0.0450(5) Uani 1 1 d . . . . .
C3 C 0.2336(2) 0.77668(12) -0.0713(2) 0.0613(7) Uani 1 1 d . . . . .
H3 H 0.2346 0.8119 -0.0232 0.074 Uiso 1 1 calc R U . . .
C4 C 0.1464(3) 0.77454(15) -0.1876(3) 0.0786(9) Uani 1 1 d . . . . .
H4 H 0.0866 0.8087 -0.2186 0.094 Uiso 1 1 calc R U . . .
C5 C 0.1455(3) 0.72224(17) -0.2604(3) 0.0807(9) Uani 1 1 d . . . . .
H5 H 0.0867 0.7226 -0.3396 0.097 Uiso 1 1 calc R U . . .
C6 C 0.2303(3) 0.66979(13) -0.2172(2) 0.0639(7) Uani 1 1 d . . . . .
H6 H 0.2289 0.6346 -0.2655 0.077 Uiso 1 1 calc R U . . .
C7 C 0.3180(2) 0.67171(10) -0.09853(18) 0.0453(5) Uani 1 1 d . . . . .
C8 C 0.4147(2) 0.62222(9) -0.02954(17) 0.0392(5) Uani 1 1 d . . . . .
C9 C 0.48565(19) 0.64719(8) 0.09805(17) 0.0361(4) Uani 1 1 d . . . . .
C10 C 0.64725(19) 0.64635(8) 0.13547(17) 0.0359(4) Uani 1 1 d . . . . .
H10 H 0.6827 0.6709 0.2100 0.043 Uiso 1 1 calc R U . . .
C11 C 0.70838(19) 0.67670(9) 0.04837(16) 0.0372(4) Uani 1 1 d . . . . .
C12 C 0.7464(2) 0.74066(10) 0.06244(18) 0.0463(5) Uani 1 1 d . . . . .
H12 H 0.7322 0.7638 0.1244 0.056 Uiso 1 1 calc R U . . .
C13 C 0.8044(2) 0.77078(11) -0.01250(19) 0.0538(6) Uani 1 1 d . . . . .
H13 H 0.8297 0.8137 -0.0008 0.065 Uiso 1 1 calc R U . . .
C14 C 0.8250(2) 0.73745(12) -0.1046(2) 0.0557(6) Uani 1 1 d . . . . .
H14 H 0.8660 0.7573 -0.1547 0.067 Uiso 1 1 calc R U . . .
C15 C 0.7846(3) 0.67458(12) -0.1223(2) 0.0571(6) Uani 1 1 d . . . . .
H15 H 0.7964 0.6523 -0.1862 0.068 Uiso 1 1 calc R U . . .
C16 C 0.7268(2) 0.64383(10) -0.04713(19) 0.0480(5) Uani 1 1 d . . . . .
H16 H 0.7003 0.6011 -0.0603 0.058 Uiso 1 1 calc R U . . .
C17 C 0.6834(2) 0.57597(9) 0.16864(17) 0.0385(5) Uani 1 1 d . . . . .
H17 H 0.6807 0.5517 0.0972 0.046 Uiso 1 1 calc R U . . .
C18 C 0.8268(2) 0.56994(10) 0.26338(19) 0.0476(5) Uani 1 1 d . . . . .
C19 C 1.0316(3) 0.50751(16) 0.3422(3) 0.0866(9) Uani 1 1 d . . . . .
H19A H 1.0940 0.5410 0.3341 0.104 Uiso 1 1 calc R U . . .
H19B H 1.0265 0.5098 0.4223 0.104 Uiso 1 1 calc R U . . .
C20 C 1.0848(4) 0.44701(15) 0.3246(5) 0.1308(17) Uani 1 1 d . . . . .
H20A H 1.0232 0.4139 0.3331 0.196 Uiso 1 1 calc R U . . .
H20B H 1.1759 0.4410 0.3830 0.196 Uiso 1 1 calc R U . . .
H20C H 1.0914 0.4452 0.2458 0.196 Uiso 1 1 calc R U . . .
C21 C 0.46372(19) 0.60058(8) 0.19556(17) 0.0364(4) Uani 1 1 d . . . . .
C22 C 0.3211(2) 0.56901(10) 0.14581(18) 0.0440(5) Uani 1 1 d . . . . .
C23 C 0.0795(3) 0.59303(18) 0.0616(3) 0.0913(10) Uani 1 1 d . . . . .
H23A H 0.0745 0.5707 -0.0104 0.137 Uiso 1 1 calc R U . . .
H23B H 0.0189 0.6296 0.0420 0.137 Uiso 1 1 calc R U . . .
H23C H 0.0509 0.5650 0.1133 0.137 Uiso 1 1 calc R U . . .
C24 C 0.4805(2) 0.63694(9) 0.31251(18) 0.0448(5) Uani 1 1 d . . . . .
H24A H 0.5764 0.6517 0.3462 0.054 Uiso 1 1 calc R U . . .
H24B H 0.4205 0.6743 0.2940 0.054 Uiso 1 1 calc R U . . .
C25 C 0.4458(2) 0.59775(10) 0.40458(18) 0.0451(5) Uani 1 1 d . . . . .
C26 C 0.4911(4) 0.58539(14) 0.6129(2) 0.0818(9) Uani 1 1 d . . . . .
H26A H 0.3939 0.5740 0.5867 0.123 Uiso 1 1 calc R U . . .
H26B H 0.5105 0.6153 0.6779 0.123 Uiso 1 1 calc R U . . .
H26C H 0.5470 0.5477 0.6393 0.123 Uiso 1 1 calc R U . . .
N1 N 0.57403(17) 0.55209(8) 0.21521(15) 0.0445(4) Uani 1 1 d . . . . .
H1 H 0.5750 0.5155 0.2486 0.33(4) Uiso 1 1 calc R . . . .
O4 O 0.89127(17) 0.51731(8) 0.25362(16) 0.0668(5) Uani 1 1 d . . . . .
O1 O 0.46200(18) 0.75465(6) 0.17073(15) 0.0585(4) Uani 1 1 d . . . . .
O2 O 0.43448(16) 0.57025(7) -0.06602(13) 0.0551(4) Uani 1 1 d . . . . .
