# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_ic17907
_database_code_depnum_ccdc_archive 'CCDC 1570179'
_audit_update_record             
;
2017-08-22 deposited with the CCDC.
2017-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H28 N2 O7'
_chemical_formula_weight         396.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(3)2(1)2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   8.2526(2)
_cell_length_b                   8.2526(2)
_cell_length_c                   60.866(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4145.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5167
_cell_measurement_theta_min      4.3220
_cell_measurement_theta_max      73.6340

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72594
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.2496
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14251
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -72
_diffrn_reflns_limit_l_max       72
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         67.98
_reflns_number_total             3755
_reflns_number_gt                3378
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1114P)²+4.3949P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_number_reflns         3755
_refine_ls_number_parameters     253
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0750
_refine_ls_wR_factor_ref         0.2107
_refine_ls_wR_factor_gt          0.2042
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6720(4) 0.0464(3) 0.18050(4) 0.0415(7) Uani 1 1 d . . .
O2 O 0.3948(4) 0.4757(4) 0.20120(4) 0.0423(7) Uani 1 1 d . . .
O3 O 0.8220(4) 0.5337(5) 0.21104(5) 0.0574(9) Uani 1 1 d . . .
O4 O 0.7174(5) 0.6372(7) 0.24257(5) 0.0850(16) Uani 1 1 d . . .
O5 O 0.7542(4) 0.5273(3) 0.10365(4) 0.0358(6) Uani 1 1 d . . .
O6 O 0.7392(4) 0.6705(4) 0.13531(5) 0.0448(7) Uani 1 1 d . . .
O7 O 0.7973(4) 0.1965(4) 0.10939(4) 0.0398(7) Uani 1 1 d . . .
N1 N 0.6316(4) 0.1481(4) 0.19844(5) 0.0388(8) Uani 1 1 d . . .
N2 N 0.7930(4) 0.4025(4) 0.13613(5) 0.0352(7) Uani 1 1 d . . .
C1 C 0.7986(5) 0.3957(5) 0.16041(6) 0.0371(9) Uani 1 1 d . . .
H1A H 0.8258 0.5002 0.1679 0.045 Uiso 1 1 calc R . .
C2 C 0.6357(4) 0.3168(5) 0.16748(6) 0.0294(8) Uani 1 1 d . . .
H2A H 0.5399 0.3681 0.1602 0.035 Uiso 1 1 calc R . .
C3 C 0.6620(5) 0.1394(5) 0.16013(6) 0.0339(9) Uani 1 1 d . . .
H3A H 0.5741 0.0998 0.1502 0.041 Uiso 1 1 calc R . .
C4 C 0.8294(5) 0.1411(5) 0.14883(6) 0.0393(9) Uani 1 1 d . . .
H4A H 0.8812 0.0329 0.1465 0.047 Uiso 1 1 calc R . .
C5 C 0.9213(5) 0.2584(6) 0.16371(7) 0.0450(11) Uani 1 1 d . . .
H5A H 1.0307 0.2854 0.1581 0.054 Uiso 1 1 calc R . .
H5B H 0.9277 0.2209 0.1791 0.054 Uiso 1 1 calc R . .
C6 C 0.6114(5) 0.2935(5) 0.19179(6) 0.0330(8) Uani 1 1 d . . .
C7 C 0.5527(5) 0.4212(5) 0.20745(6) 0.0372(9) Uani 1 1 d . . .
H7A H 0.5490 0.3760 0.2227 0.045 Uiso 1 1 calc R . .
C8 C 0.6572(6) 0.5731(6) 0.20713(7) 0.0460(11) Uani 1 1 d . . .
H8A H 0.6458 0.6299 0.1927 0.055 Uiso 1 1 calc R . .
C9 C 0.6116(9) 0.6876(7) 0.22596(8) 0.0710(17) Uani 1 1 d . . .
H9A H 0.6305 0.8022 0.2219 0.085 Uiso 1 1 calc R . .
H9B H 0.4970 0.6735 0.2304 0.085 Uiso 1 1 calc R . .
C10 C 0.8645(7) 0.5909(14) 0.23220(8) 0.114(3) Uani 1 1 d U . .
C11 C 0.9265(10) 0.4326(17) 0.24436(11) 0.162(4) Uani 1 1 d U . .
H11A H 0.8385 0.3530 0.2451 0.243 Uiso 1 1 calc R . .
H11B H 0.9614 0.4604 0.2593 0.243 Uiso 1 1 calc R . .
H11C H 1.0180 0.3864 0.2362 0.243 Uiso 1 1 calc R . .
C12 C 0.9851(12) 0.7154(16) 0.23106(14) 0.180(5) Uani 1 1 d U . .
H12A H 0.9412 0.8092 0.2232 0.270 Uiso 1 1 calc R . .
H12B H 1.0805 0.6743 0.2232 0.270 Uiso 1 1 calc R . .
H12C H 1.0162 0.7480 0.2460 0.270 Uiso 1 1 calc R . .
C13 C 0.8065(4) 0.2442(5) 0.12831(6) 0.0337(8) Uani 1 1 d . . .
C14 C 0.7586(4) 0.5469(5) 0.12521(6) 0.0319(8) Uani 1 1 d . . .
C15 C 0.7493(5) 0.6720(5) 0.08890(6) 0.0367(9) Uani 1 1 d . . .
C16 C 0.8971(6) 0.7766(6) 0.09359(7) 0.0461(11) Uani 1 1 d . . .
H16A H 0.8871 0.8247 0.1082 0.069 Uiso 1 1 calc R . .
H16B H 0.9044 0.8628 0.0826 0.069 Uiso 1 1 calc R . .
H16C H 0.9949 0.7095 0.0930 0.069 Uiso 1 1 calc R . .
C17 C 0.7608(7) 0.5955(6) 0.06630(7) 0.0496(11) Uani 1 1 d . . .
H17A H 0.6645 0.5289 0.0636 0.074 Uiso 1 1 calc R . .
H17B H 0.8579 0.5274 0.0655 0.074 Uiso 1 1 calc R . .
H17C H 0.7674 0.6809 0.0551 0.074 Uiso 1 1 calc R . .
C18 C 0.5943(6) 0.7640(7) 0.09186(9) 0.0562(13) Uani 1 1 d . . .
H18A H 0.5023 0.6928 0.0886 0.084 Uiso 1 1 calc R . .
H18B H 0.5927 0.8569 0.0818 0.084 Uiso 1 1 calc R . .
H18C H 0.5865 0.8025 0.1071 0.084 Uiso 1 1 calc R . .
