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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_007-14186
_database_code_depnum_ccdc_archive 'CCDC 1536046'
_audit_update_record             
;
2017-03-11 deposited with the CCDC.
2017-05-03 downloaded from the CCDC.
;

_vrf_RINTA01_007-14186           
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The diffraction data was not ideal due to crystal quality.
The numerous, disordered ethyl acetate solvent molecules contributed 
to a high crystal mosaicity.The crystal was also very small,
which exacerbated the already weak diffraction.
;
_vrf_PLAT605_007-14186           
; 
PROBLEM: Structure Contains Solvent Accessible VOIDS of .
RESPONSE: The solvent was disordered and its contribution to the
reflection list was removed using program PLATON function SQUEEZE. The
total VOID was determined to be 101.7 electrons in 427.4\%A^3^ 
(distributed over eight sites). See "_refine_special_details" for more
information.
;

_vrf_PLAT869_007-14186           
; 
PROBLEM: ALERTS Related to the use of SQUEEZE Suppressed
RESPONSE: See response to PLAT605
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 N4 O6'
_chemical_formula_sum            'C24 H28 N4 O6'
_chemical_formula_weight         468.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   16.7641(7)
_cell_length_b                   11.6113(4)
_cell_length_c                   14.8749(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.159(5)
_cell_angle_gamma                90
_cell_volume                     2681.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    10663
_cell_measurement_theta_min      2.8330
_cell_measurement_theta_max      65.5880

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.700
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40982
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            81113
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_av_R_equivalents  0.1919
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.846
_diffrn_reflns_theta_max         66.847
_diffrn_reflns_theta_full        66.847
_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             4754
_reflns_number_gt                3161
_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. 
  
 Structure factors included contributions from the .fab file. 
  
 _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       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 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. 

 The hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH groups and Uiso(H) 
 = 1.5 times Ueq(C) for CH3 groups. The only exception is H3, which is 
 freely refining and a part of a hydrogen bond between N3 and O3.

 The crystal structure reported here contains solvent accessible voids in 
 the unit cell. In spite of numerous attempts, no sensible solvent model 
 could be established, and the solvent is assumed to be disordered within 
 these voids. The crystals had been obtained from a ethyl acetate. 
 The program SQUEEZE was used to compensate for the contribution of 
 disordered solvents contained in voids within the crystal lattice from
 the diffraction intensities. This procedure was applied to the data file 
 and the submitted model is based on the solvent removed data. Based on
 the total electron density found in the voids, it is likely that 
 2 molecules of ethyl acetate molecules are present in the unit cell.
 See "_platon_squeeze_details" in this .cif for more information.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0925P)²+0.3334P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4754
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1691
_refine_ls_wR_factor_gt          0.1491
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.55559(12) 0.35095(15) 0.17364(13) 0.0405(5) Uani 1 1 d . . . . .
O2 O 0.87079(13) 0.2799(2) 0.75138(14) 0.0601(6) Uani 1 1 d . . . . .
O3 O 0.38780(12) 0.31822(16) 0.47647(13) 0.0445(5) Uani 1 1 d . . . . .
O4 O 0.40436(12) 0.40809(16) 0.26379(13) 0.0419(5) Uani 1 1 d . . . . .
O5 O 0.17525(13) 0.1397(2) 0.15912(16) 0.0638(6) Uani 1 1 d . . . . .
O6 O 0.21751(12) 0.2277(2) 0.30739(15) 0.0569(6) Uani 1 1 d . . . . .
N1 N 0.31459(14) 0.18741(18) 0.24439(15) 0.0374(5) Uani 1 1 d . . . . .
N2 N 0.37464(15) 0.41429(19) 0.34003(17) 0.0418(5) Uani 1 1 d . . . . .
N3 N 0.47252(15) 0.20256(18) 0.18351(17) 0.0373(5) Uani 1 1 d . . . . .
H3 H 0.4473(17) 0.201(2) 0.118(2) 0.039(8) Uiso 1 1 d . . . . .
N4 N 0.65955(13) 0.32371(18) 0.36583(15) 0.0354(5) Uani 1 1 d . . . . .