O3 O 0.8791(2) 0.60891(11) 0.3382(2) 0.1144(9) Uani 1 1 d . . . . .
O5 O 0.30006(18) 0.51342(7) 0.12407(17) 0.0692(5) Uani 1 1 d . . . . .
O6 O 0.22138(15) 0.61377(7) 0.12165(14) 0.0547(4) Uani 1 1 d . . . . .
O7 O 0.35486(19) 0.55914(9) 0.38363(15) 0.0717(5) Uani 1 1 d . . . . .
O8 O 0.52448(19) 0.61442(8) 0.51438(14) 0.0656(5) 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
C1 O1 1.213(2) . ?
C1 C2 1.467(3) . ?
C1 C9 1.534(3) . ?
C2 C7 1.386(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.369(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.391(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.472(3) . ?
C8 O2 1.211(2) . ?
C8 C9 1.534(3) . ?
C9 C10 1.549(3) . ?
C9 C21 1.584(3) . ?
C10 C11 1.511(3) . ?
C10 C17 1.535(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.386(3) . ?
C11 C16 1.390(3) . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N1 1.482(3) . ?
C17 C18 1.518(3) . ?
C17 H17 0.9800 . ?
C18 O3 1.191(3) . ?
C18 O4 1.305(2) . ?
C19 C20 1.418(4) . ?
C19 O4 1.474(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N1 1.470(2) . ?
C21 C22 1.519(3) . ?
C21 C24 1.540(3) . ?
C22 O5 1.194(2) . ?
C22 O6 1.337(2) . ?
C23 O6 1.443(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.498(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O7 1.188(3) . ?
C25 O8 1.326(3) . ?
C26 O8 1.454(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N1 H1 0.8600 . ?

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
O1 C1 C2 125.80(18) . . ?
O1 C1 C9 125.44(19) . . ?
C2 C1 C9 108.69(17) . . ?
C7 C2 C3 120.9(2) . . ?
C7 C2 C1 109.89(17) . . ?
C3 C2 C1 129.2(2) . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 117.4(3) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
C2 C7 C6 121.1(2) . . ?
C2 C7 C8 110.23(18) . . ?
C6 C7 C8 128.6(2) . . ?
O2 C8 C7 126.25(19) . . ?
O2 C8 C9 125.38(18) . . ?
C7 C8 C9 108.36(16) . . ?
C8 C9 C1 102.63(15) . . ?
C8 C9 C10 112.42(15) . . ?
C1 C9 C10 113.12(15) . . ?
C8 C9 C21 112.15(14) . . ?
C1 C9 C21 116.76(14) . . ?
C10 C9 C21 100.22(14) . . ?
C11 C10 C17 117.40(15) . . ?
C11 C10 C9 115.88(15) . . ?
C17 C10 C9 102.92(14) . . ?
C11 C10 H10 106.6 . . ?
C17 C10 H10 106.6 . . ?
C9 C10 H10 106.6 . . ?
C12 C11 C16 117.84(18) . . ?
C12 C11 C10 118.96(17) . . ?
C16 C11 C10 123.20(17) . . ?
C13 C12 C11 121.8(2) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 119.5(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 119.9(2) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
N1 C17 C18 110.39(16) . . ?
N1 C17 C10 105.90(15) . . ?
C18 C17 C10 110.91(16) . . ?
N1 C17 H17 109.9 . . ?
C18 C17 H17 109.9 . . ?
C10 C17 H17 109.9 . . ?
O3 C18 O4 122.1(2) . . ?
O3 C18 C17 124.96(19) . . ?
O4 C18 C17 112.92(18) . . ?
C20 C19 O4 110.1(3) . . ?
C20 C19 H19A 109.6 . . ?
O4 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
O4 C19 H19B 109.6 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 C22 109.75(15) . . ?
N1 C21 C24 110.38(16) . . ?
C22 C21 C24 111.63(15) . . ?
N1 C21 C9 104.75(14) . . ?
C22 C21 C9 109.38(15) . . ?
C24 C21 C9 110.72(14) . . ?
O5 C22 O6 124.5(2) . . ?
O5 C22 C21 125.8(2) . . ?
O6 C22 C21 109.50(16) . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C21 113.85(16) . . ?
C25 C24 H24A 108.8 . . ?
C21 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C21 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
O7 C25 O8 123.7(2) . . ?
O7 C25 C24 125.1(2) . . ?
O8 C25 C24 111.16(19) . . ?
O8 C26 H26A 109.5 . . ?
O8 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O8 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 N1 C17 109.51(15) . . ?
C21 N1 H1 125.2 . . ?
C17 N1 H1 125.2 . . ?
C18 O4 C19 116.58(19) . . ?
C22 O6 C23 117.0(2) . . ?
C25 O8 C26 117.0(2) . . ?

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_1f
_database_code_depnum_ccdc_archive 'CCDC 1556209'
_audit_update_record             
;
2017-06-15 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 F N O8'
_chemical_formula_sum            'C26 H24 F N O8'
_chemical_formula_weight         497.46

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'
F F 0.0171 0.0103 '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                   10.1592(18)
_cell_length_b                   13.747(2)
_cell_length_c                   17.824(3)
_cell_angle_alpha                90.023(5)
_cell_angle_beta                 93.750(5)
_cell_angle_gamma                101.015(5)
_cell_volume                     2437.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9168
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      23.22

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28527
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.278
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             8410
_reflns_number_gt                5150
_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-2014/7 (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)+(0.0870P)²+0.9592P] 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         8410
_refine_ls_number_parameters     643
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1735
_refine_ls_wR_factor_gt          0.1479
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.6238(3) 0.5722(2) 0.62374(16) 0.0387(7) Uani 1 1 d . . . . .
H1 H 0.6534 0.5591 0.5741 0.046 Uiso 1 1 calc R U . . .
C2 C 0.7124(3) 0.5351(2) 0.68472(19) 0.0499(8) Uani 1 1 d . . . . .
C3 C 0.8543(4) 0.4205(3) 0.7135(2) 0.0883(13) Uani 1 1 d . . . . .
H3A H 0.9268 0.4711 0.7350 0.106 Uiso 1 1 calc R U . . .
H3B H 0.8025 0.3896 0.7540 0.106 Uiso 1 1 calc R U . . .
