# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_10e

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H27 N5 O4'
_chemical_formula_sum            'C17 H27 N5 O4'
_chemical_formula_weight         365.44

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           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

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

_cell_length_a                   9.359(4)
_cell_length_b                   10.657(4)
_cell_length_c                   19.105(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1905.4(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    458
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      18.85

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9854
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5498
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_sigmaI/netI    0.1733
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3104
_reflns_number_gt                1663
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0597P)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       0.027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3104
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1407
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.906
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL SKA360 in P2(1)2(1)2(1)
CELL 0.71073 9.3586 10.6572 19.1047 90.000 90.000 90.000
ZERR 4.00 0.0036 0.0044 0.0069 0.000 0.000 0.000
LATT -1
SYMM x+1/2, -y+1/2, -z
SYMM -x, y+1/2, -z+1/2
SYMM -x+1/2, -y, z+1/2
SFAC C H N O
UNIT 68 108 20 16
TEMP -123
ACTA
BOND $H
CONF
HTAB
L.S. 12
OMIT -1 50
SIZE 0.16 0.10 0.05
FMAP 2
PLAN 5
WGHT    0.059700
EXTI    0.027292
FVAR       0.24200
N1    3    0.682119    0.781714    0.218383    11.00000    0.03509    0.03500 =
         0.02866   -0.00155    0.00478    0.00036
N2    3    0.582325    0.743357    0.264813    11.00000    0.04344    0.04514 =
         0.02853   -0.00681    0.00412    0.00003
N3    3    0.579884    0.617886    0.260671    11.00000    0.03769    0.04388 =
         0.03568    0.00767    0.00192   -0.00151
N4    3    0.645750    0.579829   -0.022464    11.00000    0.02019    0.03556 =
         0.03671    0.00515   -0.00565    0.00330
AFIX  43
H4    2    0.564389    0.609321   -0.038668    11.00000   -1.20000
AFIX   0
N5    3    0.667509    0.851025    0.020037    11.00000    0.02400    0.02794 =
         0.03146   -0.00421    0.00100   -0.00450
AFIX  43
H5    2    0.573841    0.858129    0.019229    11.00000   -1.20000
AFIX   0
O1    4    0.724017    0.431860    0.121550    11.00000    0.03110    0.03624 =
         0.03288    0.00696   -0.00165    0.00817
O2    4    0.495609    0.483772    0.101735    11.00000    0.03953    0.05023 =
         0.03128    0.00295    0.00135    0.00169
O3    4    0.878865    0.612872   -0.005959    11.00000    0.02472    0.03325 =
         0.05771    0.00620   -0.00192   -0.00223
O4    4    0.868199    0.888499    0.082026    11.00000    0.02457    0.03317 =
         0.04118   -0.00148   -0.00155   -0.00333
C1    1    0.744906    0.683884    0.187214    11.00000    0.03007    0.04451 =
         0.03249    0.00301    0.00708   -0.00176
AFIX  43
H1    2    0.820094    0.686002    0.153827    11.00000   -1.20000
AFIX   0
C2    1    0.678769    0.581412    0.213261    11.00000    0.03330    0.04473 =
         0.02487    0.00536    0.00041    0.00251
C3    1    0.699311    0.447887    0.196302    11.00000    0.04420    0.03938 =
         0.03547    0.00723   -0.00467    0.00516
AFIX  23
H3A   2    0.782053    0.414736    0.222768    11.00000   -1.20000
