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

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

data_trya5
_database_code_depnum_ccdc_archive 'CCDC 1024772'
_audit_update_record             
;
2015-09-03 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H23 N5 O8'
_chemical_formula_sum            'C25 H23 N5 O8'
_chemical_compound_source        Synthesized
_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_chemical_formula_weight         521.48

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'
_symmetry_int_tables_number      2
_chemical_absolute_configuration syn

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

_cell_length_a                   7.856(5)
_cell_length_b                   11.799(7)
_cell_length_c                   14.315(8)
_cell_angle_alpha                66.980(14)
_cell_angle_beta                 77.401(15)
_cell_angle_gamma                74.377(16)
_cell_volume                     1166.7(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71066
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SADABS Bruker'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13108
_diffrn_reflns_av_R_equivalents  0.1699
_diffrn_reflns_av_sigmaI/netI    0.1811
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         23.26
_reflns_number_total             3237
_reflns_number_gt                2226
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0650P)²+2.0559P] 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     SHELXL
_refine_ls_extinction_coef       0.000
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3237
_refine_ls_number_parameters     354
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.2665
_refine_ls_R_factor_gt           0.1021
_refine_ls_wR_factor_ref         0.2479
_refine_ls_wR_factor_gt          0.1971
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.06
_refine_ls_shift/su_mean         0.028

