# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1046817'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H27 N3 O6'
_chemical_formula_weight         465.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   13.228(5)
_cell_length_b                   9.602(3)
_cell_length_c                   17.978(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.418(7)
_cell_angle_gamma                90.00
_cell_volume                     2264.6(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    7907
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      27.9

_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    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_process_details   CrystalClear

_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 Saturn724 CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 14.22
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            23128
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         27.88
_reflns_number_total             5410
_reflns_number_gt                3859
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'

_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)+(0.0381P)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         5410
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0833
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_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 0.07419(7) 0.31280(9) 0.97033(5) 0.0299(2) Uani 1 1 d . . .
O2 O 0.31093(6) 0.24473(8) 0.91045(4) 0.0222(2) Uani 1 1 d . . .
O3 O 0.38755(6) 0.16612(8) 1.18031(4) 0.0228(2) Uani 1 1 d . . .
O4 O 0.29034(6) 0.34256(8) 1.21753(4) 0.0232(2) Uani 1 1 d . . .
O5 O 0.36022(7) 0.61915(9) 1.12656(5) 0.0312(2) Uani 1 1 d . . .
O6 O 0.19144(7) 0.65535(9) 1.09576(5) 0.0287(2) Uani 1 1 d . . .
N1 N 0.10985(7) 0.49125(10) 0.89135(5) 0.0210(2) Uani 1 1 d . . .
N2 N 0.35139(8) 0.24335(10) 1.03999(5) 0.0204(2) Uani 1 1 d . . .
N3 N 0.32598(8) 0.33058(10) 1.09833(5) 0.0206(2) Uani 1 1 d . . .
C1 C -0.06717(10) 0.53103(12) 0.71291(7) 0.0248(3) Uani 1 1 d . . .
H1 H -0.1186 0.5861 0.7308 0.030 Uiso 1 1 calc R . .
C2 C -0.07038(10) 0.50727(13) 0.63646(7) 0.0280(3) Uani 1 1 d . . .
H2 H -0.1237 0.5463 0.6023 0.034 Uiso 1 1 calc R . .
C3 C 0.00397(10) 0.42678(13) 0.60989(7) 0.0266(3) Uani 1 1 d . . .
H3 H 0.0018 0.4099 0.5576 0.032 Uiso 1 1 calc R . .
C4 C 0.08167(10) 0.37095(13) 0.66006(7) 0.0249(3) Uani 1 1 d . . .
H4 H 0.1329 0.3158 0.6420 0.030 Uiso 1 1 calc R . .
C5 C 0.08542(9) 0.39475(12) 0.73663(7) 0.0228(3) Uani 1 1 d . . .
H5 H 0.1391 0.3561 0.7706 0.027 Uiso 1 1 calc R . .
C6 C 0.01071(9) 0.47500(12) 0.76359(6) 0.0206(3) Uani 1 1 d . . .
C7 C 0.01032(9) 0.50244(13) 0.84679(6) 0.0245(3) Uani 1 1 d . . .
H7A H -0.0168 0.5972 0.8531 0.029 Uiso 1 1 calc R . .
H7B H -0.0366 0.4355 0.8664 0.029 Uiso 1 1 calc R . .
C8 C 0.19303(9) 0.58108(12) 0.88587(6) 0.0187(3) Uani 1 1 d . . .
C9 C 0.19867(10) 0.68837(12) 0.83563(6) 0.0226(3) Uani 1 1 d . . .
H9 H 0.1423 0.7120 0.7996 0.027 Uiso 1 1 calc R . .
C10 C 0.29052(10) 0.76059(13) 0.83996(7) 0.0241(3) Uani 1 1 d . . .
H10 H 0.2969 0.8348 0.8060 0.029 Uiso 1 1 calc R . .
C11 C 0.37261(10) 0.72700(12) 0.89251(6) 0.0227(3) Uani 1 1 d . . .
H11 H 0.4344 0.7779 0.8940 0.027 Uiso 1 1 calc R . .
C12 C 0.36514(9) 0.61859(12) 0.94343(6) 0.0212(3) Uani 1 1 d . . .
H12 H 0.4214 0.5949 0.9796 0.025 Uiso 1 1 calc R . .