C1 C 0.38039(16) 0.2049(2) 0.33967(18) 0.0339(6) Uani 1 1 d . . . . .
C2 C 0.46364(16) 0.1527(2) 0.33842(18) 0.0337(6) Uani 1 1 d . . . . .
C3 C 0.44270(18) 0.1138(2) 0.23449(19) 0.0377(6) Uani 1 1 d . . . . .
H3A H 0.4703 0.0378 0.2329 0.045 Uiso 1 1 calc R U . . .
C4 C 0.34562(17) 0.1044(2) 0.18893(19) 0.0397(6) Uani 1 1 d . . . . .
H4A H 0.3241 0.1253 0.1193 0.048 Uiso 1 1 calc R U . . .
H4B H 0.3265 0.0252 0.1953 0.048 Uiso 1 1 calc R U . . .
C5 C 0.41624(17) 0.0972(2) 0.39592(19) 0.0377(6) Uani 1 1 d . . . . .
H5A H 0.3855 0.0241 0.3710 0.045 Uiso 1 1 calc R U . . .
H5B H 0.4424 0.1032 0.4676 0.045 Uiso 1 1 calc R U . . .
C6 C 0.38204(15) 0.3157(2) 0.39178(19) 0.0345(6) Uani 1 1 d . . . . .
C7 C 0.3886(2) 0.5265(2) 0.3878(2) 0.0530(8) Uani 1 1 d . . . . .
H7A H 0.4506 0.5403 0.4206 0.079 Uiso 1 1 calc R U . . .
H7B H 0.3613 0.5278 0.4355 0.079 Uiso 1 1 calc R U . . .
H7C H 0.3634 0.5868 0.3392 0.079 Uiso 1 1 calc R U . . .
C8 C 0.3382(2) 0.4427(3) 0.1740(2) 0.0576(8) Uani 1 1 d . . . . .
H8A H 0.3590 0.4334 0.1211 0.086 Uiso 1 1 calc R U . . .
H8B H 0.3235 0.5236 0.1784 0.086 Uiso 1 1 calc R U . . .
H8C H 0.2870 0.3947 0.1613 0.086 Uiso 1 1 calc R U . . .
C9 C 0.54980(16) 0.2049(2) 0.38811(18) 0.0337(6) Uani 1 1 d . . . . .
C10 C 0.59845(16) 0.1925(2) 0.48470(19) 0.0350(6) Uani 1 1 d . . . . .
H10 H 0.5770 0.1486 0.5246 0.042 Uiso 1 1 calc R U . . .
C11 C 0.68035(16) 0.2443(2) 0.52549(18) 0.0357(6) Uani 1 1 d . . . . .
C12 C 0.73466(17) 0.2319(2) 0.62399(19) 0.0401(6) Uani 1 1 d . . . . .
H12 H 0.7173 0.1856 0.6660 0.048 Uiso 1 1 calc R U . . .
C13 C 0.81197(18) 0.2867(3) 0.6583(2) 0.0461(7) Uani 1 1 d . . . . .
C14 C 0.83796(19) 0.3596(3) 0.5975(2) 0.0497(7) Uani 1 1 d . . . . .
H14 H 0.8912 0.3996 0.6237 0.060 Uiso 1 1 calc R U . . .
C15 C 0.78693(17) 0.3724(3) 0.5021(2) 0.0446(7) Uani 1 1 d . . . . .
H15 H 0.8049 0.4210 0.4619 0.054 Uiso 1 1 calc R U . . .
C16 C 0.70741(16) 0.3136(2) 0.46249(19) 0.0365(6) Uani 1 1 d . . . . .
C17 C 0.58480(16) 0.2703(2) 0.33053(18) 0.0341(6) Uani 1 1 d . . . . .
C18 C 0.53658(16) 0.2786(2) 0.22328(18) 0.0346(6) Uani 1 1 d . . . . .
C19 C 0.8503(2) 0.2058(4) 0.8160(2) 0.0747(12) Uani 1 1 d . . . . .
H19A H 0.8404 0.1276 0.7892 0.112 Uiso 1 1 calc R U . . .
