# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_m20150919c1
_database_code_depnum_ccdc_archive 'CCDC 1433224'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 N4 O5'
_chemical_formula_weight         376.41

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.454(5)
_cell_length_b                   21.985(9)
_cell_length_c                   8.731(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.524(11)
_cell_angle_gamma                90.00
_cell_volume                     1958.8(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4744
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19595
_diffrn_reflns_av_R_equivalents  0.1027
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3441
_reflns_number_gt                2652
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1107P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3441
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1558
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.05176(13) 0.70118(6) 0.62665(15) 0.0346(3) Uani 1 1 d . . .
O2 O 0.06919(12) 0.60080(6) 0.57563(14) 0.0322(3) Uani 1 1 d . . .
O3 O -0.01391(12) 0.65592(6) 0.23271(15) 0.0338(4) Uani 1 1 d . . .
O4 O 0.12012(13) 0.62151(6) 0.07936(15) 0.0393(4) Uani 1 1 d . . .
O5 O 0.32035(15) 0.52433(6) 0.3127(2) 0.0555(5) Uani 1 1 d . . .
N1 N 0.18247(15) 0.66957(7) 0.46845(17) 0.0292(4) Uani 1 1 d . . .
N2 N 0.19038(14) 0.62777(7) 0.34974(17) 0.0292(4) Uani 1 1 d . . .
N3 N 0.32000(15) 0.62652(7) 0.33064(18) 0.0307(4) Uani 1 1 d . . .
N4 N 0.37987(15) 0.68099(7) 0.31257(18) 0.0307(4) Uani 1 1 d . . .
C1 C 0.21167(18) 0.73157(8) 0.4299(2) 0.0305(4) Uani 1 1 d . . .
H1A H 0.2323 0.7566 0.5264 0.037 Uiso 1 1 calc R . .
H1B H 0.1350 0.7497 0.3575 0.037 Uiso 1 1 calc R . .
C2 C 0.32792(18) 0.72993(8) 0.3530(2) 0.0296(4) Uani 1 1 d . . .
C3 C 0.38832(18) 0.78821(8) 0.3204(2) 0.0304(4) Uani 1 1 d . . .
C4 C 0.3462(2) 0.84383(9) 0.3677(2) 0.0355(5) Uani 1 1 d . . .
H4 H 0.2803 0.8449 0.4274 0.043 Uiso 1 1 calc R . .
C5 C 0.3998(2) 0.89761(9) 0.3283(2) 0.0388(5) Uani 1 1 d . . .
H5 H 0.3701 0.9353 0.3608 0.047 Uiso 1 1 calc R . .
C6 C 0.49631(19) 0.89701(9) 0.2418(2) 0.0375(5) Uani 1 1 d . . .
H6 H 0.5328 0.9340 0.2147 0.045 Uiso 1 1 calc R . .
C7 C 0.53888(19) 0.84184(9) 0.1955(2) 0.0371(5) Uani 1 1 d . . .
H7 H 0.6055 0.8411 0.1368 0.044 Uiso 1 1 calc R . .
C8 C 0.48621(18) 0.78825(9) 0.2333(2) 0.0336(5) Uani 1 1 d . . .
H8 H 0.5164 0.7508 0.2001 0.040 Uiso 1 1 calc R . .
C9 C 0.3772(2) 0.57172(9) 0.3080(2) 0.0388(5) Uani 1 1 d . . .
C10 C 0.5137(2) 0.57664(10) 0.2789(3) 0.0474(6) Uani 1 1 d . . .
H10A H 0.5495 0.5358 0.2720 0.071 Uiso 1 1 calc R . .
H10B H 0.5695 0.5989 0.3656 0.071 Uiso 1 1 calc R . .
H10C H 0.5108 0.5985 0.1804 0.071 Uiso 1 1 calc R . .
C11 C 0.09732(18) 0.63530(8) 0.2036(2) 0.0299(4) Uani 1 1 d . . .
