# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1919565'
loop_
_audit_author_name
_audit_author_address
'Shiliang Huang'
;China Academy of Engineering Physics
China
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2019-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H10 N16 O16'
_chemical_formula_weight         586.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.537(4)
_cell_length_b                   10.001(4)
_cell_length_c                   12.295(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.96(3)
_cell_angle_gamma                90
_cell_volume                     2002.6(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    749
_cell_measurement_theta_min      5.4110
_cell_measurement_theta_max      66.4470

_exptl_crystal_description       prism
_exptl_crystal_colour            cololess
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.945
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.669
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_T_min  0.38217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.9f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9795
_diffrn_reflns_av_unetI/netI     0.4098
_diffrn_reflns_av_R_equivalents  0.4311
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.190
_diffrn_reflns_theta_max         63.679
_diffrn_reflns_theta_full        63.679
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3220
_reflns_number_gt                875
_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       'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2500P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3220
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3876
_refine_ls_R_factor_gt           0.1668
_refine_ls_wR_factor_ref         0.5023
_refine_ls_wR_factor_gt          0.3910
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
O3 O 0.4500(9) 0.7806(15) 0.2081(11) 0.077(4) Uiso 1 1 d . . . . .
O4 O 0.4932(10) 0.6058(15) 0.3128(12) 0.085(5) Uiso 1 1 d . . . . .
O5 O 0.2970(9) 0.3113(13) 0.3505(10) 0.070(4) Uiso 1 1 d . . . . .
O6 O 0.1839(9) 0.4167(13) 0.3041(10) 0.065(4) Uiso 1 1 d . . . . .
O7 O 0.1824(8) 0.1481(12) 0.0366(9) 0.059(3) Uiso 1 1 d . . . . .
O8 O 0.3057(10) 0.0951(15) 0.1114(11) 0.083(4) Uiso 1 1 d . . . . .
O9 O 0.0696(8) 0.4070(12) 0.0449(9) 0.058(3) Uiso 1 1 d . . . . .
O10 O 0.0817(9) 0.5846(14) 0.1450(11) 0.070(4) Uiso 1 1 d . . . . .
O11 O 0.3052(9) 0.6812(13) -0.1708(11) 0.070(4) Uiso 1 1 d . . . . .
O12 O 0.3423(8) 0.8197(13) -0.0363(10) 0.063(4) Uiso 1 1 d . . . . .
O13 O 0.1535(9) 0.8381(13) -0.0705(11) 0.074(4) Uiso 1 1 d . . . . .
O14 O 0.1671(8) 0.8570(12) 0.1080(10) 0.060(3) Uiso 1 1 d . . . . .
O15 O 0.0920(8) 0.9212(13) 0.3126(10) 0.066(4) Uiso 1 1 d . . . . .
O16 O 0.0992(8) 1.1344(13) 0.2867(10) 0.064(4) Uiso 1 1 d . . . . .
N1 N 0.3658(9) 0.4068(13) 0.0114(10) 0.044(4) Uiso 1 1 d . . . . .
N3 N 0.3913(9) 0.5820(14) 0.1670(11) 0.047(4) Uiso 1 1 d . . . . .
N4 N 0.4498(11) 0.6686(17) 0.2370(13) 0.065(5) Uiso 1 1 d . . . . .
N5 N 0.2957(9) 0.4952(13) 0.2496(10) 0.044(4) Uiso 1 1 d . . . . .
N6 N 0.2554(11) 0.4043(15) 0.3029(12) 0.055(4) Uiso 1 1 d . . . . .
N7 N 0.2720(8) 0.3106(12) 0.0993(9) 0.036(3) Uiso 1 1 d . . . . .
N8 N 0.2523(11) 0.1774(16) 0.0795(12) 0.058(4) Uiso 1 1 d . . . . .
N9 N 0.1919(8) 0.5102(12) 0.0846(9) 0.037(3) Uiso 1 1 d . . . . .
N10 N 0.1089(10) 0.4985(15) 0.0940(12) 0.056(4) Uiso 1 1 d . . . . .
N11 N 0.3001(8) 0.6173(12) -0.0012(9) 0.037(3) Uiso 1 1 d . . . . .
N12 N 0.3187(10) 0.7196(16) -0.0736(12) 0.056(4) Uiso 1 1 d . . . . .
N13 N 0.0463(9) 0.8825(13) 0.0045(10) 0.042(4) Uiso 1 1 d . . . . .
N14 N 0.1267(10) 0.8535(15) 0.0133(12) 0.057(4) Uiso 1 1 d . . . . .
N15 N 0.0210(8) 1.0121(11) 0.1601(9) 0.032(3) Uiso 1 1 d . . . . .
N16 N 0.0754(10) 1.0266(16) 0.2580(12) 0.055(4) Uiso 1 1 d . . . . .