C19 C 0.2764(5) 0.3523(6) 0.20113(7) 0.0473(11) Uani 1 1 d . . .
H19A H 0.1717 0.3982 0.1968 0.071 Uiso 1 1 calc R . .
H19B H 0.2675 0.3056 0.2159 0.071 Uiso 1 1 calc R . .
H19C H 0.3079 0.2676 0.1907 0.071 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.417(4) . ?
O1 C3 1.461(4) . ?
O2 C19 1.411(6) . ?
O2 C7 1.430(5) . ?
O3 C10 1.416(6) . ?
O3 C8 1.419(6) . ?
O4 C9 1.399(7) . ?
O4 C10 1.420(8) . ?
O5 C14 1.323(5) . ?
O5 C15 1.494(4) . ?
O6 C14 1.202(5) . ?
O7 C13 1.219(5) . ?
N1 C6 1.277(5) . ?
N2 C14 1.393(5) . ?
N2 C13 1.395(5) . ?
N2 C1 1.480(5) . ?
C1 C5 1.533(6) . ?
C1 C2 1.555(5) . ?
C2 C6 1.505(5) . ?
C2 C3 1.546(5) . ?
C3 C4 1.543(6) . ?
C4 C13 1.523(5) . ?
C4 C5 1.528(6) . ?
C6 C7 1.501(6) . ?
C7 C8 1.522(6) . ?
C8 C9 1.532(7) . ?
C10 C12 1.433(12) . ?
C10 C11 1.587(15) . ?
C15 C18 1.498(6) . ?
C15 C17 1.516(6) . ?
C15 C16 1.521(6) . ?

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 O1 C3 109.2(3) . . ?
C19 O2 C7 113.9(3) . . ?
C10 O3 C8 108.3(5) . . ?
C9 O4 C10 107.0(4) . . ?
C14 O5 C15 119.9(3) . . ?
C6 N1 O1 110.1(3) . . ?
C14 N2 C13 130.9(3) . . ?
C14 N2 C1 121.0(3) . . ?
C13 N2 C1 107.6(3) . . ?
N2 C1 C5 100.4(3) . . ?
N2 C1 C2 105.4(3) . . ?
C5 C1 C2 103.0(3) . . ?
C6 C2 C3 100.5(3) . . ?
C6 C2 C1 116.2(3) . . ?
C3 C2 C1 101.2(3) . . ?
O1 C3 C4 109.4(3) . . ?
O1 C3 C2 105.1(3) . . ?
C4 C3 C2 104.3(3) . . ?
C13 C4 C5 101.2(3) . . ?
C13 C4 C3 105.0(3) . . ?
C5 C4 C3 100.7(3) . . ?
C4 C5 C1 93.6(3) . . ?
N1 C6 C7 120.0(3) . . ?
N1 C6 C2 114.5(4) . . ?
C7 C6 C2 125.3(3) . . ?
O2 C7 C6 110.2(3) . . ?
O2 C7 C8 104.7(3) . . ?
C6 C7 C8 112.8(4) . . ?
O3 C8 C7 110.7(4) . . ?
O3 C8 C9 104.6(4) . . ?
C7 C8 C9 111.0(4) . . ?
O4 C9 C8 101.8(5) . . ?
O3 C10 O4 106.4(4) . . ?
O3 C10 C12 111.5(5) . . ?
O4 C10 C12 115.0(9) . . ?
O3 C10 C11 103.3(8) . . ?
O4 C10 C11 106.8(5) . . ?
C12 C10 C11 112.9(8) . . ?
O7 C13 N2 128.3(3) . . ?
O7 C13 C4 127.0(4) . . ?
N2 C13 C4 104.7(3) . . ?
O6 C14 O5 127.4(4) . . ?
O6 C14 N2 120.6(3) . . ?
O5 C14 N2 112.0(3) . . ?
O5 C15 C18 110.8(3) . . ?
O5 C15 C17 102.2(3) . . ?
C18 C15 C17 111.9(4) . . ?
O5 C15 C16 108.6(3) . . ?
C18 C15 C16 112.0(4) . . ?
C17 C15 C16 110.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        67.98
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.061
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_ic18367
_database_code_depnum_ccdc_archive 'CCDC 1570184'
_audit_update_record             
;
2017-08-22 deposited with the CCDC.
2017-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H32 N2 O7'
_chemical_formula_weight         472.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   6.0765(2)
_cell_length_b                   9.6451(4)
_cell_length_c                   11.0698(4)
_cell_angle_alpha                89.902(3)
_cell_angle_beta                 75.421(3)
_cell_angle_gamma                76.398(4)
_cell_volume                     609.14(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6783
_cell_measurement_theta_min      4.0990
_cell_measurement_theta_max      77.3320

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.2496
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9105
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.13
_diffrn_reflns_theta_max         67.97
_reflns_number_total             4153
_reflns_number_gt                4009
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0653P)²+0.0327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(13)
_refine_ls_number_reflns         4153
_refine_ls_number_parameters     307
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6080(2) 1.36657(13) 0.13750(13) 0.0309(3) Uani 1 1 d . . .
O2 O 0.4262(2) 0.99804(14) -0.04859(13) 0.0315(3) Uani 1 1 d . . .
O3 O 0.6838(2) 0.68890(14) 0.21727(11) 0.0265(3) Uani 1 1 d . . .
O4 O 1.0241(2) 0.62321(17) -0.10253(13) 0.0408(4) Uani 1 1 d . . .
O5 O 1.1292(2) 0.39562(14) -0.05043(12) 0.0334(3) Uani 1 1 d . . .
O6 O 1.0157(2) 1.02055(15) 0.28128(13) 0.0360(3) Uani 1 1 d . . .
O7 O 0.8620(2) 1.25957(14) 0.30602(12) 0.0326(3) Uani 1 1 d . . .
N1 N 0.8490(2) 1.13746(16) 0.13706(14) 0.0261(3) Uani 1 1 d . . .
N2 N 0.5018(3) 0.84852(17) -0.03451(15) 0.0297(3) Uani 1 1 d . . .
C1 C 0.6478(3) 1.1722(2) -0.01632(16) 0.0263(3) Uani 1 1 d . . .
H1A H 0.5938 1.2366 -0.0795 0.032 Uiso 1 1 calc R . .
C2 C 0.4842(3) 1.07781(19) 0.04495(16) 0.0251(3) Uani 1 1 d . . .
H2A H 0.3413 1.1336 0.1073 0.030 Uiso 1 1 calc R . .
C3 C 0.6395(3) 0.96386(18) 0.10619(15) 0.0230(3) Uani 1 1 d . . .