H3B   2    0.613506    0.399789    0.210398    11.00000   -1.20000
AFIX   0
C4    1    0.611490    0.457720    0.078986    11.00000    0.03379    0.03295 =
         0.03855   -0.00257    0.00153   -0.00256
C5    1    0.651076    0.451152    0.003059    11.00000    0.02984    0.03198 =
         0.02717    0.00807    0.00038    0.00646
AFIX  13
H5A   2    0.751703    0.420315   -0.000701    11.00000   -1.20000
AFIX   0
C6    1    0.759958    0.654290   -0.022079    11.00000    0.02519    0.03148 =
         0.02662   -0.00125    0.00646   -0.00057
C7    1    0.738462    0.793190   -0.039495    11.00000    0.02144    0.02624 =
         0.03589   -0.00145    0.00635    0.00034
AFIX  13
H7    2    0.835112    0.832372   -0.044030    11.00000   -1.20000
AFIX   0
C8    1    0.737660    0.893552    0.075507    11.00000    0.03251    0.02670 =
         0.03294    0.00845   -0.00045   -0.00445
C9    1    0.646887    0.952799    0.132995    11.00000    0.03175    0.02456 =
         0.03037   -0.00184    0.00317    0.00236
AFIX  23
H9A   2    0.649972    1.045302    0.128484    11.00000   -1.20000
H9B   2    0.546330    0.925629    0.127594    11.00000   -1.20000
AFIX   0
C10   1    0.700744    0.915118    0.204658    11.00000    0.02964    0.03360 =
         0.04615   -0.00775    0.00439    0.00319
AFIX  23
H10A  2    0.803427    0.936433    0.208374    11.00000   -1.20000
H10B  2    0.648810    0.963778    0.240731    11.00000   -1.20000
AFIX   0
C11   1    0.554400    0.362148   -0.037714    11.00000    0.03440    0.02935 =
         0.04537    0.00015    0.00189    0.00262
AFIX  13
H11   2    0.454423    0.395081   -0.035772    11.00000   -1.20000
AFIX   0
C12   1    0.557671    0.233684   -0.002749    11.00000    0.05242    0.02901 =
         0.05716   -0.00212   -0.00339   -0.00096
AFIX 137
H12A  2    0.656461    0.203446   -0.000536    11.00000   -1.50000
H12B  2    0.499769    0.174620   -0.029975    11.00000   -1.50000
H12C  2    0.518886    0.240358    0.044754    11.00000   -1.50000
AFIX   0
C13   1    0.601695    0.358043   -0.113830    11.00000    0.04374    0.03404 =
         0.04341   -0.00313    0.00357    0.00252
AFIX  23
H13A  2    0.695322    0.315139   -0.116830    11.00000   -1.20000
H13B  2    0.614470    0.444930   -0.131063    11.00000   -1.20000
AFIX   0
C14   1    0.494499    0.289886   -0.161111    11.00000    0.04459    0.04280 =
         0.04889    0.00131   -0.00411   -0.00126
AFIX 137
H14A  2    0.485952    0.202241   -0.146164    11.00000   -1.50000
H14B  2    0.527961    0.292907   -0.209688    11.00000   -1.50000
H14C  2    0.401055    0.330939   -0.157706    11.00000   -1.50000
AFIX   0
C15   1    0.659725    0.813450   -0.108297    11.00000    0.02210    0.04227 =
         0.02866   -0.00005    0.00220    0.00200
AFIX  13
H15   2    0.566370    0.767920   -0.106444    11.00000   -1.20000
AFIX   0
C16   1    0.631260    0.951656   -0.120958    11.00000    0.04495    0.02974 =
         0.03893    0.00876    0.00498    0.00506
AFIX 137
H16A  2    0.574933    0.985701   -0.082108    11.00000   -1.50000
H16B  2    0.578146    0.961867   -0.164798    11.00000   -1.50000
H16C  2    0.722301    0.996729   -0.124152    11.00000   -1.50000
AFIX   0
C17   1    0.750241    0.758030   -0.167001    11.00000    0.05760    0.03620 =
         0.03880   -0.00130    0.00492    0.00728
AFIX 137
H17A  2    0.700430    0.768479   -0.211744    11.00000   -1.50000
H17B  2    0.766014    0.668529   -0.158116    11.00000   -1.50000
H17C  2    0.842465    0.801458   -0.168879    11.00000   -1.50000
HKLF   4
 