C1 C 0.2930(10) 0.4797(15) -0.0351(12) 0.036(4) Uiso 1 1 d . . . . .
H1 H 0.280386 0.470810 -0.115635 0.044 Uiso 1 1 calc R U . . .
C2 C 0.2257(11) 0.4114(17) 0.0225(13) 0.048(5) Uiso 1 1 d . . . . .
H2 H 0.183023 0.368751 -0.031681 0.057 Uiso 1 1 calc R U . . .
C3 C 0.3590(11) 0.3444(18) 0.1171(13) 0.049(5) Uiso 1 1 d . . . . .
H3 H 0.394920 0.266581 0.134543 0.059 Uiso 1 1 calc R U . . .
C4 C 0.3724(12) 0.4602(17) 0.2153(14) 0.052(5) Uiso 1 1 d . . . . .
H4 H 0.414614 0.434505 0.277920 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3134(10) 0.6479(17) 0.1152(12) 0.041(4) Uiso 1 1 d . . . . .
H5 H 0.315806 0.744676 0.127805 0.049 Uiso 1 1 calc R U . . .
C6 C 0.2456(10) 0.5824(15) 0.1697(11) 0.034(4) Uiso 1 1 d . . . . .
H6 H 0.215570 0.648709 0.205916 0.041 Uiso 1 1 calc R U . . .
C7 C -0.0051(10) 0.8585(15) -0.1031(11) 0.038(4) Uiso 1 1 d . . . . .
H7A H -0.056461 0.817299 -0.093447 0.046 Uiso 1 1 calc R U . . .
H7B H 0.022801 0.798650 -0.146569 0.046 Uiso 1 1 calc R U . . .
C8 C 0.0110(10) 0.8847(14) 0.1069(11) 0.037(4) Uiso 1 1 d . . . . .
H8A H -0.046996 0.863233 0.089450 0.045 Uiso 1 1 calc R U . . .
H8B H 0.037574 0.816769 0.157106 0.045 Uiso 1 1 calc R U . . .
N2A N 0.423(3) 0.350(5) -0.059(4) 0.103(15) Uiso 0.5 1 d . . P A 1
O1A O 0.4030(17) 0.400(3) -0.150(2) 0.065(7) Uiso 0.5 1 d . . P A 1
O2A O 0.466(2) 0.276(3) -0.018(2) 0.084(9) Uiso 0.5 1 d . . P A 1
N2B N 0.432(2) 0.416(4) -0.022(3) 0.065(10) Uiso 0.5 1 d . . P A 2
O1B O 0.438(2) 0.487(3) -0.101(3) 0.087(9) Uiso 0.5 1 d . . P A 2
O2B O 0.4976(18) 0.363(3) 0.038(2) 0.072(8) Uiso 0.5 1 d . . P A 2

_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 1.175(18) . ?
O4 N4 1.243(19) . ?
O5 N6 1.241(18) . ?
O6 N6 1.191(18) . ?
O7 N8 1.219(17) . ?
O8 N8 1.222(18) . ?
O9 N10 1.220(17) . ?
O10 N10 1.198(17) . ?
O11 N12 1.239(17) . ?
O12 N12 1.142(16) . ?
O13 N14 1.200(17) . ?
O14 N14 1.238(17) . ?
O15 N16 1.254(17) . ?
O16 N16 1.181(16) . ?
N1 N2B 1.23(4) . ?
N1 C3 1.46(2) . ?
N1 C1 1.44(2) . ?
N1 N2A 1.51(5) . ?
N3 C4 1.41(2) . ?
N3 N4 1.46(2) . ?
N3 C5 1.49(2) . ?
N5 N6 1.361(18) . ?
N5 C4 1.45(2) . ?
N5 C6 1.459(19) . ?
N7 N8 1.384(18) . ?
N7 C3 1.46(2) . ?
N7 C2 1.50(2) . ?
N9 N10 1.401(19) . ?
N9 C2 1.42(2) . ?
N9 C6 1.443(19) . ?
N11 N12 1.424(18) . ?
N11 C1 1.437(18) . ?
N11 C5 1.442(18) . ?
N13 N14 1.347(19) . ?
N13 C7 1.464(18) . ?
N13 C8 1.476(19) . ?
N15 N16 1.381(18) . ?
N15 C8 1.428(18) . ?
N15 C7 1.474(18) 3_575 ?
C1 C2 1.57(2) . ?
C1 H1 0.9800 . ?
C2 H2 0.9800 . ?
C3 C4 1.66(2) . ?
C3 H3 0.9800 . ?
C4 H4 0.9800 . ?
C5 C6 1.55(2) . ?
C5 H5 0.9800 . ?
C6 H6 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N2A O2A 1.09(5) . ?
N2A O1A 1.21(5) . ?
N2B O1B 1.22(4) . ?
N2B O2B 1.32(4) . ?

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
N2B N1 C3 122(2) . . ?
N2B N1 C1 124(2) . . ?