C13 C 0.27443(9) 0.54678(12) 0.94002(6) 0.0181(3) Uani 1 1 d . . .
C14 C 0.24279(9) 0.42423(12) 0.98492(6) 0.0184(3) Uani 1 1 d . . .
C15 C 0.13139(9) 0.39887(12) 0.94929(6) 0.0216(3) Uani 1 1 d . . .
C16 C 0.30669(9) 0.29486(12) 0.97916(6) 0.0189(3) Uani 1 1 d . . .
C17 C 0.36391(9) 0.11206(12) 0.90556(6) 0.0218(3) Uani 1 1 d . . .
H17A H 0.3477 0.0746 0.8541 0.026 Uiso 1 1 calc R . .
H17B H 0.3384 0.0448 0.9405 0.026 Uiso 1 1 calc R . .
C18 C 0.47802(9) 0.12420(13) 0.92405(6) 0.0246(3) Uani 1 1 d . . .
H18A H 0.5029 0.1990 0.8941 0.037 Uiso 1 1 calc R . .
H18B H 0.5100 0.0360 0.9126 0.037 Uiso 1 1 calc R . .
H18C H 0.4954 0.1454 0.9775 0.037 Uiso 1 1 calc R . .
C19 C 0.33142(9) 0.28170(12) 1.17010(6) 0.0197(3) Uani 1 1 d . . .
C20 C 0.40231(10) 0.11211(14) 1.25680(6) 0.0275(3) Uani 1 1 d . . .
H20A H 0.3357 0.0903 1.2736 0.033 Uiso 1 1 calc R . .
H20B H 0.4377 0.1818 1.2914 0.033 Uiso 1 1 calc R . .
C21 C 0.46525(10) -0.01664(13) 1.25597(7) 0.0277(3) Uani 1 1 d . . .
H21A H 0.4275 -0.0868 1.2239 0.042 Uiso 1 1 calc R . .
H21B H 0.4804 -0.0530 1.3071 0.042 Uiso 1 1 calc R . .
H21C H 0.5291 0.0053 1.2363 0.042 Uiso 1 1 calc R . .
C22 C 0.24926(9) 0.43502(12) 1.07184(6) 0.0191(3) Uani 1 1 d . . .
H22 H 0.1823 0.4068 1.0873 0.023 Uiso 1 1 calc R . .
C23 C 0.27643(10) 0.57974(12) 1.10211(6) 0.0205(3) Uani 1 1 d . . .
C24 C 0.20187(12) 0.80238(13) 1.11644(8) 0.0356(4) Uani 1 1 d . . .
H24A H 0.2542 0.8127 1.1607 0.043 Uiso 1 1 calc R . .
H24B H 0.1363 0.8375 1.1301 0.043 Uiso 1 1 calc R . .
C25 C 0.23195(11) 0.88630(14) 1.05257(7) 0.0338(3) Uani 1 1 d . . .
H25A H 0.3001 0.8580 1.0426 0.051 Uiso 1 1 calc R . .
H25B H 0.2326 0.9854 1.0657 0.051 Uiso 1 1 calc R . .
H25C H 0.1829 0.8704 1.0077 0.051 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 1.2136(14) . ?
O2 C16 1.3336(13) . ?
O2 C17 1.4621(14) . ?
O3 C19 1.3348(14) . ?
O3 C20 1.4590(13) . ?
O4 C19 1.2180(13) . ?
O5 C23 1.1996(15) . ?
O6 C23 1.3308(15) . ?
O6 C24 1.4620(15) . ?
N1 C15 1.3698(15) . ?
N1 C8 1.4116(15) . ?
N1 C7 1.4542(15) . ?
N2 C16 1.2741(15) . ?
N2 N3 1.4162(13) . ?
N3 C19 1.3662(15) . ?
N3 C22 1.4621(15) . ?
C1 C2 1.3885(17) . ?
C1 C6 1.3924(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.3835(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3850(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3900(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3890(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.5195(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.3785(16) . ?
C8 C13 1.3947(16) . ?
C9 C10 1.3924(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3824(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3982(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3784(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.5162(16) . ?
C14 C16 1.5137(16) . ?
C14 C15 1.5483(18) . ?
C14 C22 1.5576(16) . ?
