# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 1569059'
_audit_update_record             
;
2018-01-17 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H9 N13 O12'
_chemical_formula_weight         479.28

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           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   29.746(6)
_cell_length_b                   7.8121(16)
_cell_length_c                   19.757(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 130.51(3)
_cell_angle_gamma                90.00
_cell_volume                     3490.6(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11125
_cell_measurement_theta_min      3.205
_cell_measurement_theta_max      27.555

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1952
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9587
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_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 r-axis rapid IP'
_diffrn_measurement_method       oscillation
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13800
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         25.49
_reflns_number_total             3240
_reflns_number_gt                2714
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'

_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)+(0.1000P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0087(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3240
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1350
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.094
_refine_ls_shift/su_mean         0.010

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 -0.02944(6) -0.12233(18) 0.15242(9) 0.0512(4) Uani 1 1 d . . .
O2 O -0.03424(6) 0.15248(18) 0.14039(10) 0.0565(4) Uani 1 1 d . . .
O3 O 0.08534(8) 0.0994(2) 0.04631(10) 0.0709(5) Uani 1 1 d . . .
O4 O 0.01157(7) 0.1855(2) 0.03694(9) 0.0669(5) Uani 1 1 d . . .
O5 O 0.17075(6) -0.0376(2) 0.49184(8) 0.0529(4) Uani 1 1 d . . .
O6 O 0.18392(7) 0.23122(19) 0.48100(8) 0.0607(5) Uani 1 1 d . . .
O7 O 0.26291(6) -0.10476(18) 0.47032(8) 0.0525(4) Uani 1 1 d . . .
O8 O 0.27923(6) -0.1066(3) 0.37797(10) 0.0702(5) Uani 1 1 d . . .
O9 O 0.05699(7) -0.41091(19) 0.13695(10) 0.0617(5) Uani 1 1 d . . .
O10 O 0.13162(8) -0.3769(2) 0.14299(12) 0.0738(5) Uani 1 1 d . . .
O11 O 0.20524(7) 0.47175(18) 0.34973(10) 0.0576(4) Uani 1 1 d . . .
O12 O 0.24162(8) 0.3656(2) 0.29445(11) 0.0679(5) Uani 1 1 d . . .
C1 C 0.08560(7) -0.1327(2) 0.23701(10) 0.0331(4) Uani 1 1 d . . .
H1A H 0.0626 -0.2306 0.2309 0.040 Uiso 1 1 calc R . .
C2 C 0.14419(7) -0.1103(2) 0.33611(10) 0.0325(4) Uani 1 1 d . . .
H2A H 0.1471 -0.1967 0.3747 0.039 Uiso 1 1 calc R . .
C3 C 0.08002(7) 0.1809(2) 0.21573(10) 0.0339(4) Uani 1 1 d . . .
H3A H 0.0541 0.2793 0.1983 0.041 Uiso 1 1 calc R . .
C4 C 0.14015(7) 0.2002(2) 0.31393(10) 0.0316(4) Uani 1 1 d . . .
H4A H 0.1414 0.3093 0.3396 0.038 Uiso 1 1 calc R . .
C5 C 0.16457(7) -0.0916(2) 0.23672(10) 0.0373(4) Uani 1 1 d . . .
H5A H 0.1862 -0.1478 0.2210 0.045 Uiso 1 1 calc R . .
C6 C 0.16174(8) 0.1088(2) 0.22336(11) 0.0362(4) Uani 1 1 d . . .
H6A H 0.1821 0.1432 0.2017 0.043 Uiso 1 1 calc R . .
N13 N 0.07752(10) 0.5250(2) 0.31805(13) 0.0637(5) Uani 1 1 d . . .
N1 N 0.05183(6) 0.02308(18) 0.20804(9) 0.0373(4) Uani 1 1 d . . .
N2 N 0.10211(6) 0.17912(18) 0.16783(9) 0.0380(4) Uani 1 1 d . . .
N3 N 0.14542(6) 0.05957(18) 0.36517(8) 0.0341(3) Uani 1 1 d . . .
N4 N 0.18808(6) -0.14083(19) 0.32616(9) 0.0349(4) Uani 1 1 d . . .
