# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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. 
# 
#######################################################################

data_150326e_0m
_database_code_depnum_ccdc_archive 'CCDC 1587742'
_audit_update_record             
;
2017-11-27 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 N5 O4'
_chemical_formula_sum            'C22 H25 N5 O4'
_chemical_formula_weight         423.47

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                   9.324(3)
_cell_length_b                   9.760(3)
_cell_length_c                   12.772(4)
_cell_angle_alpha                75.736(6)
_cell_angle_beta                 70.173(5)
_cell_angle_gamma                77.227(5)
_cell_volume                     1047.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2371
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.57

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            7235
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.725
_diffrn_reflns_theta_max         27.673
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4847
_reflns_number_gt                3743
_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-2014 (Sheldrick, 2014)'
_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)+(0.0511P)²+0.5547P] 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         4847
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1226
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.11066(18) 0.55038(17) 0.32708(14) 0.0155(3) Uani 1 1 d . . . . .
C2 C 0.13822(18) 0.30439(16) 0.31187(14) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.20900(18) 0.46949(17) 0.15089(14) 0.0150(3) Uani 1 1 d . . . . .
C4 C 0.17223(18) 0.58221(16) 0.20891(14) 0.0148(3) Uani 1 1 d . . . . .
C5 C 0.18456(18) 0.73501(16) 0.14969(13) 0.0145(3) Uani 1 1 d . . . . .
H5 H 0.0863 0.7951 0.1851 0.017 Uiso 1 1 calc R U . . .
C6 C 0.31692(18) 0.79529(17) 0.15893(13) 0.0151(3) Uani 1 1 d . . . . .
C7 C 0.44723(19) 0.70830(17) 0.18065(15) 0.0189(3) Uani 1 1 d . . . . .
H7 H 0.4539 0.6073 0.1939 0.023 Uiso 1 1 calc R U . . .
C8 C 0.5681(2) 0.76814(19) 0.18317(16) 0.0230(4) Uani 1 1 d . . . . .
H8 H 0.6571 0.7078 0.1975 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5592(2) 0.9149(2) 0.16497(15) 0.0230(4) Uani 1 1 d . . . . .
H9 H 0.6419 0.9556 0.1666 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4289(2) 1.00254(18) 0.14431(15) 0.0220(4) Uani 1 1 d . . . . .
H10 H 0.4220 1.1035 0.1323 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3088(2) 0.94344(17) 0.14112(14) 0.0188(3) Uani 1 1 d . . . . .
H11 H 0.2201 1.0042 0.1267 0.023 Uiso 1 1 calc R U . . .
C12 C 0.20022(18) 0.75498(17) 0.02276(14) 0.0149(3) Uani 1 1 d . . . . .
H12 H 0.2468 0.8439 -0.0172 0.018 Uiso 1 1 calc R U . . .
C13 C 0.30769(18) 0.62927(17) -0.03083(14) 0.0150(3) Uani 1 1 d . . . . .
H13 H 0.4133 0.6314 -0.0284 0.018 Uiso 1 1 calc R U . . .
C14 C 0.32010(18) 0.64023(16) -0.15373(14) 0.0146(3) Uani 1 1 d . . . . .
C15 C 0.44152(19) 0.69918(18) -0.23836(15) 0.0191(3) Uani 1 1 d . . . . .
H15 H 0.5146 0.7337 -0.2185 0.023 Uiso 1 1 calc R U . . .
C16 C 0.4568(2) 0.7080(2) -0.35172(15) 0.0250(4) Uani 1 1 d . . . . .
H16 H 0.5403 0.7491 -0.4083 0.030 Uiso 1 1 calc R U . . .
C17 C 0.3531(2) 0.6584(2) -0.38418(15) 0.0246(4) Uani 1 1 d . . . . .
C18 C 0.2327(2) 0.59873(19) -0.29896(16) 0.0228(4) Uani 1 1 d . . . . .
H18 H 0.1610 0.5626 -0.3190 0.027 Uiso 1 1 calc R U . . .
C19 C 0.21470(19) 0.59069(18) -0.18526(15) 0.0188(3) Uani 1 1 d . . . . .
H19 H 0.1301 0.5512 -0.1288 0.023 Uiso 1 1 calc R U . . .
C20 C 0.3677(3) 0.6724(3) -0.50778(18) 0.0410(5) Uani 1 1 d . . . . .
H20A H 0.3194 0.7680 -0.5357 0.062 Uiso 1 1 calc R U . . .
H20B H 0.3161 0.6002 -0.5161 0.062 Uiso 1 1 calc R U . . .
H20C H 0.4770 0.6580 -0.5516 0.062 Uiso 1 1 calc R U . . .
C22 C 0.1368(3) 0.0177(2) 0.6595(2) 0.0405(5) Uani 1 1 d . . . . .
H22A H 0.1612 -0.0859 0.6576 0.049 Uiso 1 1 calc R U . . .
H22B H 0.1060 0.0280 0.7397 0.049 Uiso 1 1 calc R U . . .
C23 C 0.2766(3) 0.0827(3) 0.5974(2) 0.0545(7) Uani 1 1 d . . . . .
H23A H 0.3056 0.0773 0.5171 0.082 Uiso 1 1 calc R U . . .
H23B H 0.3606 0.0312 0.6284 0.082 Uiso 1 1 calc R U . . .
H23C H 0.2570 0.1830 0.6054 0.082 Uiso 1 1 calc R U . . .
N1 N 0.10004(16) 0.40781(14) 0.37567(12) 0.0158(3) Uani 1 1 d . . . . .
H1 H 0.0677 0.3834 0.4500 0.019 Uiso 1 1 calc R U . . .
N2 N 0.12009(18) 0.17100(15) 0.36694(13) 0.0235(3) Uani 1 1 d . . . . .
H2A H 0.1445 0.1011 0.3288 0.028 Uiso 1 1 calc R U . . .
H2B H 0.0838 0.1530 0.4413 0.028 Uiso 1 1 calc R U . . .
N3 N 0.19279(16) 0.33149(14) 0.20006(12) 0.0163(3) Uani 1 1 d . . . . .
N4 N 0.26357(17) 0.49319(14) 0.03622(12) 0.0188(3) Uani 1 1 d . . . . .
H4 H 0.2726 0.4233 0.0010 0.023 Uiso 1 1 calc R U . . .
N5 N 0.04450(16) 0.77533(15) 0.00605(12) 0.0190(3) Uani 1 1 d . . . . .
O1 O 0.06248(15) 0.63991(12) 0.39231(10) 0.0221(3) Uani 1 1 d . . . . .
O2 O -0.04217(15) 0.68898(15) 0.06186(13) 0.0333(3) Uani 1 1 d . . . . .
O3 O 0.01382(17) 0.87786(16) -0.06381(13) 0.0369(4) Uani 1 1 d . . . . .
O4 O 0.00862(16) 0.07791(13) 0.61619(12) 0.0293(3) Uani 1 1 d . . . . .
H4A H -0.0228 0.1621 0.6276 0.044 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
C1 O1 1.261(2) . ?
C1 N1 1.387(2) . ?
C1 C4 1.401(2) . ?
C2 N3 1.322(2) . ?
C2 N2 1.336(2) . ?
C2 N1 1.364(2) . ?
C3 N4 1.355(2) . ?
C3 N3 1.356(2) . ?
C3 C4 1.393(2) . ?
C4 C5 1.507(2) . ?
C5 C6 1.529(2) . ?
C5 C12 1.544(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.389(2) . ?
C6 C11 1.396(2) . ?
C7 C8 1.392(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 N5 1.502(2) . ?
C12 C13 1.544(2) . ?
C12 H12 1.0000 . ?
C13 N4 1.452(2) . ?
C13 C14 1.513(2) . ?
C13 H13 1.0000 . ?
C14 C15 1.390(2) . ?
C14 C19 1.392(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(3) . ?
C17 C20 1.512(3) . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C22 O4 1.435(3) . ?
C22 C23 1.465(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N4 H4 0.8800 . ?
N5 O2 1.219(2) . ?
N5 O3 1.2190(19) . ?
O4 H4A 0.8400 . ?

