# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 940627'
_audit_update_record             
;
2017-05-18 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          330
_chemical_formula_moiety         CHNO
_chemical_formula_sum            'C18 H24 N6 O4'
_chemical_formula_weight         388.43

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                   5.1034(11)
_cell_length_b                   18.336(5)
_cell_length_c                   20.348(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.30(2)
_cell_angle_gamma                90
_cell_volume                     1896.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2461
_cell_measurement_theta_min      3.0100
_cell_measurement_theta_max      29.1040

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62276
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13332
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.214
_diffrn_reflns_theta_max         29.168
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4437
_reflns_number_gt                2338
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1173P)²+0.0933P] 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         4437
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1428
_refine_ls_R_factor_gt           0.0816
_refine_ls_wR_factor_ref         0.2596
_refine_ls_wR_factor_gt          0.2077
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
O4 O 0.2267(4) -0.02854(11) 0.57264(10) 0.0456(6) Uani 1 1 d . . . . .
O3 O 0.2540(4) 0.48359(12) 0.57339(11) 0.0490(6) Uani 1 1 d . . . . .
O2 O -0.3177(5) 0.34967(12) 0.69956(13) 0.0632(7) Uani 1 1 d . . . . .
H1 H -0.268884 0.313969 0.679695 0.095 Uiso 1 1 calc R U . . .
N1 N -0.2239(5) 0.21881(14) 0.66703(12) 0.0431(6) Uani 1 1 d . . . . .
C12 C 0.4591(6) 0.25161(14) 0.50002(14) 0.0366(7) Uani 1 1 d . . . . .
O1 O -0.5695(5) 0.37130(14) 0.77841(12) 0.0619(7) Uani 1 1 d . . . . .
N5 N 0.0701(6) 0.45637(15) 0.66657(14) 0.0564(8) Uani 1 1 d . . . . .
H20 H 0.220826 0.449381 0.688204 0.068 Uiso 1 1 calc R U . . .
H19 H -0.071697 0.451085 0.685876 0.068 Uiso 1 1 calc R U . . .
N2 N 0.6212(5) 0.27414(13) 0.45602(14) 0.0458(7) Uani 1 1 d . . . . .
N3 N 0.0259(5) -0.06700(16) 0.66052(13) 0.0557(8) Uani 1 1 d . . . . .
H24 H 0.171088 -0.082549 0.680459 0.067 Uiso 1 1 calc R U . . .
H23 H -0.118529 -0.071371 0.678872 0.067 Uiso 1 1 calc R U . . .
C6 C -0.5303(6) 0.24763(18) 0.74564(14) 0.0406(7) Uani 1 1 d . . . . .
N6 N -0.1850(5) 0.48692(16) 0.57245(14) 0.0568(8) Uani 1 1 d . . . . .
H17 H -0.202453 0.500144 0.531736 0.068 Uiso 1 1 calc R U . . .
H18 H -0.321873 0.481060 0.593574 0.068 Uiso 1 1 calc R U . . .
N4 N -0.2104(5) -0.01147(14) 0.57260(13) 0.0468(7) Uani 1 1 d . . . . .
H21 H -0.218506 0.009437 0.534637 0.056 Uiso 1 1 calc R U . . .
H22 H -0.350791 -0.016775 0.592478 0.056 Uiso 1 1 calc R U . . .
C17 C 0.0246(6) -0.03617(14) 0.60124(15) 0.0372(7) Uani 1 1 d . . . . .
C10 C 0.2405(6) 0.15452(15) 0.55310(15) 0.0420(7) Uani 1 1 d . . . . .
H7 H 0.215434 0.104835 0.559259 0.050 Uiso 1 1 calc R U . . .
C9 C 0.0974(6) 0.20432(16) 0.58823(15) 0.0393(7) Uani 1 1 d . . . . .
C14 C 0.1515(6) 0.27991(16) 0.57926(16) 0.0448(8) Uani 1 1 d . . . . .
H10 H 0.064714 0.314375 0.602849 0.054 Uiso 1 1 calc R U . . .
C8 C -0.0821(6) 0.17861(17) 0.63073(15) 0.0429(8) Uani 1 1 d . . . . .
H6 H -0.102565 0.128335 0.633435 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4140(6) 0.17654(16) 0.51048(15) 0.0423(7) Uani 1 1 d . . . . .
H8 H 0.504250 0.141928 0.487904 0.051 Uiso 1 1 calc R U . . .
C1 C -0.4052(6) 0.19497(17) 0.71073(15) 0.0441(8) Uani 1 1 d . . . . .
