# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 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 
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and 
#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively. 
#
####################################################################### 

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 907213'
#TrackingRef 'shelxl 1.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N3 O3'
_chemical_formula_sum            'C16 H17 N3 O3'
_chemical_formula_weight         299.33
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'
_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                   7.9100(12)
_cell_length_b                   10.1440(16)
_cell_length_c                   19.501(2)
_cell_angle_alpha                99.419(19)
_cell_angle_beta                 90.797(3)
_cell_angle_gamma                105.56(2)
_cell_volume                     1484.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    1920
_cell_measurement_theta_min      27.60
_cell_measurement_theta_max      72.10
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8478
_exptl_absorpt_correction_T_max  0.8729
_exptl_absorpt_process_details   CrystalClear
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn944 CCD'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 11.11
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16631
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         72.46
_reflns_number_total             5563
_reflns_number_gt                4716
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r5'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r5'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0791P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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       0.086(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5563
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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 0.60388(15) 0.11142(12) 0.61662(7) 0.0454(3) Uani 1 1 d . . .
O2 O 0.77482(14) 0.54252(11) 0.48516(5) 0.0311(3) Uani 1 1 d . . .
O3 O 0.73806(15) 0.74808(12) 0.47022(6) 0.0358(3) Uani 1 1 d . . .
O4 O 0.95702(14) 0.93504(11) 0.09888(5) 0.0337(3) Uani 1 1 d . . .
O5 O 0.66577(13) 0.38914(11) -0.02246(5) 0.0283(3) Uani 1 1 d . . .
O6 O 0.65868(14) 0.16594(11) -0.02377(5) 0.0316(3) Uani 1 1 d . . .
N1 N 0.73764(16) 0.32429(13) 0.68296(6) 0.0299(3) Uani 1 1 d . . .
N2 N 0.90131(15) 0.43265(13) 0.68385(6) 0.0269(3) Uani 1 1 d . . .
N3 N 0.63511(15) 0.66630(12) 0.56438(6) 0.0253(3) Uani 1 1 d . . .
N4 N 0.88766(15) 0.77134(12) 0.17001(6) 0.0247(3) Uani 1 1 d . . .
N5 N 0.73068(15) 0.67068(12) 0.18584(6) 0.0238(3) Uani 1 1 d . . .
N6 N 0.85797(15) 0.32532(12) 0.04779(6) 0.0247(3) Uani 1 1 d . . .
C1 C 0.7359(2) 0.20657(16) 0.63650(8) 0.0321(4) Uani 1 1 d . . .
C2 C 0.9217(2) 0.21736(17) 0.61626(8) 0.0331(4) Uani 1 1 d . . .
H2A H 0.9323 0.2217 0.5661 0.040 Uiso 1 1 calc R . .
H2B H 0.9605 0.1372 0.6266 0.040 Uiso 1 1 calc R . .
C3 C 1.02892(19) 0.35244(16) 0.66108(7) 0.0284(3) Uani 1 1 d . . .
H3A H 1.0880 0.3331 0.7019 0.034 Uiso 1 1 calc R . .
H3B H 1.1195 0.4051 0.6338 0.034 Uiso 1 1 calc R . .
C4 C 0.5960(2) 0.39018(17) 0.68006(8) 0.0322(4) Uani 1 1 d . . .
H4A H 0.5729 0.4329 0.7271 0.039 Uiso 1 1 calc R . .
H4B H 0.4863 0.3229 0.6580 0.039 Uiso 1 1 calc R . .
C5 C 0.66886(17) 0.49966(15) 0.63560(7) 0.0254(3) Uani 1 1 d . . .
C6 C 0.86403(17) 0.51459(14) 0.63067(7) 0.0228(3) Uani 1 1 d . . .
H6 H 0.8878 0.4717 0.5832 0.027 Uiso 1 1 calc R . .
C7 C 0.57302(18) 0.56873(15) 0.60848(7) 0.0258(3) Uani 1 1 d . . .
H7 H 0.4533 0.5515 0.6195 0.031 Uiso 1 1 calc R . .
C8 C 0.72105(17) 0.64133(15) 0.50588(7) 0.0258(3) Uani 1 1 d . . .
C9 C 0.6752(2) 0.85563(17) 0.51095(9) 0.0383(4) Uani 1 1 d . . .