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
O3 O 0.0493(9) 0.6397(7) -0.0082(4) 0.074(2) Uani 1 1 d U . .
O1 O 0.3818(7) 0.3057(5) 0.9450(4) 0.0554(18) Uani 1 1 d . . .
N1 N 0.2265(8) 0.8125(7) 0.1964(5) 0.053(2) Uani 1 1 d . . .
H1A H 0.1879 0.7596 0.1831 0.063 Uiso 1 1 calc R . .
N2 N 0.1984(8) 0.5796(7) 0.3261(5) 0.0437(19) Uani 1 1 d . . .
N3 N 0.1080(8) 0.4361(7) 0.2449(4) 0.049(2) Uani 1 1 d . . .
H3 H 0.1243 0.5116 0.2117 0.059 Uiso 1 1 calc R . .
O4 O 0.1563(7) 0.6695(5) 0.1040(4) 0.0582(18) Uani 1 1 d U . .
C1 C 0.5216(12) 0.2583(9) 1.1706(7) 0.074(3) Uani 1 1 d . . .
H1 H 0.5568 0.2169 1.2356 0.089 Uiso 1 1 calc R . .
C2 C 0.4777(10) 0.3099(8) 1.0895(6) 0.052(3) Uani 1 1 d . . .
C3 C 0.4279(11) 0.3854(8) 0.9852(5) 0.056(3) Uani 1 1 d . . .
H3A H 0.3274 0.4536 0.9879 0.067 Uiso 1 1 calc R . .
H3B H 0.5271 0.4216 0.9411 0.067 Uiso 1 1 calc R . .
C4 C 0.3485(11) 0.3596(9) 0.8455(6) 0.049(3) Uani 1 1 d . . .
C5 C 0.3754(10) 0.4781(9) 0.7803(6) 0.053(3) Uani 1 1 d . . .
H5 H 0.4135 0.5291 0.8039 0.063 Uiso 1 1 calc R . .
C6 C 0.3445(10) 0.5195(9) 0.6788(6) 0.050(3) Uani 1 1 d . . .
H6 H 0.3614 0.5994 0.6353 0.060 Uiso 1 1 calc R . .
C7 C 0.2894(10) 0.4459(9) 0.6405(6) 0.041(2) Uani 1 1 d . . .
C10 C 0.2602(10) 0.4901(9) 0.5311(6) 0.039(2) Uani 1 1 d . . .
C11 C 0.2710(9) 0.6143(8) 0.4661(6) 0.044(2) Uani 1 1 d . . .
H11 H 0.2962 0.6696 0.4905 0.053 Uiso 1 1 calc R . .
C12 C 0.2433(10) 0.6521(9) 0.3650(6) 0.041(2) Uani 1 1 d . . .
C20 C 0.2640(11) 0.7811(9) 0.2933(6) 0.051(3) Uani 1 1 d . . .
C24 C 0.2468(13) 0.9219(10) 0.1209(7) 0.069(3) Uani 1 1 d . . .
H24 H 0.2210 0.9385 0.0559 0.083 Uiso 1 1 calc R . .
C23 C 0.3057(13) 1.0084(10) 0.1402(8) 0.075(3) Uani 1 1 d . . .
H23 H 0.3197 1.0846 0.0885 0.090 Uiso 1 1 calc R . .
C13 C 0.1883(10) 0.4618(9) 0.3891(6) 0.041(2) Uani 1 1 d . . .
C15 C 0.1380(10) 0.3837(9) 0.3431(6) 0.046(2) Uani 1 1 d . . .
C19 C 0.0547(11) 0.3795(10) 0.1948(6) 0.052(3) Uani 1 1 d . . .
H19 H 0.0350 0.4215 0.1268 0.063 Uiso 1 1 calc R . .
C18 C 0.0297(11) 0.2597(10) 0.2449(7) 0.057(3) Uani 1 1 d . . .
H18 H -0.0086 0.2196 0.2113 0.069 Uiso 1 1 calc R . .
C17 C 0.0604(11) 0.1987(9) 0.3435(6) 0.057(3) Uani 1 1 d . . .
H17 H 0.0459 0.1161 0.3772 0.069 Uiso 1 1 calc R . .
C16 C 0.1141(11) 0.2606(9) 0.3947(6) 0.054(3) Uani 1 1 d . . .
H16 H 0.1336 0.2196 0.4629 0.065 Uiso 1 1 calc R . .
C14 C 0.2197(9) 0.4134(8) 0.4901(6) 0.044(2) Uani 1 1 d . . .
H14 H 0.2138 0.3303 0.5300 0.053 Uiso 1 1 calc R . .
C22 C 0.3447(12) 0.9813(9) 0.2381(8) 0.069(3) Uani 1 1 d . . .
H22 H 0.3836 1.0398 0.2525 0.083 Uiso 1 1 calc R . .
C21 C 0.3252(12) 0.8669(9) 0.3137(6) 0.056(3) Uani 1 1 d . . .
H21 H 0.3537 0.8478 0.3786 0.067 Uiso 1 1 calc R . .
C8 C 0.2596(10) 0.3263(9) 0.7091(6) 0.052(3) Uani 1 1 d . . .
H8 H 0.2194 0.2756 0.6862 0.063 Uiso 1 1 calc R . .
C9 C 0.2897(11) 0.2847(8) 0.8093(6) 0.055(3) Uani 1 1 d . . .
H9 H 0.2707 0.2056 0.8535 0.066 Uiso 1 1 calc R . .
N4 N 0.0802(10) 0.7159(9) 0.0230(6) 0.061(2) Uani 1 1 d U . .
O2 O 0.0398(9) 0.8297(7) -0.0189(5) 0.090(2) Uani 1 1 d U . .
O7 O 0.197(3) 0.9381(19) 0.6818(18) 0.394(18) Uani 1 1 d . . .
O9 O 0.1320(13) 1.1223(11) 0.6443(6) 0.136(4) Uani 1 1 d . . .
N5 N 0.222(5) 1.0275(15) 0.630(2) 0.46(3) Uani 1 1 d . . .
O8 O 0.4098(18) 1.002(2) 0.6100(11) 0.396(18) Uani 1 1 d D . .
C100 C 0.296(4) 0.938(3) 0.5051(17) 0.322(14) Uani 1 1 d D . .
O6 O 0.4320(10) 0.8114(8) 0.5496(6) 0.111(3) Uani 1 1 d . . .
O5 O -0.824(3) 1.027(2) 0.823(4) 0.38(4) Uani 0.52(3) 1 d P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 N4 1.244(9) . ?
O1 C4 1.367(8) . ?
O1 C3 1.430(9) . ?
N1 C24 1.343(10) . ?
N1 C20 1.365(9) . ?
N2 C12 1.337(10) . ?
N2 C13 1.341(9) . ?
N3 C19 1.339(10) . ?
N3 C15 1.341(9) . ?
O4 N4 1.277(8) . ?
C1 C2 1.160(10) . ?