C17 C18 1.5077(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 C21 1.4917(17) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.5185(17) . ?
C22 H22 1.0000 . ?
C24 C25 1.4980(18) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C16 O2 C17 116.62(9) . . ?
C19 O3 C20 115.44(9) . . ?
C23 O6 C24 117.01(11) . . ?
C15 N1 C8 111.18(10) . . ?
C15 N1 C7 123.47(10) . . ?
C8 N1 C7 125.09(10) . . ?
C16 N2 N3 106.13(10) . . ?
C19 N3 N2 120.51(9) . . ?
C19 N3 C22 119.53(9) . . ?
N2 N3 C22 112.68(9) . . ?
C2 C1 C6 120.65(12) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.09(12) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.49(12) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.66(12) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.05(12) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.06(11) . . ?
C5 C6 C7 122.19(11) . . ?
C1 C6 C7 118.75(11) . . ?
N1 C7 C6 114.30(10) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C13 122.12(11) . . ?
C9 C8 N1 127.67(11) . . ?
C13 C8 N1 110.22(10) . . ?
C8 C9 C10 117.15(11) . . ?
C8 C9 H9 121.4 . . ?
C10 C9 H9 121.4 . . ?
C11 C10 C9 121.66(11) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.36(12) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 118.56(11) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C8 120.14(11) . . ?
C12 C13 C14 131.55(11) . . ?
C8 C13 C14 108.27(10) . . ?
C16 C14 C13 113.93(10) . . ?
C16 C14 C15 110.65(10) . . ?
C13 C14 C15 102.43(9) . . ?
C16 C14 C22 99.46(9) . . ?
C13 C14 C22 119.96(10) . . ?
C15 C14 C22 110.59(9) . . ?
O1 C15 N1 126.95(12) . . ?
O1 C15 C14 125.21(11) . . ?
N1 C15 C14 107.83(10) . . ?
N2 C16 O2 125.77(11) . . ?
N2 C16 C14 117.47(10) . . ?
O2 C16 C14 116.76(10) . . ?
O2 C17 C18 113.16(10) . . ?
O2 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
O2 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 O3 126.39(11) . . ?
O4 C19 N3 121.50(11) . . ?
O3 C19 N3 112.09(10) . . ?
O3 C20 C21 106.99(9) . . ?
O3 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
O3 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C23 112.88(10) . . ?
N3 C22 C14 103.13(9) . . ?
C23 C22 C14 113.60(9) . . ?
N3 C22 H22 109.0 . . ?
C23 C22 H22 109.0 . . ?
C14 C22 H22 109.0 . . ?
O5 C23 O6 126.14(12) . . ?
O5 C23 C22 125.79(11) . . ?
O6 C23 C22 108.07(11) . . ?
O6 C24 C25 110.50(10) . . ?
O6 C24 H24A 109.5 . . ?
C25 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C16 N2 N3 C19 157.57(11) . . . . ?
C16 N2 N3 C22 7.53(13) . . . . ?
C6 C1 C2 C3 0.27(19) . . . . ?
C1 C2 C3 C4 -0.34(19) . . . . ?
C2 C3 C4 C5 0.15(18) . . . . ?
C3 C4 C5 C6 0.12(18) . . . . ?
C4 C5 C6 C1 -0.20(17) . . . . ?
C4 C5 C6 C7 179.07(11) . . . . ?
C2 C1 C6 C5 0.00(18) . . . . ?
C2 C1 C6 C7 -179.29(11) . . . . ?
C15 N1 C7 C6 -120.20(12) . . . . ?
C8 N1 C7 C6 66.19(15) . . . . ?
C5 C6 C7 N1 24.38(16) . . . . ?
C1 C6 C7 N1 -156.35(11) . . . . ?
C15 N1 C8 C9 -178.68(11) . . . . ?
C7 N1 C8 C9 -4.39(18) . . . . ?
C15 N1 C8 C13 1.70(13) . . . . ?
C7 N1 C8 C13 175.98(10) . . . . ?
C13 C8 C9 C10 1.24(17) . . . . ?
N1 C8 C9 C10 -178.34(10) . . . . ?
C8 C9 C10 C11 -0.29(17) . . . . ?
C9 C10 C11 C12 -0.25(18) . . . . ?