N5 N 0.10476(6) -0.15878(18) 0.18469(9) 0.0361(4) Uani 1 1 d . . .
N6 N 0.18734(6) 0.19355(18) 0.30810(8) 0.0338(3) Uani 1 1 d . . .
N7 N -0.00833(6) 0.01666(19) 0.16265(9) 0.0363(4) Uani 1 1 d . . .
N8 N 0.06310(8) 0.1504(2) 0.07668(10) 0.0495(5) Uani 1 1 d . . .
N9 N 0.16930(6) 0.0861(2) 0.45326(9) 0.0399(4) Uani 1 1 d . . .
N10 N 0.24797(7) -0.1145(2) 0.39711(10) 0.0433(4) Uani 1 1 d . . .
N11 N 0.09794(8) -0.3314(2) 0.15387(10) 0.0463(4) Uani 1 1 d . . .
N12 N 0.21273(7) 0.3586(2) 0.31704(9) 0.0425(4) Uani 1 1 d . . .
C8 C 0.07964(9) 0.5206(2) 0.37773(13) 0.0462(5) Uani 1 1 d . . .
C7 C 0.08299(13) 0.5140(4) 0.45340(17) 0.0597(6) Uani 1 1 d . . .
H7A H 0.1089(15) 0.451(4) 0.492(2) 0.093(11) Uiso 1 1 d . . .
H7B H 0.048(2) 0.485(6) 0.437(3) 0.141(15) Uiso 1 1 d . . .
H7C H 0.0977(14) 0.607(4) 0.478(2) 0.087(10) 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 N7 1.204(2) . ?
O2 N7 1.214(2) . ?
O3 N8 1.213(2) . ?
O4 N8 1.216(2) . ?
O5 N9 1.214(2) . ?
O6 N9 1.210(2) . ?
O7 N10 1.209(2) . ?
O8 N10 1.212(2) . ?
O9 N11 1.205(2) . ?
O10 N11 1.206(2) . ?
O11 N12 1.198(2) . ?
O12 N12 1.200(2) . ?
C1 N1 1.439(2) . ?
C1 N5 1.483(2) . ?
C1 C2 1.571(2) . ?
C1 H1A 0.9800 . ?
C2 N3 1.437(2) . ?
C2 N4 1.461(2) . ?
C2 H2A 0.9800 . ?
C3 N1 1.442(2) . ?
C3 N2 1.461(2) . ?
C3 C4 1.574(2) . ?
C3 H3A 0.9800 . ?
C4 N3 1.432(2) . ?
C4 N6 1.482(2) . ?
C4 H4A 0.9800 . ?
C5 N5 1.457(2) . ?
C5 N4 1.468(2) . ?
C5 C6 1.580(3) . ?
C5 H5A 0.9800 . ?
C6 N2 1.457(2) . ?
C6 N6 1.471(2) . ?
C6 H6A 0.9800 . ?
N13 C8 1.139(3) . ?
N1 N7 1.387(2) . ?
N2 N8 1.388(2) . ?
N3 N9 1.404(2) . ?
N4 N10 1.391(2) . ?
N5 N11 1.439(2) . ?
N6 N12 1.446(2) . ?
C8 C7 1.433(3) . ?
C7 H7A 0.80(3) . ?
C7 H7B 0.90(5) . ?
C7 H7C 0.82(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
N1 C1 N5 108.91(13) . . ?
N1 C1 C2 108.92(13) . . ?
N5 C1 C2 105.45(13) . . ?
N1 C1 H1A 111.1 . . ?
N5 C1 H1A 111.1 . . ?
C2 C1 H1A 111.1 . . ?
N3 C2 N4 114.32(13) . . ?
N3 C2 C1 108.69(12) . . ?
N4 C2 C1 100.32(12) . . ?
N3 C2 H2A 111.0 . . ?
N4 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
N1 C3 N2 113.52(14) . . ?
N1 C3 C4 109.23(12) . . ?
N2 C3 C4 99.80(13) . . ?
N1 C3 H3A 111.3 . . ?
N2 C3 H3A 111.3 . . ?
C4 C3 H3A 111.3 . . ?
N3 C4 N6 110.71(13) . . ?
