# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_shrv285
_database_code_depnum_ccdc_archive 'CCDC 1474579'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            'JZ 7-1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N12 O8'
_chemical_formula_sum            'C7 H8 N12 O8'
_chemical_formula_weight         388.25

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   14.3822(16)
_cell_length_b                   9.5669(11)
_cell_length_c                   11.2707(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1550.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_T_max  0.987
_diffrn_ambient_temperature      150(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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13367
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.361
_diffrn_reflns_theta_max         26.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3143
_reflns_number_gt                3055
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.998

_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       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_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)+(0.0345P)²+0.2018P] 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_abs_structure_details 
;
 Flack x determined using 1401 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3143
_refine_ls_number_parameters     246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0573
_refine_ls_wR_factor_gt          0.0566
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.017
_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 0.74815(13) -0.0947(2) 1.06210(19) 0.0384(5) Uani 1 1 d . . . . .
H1A H 0.7726 -0.1633 1.1187 0.058 Uiso 1 1 calc R U . . .
H1B H 0.7211 -0.0158 1.1055 0.058 Uiso 1 1 calc R U . . .
H1C H 0.7988 -0.0612 1.0113 0.058 Uiso 1 1 calc R U . . .
N2 N 0.67669(10) -0.16019(18) 0.98885(14) 0.0302(3) Uani 1 1 d . . . . .
N3 N 0.70770(11) -0.25143(17) 0.91932(15) 0.0329(4) Uani 1 1 d . . . . .
O4 O 0.79042(12) -0.2894(2) 0.9057(2) 0.0750(7) Uani 1 1 d . . . . .
C5 C 0.63972(14) -0.3182(2) 0.84691(16) 0.0299(4) Uani 1 1 d . . . . .
N6 N 0.66211(15) -0.42534(19) 0.78313(16) 0.0446(5) Uani 1 1 d . . . . .
O7 O 0.58132(14) -0.46123(16) 0.72482(15) 0.0514(4) Uani 1 1 d . . . . .
N8 N 0.50876(14) -0.37307(18) 0.75464(15) 0.0403(4) Uani 1 1 d . . . . .
C9 C 0.54390(13) -0.28442(18) 0.82963(15) 0.0261(4) Uani 1 1 d . . . . .
N10 N 0.49158(9) -0.17153(16) 0.87053(13) 0.0230(3) Uani 1 1 d . . . . .
N11 N 0.47285(10) -0.16509(17) 0.99117(14) 0.0262(3) Uani 1 1 d . . . . .
O12 O 0.49143(10) -0.26816(15) 1.04927(13) 0.0353(3) Uani 1 1 d . . . . .
O13 O 0.43919(10) -0.05537(14) 1.02628(12) 0.0343(3) Uani 1 1 d . . . . .
C14 C 0.46040(11) -0.05921(18) 0.79424(16) 0.0248(4) Uani 1 1 d . . . . .
H14A H 0.3934 -0.0424 0.8086 0.030 Uiso 1 1 calc R U . . .
H14B H 0.4677 -0.0883 0.7105 0.030 Uiso 1 1 calc R U . . .
N15 N 0.51118(10) 0.07065(15) 0.81311(14) 0.0256(3) Uani 1 1 d . . . . .
N16 N 0.60371(10) 0.07791(16) 0.77787(12) 0.0258(3) Uani 1 1 d . . . . .
O17 O 0.63870(9) -0.03266(14) 0.74793(12) 0.0311(3) Uani 1 1 d . . . . .
O18 O 0.64086(9) 0.19227(14) 0.78202(12) 0.0333(3) Uani 1 1 d . . . . .
C19 C 0.46754(12) 0.19411(18) 0.84727(16) 0.0250(4) Uani 1 1 d . . . . .
N20 N 0.38548(12) 0.22553(18) 0.80669(17) 0.0360(4) Uani 1 1 d . . . . .
N21 N 0.43040(12) 0.39167(18) 0.94051(16) 0.0380(4) Uani 1 1 d . . . . .
O21 O 0.36085(10) 0.34704(16) 0.86479(15) 0.0445(4) Uani 1 1 d . . . . .
C22 C 0.49482(12) 0.29833(18) 0.92997(17) 0.0265(4) Uani 1 1 d . . . . .
N23 N 0.57789(11) 0.30232(15) 1.00075(14) 0.0265(3) Uani 1 1 d . . . . .
O24 O 0.60331(9) 0.18595(14) 1.04211(13) 0.0330(3) Uani 1 1 d . . . . .
N25 N 0.61456(13) 0.42147(18) 1.01382(15) 0.0370(4) Uani 1 1 d . . . . .
C26 C 0.69727(17) 0.4161(3) 1.0886(2) 0.0513(6) Uani 1 1 d . . . . .
H26A H 0.6802 0.3824 1.1678 0.077 Uiso 1 1 calc R U . . .
H26B H 0.7243 0.5098 1.0950 0.077 Uiso 1 1 calc R U . . .
H26C H 0.7429 0.3524 1.0533 0.077 Uiso 1 1 calc R U . . .