C10 C11 C12 C13 -0.13(17) . . . . ?
C11 C12 C13 C8 1.05(17) . . . . ?
C11 C12 C13 C14 178.35(11) . . . . ?
C9 C8 C13 C12 -1.66(17) . . . . ?
N1 C8 C13 C12 177.99(10) . . . . ?
C9 C8 C13 C14 -179.53(10) . . . . ?
N1 C8 C13 C14 0.12(12) . . . . ?
C12 C13 C14 C16 -59.61(16) . . . . ?
C8 C13 C14 C16 117.93(11) . . . . ?
C12 C13 C14 C15 -179.15(12) . . . . ?
C8 C13 C14 C15 -1.60(12) . . . . ?
C12 C13 C14 C22 57.99(17) . . . . ?
C8 C13 C14 C22 -124.47(11) . . . . ?
C8 N1 C15 O1 176.57(11) . . . . ?
C7 N1 C15 O1 2.17(19) . . . . ?
C8 N1 C15 C14 -2.71(12) . . . . ?
C7 N1 C15 C14 -177.10(10) . . . . ?
C16 C14 C15 O1 61.50(15) . . . . ?
C13 C14 C15 O1 -176.70(11) . . . . ?
C22 C14 C15 O1 -47.72(15) . . . . ?
C16 C14 C15 N1 -119.21(10) . . . . ?
C13 C14 C15 N1 2.59(12) . . . . ?
C22 C14 C15 N1 131.57(10) . . . . ?
N3 N2 C16 O2 179.65(10) . . . . ?
N3 N2 C16 C14 -0.49(14) . . . . ?
C17 O2 C16 N2 5.97(17) . . . . ?
C17 O2 C16 C14 -173.89(10) . . . . ?
C13 C14 C16 N2 123.00(12) . . . . ?
C15 C14 C16 N2 -122.23(11) . . . . ?
C22 C14 C16 N2 -5.88(14) . . . . ?
C13 C14 C16 O2 -57.12(14) . . . . ?
C15 C14 C16 O2 57.65(13) . . . . ?
C22 C14 C16 O2 173.99(10) . . . . ?
C16 O2 C17 C18 -72.46(13) . . . . ?
C20 O3 C19 O4 -1.92(18) . . . . ?
C20 O3 C19 N3 176.37(10) . . . . ?
N2 N3 C19 O4 -164.24(10) . . . . ?
C22 N3 C19 O4 -16.21(17) . . . . ?
N2 N3 C19 O3 17.37(15) . . . . ?
C22 N3 C19 O3 165.40(10) . . . . ?
C19 O3 C20 C21 179.34(10) . . . . ?
C19 N3 C22 C23 75.78(13) . . . . ?
N2 N3 C22 C23 -133.85(9) . . . . ?
C19 N3 C22 C14 -161.23(10) . . . . ?
N2 N3 C22 C14 -10.86(12) . . . . ?
C16 C14 C22 N3 9.19(11) . . . . ?
C13 C14 C22 N3 -115.60(11) . . . . ?
C15 C14 C22 N3 125.59(10) . . . . ?
C16 C14 C22 C23 131.70(11) . . . . ?
C13 C14 C22 C23 6.91(15) . . . . ?
C15 C14 C22 C23 -111.90(11) . . . . ?
C24 O6 C23 O5 3.76(17) . . . . ?
C24 O6 C23 C22 -175.36(9) . . . . ?
N3 C22 C23 O5 20.54(16) . . . . ?
C14 C22 C23 O5 -96.41(14) . . . . ?
N3 C22 C23 O6 -160.33(9) . . . . ?
C14 C22 C23 O6 82.72(11) . . . . ?
C23 O6 C24 C25 82.78(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1046823'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 N4 O4'
_chemical_formula_weight         418.45

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8803(18)
_cell_length_b                   11.094(2)
_cell_length_c                   11.201(2)
_cell_angle_alpha                79.42(3)
_cell_angle_beta                 79.41(3)
_cell_angle_gamma                77.65(3)
_cell_volume                     1047.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2548
_cell_measurement_theta_min      1.9009
_cell_measurement_theta_max      27.8585

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_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    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9817
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10830
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0685
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         27.86
_reflns_number_total             4923
_reflns_number_gt                2370
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0572P)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     SHELXL
_refine_ls_extinction_coef       0.180(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4923
_refine_ls_number_parameters     300
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      1.013
_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 0.48754(14) 0.04311(11) 0.12343(11) 0.0521(3) Uani 1 1 d . . .
