# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo_nwsynhklf4
_database_code_depnum_ccdc_archive 'CCDC 1561373'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 N8 O5'
_chemical_formula_weight         416.41

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                   14.3939(17)
_cell_length_b                   9.0882(11)
_cell_length_c                   14.4576(17)
_cell_angle_alpha                90
_cell_angle_beta                 107.205(4)
_cell_angle_gamma                90
_cell_volume                     1806.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6579
_cell_measurement_theta_min      2.689
_cell_measurement_theta_max      25.83

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6493
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   Twinabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  triumph
_diffrn_measurement_device_type  'APEX II '
_diffrn_measurement_method       omega/phi-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18107
_diffrn_reflns_av_unetI/netI     0.1207
_diffrn_reflns_av_R_equivalents  0.1070
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.481
_diffrn_reflns_theta_max         27.090
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3979
_reflns_number_gt                2963
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'COSMO v1.61'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ', Twin'

_vrf_PLAT030_mo_nwsynhklf4       
;
PROBLEM: _diffrn_reflns_number   <   _reflns_number_total 
RESPONSE: Refinement with hklf4 format for twinning
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+1.5526P] 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         3979
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.81995(13) 0.1511(2) 0.90315(13) 0.0101(4) Uani 1 1 d . . . . .
C2 C 0.72069(13) 0.2210(2) 0.84787(14) 0.0121(4) Uani 1 1 d . . . . .
H2A H 0.7200 0.3302 0.8558 0.015 Uiso 1 1 calc R U . . .
C3 C 0.67296(13) 0.1381(2) 0.91641(14) 0.0120(4) Uani 1 1 d . . . . .
H3A H 0.6683 0.2052 0.9697 0.014 Uiso 1 1 calc R U . . .
C4 C 0.76399(13) 0.0398(2) 0.95207(14) 0.0114(4) Uani 1 1 d . . . . .
C5 C 0.75080(14) -0.1119(2) 0.90515(14) 0.0125(4) Uani 1 1 d . . . . .
C6 C 0.57274(14) -0.0743(2) 0.84617(14) 0.0134(4) Uani 1 1 d . . . . .
C7 C 0.87902(13) 0.0832(2) 0.84240(14) 0.0110(4) Uani 1 1 d . . . . .
C8 C 0.74409(14) 0.1339(2) 0.69392(14) 0.0131(4) Uani 1 1 d . . . . .
C9 C 0.88571(14) 0.2608(2) 0.97416(14) 0.0124(4) Uani 1 1 d . . . . .
H9A H 0.8475 0.3119 1.0112 0.015 Uiso 1 1 calc R U . . .
H9B H 0.9392 0.2068 1.0207 0.015 Uiso 1 1 calc R U . . .
C10 C 1.01775(14) 0.3650(2) 0.91375(14) 0.0155(4) Uani 1 1 d . . . . .
H10 H 1.0649 0.2935 0.9445 0.019 Uiso 1 1 calc R U . . .
C11 C 0.94732(15) 0.5482(2) 0.82939(15) 0.0191(5) Uani 1 1 d . . . . .
H11 H 0.9360 0.6319 0.7882 0.023 Uiso 1 1 calc R U . . .
C12 C 0.88090(15) 0.4884(2) 0.86763(15) 0.0174(4) Uani 1 1 d . . . . .
H12 H 0.8163 0.5215 0.8590 0.021 Uiso 1 1 calc R U . . .
C13 C 0.80570(14) 0.0161(2) 1.06204(14) 0.0129(4) Uani 1 1 d . . . . .
H13A H 0.8711 -0.0288 1.0768 0.015 Uiso 1 1 calc R U . . .
H13B H 0.8122 0.1121 1.0957 0.015 Uiso 1 1 calc R U . . .
C14 C 0.65466(14) -0.0418(2) 1.10799(15) 0.0166(4) Uani 1 1 d . . . . .