H19B H 0.7982 0.2338 0.8240 0.112 Uiso 1 1 calc R U . . .
H19C H 0.8983 0.2050 0.8792 0.112 Uiso 1 1 calc R U . . .
C20 C 0.23014(18) 0.1814(3) 0.2313(2) 0.0469(7) Uani 1 1 d . . . . .
C21 C 0.1310(2) 0.2359(4) 0.3119(3) 0.0727(11) Uani 1 1 d . . . . .
C22 C 0.0908(3) 0.1170(4) 0.3031(3) 0.0910(14) Uani 1 1 d . . . . .
H22A H 0.0753 0.0885 0.2367 0.137 Uiso 1 1 calc R U . . .
H22B H 0.0389 0.1217 0.3185 0.137 Uiso 1 1 calc R U . . .
H22C H 0.1322 0.0642 0.3486 0.137 Uiso 1 1 calc R U . . .
C23 C 0.1521(3) 0.2852(4) 0.4126(3) 0.0870(14) Uani 1 1 d . . . . .
H23A H 0.1948 0.2361 0.4605 0.130 Uiso 1 1 calc R U . . .
H23B H 0.0997 0.2885 0.4268 0.130 Uiso 1 1 calc R U . . .
H23C H 0.1757 0.3630 0.4156 0.130 Uiso 1 1 calc R U . . .
C24 C 0.0770(3) 0.3162(5) 0.2347(4) 0.1024(16) Uani 1 1 d . . . . .
H24A H 0.1088 0.3878 0.2376 0.154 Uiso 1 1 calc R U . . .
H24B H 0.0237 0.3334 0.2447 0.154 Uiso 1 1 calc R U . . .
H24C H 0.0629 0.2802 0.1709 0.154 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 C18 1.237(3) . ?
O2 C13 1.366(3) . ?
O2 C19 1.425(4) . ?
O3 C6 1.227(3) . ?
O4 N2 1.402(3) . ?
O4 C8 1.434(3) . ?
O5 C20 1.220(3) . ?
O6 C20 1.340(3) . ?
O6 C21 1.480(4) . ?
N1 C20 1.356(3) . ?
N1 C1 1.445(3) . ?
N1 C4 1.485(3) . ?
N2 C6 1.359(3) . ?
N2 C7 1.460(3) . ?
N3 C18 1.343(3) . ?
N3 C3 1.474(3) . ?
N3 H3 0.90(3) . ?
N4 C17 1.317(3) . ?
N4 C16 1.362(3) . ?
C1 C6 1.497(3) . ?
C1 C5 1.498(4) . ?
C1 C2 1.528(3) . ?
C2 C9 1.481(4) . ?
C2 C5 1.514(3) . ?
C2 C3 1.519(4) . ?
C3 C4 1.513(4) . ?
C3 H3A 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.366(4) . ?
C9 C17 1.426(3) . ?
C10 C11 1.410(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.411(4) . ?
C11 C16 1.432(4) . ?
C12 C13 1.358(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.421(4) . ?
C14 C15 1.361(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.413(4) . ?
C15 H15 0.9500 . ?
C17 C18 1.495(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C24 1.491(6) . ?
C21 C23 1.516(5) . ?
C21 C22 1.520(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C13 O2 C19 116.9(2) . . ?
N2 O4 C8 110.7(2) . . ?
C20 O6 C21 122.3(2) . . ?
C20 N1 C1 121.2(2) . . ?
C20 N1 C4 116.9(2) . . ?
C1 N1 C4 109.8(2) . . ?
C6 N2 O4 115.5(2) . . ?
C6 N2 C7 120.9(2) . . ?
O4 N2 C7 113.5(2) . . ?
C18 N3 C3 127.1(2) . . ?
C18 N3 H3 117.5(18) . . ?
C3 N3 H3 115.2(18) . . ?
C17 N4 C16 118.3(2) . . ?
N1 C1 C6 119.1(2) . . ?
N1 C1 C5 115.3(2) . . ?
C6 C1 C5 120.2(2) . . ?
N1 C1 C2 107.2(2) . . ?
