# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
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data_cd15349m
_database_code_depnum_ccdc_archive 'CCDC 1552452'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H2 Cl3 N5 O4'
_chemical_formula_weight         338.50

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'
Cl Cl 0.1484 0.1585 '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                   8.8432(19)
_cell_length_b                   17.400(4)
_cell_length_c                   16.430(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.832(4)
_cell_angle_gamma                90
_cell_volume                     2526.9(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4096
_cell_measurement_theta_min      4.677
_cell_measurement_theta_max      56.497

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.746
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6378
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14977
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.705
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4970
_reflns_number_gt                3636
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0539P)²+0.7201P] 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         4970
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 1.01961(7) 0.36092(5) -0.02499(4) 0.0672(2) Uani 1 1 d . . . . .
Cl2 Cl 0.41890(7) 0.35621(4) -0.08209(4) 0.0595(2) Uani 1 1 d . . . . .
Cl3 Cl 0.64354(8) 0.43846(4) 0.21164(4) 0.0615(2) Uani 1 1 d . . . . .
Cl4 Cl 0.76442(8) 0.06372(4) -0.18336(4) 0.0668(2) Uani 1 1 d . . . . .
Cl5 Cl 0.40291(7) 0.14394(5) 0.05711(4) 0.0676(2) Uani 1 1 d . . . . .
Cl6 Cl 1.00478(7) 0.14954(4) 0.10701(4) 0.0635(2) Uani 1 1 d . . . . .
N1 N 0.7397(2) 0.33774(10) -0.12632(11) 0.0415(4) Uani 1 1 d . . . . .
N2 N 0.7305(3) 0.26374(12) -0.14907(14) 0.0693(7) Uani 1 1 d . . . . .
N3 N 0.7592(3) 0.34016(14) -0.25705(13) 0.0626(6) Uani 1 1 d . . . . .
N4 N 0.3973(2) 0.40432(14) 0.09052(13) 0.0532(5) Uani 1 1 d . . . . .
N5 N 0.9470(2) 0.41248(15) 0.14266(13) 0.0570(6) Uani 1 1 d . . . . .
N6 N 0.6870(2) 0.16638(10) 0.15514(11) 0.0407(4) Uani 1 1 d . . . . .
N7 N 0.6885(3) 0.24080(12) 0.17753(13) 0.0653(6) Uani 1 1 d . . . . .
N8 N 0.6722(3) 0.16448(14) 0.28625(12) 0.0596(6) Uani 1 1 d . . . . .
N9 N 0.4682(2) 0.09089(14) -0.11040(12) 0.0528(5) Uani 1 1 d . . . . .
N10 N 1.0194(2) 0.10191(16) -0.06742(13) 0.0592(6) Uani 1 1 d . . . . .
O1 O 0.3371(2) 0.34897(14) 0.11723(16) 0.0960(8) Uani 1 1 d . . . . .
O2 O 0.3413(2) 0.46632(13) 0.08354(19) 0.1022(9) Uani 1 1 d . . . . .
O3 O 1.0066(2) 0.35671(15) 0.17252(14) 0.0871(7) Uani 1 1 d . . . . .
O4 O 0.9823(3) 0.47741(15) 0.15478(17) 0.1031(8) Uani 1 1 d . . . . .
O5 O 0.4166(2) 0.14476(14) -0.14679(14) 0.0875(7) Uani 1 1 d . . . . .
O6 O 0.4204(3) 0.02647(13) -0.11379(15) 0.0901(7) Uani 1 1 d . . . . .
O7 O 1.0673(3) 0.03911(15) -0.07787(18) 0.1083(9) Uani 1 1 d . . . . .
O8 O 1.0849(3) 0.16034(15) -0.08174(17) 0.0969(8) Uani 1 1 d . . . . .
C1 C 0.8407(2) 0.37381(13) 0.00777(13) 0.0402(5) Uani 1 1 d . . . . .
C2 C 0.7179(2) 0.35996(12) -0.04444(13) 0.0379(5) Uani 1 1 d . . . . .
C3 C 0.5718(2) 0.37015(12) -0.01766(14) 0.0408(5) Uani 1 1 d . . . . .
C4 C 0.5519(2) 0.39438(13) 0.06114(13) 0.0396(5) Uani 1 1 d . . . . .
C5 C 0.6727(2) 0.40950(12) 0.11393(13) 0.0399(5) Uani 1 1 d . . . . .
C6 C 0.8164(2) 0.39854(13) 0.08606(13) 0.0407(5) Uani 1 1 d . . . . .
C7 C 0.7565(3) 0.38111(16) -0.19158(15) 0.0615(7) Uani 1 1 d . . . . .
H7 H 0.7652 0.4344 -0.1904 0.074 Uiso 1 1 calc R U . . .
C8 C 0.7437(4) 0.26921(18) -0.22772(17) 0.0699(8) Uani 1 1 d . . . . .
H8 H 0.7424 0.2262 -0.2613 0.084 Uiso 1 1 calc R U . . .
C9 C 0.7431(3) 0.09393(13) -0.08556(13) 0.0413(5) Uani 1 1 d . . . . .
C10 C 0.6013(2) 0.10526(12) -0.05597(13) 0.0402(5) Uani 1 1 d . . . . .
C11 C 0.5806(2) 0.13100(13) 0.02202(13) 0.0406(5) Uani 1 1 d . . . . .
C12 C 0.7063(2) 0.14414(12) 0.07314(13) 0.0375(5) Uani 1 1 d . . . . .
C13 C 0.8497(2) 0.13435(13) 0.04383(13) 0.0412(5) Uani 1 1 d . . . . .
C14 C 0.8664(2) 0.10960(13) -0.03524(13) 0.0422(5) Uani 1 1 d . . . . .
C15 C 0.6760(3) 0.12278(16) 0.22102(15) 0.0593(7) Uani 1 1 d . . . . .
H15 H 0.6716 0.0694 0.2204 0.071 Uiso 1 1 calc R U . . .
C16 C 0.6796(3) 0.23504(17) 0.25665(16) 0.0649(7) Uani 1 1 d . . . . .
H16 H 0.6784 0.2781 0.2902 0.078 Uiso 1 1 calc R U . . .


_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
Cl1 C1 1.703(2) . ?
Cl2 C3 1.708(2) . ?
Cl3 C5 1.710(2) . ?
Cl4 C9 1.707(2) . ?
Cl5 C11 1.706(2) . ?
Cl6 C13 1.714(2) . ?
N1 C7 1.323(3) . ?
N1 N2 1.343(3) . ?
N1 C2 1.419(3) . ?
N2 C8 1.305(3) . ?
N3 C7 1.291(3) . ?
N3 C8 1.334(4) . ?
N4 O1 1.191(3) . ?
N4 O2 1.191(3) . ?
N4 C4 1.474(3) . ?
N5 O4 1.187(3) . ?
N5 O3 1.201(3) . ?
N5 C6 1.480(3) . ?
N6 C15 1.328(3) . ?
N6 N7 1.346(3) . ?
N6 C12 1.417(3) . ?
N7 C16 1.309(3) . ?
N7 O1 3.739(4) . ?
N8 C15 1.296(3) . ?
N8 C16 1.323(3) . ?
N9 O5 1.194(3) . ?
N9 O6 1.199(3) . ?
N9 C10 1.477(3) . ?
N10 O7 1.187(3) . ?
N10 O8 1.197(3) . ?
N10 C14 1.474(3) . ?
C1 C6 1.380(3) . ?
C1 C2 1.383(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.378(3) . ?
C7 C8 2.038(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.373(3) . ?
C9 C14 1.375(3) . ?
C10 C11 1.375(3) . ?
C11 C12 1.391(3) . ?
C12 C13 1.381(3) . ?
C13 C14 1.381(3) . ?
C15 C16 2.039(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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
C7 N1 N2 109.2(2) . . ?
C7 N1 C2 129.4(2) . . ?
N2 N1 C2 121.10(18) . . ?
C8 N2 N1 101.5(2) . . ?
C7 N3 C8 101.8(2) . . ?
O1 N4 O2 125.3(2) . . ?
O1 N4 C4 117.1(2) . . ?
O2 N4 C4 117.5(2) . . ?
O4 N5 O3 126.2(2) . . ?
O4 N5 C6 117.2(2) . . ?
O3 N5 C6 116.6(2) . . ?
C15 N6 N7 109.1(2) . . ?
C15 N6 C12 129.3(2) . . ?
N7 N6 C12 121.46(18) . . ?
C16 N7 N6 101.4(2) . . ?
C16 N7 O1 103.04(19) . . ?
N6 N7 O1 114.26(16) . . ?
C15 N8 C16 102.3(2) . . ?
O5 N9 O6 125.6(2) . . ?
O5 N9 C10 117.0(2) . . ?
O6 N9 C10 117.4(2) . . ?
O7 N10 O8 125.2(2) . . ?
O7 N10 C14 118.1(2) . . ?
O8 N10 C14 116.7(2) . . ?
N4 O1 N7 97.31(16) . . ?
C6 C1 C2 119.35(19) . . ?
C6 C1 Cl1 120.66(17) . . ?
C2 C1 Cl1 119.99(17) . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 N1 120.54(19) . . ?
C3 C2 N1 119.39(19) . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 Cl2 120.24(17) . . ?
C2 C3 Cl2 120.76(17) . . ?
C3 C4 C5 121.98(19) . . ?
C3 C4 N4 119.40(19) . . ?
C5 C4 N4 118.6(2) . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 Cl3 121.41(17) . . ?
C4 C5 Cl3 120.64(17) . . ?
C5 C6 C1 121.7(2) . . ?
C5 C6 N5 118.6(2) . . ?
C1 C6 N5 119.68(19) . . ?
N3 C7 N1 111.5(2) . . ?
N3 C7 C8 39.85(15) . . ?
N1 C7 C8 71.62(16) . . ?
N3 C7 H7 124.3 . . ?
N1 C7 H7 124.3 . . ?
C8 C7 H7 164.1 . . ?
N2 C8 N3 116.0(2) . . ?
N2 C8 C7 77.71(17) . . ?
N3 C8 C7 38.33(14) . . ?
N2 C8 H8 122.0 . . ?
N3 C8 H8 122.0 . . ?
C7 C8 H8 160.3 . . ?
C10 C9 C14 118.3(2) . . ?
C10 C9 Cl4 120.49(17) . . ?
C14 C9 Cl4 121.18(17) . . ?
C9 C10 C11 121.8(2) . . ?
C9 C10 N9 118.7(2) . . ?
C11 C10 N9 119.47(19) . . ?
C10 C11 C12 119.23(19) . . ?
C10 C11 Cl5 120.65(17) . . ?
C12 C11 Cl5 120.09(17) . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 N6 120.33(19) . . ?
C11 C12 N6 120.04(19) . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 Cl6 120.68(17) . . ?
C12 C13 Cl6 119.71(17) . . ?
C9 C14 C13 121.4(2) . . ?
C9 C14 N10 119.1(2) . . ?
C13 C14 N10 119.5(2) . . ?
N8 C15 N6 111.0(2) . . ?
N8 C15 C16 39.34(15) . . ?
N6 C15 C16 71.69(16) . . ?
N8 C15 H15 124.5 . . ?
N6 C15 H15 124.5 . . ?
C16 C15 H15 163.8 . . ?
N7 C16 N8 116.2(2) . . ?
N7 C16 C15 77.83(17) . . ?
N8 C16 C15 38.38(13) . . ?
N7 C16 H16 121.9 . . ?
N8 C16 H16 121.9 . . ?
C15 C16 H16 160.3 . . ?