H3A H 0.5799 0.9693 0.1993 0.028 Uiso 1 1 calc R . .
C4 C 0.8800(3) 1.00336(18) 0.06343(16) 0.0254(4) Uani 1 1 d . . .
H4A H 1.0197 0.9257 0.0667 0.031 Uiso 1 1 calc R . .
C5 C 0.8801(3) 1.0606(2) -0.06545(17) 0.0297(4) Uani 1 1 d . . .
H5A H 0.8714 0.9884 -0.1264 0.036 Uiso 1 1 calc R . .
H5B H 1.0138 1.1035 -0.1003 0.036 Uiso 1 1 calc R . .
C6 C 0.6191(3) 0.82967(19) 0.04668(15) 0.0233(3) Uani 1 1 d . . .
C7 C 0.7174(3) 0.68279(19) 0.08578(15) 0.0247(3) Uani 1 1 d . . .
H7A H 0.6364 0.6128 0.0608 0.030 Uiso 1 1 calc R . .
C8 C 0.9823(3) 0.6320(2) 0.02965(16) 0.0271(4) Uani 1 1 d . . .
H8A H 1.0644 0.7006 0.0559 0.032 Uiso 1 1 calc R . .
C9 C 1.0856(3) 0.4804(2) 0.06259(16) 0.0278(4) Uani 1 1 d . . .
H9A H 1.2326 0.4753 0.0875 0.033 Uiso 1 1 calc R . .
H9B H 0.9729 0.4486 0.1315 0.033 Uiso 1 1 calc R . .
C10 C 1.1757(3) 0.4871(2) -0.14920(17) 0.0322(4) Uani 1 1 d . . .
C11 C 1.4284(3) 0.4982(2) -0.18353(19) 0.0370(4) Uani 1 1 d . . .
H11A H 1.4657 0.5332 -0.1098 0.056 Uiso 1 1 calc R . .
H11B H 1.4509 0.5648 -0.2499 0.056 Uiso 1 1 calc R . .
H11C H 1.5322 0.4038 -0.2130 0.056 Uiso 1 1 calc R . .
C12 C 1.1071(5) 0.4336(4) -0.2593(2) 0.0574(7) Uani 1 1 d . . .
H12A H 0.9434 0.4273 -0.2331 0.086 Uiso 1 1 calc R . .
H12B H 1.2083 0.3389 -0.2900 0.086 Uiso 1 1 calc R . .
H12C H 1.1251 0.5000 -0.3261 0.086 Uiso 1 1 calc R . .
C13 C 0.4453(3) 0.7056(2) 0.28439(16) 0.0284(4) Uani 1 1 d . . .
H13A H 0.4027 0.6127 0.2842 0.034 Uiso 1 1 calc R . .
H13B H 0.3424 0.7740 0.2433 0.034 Uiso 1 1 calc R . .
C14 C 0.4101(3) 0.7603(2) 0.41758(16) 0.0279(4) Uani 1 1 d . . .
C15 C 0.5714(3) 0.8209(2) 0.45264(18) 0.0339(4) Uani 1 1 d . . .
H15A H 0.7093 0.8290 0.3923 0.041 Uiso 1 1 calc R . .
C16 C 0.2072(3) 0.7512(2) 0.50639(19) 0.0360(4) Uani 1 1 d . . .
H16A H 0.0945 0.7111 0.4828 0.043 Uiso 1 1 calc R . .
C17 C 0.5316(4) 0.8702(3) 0.5766(2) 0.0407(5) Uani 1 1 d . . .
H17A H 0.6427 0.9116 0.6005 0.049 Uiso 1 1 calc R . .
C18 C 0.1688(4) 0.8006(3) 0.62973(19) 0.0435(5) Uani 1 1 d . . .
H18A H 0.0299 0.7941 0.6900 0.052 Uiso 1 1 calc R . .
C19 C 0.3307(4) 0.8588(3) 0.66495(18) 0.0432(5) Uani 1 1 d . . .
H19A H 0.3050 0.8912 0.7495 0.052 Uiso 1 1 calc R . .
C20 C 0.6934(3) 1.24616(19) 0.09385(16) 0.0253(3) Uani 1 1 d . . .
C21 C 0.9170(3) 1.13133(19) 0.24916(16) 0.0259(3) Uani 1 1 d . . .
C22 C 0.9299(3) 1.2804(2) 0.42360(17) 0.0322(4) Uani 1 1 d . . .
C23 C 0.8249(4) 1.1915(3) 0.5236(2) 0.0456(5) Uani 1 1 d . . .
H23A H 0.8992 1.0900 0.5007 0.068 Uiso 1 1 calc R . .
H23B H 0.6562 1.2088 0.5317 0.068 Uiso 1 1 calc R . .
H23C H 0.8512 1.2176 0.6034 0.068 Uiso 1 1 calc R . .
C24 C 1.1956(4) 1.2472(3) 0.3954(2) 0.0502(6) Uani 1 1 d . . .
H24A H 1.2604 1.1445 0.3750 0.075 Uiso 1 1 calc R . .
H24B H 1.2412 1.2755 0.4687 0.075 Uiso 1 1 calc R . .
H24C H 1.2564 1.3002 0.3241 0.075 Uiso 1 1 calc R . .
C25 C 0.8194(5) 1.4388(3) 0.4562(2) 0.0470(5) Uani 1 1 d . . .
H25A H 0.6485 1.4560 0.4745 0.070 Uiso 1 1 calc R . .
H25B H 0.8759 1.4937 0.3854 0.070 Uiso 1 1 calc R . .
H25C H 0.8627 1.4688 0.5298 0.070 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.202(2) . ?
O2 N2 1.428(2) . ?
O2 C2 1.450(2) . ?
O3 C7 1.4174(19) . ?
O3 C13 1.424(2) . ?
O4 C8 1.420(2) . ?
O4 C10 1.426(2) . ?
O5 C10 1.418(2) . ?
O5 C9 1.428(2) . ?
O6 C21 1.197(2) . ?
O7 C21 1.319(2) . ?
O7 C22 1.488(2) . ?
N1 C21 1.400(2) . ?
N1 C20 1.408(2) . ?
N1 C4 1.478(2) . ?
N2 C6 1.269(2) . ?
C1 C20 1.529(2) . ?
C1 C5 1.533(2) . ?
C1 C2 1.537(2) . ?
C2 C3 1.546(2) . ?
C3 C6 1.498(2) . ?
C3 C4 1.555(2) . ?
C4 C5 1.529(2) . ?
C6 C7 1.510(2) . ?
C7 C8 1.531(2) . ?