C6 C1 C2 120.6(2) . . ?
C5 C1 C2 60.01(16) . . ?
C9 C2 C5 120.9(2) . . ?
C9 C2 C3 115.9(2) . . ?
C5 C2 C3 118.6(2) . . ?
C9 C2 C1 123.7(2) . . ?
C5 C2 C1 59.03(16) . . ?
C3 C2 C1 105.6(2) . . ?
N3 C3 C4 109.7(2) . . ?
N3 C3 C2 108.8(2) . . ?
C4 C3 C2 105.9(2) . . ?
N3 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
N1 C4 C3 104.3(2) . . ?
N1 C4 H4A 110.9 . . ?
C3 C4 H4A 110.9 . . ?
N1 C4 H4B 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C1 C5 C2 60.97(17) . . ?
C1 C5 H5A 117.7 . . ?
C2 C5 H5A 117.7 . . ?
C1 C5 H5B 117.7 . . ?
C2 C5 H5B 117.7 . . ?
H5A C5 H5B 114.8 . . ?
O3 C6 N2 121.1(2) . . ?
O3 C6 C1 122.1(2) . . ?
N2 C6 C1 116.8(2) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C17 118.1(2) . . ?
C10 C9 C2 124.4(2) . . ?
C17 C9 C2 117.6(2) . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 123.1(2) . . ?
C10 C11 C16 117.1(2) . . ?
C12 C11 C16 119.8(2) . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 O2 125.2(3) . . ?
C12 C13 C14 121.2(3) . . ?
O2 C13 C14 113.7(3) . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
N4 C16 C15 119.1(2) . . ?
N4 C16 C11 122.2(2) . . ?
C15 C16 C11 118.7(2) . . ?
N4 C17 C9 123.8(2) . . ?
N4 C17 C18 116.4(2) . . ?
C9 C17 C18 119.7(2) . . ?
O1 C18 N3 121.8(2) . . ?
O1 C18 C17 121.6(2) . . ?
N3 C18 C17 116.6(2) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 O6 126.5(3) . . ?
O5 C20 N1 123.2(3) . . ?
O6 C20 N1 110.3(2) . . ?
O6 C21 C24 109.0(3) . . ?
O6 C21 C23 101.6(3) . . ?
C24 C21 C23 111.9(4) . . ?
O6 C21 C22 110.4(3) . . ?
C24 C21 C22 112.4(4) . . ?
C23 C21 C22 111.0(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C8 O4 N2 C6 125.0(3) . . . . ?
C8 O4 N2 C7 -89.2(3) . . . . ?
C20 N1 C1 C6 -64.7(3) . . . . ?
C4 N1 C1 C6 154.1(2) . . . . ?
C20 N1 C1 C5 89.5(3) . . . . ?
C4 N1 C1 C5 -51.7(3) . . . . ?
C20 N1 C1 C2 153.9(2) . . . . ?
C4 N1 C1 C2 12.7(3) . . . . ?
N1 C1 C2 C9 141.6(2) . . . . ?
C6 C1 C2 C9 0.9(4) . . . . ?
C5 C1 C2 C9 -108.6(3) . . . . ?
N1 C1 C2 C5 -109.8(2) . . . . ?
C6 C1 C2 C5 109.5(3) . . . . ?
N1 C1 C2 C3 4.6(3) . . . . ?
C6 C1 C2 C3 -136.2(2) . . . . ?
C5 C1 C2 C3 114.4(2) . . . . ?
C18 N3 C3 C4 141.6(2) . . . . ?
C18 N3 C3 C2 26.2(3) . . . . ?
C9 C2 C3 N3 -42.6(3) . . . . ?
C5 C2 C3 N3 161.1(2) . . . . ?
C1 C2 C3 N3 98.3(2) . . . . ?
C9 C2 C3 C4 -160.4(2) . . . . ?
C5 C2 C3 C4 43.3(3) . . . . ?
C1 C2 C3 C4 -19.5(3) . . . . ?
C20 N1 C4 C3 -167.9(2) . . . . ?
C1 N1 C4 C3 -24.8(3) . . . . ?
