# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_publication
_database_code_depnum_ccdc_archive 'CCDC 1031071'
_audit_update_record             
;
2014-10-26 deposited with the CCDC.
2015-01-29 downloaded from the CCDC.
;
_chemical_name_common            wcz1
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C47 H74 N20 O25'
_chemical_formula_weight         1319.26

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pmmn

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

_cell_length_a                   17.916(13)
_cell_length_b                   11.364(8)
_cell_length_c                   14.414(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2935(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            lightbrown
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'SADABS (Bruker, 2005)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD Area Detector'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19700
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2842
_reflns_number_gt                1501
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0028(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2842
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1600
_refine_ls_R_factor_gt           0.1102
_refine_ls_wR_factor_ref         0.3736
_refine_ls_wR_factor_gt          0.3452
_refine_ls_goodness_of_fit_ref   1.222
_refine_ls_restrained_S_all      1.222
_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
C15 C 0.5458(6) 0.0073(10) 1.5764(6) 0.107(3) Uani 1 1 d . . .
C16 C 0.5635(5) 0.0637(7) 1.4951(6) 0.101(3) Uani 1 1 d . . .
H16 H 0.6082 0.1049 1.4905 0.121 Uiso 1 1 calc R . .
C17 C 0.5164(6) 0.0600(7) 1.4208(5) 0.091(2) Uani 1 1 d . . .
H17 H 0.5270 0.1040 1.3680 0.110 Uiso 1 1 calc R . .
O4 O 0.5868(6) 0.0130(12) 1.6545(6) 0.225(5) Uani 1 1 d . . .
H4 H 0.6231 0.0555 1.6458 0.338 Uiso 1 1 calc R . .
C1 C 0.7500 -0.0765(7) 0.8621(5) 0.055(2) Uani 1 2 d S . .
C2 C 0.7079(5) -0.2500 0.7881(6) 0.067(2) Uani 1 2 d S . .
C3 C 0.6148(3) -0.0986(5) 0.8507(4) 0.0642(17) Uani 1 1 d . . .
H3A H 0.5851 -0.1202 0.7971 0.077 Uiso 1 1 calc R . .
H3B H 0.6167 -0.0134 0.8534 0.077 Uiso 1 1 calc R . .
C4 C 0.5796(3) -0.0805(5) 1.0163(4) 0.0575(15) Uani 1 1 d . . .
C5 C 0.5335(4) -0.2500 0.9413(6) 0.060(2) Uani 1 2 d S . .
C6 C 0.5093(4) -0.2500 1.0410(7) 0.063(2) Uani 1 2 d S . .
H6 H 0.4547 -0.2500 1.0462 0.076 Uiso 1 2 calc SR . .
C7 C 0.5316(3) -0.1002(5) 1.1740(5) 0.0629(16) Uani 1 1 d . . .
H7A H 0.5342 -0.0149 1.1728 0.075 Uiso 1 1 calc R . .
H7B H 0.4818 -0.1214 1.1945 0.075 Uiso 1 1 calc R . .
C8 C 0.6436(3) -0.0791(5) 1.2674(4) 0.0529(14) Uani 1 1 d . . .
C9 C 0.5748(5) -0.2500 1.2953(6) 0.061(2) Uani 1 2 d S . .
H9 H 0.5280 -0.2500 1.3305 0.073 Uiso 1 2 calc SR . .
C10 C 0.6437(4) -0.2500 1.3607(5) 0.054(2) Uani 1 2 d S . .
C11 C 0.7500 -0.0979(7) 1.3752(6) 0.062(2) Uani 1 2 d S . .
H11A H 0.7500 -0.1177 1.4406 0.074 Uiso 1 2 calc SR . .
H11B H 0.7500 -0.0128 1.3700 0.074 Uiso 1 2 calc SR . .
C12 C 0.6862(15) -0.2500 0.6935(12) 0.091(7) Uani 0.50 2 d SP . .
H12A H 0.7010 -0.3228 0.6652 0.136 Uiso 0.25 1 calc PR . .