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
C7 N1 N2 C8 0.3(3) . . . . ?
C2 N1 N2 C8 174.7(2) . . . . ?
C15 N6 N7 C16 0.6(3) . . . . ?
C12 N6 N7 C16 -175.2(2) . . . . ?
C15 N6 N7 O1 -109.48(19) . . . . ?
C12 N6 N7 O1 74.8(2) . . . . ?
O2 N4 O1 N7 -157.5(3) . . . . ?
C4 N4 O1 N7 24.8(2) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
Cl1 C1 C2 C3 179.73(17) . . . . ?
C6 C1 C2 N1 177.2(2) . . . . ?
Cl1 C1 C2 N1 -2.3(3) . . . . ?
C7 N1 C2 C1 -87.8(3) . . . . ?
N2 N1 C2 C1 99.1(3) . . . . ?
C7 N1 C2 C3 90.1(3) . . . . ?
N2 N1 C2 C3 -83.0(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
N1 C2 C3 C4 -177.7(2) . . . . ?
C1 C2 C3 Cl2 177.97(17) . . . . ?
N1 C2 C3 Cl2 0.0(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
Cl2 C3 C4 C5 -177.12(17) . . . . ?
C2 C3 C4 N4 -179.1(2) . . . . ?
Cl2 C3 C4 N4 3.1(3) . . . . ?
O1 N4 C4 C3 86.1(3) . . . . ?
O2 N4 C4 C3 -91.9(3) . . . . ?
O1 N4 C4 C5 -93.7(3) . . . . ?
O2 N4 C4 C5 88.4(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
N4 C4 C5 C6 178.8(2) . . . . ?
C3 C4 C5 Cl3 -179.28(18) . . . . ?
N4 C4 C5 Cl3 0.5(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
Cl3 C5 C6 C1 178.78(18) . . . . ?
C4 C5 C6 N5 -178.4(2) . . . . ?
Cl3 C5 C6 N5 -0.1(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
Cl1 C1 C6 C5 179.89(18) . . . . ?
C2 C1 C6 N5 179.2(2) . . . . ?
Cl1 C1 C6 N5 -1.3(3) . . . . ?
O4 N5 C6 C5 -77.7(3) . . . . ?
O3 N5 C6 C5 101.7(3) . . . . ?
O4 N5 C6 C1 103.4(3) . . . . ?
O3 N5 C6 C1 -77.2(3) . . . . ?
C8 N3 C7 N1 -0.3(3) . . . . ?
N2 N1 C7 N3 0.0(3) . . . . ?
C2 N1 C7 N3 -173.8(2) . . . . ?
N2 N1 C7 C8 -0.2(2) . . . . ?
C2 N1 C7 C8 -174.0(2) . . . . ?
N1 N2 C8 N3 -0.5(4) . . . . ?
N1 N2 C8 C7 -0.20(19) . . . . ?
C7 N3 C8 N2 0.5(4) . . . . ?
C14 C9 C10 C11 -0.5(3) . . . . ?
Cl4 C9 C10 C11 -178.71(18) . . . . ?
C14 C9 C10 N9 178.1(2) . . . . ?
Cl4 C9 C10 N9 -0.1(3) . . . . ?
O5 N9 C10 C9 -94.1(3) . . . . ?
O6 N9 C10 C9 86.6(3) . . . . ?
O5 N9 C10 C11 84.6(3) . . . . ?
O6 N9 C10 C11 -94.8(3) . . . . ?
C9 C10 C11 C12 -1.6(3) . . . . ?
N9 C10 C11 C12 179.7(2) . . . . ?
C9 C10 C11 Cl5 -179.60(18) . . . . ?
N9 C10 C11 Cl5 1.8(3) . . . . ?
C10 C11 C12 C13 2.8(3) . . . . ?
Cl5 C11 C12 C13 -179.26(17) . . . . ?
C10 C11 C12 N6 -176.3(2) . . . . ?
Cl5 C11 C12 N6 1.6(3) . . . . ?
C15 N6 C12 C13 -88.8(3) . . . . ?
N7 N6 C12 C13 86.0(3) . . . . ?
C15 N6 C12 C11 90.3(3) . . . . ?
N7 N6 C12 C11 -94.9(3) . . . . ?
C11 C12 C13 C14 -1.7(3) . . . . ?
N6 C12 C13 C14 177.3(2) . . . . ?
C11 C12 C13 Cl6 -179.33(17) . . . . ?
N6 C12 C13 Cl6 -0.2(3) . . . . ?
C10 C9 C14 C13 1.6(3) . . . . ?
Cl4 C9 C14 C13 179.74(18) . . . . ?
C10 C9 C14 N10 -176.6(2) . . . . ?
Cl4 C9 C14 N10 1.5(3) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
Cl6 C13 C14 C9 177.11(18) . . . . ?
C12 C13 C14 N10 177.8(2) . . . . ?
Cl6 C13 C14 N10 -4.7(3) . . . . ?
O7 N10 C14 C9 -73.5(3) . . . . ?
O8 N10 C14 C9 105.7(3) . . . . ?
O7 N10 C14 C13 108.2(3) . . . . ?
O8 N10 C14 C13 -72.5(3) . . . . ?
C16 N8 C15 N6 0.7(3) . . . . ?
N7 N6 C15 N8 -0.9(3) . . . . ?
C12 N6 C15 N8 174.5(2) . . . . ?
N7 N6 C15 C16 -0.40(19) . . . . ?
C12 N6 C15 C16 174.9(2) . . . . ?
N6 N7 C16 N8 -0.2(3) . . . . ?
O1 N7 C16 N8 118.3(2) . . . . ?
N6 N7 C16 C15 -0.38(18) . . . . ?
O1 N7 C16 C15 118.10(13) . . . . ?
C15 N8 C16 N7 -0.3(4) . . . . ?

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
C7 H7 O2 0.93 2.66 3.323(4) 129.1 3_665
C8 H8 O1 0.93 2.55 3.396(4) 151.6 4_665
C15 H15 O6 0.93 2.53 3.237(3) 132.6 3_655
C16 H16 O8 0.93 2.52 3.348(4) 147.7 4_566

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd16192
_database_code_depnum_ccdc_archive 'CCDC 1552455'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H8 Cl4 N16 O8'
_chemical_formula_weight         742.22

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'
Cl Cl 0.1484 0.1585 '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                   16.424(3)
_cell_length_b                   10.270(2)
_cell_length_c                   17.559(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.886(4)
_cell_angle_gamma                90
_cell_volume                     2958.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3437
_cell_measurement_theta_min      4.645
_cell_measurement_theta_max      49.276