C4 C 0.9083(4) 0.3465(3) 0.6727(3) 0.1000(15) Uani 1 1 d . . . . .
H4A H 0.8357 0.2967 0.6519 0.150 Uiso 1 1 calc R U . . .
H4B H 0.9656 0.3162 0.7065 0.150 Uiso 1 1 calc R U . . .
H4C H 0.9592 0.3779 0.6328 0.150 Uiso 1 1 calc R U . . .
C5 C 0.4002(3) 0.5969(2) 0.64057(15) 0.0366(7) Uani 1 1 d . . . . .
C6 C 0.2670(3) 0.5680(2) 0.59459(17) 0.0426(7) Uani 1 1 d . . . . .
C7 C 0.0598(4) 0.6184(3) 0.5661(3) 0.0893(13) Uani 1 1 d . . . . .
H7A H 0.0714 0.6205 0.5131 0.134 Uiso 1 1 calc R U . . .
H7B H 0.0129 0.6695 0.5795 0.134 Uiso 1 1 calc R U . . .
H7C H 0.0088 0.5549 0.5785 0.134 Uiso 1 1 calc R U . . .
C8 C 0.3781(3) 0.6056(2) 0.72430(16) 0.0487(8) Uani 1 1 d . . . . .
H8A H 0.4645 0.6160 0.7527 0.058 Uiso 1 1 calc R U . . .
H8B H 0.3381 0.6631 0.7323 0.058 Uiso 1 1 calc R U . . .
C9 C 0.2893(4) 0.5156(3) 0.75342(19) 0.0529(8) Uani 1 1 d . . . . .
C10 C 0.2250(5) 0.4220(4) 0.8594(3) 0.1083(16) Uani 1 1 d . . . . .
H10A H 0.1351 0.4347 0.8563 0.163 Uiso 1 1 calc R U . . .
H10B H 0.2546 0.4162 0.9112 0.163 Uiso 1 1 calc R U . . .
H10C H 0.2264 0.3613 0.8330 0.163 Uiso 1 1 calc R U . . .
C11 C 0.4572(3) 0.7042(2) 0.52464(15) 0.0353(6) Uani 1 1 d . . . . .
C12 C 0.4069(3) 0.7963(2) 0.50917(15) 0.0371(7) Uani 1 1 d . . . . .
C13 C 0.3686(3) 0.8338(2) 0.44098(17) 0.0494(8) Uani 1 1 d . . . . .
H13 H 0.3713 0.7999 0.3961 0.059 Uiso 1 1 calc R U . . .
C14 C 0.3261(3) 0.9234(3) 0.4416(2) 0.0597(9) Uani 1 1 d . . . . .
H14 H 0.2997 0.9502 0.3964 0.072 Uiso 1 1 calc R U . . .
C15 C 0.3220(3) 0.9742(2) 0.5084(2) 0.0582(9) Uani 1 1 d . . . . .
H15 H 0.2925 1.0342 0.5073 0.070 Uiso 1 1 calc R U . . .
C16 C 0.3606(3) 0.9377(2) 0.57588(19) 0.0494(8) Uani 1 1 d . . . . .
H16 H 0.3584 0.9722 0.6205 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4032(3) 0.8477(2) 0.57592(16) 0.0377(7) Uani 1 1 d . . . . .
C18 C 0.4523(3) 0.7934(2) 0.63945(17) 0.0394(7) Uani 1 1 d . . . . .
C19 C 0.4835(3) 0.69590(19) 0.60976(14) 0.0339(6) Uani 1 1 d . . . . .
C20 C 0.6285(3) 0.68405(19) 0.63430(15) 0.0371(7) Uani 1 1 d . . . . .
H20 H 0.6396 0.6968 0.6887 0.045 Uiso 1 1 calc R U . . .
C21 C 0.7422(3) 0.7531(2) 0.60105(17) 0.0419(7) Uani 1 1 d . . . . .
C22 C 0.7803(3) 0.7402(2) 0.52822(19) 0.0534(8) Uani 1 1 d . . . . .
H22 H 0.7334 0.6884 0.4977 0.064 Uiso 1 1 calc R U . . .
C23 C 0.8864(4) 0.8040(3) 0.5025(2) 0.0730(11) Uani 1 1 d . . . . .
C24 C 0.9594(4) 0.8811(3) 0.5448(4) 0.0894(15) Uani 1 1 d . . . . .
H24 H 1.0320 0.9232 0.5257 0.107 Uiso 1 1 calc R U . . .
C25 C 0.9230(4) 0.8946(3) 0.6161(3) 0.0875(13) Uani 1 1 d . . . . .
H25 H 0.9717 0.9463 0.6461 0.105 Uiso 1 1 calc R U . . .
C26 C 0.8142(3) 0.8321(2) 0.6439(2) 0.0633(9) Uani 1 1 d . . . . .
H26 H 0.7891 0.8432 0.6919 0.076 Uiso 1 1 calc R U . . .
C27 C 0.4918(3) -0.0356(2) 0.88610(16) 0.0389(7) Uani 1 1 d . . . . .
H27 H 0.4704 -0.0470 0.9386 0.047 Uiso 1 1 calc R U . . .
C28 C 0.5905(3) -0.0989(2) 0.86491(17) 0.0454(8) Uani 1 1 d . . . . .
C29 C 0.6399(5) -0.2609(3) 0.8736(2) 0.0826(13) Uani 1 1 d . . . . .
H29A H 0.5832 -0.3263 0.8723 0.099 Uiso 1 1 calc R U . . .
H29B H 0.6692 -0.2466 0.8234 0.099 Uiso 1 1 calc R U . . .
C30 C 0.7535(5) -0.2612(4) 0.9236(3) 0.1165(19) Uani 1 1 d . . . . .
H30A H 0.8156 -0.1994 0.9203 0.175 Uiso 1 1 calc R U . . .
H30B H 0.7964 -0.3147 0.9104 0.175 Uiso 1 1 calc R U . . .
H30C H 0.7259 -0.2696 0.9740 0.175 Uiso 1 1 calc R U . . .
C31 C 0.4433(3) 0.12233(19) 0.85050(14) 0.0358(6) Uani 1 1 d . . . . .
C32 C 0.4711(3) 0.1651(2) 0.77257(16) 0.0437(7) Uani 1 1 d . . . . .