H14 H 0.6298 0.0557 1.1006 0.020 Uiso 1 1 calc R U . . .
C15 C 0.66937(15) -0.2733(2) 1.13409(15) 0.0191(5) Uani 1 1 d . . . . .
H15 H 0.6559 -0.3715 1.1488 0.023 Uiso 1 1 calc R U . . .
C16 C 0.75123(15) -0.2298(2) 1.11368(16) 0.0188(5) Uani 1 1 d . . . . .
H16 H 0.8045 -0.2900 1.1115 0.023 Uiso 1 1 calc R U . . .
C17 C 0.56383(17) 0.5144(3) 0.90602(16) 0.0260(5) Uani 1 1 d . . . . .
H17A H 0.6067 0.5127 0.9728 0.039 Uiso 1 1 calc R U . . .
H17B H 0.5311 0.4190 0.8904 0.039 Uiso 1 1 calc R U . . .
H17C H 0.5151 0.5921 0.8992 0.039 Uiso 1 1 calc R U . . .
N1 N 0.65732(12) -0.15588(19) 0.85949(12) 0.0138(4) Uani 1 1 d . . . . .
H1 H 0.6501 -0.2459 0.8360 0.017 Uiso 1 1 calc R U . . .
N2 N 0.58145(11) 0.06524(18) 0.87515(12) 0.0127(4) Uani 1 1 d . . . . .
H2 H 0.5279 0.1161 0.8687 0.015 Uiso 1 1 calc R U . . .
N3 N 0.83619(12) 0.08353(19) 0.74384(11) 0.0127(4) Uani 1 1 d . . . . .
H3 H 0.8712 0.0477 0.7084 0.015 Uiso 1 1 calc R U . . .
N4 N 0.68588(12) 0.1755(2) 0.74776(12) 0.0146(4) Uani 1 1 d . . . . .
H4 H 0.6322(16) 0.209(2) 0.7174(15) 0.009(5) Uiso 1 1 d . . . . .
N5 N 0.92648(11) 0.36946(18) 0.92180(11) 0.0121(4) Uani 1 1 d . . . . .
N6 N 1.03365(12) 0.4714(2) 0.85812(12) 0.0174(4) Uani 1 1 d . . . . .
N7 N 0.74143(12) -0.08040(19) 1.09666(11) 0.0131(4) Uani 1 1 d . . . . .
N8 N 0.60873(13) -0.1554(2) 1.13054(13) 0.0193(4) Uani 1 1 d . . . . .
O1 O 0.81903(10) -0.19410(16) 0.91177(10) 0.0170(3) Uani 1 1 d . . . . .
O2 O 0.49270(10) -0.13466(16) 0.80834(10) 0.0171(3) Uani 1 1 d . . . . .
O3 O 0.96040(10) 0.03613(16) 0.87834(10) 0.0158(3) Uani 1 1 d . . . . .
O4 O 0.71714(10) 0.13422(17) 0.60503(10) 0.0186(3) Uani 1 1 d . . . . .
O5 O 0.62030(11) 0.54256(17) 0.84119(12) 0.0206(3) Uani 1 1 d . . . . .
H5 H 0.586(2) 0.505(4) 0.784(2) 0.059(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
C1 C7 1.522(3) . ?
C1 C9 1.539(3) . ?
C1 C2 1.552(3) . ?
C1 C4 1.584(3) . ?
C2 N4 1.445(3) . ?
C2 C3 1.557(3) . ?
C2 H2A 1.0000 . ?
C3 N2 1.437(2) . ?
C3 C4 1.543(3) . ?
C3 H3A 1.0000 . ?
C4 C5 1.524(3) . ?
C4 C13 1.539(3) . ?
C5 O1 1.215(2) . ?
C5 N1 1.371(3) . ?
C6 O2 1.247(2) . ?
C6 N2 1.330(3) . ?
C6 N1 1.389(3) . ?