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.476
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6452
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15478
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.241
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             5161
_reflns_number_gt                3958
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0746P)²+9.2256P] 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         5161
_refine_ls_number_parameters     433
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.2193
_refine_ls_wR_factor_gt          0.2088
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.122
_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
Cl1 Cl 0.86881(10) 0.90944(17) 0.27158(9) 0.0651(5) Uani 1 1 d . . . . .
Cl2 Cl 1.10009(9) 0.69006(17) 0.11153(9) 0.0616(5) Uani 1 1 d . . . . .
Cl3 Cl 0.65542(10) 0.05472(18) 0.75012(9) 0.0672(5) Uani 1 1 d . . . . .
Cl4 Cl 0.41889(8) 0.33082(15) 0.60539(9) 0.0582(4) Uani 1 1 d . . . . .
N1 N 1.0231(3) 0.7638(6) 0.2532(3) 0.0542(13) Uani 1 1 d . . . . .
N2 N 0.9990(3) 0.7643(5) -0.0258(2) 0.0446(11) Uani 1 1 d . . . . .
N3 N 0.8521(2) 0.9081(4) -0.0211(2) 0.0416(10) Uani 1 1 d . . . . .
N4 N 0.8913(3) 0.9584(5) -0.0807(3) 0.0541(13) Uani 1 1 d . . . . .
N5 N 0.7589(3) 0.9256(9) -0.1126(4) 0.101(3) Uani 1 1 d . . . . .
N6 N 0.7897(2) 0.9796(4) 0.1214(3) 0.0405(10) Uani 1 1 d . . . . .
N7 N 0.7201(3) 0.9116(5) 0.1310(4) 0.0629(15) Uani 1 1 d . . . . .
N8 N 0.6953(3) 1.1239(5) 0.1227(4) 0.0778(19) Uani 1 1 d . . . . .
N9 N 0.5050(3) 0.2180(6) 0.7417(3) 0.0540(12) Uani 1 1 d . . . . .
N10 N 0.4981(3) 0.2572(5) 0.4623(3) 0.0496(11) Uani 1 1 d . . . . .
N11 N 0.6412(3) 0.1060(4) 0.4594(3) 0.0445(11) Uani 1 1 d . . . . .
N12 N 0.6356(4) -0.0109(6) 0.4272(4) 0.082(2) Uani 1 1 d . . . . .
N13 N 0.7157(4) 0.1156(8) 0.3609(3) 0.085(2) Uani 1 1 d . . . . .
N14 N 0.7201(2) 0.0201(4) 0.5944(3) 0.0426(10) Uani 1 1 d . . . . .
N15 N 0.7858(3) 0.0854(5) 0.5703(4) 0.0637(15) Uani 1 1 d . . . . .
N16 N 0.8194(3) -0.1189(5) 0.6032(5) 0.089(2) Uani 1 1 d . . . . .
O1 O 1.0768(3) 0.8341(7) 0.2775(3) 0.101(2) Uani 1 1 d . . . . .
O2 O 1.0038(4) 0.6608(5) 0.2786(3) 0.0863(16) Uani 1 1 d . . . . .
O3 O 0.9619(3) 0.6760(5) -0.0568(3) 0.0720(13) Uani 1 1 d . . . . .
O4 O 1.0603(3) 0.8148(5) -0.0470(2) 0.0672(12) Uani 1 1 d . . . . .
O5 O 0.5293(4) 0.3156(6) 0.7711(3) 0.0968(19) Uani 1 1 d . . . . .
O6 O 0.4551(4) 0.1484(7) 0.7622(3) 0.113(2) Uani 1 1 d . . . . .
O7 O 0.4459(3) 0.1955(6) 0.4321(3) 0.0923(18) Uani 1 1 d . . . . .
O8 O 0.5242(4) 0.3588(5) 0.4398(3) 0.104(2) Uani 1 1 d . . . . .
C1 C 0.9072(3) 0.8739(5) 0.1848(3) 0.0364(11) Uani 1 1 d . . . . .
C2 C 0.9786(3) 0.8063(5) 0.1815(3) 0.0378(11) Uani 1 1 d . . . . .
C3 C 1.0106(3) 0.7738(5) 0.1128(3) 0.0357(11) Uani 1 1 d . . . . .
C4 C 0.9679(3) 0.8095(5) 0.0472(3) 0.0318(10) Uani 1 1 d . . . . .
C5 C 0.8954(3) 0.8776(4) 0.0480(3) 0.0316(10) Uani 1 1 d . . . . .
C6 C 0.8651(3) 0.9123(4) 0.1185(3) 0.0338(11) Uani 1 1 d . . . . .
C7 C 0.7740(4) 1.1049(5) 0.1179(4) 0.0611(18) Uani 1 1 d . . . . .
H7 H 0.8127 1.1701 0.1127 0.073 Uiso 1 1 calc R U . . .
C8 C 0.6658(4) 1.0034(6) 0.1304(4) 0.067(2) Uani 1 1 d . . . . .
H8 H 0.6106 0.9867 0.1349 0.080 Uiso 1 1 calc R U . . .
C9 C 0.7739(4) 0.8880(9) -0.0412(4) 0.082(3) Uani 1 1 d . . . . .
H9 H 0.7356 0.8529 -0.0098 0.099 Uiso 1 1 calc R U . . .
C10 C 0.8322(4) 0.9653(8) -0.1333(4) 0.072(2) Uani 1 1 d . . . . .
H10 H 0.8406 0.9958 -0.1821 0.086 Uiso 1 1 calc R U . . .
C11 C 0.6098(3) 0.1102(5) 0.6661(3) 0.0372(11) Uani 1 1 d . . . . .
C12 C 0.5410(3) 0.1854(5) 0.6675(3) 0.0376(11) Uani 1 1 d . . . . .
C13 C 0.5039(3) 0.2348(5) 0.6016(3) 0.0375(11) Uani 1 1 d . . . . .
C14 C 0.5375(3) 0.2056(5) 0.5333(3) 0.0364(11) Uani 1 1 d . . . . .
C15 C 0.6073(3) 0.1323(4) 0.5304(3) 0.0336(11) Uani 1 1 d . . . . .
C16 C 0.6448(3) 0.0850(4) 0.5971(3) 0.0353(11) Uani 1 1 d . . . . .
C17 C 0.7415(4) -0.1013(6) 0.6128(4) 0.0660(19) Uani 1 1 d . . . . .
H17 H 0.7063 -0.1645 0.6299 0.079 Uiso 1 1 calc R U . . .
C18 C 0.8422(4) -0.0010(6) 0.5775(5) 0.081(2) Uani 1 1 d . . . . .
H18 H 0.8956 0.0165 0.5657 0.097 Uiso 1 1 calc R U . . .
C19 C 0.6877(4) 0.1825(7) 0.4170(4) 0.075(2) Uani 1 1 d D U . . .
H19 H 0.6982 0.2701 0.4263 0.090 Uiso 1 1 calc R U . . .
C20 C 0.6808(5) 0.0015(8) 0.3688(4) 0.082(2) Uani 1 1 d D U . . .
H20 H 0.6879 -0.0663 0.3346 0.099 Uiso 1 1 calc R U . . .


_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
Cl1 C1 1.717(5) . ?
Cl2 C3 1.704(5) . ?
Cl3 C11 1.717(5) . ?
Cl4 C13 1.713(5) . ?
N1 O2 1.196(7) . ?
N1 O1 1.201(7) . ?
N1 C2 1.489(7) . ?
N2 O3 1.207(6) . ?
N2 O4 1.208(6) . ?
N2 C4 1.478(6) . ?
N3 C9 1.331(7) . ?
N3 N4 1.359(6) . ?
N3 C5 1.410(6) . ?
N4 C10 1.306(8) . ?
N5 C9 1.322(8) . ?
N5 C10 1.339(8) . ?
N6 C7 1.313(7) . ?
N6 N7 1.356(6) . ?
N6 C6 1.421(6) . ?
N7 C8 1.297(7) . ?
N8 C7 1.315(7) . ?
N8 C8 1.338(8) . ?
N9 O6 1.158(7) . ?
N9 O5 1.187(7) . ?
N9 C12 1.495(7) . ?
N10 O7 1.172(6) . ?
N10 O8 1.203(7) . ?
N10 C14 1.474(7) . ?
N11 N12 1.328(7) . ?
N11 C19 1.346(8) . ?
N11 C15 1.417(6) . ?
N12 C20 1.302(8) . ?
N13 C19 1.303(9) . ?
N13 C20 1.316(10) . ?
N14 C17 1.331(7) . ?
N14 N15 1.356(6) . ?
N14 C16 1.408(6) . ?
N15 C18 1.284(8) . ?
N16 C17 1.310(8) . ?
N16 C18 1.352(9) . ?
C1 C2 1.366(7) . ?
C1 C6 1.382(7) . ?
C2 C3 1.381(7) . ?
C3 C4 1.367(7) . ?
C4 C5 1.382(6) . ?
C5 C6 1.402(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.371(7) . ?
C11 C16 1.390(7) . ?
C12 C13 1.377(7) . ?
C13 C14 1.377(7) . ?
C14 C15 1.375(7) . ?
C15 C16 1.384(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 2.043(10) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
O2 N1 O1 127.1(6) . . ?
O2 N1 C2 116.4(5) . . ?
O1 N1 C2 116.4(5) . . ?
O3 N2 O4 126.4(5) . . ?
O3 N2 C4 116.0(4) . . ?
O4 N2 C4 117.5(5) . . ?
C9 N3 N4 110.0(5) . . ?
C9 N3 C5 129.2(5) . . ?
N4 N3 C5 120.7(4) . . ?
C10 N4 N3 101.6(4) . . ?
C9 N5 C10 102.6(5) . . ?
C7 N6 N7 110.2(4) . . ?
C7 N6 C6 130.0(4) . . ?
N7 N6 C6 119.7(4) . . ?
C8 N7 N6 102.0(5) . . ?
C7 N8 C8 103.4(5) . . ?
O6 N9 O5 127.9(6) . . ?
O6 N9 C12 116.7(5) . . ?
O5 N9 C12 115.4(5) . . ?
O7 N10 O8 125.8(6) . . ?
O7 N10 C14 118.0(5) . . ?
O8 N10 C14 116.2(5) . . ?
N12 N11 C19 108.7(5) . . ?
N12 N11 C15 121.7(4) . . ?
C19 N11 C15 129.4(5) . . ?
C20 N12 N11 102.5(6) . . ?
C19 N13 C20 102.6(6) . . ?
C17 N14 N15 109.5(5) . . ?
C17 N14 C16 131.0(5) . . ?
N15 N14 C16 119.5(4) . . ?
C18 N15 N14 102.0(5) . . ?
C17 N16 C18 102.0(5) . . ?
C2 C1 C6 120.2(4) . . ?
C2 C1 Cl1 120.0(4) . . ?
C6 C1 Cl1 119.8(4) . . ?
C1 C2 C3 121.6(4) . . ?
C1 C2 N1 119.9(4) . . ?
C3 C2 N1 118.4(4) . . ?
C4 C3 C2 118.0(4) . . ?
C4 C3 Cl2 122.0(4) . . ?
C2 C3 Cl2 120.0(4) . . ?
C3 C4 C5 122.1(4) . . ?
C3 C4 N2 117.5(4) . . ?
C5 C4 N2 120.2(4) . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 N3 120.0(4) . . ?
C6 C5 N3 121.1(4) . . ?
C1 C6 C5 119.1(4) . . ?
C1 C6 N6 120.5(4) . . ?
C5 C6 N6 120.3(4) . . ?
N6 C7 N8 109.5(5) . . ?
N6 C7 H7 125.3 . . ?
N8 C7 H7 125.3 . . ?
N7 C8 N8 114.9(5) . . ?
N7 C8 H8 122.6 . . ?
N8 C8 H8 122.6 . . ?
N5 C9 N3 109.7(6) . . ?
N5 C9 H9 125.1 . . ?
N3 C9 H9 125.1 . . ?
N4 C10 N5 116.0(6) . . ?
N4 C10 H10 122.0 . . ?
N5 C10 H10 122.0 . . ?
C12 C11 C16 119.8(4) . . ?
C12 C11 Cl3 119.8(4) . . ?
C16 C11 Cl3 120.4(4) . . ?
C11 C12 C13 121.6(5) . . ?
C11 C12 N9 120.3(5) . . ?
C13 C12 N9 118.1(5) . . ?
C12 C13 C14 118.1(4) . . ?
C12 C13 Cl4 120.4(4) . . ?
C14 C13 Cl4 121.5(4) . . ?
C15 C14 C13 121.6(4) . . ?
C15 C14 N10 119.8(4) . . ?
C13 C14 N10 118.7(4) . . ?
C14 C15 C16 119.8(4) . . ?
C14 C15 N11 120.2(4) . . ?
C16 C15 N11 120.0(4) . . ?
C15 C16 C11 119.1(4) . . ?
C15 C16 N14 119.4(4) . . ?
C11 C16 N14 121.3(4) . . ?
N16 C17 N14 110.2(6) . . ?
N16 C17 H17 124.9 . . ?
N14 C17 H17 124.9 . . ?
N15 C18 N16 116.2(6) . . ?
N15 C18 H18 121.9 . . ?
N16 C18 H18 121.9 . . ?
N13 C19 N11 110.0(6) . . ?
N13 C19 C20 38.9(4) . . ?
N11 C19 C20 71.2(4) . . ?
N13 C19 H19 125.0 . . ?
N11 C19 H19 125.0 . . ?
C20 C19 H19 163.7 . . ?
N12 C20 N13 116.0(6) . . ?
N12 C20 C19 77.6(4) . . ?
N13 C20 C19 38.5(4) . . ?
N12 C20 H20 122.0 . . ?
N13 C20 H20 122.0 . . ?
C19 C20 H20 160.4 . . ?