N3 C3 C4 N1 -90.4(2) . . . . ?
C2 C3 C4 N1 26.8(3) . . . . ?
N1 C1 C5 C2 96.0(2) . . . . ?
C6 C1 C5 C2 -110.1(3) . . . . ?
C9 C2 C5 C1 113.3(3) . . . . ?
C3 C2 C5 C1 -91.7(2) . . . . ?
O4 N2 C6 O3 154.1(2) . . . . ?
C7 N2 C6 O3 11.0(4) . . . . ?
O4 N2 C6 C1 -27.5(3) . . . . ?
C7 N2 C6 C1 -170.6(2) . . . . ?
N1 C1 C6 O3 131.2(3) . . . . ?
C5 C1 C6 O3 -21.8(4) . . . . ?
C2 C1 C6 O3 -92.6(3) . . . . ?
N1 C1 C6 N2 -47.2(3) . . . . ?
C5 C1 C6 N2 159.8(2) . . . . ?
C2 C1 C6 N2 89.0(3) . . . . ?
C5 C2 C9 C10 10.6(4) . . . . ?
C3 C2 C9 C10 -145.1(2) . . . . ?
C1 C2 C9 C10 81.8(3) . . . . ?
C5 C2 C9 C17 -170.9(2) . . . . ?
C3 C2 C9 C17 33.4(3) . . . . ?
C1 C2 C9 C17 -99.7(3) . . . . ?
C17 C9 C10 C11 0.7(3) . . . . ?
C2 C9 C10 C11 179.2(2) . . . . ?
C9 C10 C11 C12 -178.1(2) . . . . ?
C9 C10 C11 C16 2.8(4) . . . . ?
C10 C11 C12 C13 -178.6(3) . . . . ?
C16 C11 C12 C13 0.5(4) . . . . ?
C11 C12 C13 O2 -178.8(3) . . . . ?
C11 C12 C13 C14 2.2(4) . . . . ?
C19 O2 C13 C12 2.6(5) . . . . ?
C19 O2 C13 C14 -178.2(3) . . . . ?
C12 C13 C14 C15 -2.6(5) . . . . ?
O2 C13 C14 C15 178.2(3) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C17 N4 C16 C15 -178.6(2) . . . . ?
C17 N4 C16 C11 2.0(4) . . . . ?
C14 C15 C16 N4 -176.9(3) . . . . ?
C14 C15 C16 C11 2.4(4) . . . . ?
C10 C11 C16 N4 -4.3(4) . . . . ?
C12 C11 C16 N4 176.5(2) . . . . ?
C10 C11 C16 C15 176.4(2) . . . . ?
C12 C11 C16 C15 -2.8(4) . . . . ?
C16 N4 C17 C9 1.9(4) . . . . ?
C16 N4 C17 C18 -176.9(2) . . . . ?
C10 C9 C17 N4 -3.3(4) . . . . ?
C2 C9 C17 N4 178.1(2) . . . . ?
C10 C9 C17 C18 175.4(2) . . . . ?
C2 C9 C17 C18 -3.2(3) . . . . ?
C3 N3 C18 O1 -178.9(2) . . . . ?
C3 N3 C18 C17 2.0(4) . . . . ?
N4 C17 C18 O1 -15.4(3) . . . . ?
C9 C17 C18 O1 165.9(2) . . . . ?
N4 C17 C18 N3 163.7(2) . . . . ?
C9 C17 C18 N3 -15.1(3) . . . . ?
C21 O6 C20 O5 -1.3(5) . . . . ?
C21 O6 C20 N1 178.4(3) . . . . ?
C1 N1 C20 O5 -161.5(3) . . . . ?
C4 N1 C20 O5 -22.8(4) . . . . ?
C1 N1 C20 O6 18.9(4) . . . . ?
C4 N1 C20 O6 157.5(2) . . . . ?
C20 O6 C21 C24 -65.6(4) . . . . ?
C20 O6 C21 C23 176.2(3) . . . . ?
C20 O6 C21 C22 58.3(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
N3 H3 O3 0.90(3) 1.98(3) 2.874(3) 174(3) 4_565

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.052