C7 O3 1.210(2) . ?
C7 N3 1.375(2) . ?
C8 O4 1.228(2) . ?
C8 N4 1.355(3) . ?
C8 N3 1.386(3) . ?
C9 N5 1.468(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N6 1.321(3) . ?
C10 N5 1.353(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.352(3) . ?
C11 N6 1.378(3) . ?
C11 H11 0.9500 . ?
C12 N5 1.382(3) . ?
C12 H12 0.9500 . ?
C13 N7 1.466(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N8 1.318(3) . ?
C14 N7 1.353(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.356(3) . ?
C15 N8 1.374(3) . ?
C15 H15 0.9500 . ?
C16 N7 1.380(3) . ?
C16 H16 0.9500 . ?
C17 O5 1.434(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?
N3 H3 0.8800 . ?
N4 H4 0.82(2) . ?
O5 H5 0.89(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
C7 C1 C9 108.02(15) . . ?
C7 C1 C2 117.07(15) . . ?
C9 C1 C2 111.70(16) . . ?
C7 C1 C4 116.30(16) . . ?
C9 C1 C4 114.16(15) . . ?
C2 C1 C4 88.78(14) . . ?
N4 C2 C1 113.13(16) . . ?
N4 C2 C3 114.33(16) . . ?
C1 C2 C3 89.25(14) . . ?
N4 C2 H2A 112.7 . . ?
C1 C2 H2A 112.7 . . ?
C3 C2 H2A 112.7 . . ?
N2 C3 C4 117.08(16) . . ?
N2 C3 C2 118.79(16) . . ?
C4 C3 C2 90.09(14) . . ?
N2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C5 C4 C13 106.98(16) . . ?
C5 C4 C3 113.18(16) . . ?
C13 C4 C3 117.35(15) . . ?
C5 C4 C1 113.08(15) . . ?
C13 C4 C1 117.14(15) . . ?
C3 C4 C1 88.56(14) . . ?
O1 C5 N1 120.95(18) . . ?
O1 C5 C4 121.99(18) . . ?
N1 C5 C4 116.95(17) . . ?
O2 C6 N2 123.13(18) . . ?
O2 C6 N1 118.96(18) . . ?
N2 C6 N1 117.91(18) . . ?
O3 C7 N3 121.75(17) . . ?
O3 C7 C1 122.03(17) . . ?
N3 C7 C1 116.17(16) . . ?
O4 C8 N4 122.89(19) . . ?
O4 C8 N3 120.21(18) . . ?
N4 C8 N3 116.85(17) . . ?
N5 C9 C1 110.64(15) . . ?
N5 C9 H9A 109.5 . . ?
C1 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
C1 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N6 C10 N5 112.18(19) . . ?
N6 C10 H10 123.9 . . ?
N5 C10 H10 123.9 . . ?
C12 C11 N6 110.95(19) . . ?
C12 C11 H11 124.5 . . ?
N6 C11 H11 124.5 . . ?
C11 C12 N5 105.75(18) . . ?
C11 C12 H12 127.1 . . ?
N5 C12 H12 127.1 . . ?
N7 C13 C4 110.10(15) . . ?
N7 C13 H13A 109.6 . . ?
C4 C13 H13A 109.6 . . ?
N7 C13 H13B 109.6 . . ?
C4 C13 H13B 109.6 . . ?
H13A C13 H13B 108.2 . . ?
N8 C14 N7 112.07(19) . . ?
N8 C14 H14 124.0 . . ?
N7 C14 H14 124.0 . . ?
C16 C15 N8 110.36(19) . . ?
C16 C15 H15 124.8 . . ?
N8 C15 H15 124.8 . . ?
C15 C16 N7 106.04(18) . . ?
C15 C16 H16 127.0 . . ?
N7 C16 H16 127.0 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 N1 C6 127.32(18) . . ?
C5 N1 H1 116.3 . . ?
