# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1937519'
loop_
_audit_author_name
_audit_author_address
'Sabine Foro'
;Institue of Materials Science, Darmstadt University of Technology
Germany
;
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H16 N10 O10 Y, N O3'
_chemical_formula_sum            'C4 H16 N11 O13 Y'
_chemical_formula_weight         515.19

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'
Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5428(7)
_cell_length_b                   11.256(1)
_cell_length_c                   11.976(1)
_cell_angle_alpha                112.238(8)
_cell_angle_beta                 96.414(7)
_cell_angle_gamma                94.215(7)
_cell_volume                     927.83(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4426
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.66

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.460
_exptl_absorpt_coefficient_mu    3.232
_shelx_estimated_absorpt_T_min   0.295
_shelx_estimated_absorpt_T_max   0.318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.295
_exptl_absorpt_correction_T_max  0.318
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd., 2009
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;  
Oxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer 
with Sapphire CCD Detector.
;
_diffrn_measurement_method       
;
Rotation method data acquisition using omega scans.
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5662
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.069
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3363
_reflns_number_gt                2957
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlis CCD (Oxford Diffraction Ltd., 2009)
;
_computing_cell_refinement       
;
CrysAlis RED (Oxford Diffraction Ltd., 2009)
;
_computing_data_reduction        
;
CrysAlis RED (Oxford Diffraction Ltd., 2009)
;
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3363
_refine_ls_number_parameters     310
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0695
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1006(3) 0.6655(2) 0.2611(2) 0.0361(6) Uani 1 1 d . . . . .
C2 C 0.4992(3) 0.8327(2) 0.4028(2) 0.0307(5) Uani 1 1 d . . . . .
C3 C 0.3717(3) 1.1069(2) 0.1561(2) 0.0343(6) Uani 1 1 d . . . . .
C4 C 0.0106(3) 0.7185(2) -0.1116(2) 0.0327(6) Uani 1 1 d . . . . .
N1 N -0.2477(4) 0.5799(3) 0.2250(3) 0.0597(8) Uani 1 1 d D . . . .
H11 H -0.284(5) 0.549(3) 0.1487(18) 0.072 Uiso 1 1 d D U . . .
H12 H -0.276(5) 0.549(3) 0.274(3) 0.072 Uiso 1 1 d D U . . .
N2 N -0.0300(4) 0.7100(3) 0.3770(2) 0.0554(7) Uani 1 1 d D . . . .
H21 H -0.055(5) 0.669(3) 0.418(3) 0.067 Uiso 1 1 d D U . . .
H22 H 0.071(3) 0.755(3) 0.402(3) 0.067 Uiso 1 1 d D U . . .
N3 N 0.5218(4) 0.7640(3) 0.4702(2) 0.0529(7) Uani 1 1 d D . . . .
H31 H 0.438(4) 0.703(3) 0.463(3) 0.064 Uiso 1 1 d D U . . .
H32 H 0.620(3) 0.775(3) 0.513(3) 0.064 Uiso 1 1 d D U . . .
N4 N 0.6349(3) 0.9132(2) 0.4031(2) 0.0468(6) Uani 1 1 d D . . . .
H41 H 0.729(3) 0.917(3) 0.447(3) 0.056 Uiso 1 1 d D U . . .
H42 H 0.618(4) 0.968(3) 0.375(3) 0.056 Uiso 1 1 d D U . . .
N5 N 0.4857(4) 1.2156(3) 0.2076(2) 0.0613(8) Uani 1 1 d D . . . .
H51 H 0.519(5) 1.241(3) 0.2824(18) 0.074 Uiso 1 1 d D U . . .
H52 H 0.506(5) 1.261(3) 0.168(3) 0.074 Uiso 1 1 d D U . . .
N6 N 0.3011(4) 1.0727(2) 0.0415(2) 0.0470(6) Uani 1 1 d D . . . .
H61 H 0.228(4) 1.005(2) 0.007(3) 0.056 Uiso 1 1 d D U . . .
H62 H 0.338(4) 1.109(3) -0.002(3) 0.056 Uiso 1 1 d D U . . .
N7 N 0.0476(4) 0.7235(3) -0.2143(2) 0.0551(7) Uani 1 1 d D . . . .