O2 O 0.48361(13) 0.32018(11) 0.20132(10) 0.0492(3) Uani 1 1 d . . .
O3 O 0.42513(16) 0.32787(13) -0.29555(12) 0.0672(4) Uani 1 1 d . . .
O4 O 0.26322(17) 0.46842(13) -0.18469(12) 0.0756(5) Uani 1 1 d D . .
N1 N 0.74197(16) 0.03220(12) 0.14846(12) 0.0441(4) Uani 1 1 d . . .
N2 N 0.40388(15) 0.37745(12) 0.01029(12) 0.0436(4) Uani 1 1 d . A .
N3 N 0.45715(16) 0.33698(14) -0.10419(13) 0.0505(4) Uani 1 1 d . . .
N4 N 0.8199(2) 0.27424(18) -0.27003(16) 0.0784(6) Uani 1 1 d . A .
C1 C 0.7592(2) -0.07866(16) 0.24137(16) 0.0532(5) Uani 1 1 d . . .
H1A H 0.8556 -0.1345 0.2170 0.064 Uiso 1 1 calc R . .
H1B H 0.6739 -0.1219 0.2457 0.064 Uiso 1 1 calc R . .
C2 C 0.7608(2) -0.04795(16) 0.36697(16) 0.0473(4) Uani 1 1 d . . .
C3 C 0.8536(2) -0.12553(19) 0.44528(18) 0.0632(6) Uani 1 1 d . . .
H3A H 0.9195 -0.1961 0.4195 0.076 Uiso 1 1 calc R . .
C4 C 0.8506(3) -0.1005(2) 0.56192(19) 0.0782(7) Uani 1 1 d . . .
H4A H 0.9133 -0.1548 0.6144 0.094 Uiso 1 1 calc R . .
C5 C 0.7557(3) 0.0041(2) 0.60095(19) 0.0735(6) Uani 1 1 d . . .
H5A H 0.7532 0.0207 0.6798 0.088 Uiso 1 1 calc R . .
C6 C 0.6654(3) 0.0833(2) 0.5236(2) 0.0774(7) Uani 1 1 d . . .
H6A H 0.6021 0.1551 0.5490 0.093 Uiso 1 1 calc R . .
C7 C 0.6669(3) 0.0575(2) 0.40710(19) 0.0709(6) Uani 1 1 d . . .
H7A H 0.6038 0.1120 0.3551 0.085 Uiso 1 1 calc R . .
C8 C 0.85206(19) 0.11169(15) 0.11327(15) 0.0421(4) Uani 1 1 d . . .
C9 C 1.0025(2) 0.08875(18) 0.13822(17) 0.0555(5) Uani 1 1 d . . .
H9A H 1.0444 0.0135 0.1827 0.067 Uiso 1 1 calc R . .
C10 C 1.0894(2) 0.1820(2) 0.09456(18) 0.0614(5) Uani 1 1 d . . .
H10A H 1.1922 0.1684 0.1084 0.074 Uiso 1 1 calc R . .
C11 C 1.0264(2) 0.29470(19) 0.03100(18) 0.0580(5) Uani 1 1 d . . .
H11A H 1.0861 0.3567 0.0046 0.070 Uiso 1 1 calc R . .
C12 C 0.8745(2) 0.31632(17) 0.00616(16) 0.0495(5) Uani 1 1 d . . .
H12A H 0.8318 0.3921 -0.0368 0.059 Uiso 1 1 calc R . .
C13 C 0.78849(18) 0.22298(15) 0.04656(14) 0.0393(4) Uani 1 1 d . A .
C14 C 0.62541(18) 0.21544(14) 0.03180(14) 0.0375(4) Uani 1 1 d . . .
C15 C 0.6062(2) 0.08590(15) 0.10568(14) 0.0405(4) Uani 1 1 d . A .
C16 C 0.49576(18) 0.31240(15) 0.08279(15) 0.0387(4) Uani 1 1 d . A .