C8 C9 1.532(2) . ?
C10 C12 1.511(3) . ?
C10 C11 1.516(3) . ?
C13 C14 1.513(2) . ?
C14 C15 1.384(3) . ?
C14 C16 1.391(3) . ?
C15 C17 1.396(3) . ?
C16 C18 1.391(3) . ?
C17 C19 1.385(3) . ?
C18 C19 1.375(4) . ?
C22 C23 1.506(3) . ?
C22 C24 1.519(3) . ?
C22 C25 1.521(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O2 C2 109.52(12) . . ?
C7 O3 C13 113.07(12) . . ?
C8 O4 C10 108.31(14) . . ?
C10 O5 C9 106.05(14) . . ?
C21 O7 C22 120.39(14) . . ?
C21 N1 C20 130.27(15) . . ?
C21 N1 C4 119.35(14) . . ?
C20 N1 C4 107.88(14) . . ?
C6 N2 O2 109.27(14) . . ?
C20 C1 C5 101.85(14) . . ?
C20 C1 C2 104.35(13) . . ?
C5 C1 C2 101.39(14) . . ?
O2 C2 C1 111.15(14) . . ?
O2 C2 C3 104.83(13) . . ?
C1 C2 C3 103.78(13) . . ?
C6 C3 C2 100.58(13) . . ?
C6 C3 C4 116.68(13) . . ?
C2 C3 C4 101.63(13) . . ?
N1 C4 C5 100.41(14) . . ?
N1 C4 C3 104.65(13) . . ?
C5 C4 C3 103.39(13) . . ?
C4 C5 C1 93.40(13) . . ?
N2 C6 C3 115.06(15) . . ?
N2 C6 C7 122.16(16) . . ?
C3 C6 C7 122.68(14) . . ?
O3 C7 C6 108.91(13) . . ?
O3 C7 C8 105.95(12) . . ?
C6 C7 C8 111.95(14) . . ?
O4 C8 C7 107.88(13) . . ?
O4 C8 C9 104.74(14) . . ?
C7 C8 C9 113.21(14) . . ?
O5 C9 C8 103.85(13) . . ?
O5 C10 O4 104.84(14) . . ?
O5 C10 C12 108.11(19) . . ?
O4 C10 C12 109.36(18) . . ?
O5 C10 C11 112.40(16) . . ?
O4 C10 C11 109.79(17) . . ?
C12 C10 C11 112.06(17) . . ?
O3 C13 C14 109.70(14) . . ?
C15 C14 C16 119.41(17) . . ?
C15 C14 C13 121.94(16) . . ?
C16 C14 C13 118.64(17) . . ?
C14 C15 C17 120.00(18) . . ?
C14 C16 C18 120.2(2) . . ?
C19 C17 C15 120.3(2) . . ?
C19 C18 C16 120.4(2) . . ?
C18 C19 C17 119.73(19) . . ?
O1 C20 N1 127.87(16) . . ?
O1 C20 C1 128.33(16) . . ?
N1 C20 C1 103.71(14) . . ?
O6 C21 O7 128.14(16) . . ?
O6 C21 N1 120.96(17) . . ?
O7 C21 N1 110.89(15) . . ?
O7 C22 C23 110.79(16) . . ?
O7 C22 C24 108.99(15) . . ?
C23 C22 C24 112.59(19) . . ?
O7 C22 C25 101.15(15) . . ?
C23 C22 C25 110.97(18) . . ?
C24 C22 C25 111.8(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.97
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_ic18393
_database_code_depnum_ccdc_archive 'CCDC 1570191'
_audit_update_record             
;
2017-08-22 deposited with the CCDC.
2017-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H44 N2 O10'
_chemical_formula_weight         592.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.3732(4)
_cell_length_b                   16.8818(4)
_cell_length_c                   35.8766(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6282.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4839
_cell_measurement_theta_min      2.9020
_cell_measurement_theta_max      76.8530

_exptl_crystal_description       column
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2544
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.2496
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20260
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         68.00
_reflns_number_total             10886
_reflns_number_gt                6990
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+4.8000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_number_reflns         10886
_refine_ls_number_parameters     757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0798
_refine_ls_wR_factor_ref         0.2541
_refine_ls_wR_factor_gt          0.2120
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4408(5) 0.2889(3) 0.48400(15) 0.0646(15) Uani 1 1 d . . .
O2 O 0.6710(4) 0.1140(2) 0.53215(11) 0.0394(10) Uani 1 1 d . . .
O3 O 0.4363(4) 0.2217(2) 0.64287(11) 0.0371(9) Uani 1 1 d . . .
O4 O 0.2111(4) 0.1050(2) 0.65442(11) 0.0429(10) Uani 1 1 d . . .
O5 O 0.3106(5) 0.0707(3) 0.70689(13) 0.0642(14) Uani 1 1 d . . .
O6 O 0.7507(4) 0.2233(2) 0.65160(11) 0.0398(10) Uani 1 1 d . . .
O7 O 0.6764(4) 0.3456(2) 0.66775(10) 0.0383(10) Uani 1 1 d . . .
O8 O 0.5564(5) 0.0306(3) 0.49638(14) 0.0563(13) Uani 1 1 d . . .
O9 O 0.5904(4) -0.0258(2) 0.59699(12) 0.0437(11) Uani 1 1 d . . .
O1' O 0.6218(4) 0.3307(2) 0.45754(11) 0.0418(10) Uani 1 1 d . . .
N1 N 0.6613(5) 0.3076(3) 0.60909(12) 0.0322(11) Uani 1 1 d . . .
H1B H 0.6306 0.3556 0.6057 0.039 Uiso 1 1 calc R . .
N2 N 0.6118(5) 0.1030(3) 0.61523(14) 0.0358(11) Uani 1 1 d . . .
H2B H 0.6549 0.1353 0.6299 0.043 Uiso 1 1 calc R . .
C1 C 0.6427(6) 0.2465(3) 0.50930(16) 0.0341(13) Uani 1 1 d . . .
H1A H 0.7200 0.2261 0.4957 0.041 Uiso 1 1 calc R . .
C2 C 0.5735(6) 0.1769(3) 0.52889(16) 0.0342(13) Uani 1 1 d . . .
H2A H 0.4946 0.1592 0.5152 0.041 Uiso 1 1 calc R . .
C3 C 0.5440(6) 0.2046(3) 0.56831(15) 0.0311(12) Uani 1 1 d . . .
H3A H 0.4700 0.2425 0.5667 0.037 Uiso 1 1 calc R . .
C4 C 0.6669(6) 0.2541(3) 0.57723(15) 0.0313(13) Uani 1 1 d . . .