C33 C 0.4017(5) 0.2738(3) 0.6819(2) 0.0824(12) Uani 1 1 d . . . . .
H33A H 0.4907 0.3099 0.6752 0.124 Uiso 1 1 calc R U . . .
H33B H 0.3387 0.3174 0.6751 0.124 Uiso 1 1 calc R U . . .
H33C H 0.3794 0.2206 0.6455 0.124 Uiso 1 1 calc R U . . .
C34 C 0.4381(3) 0.2068(2) 0.90565(16) 0.0447(7) Uani 1 1 d . . . . .
H34A H 0.3552 0.2308 0.8950 0.054 Uiso 1 1 calc R U . . .
H34B H 0.4375 0.1813 0.9564 0.054 Uiso 1 1 calc R U . . .
C35 C 0.5544(4) 0.2914(2) 0.90135(19) 0.0552(8) Uani 1 1 d . . . . .
C36 C 0.6397(5) 0.4576(3) 0.9356(3) 0.1192(18) Uani 1 1 d . . . . .
H36A H 0.7222 0.4466 0.9605 0.179 Uiso 1 1 calc R U . . .
H36B H 0.6121 0.5125 0.9592 0.179 Uiso 1 1 calc R U . . .
H36C H 0.6530 0.4720 0.8837 0.179 Uiso 1 1 calc R U . . .
C37 C 0.2257(3) 0.04611(19) 0.91212(16) 0.0372(7) Uani 1 1 d . . . . .
C38 C 0.1023(3) 0.0815(2) 0.88700(15) 0.0378(7) Uani 1 1 d . . . . .
C39 C 0.0025(3) 0.1049(2) 0.92914(18) 0.0512(8) Uani 1 1 d . . . . .
H39 H 0.0066 0.0986 0.9812 0.061 Uiso 1 1 calc R U . . .
C40 C -0.1027(3) 0.1374(3) 0.8916(2) 0.0672(10) Uani 1 1 d . . . . .
H40 H -0.1706 0.1538 0.9187 0.081 Uiso 1 1 calc R U . . .
C41 C -0.1100(3) 0.1466(3) 0.8143(2) 0.0647(10) Uani 1 1 d . . . . .
H41 H -0.1825 0.1692 0.7906 0.078 Uiso 1 1 calc R U . . .
C42 C -0.0122(3) 0.1228(2) 0.77193(19) 0.0532(8) Uani 1 1 d . . . . .
H42 H -0.0175 0.1286 0.7199 0.064 Uiso 1 1 calc R U . . .
C43 C 0.0945(3) 0.0900(2) 0.80937(16) 0.0398(7) Uani 1 1 d . . . . .
C44 C 0.2102(3) 0.0588(2) 0.77785(16) 0.0403(7) Uani 1 1 d . . . . .
C45 C 0.3088(3) 0.04208(19) 0.84345(14) 0.0349(6) Uani 1 1 d . . . . .
C46 C 0.3618(3) -0.05521(19) 0.83449(15) 0.0367(7) Uani 1 1 d . . . . .
H46 H 0.3896 -0.0564 0.7829 0.044 Uiso 1 1 calc R U . . .
C47 C 0.2586(3) -0.1483(2) 0.84312(18) 0.0457(8) Uani 1 1 d . . . . .
C48 C 0.2399(4) -0.1967(2) 0.9107(2) 0.0642(9) Uani 1 1 d . . . . .
H48 H 0.2915 -0.1728 0.9542 0.077 Uiso 1 1 calc R U . . .
C49 C 0.1418(5) -0.2821(3) 0.9115(3) 0.085 Uani 1 1 d . . . . .
C50 C 0.0634(4) -0.3197(3) 0.8504(3) 0.092 Uani 1 1 d . . . . .
H50 H -0.0011 -0.3771 0.8541 0.110 Uiso 1 1 calc R U . . .
C51 C 0.0791(4) -0.2727(3) 0.7829(3) 0.0858(12) Uani 1 1 d . . . . .
H51 H 0.0255 -0.2970 0.7401 0.103 Uiso 1 1 calc R U . . .
C52 C 0.1772(3) -0.1880(3) 0.7805(2) 0.0617(9) Uani 1 1 d . . . . .
H52 H 0.1894 -0.1561 0.7348 0.074 Uiso 1 1 calc R U . . .
F1 F 0.9226(3) 0.7911(2) 0.43202(16) 0.1175(10) Uani 1 1 d . . . . .
F2 F 0.1242(4) -0.3294(2) 0.97624(19) 0.1588(13) Uani 1 1 d . . . . .
N1 N 0.4836(2) 0.52352(16) 0.62918(13) 0.0436(6) Uani 1 1 d . . . . .
H1A H 0.4545 0.4606 0.6261 0.052 Uiso 1 1 calc R U . . .
N2 N 0.5482(2) 0.06809(17) 0.87570(14) 0.0469(6) Uani 1 1 d . . . . .
H2 H 0.6320 0.0942 0.8833 0.056 Uiso 1 1 calc R U . . .
O1 O 0.7275(3) 0.5645(2) 0.74843(16) 0.1014(11) Uani 1 1 d . . . . .
O2 O 0.7684(2) 0.46425(18) 0.65975(13) 0.0694(7) Uani 1 1 d . . . . .
O3 O 0.2378(2) 0.50042(18) 0.55081(13) 0.0645(6) Uani 1 1 d . . . . .
O4 O 0.1897(2) 0.63386(16) 0.60687(12) 0.0562(6) Uani 1 1 d . . . . .
O5 O 0.2045(3) 0.4608(2) 0.71691(16) 0.0903(9) Uani 1 1 d . . . . .
O6 O 0.3142(3) 0.5033(2) 0.82562(13) 0.0827(8) Uani 1 1 d . . . . .
O7 O 0.4761(2) 0.64444(15) 0.47831(11) 0.0491(5) Uani 1 1 d . . . . .
O8 O 0.4706(2) 0.82139(15) 0.70463(12) 0.0564(6) Uani 1 1 d . . . . .
O9 O 0.6801(2) -0.07181(18) 0.82491(13) 0.0642(6) Uani 1 1 d . . . . .
O10 O 0.5619(2) -0.18840(16) 0.89490(12) 0.0605(6) Uani 1 1 d . . . . .