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
C1 0.0253(9) 0.0508(12) 0.0391(11) 0.0102(10) -0.0084(8) -0.0073(9)
N2 0.0219(7) 0.0420(9) 0.0266(8) 0.0037(7) -0.0004(6) 0.0007(6)
N3 0.0233(7) 0.0415(8) 0.0340(8) 0.0082(8) 0.0027(7) 0.0100(6)
O4 0.0269(8) 0.0973(15) 0.1009(17) -0.0245(14) -0.0030(9) 0.0295(9)
C5 0.0363(10) 0.0297(9) 0.0236(9) 0.0050(7) 0.0063(7) 0.0111(8)
N6 0.0611(12) 0.0404(10) 0.0324(9) 0.0001(8) 0.0079(9) 0.0220(9)
O7 0.0818(12) 0.0349(8) 0.0375(8) -0.0136(7) -0.0014(8) 0.0157(8)
N8 0.0560(11) 0.0327(9) 0.0321(10) -0.0082(8) -0.0060(8) 0.0028(8)
C9 0.0315(9) 0.0263(8) 0.0206(8) -0.0001(7) 0.0008(7) 0.0009(7)
N10 0.0216(7) 0.0283(8) 0.0191(7) -0.0037(6) 0.0014(6) 0.0015(6)
N11 0.0196(6) 0.0365(8) 0.0226(7) -0.0035(6) 0.0037(6) -0.0059(6)
O12 0.0363(7) 0.0429(8) 0.0268(6) 0.0064(6) 0.0047(6) -0.0035(6)
O13 0.0326(7) 0.0395(7) 0.0307(7) -0.0106(6) 0.0101(6) -0.0014(6)
C14 0.0215(8) 0.0273(9) 0.0255(9) -0.0046(7) -0.0034(7) 0.0002(6)
N15 0.0189(7) 0.0263(7) 0.0317(8) -0.0050(6) 0.0034(6) 0.0004(5)
N16 0.0213(7) 0.0365(9) 0.0195(7) 0.0063(6) 0.0013(6) 0.0024(6)
O17 0.0278(6) 0.0390(7) 0.0264(6) 0.0067(6) 0.0075(5) 0.0115(6)
O18 0.0273(6) 0.0400(8) 0.0327(7) 0.0069(6) 0.0013(6) -0.0085(5)
C19 0.0237(8) 0.0273(9) 0.0239(8) -0.0013(7) -0.0008(6) 0.0006(7)
N20 0.0312(8) 0.0375(9) 0.0393(9) -0.0117(8) -0.0076(7) 0.0092(7)
N21 0.0371(9) 0.0340(9) 0.0431(10) -0.0097(8) -0.0101(8) 0.0066(7)
O21 0.0364(8) 0.0411(8) 0.0561(10) -0.0177(7) -0.0171(7) 0.0161(7)
C22 0.0277(9) 0.0258(9) 0.0261(9) 0.0004(8) -0.0020(7) -0.0006(6)
N23 0.0282(7) 0.0281(7) 0.0232(7) 0.0022(6) -0.0030(6) -0.0027(6)
O24 0.0354(7) 0.0324(7) 0.0313(7) 0.0081(6) -0.0058(6) 0.0006(5)
N25 0.0402(9) 0.0360(9) 0.0349(9) 0.0043(7) -0.0098(7) -0.0125(7)
C26 0.0483(13) 0.0570(14) 0.0486(13) 0.0081(11) -0.0201(11) -0.0221(11)