H4A H 0.7414 0.2172 0.5805 0.038 Uiso 1 1 calc R . .
C5 C 0.6871(6) 0.3022(3) 0.54150(15) 0.0358(13) Uani 1 1 d . . .
H5A H 0.7790 0.3167 0.5385 0.043 Uiso 1 1 calc R . .
H5B H 0.6348 0.3512 0.5419 0.043 Uiso 1 1 calc R . .
C6 C 0.5019(6) 0.1356(3) 0.59437(16) 0.0329(13) Uani 1 1 d . . .
H6A H 0.4696 0.0922 0.5779 0.039 Uiso 1 1 calc R . .
C7 C 0.3909(6) 0.1584(3) 0.61982(15) 0.0335(13) Uani 1 1 d . . .
H7A H 0.3186 0.1787 0.6041 0.040 Uiso 1 1 calc R . .
C8 C 0.3411(6) 0.0873(3) 0.64267(17) 0.0414(14) Uani 1 1 d . . .
H8A H 0.3401 0.0391 0.6265 0.050 Uiso 1 1 calc R . .
C9 C 0.4085(7) 0.0679(4) 0.67907(18) 0.0524(18) Uani 1 1 d . . .
H9A H 0.4479 0.0145 0.6780 0.063 Uiso 1 1 calc R . .
H9B H 0.4769 0.1072 0.6844 0.063 Uiso 1 1 calc R . .
C10 C 0.1916(7) 0.0650(4) 0.68846(17) 0.0473(16) Uani 1 1 d . . .
C11 C 0.1470(8) -0.0190(4) 0.68201(19) 0.058(2) Uani 1 1 d . . .
H11A H 0.2125 -0.0478 0.6678 0.087 Uiso 1 1 calc R . .
H11B H 0.0658 -0.0185 0.6680 0.087 Uiso 1 1 calc R . .
H11C H 0.1336 -0.0452 0.7061 0.087 Uiso 1 1 calc R . .
C12 C 0.0932(8) 0.1110(5) 0.7113(2) 0.073(2) Uani 1 1 d . . .
H12A H 0.1236 0.1654 0.7149 0.109 Uiso 1 1 calc R . .
H12B H 0.0822 0.0854 0.7356 0.109 Uiso 1 1 calc R . .
H12C H 0.0105 0.1117 0.6981 0.109 Uiso 1 1 calc R . .
C13 C 0.3384(6) 0.2718(3) 0.65967(16) 0.0400(14) Uani 1 1 d . . .
H13A H 0.3814 0.3153 0.6734 0.048 Uiso 1 1 calc R . .
H13B H 0.2891 0.2401 0.6780 0.048 Uiso 1 1 calc R . .
C14 C 0.2451(6) 0.3073(3) 0.63182(16) 0.0372(14) Uani 1 1 d . . .
C15 C 0.2898(7) 0.3615(3) 0.60526(18) 0.0424(15) Uani 1 1 d . . .
H15A H 0.3788 0.3747 0.6047 0.051 Uiso 1 1 calc R . .
C16 C 0.1158(6) 0.2877(4) 0.63247(19) 0.0447(16) Uani 1 1 d . . .
H16A H 0.0840 0.2508 0.6502 0.054 Uiso 1 1 calc R . .
C17 C 0.2083(7) 0.3957(4) 0.58014(18) 0.0460(16) Uani 1 1 d . . .
H17A H 0.2402 0.4327 0.5624 0.055 Uiso 1 1 calc R . .
C18 C 0.0333(7) 0.3224(4) 0.6070(2) 0.0509(18) Uani 1 1 d . . .
H18A H -0.0558 0.3092 0.6075 0.061 Uiso 1 1 calc R . .
C19 C 0.0777(7) 0.3760(4) 0.5807(2) 0.0513(17) Uani 1 1 d . . .
H19A H 0.0199 0.3991 0.5633 0.062 Uiso 1 1 calc R . .
C20 C 0.5560(6) 0.2895(4) 0.48252(15) 0.0381(14) Uani 1 1 d . . .
C21 C 0.7006(6) 0.2870(3) 0.64314(15) 0.0333(13) Uani 1 1 d . . .
C22 C 0.7108(6) 0.3379(4) 0.70715(16) 0.0436(15) Uani 1 1 d . . .
C23 C 0.8567(7) 0.3300(5) 0.71099(19) 0.0592(19) Uani 1 1 d . . .
H23A H 0.8846 0.2794 0.7003 0.089 Uiso 1 1 calc R . .
H23B H 0.8804 0.3320 0.7374 0.089 Uiso 1 1 calc R . .
H23C H 0.8989 0.3736 0.6977 0.089 Uiso 1 1 calc R . .
C24 C 0.6645(8) 0.4162(4) 0.72318(18) 0.061(2) Uani 1 1 d . . .
H24A H 0.5706 0.4197 0.7207 0.091 Uiso 1 1 calc R . .
H24B H 0.7049 0.4600 0.7096 0.091 Uiso 1 1 calc R . .
H24C H 0.6882 0.4193 0.7496 0.091 Uiso 1 1 calc R . .
C25 C 0.6388(7) 0.2698(4) 0.72460(18) 0.0558(19) Uani 1 1 d . . .
H25A H 0.5459 0.2779 0.7214 0.084 Uiso 1 1 calc R . .
H25B H 0.6593 0.2671 0.7512 0.084 Uiso 1 1 calc R . .
H25C H 0.6644 0.2202 0.7125 0.084 Uiso 1 1 calc R . .
C26 C 0.5454(7) 0.3783(3) 0.43197(17) 0.0451(16) Uani 1 1 d . . .
H26A H 0.6028 0.4062 0.4147 0.068 Uiso 1 1 calc R . .
H26B H 0.4948 0.4170 0.4461 0.068 Uiso 1 1 calc R . .
H26C H 0.4872 0.3438 0.4178 0.068 Uiso 1 1 calc R . .
C27 C 0.6534(6) 0.0473(3) 0.51282(16) 0.0346(13) Uani 1 1 d . . .
C28 C 0.7738(6) -0.0019(3) 0.51355(18) 0.0444(15) Uani 1 1 d . . .
H28A H 0.7599 -0.0506 0.4992 0.067 Uiso 1 1 calc R . .
H28B H 0.7951 -0.0155 0.5394 0.067 Uiso 1 1 calc R . .
H28C H 0.8450 0.0281 0.5025 0.067 Uiso 1 1 calc R . .
C29 C 0.6509(7) 0.0272(3) 0.61344(17) 0.0397(15) Uani 1 1 d . . .