H9A H 0.6053 0.8943 0.4811 0.046 Uiso 1 1 calc R . .
H9B H 0.7744 0.9319 0.5350 0.046 Uiso 1 1 calc R . .
C10 C 0.5619(2) 0.78258(19) 0.56293(10) 0.0409(4) Uani 1 1 d . . .
H10A H 0.5754 0.8427 0.6092 0.049 Uiso 1 1 calc R . .
H10B H 0.4362 0.7510 0.5465 0.049 Uiso 1 1 calc R . .
C11 C 0.97196(17) 0.66506(15) 0.64764(7) 0.0253(3) Uani 1 1 d . . .
C12 C 1.08894(18) 0.72438(16) 0.60172(8) 0.0296(3) Uani 1 1 d . . .
H12 H 1.1113 0.6685 0.5607 0.035 Uiso 1 1 calc R . .
C13 C 1.1738(2) 0.86638(17) 0.61597(10) 0.0381(4) Uani 1 1 d . . .
H13 H 1.2542 0.9071 0.5846 0.046 Uiso 1 1 calc R . .
C14 C 1.1415(2) 0.94807(18) 0.67559(11) 0.0446(5) Uani 1 1 d . . .
H14 H 1.1977 1.0450 0.6847 0.053 Uiso 1 1 calc R . .
C15 C 1.0273(2) 0.88844(19) 0.72185(10) 0.0460(5) Uani 1 1 d . . .
H15 H 1.0065 0.9443 0.7632 0.055 Uiso 1 1 calc R . .
C16 C 0.9433(2) 0.74811(18) 0.70842(8) 0.0364(4) Uani 1 1 d . . .
H16 H 0.8655 0.7077 0.7407 0.044 Uiso 1 1 calc R . .
C17 C 0.84850(19) 0.85985(15) 0.12979(7) 0.0261(3) Uani 1 1 d . . .
C18 C 0.65541(19) 0.84777(16) 0.13301(8) 0.0304(3) Uani 1 1 d . . .
H18A H 0.5942 0.8133 0.0863 0.036 Uiso 1 1 calc R . .
H18B H 0.6353 0.9386 0.1520 0.036 Uiso 1 1 calc R . .
C19 C 0.59184(18) 0.74317(15) 0.18177(7) 0.0274(3) Uani 1 1 d . . .
H19A H 0.5751 0.7915 0.2285 0.033 Uiso 1 1 calc R . .
H19B H 0.4788 0.6760 0.1630 0.033 Uiso 1 1 calc R . .
C20 C 1.01690(18) 0.69599(15) 0.14996(7) 0.0262(3) Uani 1 1 d . . .
H20A H 1.0865 0.6889 0.1911 0.031 Uiso 1 1 calc R . .
H20B H 1.0976 0.7409 0.1170 0.031 Uiso 1 1 calc R . .
C21 C 0.90208(17) 0.55456(14) 0.11546(7) 0.0234(3) Uani 1 1 d . . .
C22 C 0.71221(17) 0.54837(14) 0.12869(7) 0.0231(3) Uani 1 1 d . . .
H22 H 0.6516 0.5623 0.0862 0.028 Uiso 1 1 calc R . .
C23 C 0.96428(18) 0.45596(15) 0.08082(7) 0.0249(3) Uani 1 1 d . . .
H23 H 1.0880 0.4743 0.0781 0.030 Uiso 1 1 calc R . .
C24 C 0.72364(17) 0.30431(15) -0.00044(7) 0.0244(3) Uani 1 1 d . . .
C25 C 0.7393(2) 0.08995(17) 0.01755(9) 0.0360(4) Uani 1 1 d . . .
H25A H 0.7729 0.0137 -0.0126 0.043 Uiso 1 1 calc R . .
H25B H 0.6578 0.0501 0.0516 0.043 Uiso 1 1 calc R . .
C26 C 0.9009(2) 0.19716(15) 0.05452(8) 0.0300(3) Uani 1 1 d . . .
H26A H 0.9145 0.1881 0.1039 0.036 Uiso 1 1 calc R . .
H26B H 1.0093 0.1904 0.0311 0.036 Uiso 1 1 calc R . .
C27 C 0.60905(17) 0.41647(15) 0.15213(7) 0.0241(3) Uani 1 1 d . . .