O11 O 0.5463(2) 0.13941(17) 0.73075(12) 0.0616(6) Uani 1 1 d . . . . .
O12 O 0.3961(2) 0.23354(15) 0.75693(11) 0.0523(6) Uani 1 1 d . . . . .
O13 O 0.6503(3) 0.29175(18) 0.86591(16) 0.0806(8) Uani 1 1 d . . . . .
O14 O 0.5352(3) 0.36845(18) 0.94105(16) 0.0842(8) Uani 1 1 d . . . . .
O15 O 0.2576(2) 0.02435(16) 0.97552(11) 0.0517(6) Uani 1 1 d . . . . .
O16 O 0.2238(2) 0.04429(16) 0.71206(11) 0.0552(6) 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
C1 N1 1.462(4) . ?
C1 C2 1.517(4) . ?
C1 C20 1.541(4) . ?
C1 H1 0.9800 . ?
C2 O1 1.196(4) . ?
C2 O2 1.309(4) . ?
C3 C4 1.460(5) . ?
C3 O2 1.460(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 N1 1.458(3) . ?
C5 C6 1.520(4) . ?
C5 C8 1.532(4) . ?
C5 C19 1.579(4) . ?
C6 O3 1.193(3) . ?
C6 O4 1.333(3) . ?
C7 O4 1.442(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.500(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O5 1.187(4) . ?
C9 O6 1.313(4) . ?
C10 O6 1.456(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O7 1.214(3) . ?
C11 C12 1.473(4) . ?
C11 C19 1.531(4) . ?
C12 C13 1.382(4) . ?
C12 C17 1.390(4) . ?
C13 C14 1.381(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.366(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.469(4) . ?
C18 O8 1.215(3) . ?
C18 C19 1.537(4) . ?
C19 C20 1.548(4) . ?
C20 C21 1.502(4) . ?
C20 H20 0.9800 . ?
C21 C26 1.385(4) . ?
C21 C22 1.399(4) . ?
C22 C23 1.359(5) . ?
C22 H22 0.9300 . ?
C23 F1 1.352(5) . ?
C23 C24 1.367(6) . ?
C24 C25 1.369(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 N2 1.448(4) . ?
C27 C28 1.513(4) . ?
C27 C46 1.538(4) . ?
C27 H27 0.9800 . ?
C28 O9 1.196(4) . ?
C28 O10 1.330(4) . ?
C29 C30 1.412(6) . ?
C29 O10 1.451(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 N2 1.461(3) . ?
C31 C32 1.531(4) . ?
C31 C34 1.532(4) . ?
C31 C45 1.582(4) . ?
C32 O11 1.200(3) . ?
C32 O12 1.338(3) . ?
C33 O12 1.448(4) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.498(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 O13 1.194(4) . ?
C35 O14 1.325(4) . ?
C36 O14 1.467(5) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 O15 1.209(3) . ?
C37 C38 1.473(4) . ?
C37 C45 1.539(4) . ?
C38 C39 1.385(4) . ?
C38 C43 1.387(4) . ?
C39 C40 1.371(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.381(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.373(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.384(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.470(4) . ?
C44 O16 1.211(3) . ?
C44 C45 1.536(4) . ?
C45 C46 1.546(4) . ?
C46 C47 1.507(4) . ?
C46 H46 0.9800 . ?
C47 C48 1.382(4) . ?
C47 C52 1.390(5) . ?
C48 C49 1.388(5) . ?
C48 H48 0.9300 . ?
C49 F2 1.331(5) . ?
C49 C50 1.346(6) . ?
C50 C51 1.370(6) . ?
C50 H50 0.9300 . ?
C51 C52 1.384(5) . ?
C51 H51 0.9300 . ?
C52 H52 0.9300 . ?
N1 H1A 0.8600 . ?
N2 H2 0.8600 . ?

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
N1 C1 C2 110.2(2) . . ?
N1 C1 C20 106.4(2) . . ?
C2 C1 C20 110.3(2) . . ?
N1 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
C20 C1 H1 110.0 . . ?
O1 C2 O2 123.5(3) . . ?
O1 C2 C1 124.8(3) . . ?
O2 C2 C1 111.7(3) . . ?
C4 C3 O2 107.3(3) . . ?
C4 C3 H3A 110.3 . . ?
O2 C3 H3A 110.3 . . ?
C4 C3 H3B 110.3 . . ?
O2 C3 H3B 110.3 . . ?
H3A C3 H3B 108.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 109.8(2) . . ?
N1 C5 C8 109.9(2) . . ?
C6 C5 C8 111.0(2) . . ?
N1 C5 C19 104.1(2) . . ?
C6 C5 C19 110.0(2) . . ?
C8 C5 C19 111.8(2) . . ?
O3 C6 O4 124.5(3) . . ?
O3 C6 C5 125.8(3) . . ?
O4 C6 C5 109.5(3) . . ?
O4 C7 H7A 109.5 . . ?
O4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C5 112.9(3) . . ?
C9 C8 H8A 109.0 . . ?
C5 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C5 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O5 C9 O6 122.5(3) . . ?
O5 C9 C8 125.3(3) . . ?
O6 C9 C8 112.3(3) . . ?
O6 C10 H10A 109.5 . . ?
O6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C11 C12 126.4(2) . . ?
O7 C11 C19 125.0(2) . . ?
C12 C11 C19 108.6(2) . . ?
C13 C12 C17 120.8(3) . . ?
C13 C12 C11 129.1(3) . . ?
C17 C12 C11 110.1(2) . . ?
C14 C13 C12 117.8(3) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C13 C14 C15 121.1(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 118.1(3) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C16 C17 C12 120.9(3) . . ?
C16 C17 C18 129.2(3) . . ?
C12 C17 C18 109.8(2) . . ?
O8 C18 C17 126.4(3) . . ?
O8 C18 C19 124.7(3) . . ?
C17 C18 C19 108.8(2) . . ?
C11 C19 C18 102.6(2) . . ?
C11 C19 C20 113.9(2) . . ?
C18 C19 C20 111.8(2) . . ?
C11 C19 C5 111.6(2) . . ?
C18 C19 C5 116.7(2) . . ?
C20 C19 C5 100.8(2) . . ?
C21 C20 C1 116.8(2) . . ?
C21 C20 C19 117.7(2) . . ?