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
C9 N3 N4 C10 0.1(8) . . . . ?
C5 N3 N4 C10 176.6(6) . . . . ?
C7 N6 N7 C8 1.7(7) . . . . ?
C6 N6 N7 C8 -179.6(5) . . . . ?
C19 N11 N12 C20 1.7(8) . . . . ?
C15 N11 N12 C20 -173.5(6) . . . . ?
C17 N14 N15 C18 -1.2(8) . . . . ?
C16 N14 N15 C18 178.1(6) . . . . ?
C6 C1 C2 C3 -0.3(7) . . . . ?
Cl1 C1 C2 C3 178.8(4) . . . . ?
C6 C1 C2 N1 -179.2(5) . . . . ?
Cl1 C1 C2 N1 -0.1(7) . . . . ?
O2 N1 C2 C1 87.6(7) . . . . ?
O1 N1 C2 C1 -95.4(7) . . . . ?
O2 N1 C2 C3 -91.4(6) . . . . ?
O1 N1 C2 C3 85.6(7) . . . . ?
C1 C2 C3 C4 -1.1(8) . . . . ?
N1 C2 C3 C4 177.9(5) . . . . ?
C1 C2 C3 Cl2 179.7(4) . . . . ?
N1 C2 C3 Cl2 -1.4(7) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
Cl2 C3 C4 C5 -179.9(4) . . . . ?
C2 C3 C4 N2 -174.8(4) . . . . ?
Cl2 C3 C4 N2 4.4(7) . . . . ?
O3 N2 C4 C3 104.7(6) . . . . ?
O4 N2 C4 C3 -72.4(6) . . . . ?
O3 N2 C4 C5 -71.1(6) . . . . ?
O4 N2 C4 C5 111.8(5) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
N2 C4 C5 C6 176.2(4) . . . . ?
C3 C4 C5 N3 -177.7(4) . . . . ?
N2 C4 C5 N3 -2.1(7) . . . . ?
C9 N3 C5 C4 129.1(7) . . . . ?
N4 N3 C5 C4 -46.6(7) . . . . ?
C9 N3 C5 C6 -49.1(9) . . . . ?
N4 N3 C5 C6 135.2(5) . . . . ?
C2 C1 C6 C5 1.8(7) . . . . ?
Cl1 C1 C6 C5 -177.3(3) . . . . ?
C2 C1 C6 N6 178.3(4) . . . . ?
Cl1 C1 C6 N6 -0.8(6) . . . . ?
C4 C5 C6 C1 -2.0(7) . . . . ?
N3 C5 C6 C1 176.3(4) . . . . ?
C4 C5 C6 N6 -178.4(4) . . . . ?
N3 C5 C6 N6 -0.2(7) . . . . ?
C7 N6 C6 C1 97.1(7) . . . . ?
N7 N6 C6 C1 -81.3(6) . . . . ?
C7 N6 C6 C5 -86.4(8) . . . . ?
N7 N6 C6 C5 95.2(6) . . . . ?
N7 N6 C7 N8 -1.7(8) . . . . ?
C6 N6 C7 N8 179.8(6) . . . . ?
C8 N8 C7 N6 0.8(9) . . . . ?
N6 N7 C8 N8 -1.3(9) . . . . ?
C7 N8 C8 N7 0.3(10) . . . . ?
C10 N5 C9 N3 1.4(11) . . . . ?
N4 N3 C9 N5 -1.0(10) . . . . ?
C5 N3 C9 N5 -177.1(7) . . . . ?
N3 N4 C10 N5 0.8(9) . . . . ?
C9 N5 C10 N4 -1.4(11) . . . . ?
C16 C11 C12 C13 1.5(7) . . . . ?
Cl3 C11 C12 C13 178.2(4) . . . . ?
C16 C11 C12 N9 -177.3(4) . . . . ?
Cl3 C11 C12 N9 -0.7(7) . . . . ?
O6 N9 C12 C11 -92.1(7) . . . . ?
O5 N9 C12 C11 90.5(7) . . . . ?
O6 N9 C12 C13 89.0(8) . . . . ?
O5 N9 C12 C13 -88.4(7) . . . . ?
C11 C12 C13 C14 0.6(7) . . . . ?
N9 C12 C13 C14 179.5(4) . . . . ?
C11 C12 C13 Cl4 -178.9(4) . . . . ?
N9 C12 C13 Cl4 0.0(6) . . . . ?
C12 C13 C14 C15 -1.8(7) . . . . ?
Cl4 C13 C14 C15 177.7(4) . . . . ?
C12 C13 C14 N10 179.6(4) . . . . ?
Cl4 C13 C14 N10 -0.9(7) . . . . ?
O7 N10 C14 C15 93.5(7) . . . . ?
O8 N10 C14 C15 -85.0(7) . . . . ?
O7 N10 C14 C13 -87.8(7) . . . . ?
O8 N10 C14 C13 93.7(7) . . . . ?
C13 C14 C15 C16 0.8(7) . . . . ?
N10 C14 C15 C16 179.4(4) . . . . ?
C13 C14 C15 N11 -178.8(4) . . . . ?
N10 C14 C15 N11 -0.2(7) . . . . ?
N12 N11 C15 C14 -106.3(7) . . . . ?
C19 N11 C15 C14 79.6(8) . . . . ?
N12 N11 C15 C16 74.1(7) . . . . ?
C19 N11 C15 C16 -100.0(7) . . . . ?
C14 C15 C16 C11 1.4(7) . . . . ?
N11 C15 C16 C11 -179.0(4) . . . . ?
C14 C15 C16 N14 -174.3(4) . . . . ?
N11 C15 C16 N14 5.3(7) . . . . ?
C12 C11 C16 C15 -2.5(7) . . . . ?
Cl3 C11 C16 C15 -179.1(4) . . . . ?
C12 C11 C16 N14 173.1(4) . . . . ?
Cl3 C11 C16 N14 -3.6(6) . . . . ?
C17 N14 C16 C15 -118.5(7) . . . . ?
N15 N14 C16 C15 62.4(7) . . . . ?
C17 N14 C16 C11 65.9(8) . . . . ?
N15 N14 C16 C11 -113.2(6) . . . . ?
C18 N16 C17 N14 -0.5(9) . . . . ?
N15 N14 C17 N16 1.1(8) . . . . ?
C16 N14 C17 N16 -178.1(6) . . . . ?
N14 N15 C18 N16 0.9(10) . . . . ?
C17 N16 C18 N15 -0.3(11) . . . . ?
C20 N13 C19 N11 3.7(9) . . . . ?
N12 N11 C19 N13 -3.6(9) . . . . ?
C15 N11 C19 N13 171.1(6) . . . . ?
N12 N11 C19 C20 -1.1(6) . . . . ?
C15 N11 C19 C20 173.6(6) . . . . ?
N11 N12 C20 N13 0.7(10) . . . . ?
N11 N12 C20 C19 -1.1(5) . . . . ?
C19 N13 C20 N12 -2.8(11) . . . . ?

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
C17 H17 N7 0.93 2.55 3.225(7) 129.9 4_566
C9 H9 N7 0.93 2.57 3.202(10) 125.6 .
C8 H8 O6 0.93 2.56 3.211(8) 127.4 3_666
C7 H7 O4 0.93 2.44 3.158(7) 134.1 3_775
C7 H7 N15 0.93 2.65 3.296(7) 127.2 4_575
C17 H17 N7 0.93 2.55 3.225(7) 129.9 4_566
C9 H9 N7 0.93 2.57 3.202(10) 125.6 .
C8 H8 O6 0.93 2.56 3.211(8) 127.4 3_666
C7 H7 O4 0.93 2.44 3.158(7) 134.1 3_775
C7 H7 N15 0.93 2.65 3.296(7) 127.2 4_575
C7 H7 N15 0.93 2.65 3.296(7) 127.2 4_575
C7 H7 O4 0.93 2.44 3.158(7) 134.1 3_775
C8 H8 O6 0.93 2.56 3.211(8) 127.4 3_666
C9 H9 N7 0.93 2.57 3.202(10) 125.6 .
C17 H17 N7 0.93 2.55 3.225(7) 129.9 4_566
C7 H7 N15 0.93 2.65 3.296(7) 127.2 4_575
C7 H7 O4 0.93 2.44 3.158(7) 134.1 3_775
C8 H8 O6 0.93 2.56 3.211(8) 127.4 3_666
C9 H9 N7 0.93 2.57 3.202(10) 125.6 .
C17 H17 N7 0.93 2.55 3.225(7) 129.9 4_566

_refine_diff_density_max         0.544
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.098