C6 N1 H1 116.3 . . ?
C6 N2 C3 124.05(17) . . ?
C6 N2 H2 118.0 . . ?
C3 N2 H2 118.0 . . ?
C7 N3 C8 127.37(17) . . ?
C7 N3 H3 116.3 . . ?
C8 N3 H3 116.3 . . ?
C8 N4 C2 124.40(17) . . ?
C8 N4 H4 115.9(14) . . ?
C2 N4 H4 115.0(15) . . ?
C10 N5 C12 106.57(17) . . ?
C10 N5 C9 124.76(17) . . ?
C12 N5 C9 128.58(16) . . ?
C10 N6 C11 104.55(17) . . ?
C14 N7 C16 106.42(17) . . ?
C14 N7 C13 125.78(17) . . ?
C16 N7 C13 127.45(17) . . ?
C14 N8 C15 105.10(17) . . ?
C17 O5 H5 106(2) . . ?

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 C1 C2 N4 16.5(2) . . . . ?
C9 C1 C2 N4 141.73(16) . . . . ?
C4 C1 C2 N4 -102.67(17) . . . . ?
C7 C1 C2 C3 132.72(17) . . . . ?
C9 C1 C2 C3 -102.01(16) . . . . ?
C4 C1 C2 C3 13.59(14) . . . . ?
N4 C2 C3 N2 -20.1(2) . . . . ?
C1 C2 C3 N2 -135.30(18) . . . . ?
N4 C2 C3 C4 101.21(18) . . . . ?
C1 C2 C3 C4 -13.95(14) . . . . ?
N2 C3 C4 C5 21.9(2) . . . . ?
C2 C3 C4 C5 -100.91(17) . . . . ?
N2 C3 C4 C13 -103.5(2) . . . . ?
C2 C3 C4 C13 133.71(17) . . . . ?
N2 C3 C4 C1 136.46(17) . . . . ?
C2 C3 C4 C1 13.66(14) . . . . ?
C7 C1 C4 C5 -18.9(2) . . . . ?
C9 C1 C4 C5 -145.73(17) . . . . ?
C2 C1 C4 C5 100.95(17) . . . . ?
C7 C1 C4 C13 106.24(19) . . . . ?
C9 C1 C4 C13 -20.6(2) . . . . ?
C2 C1 C4 C13 -133.94(17) . . . . ?
C7 C1 C4 C3 -133.53(17) . . . . ?
C9 C1 C4 C3 99.61(17) . . . . ?
C2 C1 C4 C3 -13.71(14) . . . . ?
C13 C4 C5 O1 -61.9(2) . . . . ?
C3 C4 C5 O1 167.27(17) . . . . ?
C1 C4 C5 O1 68.5(2) . . . . ?
C13 C4 C5 N1 114.34(18) . . . . ?
C3 C4 C5 N1 -16.4(2) . . . . ?
C1 C4 C5 N1 -115.23(18) . . . . ?
C9 C1 C7 O3 47.2(2) . . . . ?
C2 C1 C7 O3 174.26(18) . . . . ?
C4 C1 C7 O3 -82.7(2) . . . . ?
C9 C1 C7 N3 -130.31(18) . . . . ?
C2 C1 C7 N3 -3.2(3) . . . . ?
C4 C1 C7 N3 99.8(2) . . . . ?
C7 C1 C9 N5 55.0(2) . . . . ?
C2 C1 C9 N5 -75.11(19) . . . . ?
C4 C1 C9 N5 -173.94(15) . . . . ?
N6 C11 C12 N5 -0.4(2) . . . . ?
C5 C4 C13 N7 -56.33(19) . . . . ?
C3 C4 C13 N7 72.1(2) . . . . ?
C1 C4 C13 N7 175.57(16) . . . . ?
N8 C15 C16 N7 -0.1(3) . . . . ?
O1 C5 N1 C6 -179.74(18) . . . . ?