C1 C20 C19 103.3(2) . . ?
C21 C20 H20 106.0 . . ?
C1 C20 H20 106.0 . . ?
C19 C20 H20 106.0 . . ?
C26 C21 C22 118.1(3) . . ?
C26 C21 C20 119.4(3) . . ?
C22 C21 C20 122.5(3) . . ?
C23 C22 C21 119.4(4) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
F1 C23 C22 119.1(4) . . ?
F1 C23 C24 118.0(4) . . ?
C22 C23 C24 122.9(4) . . ?
C23 C24 C25 118.3(4) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
C24 C25 C26 120.5(4) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.8(4) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
N2 C27 C28 109.9(2) . . ?
N2 C27 C46 104.7(2) . . ?
C28 C27 C46 112.3(2) . . ?
N2 C27 H27 110.0 . . ?
C28 C27 H27 110.0 . . ?
C46 C27 H27 110.0 . . ?
O9 C28 O10 125.1(3) . . ?
O9 C28 C27 123.8(3) . . ?
O10 C28 C27 111.1(3) . . ?
C30 C29 O10 112.5(3) . . ?
C30 C29 H29A 109.1 . . ?
O10 C29 H29A 109.1 . . ?
C30 C29 H29B 109.1 . . ?
O10 C29 H29B 109.1 . . ?
H29A C29 H29B 107.8 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N2 C31 C32 109.7(2) . . ?
N2 C31 C34 110.7(2) . . ?
C32 C31 C34 109.4(2) . . ?
N2 C31 C45 105.3(2) . . ?
C32 C31 C45 108.5(2) . . ?
C34 C31 C45 113.1(2) . . ?
O11 C32 O12 124.9(3) . . ?
O11 C32 C31 125.2(3) . . ?
O12 C32 C31 109.9(2) . . ?
O12 C33 H33A 109.5 . . ?
O12 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O12 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C31 112.7(2) . . ?
C35 C34 H34A 109.0 . . ?
C31 C34 H34A 109.0 . . ?
C35 C34 H34B 109.0 . . ?
C31 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
O13 C35 O14 123.9(3) . . ?
O13 C35 C34 125.6(3) . . ?
O14 C35 C34 110.5(3) . . ?
O14 C36 H36A 109.5 . . ?
O14 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O14 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O15 C37 C38 126.4(2) . . ?
O15 C37 C45 125.4(2) . . ?
C38 C37 C45 108.1(2) . . ?
C39 C38 C43 120.7(3) . . ?
C39 C38 C37 129.4(3) . . ?
C43 C38 C37 109.9(2) . . ?
C40 C39 C38 117.7(3) . . ?
C40 C39 H39 121.1 . . ?
C38 C39 H39 121.1 . . ?
C39 C40 C41 121.5(3) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 H40 119.2 . . ?
C42 C41 C40 121.2(3) . . ?
C42 C41 H41 119.4 . . ?
C40 C41 H41 119.4 . . ?
C41 C42 C43 117.7(3) . . ?
C41 C42 H42 121.2 . . ?
C43 C42 H42 121.2 . . ?
C42 C43 C38 121.1(3) . . ?
C42 C43 C44 128.7(3) . . ?
C38 C43 C44 110.2(2) . . ?
O16 C44 C43 126.5(3) . . ?
O16 C44 C45 125.4(3) . . ?
C43 C44 C45 108.1(2) . . ?
C44 C45 C37 102.5(2) . . ?
C44 C45 C46 112.5(2) . . ?
C37 C45 C46 114.8(2) . . ?
C44 C45 C31 114.2(2) . . ?
C37 C45 C31 111.2(2) . . ?
C46 C45 C31 102.1(2) . . ?
C47 C46 C27 120.1(2) . . ?
C47 C46 C45 114.6(2) . . ?
C27 C46 C45 102.0(2) . . ?
C47 C46 H46 106.4 . . ?
C27 C46 H46 106.4 . . ?
C45 C46 H46 106.4 . . ?
C48 C47 C52 117.8(3) . . ?
C48 C47 C46 123.2(3) . . ?
C52 C47 C46 119.0(3) . . ?
C47 C48 C49 117.9(4) . . ?
C47 C48 H48 121.1 . . ?
C49 C48 H48 121.1 . . ?
F2 C49 C50 118.2(4) . . ?
F2 C49 C48 118.1(4) . . ?
C50 C49 C48 123.7(4) . . ?
C49 C50 C51 119.6(4) . . ?
C49 C50 H50 120.2 . . ?
C51 C50 H50 120.2 . . ?
C50 C51 C52 117.8(4) . . ?
C50 C51 H51 121.1 . . ?
C52 C51 H51 121.1 . . ?
C51 C52 C47 123.2(4) . . ?
C51 C52 H52 118.4 . . ?
C47 C52 H52 118.4 . . ?
C5 N1 C1 110.4(2) . . ?
C5 N1 H1A 124.8 . . ?
C1 N1 H1A 124.8 . . ?
C27 N2 C31 110.7(2) . . ?
C27 N2 H2 124.7 . . ?
C31 N2 H2 124.7 . . ?
C2 O2 C3 117.2(3) . . ?
C6 O4 C7 116.7(3) . . ?
C9 O6 C10 115.6(3) . . ?
C28 O10 C29 117.4(3) . . ?
C32 O12 C33 116.2(2) . . ?
C35 O14 C36 114.4(3) . . ?

_refine_diff_density_max         0.729
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 1556208'
_audit_update_record             
;
2017-06-15 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H27 N O9'
_chemical_formula_sum            'C27 H27 N O9'
_chemical_formula_weight         509.49

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      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                   10.557(3)
_cell_length_b                   11.363(3)
_cell_length_c                   12.920(3)
_cell_angle_alpha                112.497(7)
_cell_angle_beta                 102.659(7)
_cell_angle_gamma                105.650(7)
_cell_volume                     1285.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3490
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      22.60

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16873
_diffrn_reflns_av_unetI/netI     0.1585
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.830
_diffrn_reflns_theta_max         27.591
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             5783
_reflns_number_gt                2538
_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-2014/7 (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)+(0.0970P)²+0.5267P] 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         5783
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2146
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.2341
_refine_ls_wR_factor_gt          0.1850
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.5544(4) 0.7901(4) 0.4093(3) 0.0382(9) Uani 1 1 d . . . . .
