# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_sb2
_database_code_depnum_ccdc_archive 'CCDC 918260'
_audit_update_record             
;
2015-09-17 deposited with the CCDC.
2015-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H26 N4 O6, 2(H2 O)'
_chemical_formula_sum            'C22 H30 N4 O8'
_chemical_formula_weight         478.50

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.864(3)
_cell_length_b                   10.055(4)
_cell_length_c                   15.262(6)
_cell_angle_alpha                73.795(6)
_cell_angle_beta                 81.426(7)
_cell_angle_gamma                81.877(7)
_cell_volume                     1139.5(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2502
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.175
_exptl_crystal_density_meas      1.395
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508.0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10638
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         25.29
_reflns_number_total             4015
_reflns_number_gt                2767
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.1073P)²+1.4002P] 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_number_reflns         4015
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1506
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   0.779
_refine_ls_restrained_S_all      0.779
_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 -0.0174(2) 0.17866(18) 1.13239(11) 0.0232(4) Uani 1 1 d . . .
O1S O 0.3075(3) 0.1249(2) 0.28308(14) 0.0270(5) Uani 1 1 d . . .
O2S O 0.1783(3) 0.2963(2) 0.79369(15) 0.0320(5) Uani 1 1 d . . .
O2 O 0.0635(3) 0.17509(18) 0.98490(12) 0.0273(5) Uani 1 1 d . . .
O3 O 0.4534(2) 0.70266(18) 0.83631(12) 0.0247(4) Uani 1 1 d . . .
O4 O 0.2634(2) 1.01846(18) 0.62682(11) 0.0229(4) Uani 1 1 d . . .
O5 O 0.3369(2) 1.09564(18) 0.47463(12) 0.0239(4) Uani 1 1 d . . .
N1 N 0.2250(3) 0.4118(2) 0.95676(14) 0.0180(5) Uani 1 1 d . . .
N2 N 0.3825(3) 0.5270(2) 0.78611(14) 0.0217(5) Uani 1 1 d . . .
H2 H 0.3303 0.4530 0.8000 0.026 Uiso 1 1 calc R . .
N3 N 0.2405(3) 0.8446(2) 0.27658(14) 0.0222(5) Uani 1 1 d . . .
H3 H 0.2659 0.9157 0.2909 0.027 Uiso 1 1 calc R . .
O20 O 0.1011(2) 0.64931(19) 0.32405(13) 0.0286(5) Uani 1 1 d . . .
C1 C -0.1099(4) 0.0573(3) 1.14902(18) 0.0244(6) Uani 1 1 d . . .
H1A H -0.2321 0.0850 1.1536 0.037 Uiso 1 1 calc R . .
H1B H -0.0815 -0.0082 1.2053 0.037 Uiso 1 1 calc R . .
H1C H -0.0772 0.0146 1.0992 0.037 Uiso 1 1 calc R . .
C2 C 0.0624(3) 0.2269(3) 1.04822(16) 0.0190(6) Uani 1 1 d . . .
C3 C 0.1472(3) 0.3547(2) 1.04056(16) 0.0184(6) Uani 1 1 d . . .
C4 C 0.2966(3) 0.5294(2) 0.94497(16) 0.0181(6) Uani 1 1 d . . .
C5 C 0.3835(3) 0.5942(3) 0.85060(17) 0.0191(6) Uani 1 1 d . . .
C6 C 0.4678(4) 0.5765(3) 0.69264(17) 0.0242(6) Uani 1 1 d . . .
H6A H 0.5912 0.5729 0.6945 0.029 Uiso 1 1 calc R . .
H6B H 0.4243 0.6727 0.6670 0.029 Uiso 1 1 calc R . .
C7 C 0.4362(3) 0.4882(3) 0.63110(17) 0.0212(6) Uani 1 1 d . . .
H7A H 0.3126 0.4886 0.6316 0.025 Uiso 1 1 calc R . .
H7B H 0.4839 0.3928 0.6556 0.025 Uiso 1 1 calc R . .
C8 C 0.5174(3) 0.5415(3) 0.53223(17) 0.0228(6) Uani 1 1 d . . .