C13 C 0.3234(7) 0.30243(16) 0.53787(17) 0.0461(8) Uani 1 1 d . . . . .
H9 H 0.355235 0.352068 0.533639 0.055 Uiso 1 1 calc R U . . .
C7 C -0.4723(6) 0.32948(18) 0.74127(15) 0.0419(7) Uani 1 1 d . . . . .
C18 C 0.0561(6) 0.47540(15) 0.60307(15) 0.0381(7) Uani 1 1 d . . . . .
C2 C -0.4627(7) 0.1201(2) 0.71882(18) 0.0602(10) Uani 1 1 d . . . . .
H5 H -0.376819 0.084686 0.696148 0.072 Uiso 1 1 calc R U . . .
C15 C 0.7645(7) 0.22219(18) 0.41786(16) 0.0516(9) Uani 1 1 d . . . . .
H13 H 0.870039 0.248384 0.389093 0.077 Uiso 1 1 calc R U . . .
H11 H 0.876079 0.192409 0.447448 0.077 Uiso 1 1 calc R U . . .
H12 H 0.641230 0.191774 0.392056 0.077 Uiso 1 1 calc R U . . .
C16 C 0.6744(7) 0.35148(17) 0.44459(18) 0.0595(10) Uani 1 1 d . . . . .
H15 H 0.795088 0.355874 0.411299 0.089 Uiso 1 1 calc R U . . .
H14 H 0.512920 0.375908 0.430143 0.089 Uiso 1 1 calc R U . . .
H16 H 0.750113 0.373295 0.484842 0.089 Uiso 1 1 calc R U . . .
C4 C -0.7733(8) 0.1528(2) 0.79514(19) 0.0689(11) Uani 1 1 d . . . . .
H3 H -0.897964 0.138857 0.823287 0.083 Uiso 1 1 calc R U . . .
C3 C -0.6464(8) 0.1007(2) 0.76045(18) 0.0677(11) Uani 1 1 d . . . . .
H4 H -0.686595 0.051714 0.765528 0.081 Uiso 1 1 calc R U . . .
C5 C -0.7134(7) 0.2255(2) 0.78762(17) 0.0553(9) Uani 1 1 d . . . . .
H2 H -0.797850 0.260350 0.811269 0.066 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
O4 C17 1.238(3) . ?
O3 C18 1.233(3) . ?
O2 C7 1.266(4) . ?
O2 H1 0.8200 . ?
N1 C8 1.308(4) . ?
N1 C1 1.411(4) . ?
C12 N2 1.339(4) . ?
C12 C11 1.415(4) . ?
C12 C13 1.428(4) . ?
O1 C7 1.214(4) . ?
N5 C18 1.334(4) . ?
N5 H20 0.8600 . ?
N5 H19 0.8600 . ?
N2 C15 1.466(4) . ?
N2 C16 1.467(4) . ?
N3 C17 1.332(4) . ?
N3 H24 0.8600 . ?
N3 H23 0.8600 . ?
C6 C5 1.384(4) . ?
C6 C1 1.388(4) . ?
C6 C7 1.534(5) . ?
N6 C18 1.344(4) . ?
N6 H17 0.8600 . ?
N6 H18 0.8600 . ?
N4 C17 1.362(4) . ?
N4 H21 0.8600 . ?
N4 H22 0.8600 . ?
C10 C11 1.357(4) . ?
C10 C9 1.405(4) . ?
C10 H7 0.9300 . ?
C9 C8 1.398(4) . ?
C9 C14 1.428(4) . ?
C14 C13 1.337(4) . ?
C14 H10 0.9300 . ?
C8 H6 0.9300 . ?
C11 H8 0.9300 . ?
C1 C2 1.416(5) . ?
C13 H9 0.9300 . ?
C2 C3 1.367(5) . ?
C2 H5 0.9300 . ?
C15 H13 0.9600 . ?
C15 H11 0.9600 . ?
C15 H12 0.9600 . ?
C16 H15 0.9600 . ?
C16 H14 0.9600 . ?
C16 H16 0.9600 . ?
C4 C5 1.379(5) . ?
C4 C3 1.383(5) . ?
C4 H3 0.9300 . ?
C3 H4 0.9300 . ?
C5 H2 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 O2 H1 109.5 . . ?
C8 N1 C1 127.6(3) . . ?
N2 C12 C11 121.3(3) . . ?
N2 C12 C13 121.3(3) . . ?
C11 C12 C13 117.4(3) . . ?
C18 N5 H20 120.0 . . ?
C18 N5 H19 120.0 . . ?
H20 N5 H19 120.0 . . ?
C12 N2 C15 121.5(3) . . ?