C4 C5 N1 C6 3.9(3) . . . . ?
O2 C6 N1 C5 -175.37(18) . . . . ?
N2 C6 N1 C5 4.3(3) . . . . ?
O2 C6 N2 C3 -178.19(18) . . . . ?
N1 C6 N2 C3 2.1(3) . . . . ?
C4 C3 N2 C6 -15.7(3) . . . . ?
C2 C3 N2 C6 90.7(2) . . . . ?
O3 C7 N3 C8 179.98(19) . . . . ?
C1 C7 N3 C8 -2.5(3) . . . . ?
O4 C8 N3 C7 176.27(19) . . . . ?
N4 C8 N3 C7 -6.4(3) . . . . ?
O4 C8 N4 C2 -159.69(19) . . . . ?
N3 C8 N4 C2 23.1(3) . . . . ?
C1 C2 N4 C8 -27.7(3) . . . . ?
C3 C2 N4 C8 -127.9(2) . . . . ?
N6 C10 N5 C12 -0.4(2) . . . . ?
N6 C10 N5 C9 176.35(17) . . . . ?
C11 C12 N5 C10 0.5(2) . . . . ?
C11 C12 N5 C9 -176.10(19) . . . . ?
C1 C9 N5 C10 -100.7(2) . . . . ?
C1 C9 N5 C12 75.3(2) . . . . ?
N5 C10 N6 C11 0.1(2) . . . . ?
C12 C11 N6 C10 0.2(2) . . . . ?
N8 C14 N7 C16 -0.2(2) . . . . ?
N8 C14 N7 C13 173.38(18) . . . . ?
C15 C16 N7 C14 0.2(2) . . . . ?
C15 C16 N7 C13 -173.25(18) . . . . ?
C4 C13 N7 C14 -74.5(2) . . . . ?
C4 C13 N7 C16 97.8(2) . . . . ?
N7 C14 N8 C15 0.1(2) . . . . ?
C16 C15 N8 C14 0.0(2) . . . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_mo_nwls8_0m
_database_code_depnum_ccdc_archive 'CCDC 1561372'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-08-07 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         ?
_chemical_formula_sum            'C16 H22 N8 O7'
_chemical_formula_weight         438.41

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                   7.9316(10)
_cell_length_b                   8.1627(10)
_cell_length_c                   16.285(2)
_cell_angle_alpha                81.196(5)
_cell_angle_beta                 78.977(6)
_cell_angle_gamma                74.965(5)
_cell_volume                     993.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2841
_cell_measurement_theta_min      2.563
_cell_measurement_theta_max      24.17

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_T_max  0.9990
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15153
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.282
_diffrn_reflns_theta_max         25.095
_diffrn_reflns_theta_full        25.095
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3523
_reflns_number_gt                2684
_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       'COSMO v1.61'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²+0.3861P] 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         3523
_refine_ls_number_parameters     322
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.6663(3) 0.0637(2) 0.25892(11) 0.0156(4) Uani 1 1 d . . . . .
H1A H 0.7690 -0.0374 0.2523 0.019 Uiso 1 1 calc R U . . .
C2 C 0.7067(3) 0.2152(2) 0.19553(12) 0.0154(4) Uani 1 1 d . . . . .
C3 C 0.7846(3) 0.2684(2) 0.26690(11) 0.0149(4) Uani 1 1 d . . . . .
H3 H 0.9138 0.2129 0.2620 0.018 Uiso 1 1 calc R U . . .
C4 C 0.6806(3) 0.1598(2) 0.33332(11) 0.0139(4) Uani 1 1 d . . . . .
C5 C 0.5060(3) 0.2658(2) 0.37287(11) 0.0146(4) Uani 1 1 d . . . . .
C6 C 0.6109(3) 0.5309(3) 0.32266(12) 0.0174(5) Uani 1 1 d . . . . .
