# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_aaa
_database_code_depnum_ccdc_archive 'CCDC 1475480'
_audit_update_record             
;
2016-04-21 deposited with the CCDC.
2017-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C9 H4 N2 O4 Y0.33'
_chemical_formula_sum            'C9 H4 N2 O4 Y0.33'
_chemical_formula_weight         233.78

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'

# 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 -0.021 -0.019 -0.050 1189 170 ' '
_platon_squeeze_details          
;
The Platon SQUEEZE procedure was applied to recover 28 electrons
per formula unit. Lattice solvent water molecules (10 electrons/H2O) were present, and the electrons recovered by SQUEEZE have been assigned as 3 water molecules per formula unit. These water molecules have been included in the formula.
;


_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   P31c
_symmetry_space_group_name_Hall  P3-2c

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

_cell_length_a                   12.8501(18)
_cell_length_b                   12.8501(18)
_cell_length_c                   15.709(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2246.4(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3428
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.037
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             702
_exptl_absorpt_coefficient_mu    1.347
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_T_max  0.722
_exptl_absorpt_process_details   Process-auto

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21210
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3428
_reflns_number_gt                3261
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Process-auto
_computing_cell_refinement       Process-auto
_computing_data_reduction        Process-auto
_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)+(0.0532P)²+0.2118P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.005(6)
_refine_ls_number_reflns         3428
_refine_ls_number_parameters     139
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.083
_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
Y1 Y 0.6667 0.3333 0.03335(3) 0.01574(10) Uani 1 3 d S . .
C1 C 1.0563(2) 0.9396(2) -0.23005(17) 0.0240(5) Uani 1 1 d . . .
C2 C 1.0705(2) 0.7547(2) -0.22153(18) 0.0263(6) Uani 1 1 d . . .
C3 C 1.1052(2) 0.6924(2) -0.27721(17) 0.0258(5) Uani 1 1 d . . .
H3A H 1.1572 0.7325 -0.3221 0.031 Uiso 1 1 calc R . .
C4 C 1.0617(2) 0.5704(2) -0.26512(16) 0.0250(5) Uani 1 1 d . . .
C5 C 0.9838(2) 0.5108(2) -0.19781(17) 0.0298(6) Uani 1 1 d . . .
H5A H 0.9536 0.4288 -0.1905 0.036 Uiso 1 1 calc R . .
C6 C 0.9505(3) 0.5726(3) -0.14131(18) 0.0283(6) Uani 1 1 d . . .
C7 C 0.9957(3) 0.6951(2) -0.15291(18) 0.0292(6) Uani 1 1 d . . .
H7A H 0.9758 0.7374 -0.1145 0.035 Uiso 1 1 calc R . .
C8 C 0.8666(3) 0.5053(3) -0.06927(18) 0.0323(6) Uani 1 1 d . . .
N1 N 0.9355(2) 0.8749(2) -0.22975(16) 0.0298(5) Uani 1 1 d . . .
N2 N 1.11875(19) 0.88036(19) -0.23269(15) 0.0318(5) Uani 1 1 d . . .
H2A H 1.1947 0.9228 -0.2420 0.038 Uiso 1 1 calc R . .
O1 O 0.81993(19) 0.39300(19) -0.06917(13) 0.0426(6) Uani 1 1 d . . .
O2 O 0.8464(2) 0.5596(2) -0.01225(13) 0.0408(5) Uani 1 1 d . . .
C9 C 1.0954(2) 0.5001(2) -0.32528(16) 0.0235(5) Uani 1 1 d . . .
O3 O 1.17839(18) 0.55760(18) -0.37736(11) 0.0309(4) Uani 1 1 d . . .
O4 O 1.03828(19) 0.38804(18) -0.32008(15) 0.0358(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Y1 0.01740(12) 0.01740(12) 0.01243(15) 0.000 0.000 0.00870(6)
C1 0.0194(12) 0.0212(12) 0.0344(14) 0.0009(11) 0.0042(10) 0.0123(10)
C2 0.0201(11) 0.0203(12) 0.0393(15) 0.0026(10) 0.0069(11) 0.0108(10)
C3 0.0233(12) 0.0212(11) 0.0331(13) 0.0078(10) 0.0128(11) 0.0112(10)
C4 0.0272(13) 0.0235(12) 0.0261(12) 0.0030(10) 0.0083(10) 0.0140(10)
C5 0.0315(14) 0.0239(12) 0.0338(15) 0.0073(12) 0.0130(12) 0.0138(11)
C6 0.0293(13) 0.0278(14) 0.0299(14) 0.0055(11) 0.0112(11) 0.0158(12)
C7 0.0310(14) 0.0288(13) 0.0323(14) 0.0004(12) 0.0115(12) 0.0182(12)
C8 0.0261(14) 0.0431(17) 0.0296(15) 0.0091(13) 0.0114(12) 0.0189(13)
N1 0.0202(11) 0.0237(11) 0.0439(14) -0.0049(10) 0.0001(10) 0.0098(9)
N2 0.0188(10) 0.0203(10) 0.0563(16) 0.0054(10) 0.0122(10) 0.0098(8)
O1 0.0367(12) 0.0360(12) 0.0474(13) 0.0137(10) 0.0250(10) 0.0124(10)
O2 0.0419(12) 0.0531(14) 0.0334(11) 0.0013(9) 0.0140(9) 0.0284(11)
C9 0.0227(12) 0.0272(13) 0.0237(11) 0.0071(10) 0.0079(10) 0.0149(10)
O3 0.0350(11) 0.0324(11) 0.0287(10) 0.0067(9) 0.0140(9) 0.0195(9)
O4 0.0396(12) 0.0221(10) 0.0459(13) -0.0002(9) 0.0119(10) 0.0156(9)