H12B H 0.7099 -0.1856 0.6620 0.136 Uiso 0.25 1 calc PR . .
H12C H 0.6330 -0.2416 0.6893 0.136 Uiso 0.25 1 calc PR . .
C13 C 0.4708(5) -0.2500 0.8678(7) 0.083(3) Uani 1 2 d S . .
H13A H 0.4425 -0.3215 0.8727 0.125 Uiso 0.50 1 calc PR . .
H13B H 0.4923 -0.2446 0.8070 0.125 Uiso 0.50 1 calc PR . .
H13C H 0.4384 -0.1839 0.8781 0.125 Uiso 0.50 1 calc PR . .
C14 C 0.6243(7) -0.2500 1.4600(7) 0.091(3) Uani 1 2 d S . .
H14A H 0.5989 -0.3218 1.4752 0.136 Uiso 0.50 1 calc PR . .
H14B H 0.5924 -0.1843 1.4732 0.136 Uiso 0.50 1 calc PR . .
H14C H 0.6691 -0.2439 1.4963 0.136 Uiso 0.50 1 calc PR . .
N1 N 0.6894(3) -0.1425(4) 0.8379(3) 0.0574(13) Uani 1 1 d . . .
N2 N 0.5775(3) -0.1416(4) 0.9338(4) 0.0634(14) Uani 1 1 d . . .
N3 N 0.5414(3) -0.1429(4) 1.0806(3) 0.0593(13) Uani 1 1 d . . .
N4 N 0.5832(2) -0.1415(4) 1.2403(3) 0.0570(13) Uani 1 1 d . . .
N5 N 0.6823(3) -0.1438(4) 1.3328(3) 0.0543(12) Uani 1 1 d . . .
O1 O 0.7500 0.0197(5) 0.8956(4) 0.0646(15) Uani 1 2 d S . .
O2 O 0.6081(2) 0.0159(3) 1.0279(3) 0.0714(13) Uani 1 1 d . . .
O3 O 0.6611(2) 0.0201(3) 1.2397(3) 0.0652(12) 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
C15 O4 1.346(13) . ?
C15 C17 1.352(13) 5_658 ?
C15 C16 1.374(11) . ?
C16 C17 1.364(12) . ?
C16 H16 0.9300 . ?
C17 C15 1.352(13) 5_658 ?
C17 H17 0.9300 . ?
O4 H4 0.8200 . ?
C1 O1 1.195(9) . ?
C1 N1 1.366(6) . ?
C1 N1 1.366(6) 7_755 ?
C2 C12 1.42(2) . ?
C2 N1 1.454(6) . ?
C2 N1 1.454(6) 8 ?
C2 C2 1.508(18) 2_645 ?
C3 N1 1.438(8) . ?
C3 N2 1.455(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O2 1.220(6) . ?
C4 N3 1.353(7) . ?
C4 N2 1.378(7) . ?
C5 N2 1.466(6) . ?
C5 N2 1.466(6) 8 ?
C5 C6 1.502(13) . ?
C5 C13 1.544(13) . ?
C6 N3 1.463(7) . ?
C6 N3 1.463(7) 8 ?
C6 H6 0.9800 . ?
C7 N4 1.410(7) . ?
C7 N3 1.442(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O3 1.237(6) . ?
C8 N4 1.352(7) . ?
C8 N5 1.382(7) . ?
C9 N4 1.473(6) . ?
C9 N4 1.473(6) 8 ?
C9 C10 1.554(12) . ?
C9 H9 0.9800 . ?
C10 N5 1.448(6) . ?
C10 N5 1.448(6) 8 ?
C10 C14 1.472(12) . ?
C11 N5 1.455(6) . ?
C11 N5 1.455(6) 7_755 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 C15 C17 116.9(9) . 5_658 ?
O4 C15 C16 124.4(12) . . ?
C17 C15 C16 118.7(9) 5_658 . ?
C17 C16 C15 120.9(8) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C15 C17 C16 120.3(8) 5_658 . ?