REM  SKA360 in P2(1)2(1)2(1)
REM R1 =  0.0719 for   1663 Fo > 4sig(Fo)  and  0.1384 for all   3104 data
REM    240 parameters refined using      0 restraints
 
END  
     
WGHT      0.0597      0.0000 
REM Highest difference peak  0.262,  deepest hole -0.231,  1-sigma level  0.062
Q1    1   0.7641  0.7434  0.0645  11.00000  0.05    0.26
Q2    1   0.8736  0.7663  0.0466  11.00000  0.05    0.24
Q3    1   0.6084  0.5004 -0.1163  11.00000  0.05    0.23
Q4    1   0.6959  0.8207 -0.0151  11.00000  0.05    0.22
Q5    1   0.5658  1.0578 -0.0493  11.00000  0.05    0.22
;

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
N1 N 0.6821(5) 0.7817(5) 0.2184(3) 0.0329(13) Uani 1 1 d . . .
N2 N 0.5823(5) 0.7434(5) 0.2648(3) 0.0390(14) Uani 1 1 d . . .
N3 N 0.5799(5) 0.6179(6) 0.2607(3) 0.0391(14) Uani 1 1 d . . .
N4 N 0.6458(4) 0.5798(4) -0.0225(2) 0.0308(13) Uani 1 1 d . . .
H4 H 0.5644 0.6093 -0.0387 0.037 Uiso 1 1 calc R . .
N5 N 0.6675(4) 0.8510(4) 0.0200(2) 0.0278(12) Uani 1 1 d . . .
H5 H 0.5738 0.8581 0.0192 0.033 Uiso 1 1 calc R . .
O1 O 0.7240(4) 0.4319(4) 0.1216(2) 0.0334(11) Uani 1 1 d . . .
O2 O 0.4956(4) 0.4838(4) 0.1017(2) 0.0403(12) Uani 1 1 d . . .
O3 O 0.8789(3) 0.6129(3) -0.0060(2) 0.0386(11) Uani 1 1 d . . .
O4 O 0.8682(4) 0.8885(3) 0.0820(2) 0.0330(10) Uani 1 1 d . . .
C1 C 0.7449(6) 0.6839(6) 0.1872(3) 0.0357(16) Uani 1 1 d . . .
H1 H 0.8201 0.6860 0.1538 0.043 Uiso 1 1 calc R . .
C2 C 0.6788(6) 0.5814(6) 0.2133(3) 0.0343(16) Uani 1 1 d . . .
C3 C 0.6993(7) 0.4479(6) 0.1963(3) 0.0397(17) Uani 1 1 d . . .
H3A H 0.7821 0.4147 0.2228 0.048 Uiso 1 1 calc R . .
H3B H 0.6135 0.3998 0.2104 0.048 Uiso 1 1 calc R . .
C4 C 0.6115(6) 0.4577(6) 0.0790(3) 0.0351(16) Uani 1 1 d . . .
C5 C 0.6511(5) 0.4512(5) 0.0031(3) 0.0297(14) Uani 1 1 d . . .
H5A H 0.7517 0.4203 -0.0007 0.036 Uiso 1 1 calc R . .
C6 C 0.7600(5) 0.6543(5) -0.0221(3) 0.0278(14) Uani 1 1 d . . .
C7 C 0.7385(5) 0.7932(5) -0.0395(3) 0.0279(14) Uani 1 1 d . . .
H7 H 0.8351 0.8324 -0.0440 0.033 Uiso 1 1 calc R . .
C8 C 0.7377(6) 0.8936(5) 0.0755(3) 0.0307(14) Uani 1 1 d . . .
C9 C 0.6469(6) 0.9528(6) 0.1330(3) 0.0289(14) Uani 1 1 d . . .
H9A H 0.6500 1.0453 0.1285 0.035 Uiso 1 1 calc R . .
H9B H 0.5463 0.9256 0.1276 0.035 Uiso 1 1 calc R . .
C10 C 0.7007(6) 0.9151(6) 0.2047(3) 0.0365(16) Uani 1 1 d . . .
H10A H 0.8034 0.9364 0.2084 0.044 Uiso 1 1 calc R . .
H10B H 0.6488 0.9638 0.2407 0.044 Uiso 1 1 calc R . .
C11 C 0.5544(6) 0.3621(6) -0.0377(3) 0.0364(16) Uani 1 1 d . . .
H11 H 0.4544 0.3951 -0.0358 0.044 Uiso 1 1 calc R . .
C12 C 0.5577(6) 0.2337(5) -0.0027(4) 0.0462(18) Uani 1 1 d . . .