C28 C 0.44375(18) 0.34287(16) 0.12115(8) 0.0287(3) Uani 1 1 d . . .
H28 H 0.3931 0.3765 0.0855 0.034 Uiso 1 1 calc R . .
C29 C 0.35235(19) 0.21972(17) 0.14240(8) 0.0341(4) Uani 1 1 d . . .
H29 H 0.2399 0.1695 0.1209 0.041 Uiso 1 1 calc R . .
C30 C 0.4242(2) 0.17059(17) 0.19435(9) 0.0355(4) Uani 1 1 d . . .
H30 H 0.3617 0.0865 0.2085 0.043 Uiso 1 1 calc R . .
C31 C 0.5882(2) 0.24433(17) 0.22603(8) 0.0329(4) Uani 1 1 d . . .
H31 H 0.6375 0.2111 0.2622 0.039 Uiso 1 1 calc R . .
C32 C 0.67988(19) 0.36629(16) 0.20490(7) 0.0281(3) Uani 1 1 d . . .
H32 H 0.7922 0.4162 0.2266 0.034 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0364(6) 0.0279(6) 0.0691(8) 0.0112(6) -0.0013(5) 0.0028(5)
O2 0.0386(6) 0.0336(6) 0.0241(5) 0.0036(4) 0.0025(4) 0.0158(5)
O3 0.0436(6) 0.0344(6) 0.0362(6) 0.0164(5) 0.0109(5) 0.0158(5)
O4 0.0411(6) 0.0259(6) 0.0341(6) 0.0113(5) 0.0064(4) 0.0054(5)
O5 0.0314(5) 0.0270(6) 0.0279(5) 0.0079(4) -0.0001(4) 0.0090(4)
O6 0.0377(6) 0.0227(5) 0.0322(5) 0.0039(4) -0.0063(4) 0.0055(4)
N1 0.0305(6) 0.0303(7) 0.0314(6) 0.0142(5) 0.0073(5) 0.0071(5)
N2 0.0290(6) 0.0285(7) 0.0238(6) 0.0087(5) 0.0026(4) 0.0061(5)
N3 0.0261(6) 0.0227(6) 0.0286(6) 0.0057(5) 0.0040(4) 0.0082(5)
N4 0.0276(6) 0.0202(6) 0.0250(6) 0.0050(5) 0.0011(4) 0.0039(5)
N5 0.0266(6) 0.0197(6) 0.0242(6) 0.0050(5) 0.0015(4) 0.0040(5)
N6 0.0272(6) 0.0210(6) 0.0263(6) 0.0047(5) 0.0005(4) 0.0072(5)
C1 0.0362(8) 0.0257(8) 0.0370(8) 0.0125(7) 0.0025(6) 0.0087(6)
C2 0.0347(8) 0.0299(8) 0.0372(8) 0.0071(7) 0.0020(6) 0.0123(6)
C3 0.0307(7) 0.0321(8) 0.0256(7) 0.0082(6) 0.0012(5) 0.0123(6)
C4 0.0318(7) 0.0327(8) 0.0363(8) 0.0143(7) 0.0117(6) 0.0105(6)
C5 0.0264(7) 0.0244(8) 0.0233(7) 0.0033(6) 0.0044(5) 0.0037(6)
C6 0.0258(6) 0.0227(7) 0.0203(6) 0.0049(5) 0.0027(5) 0.0067(5)
C7 0.0231(6) 0.0242(7) 0.0280(7) 0.0046(6) 0.0050(5) 0.0029(5)
C8 0.0255(6) 0.0268(8) 0.0248(7) 0.0061(6) -0.0013(5) 0.0057(6)
C9 0.0451(9) 0.0282(9) 0.0464(9) 0.0132(7) 0.0084(7) 0.0138(7)
C10 0.0456(9) 0.0327(9) 0.0527(10) 0.0155(8) 0.0174(8) 0.0190(7)
C11 0.0234(6) 0.0235(8) 0.0278(7) 0.0026(6) -0.0015(5) 0.0058(5)
C12 0.0262(7) 0.0266(8) 0.0366(8) 0.0082(6) 0.0013(6) 0.0067(6)
C13 0.0290(7) 0.0285(9) 0.0573(10) 0.0158(8) -0.0008(7) 0.0039(6)
C14 0.0353(8) 0.0237(9) 0.0701(12) -0.0021(8) -0.0149(8) 0.0074(7)
C15 0.0407(9) 0.0356(10) 0.0526(10) -0.0156(8) -0.0076(8) 0.0093(8)