_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 N2 1.459(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 N3 1.255(2) . ?
N3 O4 1.253(2) . ?
N3 C5 1.425(3) . ?
C5 N6 1.292(3) . ?
C5 C9 1.429(3) . ?
N6 O7 1.378(3) . ?
O7 N8 1.383(2) . ?
N8 C9 1.300(2) . ?
C9 N10 1.395(2) . ?
N10 N11 1.387(2) . ?
N10 C14 1.447(2) . ?
N11 O12 1.214(2) . ?
N11 O13 1.222(2) . ?
C14 N15 1.457(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N15 N16 1.3906(19) . ?
N15 C19 1.392(2) . ?
N16 O17 1.2190(19) . ?
N16 O18 1.218(2) . ?
C19 N20 1.301(3) . ?
C19 C22 1.420(3) . ?
N20 O21 1.380(2) . ?
N21 C22 1.292(2) . ?
N21 O21 1.382(2) . ?
C22 N23 1.437(2) . ?
N23 O24 1.2611(19) . ?
N23 N25 1.265(2) . ?
N25 C26 1.459(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 N2 C1 113.66(16) . . ?
O4 N3 N2 127.97(19) . . ?
O4 N3 C5 116.84(18) . . ?
N2 N3 C5 115.20(15) . . ?
N6 C5 N3 120.21(18) . . ?
N6 C5 C9 110.12(19) . . ?
N3 C5 C9 129.67(16) . . ?
C5 N6 O7 104.64(17) . . ?
N6 O7 N8 111.61(15) . . ?
C9 N8 O7 105.23(17) . . ?
N8 C9 N10 120.70(17) . . ?
N8 C9 C5 108.42(17) . . ?
N10 C9 C5 130.59(17) . . ?
N11 N10 C9 117.58(15) . . ?
N11 N10 C14 119.27(14) . . ?
C9 N10 C14 123.08(15) . . ?
O12 N11 O13 127.63(16) . . ?
O12 N11 N10 116.74(15) . . ?
O13 N11 N10 115.63(16) . . ?
N10 C14 N15 113.02(14) . . ?
N10 C14 H14A 109.0 . . ?
N15 C14 H14A 109.0 . . ?
N10 C14 H14B 109.0 . . ?
N15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
N16 N15 C19 117.91(14) . . ?
N16 N15 C14 118.74(13) . . ?
C19 N15 C14 122.55(14) . . ?
O17 N16 O18 127.50(15) . . ?
O17 N16 N15 115.51(14) . . ?
O18 N16 N15 116.97(14) . . ?
N20 C19 N15 120.53(16) . . ?
N20 C19 C22 108.61(16) . . ?
N15 C19 C22 130.75(16) . . ?
C19 N20 O21 105.11(15) . . ?
C22 N21 O21 104.39(15) . . ?
N20 O21 N21 111.55(13) . . ?
N21 C22 C19 110.33(16) . . ?
N21 C22 N23 121.78(17) . . ?
C19 C22 N23 127.78(16) . . ?
O24 N23 N25 129.18(16) . . ?
O24 N23 C22 115.01(14) . . ?
N25 N23 C22 115.81(15) . . ?
N23 N25 C26 112.05(17) . . ?
N25 C26 H26A 109.5 . . ?
N25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
C1 N2 N3 O4 -1.0(3) . . . . ?
C1 N2 N3 C5 179.61(16) . . . . ?
O4 N3 C5 N6 9.1(3) . . . . ?
N2 N3 C5 N6 -171.36(18) . . . . ?
O4 N3 C5 C9 -169.9(2) . . . . ?
N2 N3 C5 C9 9.6(3) . . . . ?
N3 C5 N6 O7 -179.34(16) . . . . ?
C9 C5 N6 O7 -0.1(2) . . . . ?
C5 N6 O7 N8 0.0(2) . . . . ?
N6 O7 N8 C9 0.1(2) . . . . ?
O7 N8 C9 N10 174.21(16) . . . . ?
O7 N8 C9 C5 -0.2(2) . . . . ?
N6 C5 C9 N8 0.2(2) . . . . ?
N3 C5 C9 N8 179.32(18) . . . . ?
N6 C5 C9 N10 -173.44(18) . . . . ?
N3 C5 C9 N10 5.7(3) . . . . ?
N8 C9 N10 N11 117.72(19) . . . . ?
C5 C9 N10 N11 -69.3(2) . . . . ?
N8 C9 N10 C14 -65.3(2) . . . . ?
C5 C9 N10 C14 107.6(2) . . . . ?
C9 N10 N11 O12 -10.6(2) . . . . ?
C14 N10 N11 O12 172.33(14) . . . . ?
C9 N10 N11 O13 169.53(15) . . . . ?
C14 N10 N11 O13 -7.6(2) . . . . ?
N11 N10 C14 N15 69.98(19) . . . . ?
C9 N10 C14 N15 -106.94(18) . . . . ?
N10 C14 N15 N16 69.9(2) . . . . ?
N10 C14 N15 C19 -120.61(17) . . . . ?
C19 N15 N16 O17 -179.47(15) . . . . ?
C14 N15 N16 O17 -9.5(2) . . . . ?
C19 N15 N16 O18 1.6(2) . . . . ?
C14 N15 N16 O18 171.64(15) . . . . ?
N16 N15 C19 N20 132.93(19) . . . . ?
C14 N15 C19 N20 -36.7(3) . . . . ?
N16 N15 C19 C22 -51.4(3) . . . . ?
C14 N15 C19 C22 139.0(2) . . . . ?
N15 C19 N20 O21 175.59(16) . . . . ?
C22 C19 N20 O21 -0.9(2) . . . . ?
C19 N20 O21 N21 1.2(2) . . . . ?
C22 N21 O21 N20 -1.0(2) . . . . ?
O21 N21 C22 C19 0.4(2) . . . . ?
O21 N21 C22 N23 -176.11(17) . . . . ?
N20 C19 C22 N21 0.4(2) . . . . ?
N15 C19 C22 N21 -175.69(19) . . . . ?
N20 C19 C22 N23 176.60(18) . . . . ?
N15 C19 C22 N23 0.5(3) . . . . ?
N21 C22 N23 O24 136.76(19) . . . . ?
C19 C22 N23 O24 -39.1(3) . . . . ?
N21 C22 N23 N25 -42.5(3) . . . . ?
C19 C22 N23 N25 141.6(2) . . . . ?
O24 N23 N25 C26 -0.3(3) . . . . ?
C22 N23 N25 C26 178.87(18) . . . . ?