C3 N1 C1 112.4(13) . . ?
C3 N1 N2A 120(2) . . ?
C1 N1 N2A 122(2) . . ?
C4 N3 N4 115.8(14) . . ?
C4 N3 C5 108.9(14) . . ?
N4 N3 C5 115.2(13) . . ?
O3 N4 O4 132.6(18) . . ?
O3 N4 N3 115.0(16) . . ?
O4 N4 N3 112.3(16) . . ?
N6 N5 C4 120.4(14) . . ?
N6 N5 C6 117.1(14) . . ?
C4 N5 C6 111.9(13) . . ?
O6 N6 O5 122.9(16) . . ?
O6 N6 N5 120.4(15) . . ?
O5 N6 N5 116.7(16) . . ?
N8 N7 C3 116.5(14) . . ?
N8 N7 C2 117.2(13) . . ?
C3 N7 C2 108.9(13) . . ?
O7 N8 O8 123.7(17) . . ?
O7 N8 N7 119.0(15) . . ?
O8 N8 N7 117.1(17) . . ?
N10 N9 C2 117.9(14) . . ?
N10 N9 C6 118.0(13) . . ?
C2 N9 C6 119.2(14) . . ?
O10 N10 O9 125.6(17) . . ?
O10 N10 N9 116.4(15) . . ?
O9 N10 N9 117.8(15) . . ?
N12 N11 C1 121.5(12) . . ?
N12 N11 C5 117.1(12) . . ?
C1 N11 C5 118.8(12) . . ?
O12 N12 O11 130.7(16) . . ?
O12 N12 N11 118.4(14) . . ?
O11 N12 N11 111.0(14) . . ?
N14 N13 C7 116.6(13) . . ?
N14 N13 C8 117.7(13) . . ?
C7 N13 C8 121.3(14) . . ?
O13 N14 O14 126.3(18) . . ?
O13 N14 N13 117.7(15) . . ?
O14 N14 N13 115.6(14) . . ?
N16 N15 C8 119.9(13) . . ?
N16 N15 C7 110.9(12) . 3_575 ?
C8 N15 C7 124.7(12) . 3_575 ?
O16 N16 O15 125.2(16) . . ?
O16 N16 N15 119.4(15) . . ?
O15 N16 N15 115.3(14) . . ?
N11 C1 N1 110.5(13) . . ?
N11 C1 C2 108.3(12) . . ?
N1 C1 C2 102.1(12) . . ?
N11 C1 H1 111.8 . . ?
N1 C1 H1 111.8 . . ?
C2 C1 H1 111.8 . . ?
N9 C2 N7 109.6(12) . . ?
N9 C2 C1 108.4(13) . . ?
N7 C2 C1 104.5(13) . . ?
N9 C2 H2 111.4 . . ?
N7 C2 H2 111.4 . . ?
C1 C2 H2 111.4 . . ?
N1 C3 N7 101.0(13) . . ?
N1 C3 C4 109.1(13) . . ?
N7 C3 C4 106.0(13) . . ?
N1 C3 H3 113.3 . . ?
N7 C3 H3 113.3 . . ?
C4 C3 H3 113.3 . . ?
N3 C4 N5 100.5(14) . . ?
N3 C4 C3 107.9(13) . . ?
N5 C4 C3 111.5(14) . . ?
N3 C4 H4 112.1 . . ?
N5 C4 H4 112.1 . . ?
C3 C4 H4 112.1 . . ?
N11 C5 N3 107.7(12) . . ?
N11 C5 C6 110.0(13) . . ?
N3 C5 C6 105.4(12) . . ?
N11 C5 H5 111.2 . . ?
N3 C5 H5 111.2 . . ?
C6 C5 H5 111.2 . . ?
N9 C6 N5 113.3(12) . . ?
N9 C6 C5 107.4(12) . . ?
N5 C6 C5 100.0(12) . . ?
N9 C6 H6 111.8 . . ?
N5 C6 H6 111.8 . . ?
C5 C6 H6 111.8 . . ?
N13 C7 N15 108.3(12) . 3_575 ?
N13 C7 H7A 110.0 . . ?
N15 C7 H7A 110.0 3_575 . ?
N13 C7 H7B 110.0 . . ?
N15 C7 H7B 110.0 3_575 . ?
H7A C7 H7B 108.4 . . ?
N15 C8 N13 111.8(12) . . ?
N15 C8 H8A 109.3 . . ?
N13 C8 H8A 109.3 . . ?
N15 C8 H8B 109.3 . . ?
N13 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
O2A N2A O1A 139(6) . . ?
O2A N2A N1 115(4) . . ?
O1A N2A N1 106(4) . . ?
N1 N2B O1B 120(4) . . ?
N1 N2B O2B 119(3) . . ?
O1B N2B O2B 120(4) . . ?

_refine_diff_density_max         0.858
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.174