C16 0.0335(8) 0.0369(9) 0.0340(8) -0.0052(7) -0.0004(6) 0.0082(7)
C17 0.0372(7) 0.0197(7) 0.0205(6) 0.0022(5) 0.0009(5) 0.0069(6)
C18 0.0352(8) 0.0271(8) 0.0320(8) 0.0100(6) 0.0010(6) 0.0110(6)
C19 0.0303(7) 0.0257(8) 0.0282(7) 0.0065(6) 0.0032(5) 0.0100(6)
C20 0.0263(6) 0.0247(8) 0.0266(7) 0.0038(6) -0.0004(5) 0.0057(6)
C21 0.0257(6) 0.0233(7) 0.0212(6) 0.0069(5) 0.0001(5) 0.0049(5)
C22 0.0269(6) 0.0223(7) 0.0202(6) 0.0047(5) 0.0004(5) 0.0064(5)
C23 0.0259(6) 0.0230(7) 0.0254(7) 0.0058(6) 0.0003(5) 0.0053(5)
C24 0.0271(7) 0.0239(7) 0.0218(6) 0.0049(5) 0.0043(5) 0.0059(5)
C25 0.0442(8) 0.0231(8) 0.0402(9) 0.0074(7) -0.0070(7) 0.0076(7)
C26 0.0379(8) 0.0234(8) 0.0302(7) 0.0045(6) -0.0011(6) 0.0115(6)
C27 0.0263(6) 0.0218(7) 0.0244(7) 0.0029(5) 0.0048(5) 0.0073(6)
C28 0.0260(7) 0.0304(8) 0.0291(7) 0.0030(6) 0.0027(5) 0.0078(6)
C29 0.0258(7) 0.0314(9) 0.0407(8) 0.0021(7) 0.0064(6) 0.0023(6)
C30 0.0350(8) 0.0247(8) 0.0467(9) 0.0094(7) 0.0145(7) 0.0055(6)
C31 0.0382(8) 0.0287(8) 0.0354(8) 0.0126(7) 0.0075(6) 0.0108(6)
C32 0.0300(7) 0.0263(8) 0.0279(7) 0.0069(6) 0.0015(5) 0.0060(6)
_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 C1 1.224(2) . ?
O2 C8 1.2041(19) . ?
O3 C8 1.3583(18) . ?
O3 C9 1.445(2) . ?
O4 C17 1.2230(17) . ?
O5 C24 1.2089(17) . ?
O6 C24 1.3560(17) . ?
O6 C25 1.4503(18) . ?
N1 C1 1.373(2) . ?
N1 N2 1.4540(17) . ?
N1 C4 1.455(2) . ?
N2 C3 1.488(2) . ?
N2 C6 1.5028(17) . ?
N3 C8 1.3592(19) . ?
N3 C7 1.4105(18) . ?
N3 C10 1.451(2) . ?
N4 C17 1.3749(18) . ?
N4 N5 1.4537(16) . ?
N4 C20 1.454(2) . ?
N5 C19 1.4842(19) . ?
N5 C22 1.4996(19) . ?
N6 C24 1.3580(18) . ?
N6 C23 1.4092(18) . ?
N6 C26 1.4540(19) . ?
C1 C2 1.507(2) . ?
C2 C3 1.525(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5176(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C7 1.319(2) . ?
C5 C6 1.5162(18) . ?
C6 C11 1.5152(19) . ?
C6 H6 1.0000 . ?
C7 H7 0.9500 . ?
C9 C10 1.515(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.386(2) . ?
C11 C16 1.396(2) . ?
C12 C13 1.396(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.502(2) . ?
C18 C19 1.5297(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.5178(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C23 1.323(2) . ?
C21 C22 1.5137(19) . ?
C22 C27 1.5132(19) . ?
C22 H22 1.0000 . ?
C23 H23 0.9500 . ?
C25 C26 1.519(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.392(2) . ?
C27 C32 1.3930(19) . ?