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd16194
_database_code_depnum_ccdc_archive 'CCDC 1552454'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H2 N14 O4'
_chemical_formula_weight         358.24

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/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                   11.5557(18)
_cell_length_b                   11.6416(19)
_cell_length_c                   11.1129(17)
_cell_angle_alpha                90
_cell_angle_beta                 116.222(3)
_cell_angle_gamma                90
_cell_volume                     1341.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1571
_cell_measurement_theta_min      5.262
_cell_measurement_theta_max      46.558

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6793
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7543
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.964
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2497
_reflns_number_gt                1946
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0555P)²+0.3625P] 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         2497
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
O1 O 0.53502(19) 1.03017(17) 0.16339(18) 0.0626(6) Uani 1 1 d . . . . .
O2 O 0.63397(17) 1.10328(16) 0.35846(19) 0.0553(5) Uani 1 1 d . . . . .
O3 O 0.68218(18) 0.65058(18) 0.5847(2) 0.0676(6) Uani 1 1 d . . . . .
O4 O 0.62511(18) 0.74732(19) 0.71357(17) 0.0654(6) Uani 1 1 d . . . . .
N1 N 0.30405(18) 0.99924(17) 0.16866(19) 0.0416(5) Uani 1 1 d . . . . .
N2 N 0.1980(2) 1.03122(18) 0.15828(19) 0.0459(5) Uani 1 1 d . . . . .
N3 N 0.1018(2) 1.0695(3) 0.1350(3) 0.0771(8) Uani 1 1 d . . . . .
N4 N 0.56255(17) 1.03274(16) 0.28151(19) 0.0362(4) Uani 1 1 d . . . . .
N5 N 0.72599(17) 0.88954(18) 0.52118(19) 0.0434(5) Uani 1 1 d . . . . .
N6 N 0.79104(17) 0.92346(18) 0.46470(19) 0.0433(5) Uani 1 1 d . . . . .
N7 N 0.8623(2) 0.9512(2) 0.4290(2) 0.0658(7) Uani 1 1 d . . . . .
N8 N 0.62090(17) 0.72459(18) 0.60535(19) 0.0404(5) Uani 1 1 d . . . . .
N9 N 0.36461(17) 0.68275(16) 0.48789(17) 0.0369(4) Uani 1 1 d . . . . .
N10 N 0.26609(18) 0.62941(16) 0.41479(19) 0.0370(4) Uani 1 1 d . . . . .
N11 N 0.1811(2) 0.5717(2) 0.3650(2) 0.0582(6) Uani 1 1 d . . . . .
N12 N 0.19126(15) 0.81814(16) 0.25888(17) 0.0324(4) Uani 1 1 d . . . . .
N13 N 0.11659(17) 0.84639(18) 0.32164(19) 0.0432(5) Uani 1 1 d . . . . .
N14 N -0.00217(18) 0.7655(2) 0.1201(2) 0.0546(6) Uani 1 1 d . . . . .
C1 C 0.37733(19) 0.92582(18) 0.27529(19) 0.0303(5) Uani 1 1 d . . . . .
C2 C 0.51093(19) 0.94291(18) 0.3356(2) 0.0300(5) Uani 1 1 d . . . . .
C3 C 0.59245(19) 0.87856(19) 0.4456(2) 0.0318(5) Uani 1 1 d . . . . .
C4 C 0.53589(19) 0.79530(18) 0.49128(19) 0.0312(5) Uani 1 1 d . . . . .
C5 C 0.40498(19) 0.77163(18) 0.43033(19) 0.0300(5) Uani 1 1 d . . . . .
C6 C 0.32601(18) 0.83906(18) 0.3214(2) 0.0287(5) Uani 1 1 d . . . . .
C7 C 0.0031(2) 0.8129(2) 0.2331(3) 0.0530(7) Uani 1 1 d . . . . .
H7 H -0.0701 0.8213 0.2471 0.064 Uiso 1 1 calc R U . . .
C8 C 0.1170(2) 0.7699(2) 0.1398(2) 0.0429(6) Uani 1 1 d . . . . .
H8 H 0.1469 0.7434 0.0797 0.051 Uiso 1 1 calc R U . . .


_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 N4 1.207(2) . ?
O2 N4 1.210(2) . ?
O3 N8 1.200(3) . ?
O4 N8 1.211(2) . ?
N1 N2 1.237(3) . ?
N1 C1 1.402(3) . ?
N2 N3 1.117(3) . ?
N4 C2 1.459(3) . ?
N5 N6 1.238(3) . ?
N5 C3 1.399(3) . ?
N6 N7 1.109(3) . ?
N8 C4 1.466(3) . ?
N9 N10 1.235(3) . ?
N9 C5 1.400(3) . ?
N10 N11 1.114(3) . ?
N12 C8 1.341(3) . ?
N12 N13 1.368(2) . ?
N12 C6 1.418(3) . ?
N13 C7 1.304(3) . ?
N14 C8 1.297(3) . ?
N14 C7 1.348(3) . ?
C1 C6 1.379(3) . ?
C1 C2 1.399(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.392(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

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 N1 C1 117.77(18) . . ?
N3 N2 N1 170.4(3) . . ?
O1 N4 O2 123.7(2) . . ?
O1 N4 C2 118.12(18) . . ?
O2 N4 C2 118.09(18) . . ?
N6 N5 C3 118.71(18) . . ?
N7 N6 N5 171.2(2) . . ?
O3 N8 O4 125.3(2) . . ?
O3 N8 C4 117.7(2) . . ?
O4 N8 C4 117.0(2) . . ?
N10 N9 C5 117.87(18) . . ?
N11 N10 N9 169.8(2) . . ?
C8 N12 N13 109.34(17) . . ?
C8 N12 C6 129.82(18) . . ?
N13 N12 C6 120.83(16) . . ?
C7 N13 N12 101.20(19) . . ?
C8 N14 C7 102.7(2) . . ?
C6 C1 C2 119.38(19) . . ?
C6 C1 N1 124.21(19) . . ?
C2 C1 N1 116.41(19) . . ?
C3 C2 C1 121.42(19) . . ?
C3 C2 N4 120.53(18) . . ?
C1 C2 N4 118.04(18) . . ?
C4 C3 C2 117.01(18) . . ?
C4 C3 N5 114.68(19) . . ?
C2 C3 N5 128.3(2) . . ?
C5 C4 C3 123.40(19) . . ?
C5 C4 N8 118.76(18) . . ?
C3 C4 N8 117.75(18) . . ?
C4 C5 C6 117.89(19) . . ?
C4 C5 N9 115.85(18) . . ?
C6 C5 N9 126.24(18) . . ?
C1 C6 C5 120.77(18) . . ?
C1 C6 N12 120.20(18) . . ?
C5 C6 N12 119.02(18) . . ?
N13 C7 N14 116.2(2) . . ?
N13 C7 H7 121.9 . . ?
N14 C7 H7 121.9 . . ?
N14 C8 N12 110.6(2) . . ?
N14 C8 H8 124.7 . . ?
N12 C8 H8 124.7 . . ?

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
C5 N9 N10 N11 176.4(13) . . . . ?
C8 N12 N13 C7 -0.4(3) . . . . ?
C6 N12 N13 C7 -179.4(2) . . . . ?
N2 N1 C1 C6 37.8(3) . . . . ?
N2 N1 C1 C2 -143.0(2) . . . . ?
C6 C1 C2 C3 -3.5(3) . . . . ?
N1 C1 C2 C3 177.3(2) . . . . ?
C6 C1 C2 N4 177.90(18) . . . . ?
N1 C1 C2 N4 -1.3(3) . . . . ?
O1 N4 C2 C3 126.8(2) . . . . ?
O2 N4 C2 C3 -50.7(3) . . . . ?
O1 N4 C2 C1 -54.6(3) . . . . ?
O2 N4 C2 C1 127.8(2) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
N4 C2 C3 C4 179.70(18) . . . . ?
C1 C2 C3 N5 -176.1(2) . . . . ?
N4 C2 C3 N5 2.5(3) . . . . ?
N6 N5 C3 C4 151.4(2) . . . . ?
N6 N5 C3 C2 -31.4(3) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
N5 C3 C4 C5 179.83(19) . . . . ?
C2 C3 C4 N8 178.55(19) . . . . ?
N5 C3 C4 N8 -3.8(3) . . . . ?
O3 N8 C4 C5 101.1(2) . . . . ?
O4 N8 C4 C5 -80.2(3) . . . . ?
O3 N8 C4 C3 -75.4(3) . . . . ?
O4 N8 C4 C3 103.3(2) . . . . ?
C3 C4 C5 C6 -3.1(3) . . . . ?
N8 C4 C5 C6 -179.42(19) . . . . ?
C3 C4 C5 N9 178.50(19) . . . . ?
N8 C4 C5 N9 2.2(3) . . . . ?
N10 N9 C5 C4 -152.95(19) . . . . ?
N10 N9 C5 C6 28.9(3) . . . . ?
C2 C1 C6 C5 2.6(3) . . . . ?
N1 C1 C6 C5 -178.27(19) . . . . ?
C2 C1 C6 N12 -178.06(18) . . . . ?
N1 C1 C6 N12 1.1(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
N9 C5 C6 C1 178.80(19) . . . . ?
C4 C5 C6 N12 -178.73(18) . . . . ?
N9 C5 C6 N12 -0.6(3) . . . . ?
C8 N12 C6 C1 73.4(3) . . . . ?
N13 N12 C6 C1 -107.8(2) . . . . ?
C8 N12 C6 C5 -107.3(3) . . . . ?
N13 N12 C6 C5 71.5(3) . . . . ?
N12 N13 C7 N14 0.3(3) . . . . ?
C8 N14 C7 N13 -0.1(3) . . . . ?
C7 N14 C8 N12 -0.2(3) . . . . ?
N13 N12 C8 N14 0.4(3) . . . . ?
C6 N12 C8 N14 179.3(2) . . . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd16469
_database_code_depnum_ccdc_archive 'CCDC 1552456'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 N10 O4'
_chemical_formula_weight         332.26