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
C1 H1A O18 0.98 2.62 3.584(2) 169.0 3_645
C1 H1C N21 0.98 2.62 3.539(3) 156.7 4
C14 H14A O4 0.99 2.45 3.107(2) 123.7 4_445
C14 H14B O24 0.99 2.35 3.223(2) 146.7 2_654

_refine_diff_density_max         0.135
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.027


# start Validation Reply Form
_vrf_PLAT015_shrv285             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ...      Please Do ! 
RESPONSE: It is our policy to routinley not supply the HKL file unless
specifically required.
;
_vrf_PLAT430_shrv285             
;
PROBLEM: Short Inter D...A Contact  O4     ..  N11     ..       2.83 Ang.  
RESPONSE: It is common for nitro-containing structures to have high densities,
which result in some short contacts, as seen here.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv323
_database_code_depnum_ccdc_archive 'CCDC 1504349'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H6 N12 O8'
_chemical_formula_sum            'C10 H6 N12 O8'
_chemical_formula_weight         422.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.2994(8)
_cell_length_b                   8.8927(8)
_cell_length_c                   9.8472(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.317(3)
_cell_angle_gamma                90
_cell_volume                     801.17(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1585
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      22.05

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.153
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_T_max  0.7454

_diffrn_ambient_temperature      296(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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7460
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.775
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1639
_reflns_number_gt                1110
_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       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0974P)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         1639
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 -0.1993(3) 0.5780(4) 0.6729(3) 0.0617(7) Uani 1 1 d . . . A 1
H1 H -0.2939 0.6107 0.6390 0.074 Uiso 1 1 calc R U . A 1
O2 O -0.0841(2) 0.6281(2) 0.62473(19) 0.0695(6) Uani 1 1 d . . . A 1
N3 N 0.0370(2) 0.5526(3) 0.7007(2) 0.0574(6) Uani 1 1 d . . . A 1
C4 C -0.0212(2) 0.4691(2) 0.7823(2) 0.0375(5) Uani 1 1 d . . . A 1
N5 N -0.1698(2) 0.4808(2) 0.7702(2) 0.0533(6) Uani 1 1 d . . . A 1
C6 C 0.0665(2) 0.3710(2) 0.8828(2) 0.0368(5) Uani 1 1 d . . . A 1
N7 N 0.00670(19) 0.2803(2) 0.95987(19) 0.0477(5) Uani 1 1 d . . . A 1
O8 O 0.12106(17) 0.2102(2) 1.04494(17) 0.0562(5) Uani 1 1 d . . . A 1
N9 N 0.25296(19) 0.2587(2) 1.01769(19) 0.0493(5) Uani 1 1 d . . . A 1
C10 C 0.2212(2) 0.3564(3) 0.9204(2) 0.0370(5) Uani 1 1 d . . . A 1