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
O1 C1 N1 117.57(15) . . ?
O1 C1 C4 125.76(15) . . ?
N1 C1 C4 116.67(14) . . ?
N3 C2 N2 120.03(14) . . ?
N3 C2 N1 122.70(14) . . ?
N2 C2 N1 117.26(15) . . ?
N4 C3 N3 114.49(14) . . ?
N4 C3 C4 120.42(15) . . ?
N3 C3 C4 125.08(15) . . ?
C3 C4 C1 117.13(14) . . ?
C3 C4 C5 122.89(14) . . ?
C1 C4 C5 119.80(14) . . ?
C4 C5 C6 115.00(13) . . ?
C4 C5 C12 111.54(13) . . ?
C6 C5 C12 107.92(13) . . ?
C4 C5 H5 107.3 . . ?
C6 C5 H5 107.3 . . ?
C12 C5 H5 107.3 . . ?
C7 C6 C11 118.81(15) . . ?
C7 C6 C5 122.44(14) . . ?
C11 C6 C5 118.72(14) . . ?
C6 C7 C8 120.45(16) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.30(16) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.62(16) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.25(16) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 120.56(16) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
N5 C12 C13 110.70(13) . . ?
N5 C12 C5 110.57(13) . . ?
C13 C12 C5 111.99(13) . . ?
N5 C12 H12 107.8 . . ?
C13 C12 H12 107.8 . . ?
C5 C12 H12 107.8 . . ?
N4 C13 C14 111.04(13) . . ?
N4 C13 C12 110.91(13) . . ?
C14 C13 C12 113.93(13) . . ?
N4 C13 H13 106.8 . . ?
C14 C13 H13 106.8 . . ?
C12 C13 H13 106.8 . . ?
C15 C14 C19 118.54(15) . . ?
C15 C14 C13 119.47(14) . . ?
C19 C14 C13 121.98(15) . . ?
C16 C15 C14 120.49(16) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 121.51(17) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 117.57(16) . . ?
C16 C17 C20 121.23(19) . . ?
C18 C17 C20 121.18(18) . . ?
C19 C18 C17 121.63(16) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C14 120.25(16) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C22 C23 114.45(19) . . ?
O4 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
O4 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C2 N1 C1 122.03(14) . . ?
C2 N1 H1 119.0 . . ?
C1 N1 H1 119.0 . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C2 N3 C3 116.27(14) . . ?
C3 N4 C13 122.62(13) . . ?
C3 N4 H4 118.7 . . ?
C13 N4 H4 118.7 . . ?
O2 N5 O3 124.29(15) . . ?
O2 N5 C12 118.58(14) . . ?
O3 N5 C12 117.13(14) . . ?
C22 O4 H4A 109.5 . . ?

_refine_diff_density_max         0.695
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3