C12 C -0.12234(19) 0.66500(10) 0.0950(2) 0.0387(5) Uani 1 1 d . . .
H12 H -0.0872 0.6820 0.0061 0.046 Uiso 1 1 calc R . .
C13 C -0.1878(2) 0.60490(11) 0.0475(3) 0.0504(6) Uani 1 1 d . . .
H13A H -0.1247 0.5770 0.0168 0.076 Uiso 1 1 calc R . .
H13B H -0.2620 0.6110 -0.0414 0.076 Uiso 1 1 calc R . .
H13C H -0.2193 0.5876 0.1360 0.076 Uiso 1 1 calc R . .
C14 C -0.2111(2) 0.71109(11) 0.1471(3) 0.0502(6) Uani 1 1 d . . .
H14A H -0.2424 0.6950 0.2370 0.075 Uiso 1 1 calc R . .
H14B H -0.2860 0.7193 0.0607 0.075 Uiso 1 1 calc R . .
H14C H -0.1624 0.7489 0.1775 0.075 Uiso 1 1 calc R . .
C15 C 0.09396(17) 0.65934(8) 0.5621(2) 0.0287(4) Uani 1 1 d . . .
C16 C -0.02586(19) 0.58578(9) 0.6719(2) 0.0349(5) Uani 1 1 d . . .
H16 H -0.0174 0.6156 0.7600 0.042 Uiso 1 1 calc R . .
C17 C 0.0099(2) 0.52332(10) 0.7372(2) 0.0421(5) Uani 1 1 d . . .
H17A H 0.0015 0.4941 0.6508 0.063 Uiso 1 1 calc R . .
H17B H -0.0491 0.5116 0.8054 0.063 Uiso 1 1 calc R . .
H17C H 0.1004 0.5235 0.7980 0.063 Uiso 1 1 calc R . .
C18 C -0.1615(2) 0.58992(10) 0.5688(3) 0.0451(5) Uani 1 1 d . . .
H18A H -0.1769 0.6313 0.5275 0.068 Uiso 1 1 calc R . .
H18B H -0.2266 0.5799 0.6306 0.068 Uiso 1 1 calc R . .
H18C H -0.1692 0.5612 0.4815 0.068 Uiso 1 1 calc R . .


_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 C15 1.211(2) . ?
O2 C15 1.323(2) . ?
O2 C16 1.472(2) . ?
O3 C11 1.323(2) . ?
O3 C12 1.476(2) . ?
O4 C11 1.199(2) . ?
O5 C9 1.205(2) . ?
N1 C15 1.380(2) . ?
N1 N2 1.401(2) . ?
N1 C1 1.452(2) . ?
N2 N3 1.401(2) . ?
N2 C11 1.437(2) . ?
N3 N4 1.376(2) . ?
N3 C9 1.379(3) . ?
N4 C2 1.289(2) . ?
C1 C2 1.511(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.483(3) . ?
C3 C4 1.392(3) . ?
C3 C8 1.401(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.371(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.506(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C13 1.504(3) . ?
C12 C14 1.509(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C17 1.502(3) . ?
C16 C18 1.509(3) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O2 C16 116.01(14) . . ?
C11 O3 C12 116.19(14) . . ?
C15 N1 N2 119.10(14) . . ?
C15 N1 C1 119.46(15) . . ?
N2 N1 C1 113.29(14) . . ?
N1 N2 N3 108.34(13) . . ?
N1 N2 C11 116.38(14) . . ?
N3 N2 C11 112.50(14) . . ?
N4 N3 C9 121.45(15) . . ?
N4 N3 N2 118.19(14) . . ?
C9 N3 N2 119.68(15) . . ?
C2 N4 N3 117.77(15) . . ?
N1 C1 C2 108.07(15) . . ?
N1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
N4 C2 C3 116.51(16) . . ?
N4 C2 C1 124.69(16) . . ?
C3 C2 C1 118.80(16) . . ?
C4 C3 C8 118.41(17) . . ?