N11 N 0.33208(18) 0.4409(2) 0.87766(17) 0.0440(5) Uani 1 1 d . . . A 1
N12 N 0.3499(2) 0.4242(3) 0.74199(19) 0.0486(5) Uani 1 1 d . . . A 1
O13 O 0.26888(19) 0.3347(2) 0.67222(16) 0.0613(5) Uani 1 1 d . . . A 1
O14 O 0.4436(2) 0.5010(2) 0.70582(19) 0.0706(6) Uani 1 1 d . . . A 1
C15 C 0.4279(2) 0.5392(3) 0.9716(2) 0.0414(5) Uani 1 1 d . . . A 1
H15A H 0.3799 0.5678 1.0474 0.050 Uiso 1 1 calc R U . A 1
H15B H 0.4471 0.6299 0.9232 0.050 Uiso 1 1 calc R U . A 1

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
C1 0.0409(13) 0.0735(18) 0.0661(16) -0.0019(15) -0.0034(12) 0.0163(13)
O2 0.0673(12) 0.0671(13) 0.0684(11) 0.0194(10) -0.0034(10) 0.0146(10)
N3 0.0444(11) 0.0630(14) 0.0615(13) 0.0169(11) 0.0005(10) 0.0036(10)
C4 0.0321(10) 0.0400(12) 0.0388(11) -0.0056(9) 0.0020(9) -0.0019(9)
N5 0.0320(9) 0.0640(14) 0.0608(13) -0.0050(11) 0.0002(9) 0.0065(9)
C6 0.0305(10) 0.0420(12) 0.0369(10) -0.0065(9) 0.0037(8) -0.0053(9)
N7 0.0412(10) 0.0499(12) 0.0516(11) 0.0028(9) 0.0069(9) -0.0090(9)
O8 0.0520(9) 0.0596(11) 0.0549(9) 0.0172(8) 0.0041(8) -0.0067(8)
N9 0.0405(10) 0.0562(12) 0.0491(11) 0.0082(10) 0.0025(9) -0.0009(9)
C10 0.0325(10) 0.0444(13) 0.0321(10) -0.0029(9) 0.0004(8) -0.0036(9)
N11 0.0290(8) 0.0657(13) 0.0358(9) -0.0003(9) 0.0013(7) -0.0104(9)
N12 0.0354(9) 0.0680(14) 0.0419(10) 0.0070(10) 0.0056(8) 0.0079(10)
O13 0.0561(10) 0.0827(14) 0.0428(9) -0.0133(9) 0.0024(8) 0.0013(9)
O14 0.0534(10) 0.0962(16) 0.0681(12) 0.0195(11) 0.0270(10) -0.0042(10)
C15 0.0305(10) 0.0422(13) 0.0481(12) 0.0016(10) -0.0021(9) -0.0035(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
C1 N5 1.283(4) . ?
C1 O2 1.324(3) . ?
C1 H1 0.9300 . ?
O2 N3 1.406(3) . ?
N3 C4 1.284(3) . ?
C4 N5 1.369(3) . ?
C4 C6 1.455(3) . ?
C6 N7 1.299(3) . ?
C6 C10 1.426(3) . ?
N7 O8 1.379(2) . ?
O8 N9 1.371(2) . ?
N9 C10 1.288(3) . ?
C10 N11 1.400(3) . ?
N11 N12 1.383(3) . ?
N11 C15 1.455(3) . ?
N12 O14 1.210(3) . ?
N12 O13 1.220(3) . ?
C15 C15 1.526(4) 3_667 ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
N5 C1 O2 114.6(2) . . ?
N5 C1 H1 122.7 . . ?
O2 C1 H1 122.7 . . ?
C1 O2 N3 105.73(19) . . ?
C4 N3 O2 102.81(18) . . ?
N3 C4 N5 115.7(2) . . ?
N3 C4 C6 121.65(18) . . ?
N5 C4 C6 122.6(2) . . ?
C1 N5 C4 101.2(2) . . ?
N7 C6 C10 108.03(18) . . ?
N7 C6 C4 121.55(17) . . ?
C10 C6 C4 130.38(19) . . ?
C6 N7 O8 105.74(15) . . ?
N9 O8 N7 111.02(15) . . ?
C10 N9 O8 105.29(17) . . ?
N9 C10 N11 120.16(18) . . ?
N9 C10 C6 109.91(19) . . ?
N11 C10 C6 129.5(2) . . ?
N12 N11 C10 117.04(18) . . ?
N12 N11 C15 120.84(17) . . ?
C10 N11 C15 122.09(17) . . ?
O14 N12 O13 127.4(2) . . ?
O14 N12 N11 116.2(2) . . ?
O13 N12 N11 116.44(19) . . ?
N11 C15 C15 110.9(2) . 3_667 ?
N11 C15 H15A 109.5 . . ?
C15 C15 H15A 109.5 3_667 . ?
N11 C15 H15B 109.5 . . ?
C15 C15 H15B 109.5 3_667 . ?
H15A C15 H15B 108.0 . . ?