C7 C 0.7750(3) 0.0467(2) 0.40258(12) 0.0159(5) Uani 1 1 d . . . . .
H7A H 0.6949 -0.0201 0.4382 0.019 Uiso 1 1 calc R U . . .
H7B H 0.8804 -0.0346 0.3767 0.019 Uiso 1 1 calc R U . . .
C8 C 0.9842(3) 0.2016(3) 0.43953(12) 0.0184(5) Uani 1 1 d . . . . .
H8 H 1.0779 0.1780 0.3938 0.022 Uiso 1 1 calc R U . . .
C9 C 0.9758(3) 0.2950(2) 0.50243(12) 0.0185(5) Uani 1 1 d . . . . .
H9 H 1.0651 0.3488 0.5081 0.022 Uiso 1 1 calc R U . . .
C10 C 0.7352(3) 0.2101(3) 0.52648(12) 0.0178(5) Uani 1 1 d . . . . .
H10 H 0.6226 0.1910 0.5515 0.021 Uiso 1 1 calc R U . . .
C11 C 0.5391(3) 0.3409(3) 0.17502(12) 0.0184(5) Uani 1 1 d . . . . .
C12 C 0.3622(3) 0.1289(2) 0.23521(11) 0.0151(4) Uani 1 1 d . . . . .
C13 C 0.8423(3) 0.1797(3) 0.11662(12) 0.0219(5) Uani 1 1 d . . . . .
H13A H 0.8673 0.2890 0.0882 0.026 Uiso 1 1 calc R U . . .
H13B H 0.9538 0.1066 0.1333 0.026 Uiso 1 1 calc R U . . .
C14 C 0.7020(3) 0.1759(3) -0.01033(13) 0.0315(6) Uani 1 1 d . . . . .
H14 H 0.6649 0.2951 -0.0260 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6834(3) 0.0474(4) -0.04931(14) 0.0380(7) Uani 1 1 d . . . . .
H15 H 0.6286 0.0629 -0.0979 0.046 Uiso 1 1 calc R U . . .
C16 C 0.8148(3) -0.0727(3) 0.05488(14) 0.0302(6) Uani 1 1 d . . . . .
H16 H 0.8715 -0.1564 0.0945 0.036 Uiso 1 1 calc R U . . .
N1 N 0.4861(2) 0.4395(2) 0.36215(10) 0.0173(4) Uani 1 1 d . . . . .
H1B H 0.3819 0.5006 0.3827 0.021 Uiso 1 1 calc R U . . .
N2 N 0.7574(2) 0.4430(2) 0.27926(10) 0.0176(4) Uani 1 1 d . . . . .
H2 H 0.8419 0.4956 0.2570 0.021 Uiso 1 1 calc R U . . .
N3 N 0.8296(2) 0.1472(2) 0.45503(9) 0.0149(4) Uani 1 1 d . . . . .
N4 N 0.8188(2) 0.3014(2) 0.55733(10) 0.0196(4) Uani 1 1 d . . . . .
N5 N 0.3832(2) 0.2913(2) 0.20291(10) 0.0173(4) Uani 1 1 d . . . . .
H5 H 0.2855 0.3716 0.2000 0.021 Uiso 1 1 calc R U . . .
N6 N 0.5077(2) 0.0150(2) 0.25494(10) 0.0163(4) Uani 1 1 d . . . . .
H6 H 0.5055 -0.0935 0.2658 0.020 Uiso 1 1 calc R U . . .
N7 N 0.7863(2) 0.0964(2) 0.05702(10) 0.0242(4) Uani 1 1 d . . . . .
N8 N 0.7552(3) -0.1088(3) -0.00840(12) 0.0363(5) Uani 1 1 d . . . . .
O1 O 0.39106(19) 0.20019(17) 0.41438(8) 0.0195(3) Uani 1 1 d . . . . .