C30 C 0.7775(6) 0.0102(3) 0.6333(2) 0.0492(17) Uani 1 1 d . . .
H30A H 0.7990 -0.0461 0.6305 0.074 Uiso 1 1 calc R . .
H30B H 0.7689 0.0230 0.6598 0.074 Uiso 1 1 calc R . .
H30C H 0.8461 0.0425 0.6223 0.074 Uiso 1 1 calc R . .
O11 O 0.4489(5) 0.7886(3) 0.47943(14) 0.0599(14) Uani 1 1 d . . .
O12 O 0.6777(4) 0.6157(2) 0.52691(10) 0.0350(9) Uani 1 1 d . . .
O13 O 0.4550(4) 0.7101(2) 0.64247(11) 0.0357(9) Uani 1 1 d . . .
O14 O 0.2402(4) 0.5970(2) 0.65689(11) 0.0415(10) Uani 1 1 d . . .
O15 O 0.3429(4) 0.4980(3) 0.68929(13) 0.0521(12) Uani 1 1 d . . .
O16 O 0.7766(4) 0.7148(2) 0.64551(10) 0.0391(10) Uani 1 1 d . . .
O17 O 0.6925(4) 0.8291(2) 0.66822(11) 0.0415(10) Uani 1 1 d . . .
O18 O 0.5529(5) 0.5344(3) 0.49308(15) 0.0579(13) Uani 1 1 d . . .
O19 O 0.6035(4) 0.4725(2) 0.59025(12) 0.0415(10) Uani 1 1 d . . .
O11' O 0.6315(4) 0.8379(2) 0.45615(11) 0.0404(10) Uani 1 1 d . . .
N3 N 0.6729(5) 0.8032(3) 0.60820(12) 0.0327(11) Uani 1 1 d . . .
H3B H 0.6407 0.8513 0.6069 0.039 Uiso 1 1 calc R . .
N4 N 0.6293(5) 0.5992(2) 0.60944(13) 0.0327(11) Uani 1 1 d . . .
H4B H 0.6747 0.6310 0.6237 0.039 Uiso 1 1 calc R . .
C31 C 0.6507(6) 0.7507(3) 0.50698(15) 0.0321(13) Uani 1 1 d . . .
H31A H 0.7296 0.7318 0.4937 0.039 Uiso 1 1 calc R . .
C32 C 0.5818(6) 0.6796(3) 0.52552(16) 0.0339(13) Uani 1 1 d . . .
H32A H 0.5019 0.6636 0.5118 0.041 Uiso 1 1 calc R . .
C33 C 0.5539(6) 0.7048(3) 0.56566(15) 0.0296(12) Uani 1 1 d . . .
H33A H 0.4786 0.7418 0.5651 0.036 Uiso 1 1 calc R . .
C34 C 0.6757(6) 0.7544(3) 0.57482(14) 0.0308(12) Uani 1 1 d . . .
H34A H 0.7514 0.7179 0.5764 0.037 Uiso 1 1 calc R . .
C35 C 0.6906(6) 0.8061(3) 0.53992(14) 0.0338(13) Uani 1 1 d . . .
H35A H 0.7808 0.8242 0.5370 0.041 Uiso 1 1 calc R . .
H35B H 0.6334 0.8530 0.5412 0.041 Uiso 1 1 calc R . .
C36 C 0.5156(6) 0.6323(3) 0.59035(15) 0.0305(12) Uani 1 1 d . . .
H36A H 0.4827 0.5903 0.5731 0.037 Uiso 1 1 calc R . .
C37 C 0.4064(6) 0.6515(3) 0.61754(15) 0.0298(12) Uani 1 1 d . . .
H37A H 0.3335 0.6752 0.6031 0.036 Uiso 1 1 calc R . .
C38 C 0.3566(6) 0.5769(3) 0.63739(16) 0.0375(14) Uani 1 1 d . . .
H38A H 0.3358 0.5360 0.6181 0.045 Uiso 1 1 calc R . .
C39 C 0.4367(7) 0.5388(4) 0.66746(18) 0.0462(16) Uani 1 1 d . . .
H39A H 0.5004 0.5016 0.6567 0.055 Uiso 1 1 calc R . .
H39B H 0.4825 0.5792 0.6825 0.055 Uiso 1 1 calc R . .
C40 C 0.2282(6) 0.5459(3) 0.68840(17) 0.0421(15) Uani 1 1 d . . .
C41 C 0.1155(7) 0.4908(4) 0.6833(2) 0.0551(18) Uani 1 1 d . . .
H41A H 0.1270 0.4601 0.6604 0.083 Uiso 1 1 calc R . .
H41B H 0.0358 0.5217 0.6817 0.083 Uiso 1 1 calc R . .
H41C H 0.1104 0.4545 0.7046 0.083 Uiso 1 1 calc R . .
C42 C 0.2193(9) 0.5947(4) 0.72298(19) 0.067(2) Uani 1 1 d . . .
H42A H 0.2956 0.6287 0.7249 0.100 Uiso 1 1 calc R . .
H42B H 0.2148 0.5598 0.7448 0.100 Uiso 1 1 calc R . .
H42C H 0.1417 0.6278 0.7219 0.100 Uiso 1 1 calc R . .
C43 C 0.3608(6) 0.7624(3) 0.65968(16) 0.0395(15) Uani 1 1 d . . .
H43A H 0.4074 0.8047 0.6733 0.047 Uiso 1 1 calc R . .
H43B H 0.3109 0.7317 0.6782 0.047 Uiso 1 1 calc R . .
C44 C 0.2677(6) 0.8006(3) 0.63287(16) 0.0374(14) Uani 1 1 d . . .
C45 C 0.3087(7) 0.8580(3) 0.60799(17) 0.0443(15) Uani 1 1 d . . .
H45A H 0.3974 0.8719 0.6073 0.053 Uiso 1 1 calc R . .
C46 C 0.1390(6) 0.7793(4) 0.63343(19) 0.0442(15) Uani 1 1 d . . .
H46A H 0.1093 0.7396 0.6501 0.053 Uiso 1 1 calc R . .
C47 C 0.2243(7) 0.8959(4) 0.58409(18) 0.0473(16) Uani 1 1 d . . .
H47A H 0.2539 0.9357 0.5675 0.057 Uiso 1 1 calc R . .
C48 C 0.0535(7) 0.8168(4) 0.6093(2) 0.0522(18) Uani 1 1 d . . .
H48A H -0.0351 0.8027 0.6096 0.063 Uiso 1 1 calc R . .