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/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                   8.941(3)
_cell_length_b                   7.445(3)
_cell_length_c                   20.759(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.328(15)
_cell_angle_gamma                90
_cell_volume                     1326.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    509
_cell_measurement_theta_min      4.747
_cell_measurement_theta_max      39.658

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6267
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7331
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.045
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2456
_reflns_number_gt                1430
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0574P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2456
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_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
N1 N 0.6391(3) 0.1625(3) 0.13308(10) 0.0301(6) Uani 1 1 d . . . . .
N2 N 0.5398(3) 0.0266(4) 0.13734(12) 0.0443(7) Uani 1 1 d . . . . .
N3 N 0.6335(3) 0.1640(4) 0.23724(12) 0.0449(7) Uani 1 1 d . . . . .
N4 N 0.4033(3) 0.2320(4) 0.02045(16) 0.0419(7) Uani 1 1 d . . . . .
N5 N 0.4586(3) 0.3580(3) -0.10076(11) 0.0364(6) Uani 1 1 d . . . . .
N6 N 0.7745(3) 0.3631(4) -0.10320(12) 0.0541(8) Uani 1 1 d . . . . .
H6A H 0.8698 0.3632 -0.1045 0.065 Uiso 1 1 calc R U . . .
H6B H 0.7015 0.3960 -0.1379 0.065 Uiso 1 1 calc R U . . .
N7 N 1.0180(3) 0.2393(4) 0.00657(12) 0.0360(6) Uani 1 1 d . . . . .
N8 N 0.9422(3) 0.1677(3) 0.12809(11) 0.0343(6) Uani 1 1 d . . . . .
N9 N 1.0470(3) 0.2973(4) 0.15763(13) 0.0493(7) Uani 1 1 d . . . . .
N10 N 1.0973(4) 0.0343(5) 0.21333(15) 0.0691(9) Uani 1 1 d . . . . .
O1 O 0.3245(3) 0.3633(4) -0.09662(10) 0.0610(8) Uani 1 1 d . . . . .
O2 O 0.4836(2) 0.3994(3) -0.15336(10) 0.0580(7) Uani 1 1 d . . . . .
O3 O 1.0609(3) 0.3248(4) -0.03375(12) 0.0623(7) Uani 1 1 d . . . . .
O4 O 1.1022(2) 0.1296(3) 0.04463(11) 0.0543(7) Uani 1 1 d . . . . .
C1 C 0.6717(3) 0.2005(4) 0.07142(12) 0.0279(7) Uani 1 1 d . . . . .
C2 C 0.5463(3) 0.2446(4) 0.01427(13) 0.0280(7) Uani 1 1 d . . . . .
C3 C 0.5830(3) 0.3051(4) -0.04400(13) 0.0291(7) Uani 1 1 d . . . . .
C4 C 0.7404(3) 0.3127(4) -0.04820(13) 0.0323(7) Uani 1 1 d . . . . .
C5 C 0.8583(3) 0.2580(4) 0.00959(14) 0.0315(7) Uani 1 1 d . . . . .
C6 C 0.8221(3) 0.2063(4) 0.06842(13) 0.0282(7) Uani 1 1 d . . . . .
C7 C 0.6926(3) 0.2417(4) 0.19327(13) 0.0375(8) Uani 1 1 d . . . . .
H7 H 0.7617 0.3380 0.2025 0.045 Uiso 1 1 calc R U . . .
C8 C 0.5415(4) 0.0351(5) 0.20038(15) 0.0483(9) Uani 1 1 d . . . . .
H8 H 0.4831 -0.0426 0.2188 0.058 Uiso 1 1 calc R U . . .
C9 C 0.9759(4) 0.0148(5) 0.16200(16) 0.0512(9) Uani 1 1 d . . . . .
H9 H 0.9202 -0.0916 0.1506 0.061 Uiso 1 1 calc R U . . .
C10 C 1.1351(4) 0.2078(6) 0.20822(18) 0.0645(11) Uani 1 1 d . . . . .
H10 H 1.2195 0.2609 0.2391 0.077 Uiso 1 1 calc R U . . .
H4B H 0.332(4) 0.252(4) -0.0149(15) 0.032(9) Uiso 1 1 d . . . . .
H4A H 0.396(4) 0.175(4) 0.0584(17) 0.053(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
N1 C7 1.342(3) . ?
N1 N2 1.365(3) . ?
N1 C1 1.419(3) . ?
N2 C8 1.306(4) . ?
N3 C7 1.311(4) . ?
N3 C8 1.353(4) . ?
N4 C2 1.324(4) . ?
N4 H4B 0.84(3) . ?
N4 H4A 0.91(3) . ?
N5 O2 1.214(3) . ?
N5 O1 1.227(3) . ?
N5 C3 1.430(3) . ?
N6 C4 1.316(3) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 O3 1.197(3) . ?
N7 O4 1.234(3) . ?
N7 C5 1.454(4) . ?
N8 C9 1.328(4) . ?
N8 N9 1.365(3) . ?
N8 C6 1.422(3) . ?
N9 C10 1.305(4) . ?
N10 C9 1.298(4) . ?
N10 C10 1.347(5) . ?
C1 C6 1.365(4) . ?
C1 C2 1.423(4) . ?
C2 C3 1.413(4) . ?
C3 C4 1.435(4) . ?
C4 C5 1.416(4) . ?
C5 C6 1.402(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?

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
C7 N1 N2 109.5(2) . . ?
C7 N1 C1 130.0(2) . . ?
N2 N1 C1 120.5(2) . . ?
C8 N2 N1 101.8(2) . . ?
C7 N3 C8 102.7(2) . . ?
C2 N4 H4B 115(2) . . ?
C2 N4 H4A 115(2) . . ?
H4B N4 H4A 128(3) . . ?
O2 N5 O1 119.0(2) . . ?
O2 N5 C3 121.0(2) . . ?
O1 N5 C3 120.0(2) . . ?
C4 N6 H6A 120.0 . . ?
C4 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
O3 N7 O4 122.8(3) . . ?
O3 N7 C5 119.4(3) . . ?
O4 N7 C5 117.7(3) . . ?
C9 N8 N9 110.1(2) . . ?
C9 N8 C6 129.7(3) . . ?
N9 N8 C6 120.2(2) . . ?
C10 N9 N8 100.6(3) . . ?
C9 N10 C10 102.3(3) . . ?
C6 C1 N1 120.2(2) . . ?
C6 C1 C2 120.7(2) . . ?
N1 C1 C2 119.0(2) . . ?
N4 C2 C3 124.7(3) . . ?
N4 C2 C1 117.3(3) . . ?
C3 C2 C1 118.0(2) . . ?
C2 C3 N5 118.6(2) . . ?
C2 C3 C4 122.2(2) . . ?
N5 C3 C4 119.2(2) . . ?
N6 C4 C5 121.2(3) . . ?
N6 C4 C3 122.3(3) . . ?
C5 C4 C3 116.5(2) . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 N7 118.8(2) . . ?
C4 C5 N7 119.8(2) . . ?
C1 C6 C5 121.3(2) . . ?
C1 C6 N8 117.8(2) . . ?
C5 C6 N8 120.8(2) . . ?
N3 C7 N1 110.3(3) . . ?
N3 C7 H7 124.9 . . ?
N1 C7 H7 124.9 . . ?
N2 C8 N3 115.8(3) . . ?
N2 C8 H8 122.1 . . ?
N3 C8 H8 122.1 . . ?
N10 C9 N8 110.6(3) . . ?
N10 C9 H9 124.7 . . ?
N8 C9 H9 124.7 . . ?
N9 C10 N10 116.4(3) . . ?
N9 C10 H10 121.8 . . ?
N10 C10 H10 121.8 . . ?

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
C7 N1 N2 C8 0.0(3) . . . . ?
C1 N1 N2 C8 179.9(3) . . . . ?
C9 N8 N9 C10 -0.6(3) . . . . ?
C6 N8 N9 C10 -178.9(3) . . . . ?
C7 N1 C1 C6 53.7(4) . . . . ?
N2 N1 C1 C6 -126.1(3) . . . . ?
C7 N1 C1 C2 -121.9(3) . . . . ?
N2 N1 C1 C2 58.3(4) . . . . ?
C6 C1 C2 N4 178.5(3) . . . . ?
N1 C1 C2 N4 -5.9(4) . . . . ?
C6 C1 C2 C3 -3.9(4) . . . . ?
N1 C1 C2 C3 171.7(2) . . . . ?
N4 C2 C3 N5 0.4(4) . . . . ?
C1 C2 C3 N5 -177.1(3) . . . . ?
N4 C2 C3 C4 -178.8(3) . . . . ?
C1 C2 C3 C4 3.8(4) . . . . ?
O2 N5 C3 C2 -175.0(3) . . . . ?
O1 N5 C3 C2 5.4(4) . . . . ?
O2 N5 C3 C4 4.2(4) . . . . ?
O1 N5 C3 C4 -175.3(3) . . . . ?
C2 C3 C4 N6 177.6(3) . . . . ?
N5 C3 C4 N6 -1.6(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
N5 C3 C4 C5 -179.8(3) . . . . ?
N6 C4 C5 C6 179.2(3) . . . . ?
C3 C4 C5 C6 -2.5(4) . . . . ?
N6 C4 C5 N7 -6.3(4) . . . . ?
C3 C4 C5 N7 172.0(3) . . . . ?
O3 N7 C5 C6 -159.7(3) . . . . ?
O4 N7 C5 C6 22.9(4) . . . . ?
O3 N7 C5 C4 25.7(4) . . . . ?
O4 N7 C5 C4 -151.7(3) . . . . ?
N1 C1 C6 C5 -174.7(2) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
N1 C1 C6 N8 2.0(4) . . . . ?
C2 C1 C6 N8 177.5(2) . . . . ?
C4 C5 C6 C1 2.5(4) . . . . ?
N7 C5 C6 C1 -172.1(3) . . . . ?
C4 C5 C6 N8 -174.1(3) . . . . ?
N7 C5 C6 N8 11.4(4) . . . . ?
C9 N8 C6 C1 66.7(4) . . . . ?
N9 N8 C6 C1 -115.5(3) . . . . ?
C9 N8 C6 C5 -116.7(4) . . . . ?
N9 N8 C6 C5 61.2(4) . . . . ?
C8 N3 C7 N1 -0.3(3) . . . . ?
N2 N1 C7 N3 0.2(3) . . . . ?
C1 N1 C7 N3 -179.6(3) . . . . ?
N1 N2 C8 N3 -0.2(4) . . . . ?
C7 N3 C8 N2 0.3(4) . . . . ?
C10 N10 C9 N8 -0.2(4) . . . . ?
N9 N8 C9 N10 0.5(4) . . . . ?
C6 N8 C9 N10 178.6(3) . . . . ?
N8 N9 C10 N10 0.5(4) . . . . ?
C9 N10 C10 N9 -0.2(5) . . . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd16258
_database_code_depnum_ccdc_archive 'CCDC 1552453'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 N16 O8'
_chemical_formula_weight         560.45