H8A H 0.6414 0.5382 0.5319 0.027 Uiso 1 1 calc R . .
H8B H 0.4729 0.6381 0.5089 0.027 Uiso 1 1 calc R . .
C9 C 0.1407(3) 0.4100(3) 1.11530(17) 0.0201(6) Uani 1 1 d . . .
H9 H 0.0875 0.3660 1.1727 0.024 Uiso 1 1 calc R . .
C10 C 0.2157(3) 0.5324(3) 1.10209(17) 0.0228(6) Uani 1 1 d . . .
H10 H 0.2132 0.5722 1.1505 0.027 Uiso 1 1 calc R . .
C11 C 0.2941(3) 0.5938(3) 1.01556(17) 0.0208(6) Uani 1 1 d . . .
H11 H 0.3441 0.6762 1.0045 0.025 Uiso 1 1 calc R . .
C12 C 0.3453(4) 1.1325(3) 0.63832(18) 0.0245(6) Uani 1 1 d . . .
H12A H 0.4661 1.1227 0.6164 0.037 Uiso 1 1 calc R . .
H12B H 0.3320 1.1306 0.7022 0.037 Uiso 1 1 calc R . .
H12C H 0.2919 1.2195 0.6040 0.037 Uiso 1 1 calc R . .
C13 C 0.2694(3) 1.0129(3) 0.53977(16) 0.0196(6) Uani 1 1 d . . .
C14 C 0.1819(3) 0.8940(3) 0.53271(16) 0.0188(6) Uani 1 1 d . . .
N10 N 0.2002(3) 0.8753(2) 0.44788(14) 0.0191(5) Uani 1 1 d . . .
C16 C 0.1244(3) 0.7722(3) 0.43556(17) 0.0197(6) Uani 1 1 d . . .
C17 C 0.1536(3) 0.7508(3) 0.33985(18) 0.0213(6) Uani 1 1 d . . .
C18 C 0.2941(4) 0.8305(3) 0.18339(17) 0.0234(6) Uani 1 1 d . . .
H18A H 0.1926 0.8339 0.1534 0.028 Uiso 1 1 calc R . .
H18B H 0.3612 0.7411 0.1861 0.028 Uiso 1 1 calc R . .
C19 C 0.4017(4) 0.9464(3) 0.12810(17) 0.0231(6) Uani 1 1 d . . .
H19A H 0.5062 0.9396 0.1565 0.028 Uiso 1 1 calc R . .
H19B H 0.3368 1.0357 0.1290 0.028 Uiso 1 1 calc R . .
C20 C 0.4507(3) 0.9398(3) 0.02911(17) 0.0233(6) Uani 1 1 d . . .
H20A H 0.3463 0.9405 0.0021 0.028 Uiso 1 1 calc R . .
H20B H 0.5213 0.8528 0.0283 0.028 Uiso 1 1 calc R . .
C21 C 0.0869(3) 0.8108(3) 0.60788(17) 0.0224(6) Uani 1 1 d . . .
H21 H 0.0771 0.8260 0.6659 0.027 Uiso 1 1 calc R . .
C22 C 0.0076(3) 0.7049(3) 0.59355(18) 0.0254(6) Uani 1 1 d . . .
H22 H -0.0568 0.6479 0.6420 0.030 Uiso 1 1 calc R . .
C23 C 0.0258(3) 0.6853(3) 0.50596(18) 0.0221(6) Uani 1 1 d . . .
H23 H -0.0268 0.6155 0.4946 0.026 Uiso 1 1 calc R . .
H30 H 0.326(4) 0.118(3) 0.337(2) 0.034(9) Uiso 1 1 d . . .
H31 H 0.403(5) 0.180(4) 0.251(3) 0.066(12) Uiso 1 1 d . . .
H32 H 0.083(6) 0.318(5) 0.758(3) 0.094(16) Uiso 1 1 d . . .
H33 H 0.148(5) 0.273(4) 0.852(3) 0.069(13) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.333(3) . ?
O1 C1 1.451(3) . ?
O1S H30 0.83(3) . ?
O1S H31 0.98(5) . ?
O2S H32 0.95(5) . ?