C17 C 0.3426(2) 0.39724(19) 0.25355(18) 0.0622(5) Uani 1 1 d . . .
H17A H 0.2521 0.3659 0.2444 0.075 Uiso 1 1 calc R . .
H17B H 0.3347 0.4823 0.2110 0.075 Uiso 1 1 calc R . .
C18 C 0.3481(3) 0.3945(2) 0.38616(19) 0.0867(7) Uani 1 1 d . . .
H18A H 0.2550 0.4451 0.4219 0.130 Uiso 1 1 calc R . .
H18B H 0.4374 0.4264 0.3944 0.130 Uiso 1 1 calc R . .
H18C H 0.3555 0.3101 0.4277 0.130 Uiso 1 1 calc R . .
C19 C 0.58671(19) 0.22978(15) -0.10093(15) 0.0418(4) Uani 1 1 d . A .
H19A H 0.5513 0.1551 -0.1115 0.050 Uiso 1 1 calc R . .
C20 C 0.7175(2) 0.25398(17) -0.19715(17) 0.0504(5) Uani 1 1 d . . .
C21 C 0.3819(2) 0.37474(18) -0.20331(17) 0.0518(5) Uani 1 1 d . A .
C22 C 0.1518(6) 0.4973(5) -0.2756(4) 0.0800(14) Uani 0.629(7) 1 d PDU A 1
H22A H 0.1666 0.4292 -0.3224 0.096 Uiso 0.629(7) 1 calc PR A 1
H22B H 0.0449 0.5112 -0.2343 0.096 Uiso 0.629(7) 1 calc PR A 1
C23 C 0.1871(6) 0.6110(4) -0.3563(5) 0.1041(17) Uani 0.629(7) 1 d PDU A 1
H23A H 0.1184 0.6348 -0.4170 0.156 Uiso 0.629(7) 1 calc PR A 1
H23B H 0.2932 0.5956 -0.3964 0.156 Uiso 0.629(7) 1 calc PR A 1
H23C H 0.1729 0.6771 -0.3083 0.156 Uiso 0.629(7) 1 calc PR A 1
C22' C 0.2216(8) 0.5499(8) -0.2996(6) 0.071(2) Uani 0.371(7) 1 d PDU A 2
H22C H 0.3042 0.5374 -0.3685 0.085 Uiso 0.371(7) 1 calc PR A 2
H22D H 0.1973 0.6374 -0.2900 0.085 Uiso 0.371(7) 1 calc PR A 2
C23' C 0.0794(9) 0.5038(9) -0.3142(8) 0.098(3) Uani 0.371(7) 1 d PDU A 2
H23D H 0.0388 0.5503 -0.3863 0.148 Uiso 0.371(7) 1 calc PR A 2
H23E H 0.0015 0.5149 -0.2433 0.148 Uiso 0.371(7) 1 calc PR A 2
H23F H 0.1071 0.4169 -0.3224 0.148 Uiso 0.371(7) 1 calc PR 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
O1 C15 1.2156(18) . ?
O2 C16 1.3294(18) . ?
O2 C17 1.448(2) . ?
O3 C21 1.205(2) . ?
O4 C21 1.328(2) . ?
O4 C22' 1.489(7) . ?
O4 C22 1.495(4) . ?
N1 C15 1.356(2) . ?
N1 C8 1.410(2) . ?
N1 C1 1.458(2) . ?
N2 C16 1.274(2) . ?
N2 N3 1.4025(19) . ?
N3 C21 1.355(2) . ?
N3 C19 1.468(2) . ?
N4 C20 1.136(2) . ?
C1 C2 1.510(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.369(3) . ?
C2 C7 1.380(3) . ?
C3 C4 1.379(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.356(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.383(3) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.376(2) . ?
C8 C13 1.385(2) . ?
C9 C10 1.387(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.379(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.389(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.378(2) . ?
C12 H12A 0.9300 . ?
C13 C14 1.509(2) . ?
C14 C16 1.504(2) . ?
C14 C15 1.548(2) . ?
C14 C19 1.559(2) . ?
C17 C18 1.490(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.466(2) . ?
C19 H19A 0.9800 . ?
C22 C23 1.467(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C22' C23' 1.505(8) . ?