H71 H -0.020(4) 0.676(3) -0.279(2) 0.066 Uiso 1 1 d D U . . .
H72 H 0.125(4) 0.780(3) -0.214(3) 0.066 Uiso 1 1 d D U . . .
N8 N -0.1084(4) 0.6251(3) -0.1165(3) 0.0584(7) Uani 1 1 d D . . . .
H81 H -0.116(5) 0.625(4) -0.050(2) 0.070 Uiso 1 1 d D U . . .
H82 H -0.159(5) 0.573(3) -0.186(2) 0.070 Uiso 1 1 d D U . . .
N9 N -0.0426(3) 1.0302(2) 0.3066(2) 0.0358(5) Uani 1 1 d . . . . .
N10 N 0.4278(3) 0.6869(2) 0.0448(2) 0.0407(5) Uani 1 1 d . . . . .
N11 N 0.2555(3) 0.4882(2) 0.4777(2) 0.0458(6) Uani 1 1 d . . . . .
O1 O -0.0373(2) 0.70468(17) 0.18674(16) 0.0407(4) Uani 1 1 d . . . . .
O2 O 0.3490(2) 0.82211(17) 0.34044(15) 0.0392(4) Uani 1 1 d . . . . .
O3 O 0.3352(3) 1.04132(17) 0.21678(16) 0.0420(4) Uani 1 1 d . . . . .
O4 O 0.0918(3) 0.80187(17) -0.01138(15) 0.0417(4) Uani 1 1 d . . . . .
O5 O -0.0591(2) 0.97777(18) 0.19210(16) 0.0432(5) Uani 1 1 d . . . . .
O6 O 0.0761(3) 0.99287(18) 0.36496(15) 0.0410(4) Uani 1 1 d . . . . .
O7 O -0.1361(3) 1.11165(18) 0.35843(19) 0.0511(5) Uani 1 1 d . . . . .
O8 O 0.4655(3) 0.80848(18) 0.09854(17) 0.0459(5) Uani 1 1 d . . . . .
O9 O 0.2953(3) 0.63566(17) 0.07143(18) 0.0460(5) Uani 1 1 d . . . . .
O10 O 0.5159(3) 0.6240(2) -0.0313(2) 0.0624(6) Uani 1 1 d . . . . .
O11 O 0.2601(4) 0.5307(2) 0.3969(2) 0.0719(7) Uani 1 1 d . . . . .
O12 O 0.3258(4) 0.5520(2) 0.5838(2) 0.0745(7) Uani 1 1 d . . . . .
O13 O 0.1799(3) 0.3769(2) 0.4503(2) 0.0649(6) Uani 1 1 d . . . . .
Y1 Y 0.18786(3) 0.84596(2) 0.18483(2) 0.02862(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.256(3) . ?
C1 N2 1.315(4) . ?
C1 N1 1.329(4) . ?
C2 O2 1.257(3) . ?
C2 N4 1.316(4) . ?
C2 N3 1.318(3) . ?
C3 O3 1.253(3) . ?
C3 N6 1.312(3) . ?
C3 N5 1.331(3) . ?
C4 O4 1.263(3) . ?
C4 N7 1.311(4) . ?
C4 N8 1.310(4) . ?
N1 H11 0.849(18) . ?
N1 H12 0.827(18) . ?
N2 H21 0.818(18) . ?
N2 H22 0.841(18) . ?
N3 H31 0.871(18) . ?
N3 H32 0.822(18) . ?
N4 H41 0.821(18) . ?
N4 H42 0.819(18) . ?
N5 H51 0.833(18) . ?
N5 H52 0.837(18) . ?
N6 H61 0.838(18) . ?
N6 H62 0.834(18) . ?
N7 H71 0.841(18) . ?
N7 H72 0.829(18) . ?
N8 H81 0.802(18) . ?
N8 H82 0.841(18) . ?
N9 O7 1.219(3) . ?
N9 O5 1.258(3) . ?
N9 O6 1.267(3) . ?
N9 Y1 2.874(2) . ?
N10 O10 1.220(3) . ?
N10 O9 1.248(3) . ?