O2 O 0.5823(2) 0.68373(17) 0.33013(9) 0.0228(4) Uani 1 1 d . . . . .
O3 O 0.5411(2) 0.47984(19) 0.13658(10) 0.0295(4) Uani 1 1 d . . . . .
O4 O 0.21619(19) 0.09709(17) 0.24258(8) 0.0195(3) Uani 1 1 d . . . . .
O10 O 0.1139(2) 0.7908(2) 0.26748(10) 0.0259(4) Uani 1 1 d . . . . .
H10A H 0.147(4) 0.744(3) 0.3172(18) 0.046(8) Uiso 1 1 d . . . . .
H10B H 0.162(4) 0.883(4) 0.2542(16) 0.045(8) Uiso 1 1 d . . . . .
O11 O 0.9372(2) 0.4520(2) -0.18409(12) 0.0265(4) Uani 1 1 d . . . . .
H11A H 0.909(4) 0.453(4) -0.131(2) 0.070(11) Uiso 1 1 d . . . . .
H11B H 0.909(4) 0.364(4) -0.2014(18) 0.054(9) Uiso 1 1 d . . . . .
O12 O 0.8840(18) 0.5225(9) -0.0307(3) 0.033(2) Uani 0.516(18) 1 d D . P A -1
H12A H 0.844(11) 0.639(4) -0.019(4) 0.06(2) Uiso 0.516(18) 1 d D . P A -1
H12B H 1.028(10) 0.486(7) -0.023(3) 0.040(17) Uiso 0.516(18) 1 d . . P A -1
O12A O 0.7773(17) 0.5706(9) -0.0172(3) 0.027(2) Uani 0.484(18) 1 d D . P A 2
H12C H 0.755(10) 0.693(3) -0.025(4) 0.06(2) Uiso 0.484(18) 1 d D . P A 2
H12D H 0.694(7) 0.551(6) 0.027(3) 0.029(15) Uiso 0.484(18) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N6 1.430(3) . ?
C1 C2 1.545(3) . ?
C1 C4 1.577(3) . ?
C1 H1A 1.0000 . ?
C2 C11 1.513(3) . ?
C2 C13 1.522(3) . ?
C2 C3 1.578(3) . ?
C3 N2 1.424(3) . ?
C3 C4 1.544(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.514(3) . ?
C4 C7 1.526(3) . ?
C5 O1 1.217(2) . ?
C5 N1 1.373(2) . ?
C6 O2 1.230(2) . ?
C6 N2 1.331(3) . ?
C6 N1 1.394(3) . ?
C7 N3 1.459(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.350(3) . ?
C8 N3 1.376(3) . ?
C8 H8 0.9500 . ?
C9 N4 1.381(3) . ?
C9 H9 0.9500 . ?
C10 N4 1.321(3) . ?
C10 N3 1.352(2) . ?
C10 H10 0.9500 . ?
C11 O3 1.211(2) . ?
C11 N5 1.374(3) . ?
C12 O4 1.231(2) . ?
C12 N6 1.339(3) . ?
C12 N5 1.389(2) . ?
C13 N7 1.458(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.358(4) . ?
C14 N7 1.382(3) . ?
C14 H14 0.9500 . ?
C15 N8 1.379(3) . ?
C15 H15 0.9500 . ?
C16 N8 1.313(3) . ?
C16 N7 1.345(3) . ?
C16 H16 0.9500 . ?
N1 H1B 0.8800 . ?
N2 H2 0.8800 . ?
N5 H5 0.8800 . ?
N6 H6 0.8800 . ?
O10 H10A 0.89(3) . ?
O10 H10B 0.91(3) . ?
O11 H11A 0.85(3) . ?
O11 H11B 0.91(3) . ?
O12 H12A 0.96(2) . ?
O12 H12B 1.13(8) . ?
O12A H12C 0.96(2) . ?
O12A H12D 0.91(6) . ?

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
N6 C1 C2 116.04(16) . . ?