C15 C17 H17 119.9 5_658 . ?
C16 C17 H17 119.9 . . ?
C15 O4 H4 109.5 . . ?
O1 C1 N1 127.3(3) . . ?
O1 C1 N1 127.3(3) . 7_755 ?
N1 C1 N1 105.4(6) . 7_755 ?
C12 C2 N1 114.3(6) . . ?
C12 C2 N1 114.3(6) . 8 ?
N1 C2 N1 114.2(7) . 8 ?
C12 C2 C2 105.9(11) . 2_645 ?
N1 C2 C2 103.2(4) . 2_645 ?
N1 C2 C2 103.2(4) 8 2_645 ?
N1 C3 N2 114.6(4) . . ?
N1 C3 H3A 108.6 . . ?
N2 C3 H3A 108.6 . . ?
N1 C3 H3B 108.6 . . ?
N2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
O2 C4 N3 126.0(6) . . ?
O2 C4 N2 125.6(6) . . ?
N3 C4 N2 108.3(5) . . ?
N2 C5 N2 114.3(6) . 8 ?
N2 C5 C6 103.1(5) . . ?
N2 C5 C6 103.1(5) 8 . ?
N2 C5 C13 109.9(5) . . ?
N2 C5 C13 109.9(5) 8 . ?
C6 C5 C13 116.4(7) . . ?
N3 C6 N3 112.7(6) . 8 ?
N3 C6 C5 105.1(5) . . ?
N3 C6 C5 105.1(5) 8 . ?
N3 C6 H6 111.2 . . ?
N3 C6 H6 111.2 8 . ?
C5 C6 H6 111.2 . . ?
N4 C7 N3 116.2(4) . . ?
N4 C7 H7A 108.2 . . ?
N3 C7 H7A 108.2 . . ?
N4 C7 H7B 108.2 . . ?
N3 C7 H7B 108.2 . . ?
H7A C7 H7B 107.4 . . ?
O3 C8 N4 126.0(5) . . ?
O3 C8 N5 125.3(5) . . ?
N4 C8 N5 108.6(5) . . ?
N4 C9 N4 113.6(6) . 8 ?
N4 C9 C10 104.2(4) . . ?
N4 C9 C10 104.2(4) 8 . ?
N4 C9 H9 111.5 . . ?
N4 C9 H9 111.5 8 . ?
C10 C9 H9 111.5 . . ?
N5 C10 N5 112.9(6) . 8 ?
N5 C10 C14 112.5(4) . . ?
N5 C10 C14 112.5(4) 8 . ?
N5 C10 C9 102.2(4) . . ?
N5 C10 C9 102.2(4) 8 . ?
C14 C10 C9 113.7(7) . . ?
N5 C11 N5 113.0(6) . 7_755 ?
N5 C11 H11A 109.0 . . ?
N5 C11 H11A 109.0 7_755 . ?
N5 C11 H11B 109.0 . . ?
N5 C11 H11B 109.0 7_755 . ?
H11A C11 H11B 107.8 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C3 121.0(4) . . ?
C1 N1 C2 114.0(5) . . ?
C3 N1 C2 124.5(5) . . ?
C4 N2 C3 121.9(5) . . ?
C4 N2 C5 112.0(6) . . ?
C3 N2 C5 126.1(5) . . ?
C4 N3 C7 121.7(5) . . ?
C4 N3 C6 111.6(5) . . ?
C7 N3 C6 126.6(6) . . ?
C8 N4 C7 123.1(5) . . ?
C8 N4 C9 111.4(5) . . ?
C7 N4 C9 125.2(5) . . ?
C8 N5 C10 113.2(5) . . ?
C8 N5 C11 120.9(5) . . ?
C10 N5 C11 125.5(6) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.988
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.090

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.750 0.250 0.587 282 101 ' '
2 0.250 0.250 0.912 60 11 ' '
3 0.250 0.750 0.393 278 101 ' '
4 0.750 0.750 0.088 56 10 ' '
_platon_squeeze_details          
;
;