N10 O8 1.266(3) . ?
N10 Y1 2.859(2) . ?
N11 O12 1.230(3) . ?
N11 O11 1.234(3) . ?
N11 O13 1.243(3) . ?
O1 Y1 2.2477(18) . ?
O2 Y1 2.2232(17) . ?
O3 Y1 2.2639(17) . ?
O4 Y1 2.2309(16) . ?
O5 Y1 2.4541(18) . ?
O6 Y1 2.4515(17) . ?
O8 Y1 2.4323(19) . ?
O9 Y1 2.4899(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 122.1(2) . . ?
O1 C1 N1 120.2(3) . . ?
N2 C1 N1 117.6(3) . . ?
O2 C2 N4 120.7(2) . . ?
O2 C2 N3 120.2(2) . . ?
N4 C2 N3 119.1(2) . . ?
O3 C3 N6 122.3(2) . . ?
O3 C3 N5 120.1(2) . . ?
N6 C3 N5 117.6(3) . . ?
O4 C4 N7 119.5(2) . . ?
O4 C4 N8 121.9(2) . . ?
N7 C4 N8 118.6(3) . . ?
C1 N1 H11 114(3) . . ?
C1 N1 H12 117(3) . . ?
H11 N1 H12 127(4) . . ?
C1 N2 H21 119(2) . . ?
C1 N2 H22 121(2) . . ?
H21 N2 H22 113(4) . . ?
C2 N3 H31 120(2) . . ?
C2 N3 H32 118(2) . . ?
H31 N3 H32 122(3) . . ?
C2 N4 H41 116(2) . . ?
C2 N4 H42 120(2) . . ?
H41 N4 H42 122(3) . . ?
C3 N5 H51 116(3) . . ?
C3 N5 H52 120(2) . . ?
H51 N5 H52 123(4) . . ?
C3 N6 H61 120(2) . . ?
C3 N6 H62 122(2) . . ?
H61 N6 H62 117(3) . . ?
C4 N7 H71 118(2) . . ?
C4 N7 H72 121(2) . . ?
H71 N7 H72 121(3) . . ?
C4 N8 H81 112(3) . . ?
C4 N8 H82 117(2) . . ?
H81 N8 H82 130(4) . . ?
O7 N9 O5 122.0(2) . . ?
O7 N9 O6 121.9(2) . . ?
O5 N9 O6 116.1(2) . . ?
O7 N9 Y1 177.81(17) . . ?
O5 N9 Y1 58.13(12) . . ?
O6 N9 Y1 58.05(11) . . ?
O10 N10 O9 122.1(2) . . ?
O10 N10 O8 120.9(2) . . ?
O9 N10 O8 117.0(2) . . ?
O10 N10 Y1 168.7(2) . . ?
O9 N10 Y1 60.32(12) . . ?
O8 N10 Y1 57.76(12) . . ?
O12 N11 O11 121.9(3) . . ?
O12 N11 O13 119.4(3) . . ?
O11 N11 O13 118.8(2) . . ?
C1 O1 Y1 139.06(17) . . ?
C2 O2 Y1 149.33(17) . . ?
C3 O3 Y1 138.45(15) . . ?
C4 O4 Y1 146.15(17) . . ?
N9 O5 Y1 96.06(14) . . ?
N9 O6 Y1 95.94(13) . . ?
N10 O8 Y1 96.11(15) . . ?
N10 O9 Y1 93.86(14) . . ?
O2 Y1 O4 155.56(7) . . ?
O2 Y1 O1 90.12(7) . . ?
O4 Y1 O1 90.39(7) . . ?
O2 Y1 O3 95.67(7) . . ?
O4 Y1 O3 93.27(6) . . ?
O1 Y1 O3 157.16(7) . . ?
O2 Y1 O8 82.47(7) . . ?
O4 Y1 O8 78.62(7) . . ?
O1 Y1 O8 130.31(6) . . ?
O3 Y1 O8 72.46(7) . . ?
O2 Y1 O6 75.95(6) . . ?
O4 Y1 O6 128.33(7) . . ?
O1 Y1 O6 83.18(7) . . ?
O3 Y1 O6 76.88(7) . . ?