C2 C 0.4645(4) 0.6792(4) 0.4264(3) 0.0420(9) Uani 1 1 d . . . . .
C3 C 0.4181(5) 0.6893(5) 0.5199(4) 0.0621(12) Uani 1 1 d . . . . .
H3 H 0.4427 0.7749 0.5853 0.075 Uiso 1 1 calc R U . . .
C4 C 0.3337(6) 0.5683(6) 0.5137(5) 0.0797(15) Uani 1 1 d . . . . .
H4 H 0.3017 0.5727 0.5762 0.096 Uiso 1 1 calc R U . . .
C5 C 0.2964(6) 0.4421(6) 0.4173(5) 0.0823(16) Uani 1 1 d . . . . .
H5 H 0.2389 0.3627 0.4154 0.099 Uiso 1 1 calc R U . . .
C6 C 0.3422(5) 0.4300(4) 0.3229(4) 0.0615(12) Uani 1 1 d . . . . .
H6 H 0.3168 0.3441 0.2578 0.074 Uiso 1 1 calc R U . . .
C7 C 0.4278(4) 0.5515(4) 0.3289(3) 0.0409(9) Uani 1 1 d . . . . .
C8 C 0.4910(4) 0.5683(3) 0.2410(3) 0.0347(8) Uani 1 1 d . . . . .
C9 C 0.5624(3) 0.7251(3) 0.2840(3) 0.0303(8) Uani 1 1 d . . . . .
C10 C 0.7137(3) 0.7735(3) 0.2833(3) 0.0340(9) Uani 1 1 d . . . . .
H10 H 0.7531 0.8749 0.3275 0.041 Uiso 1 1 calc R U . . .
C11 C 0.8156(3) 0.7284(4) 0.3453(3) 0.0347(9) Uani 1 1 d . . . . .
C12 C 0.8216(4) 0.5993(4) 0.2906(3) 0.0411(9) Uani 1 1 d . . . . .
H12 H 0.7624 0.5366 0.2115 0.049 Uiso 1 1 calc R U . . .
C13 C 0.9157(4) 0.5637(4) 0.3535(3) 0.0450(10) Uani 1 1 d . . . . .
C14 C 0.8379(5) 0.3353(5) 0.1924(4) 0.0774(15) Uani 1 1 d . . . . .
H14A H 0.7420 0.3132 0.1887 0.116 Uiso 1 1 calc R U . . .
H14B H 0.8588 0.2541 0.1744 0.116 Uiso 1 1 calc R U . . .
H14C H 0.8503 0.3671 0.1350 0.116 Uiso 1 1 calc R U . . .
C15 C 1.0054(4) 0.6591(5) 0.4712(4) 0.0554(11) Uani 1 1 d . . . . .
H15 H 1.0697 0.6364 0.5135 0.066 Uiso 1 1 calc R U . . .
C16 C 0.9993(4) 0.7850(5) 0.5246(4) 0.0587(12) Uani 1 1 d . . . . .
H16 H 1.0593 0.8482 0.6033 0.070 Uiso 1 1 calc R U . . .
C17 C 0.9047(4) 0.8195(4) 0.4627(3) 0.0468(10) Uani 1 1 d . . . . .
H17 H 0.9008 0.9058 0.5005 0.056 Uiso 1 1 calc R U . . .
C18 C 0.6882(4) 0.7351(3) 0.1498(3) 0.0349(9) Uani 1 1 d . . . . .
H18 H 0.6892 0.6434 0.1070 0.042 Uiso 1 1 calc R U . . .
C19 C 0.8020(4) 0.8429(5) 0.1423(3) 0.0488(10) Uani 1 1 d . . . . .
C20 C 1.0207(6) 0.8943(6) 0.1108(6) 0.111(2) Uani 1 1 d . . . . .
H20A H 0.9878 0.9445 0.0724 0.134 Uiso 1 1 calc R U . . .
H20B H 1.0638 0.8414 0.0626 0.134 Uiso 1 1 calc R U . . .
C21 C 1.1269(8) 0.9940(8) 0.2343(7) 0.148(3) Uani 1 1 d . . . . .
H21A H 1.0891 1.0565 0.2772 0.222 Uiso 1 1 calc R U . . .
H21B H 1.2114 1.0455 0.2287 0.222 Uiso 1 1 calc R U . . .
H21C H 1.1486 0.9439 0.2762 0.222 Uiso 1 1 calc R U . . .
C22 C 0.4836(3) 0.7625(3) 0.1891(3) 0.0300(8) Uani 1 1 d . . . . .
C23 C 0.3254(4) 0.6689(4) 0.1325(4) 0.0399(9) Uani 1 1 d . . . . .
C24 C 0.1193(5) 0.6187(6) 0.1791(5) 0.0994(19) Uani 1 1 d . . . . .
H24A H 0.0621 0.6209 0.1115 0.149 Uiso 1 1 calc R U . . .
H24B H 0.0883 0.6519 0.2452 0.149 Uiso 1 1 calc R U . . .
H24C H 0.1107 0.5254 0.1577 0.149 Uiso 1 1 calc R U . . .
C25 C 0.5060(4) 0.9172(3) 0.2470(3) 0.0395(9) Uani 1 1 d . . . . .
H25A H 0.4704 0.9378 0.3122 0.047 Uiso 1 1 calc R U . . .
H25B H 0.6061 0.9744 0.2803 0.047 Uiso 1 1 calc R U . . .
C26 C 0.4322(4) 0.9505(4) 0.1571(3) 0.0395(9) Uani 1 1 d . . . . .
C27 C 0.4320(6) 1.1265(5) 0.1017(4) 0.0747(14) Uani 1 1 d . . . . .
H27A H 0.4281 1.0717 0.0223 0.112 Uiso 1 1 calc R U . . .
H27B H 0.4866 1.2223 0.1287 0.112 Uiso 1 1 calc R U . . .
H27C H 0.3381 1.1148 0.1005 0.112 Uiso 1 1 calc R U . . .
N1 N 0.5489(3) 0.7335(3) 0.1002(2) 0.0366(7) Uani 1 1 d . . . . .
H1 H 0.5108 0.7173 0.0276 0.044 Uiso 1 1 calc R U . . .