C49 C 0.0961(7) 0.8744(4) 0.5850(2) 0.0530(18) Uani 1 1 d . . .
H49A H 0.0366 0.8995 0.5687 0.064 Uiso 1 1 calc R . .
C50 C 0.5637(6) 0.7932(3) 0.47991(15) 0.0364(14) Uani 1 1 d . . .
C51 C 0.7178(6) 0.7770(3) 0.64084(16) 0.0355(13) Uani 1 1 d . . .
C52 C 0.7305(7) 0.8111(4) 0.70715(17) 0.0489(17) Uani 1 1 d . . .
C53 C 0.8755(7) 0.8101(6) 0.7105(2) 0.074(3) Uani 1 1 d . . .
H53A H 0.9099 0.7645 0.6968 0.110 Uiso 1 1 calc R . .
H53B H 0.8998 0.8060 0.7368 0.110 Uiso 1 1 calc R . .
H53C H 0.9108 0.8591 0.6999 0.110 Uiso 1 1 calc R . .
C54 C 0.6682(7) 0.7343(4) 0.71994(17) 0.0523(18) Uani 1 1 d . . .
H54A H 0.5744 0.7384 0.7173 0.078 Uiso 1 1 calc R . .
H54B H 0.6899 0.7247 0.7461 0.078 Uiso 1 1 calc R . .
H54C H 0.7001 0.6904 0.7046 0.078 Uiso 1 1 calc R . .
C55 C 0.6721(9) 0.8819(4) 0.72774(19) 0.070(2) Uani 1 1 d . . .
H55A H 0.5782 0.8813 0.7248 0.105 Uiso 1 1 calc R . .
H55B H 0.7068 0.9311 0.7173 0.105 Uiso 1 1 calc R . .
H55C H 0.6940 0.8786 0.7543 0.105 Uiso 1 1 calc R . .
C56 C 0.5543(7) 0.8850(3) 0.43039(16) 0.0432(15) Uani 1 1 d . . .
H56A H 0.6115 0.9156 0.4141 0.065 Uiso 1 1 calc R . .
H56B H 0.4989 0.9211 0.4445 0.065 Uiso 1 1 calc R . .
H56C H 0.5007 0.8497 0.4152 0.065 Uiso 1 1 calc R . .
C57 C 0.6538(6) 0.5485(3) 0.50826(16) 0.0351(14) Uani 1 1 d . . .
C58 C 0.7705(6) 0.4965(3) 0.50846(17) 0.0418(14) Uani 1 1 d . . .
H58A H 0.7522 0.4477 0.4946 0.063 Uiso 1 1 calc R . .
H58B H 0.7933 0.4833 0.5342 0.063 Uiso 1 1 calc R . .
H58C H 0.8426 0.5244 0.4967 0.063 Uiso 1 1 calc R . .
C59 C 0.6679(6) 0.5239(3) 0.60644(15) 0.0354(13) Uani 1 1 d . . .
C60 C 0.7966(6) 0.5057(3) 0.62405(18) 0.0438(15) Uani 1 1 d . . .
H60A H 0.8170 0.4496 0.6205 0.066 Uiso 1 1 calc R . .
H60B H 0.7928 0.5175 0.6508 0.066 Uiso 1 1 calc R . .
H60C H 0.8635 0.5383 0.6124 0.066 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.196(7) . ?
O2 C27 1.334(6) . ?
O2 C2 1.472(7) . ?
O3 C7 1.431(6) . ?
O3 C13 1.453(7) . ?
O4 C10 1.410(7) . ?
O4 C8 1.444(7) . ?
O5 C10 1.404(8) . ?
O5 C9 1.424(8) . ?
O6 C21 1.232(7) . ?
O7 C21 1.350(6) . ?
O7 C22 1.464(7) . ?
O8 C27 1.200(7) . ?
O9 C29 1.242(7) . ?
O1' C20 1.324(7) . ?
O1' C26 1.454(7) . ?
N1 C21 1.334(7) . ?
N1 C4 1.457(6) . ?
N2 C29 1.343(7) . ?
N2 C6 1.471(7) . ?
C1 C20 1.504(8) . ?
C1 C2 1.546(8) . ?
C1 C5 1.559(8) . ?
C2 C3 1.521(8) . ?
C3 C6 1.556(7) . ?
C3 C4 1.558(8) . ?
C4 C5 1.531(7) . ?
C6 C7 1.519(8) . ?
C7 C8 1.542(8) . ?
C8 C9 1.517(8) . ?
C10 C11 1.509(9) . ?
C10 C12 1.522(10) . ?
C13 C14 1.515(9) . ?
C14 C16 1.382(9) . ?
C14 C15 1.400(8) . ?
C15 C17 1.364(9) . ?
C16 C18 1.383(10) . ?
C17 C19 1.396(10) . ?
C18 C19 1.386(10) . ?
C22 C25 1.507(9) . ?
C22 C24 1.519(9) . ?
C22 C23 1.526(9) . ?
C27 C28 1.500(8) . ?
C29 C30 1.521(9) . ?
O11 C50 1.194(7) . ?
O12 C57 1.341(6) . ?
O12 C32 1.468(7) . ?
O13 C37 1.425(6) . ?
O13 C43 1.455(7) . ?
O14 C40 1.428(7) . ?
O14 C38 1.436(7) . ?
O15 C39 1.427(7) . ?
O15 C40 1.439(7) . ?
O16 C51 1.225(7) . ?
O17 C51 1.345(7) . ?
O17 C52 1.483(7) . ?
O18 C57 1.204(8) . ?
O19 C59 1.240(7) . ?
O11' C50 1.339(7) . ?
O11' C56 1.458(7) . ?
N3 C51 1.336(7) . ?
N3 C34 1.454(6) . ?
N4 C59 1.336(7) . ?
N4 C36 1.474(7) . ?
C31 C50 1.507(8) . ?
C31 C32 1.548(8) . ?
C31 C35 1.563(7) . ?
C32 C33 1.529(7) . ?
C33 C34 1.552(8) . ?
C33 C36 1.562(7) . ?
C34 C35 1.534(7) . ?
C36 C37 1.530(8) . ?
C37 C38 1.536(7) . ?
C38 C39 1.506(8) . ?
C40 C42 1.493(9) . ?
C40 C41 1.505(9) . ?
C43 C44 1.507(9) . ?
C44 C46 1.382(9) . ?
C44 C45 1.385(8) . ?
C45 C47 1.381(9) . ?
C46 C48 1.392(10) . ?
C47 C49 1.378(10) . ?
C48 C49 1.378(10) . ?
C52 C53 1.509(10) . ?