C2 C3 1.484(10) . ?
C4 C5 1.387(11) . ?
C4 C9 1.395(11) . ?
C5 C6 1.394(10) . ?
C6 C7 1.388(11) . ?
C7 C8 1.415(11) . ?
C7 C10 1.492(10) . ?
C10 C14 1.385(10) . ?
C10 C11 1.410(10) . ?
C11 C12 1.387(9) . ?
C12 C20 1.495(11) . ?
C20 C21 1.376(11) . ?
C24 C23 1.364(12) . ?
C23 C22 1.395(11) . ?
C13 C14 1.383(9) . ?
C13 C15 1.491(11) . ?
C15 C16 1.392(11) . ?
C19 C18 1.358(11) . ?
C18 C17 1.352(10) . ?
C17 C16 1.404(11) . ?
C22 C21 1.383(11) . ?
C8 C9 1.374(10) . ?
N4 O2 1.220(9) . ?
O7 N5 1.07(2) . ?
O9 N5 1.216(18) . ?
N5 O8 1.41(4) . ?
C100 O6 1.57(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
C4 O1 C3 115.7(7) . . ?
C24 N1 C20 123.3(8) . . ?
C12 N2 C13 116.7(7) . . ?
C19 N3 C15 124.8(8) . . ?
C1 C2 C3 174.9(10) . . ?
O1 C3 C2 109.0(7) . . ?
O1 C4 C5 124.6(9) . . ?
O1 C4 C9 115.4(8) . . ?
C5 C4 C9 120.0(8) . . ?
C4 C5 C6 118.9(9) . . ?
C7 C6 C5 122.3(8) . . ?
C6 C7 C8 117.7(7) . . ?
C6 C7 C10 121.9(8) . . ?
C8 C7 C10 120.5(8) . . ?
C14 C10 C11 117.7(7) . . ?
C14 C10 C7 122.2(8) . . ?
C11 C10 C7 120.1(8) . . ?
C12 C11 C10 118.5(8) . . ?
N2 C12 C11 123.9(8) . . ?
N2 C12 C20 116.8(7) . . ?
C11 C12 C20 119.3(9) . . ?
N1 C20 C21 117.7(8) . . ?
N1 C20 C12 115.4(8) . . ?
C21 C20 C12 126.7(8) . . ?
N1 C24 C23 119.6(9) . . ?
C24 C23 C22 119.3(10) . . ?
N2 C13 C14 123.9(8) . . ?
N2 C13 C15 115.2(7) . . ?
C14 C13 C15 120.9(8) . . ?
N3 C15 C16 116.6(8) . . ?
N3 C15 C13 118.2(8) . . ?
C16 C15 C13 125.2(8) . . ?
N3 C19 C18 119.0(8) . . ?
C17 C18 C19 120.2(9) . . ?
C18 C17 C16 119.8(9) . . ?
C15 C16 C17 119.7(8) . . ?
C10 C14 C13 119.2(8) . . ?
C21 C22 C23 119.6(10) . . ?
C20 C21 C22 120.4(8) . . ?
C9 C8 C7 120.4(8) . . ?
C8 C9 C4 120.8(8) . . ?
O2 N4 O3 123.4(8) . . ?
O2 N4 O4 120.0(9) . . ?
O3 N4 O4 116.6(8) . . ?
O7 N5 O9 119(3) . . ?
O7 N5 O8 102(2) . . ?
O9 N5 O8 125(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 C3 C2 -174.3(7) . . . . ?
C1 C2 C3 O1 167(11) . . . . ?
C3 O1 C4 C5 7.4(11) . . . . ?
C3 O1 C4 C9 -175.0(8) . . . . ?
O1 C4 C5 C6 176.8(7) . . . . ?
C9 C4 C5 C6 -0.6(13) . . . . ?
C4 C5 C6 C7 -0.6(12) . . . . ?
C5 C6 C7 C8 1.8(12) . . . . ?
C5 C6 C7 C10 -178.7(7) . . . . ?
C6 C7 C10 C14 174.5(8) . . . . ?
C8 C7 C10 C14 -6.1(11) . . . . ?
C6 C7 C10 C11 -6.4(11) . . . . ?
C8 C7 C10 C11 173.0(7) . . . . ?
C14 C10 C11 C12 -0.9(11) . . . . ?
C7 C10 C11 C12 180.0(7) . . . . ?
C13 N2 C12 C11 -3.1(11) . . . . ?
C13 N2 C12 C20 176.9(7) . . . . ?
C10 C11 C12 N2 3.3(11) . . . . ?
C10 C11 C12 C20 -176.7(7) . . . . ?
C24 N1 C20 C21 0.2(12) . . . . ?
C24 N1 C20 C12 -176.4(8) . . . . ?
N2 C12 C20 N1 2.9(11) . . . . ?
C11 C12 C20 N1 -177.2(7) . . . . ?
N2 C12 C20 C21 -173.4(9) . . . . ?
C11 C12 C20 C21 6.5(13) . . . . ?
C20 N1 C24 C23 -0.8(14) . . . . ?
N1 C24 C23 C22 0.3(16) . . . . ?
C12 N2 C13 C14 0.6(11) . . . . ?
C12 N2 C13 C15 -180.0(7) . . . . ?
C19 N3 C15 C16 1.2(11) . . . . ?
C19 N3 C15 C13 -177.0(8) . . . . ?
N2 C13 C15 N3 0.1(10) . . . . ?
C14 C13 C15 N3 179.6(7) . . . . ?
N2 C13 C15 C16 -177.9(8) . . . . ?
C14 C13 C15 C16 1.5(12) . . . . ?
C15 N3 C19 C18 -0.7(12) . . . . ?
N3 C19 C18 C17 -0.7(13) . . . . ?
C19 C18 C17 C16 1.5(13) . . . . ?
N3 C15 C16 C17 -0.3(12) . . . . ?
C13 C15 C16 C17 177.7(8) . . . . ?
C18 C17 C16 C15 -1.0(13) . . . . ?
C11 C10 C14 C13 -1.3(11) . . . . ?
C7 C10 C14 C13 177.8(7) . . . . ?
N2 C13 C14 C10 1.6(12) . . . . ?
C15 C13 C14 C10 -177.8(8) . . . . ?
C24 C23 C22 C21 0.8(15) . . . . ?
N1 C20 C21 C22 1.0(13) . . . . ?
C12 C20 C21 C22 177.2(8) . . . . ?
C23 C22 C21 C20 -1.4(14) . . . . ?
C6 C7 C8 C9 -1.8(12) . . . . ?
C10 C7 C8 C9 178.8(7) . . . . ?
C7 C8 C9 C4 0.6(12) . . . . ?
O1 C4 C9 C8 -177.0(7) . . . . ?
C5 C4 C9 C8 0.6(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        23.26
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.070