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      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                   7.4815(11)
_cell_length_b                   9.2466(13)
_cell_length_c                   16.151(3)
_cell_angle_alpha                87.286(4)
_cell_angle_beta                 87.725(3)
_cell_angle_gamma                89.891(3)
_cell_volume                     1115.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1742
_cell_measurement_theta_min      5.054
_cell_measurement_theta_max      54.567

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6290
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6451
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.489
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4134
_reflns_number_gt                3198
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0698P)²+0.1534P] 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         4134
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
N1 N -0.3441(3) 0.6019(2) 0.41863(12) 0.0479(5) Uani 1 1 d . . . . .
N2 N -0.1015(3) 0.4617(2) 0.39793(12) 0.0464(5) Uani 1 1 d . . . . .
N3 N -0.0953(2) 0.58104(18) 0.34522(10) 0.0303(4) Uani 1 1 d . . . . .
N4 N -0.1034(3) 0.4585(2) 0.19734(13) 0.0505(6) Uani 1 1 d . . . . .
H4A H -0.1882 0.4503 0.2348 0.061 Uiso 1 1 calc R U . . .
H4B H -0.1116 0.4156 0.1515 0.061 Uiso 1 1 calc R U . . .
N5 N 0.1859(3) 0.4794(2) 0.07721(12) 0.0435(5) Uani 1 1 d . . . . .
N6 N 0.4618(3) 0.6733(3) 0.10936(14) 0.0644(7) Uani 1 1 d . . . . .
H6A H 0.4634 0.6280 0.0640 0.077 Uiso 1 1 calc R U . . .
H6B H 0.5470 0.7321 0.1186 0.077 Uiso 1 1 calc R U . . .
N7 N 0.4533(2) 0.8320(2) 0.25421(11) 0.0365(4) Uani 1 1 d . . . . .
N8 N 0.1763(3) 0.7640(2) 0.37463(11) 0.0444(5) Uani 1 1 d . . . . .
H8A H 0.0893 0.7453 0.4099 0.053 Uiso 1 1 calc R U . . .
H8B H 0.2589 0.8236 0.3861 0.053 Uiso 1 1 calc R U . . .
N9 N -0.1904(2) -0.0330(2) 0.04561(11) 0.0405(5) Uani 1 1 d . . . . .
N10 N -0.0039(3) -0.1298(2) 0.13894(12) 0.0411(5) Uani 1 1 d . . . . .
N11 N -0.0212(2) 0.01624(18) 0.14704(10) 0.0300(4) Uani 1 1 d . . . . .
N12 N -0.1793(2) 0.0426(2) 0.29926(12) 0.0428(5) Uani 1 1 d . . . . .
H12A H -0.2310 0.0032 0.2594 0.051 Uiso 1 1 calc R U . . .
H12B H -0.2337 0.0471 0.3470 0.051 Uiso 1 1 calc R U . . .
N13 N 0.0014(3) 0.1612(2) 0.43202(11) 0.0371(4) Uani 1 1 d . . . . .
N14 N 0.3329(3) 0.2950(3) 0.39056(12) 0.0595(7) Uani 1 1 d . . . . .
H14A H 0.2857 0.2980 0.4399 0.071 Uiso 1 1 calc R U . . .
H14B H 0.4348 0.3354 0.3788 0.071 Uiso 1 1 calc R U . . .
N15 N 0.4871(2) 0.2926(2) 0.22961(11) 0.0409(5) Uani 1 1 d . . . . .
N16 N 0.3177(2) 0.1159(2) 0.11602(11) 0.0427(5) Uani 1 1 d . . . . .
H16A H 0.2615 0.0678 0.0809 0.051 Uiso 1 1 calc R U . . .
H16B H 0.4236 0.1481 0.1035 0.051 Uiso 1 1 calc R U . . .
O1 O 0.0648(2) 0.39326(19) 0.06497(11) 0.0560(5) Uani 1 1 d . . . . .
O2 O 0.3055(3) 0.4978(3) 0.02219(12) 0.0792(7) Uani 1 1 d . . . . .
O3 O 0.5816(2) 0.8554(2) 0.20310(10) 0.0573(5) Uani 1 1 d . . . . .
O4 O 0.4472(2) 0.90375(18) 0.31721(10) 0.0480(4) Uani 1 1 d . . . . .
O5 O -0.1556(2) 0.12388(19) 0.44633(10) 0.0547(5) Uani 1 1 d . . . . .
O6 O 0.0903(2) 0.2007(2) 0.49053(9) 0.0514(5) Uani 1 1 d . . . . .
O7 O 0.5554(2) 0.3753(2) 0.27818(11) 0.0716(7) Uani 1 1 d . . . . .
O8 O 0.5650(2) 0.2786(2) 0.16140(11) 0.0638(6) Uani 1 1 d . . . . .
C1 C -0.2535(3) 0.4814(3) 0.43940(15) 0.0463(6) Uani 1 1 d . . . . .
H1A H -0.2957 0.4154 0.4808 0.056 Uiso 1 1 calc R U . . .
C2 C -0.2400(3) 0.6611(3) 0.35953(14) 0.0416(6) Uani 1 1 d . . . . .
H2A H -0.2641 0.7483 0.3311 0.050 Uiso 1 1 calc R U . . .
C3 C 0.0486(3) 0.6049(2) 0.28509(12) 0.0305(5) Uani 1 1 d . . . . .
C4 C 0.0397(3) 0.5369(2) 0.21021(13) 0.0317(5) Uani 1 1 d . . . . .
C5 C 0.1861(3) 0.5554(2) 0.15048(13) 0.0335(5) Uani 1 1 d . . . . .
C6 C 0.3289(3) 0.6527(2) 0.16466(13) 0.0371(5) Uani 1 1 d . . . . .
C7 C 0.3241(3) 0.7282(2) 0.24069(12) 0.0308(5) Uani 1 1 d . . . . .
C8 C 0.1832(3) 0.7009(2) 0.30259(12) 0.0313(5) Uani 1 1 d . . . . .
C9 C -0.1077(3) -0.1517(3) 0.07789(14) 0.0422(6) Uani 1 1 d . . . . .
H9 H -0.1239 -0.2432 0.0578 0.051 Uiso 1 1 calc R U . . .
C10 C -0.1325(3) 0.0691(2) 0.09101(13) 0.0352(5) Uani 1 1 d . . . . .
H10 H -0.1649 0.1660 0.0849 0.042 Uiso 1 1 calc R U . . .
C11 C 0.0703(3) 0.0882(2) 0.20936(12) 0.0289(5) Uani 1 1 d . . . . .
C12 C -0.0158(3) 0.0965(2) 0.28717(12) 0.0302(5) Uani 1 1 d . . . . .
C13 C 0.0796(3) 0.1607(2) 0.35127(12) 0.0309(5) Uani 1 1 d . . . . .
C14 C 0.2493(3) 0.2287(2) 0.33320(13) 0.0333(5) Uani 1 1 d . . . . .
C15 C 0.3265(3) 0.2219(2) 0.25085(12) 0.0311(5) Uani 1 1 d . . . . .
C16 C 0.2411(3) 0.1404(2) 0.18942(12) 0.0295(5) 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
N1 C2 1.308(3) . ?
N1 C1 1.340(3) . ?
N2 C1 1.313(3) . ?
N2 N3 1.361(3) . ?
N3 C2 1.329(3) . ?
N3 C3 1.431(2) . ?
N4 C4 1.323(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 O1 1.236(2) . ?
N5 O2 1.242(2) . ?
N5 C5 1.404(3) . ?
N6 C6 1.318(3) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 O4 1.240(2) . ?
N7 O3 1.253(2) . ?
N7 C7 1.394(3) . ?
N8 C8 1.325(3) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 C10 1.307(3) . ?
N9 C9 1.352(3) . ?
N10 C9 1.303(3) . ?
N10 N11 1.368(2) . ?
N11 C10 1.329(3) . ?
N11 C11 1.430(2) . ?
N12 C12 1.325(3) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N13 O5 1.234(2) . ?
N13 O6 1.246(2) . ?
N13 C13 1.408(3) . ?
N14 C14 1.314(3) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
N15 O8 1.238(2) . ?
N15 O7 1.245(2) . ?
N15 C15 1.392(3) . ?
N16 C16 1.325(3) . ?
N16 H16A 0.8600 . ?
N16 H16B 0.8600 . ?
C1 H1A 0.9300 . ?
C2 H2A 0.9300 . ?
C3 C8 1.390(3) . ?
C3 C4 1.393(3) . ?
C4 C5 1.436(3) . ?
C5 C6 1.431(3) . ?
C6 C7 1.440(3) . ?
C7 C8 1.438(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.388(3) . ?
C11 C12 1.394(3) . ?
C12 C13 1.433(3) . ?
C13 C14 1.432(3) . ?
C14 C15 1.433(3) . ?
C15 C16 1.443(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
C2 N1 C1 101.80(19) . . ?
C1 N2 N3 101.54(19) . . ?
C2 N3 N2 108.93(18) . . ?
C2 N3 C3 129.31(19) . . ?
N2 N3 C3 121.75(17) . . ?
C4 N4 H4A 120.0 . . ?
C4 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
O1 N5 O2 117.77(18) . . ?
O1 N5 C5 120.82(18) . . ?
O2 N5 C5 121.40(19) . . ?
C6 N6 H6A 120.0 . . ?
C6 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
O4 N7 O3 117.33(17) . . ?
O4 N7 C7 121.66(17) . . ?
O3 N7 C7 121.01(17) . . ?
C8 N8 H8A 120.0 . . ?
C8 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C10 N9 C9 102.19(18) . . ?
C9 N10 N11 101.89(19) . . ?
C10 N11 N10 109.01(17) . . ?
C10 N11 C11 129.89(18) . . ?
N10 N11 C11 121.09(17) . . ?
C12 N12 H12A 120.0 . . ?
C12 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
O5 N13 O6 118.72(17) . . ?
O5 N13 C13 121.19(17) . . ?
O6 N13 C13 120.08(18) . . ?
C14 N14 H14A 120.0 . . ?
C14 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
O8 N15 O7 117.57(18) . . ?
O8 N15 C15 121.55(17) . . ?
O7 N15 C15 120.85(17) . . ?
C16 N16 H16A 120.0 . . ?
C16 N16 H16B 120.0 . . ?
H16A N16 H16B 120.0 . . ?
N2 C1 N1 116.2(2) . . ?
N2 C1 H1A 121.9 . . ?
N1 C1 H1A 121.9 . . ?
N1 C2 N3 111.5(2) . . ?
N1 C2 H2A 124.2 . . ?
N3 C2 H2A 124.2 . . ?
C8 C3 C4 123.80(18) . . ?
C8 C3 N3 118.31(17) . . ?
C4 C3 N3 117.78(18) . . ?
N4 C4 C3 118.53(19) . . ?
N4 C4 C5 123.00(18) . . ?
C3 C4 C5 118.47(18) . . ?
N5 C5 C6 120.29(19) . . ?
N5 C5 C4 119.42(18) . . ?
C6 C5 C4 120.27(18) . . ?
N6 C6 C5 120.9(2) . . ?
N6 C6 C7 120.6(2) . . ?
C5 C6 C7 118.52(18) . . ?
N7 C7 C8 119.06(17) . . ?
N7 C7 C6 120.33(18) . . ?
C8 C7 C6 120.58(18) . . ?
N8 C8 C3 119.20(19) . . ?
N8 C8 C7 122.79(18) . . ?
C3 C8 C7 118.01(17) . . ?
N10 C9 N9 115.7(2) . . ?
N10 C9 H9 122.1 . . ?
N9 C9 H9 122.1 . . ?
N9 C10 N11 111.2(2) . . ?
N9 C10 H10 124.4 . . ?
N11 C10 H10 124.4 . . ?
C16 C11 C12 124.35(18) . . ?
C16 C11 N11 117.92(17) . . ?
C12 C11 N11 117.69(18) . . ?
N12 C12 C11 119.15(18) . . ?
N12 C12 C13 122.93(19) . . ?
C11 C12 C13 117.90(18) . . ?
N13 C13 C14 120.09(17) . . ?
N13 C13 C12 119.20(18) . . ?
C14 C13 C12 120.67(18) . . ?
N14 C14 C13 121.04(19) . . ?
N14 C14 C15 120.75(19) . . ?
C13 C14 C15 118.21(17) . . ?
N15 C15 C14 120.02(17) . . ?
N15 C15 C16 119.18(17) . . ?
C14 C15 C16 120.80(18) . . ?
N16 C16 C11 119.80(18) . . ?
N16 C16 C15 122.97(18) . . ?
C11 C16 C15 117.23(17) . . ?