O1 O 0.6151(3) 0.9117(3) 0.4830(2) 0.0573(8) Uani 1 1 d . . . . .
O2 O 0.4881(3) 0.4771(2) 0.1517(2) 0.0477(7) Uani 1 1 d . . . . .
O3 O 0.9299(3) 0.4403(3) 0.3092(3) 0.0692(9) Uani 1 1 d . . . . .
O4 O 0.8058(3) 0.9559(3) 0.1613(3) 0.0832(11) Uani 1 1 d . . . . .
O5 O 0.9010(4) 0.8001(3) 0.1187(3) 0.0897(11) Uani 1 1 d . . . . .
O6 O 0.2676(3) 0.5732(3) 0.0337(3) 0.0574(8) Uani 1 1 d . . . . .
O7 O 0.2654(3) 0.7062(3) 0.2138(2) 0.0588(8) Uani 1 1 d . . . . .
O8 O 0.3251(3) 0.8718(3) 0.0717(3) 0.0618(8) Uani 1 1 d . . . . .
O9 O 0.4974(3) 1.0823(2) 0.1828(2) 0.0553(8) 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
C1 O1 1.214(4) . ?
C1 C2 1.483(5) . ?
C1 C9 1.533(5) . ?
C2 C3 1.377(5) . ?
C2 C7 1.388(5) . ?
C3 C4 1.384(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.484(5) . ?
C8 O2 1.207(4) . ?
C8 C9 1.544(4) . ?
C9 C10 1.546(5) . ?
C9 C22 1.587(5) . ?
C10 C11 1.516(5) . ?
C10 C18 1.548(4) . ?
C10 H10 0.9800 . ?
C11 C17 1.380(5) . ?
C11 C12 1.390(5) . ?
C12 C13 1.388(5) . ?
C12 H12 0.9300 . ?
C13 O3 1.361(5) . ?
C13 C15 1.392(5) . ?
C14 O3 1.414(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.356(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N1 1.461(4) . ?
C18 C19 1.516(5) . ?
C18 H18 0.9800 . ?
C19 O4 1.199(5) . ?
C19 O5 1.312(5) . ?
C20 O5 1.470(6) . ?
C20 C21 1.495(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N1 1.443(4) . ?
C22 C23 1.538(5) . ?
C22 C25 1.548(4) . ?
C23 O6 1.193(4) . ?
C23 O7 1.334(4) . ?
C24 O7 1.448(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.482(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 O8 1.203(4) . ?
C26 O9 1.338(4) . ?
C27 O9 1.449(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N1 H1 0.8600 . ?

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
O1 C1 C2 126.0(3) . . ?
O1 C1 C9 125.3(3) . . ?
C2 C1 C9 108.6(3) . . ?
C3 C2 C7 121.1(4) . . ?
C3 C2 C1 129.5(4) . . ?
C7 C2 C1 109.4(3) . . ?
C2 C3 C4 118.0(4) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C7 117.5(4) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
C2 C7 C6 120.7(3) . . ?
C2 C7 C8 110.7(3) . . ?
C6 C7 C8 128.7(4) . . ?
O2 C8 C7 126.8(3) . . ?
O2 C8 C9 125.6(3) . . ?
C7 C8 C9 107.5(3) . . ?
C1 C9 C8 102.8(3) . . ?
C1 C9 C10 113.7(3) . . ?
C8 C9 C10 114.6(3) . . ?
C1 C9 C22 116.1(3) . . ?
C8 C9 C22 109.3(2) . . ?
C10 C9 C22 100.7(2) . . ?
C11 C10 C9 116.4(3) . . ?
C11 C10 C18 118.2(3) . . ?
C9 C10 C18 103.0(3) . . ?
C11 C10 H10 106.1 . . ?
C9 C10 H10 106.1 . . ?
C18 C10 H10 106.1 . . ?
C17 C11 C12 118.7(3) . . ?
C17 C11 C10 118.0(3) . . ?
C12 C11 C10 123.3(3) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
O3 C13 C12 125.1(4) . . ?
O3 C13 C15 115.4(4) . . ?
C12 C13 C15 119.5(4) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 120.3(4) . . ?
C16 C15 H15 119.9 . . ?
C13 C15 H15 119.9 . . ?
C15 C16 C17 120.2(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C11 121.1(4) . . ?
C16 C17 H17 119.5 . . ?
C11 C17 H17 119.5 . . ?
N1 C18 C19 111.2(3) . . ?
N1 C18 C10 105.9(3) . . ?
C19 C18 C10 109.4(3) . . ?
N1 C18 H18 110.1 . . ?
C19 C18 H18 110.1 . . ?
C10 C18 H18 110.1 . . ?
O4 C19 O5 123.7(4) . . ?
O4 C19 C18 124.7(4) . . ?
O5 C19 C18 111.5(4) . . ?
O5 C20 C21 109.4(5) . . ?
O5 C20 H20A 109.8 . . ?
C21 C20 H20A 109.8 . . ?
O5 C20 H20B 109.8 . . ?
C21 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 C23 110.6(3) . . ?
N1 C22 C25 110.1(3) . . ?
C23 C22 C25 110.7(3) . . ?
N1 C22 C9 103.9(2) . . ?
C23 C22 C9 109.7(3) . . ?
C25 C22 C9 111.6(2) . . ?
O6 C23 O7 125.4(4) . . ?
O6 C23 C22 125.1(4) . . ?
O7 C23 C22 109.3(3) . . ?
O7 C24 H24A 109.5 . . ?
O7 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O7 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C22 110.9(3) . . ?
C26 C25 H25A 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
O8 C26 O9 122.5(3) . . ?
O8 C26 C25 125.6(3) . . ?
O9 C26 C25 111.9(3) . . ?
O9 C27 H27A 109.5 . . ?
O9 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O9 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 N1 C18 111.2(2) . . ?
C22 N1 H1 124.4 . . ?
C18 N1 H1 124.4 . . ?
C13 O3 C14 118.9(3) . . ?
C19 O5 C20 118.1(4) . . ?
C23 O7 C24 116.4(3) . . ?
C26 O9 C27 116.3(3) . . ?

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
N1 H1 O2 0.86 2.52 3.075(4) 122.9 2_665

_refine_diff_density_max         0.506
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.064