H12A H 0.6565 0.2034 -0.0005 0.069 Uiso 1 1 calc R . .
H12B H 0.4998 0.1746 -0.0300 0.069 Uiso 1 1 calc R . .
H12C H 0.5189 0.2404 0.0448 0.069 Uiso 1 1 calc R . .
C13 C 0.6017(6) 0.3580(6) -0.1138(3) 0.0404(17) Uani 1 1 d . . .
H13A H 0.6953 0.3151 -0.1168 0.048 Uiso 1 1 calc R . .
H13B H 0.6145 0.4449 -0.1311 0.048 Uiso 1 1 calc R . .
C14 C 0.4945(6) 0.2899(6) -0.1611(4) 0.0454(18) Uani 1 1 d . . .
H14A H 0.4860 0.2022 -0.1462 0.068 Uiso 1 1 calc R . .
H14B H 0.5280 0.2929 -0.2097 0.068 Uiso 1 1 calc R . .
H14C H 0.4011 0.3309 -0.1577 0.068 Uiso 1 1 calc R . .
C15 C 0.6597(5) 0.8135(6) -0.1083(3) 0.0310(15) Uani 1 1 d . . .
H15 H 0.5664 0.7679 -0.1064 0.037 Uiso 1 1 calc R . .
C16 C 0.6313(6) 0.9517(5) -0.1210(3) 0.0379(16) Uani 1 1 d . . .
H16A H 0.5749 0.9857 -0.0821 0.057 Uiso 1 1 calc R . .
H16B H 0.5781 0.9619 -0.1648 0.057 Uiso 1 1 calc R . .
H16C H 0.7223 0.9967 -0.1242 0.057 Uiso 1 1 calc R . .
C17 C 0.7502(6) 0.7580(6) -0.1670(3) 0.0442(18) Uani 1 1 d . . .
H17A H 0.7004 0.7685 -0.2117 0.066 Uiso 1 1 calc R . .
H17B H 0.7660 0.6685 -0.1581 0.066 Uiso 1 1 calc R . .
H17C H 0.8425 0.8015 -0.1689 0.066 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
N1 C1 1.337(7) . ?
N1 N2 1.351(6) . ?
N1 C10 1.456(7) . ?
N2 N3 1.340(7) . ?
N3 C2 1.352(7) . ?
N4 C6 1.331(6) . ?
N4 C5 1.456(7) . ?
N4 H4 0.8800 . ?
N5 C8 1.326(7) . ?
N5 C7 1.454(6) . ?
N5 H5 0.8800 . ?
O1 C4 1.359(7) . ?
O1 C3 1.457(7) . ?
O2 C4 1.201(6) . ?
O3 C6 1.236(6) . ?
O4 C8 1.229(6) . ?
C1 C2 1.350(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.472(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.499(9) . ?
C5 C11 1.525(8) . ?
C5 H5A 1.0000 . ?
C6 C7 1.530(7) . ?
C7 C15 1.522(7) . ?
C7 H7 1.0000 . ?
C8 C9 1.525(8) . ?
C9 C10 1.513(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C13 1.521(8) . ?
C11 C12 1.524(8) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.533(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.516(8) . ?
C15 C17 1.525(7) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C1 N1 N2 111.1(5) . . ?
C1 N1 C10 129.0(5) . . ?
N2 N1 C10 119.8(5) . . ?
N3 N2 N1 106.0(5) . . ?
N2 N3 C2 108.4(5) . . ?
C6 N4 C5 122.1(4) . . ?
C6 N4 H4 118.9 . . ?
C5 N4 H4 118.9 . . ?
C8 N5 C7 122.9(4) . . ?
C8 N5 H5 118.5 . . ?
C7 N5 H5 118.5 . . ?
C4 O1 C3 116.1(5) . . ?
N1 C1 C2 105.4(5) . . ?
N1 C1 H1 127.3 . . ?
C2 C1 H1 127.3 . . ?
C1 C2 N3 109.2(6) . . ?
C1 C2 C3 129.9(6) . . ?
N3 C2 C3 121.0(6) . . ?
O1 C3 C2 110.5(5) . . ?
O1 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
O1 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
O2 C4 O1 122.0(6) . . ?
O2 C4 C5 125.8(6) . . ?
O1 C4 C5 112.2(5) . . ?