C28 C29 1.396(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.378(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.386(2) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
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
C8 O3 C9 109.17(11) . . ?
C24 O6 C25 109.58(11) . . ?
C1 N1 N2 111.91(12) . . ?
C1 N1 C4 120.51(13) . . ?
N2 N1 C4 106.72(11) . . ?
N1 N2 C3 102.81(11) . . ?
N1 N2 C6 103.64(10) . . ?
C3 N2 C6 112.84(10) . . ?
C8 N3 C7 124.37(13) . . ?
C8 N3 C10 110.93(12) . . ?
C7 N3 C10 121.51(12) . . ?
C17 N4 N5 112.00(10) . . ?
C17 N4 C20 121.24(11) . . ?
N5 N4 C20 107.11(10) . . ?
N4 N5 C19 103.00(10) . . ?
N4 N5 C22 103.50(10) . . ?
C19 N5 C22 113.83(11) . . ?
C24 N6 C23 125.42(12) . . ?
C24 N6 C26 112.24(12) . . ?
C23 N6 C26 121.68(11) . . ?
O1 C1 N1 124.36(15) . . ?
O1 C1 C2 127.75(16) . . ?
N1 C1 C2 107.89(13) . . ?
C1 C2 C3 103.74(13) . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
N2 C3 C2 105.98(12) . . ?
N2 C3 H3A 110.5 . . ?
C2 C3 H3A 110.5 . . ?
N2 C3 H3B 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
N1 C4 C5 102.25(11) . . ?
N1 C4 H4A 111.3 . . ?
C5 C4 H4A 111.3 . . ?
N1 C4 H4B 111.3 . . ?
C5 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
C7 C5 C6 128.25(12) . . ?
C7 C5 C4 123.61(13) . . ?
C6 C5 C4 108.13(12) . . ?
N2 C6 C11 111.43(11) . . ?
N2 C6 C5 102.71(10) . . ?
C11 C6 C5 112.00(12) . . ?
N2 C6 H6 110.2 . . ?
C11 C6 H6 110.2 . . ?
C5 C6 H6 110.2 . . ?
C5 C7 N3 124.86(12) . . ?
C5 C7 H7 117.6 . . ?
N3 C7 H7 117.6 . . ?
O2 C8 O3 122.23(13) . . ?
O2 C8 N3 128.65(13) . . ?
O3 C8 N3 109.11(13) . . ?
O3 C9 C10 104.23(13) . . ?
O3 C9 H9A 110.9 . . ?
C10 C9 H9A 110.9 . . ?
O3 C9 H9B 110.9 . . ?
C10 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
N3 C10 C9 100.67(13) . . ?
N3 C10 H10A 111.6 . . ?
C9 C10 H10A 111.6 . . ?
N3 C10 H10B 111.6 . . ?
C9 C10 H10B 111.6 . . ?
H10A C10 H10B 109.4 . . ?
C12 C11 C16 119.35(14) . . ?
C12 C11 C6 121.36(13) . . ?
C16 C11 C6 119.12(13) . . ?
C11 C12 C13 119.82(16) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.29(16) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.83(16) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.36(17) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 120.34(16) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
O4 C17 N4 124.06(13) . . ?
O4 C17 C18 128.17(13) . . ?
N4 C17 C18 107.76(11) . . ?
C17 C18 C19 104.03(11) . . ?
C17 C18 H18A 111.0 . . ?
C19 C18 H18A 111.0 . . ?
C17 C18 H18B 111.0 . . ?
C19 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
N5 C19 C18 106.14(11) . . ?
N5 C19 H19A 110.5 . . ?
C18 C19 H19A 110.5 . . ?
N5 C19 H19B 110.5 . . ?
C18 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
N4 C20 C21 102.22(11) . . ?
N4 C20 H20A 111.3 . . ?
C21 C20 H20A 111.3 . . ?
N4 C20 H20B 111.3 . . ?
C21 C20 H20B 111.3 . . ?
H20A C20 H20B 109.2 . . ?
C23 C21 C22 127.73(13) . . ?
C23 C21 C20 123.74(12) . . ?
C22 C21 C20 108.53(12) . . ?
N5 C22 C27 110.18(11) . . ?
N5 C22 C21 102.06(10) . . ?
C27 C22 C21 114.46(12) . . ?