N6 C1 C4 121.42(16) . . ?
C2 C1 C4 89.65(14) . . ?
N6 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C4 C1 H1A 109.4 . . ?
C11 C2 C13 111.41(16) . . ?
C11 C2 C1 111.66(17) . . ?
C13 C2 C1 119.16(17) . . ?
C11 C2 C3 112.76(16) . . ?
C13 C2 C3 112.79(17) . . ?
C1 C2 C3 86.97(14) . . ?
N2 C3 C4 116.79(16) . . ?
N2 C3 C2 121.27(16) . . ?
C4 C3 C2 89.64(14) . . ?
N2 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C5 C4 C7 109.15(15) . . ?
C5 C4 C3 111.94(15) . . ?
C7 C4 C3 118.30(17) . . ?
C5 C4 C1 114.16(16) . . ?
C7 C4 C1 114.95(16) . . ?
C3 C4 C1 87.06(14) . . ?
O1 C5 N1 121.63(18) . . ?
O1 C5 C4 121.68(17) . . ?
N1 C5 C4 116.65(17) . . ?
O2 C6 N2 124.07(19) . . ?
O2 C6 N1 119.57(18) . . ?
N2 C6 N1 116.36(17) . . ?
N3 C7 C4 111.68(15) . . ?
N3 C7 H7A 109.3 . . ?
C4 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
C4 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 N3 106.14(18) . . ?
C9 C8 H8 126.9 . . ?
N3 C8 H8 126.9 . . ?
C8 C9 N4 110.36(19) . . ?
C8 C9 H9 124.8 . . ?
N4 C9 H9 124.8 . . ?
N4 C10 N3 111.77(19) . . ?
N4 C10 H10 124.1 . . ?
N3 C10 H10 124.1 . . ?
O3 C11 N5 121.20(19) . . ?
O3 C11 C2 121.83(19) . . ?
N5 C11 C2 116.97(17) . . ?
O4 C12 N6 124.30(18) . . ?
O4 C12 N5 119.59(18) . . ?
N6 C12 N5 116.09(18) . . ?
N7 C13 C2 113.84(18) . . ?
N7 C13 H13A 108.8 . . ?
C2 C13 H13A 108.8 . . ?
N7 C13 H13B 108.8 . . ?
C2 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 N7 105.3(2) . . ?
C15 C14 H14 127.3 . . ?
N7 C14 H14 127.3 . . ?
C14 C15 N8 110.4(2) . . ?
C14 C15 H15 124.8 . . ?
N8 C15 H15 124.8 . . ?
N8 C16 N7 112.1(2) . . ?
N8 C16 H16 123.9 . . ?
N7 C16 H16 123.9 . . ?
C5 N1 C6 127.84(17) . . ?
C5 N1 H1B 116.1 . . ?
C6 N1 H1B 116.1 . . ?
C6 N2 C3 123.55(17) . . ?
C6 N2 H2 118.2 . . ?
C3 N2 H2 118.2 . . ?
C10 N3 C8 106.82(17) . . ?
C10 N3 C7 126.60(18) . . ?
C8 N3 C7 126.53(17) . . ?
C10 N4 C9 104.91(17) . . ?
C11 N5 C12 127.48(17) . . ?
C11 N5 H5 116.3 . . ?
C12 N5 H5 116.3 . . ?
C12 N6 C1 122.23(17) . . ?
C12 N6 H6 118.9 . . ?
C1 N6 H6 118.9 . . ?
C16 N7 C14 107.09(19) . . ?
C16 N7 C13 126.33(18) . . ?
C14 N7 C13 126.5(2) . . ?
C16 N8 C15 105.0(2) . . ?
H10A O10 H10B 104(2) . . ?
H11A O11 H11B 111(3) . . ?
H12A O12 H12B 105(6) . . ?
H12C O12A H12D 103(5) . . ?

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.056