N3 C4 C3 108.21(13) . . ?
N6 C4 C3 106.02(13) . . ?
N3 C4 H4A 110.6 . . ?
N6 C4 H4A 110.6 . . ?
C3 C4 H4A 110.6 . . ?
N5 C5 N4 99.41(14) . . ?
N5 C5 C6 109.32(14) . . ?
N4 C5 C6 113.12(13) . . ?
N5 C5 H5A 111.5 . . ?
N4 C5 H5A 111.5 . . ?
C6 C5 H5A 111.5 . . ?
N2 C6 N6 99.45(14) . . ?
N2 C6 C5 113.95(14) . . ?
N6 C6 C5 108.89(13) . . ?
N2 C6 H6A 111.3 . . ?
N6 C6 H6A 111.3 . . ?
C5 C6 H6A 111.3 . . ?
N7 N1 C1 120.05(13) . . ?
N7 N1 C3 121.10(13) . . ?
C1 N1 C3 118.22(14) . . ?
N8 N2 C6 119.92(16) . . ?
N8 N2 C3 119.56(14) . . ?
C6 N2 C3 110.81(13) . . ?
N9 N3 C4 119.87(13) . . ?
N9 N3 C2 119.53(13) . . ?
C4 N3 C2 117.61(13) . . ?
N10 N4 C5 118.11(15) . . ?
N10 N4 C2 120.77(14) . . ?
C5 N4 C2 110.53(13) . . ?
N11 N5 C5 114.09(14) . . ?
N11 N5 C1 114.30(14) . . ?
C5 N5 C1 107.74(12) . . ?
N12 N6 C6 112.56(13) . . ?
N12 N6 C4 113.88(13) . . ?
C6 N6 C4 106.74(13) . . ?
O1 N7 O2 126.07(15) . . ?
O1 N7 N1 117.01(14) . . ?
O2 N7 N1 116.84(14) . . ?
O3 N8 O4 128.21(17) . . ?
O3 N8 N2 115.48(17) . . ?
O4 N8 N2 116.24(19) . . ?
O6 N9 O5 127.25(15) . . ?
O6 N9 N3 116.32(15) . . ?
O5 N9 N3 116.36(15) . . ?
O7 N10 O8 127.60(16) . . ?
O7 N10 N4 116.74(16) . . ?
O8 N10 N4 115.65(15) . . ?
O9 N11 O10 127.28(17) . . ?
O9 N11 N5 116.07(17) . . ?
O10 N11 N5 116.50(17) . . ?
O11 N12 O12 126.62(17) . . ?
O11 N12 N6 117.30(16) . . ?
O12 N12 N6 115.99(17) . . ?
N13 C8 C7 179.3(2) . . ?
C8 C7 H7A 112(2) . . ?
C8 C7 H7B 111(3) . . ?
H7A C7 H7B 112(4) . . ?
C8 C7 H7C 103(2) . . ?
H7A C7 H7C 100(3) . . ?
H7B C7 H7C 119(4) . . ?

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
N1 C1 C2 N3 -0.87(18) . . . . ?
N5 C1 C2 N3 115.89(14) . . . . ?
N1 C1 C2 N4 -121.10(14) . . . . ?
N5 C1 C2 N4 -4.34(15) . . . . ?
N1 C3 C4 N3 -3.63(18) . . . . ?
N2 C3 C4 N3 -122.92(14) . . . . ?
N1 C3 C4 N6 115.18(15) . . . . ?
N2 C3 C4 N6 -4.11(15) . . . . ?
N5 C5 C6 N2 3.10(19) . . . . ?
N4 C5 C6 N2 -106.66(16) . . . . ?
N5 C5 C6 N6 113.09(15) . . . . ?
N4 C5 C6 N6 3.34(19) . . . . ?
N5 C1 N1 N7 111.53(16) . . . . ?
C2 C1 N1 N7 -133.95(15) . . . . ?
N5 C1 N1 C3 -59.54(18) . . . . ?
C2 C1 N1 C3 54.99(19) . . . . ?
N2 C3 N1 N7 -113.16(17) . . . . ?
C4 C3 N1 N7 136.45(15) . . . . ?
N2 C3 N1 C1 57.81(18) . . . . ?