_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
Y1 O3 2.2595(19) 6_765 ?
Y1 O3 2.2595(19) 4_545 ?
Y1 O3 2.2595(19) 5_565 ?
Y1 O1 2.3559(19) . ?
Y1 O1 2.3559(19) 3_665 ?
Y1 O1 2.3559(19) 2_655 ?
Y1 O2 2.754(2) 3_665 ?
Y1 O2 2.754(2) . ?
Y1 O2 2.754(2) 2_655 ?
Y1 C8 2.899(3) 3_665 ?
Y1 C8 2.899(3) . ?
Y1 C8 2.899(3) 2_655 ?
C1 N1 1.346(4) . ?
C1 N1 1.351(4) 2_765 ?
C1 N2 1.355(3) . ?
C2 C7 1.391(4) . ?
C2 C3 1.401(4) . ?
C2 N2 1.422(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.393(3) . ?
C4 C9 1.513(3) . ?
C5 C6 1.393(4) . ?
C6 C7 1.390(4) . ?
C6 C8 1.503(4) . ?
C8 O2 1.239(4) . ?
C8 O1 1.256(4) . ?
N1 C1 1.351(4) 3_675 ?
C9 O4 1.250(3) . ?
C9 O3 1.251(3) . ?
O3 Y1 2.2595(19) 4_654 ?