C22' H22C 0.9700 . ?
C22' H22D 0.9700 . ?
C23' H23D 0.9600 . ?
C23' H23E 0.9600 . ?
C23' H23F 0.9600 . ?

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
C16 O2 C17 115.98(13) . . ?
C21 O4 C22' 113.8(3) . . ?
C21 O4 C22 115.3(2) . . ?
C22' O4 C22 35.6(3) . . ?
C15 N1 C8 111.05(13) . . ?
C15 N1 C1 123.84(14) . . ?
C8 N1 C1 123.66(14) . . ?
C16 N2 N3 106.30(13) . . ?
C21 N3 N2 124.61(15) . . ?
C21 N3 C19 121.14(15) . . ?
N2 N3 C19 113.16(13) . . ?
N1 C1 C2 112.55(14) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C7 118.07(17) . . ?
C3 C2 C1 120.78(17) . . ?
C7 C2 C1 121.13(15) . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C4 C3 120.33(19) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6A 119.9 . . ?
C7 C6 H6A 119.9 . . ?
C2 C7 C6 120.92(18) . . ?
C2 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C9 C8 C13 121.92(16) . . ?
C9 C8 N1 127.73(15) . . ?
C13 C8 N1 110.35(14) . . ?
C8 C9 C10 117.46(16) . . ?
C8 C9 H9A 121.3 . . ?
C10 C9 H9A 121.3 . . ?
C11 C10 C9 121.32(17) . . ?
C11 C10 H10A 119.3 . . ?
C9 C10 H10A 119.3 . . ?
C10 C11 C12 120.53(17) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C13 C12 C11 118.57(16) . . ?
C13 C12 H12A 120.7 . . ?
C11 C12 H12A 120.7 . . ?
C12 C13 C8 120.15(15) . . ?
C12 C13 C14 131.57(14) . . ?
C8 C13 C14 108.28(13) . . ?
C16 C14 C13 116.48(13) . . ?
C16 C14 C15 108.60(13) . . ?
C13 C14 C15 102.22(12) . . ?
C16 C14 C19 99.79(12) . . ?
C13 C14 C19 118.19(13) . . ?
C15 C14 C19 111.63(13) . . ?
O1 C15 N1 127.04(15) . . ?
O1 C15 C14 124.90(15) . . ?
N1 C15 C14 108.03(13) . . ?
N2 C16 O2 125.34(16) . . ?
N2 C16 C14 117.61(14) . . ?
O2 C16 C14 117.01(13) . . ?
O2 C17 C18 108.71(16) . . ?
O2 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
O2 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 N3 110.84(14) . . ?
C20 C19 C14 113.50(14) . . ?
N3 C19 C14 102.71(13) . . ?
C20 C19 H19A 109.9 . . ?
N3 C19 H19A 109.9 . . ?
C14 C19 H19A 109.9 . . ?
N4 C20 C19 178.4(2) . . ?
O3 C21 O4 126.88(17) . . ?
O3 C21 N3 121.63(18) . . ?
O4 C21 N3 111.46(17) . . ?
C23 C22 O4 105.5(5) . . ?
C23 C22 H22A 110.6 . . ?
O4 C22 H22A 110.6 . . ?
C23 C22 H22B 110.6 . . ?
O4 C22 H22B 110.6 . . ?
H22A C22 H22B 108.8 . . ?
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 . . ?
O4 C22' C23' 100.7(7) . . ?
O4 C22' H22C 111.6 . . ?
C23' C22' H22C 111.6 . . ?
O4 C22' H22D 111.6 . . ?
C23' C22' H22D 111.6 . . ?
H22C C22' H22D 109.4 . . ?
C22' C23' H23D 109.5 . . ?
C22' C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
C22' C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 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
C16 N2 N3 C21 173.30(16) . . . . ?
C16 N2 N3 C19 5.12(18) . . . . ?
C15 N1 C1 C2 -101.98(19) . . . . ?
C8 N1 C1 C2 63.1(2) . . . . ?
N1 C1 C2 C3 -143.94(18) . . . . ?
N1 C1 C2 C7 37.3(2) . . . . ?
C7 C2 C3 C4 1.4(3) . . . . ?