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 C2 0.5(2) . . . . ?
C1 N2 N3 C3 -178.47(18) . . . . ?
C9 N10 N11 C10 0.0(2) . . . . ?
C9 N10 N11 C11 179.02(18) . . . . ?
N3 N2 C1 N1 -0.4(3) . . . . ?
C2 N1 C1 N2 0.1(3) . . . . ?
C1 N1 C2 N3 0.2(2) . . . . ?
N2 N3 C2 N1 -0.4(3) . . . . ?
C3 N3 C2 N1 178.40(19) . . . . ?
C2 N3 C3 C8 80.7(3) . . . . ?
N2 N3 C3 C8 -100.6(2) . . . . ?
C2 N3 C3 C4 -95.5(3) . . . . ?
N2 N3 C3 C4 83.1(3) . . . . ?
C8 C3 C4 N4 -173.6(2) . . . . ?
N3 C3 C4 N4 2.4(3) . . . . ?
C8 C3 C4 C5 6.3(3) . . . . ?
N3 C3 C4 C5 -177.70(19) . . . . ?
O1 N5 C5 C6 178.7(2) . . . . ?
O2 N5 C5 C6 -2.2(4) . . . . ?
O1 N5 C5 C4 -2.6(3) . . . . ?
O2 N5 C5 C4 176.4(2) . . . . ?
N4 C4 C5 N5 -4.7(3) . . . . ?
C3 C4 C5 N5 175.4(2) . . . . ?
N4 C4 C5 C6 174.0(2) . . . . ?
C3 C4 C5 C6 -6.0(3) . . . . ?
N5 C5 C6 N6 0.3(4) . . . . ?
C4 C5 C6 N6 -178.3(2) . . . . ?
N5 C5 C6 C7 -179.9(2) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
O4 N7 C7 C8 -1.9(3) . . . . ?
O3 N7 C7 C8 177.6(2) . . . . ?
O4 N7 C7 C6 176.3(2) . . . . ?
O3 N7 C7 C6 -4.3(3) . . . . ?
N6 C6 C7 N7 4.6(4) . . . . ?
C5 C6 C7 N7 -175.2(2) . . . . ?
N6 C6 C7 C8 -177.3(2) . . . . ?
C5 C6 C7 C8 3.0(3) . . . . ?
C4 C3 C8 N8 177.6(2) . . . . ?
N3 C3 C8 N8 1.6(3) . . . . ?
C4 C3 C8 C7 -1.9(3) . . . . ?
N3 C3 C8 C7 -177.89(18) . . . . ?
N7 C7 C8 N8 -4.2(3) . . . . ?
C6 C7 C8 N8 177.6(2) . . . . ?
N7 C7 C8 C3 175.33(19) . . . . ?
C6 C7 C8 C3 -2.9(3) . . . . ?
N11 N10 C9 N9 0.1(2) . . . . ?
C10 N9 C9 N10 -0.2(3) . . . . ?
C9 N9 C10 N11 0.2(2) . . . . ?
N10 N11 C10 N9 -0.2(2) . . . . ?
C11 N11 C10 N9 -179.06(19) . . . . ?
C10 N11 C11 C16 -92.1(3) . . . . ?
N10 N11 C11 C16 89.1(2) . . . . ?
C10 N11 C11 C12 90.2(3) . . . . ?
N10 N11 C11 C12 -88.5(2) . . . . ?
C16 C11 C12 N12 -179.9(2) . . . . ?
N11 C11 C12 N12 -2.4(3) . . . . ?
C16 C11 C12 C13 -1.2(3) . . . . ?
N11 C11 C12 C13 176.33(18) . . . . ?
O5 N13 C13 C14 168.6(2) . . . . ?
O6 N13 C13 C14 -10.9(3) . . . . ?
O5 N13 C13 C12 -9.1(3) . . . . ?
O6 N13 C13 C12 171.5(2) . . . . ?
N12 C12 C13 N13 3.2(3) . . . . ?
C11 C12 C13 N13 -175.42(18) . . . . ?
N12 C12 C13 C14 -174.4(2) . . . . ?
C11 C12 C13 C14 6.9(3) . . . . ?
N13 C13 C14 N14 -1.5(3) . . . . ?
C12 C13 C14 N14 176.1(2) . . . . ?
N13 C13 C14 C15 178.09(19) . . . . ?
C12 C13 C14 C15 -4.3(3) . . . . ?
O8 N15 C15 C14 173.7(2) . . . . ?
O7 N15 C15 C14 -8.0(3) . . . . ?
O8 N15 C15 C16 -5.4(3) . . . . ?
O7 N15 C15 C16 172.9(2) . . . . ?
N14 C14 C15 N15 -3.5(3) . . . . ?
C13 C14 C15 N15 176.9(2) . . . . ?
N14 C14 C15 C16 175.5(2) . . . . ?
C13 C14 C15 C16 -4.0(3) . . . . ?
C12 C11 C16 N16 173.9(2) . . . . ?
N11 C11 C16 N16 -3.5(3) . . . . ?
C12 C11 C16 C15 -6.9(3) . . . . ?
N11 C11 C16 C15 175.63(18) . . . . ?
N15 C15 C16 N16 7.7(3) . . . . ?
C14 C15 C16 N16 -171.4(2) . . . . ?
N15 C15 C16 C11 -171.5(2) . . . . ?
C14 C15 C16 C11 9.4(3) . . . . ?

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
C10 H10 O8 0.93 2.57 3.187(3) 124.1 1_455
C9 H9 O1 0.93 2.50 3.293(3) 143.5 2
C2 H2A O4 0.93 2.60 3.308(3) 133.0 1_455
C2 H2A O3 0.93 2.56 3.350(3) 142.4 1_455
C2 H2A N7 0.93 2.59 3.270(3) 130.2 1_455
N16 H16B O8 0.86 1.91 2.539(2) 129.0 .
N16 H16A N9 0.86 2.17 2.949(2) 150.5 2
N14 H14B O7 0.86 1.85 2.501(3) 131.2 .
N14 H14A O6 0.86 1.86 2.510(3) 131.2 .
N14 H14A N1 0.86 2.56 3.273(3) 141.0 2_566
N12 H12B O5 0.86 1.90 2.538(2) 130.0 .
N12 H12A O3 0.86 2.21 3.016(2) 155.9 1_445
N8 H8B O4 0.86 1.89 2.527(2) 129.5 .
N8 H8A O6 0.86 2.13 2.924(2) 153.0 2_566
N6 H6B O3 0.86 1.85 2.507(2) 132.3 .
N6 H6A O2 0.86 2.50 3.172(3) 135.9 2_665
N6 H6A O2 0.86 1.86 2.518(3) 132.3 .
N4 H4B O1 0.86 1.90 2.534(2) 129.1 .
N4 H4A O7 0.86 2.12 2.909(3) 151.8 1_455

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