C4 C3 N1 C1 -52.59(19) . . . . ?
N6 C6 N2 N8 171.76(13) . . . . ?
C5 C6 N2 N8 -72.58(19) . . . . ?
N6 C6 N2 C3 -42.36(16) . . . . ?
C5 C6 N2 C3 73.30(17) . . . . ?
N1 C3 N2 N8 59.00(19) . . . . ?
C4 C3 N2 N8 175.09(14) . . . . ?
N1 C3 N2 C6 -87.01(16) . . . . ?
C4 C3 N2 C6 29.08(16) . . . . ?
N6 C4 N3 N9 103.07(16) . . . . ?
C3 C4 N3 N9 -141.14(14) . . . . ?
N6 C4 N3 C2 -57.29(18) . . . . ?
C3 C4 N3 C2 58.50(18) . . . . ?
N4 C2 N3 N9 -105.46(16) . . . . ?
C1 C2 N3 N9 143.42(14) . . . . ?
N4 C2 N3 C4 54.97(19) . . . . ?
C1 C2 N3 C4 -56.16(18) . . . . ?
N5 C5 N4 N10 173.51(13) . . . . ?
C6 C5 N4 N10 -70.68(19) . . . . ?
N5 C5 N4 C2 -41.47(17) . . . . ?
C6 C5 N4 C2 74.34(17) . . . . ?
N3 C2 N4 N10 56.4(2) . . . . ?
C1 C2 N4 N10 172.50(13) . . . . ?
N3 C2 N4 C5 -87.53(16) . . . . ?
C1 C2 N4 C5 28.55(16) . . . . ?
N4 C5 N5 N11 -91.47(15) . . . . ?
C6 C5 N5 N11 149.86(14) . . . . ?
N4 C5 N5 C1 36.58(16) . . . . ?
C6 C5 N5 C1 -82.09(16) . . . . ?
N1 C1 N5 N11 -136.06(14) . . . . ?
C2 C1 N5 N11 107.17(14) . . . . ?
N1 C1 N5 C5 96.01(15) . . . . ?
C2 C1 N5 C5 -20.76(16) . . . . ?
N2 C6 N6 N12 -88.51(15) . . . . ?
C5 C6 N6 N12 152.02(14) . . . . ?
N2 C6 N6 C4 37.13(15) . . . . ?
C5 C6 N6 C4 -82.33(16) . . . . ?
N3 C4 N6 N12 -139.06(13) . . . . ?
C3 C4 N6 N12 103.80(13) . . . . ?
N3 C4 N6 C6 96.10(15) . . . . ?
C3 C4 N6 C6 -21.04(16) . . . . ?
C1 N1 N7 O1 2.8(2) . . . . ?
C3 N1 N7 O1 173.58(15) . . . . ?
C1 N1 N7 O2 179.67(15) . . . . ?
C3 N1 N7 O2 -9.5(2) . . . . ?
C6 N2 N8 O3 -15.5(2) . . . . ?
C3 N2 N8 O3 -158.39(17) . . . . ?
C6 N2 N8 O4 167.28(16) . . . . ?
C3 N2 N8 O4 24.4(2) . . . . ?
C4 N3 N9 O6 0.7(2) . . . . ?
C2 N3 N9 O6 160.64(15) . . . . ?
C4 N3 N9 O5 177.76(15) . . . . ?
C2 N3 N9 O5 -22.3(2) . . . . ?
C5 N4 N10 O7 157.86(15) . . . . ?
C2 N4 N10 O7 16.5(2) . . . . ?
C5 N4 N10 O8 -23.2(2) . . . . ?
C2 N4 N10 O8 -164.48(17) . . . . ?
C5 N5 N11 O9 156.73(15) . . . . ?
C1 N5 N11 O9 32.1(2) . . . . ?
C5 N5 N11 O10 -27.4(2) . . . . ?
C1 N5 N11 O10 -152.03(16) . . . . ?
C6 N6 N12 O11 140.10(16) . . . . ?
C4 N6 N12 O11 18.4(2) . . . . ?
C6 N6 N12 O12 -43.2(2) . . . . ?
C4 N6 N12 O12 -164.90(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