N4 C5 C4 105.8(5) . . ?
N4 C5 C11 113.2(5) . . ?
C4 C5 C11 112.1(5) . . ?
N4 C5 H5A 108.5 . . ?
C4 C5 H5A 108.5 . . ?
C11 C5 H5A 108.5 . . ?
O3 C6 N4 120.8(5) . . ?
O3 C6 C7 121.2(5) . . ?
N4 C6 C7 118.0(4) . . ?
N5 C7 C15 113.2(4) . . ?
N5 C7 C6 107.5(5) . . ?
C15 C7 C6 112.9(5) . . ?
N5 C7 H7 107.7 . . ?
C15 C7 H7 107.7 . . ?
C6 C7 H7 107.7 . . ?
O4 C8 N5 123.9(5) . . ?
O4 C8 C9 119.9(5) . . ?
N5 C8 C9 116.2(5) . . ?
C10 C9 C8 110.9(5) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 C9 112.5(5) . . ?
N1 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C13 C11 C12 112.8(5) . . ?
C13 C11 C5 109.5(5) . . ?
C12 C11 C5 108.8(5) . . ?
C13 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
C5 C11 H11 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 112.7(5) . . ?
C11 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C11 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C7 111.1(5) . . ?
C16 C15 C17 110.9(5) . . ?
C7 C15 C17 108.1(4) . . ?
C16 C15 H15 108.9 . . ?
C7 C15 H15 108.9 . . ?
C17 C15 H15 108.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C1 N1 N2 N3 -2.0(6) . . . . ?
C10 N1 N2 N3 173.6(5) . . . . ?
N1 N2 N3 C2 1.1(6) . . . . ?
N2 N1 C1 C2 2.1(7) . . . . ?
C10 N1 C1 C2 -172.9(6) . . . . ?
N1 C1 C2 N3 -1.4(7) . . . . ?
N1 C1 C2 C3 177.6(6) . . . . ?
N2 N3 C2 C1 0.2(7) . . . . ?
N2 N3 C2 C3 -178.9(5) . . . . ?
C4 O1 C3 C2 -67.7(7) . . . . ?
C1 C2 C3 O1 -38.4(9) . . . . ?
N3 C2 C3 O1 140.4(5) . . . . ?
C3 O1 C4 O2 -5.0(8) . . . . ?
C3 O1 C4 C5 174.2(5) . . . . ?
C6 N4 C5 C4 91.5(6) . . . . ?
C6 N4 C5 C11 -145.4(5) . . . . ?
O2 C4 C5 N4 68.5(8) . . . . ?
O1 C4 C5 N4 -110.7(5) . . . . ?
O2 C4 C5 C11 -55.4(8) . . . . ?
O1 C4 C5 C11 125.4(5) . . . . ?
C5 N4 C6 O3 6.9(8) . . . . ?
C5 N4 C6 C7 -170.9(5) . . . . ?
C8 N5 C7 C15 -149.8(5) . . . . ?
C8 N5 C7 C6 84.9(6) . . . . ?
O3 C6 C7 N5 -105.1(6) . . . . ?
N4 C6 C7 N5 72.7(6) . . . . ?
O3 C6 C7 C15 129.4(5) . . . . ?
N4 C6 C7 C15 -52.8(6) . . . . ?
C7 N5 C8 O4 0.1(9) . . . . ?
C7 N5 C8 C9 179.4(5) . . . . ?
O4 C8 C9 C10 -40.9(7) . . . . ?
N5 C8 C9 C10 139.7(5) . . . . ?
C1 N1 C10 C9 66.2(7) . . . . ?
N2 N1 C10 C9 -108.5(6) . . . . ?
C8 C9 C10 N1 -66.5(6) . . . . ?
N4 C5 C11 C13 61.4(6) . . . . ?
C4 C5 C11 C13 -179.0(5) . . . . ?
N4 C5 C11 C12 -174.9(5) . . . . ?
C4 C5 C11 C12 -55.3(6) . . . . ?
C12 C11 C13 C14 69.0(6) . . . . ?
C5 C11 C13 C14 -169.6(5) . . . . ?
N5 C7 C15 C16 53.5(6) . . . . ?
C6 C7 C15 C16 175.9(5) . . . . ?
N5 C7 C15 C17 175.5(5) . . . . ?
C6 C7 C15 C17 -62.2(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.934
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 957560'