C4 C3 C2 121.77(17) . . ?
C8 C3 C2 119.76(16) . . ?
C5 C4 C3 120.35(19) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.65(19) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.11(18) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C8 C7 C6 120.82(19) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C3 120.66(18) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
O5 C9 N3 121.21(18) . . ?
O5 C9 C10 124.09(18) . . ?
N3 C9 C10 114.69(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 O3 128.02(17) . . ?
O4 C11 N2 123.04(17) . . ?
O3 C11 N2 108.83(14) . . ?
O3 C12 C13 109.20(16) . . ?
O3 C12 C14 104.99(16) . . ?
C13 C12 C14 113.60(19) . . ?
O3 C12 H12 109.6 . . ?
C13 C12 H12 109.6 . . ?
C14 C12 H12 109.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 O2 126.84(17) . . ?
O1 C15 N1 120.71(17) . . ?
O2 C15 N1 112.37(15) . . ?
O2 C16 C17 106.19(15) . . ?
O2 C16 C18 108.03(16) . . ?
C17 C16 C18 113.93(17) . . ?
O2 C16 H16 109.5 . . ?
C17 C16 H16 109.5 . . ?
C18 C16 H16 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 N2 N3 -148.16(15) . . . . ?
C1 N1 N2 N3 63.36(18) . . . . ?
C15 N1 N2 C11 83.9(2) . . . . ?
C1 N1 N2 C11 -64.54(19) . . . . ?
N1 N2 N3 N4 -50.39(19) . . . . ?
C11 N2 N3 N4 79.69(19) . . . . ?
N1 N2 N3 C9 138.84(17) . . . . ?
C11 N2 N3 C9 -91.1(2) . . . . ?
C9 N3 N4 C2 -172.23(17) . . . . ?
N2 N3 N4 C2 17.2(2) . . . . ?
C15 N1 C1 C2 169.67(15) . . . . ?
N2 N1 C1 C2 -41.97(19) . . . . ?
N3 N4 C2 C3 -175.26(14) . . . . ?
N3 N4 C2 C1 4.7(3) . . . . ?
N1 C1 C2 N4 7.7(2) . . . . ?
N1 C1 C2 C3 -172.31(14) . . . . ?
N4 C2 C3 C4 -175.85(16) . . . . ?
C1 C2 C3 C4 4.2(3) . . . . ?
N4 C2 C3 C8 7.3(3) . . . . ?
C1 C2 C3 C8 -172.70(16) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 C5 -176.57(17) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C3 -0.3(3) . . . . ?
C4 C3 C8 C7 -0.1(3) . . . . ?
C2 C3 C8 C7 176.90(16) . . . . ?
N4 N3 C9 O5 -174.53(18) . . . . ?
N2 N3 C9 O5 -4.1(3) . . . . ?
N4 N3 C9 C10 5.9(3) . . . . ?
N2 N3 C9 C10 176.37(17) . . . . ?
C12 O3 C11 O4 -2.2(3) . . . . ?
C12 O3 C11 N2 -178.61(14) . . . . ?
N1 N2 C11 O4 149.66(17) . . . . ?
N3 N2 C11 O4 23.8(2) . . . . ?
N1 N2 C11 O3 -33.7(2) . . . . ?
N3 N2 C11 O3 -159.50(14) . . . . ?
C11 O3 C12 C13 81.0(2) . . . . ?
C11 O3 C12 C14 -156.87(17) . . . . ?
C16 O2 C15 O1 3.9(3) . . . . ?
C16 O2 C15 N1 -179.16(14) . . . . ?
N2 N1 C15 O1 -154.86(16) . . . . ?
C1 N1 C15 O1 -8.3(3) . . . . ?
N2 N1 C15 O2 28.0(2) . . . . ?
C1 N1 C15 O2 174.55(14) . . . . ?
C15 O2 C16 C17 -152.16(16) . . . . ?
C15 O2 C16 C18 85.25(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.099