O8 Y1 O6 140.25(6) . . ?
O2 Y1 O5 127.62(6) . . ?
O4 Y1 O5 76.54(6) . . ?
O1 Y1 O5 81.31(7) . . ?
O3 Y1 O5 77.66(7) . . ?
O8 Y1 O5 139.58(7) . . ?
O6 Y1 O5 51.79(6) . . ?
O2 Y1 O9 81.02(7) . . ?
O4 Y1 O9 75.14(7) . . ?
O1 Y1 O9 78.67(7) . . ?
O3 Y1 O9 124.04(7) . . ?
O8 Y1 O9 51.64(6) . . ?
O6 Y1 O9 150.51(7) . . ?
O5 Y1 O9 144.95(6) . . ?
O2 Y1 N10 83.73(7) . . ?
O4 Y1 N10 72.49(7) . . ?
O1 Y1 N10 104.34(7) . . ?
O3 Y1 N10 98.25(7) . . ?
O8 Y1 N10 26.13(6) . . ?
O6 Y1 N10 158.41(7) . . ?
O5 Y1 N10 148.49(6) . . ?
O9 Y1 N10 25.82(6) . . ?
O2 Y1 N9 101.94(7) . . ?
O4 Y1 N9 102.33(7) . . ?
O1 Y1 N9 82.13(6) . . ?
O3 Y1 N9 75.06(7) . . ?
O8 Y1 N9 147.50(6) . . ?
O6 Y1 N9 26.01(6) . . ?
O5 Y1 N9 25.81(6) . . ?
O9 Y1 N9 160.59(6) . . ?
N10 Y1 N9 171.51(6) . . ?

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
N2 C1 O1 Y1 -0.3(4) . . . . ?
N1 C1 O1 Y1 177.1(2) . . . . ?
N4 C2 O2 Y1 21.9(5) . . . . ?
N3 C2 O2 Y1 -158.9(3) . . . . ?
N6 C3 O3 Y1 8.9(4) . . . . ?
N5 C3 O3 Y1 -171.1(2) . . . . ?
N7 C4 O4 Y1 -153.4(3) . . . . ?
N8 C4 O4 Y1 25.6(5) . . . . ?
O7 N9 O5 Y1 177.4(2) . . . . ?
O6 N9 O5 Y1 -3.0(2) . . . . ?
O7 N9 O6 Y1 -177.4(2) . . . . ?
O5 N9 O6 Y1 3.0(2) . . . . ?
O10 N10 O8 Y1 166.8(2) . . . . ?
O9 N10 O8 Y1 -11.7(2) . . . . ?
O10 N10 O9 Y1 -167.1(2) . . . . ?
O8 N10 O9 Y1 11.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H11 O10 0.849(18) 2.39(3) 2.997(4) 129(3) 2_565
N1 H12 O12 0.827(18) 2.425(19) 3.247(4) 173(3) 2_566
N2 H21 O13 0.818(18) 2.12(2) 2.899(3) 158(3) 2_566
N2 H22 O2 0.841(18) 2.46(3) 3.181(3) 145(3) .
N3 H31 O11 0.871(18) 2.10(2) 2.944(4) 164(3) .
N3 H32 O13 0.822(18) 2.49(3) 3.110(4) 133(3) 2_666
N4 H41 O6 0.821(18) 2.36(2) 3.110(3) 152(3) 2_676
N4 H42 O7 0.819(18) 2.45(3) 2.967(3) 122(3) 1_655
N5 H51 O12 0.833(18) 2.39(3) 2.970(3) 127(3) 2_676
N5 H52 O10 0.837(18) 2.44(2) 3.256(4) 165(3) 2_675
N6 H61 O4 0.838(18) 2.36(2) 3.129(3) 153(3) .
N6 H62 O8 0.834(18) 2.32(2) 3.117(3) 160(3) 2_675
N7 H71 O13 0.841(18) 2.11(2) 2.903(3) 158(3) 2_565
N7 H72 O7 0.829(18) 2.47(3) 3.062(3) 129(3) 2_575
N8 H82 O11 0.841(18) 2.35(2) 3.170(4) 164(3) 2_565

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.056

_shelxl_version_number           2014/6