C12 N2 C16 122.6(3) . . ?
C15 N2 C16 115.8(3) . . ?
C17 N3 H24 120.0 . . ?
C17 N3 H23 120.0 . . ?
H24 N3 H23 120.0 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 C7 117.9(3) . . ?
C1 C6 C7 123.4(3) . . ?
C18 N6 H17 120.0 . . ?
C18 N6 H18 120.0 . . ?
H17 N6 H18 120.0 . . ?
C17 N4 H21 120.0 . . ?
C17 N4 H22 120.0 . . ?
H21 N4 H22 120.0 . . ?
O4 C17 N3 122.6(3) . . ?
O4 C17 N4 120.0(3) . . ?
N3 C17 N4 117.4(3) . . ?
C11 C10 C9 122.2(3) . . ?
C11 C10 H7 118.9 . . ?
C9 C10 H7 118.9 . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 C14 123.5(3) . . ?
C10 C9 C14 116.7(3) . . ?
C13 C14 C9 121.7(3) . . ?
C13 C14 H10 119.1 . . ?
C9 C14 H10 119.1 . . ?
N1 C8 C9 126.0(3) . . ?
N1 C8 H6 117.0 . . ?
C9 C8 H6 117.0 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H8 119.7 . . ?
C12 C11 H8 119.7 . . ?
C6 C1 N1 117.8(3) . . ?
C6 C1 C2 120.3(3) . . ?
N1 C1 C2 121.9(3) . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H9 119.4 . . ?
C12 C13 H9 119.4 . . ?
O1 C7 O2 123.2(3) . . ?
O1 C7 C6 119.3(3) . . ?
O2 C7 C6 117.4(3) . . ?
O3 C18 N5 122.3(3) . . ?
O3 C18 N6 120.7(3) . . ?
N5 C18 N6 117.1(3) . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H5 120.5 . . ?
C1 C2 H5 120.5 . . ?
N2 C15 H13 109.5 . . ?
N2 C15 H11 109.5 . . ?
H13 C15 H11 109.5 . . ?
N2 C15 H12 109.5 . . ?
H13 C15 H12 109.5 . . ?
H11 C15 H12 109.5 . . ?
N2 C16 H15 109.5 . . ?
N2 C16 H14 109.5 . . ?
H15 C16 H14 109.5 . . ?
N2 C16 H16 109.5 . . ?
H15 C16 H16 109.5 . . ?
H14 C16 H16 109.5 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H3 120.3 . . ?
C3 C4 H3 120.3 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H4 119.4 . . ?
C4 C3 H4 119.4 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H2 119.3 . . ?
C6 C5 H2 119.3 . . ?

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
C11 C12 N2 C15 -1.6(4) . . . . ?
C13 C12 N2 C15 178.9(3) . . . . ?
C11 C12 N2 C16 -179.3(3) . . . . ?
C13 C12 N2 C16 1.2(4) . . . . ?
C11 C10 C9 C8 179.0(3) . . . . ?
C11 C10 C9 C14 -2.7(4) . . . . ?
C8 C9 C14 C13 -179.6(3) . . . . ?
C10 C9 C14 C13 2.1(4) . . . . ?
C1 N1 C8 C9 -179.5(3) . . . . ?
C10 C9 C8 N1 178.8(3) . . . . ?
C14 C9 C8 N1 0.5(5) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
N2 C12 C11 C10 -177.1(3) . . . . ?
C13 C12 C11 C10 2.4(4) . . . . ?
C5 C6 C1 N1 178.5(3) . . . . ?
C7 C6 C1 N1 -2.8(4) . . . . ?
C5 C6 C1 C2 -0.8(4) . . . . ?
C7 C6 C1 C2 178.0(3) . . . . ?
C8 N1 C1 C6 178.5(3) . . . . ?
C8 N1 C1 C2 -2.2(5) . . . . ?
C9 C14 C13 C12 0.7(5) . . . . ?
N2 C12 C13 C14 176.5(3) . . . . ?
C11 C12 C13 C14 -3.0(4) . . . . ?
C5 C6 C7 O1 6.4(4) . . . . ?
C1 C6 C7 O1 -172.4(3) . . . . ?
C5 C6 C7 O2 -175.5(3) . . . . ?
C1 C6 C7 O2 5.8(4) . . . . ?
C6 C1 C2 C3 1.2(5) . . . . ?
N1 C1 C2 C3 -178.0(3) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C5 C4 C3 C2 0.0(6) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C1 C6 C5 C4 -0.1(5) . . . . ?
C7 C6 C5 C4 -178.9(3) . . . . ?

_refine_diff_density_max         0.618
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.083