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
N5 C1 O2 N3 0.3(3) . . . . ?
C1 O2 N3 C4 0.1(3) . . . . ?
O2 N3 C4 N5 -0.4(3) . . . . ?
O2 N3 C4 C6 -179.15(19) . . . . ?
O2 C1 N5 C4 -0.5(3) . . . . ?
N3 C4 N5 C1 0.6(3) . . . . ?
C6 C4 N5 C1 179.3(2) . . . . ?
N3 C4 C6 N7 -176.0(2) . . . . ?
N5 C4 C6 N7 5.3(3) . . . . ?
N3 C4 C6 C10 6.4(3) . . . . ?
N5 C4 C6 C10 -172.3(2) . . . . ?
C10 C6 N7 O8 0.3(2) . . . . ?
C4 C6 N7 O8 -177.79(18) . . . . ?
C6 N7 O8 N9 -0.6(2) . . . . ?
N7 O8 N9 C10 0.7(2) . . . . ?
O8 N9 C10 N11 173.01(19) . . . . ?
O8 N9 C10 C6 -0.5(2) . . . . ?
N7 C6 C10 N9 0.2(2) . . . . ?
C4 C6 C10 N9 178.0(2) . . . . ?
N7 C6 C10 N11 -172.6(2) . . . . ?
C4 C6 C10 N11 5.3(4) . . . . ?
N9 C10 N11 N12 118.4(2) . . . . ?
C6 C10 N11 N12 -69.5(3) . . . . ?
N9 C10 N11 C15 -59.9(3) . . . . ?
C6 C10 N11 C15 112.2(3) . . . . ?
C10 N11 N12 O14 178.1(2) . . . . ?
C15 N11 N12 O14 -3.6(3) . . . . ?
C10 N11 N12 O13 -1.4(3) . . . . ?
C15 N11 N12 O13 176.92(19) . . . . ?
N12 N11 C15 C15 -80.9(3) . . . 3_667 ?
C10 N11 C15 C15 97.4(3) . . . 3_667 ?

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
C1 H1 N7 0.93 2.54 3.432(3) 161.0 2_456

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.050


# start Validation Reply Form
_vrf_PLAT015_shrv323             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinley not supply the HKL file unless 
specifically required.

;