O2S H33 0.86(4) . ?
O2 C2 1.218(3) . ?
O3 C5 1.241(3) . ?
O4 C13 1.339(3) . ?
O4 C12 1.455(3) . ?
O5 C13 1.212(3) . ?
N1 C4 1.337(3) . ?
N1 C3 1.340(3) . ?
N2 C5 1.341(3) . ?
N2 C6 1.465(3) . ?
N2 H2 0.8600 . ?
N3 C17 1.329(4) . ?
N3 C18 1.462(3) . ?
N3 H3 0.8600 . ?
O20 C17 1.247(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.499(4) . ?
C3 C9 1.393(3) . ?
C4 C11 1.399(3) . ?
C4 C5 1.508(4) . ?
C6 C7 1.526(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.526(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C8 1.531(5) 2_666 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.497(4) . ?
C14 N10 1.343(3) . ?
C14 C21 1.400(4) . ?
N10 C16 1.336(3) . ?
C16 C23 1.392(4) . ?
C16 C17 1.515(4) . ?
C18 C19 1.518(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.520(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C20 1.522(6) 2_675 ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.389(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.389(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 117.64(19) . . ?
H30 O1S H31 98(3) . . ?
H32 O2S H33 114(4) . . ?
C13 O4 C12 114.9(2) . . ?
C4 N1 C3 117.4(2) . . ?
C5 N2 C6 121.7(2) . . ?
C5 N2 H2 119.1 . . ?
C6 N2 H2 119.1 . . ?
C17 N3 C18 122.0(2) . . ?
C17 N3 H3 119.0 . . ?
C18 N3 H3 119.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 124.2(2) . . ?
O2 C2 C3 124.1(2) . . ?
O1 C2 C3 111.6(2) . . ?
N1 C3 C9 123.5(2) . . ?
N1 C3 C2 114.9(2) . . ?
C9 C3 C2 121.6(2) . . ?
N1 C4 C11 123.1(2) . . ?
N1 C4 C5 117.6(2) . . ?
C11 C4 C5 119.3(2) . . ?
O3 C5 N2 123.5(2) . . ?
O3 C5 C4 120.1(2) . . ?
N2 C5 C4 116.4(2) . . ?
N2 C6 C7 111.3(2) . . ?
N2 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 112.3(2) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C8 113.7(3) . 2_666 ?
C7 C8 H8A 108.8 . . ?
C8 C8 H8A 108.8 2_666 . ?
C7 C8 H8B 108.8 . . ?
C8 C8 H8B 108.8 2_666 . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C3 118.5(2) . . ?
C10 C9 H9 120.8 . . ?
C3 C9 H9 120.8 . . ?
C11 C10 C9 118.7(2) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C4 118.7(2) . . ?
C10 C11 H11 120.6 . . ?
C4 C11 H11 120.6 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 O4 123.5(2) . . ?
O5 C13 C14 124.4(2) . . ?
O4 C13 C14 112.2(2) . . ?
N10 C14 C21 122.9(2) . . ?
N10 C14 C13 114.3(2) . . ?
C21 C14 C13 122.8(2) . . ?
C16 N10 C14 118.0(2) . . ?
N10 C16 C23 123.1(2) . . ?
N10 C16 C17 116.5(2) . . ?
C23 C16 C17 120.4(2) . . ?
O20 C17 N3 123.7(2) . . ?
O20 C17 C16 120.8(2) . . ?
N3 C17 C16 115.5(2) . . ?
N3 C18 C19 110.7(2) . . ?
N3 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 C20 112.0(2) . . ?
C18 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 C20 112.9(3) . 2_675 ?
C19 C20 H20A 109.0 . . ?
C20 C20 H20A 109.0 2_675 . ?
C19 C20 H20B 109.0 . . ?
C20 C20 H20B 109.0 2_675 . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C14 118.2(2) . . ?
C22 C21 H21 120.9 . . ?
C14 C21 H21 120.9 . . ?
C21 C22 C23 119.1(3) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C22 C23 C16 118.7(3) . . ?
C22 C23 H23 120.7 . . ?
C16 C23 H23 120.7 . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        25.29
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.056