C1 C2 C3 C4 -177.31(19) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C3 C2 C7 C6 -0.7(3) . . . . ?
C1 C2 C7 C6 178.05(19) . . . . ?
C5 C6 C7 C2 -0.6(3) . . . . ?
C15 N1 C8 C9 -179.13(17) . . . . ?
C1 N1 C8 C9 14.1(3) . . . . ?
C15 N1 C8 C13 0.97(19) . . . . ?
C1 N1 C8 C13 -165.76(15) . . . . ?
C13 C8 C9 C10 0.4(3) . . . . ?
N1 C8 C9 C10 -179.51(16) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 C12 -1.7(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C8 1.7(3) . . . . ?
C11 C12 C13 C14 -177.99(17) . . . . ?
C9 C8 C13 C12 -2.0(3) . . . . ?
N1 C8 C13 C12 177.92(14) . . . . ?
C9 C8 C13 C14 177.77(15) . . . . ?
N1 C8 C13 C14 -2.32(18) . . . . ?
C12 C13 C14 C16 -59.5(2) . . . . ?
C8 C13 C14 C16 120.79(15) . . . . ?
C12 C13 C14 C15 -177.68(17) . . . . ?
C8 C13 C14 C15 2.60(16) . . . . ?
C12 C13 C14 C19 59.4(2) . . . . ?
C8 C13 C14 C19 -120.36(16) . . . . ?
C8 N1 C15 O1 -177.58(16) . . . . ?
C1 N1 C15 O1 -10.9(3) . . . . ?
C8 N1 C15 C14 0.79(17) . . . . ?
C1 N1 C15 C14 167.49(14) . . . . ?
C16 C14 C15 O1 52.7(2) . . . . ?
C13 C14 C15 O1 176.37(16) . . . . ?
C19 C14 C15 O1 -56.3(2) . . . . ?
C16 C14 C15 N1 -125.70(14) . . . . ?
C13 C14 C15 N1 -2.04(16) . . . . ?
C19 C14 C15 N1 125.24(14) . . . . ?
N3 N2 C16 O2 -178.57(14) . . . . ?
N3 N2 C16 C14 -0.93(19) . . . . ?
C17 O2 C16 N2 8.6(2) . . . . ?
C17 O2 C16 C14 -169.09(13) . . . . ?
C13 C14 C16 N2 125.30(15) . . . . ?
C15 C14 C16 N2 -120.04(15) . . . . ?
C19 C14 C16 N2 -3.12(18) . . . . ?
C13 C14 C16 O2 -56.85(18) . . . . ?
C15 C14 C16 O2 57.80(17) . . . . ?
C19 C14 C16 O2 174.73(13) . . . . ?
C16 O2 C17 C18 179.55(16) . . . . ?
C21 N3 C19 C20 63.0(2) . . . . ?
N2 N3 C19 C20 -128.38(15) . . . . ?
C21 N3 C19 C14 -175.46(15) . . . . ?
N2 N3 C19 C14 -6.83(17) . . . . ?
C16 C14 C19 C20 125.17(14) . . . . ?
C13 C14 C19 C20 -2.1(2) . . . . ?
C15 C14 C19 C20 -120.21(16) . . . . ?
C16 C14 C19 N3 5.45(15) . . . . ?
C13 C14 C19 N3 -121.83(14) . . . . ?
C15 C14 C19 N3 120.07(14) . . . . ?
N3 C19 C20 N4 81(8) . . . . ?
C14 C19 C20 N4 -34(8) . . . . ?
C22' O4 C21 O3 -24.0(4) . . . . ?
C22 O4 C21 O3 15.3(4) . . . . ?
C22' O4 C21 N3 154.1(3) . . . . ?
C22 O4 C21 N3 -166.6(3) . . . . ?
N2 N3 C21 O3 -172.67(16) . . . . ?
C19 N3 C21 O3 -5.4(3) . . . . ?
N2 N3 C21 O4 9.1(3) . . . . ?
C19 N3 C21 O4 176.43(14) . . . . ?
C21 O4 C22 C23 -104.3(4) . . . . ?
C22' O4 C22 C23 -8.1(6) . . . . ?
C21 O4 C22' C23' 102.3(5) . . . . ?
C22 O4 C22' C23' 1.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.065