C52 C54 1.519(9) . ?
C52 C55 1.530(10) . ?
C57 C58 1.496(8) . ?
C59 C60 1.509(9) . ?

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
C27 O2 C2 118.3(5) . . ?
C7 O3 C13 116.4(4) . . ?
C10 O4 C8 106.7(5) . . ?
C10 O5 C9 107.1(5) . . ?
C21 O7 C22 121.4(5) . . ?
C20 O1' C26 115.9(5) . . ?
C21 N1 C4 123.0(4) . . ?
C29 N2 C6 124.5(5) . . ?
C20 C1 C2 112.3(5) . . ?
C20 C1 C5 111.0(4) . . ?
C2 C1 C5 105.0(4) . . ?
O2 C2 C3 106.7(4) . . ?
O2 C2 C1 105.4(5) . . ?
C3 C2 C1 106.4(4) . . ?
C2 C3 C6 112.6(4) . . ?
C2 C3 C4 101.0(5) . . ?
C6 C3 C4 120.5(5) . . ?
N1 C4 C5 109.5(4) . . ?
N1 C4 C3 117.4(5) . . ?
C5 C4 C3 103.0(4) . . ?
C4 C5 C1 105.1(4) . . ?
N2 C6 C7 112.1(5) . . ?
N2 C6 C3 111.6(5) . . ?
C7 C6 C3 112.6(4) . . ?
O3 C7 C6 106.7(5) . . ?
O3 C7 C8 112.6(5) . . ?
C6 C7 C8 112.1(5) . . ?
O4 C8 C9 102.9(5) . . ?
O4 C8 C7 107.9(5) . . ?
C9 C8 C7 118.1(5) . . ?
O5 C9 C8 105.5(5) . . ?
O5 C10 O4 104.4(5) . . ?
O5 C10 C11 114.0(6) . . ?
O4 C10 C11 111.2(5) . . ?
O5 C10 C12 107.6(6) . . ?
O4 C10 C12 108.5(6) . . ?
C11 C10 C12 110.8(6) . . ?
O3 C13 C14 113.8(5) . . ?
C16 C14 C15 119.3(6) . . ?
C16 C14 C13 120.9(6) . . ?
C15 C14 C13 119.7(6) . . ?
C17 C15 C14 121.4(6) . . ?
C14 C16 C18 119.2(6) . . ?
C15 C17 C19 119.4(6) . . ?
C16 C18 C19 121.4(7) . . ?
C18 C19 C17 119.3(7) . . ?
O1 C20 O1' 123.4(6) . . ?
O1 C20 C1 124.4(6) . . ?
O1' C20 C1 112.2(5) . . ?
O6 C21 N1 125.6(5) . . ?
O6 C21 O7 123.9(5) . . ?
N1 C21 O7 110.5(5) . . ?
O7 C22 C25 110.4(5) . . ?
O7 C22 C24 102.2(5) . . ?
C25 C22 C24 110.5(6) . . ?
O7 C22 C23 109.7(5) . . ?
C25 C22 C23 112.8(6) . . ?
C24 C22 C23 110.8(6) . . ?
O8 C27 O2 124.6(5) . . ?
O8 C27 C28 125.2(5) . . ?
O2 C27 C28 110.2(5) . . ?
O9 C29 N2 123.8(6) . . ?
O9 C29 C30 121.5(5) . . ?
N2 C29 C30 114.8(5) . . ?
C57 O12 C32 118.6(5) . . ?
C37 O13 C43 116.7(4) . . ?
C40 O14 C38 108.4(4) . . ?
C39 O15 C40 106.2(5) . . ?
C51 O17 C52 120.2(5) . . ?
C50 O11' C56 115.0(5) . . ?
C51 N3 C34 121.8(5) . . ?
C59 N4 C36 124.3(5) . . ?
C50 C31 C32 111.7(5) . . ?
C50 C31 C35 111.2(4) . . ?
C32 C31 C35 105.2(4) . . ?
O12 C32 C33 107.5(4) . . ?
O12 C32 C31 105.8(5) . . ?
C33 C32 C31 106.0(4) . . ?
C32 C33 C34 101.3(5) . . ?
C32 C33 C36 111.4(4) . . ?
C34 C33 C36 120.7(5) . . ?
N3 C34 C35 110.6(4) . . ?
N3 C34 C33 117.7(5) . . ?
C35 C34 C33 102.5(4) . . ?
C34 C35 C31 104.5(4) . . ?
N4 C36 C37 112.1(4) . . ?
N4 C36 C33 110.9(5) . . ?
C37 C36 C33 112.6(4) . . ?
O13 C37 C36 106.6(4) . . ?
O13 C37 C38 113.4(4) . . ?
C36 C37 C38 111.8(4) . . ?
O14 C38 C39 102.5(5) . . ?
O14 C38 C37 108.4(4) . . ?
C39 C38 C37 119.8(5) . . ?
O15 C39 C38 102.9(5) . . ?
O14 C40 O15 106.6(5) . . ?
O14 C40 C42 109.2(5) . . ?
O15 C40 C42 110.1(6) . . ?
O14 C40 C41 110.2(5) . . ?
O15 C40 C41 107.3(5) . . ?
C42 C40 C41 113.2(6) . . ?
O13 C43 C44 114.8(5) . . ?
C46 C44 C45 119.2(6) . . ?
C46 C44 C43 119.9(5) . . ?
C45 C44 C43 120.9(6) . . ?
C47 C45 C44 121.9(6) . . ?
C44 C46 C48 119.2(6) . . ?
C49 C47 C45 118.4(6) . . ?
C49 C48 C46 120.6(7) . . ?
C47 C49 C48 120.7(7) . . ?
O11 C50 O11' 123.4(6) . . ?
O11 C50 C31 125.2(6) . . ?
O11' C50 C31 111.4(5) . . ?
O16 C51 N3 125.2(5) . . ?
O16 C51 O17 123.9(5) . . ?
N3 C51 O17 110.8(5) . . ?
O17 C52 C53 110.0(6) . . ?
O17 C52 C54 110.2(5) . . ?
C53 C52 C54 113.0(7) . . ?
O17 C52 C55 100.9(5) . . ?
C53 C52 C55 111.4(7) . . ?
C54 C52 C55 110.6(6) . . ?
O18 C57 O12 123.7(5) . . ?
O18 C57 C58 126.2(5) . . ?
O12 C57 C58 110.1(5) . . ?
O19 C59 N4 122.8(6) . . ?
O19 C59 C60 122.0(5) . . ?
N4 C59 C60 115.1(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        68.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.080