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
O3 Y1 O3 85.52(8) 6_765 4_545 ?
O3 Y1 O3 85.52(8) 6_765 5_565 ?
O3 Y1 O3 85.52(8) 4_545 5_565 ?
O3 Y1 O1 81.68(7) 6_765 . ?
O3 Y1 O1 139.50(8) 4_545 . ?
O3 Y1 O1 131.10(8) 5_565 . ?
O3 Y1 O1 131.10(8) 6_765 3_665 ?
O3 Y1 O1 81.68(7) 4_545 3_665 ?
O3 Y1 O1 139.50(8) 5_565 3_665 ?
O1 Y1 O1 78.40(9) . 3_665 ?
O3 Y1 O1 139.50(8) 6_765 2_655 ?
O3 Y1 O1 131.10(8) 4_545 2_655 ?
O3 Y1 O1 81.68(7) 5_565 2_655 ?
O1 Y1 O1 78.40(9) . 2_655 ?
O1 Y1 O1 78.40(9) 3_665 2_655 ?
O3 Y1 O2 81.25(7) 6_765 3_665 ?
O3 Y1 O2 73.83(7) 4_545 3_665 ?
O3 Y1 O2 156.20(7) 5_565 3_665 ?
O1 Y1 O2 66.34(7) . 3_665 ?
O1 Y1 O2 49.85(7) 3_665 3_665 ?
O1 Y1 O2 120.85(7) 2_655 3_665 ?
O3 Y1 O2 73.83(7) 6_765 . ?
O3 Y1 O2 156.20(7) 4_545 . ?
O3 Y1 O2 81.25(7) 5_565 . ?
O1 Y1 O2 49.85(7) . . ?
O1 Y1 O2 120.85(7) 3_665 . ?
O1 Y1 O2 66.34(7) 2_655 . ?
O2 Y1 O2 113.49(4) 3_665 . ?
O3 Y1 O2 156.20(7) 6_765 2_655 ?
O3 Y1 O2 81.25(7) 4_545 2_655 ?
O3 Y1 O2 73.83(7) 5_565 2_655 ?
O1 Y1 O2 120.85(7) . 2_655 ?
O1 Y1 O2 66.34(7) 3_665 2_655 ?
O1 Y1 O2 49.85(7) 2_655 2_655 ?
O2 Y1 O2 113.49(4) 3_665 2_655 ?
O2 Y1 O2 113.49(4) . 2_655 ?
O3 Y1 C8 106.20(8) 6_765 3_665 ?
O3 Y1 C8 79.45(8) 4_545 3_665 ?
O3 Y1 C8 160.00(8) 5_565 3_665 ?
O1 Y1 C8 67.75(8) . 3_665 ?
O1 Y1 C8 25.02(8) 3_665 3_665 ?
O1 Y1 C8 98.31(8) 2_655 3_665 ?
O2 Y1 C8 25.16(7) 3_665 3_665 ?
O2 Y1 C8 117.24(7) . 3_665 ?
O2 Y1 C8 90.78(8) 2_655 3_665 ?
O3 Y1 C8 79.45(8) 6_765 . ?
O3 Y1 C8 160.00(8) 4_545 . ?
O3 Y1 C8 106.20(8) 5_565 . ?
O1 Y1 C8 25.02(8) . . ?
O1 Y1 C8 98.31(8) 3_665 . ?
O1 Y1 C8 67.75(8) 2_655 . ?
O2 Y1 C8 90.78(8) 3_665 . ?
O2 Y1 C8 25.16(7) . . ?
O2 Y1 C8 117.24(7) 2_655 . ?
C8 Y1 C8 92.08(8) 3_665 . ?
O3 Y1 C8 160.00(8) 6_765 2_655 ?
O3 Y1 C8 106.20(8) 4_545 2_655 ?
O3 Y1 C8 79.45(8) 5_565 2_655 ?
O1 Y1 C8 98.31(8) . 2_655 ?
O1 Y1 C8 67.75(8) 3_665 2_655 ?
O1 Y1 C8 25.02(8) 2_655 2_655 ?
O2 Y1 C8 117.24(7) 3_665 2_655 ?
O2 Y1 C8 90.78(8) . 2_655 ?
O2 Y1 C8 25.16(7) 2_655 2_655 ?
C8 Y1 C8 92.08(8) 3_665 2_655 ?
C8 Y1 C8 92.08(8) . 2_655 ?
N1 C1 N1 126.9(3) . 2_765 ?
N1 C1 N2 118.5(2) . . ?
N1 C1 N2 114.6(2) 2_765 . ?
C7 C2 C3 119.9(2) . . ?
C7 C2 N2 120.7(2) . . ?
C3 C2 N2 119.3(2) . . ?
C4 C3 C2 119.7(2) . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 C9 121.0(2) . . ?
C5 C4 C9 119.1(2) . . ?
C4 C5 C6 120.7(2) . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 C8 121.6(3) . . ?
C5 C6 C8 119.2(3) . . ?
C6 C7 C2 120.5(2) . . ?
O2 C8 O1 122.1(3) . . ?
O2 C8 C6 120.8(3) . . ?
O1 C8 C6 117.1(3) . . ?
O2 C8 Y1 70.86(16) . . ?
O1 C8 Y1 52.51(14) . . ?
C6 C8 Y1 164.7(2) . . ?
C1 N1 C1 113.1(3) . 3_675 ?
C1 N2 C2 126.1(2) . . ?
C8 O1 Y1 102.47(17) . . ?
C8 O2 Y1 83.97(18) . . ?
O4 C9 O3 124.0(2) . . ?
O4 C9 C4 118.0(2) . . ?
O3 C9 C4 118.0(2) . . ?
C9 O3 Y1 177.47(19) . 4_654 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.058