N5 C22 H22 110.0 . . ?
C27 C22 H22 110.0 . . ?
C21 C22 H22 110.0 . . ?
C21 C23 N6 123.92(13) . . ?
C21 C23 H23 118.0 . . ?
N6 C23 H23 118.0 . . ?
O5 C24 O6 122.12(12) . . ?
O5 C24 N6 128.91(13) . . ?
O6 C24 N6 108.96(12) . . ?
O6 C25 C26 104.80(12) . . ?
O6 C25 H25A 110.8 . . ?
C26 C25 H25A 110.8 . . ?
O6 C25 H25B 110.8 . . ?
C26 C25 H25B 110.8 . . ?
H25A C25 H25B 108.9 . . ?
N6 C26 C25 100.81(12) . . ?
N6 C26 H26A 111.6 . . ?
C25 C26 H26A 111.6 . . ?
N6 C26 H26B 111.6 . . ?
C25 C26 H26B 111.6 . . ?
H26A C26 H26B 109.4 . . ?
C28 C27 C32 119.05(13) . . ?
C28 C27 C22 120.90(12) . . ?
C32 C27 C22 120.05(12) . . ?
C27 C28 C29 120.05(14) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 120.39(14) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.86(14) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C32 C31 C30 119.99(14) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C27 120.66(13) . . ?
C31 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
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 C3 -26.40(14) . . . . ?
C4 N1 N2 C3 -160.20(11) . . . . ?
C1 N1 N2 C6 91.31(13) . . . . ?
C4 N1 N2 C6 -42.50(14) . . . . ?
C17 N4 N5 C19 -26.22(14) . . . . ?
C20 N4 N5 C19 -161.43(11) . . . . ?
C17 N4 N5 C22 92.59(13) . . . . ?
C20 N4 N5 C22 -42.62(12) . . . . ?
N2 N1 C1 O1 -165.91(14) . . . . ?
C4 N1 C1 O1 -39.3(2) . . . . ?
N2 N1 C1 C2 14.50(15) . . . . ?
C4 N1 C1 C2 141.15(12) . . . . ?
O1 C1 C2 C3 -176.15(15) . . . . ?
N1 C1 C2 C3 3.43(15) . . . . ?
N1 N2 C3 C2 27.02(13) . . . . ?
C6 N2 C3 C2 -83.97(13) . . . . ?
C1 C2 C3 N2 -19.20(14) . . . . ?
C1 N1 C4 C5 -94.36(15) . . . . ?
N2 N1 C4 C5 34.64(14) . . . . ?
N1 C4 C5 C7 167.29(14) . . . . ?
N1 C4 C5 C6 -14.00(15) . . . . ?
N1 N2 C6 C11 151.24(12) . . . . ?
C3 N2 C6 C11 -98.29(14) . . . . ?
N1 N2 C6 C5 31.17(13) . . . . ?
C3 N2 C6 C5 141.65(12) . . . . ?
C7 C5 C6 N2 168.17(15) . . . . ?
C4 C5 C6 N2 -10.46(15) . . . . ?
C7 C5 C6 C11 48.50(19) . . . . ?
C4 C5 C6 C11 -130.13(12) . . . . ?
C6 C5 C7 N3 4.6(2) . . . . ?
C4 C5 C7 N3 -176.93(14) . . . . ?
C8 N3 C7 C5 52.1(2) . . . . ?
C10 N3 C7 C5 -149.89(16) . . . . ?
C9 O3 C8 O2 -175.04(14) . . . . ?
C9 O3 C8 N3 5.90(16) . . . . ?
C7 N3 C8 O2 -8.3(2) . . . . ?
C10 N3 C8 O2 -168.28(15) . . . . ?
C7 N3 C8 O3 170.67(12) . . . . ?
C10 N3 C8 O3 10.70(16) . . . . ?
C8 O3 C9 C10 -18.98(17) . . . . ?
C8 N3 C10 C9 -21.35(17) . . . . ?
C7 N3 C10 C9 178.02(13) . . . . ?
O3 C9 C10 N3 23.37(17) . . . . ?
N2 C6 C11 C12 120.29(14) . . . . ?
C5 C6 C11 C12 -125.29(14) . . . . ?
N2 C6 C11 C16 -64.51(16) . . . . ?
C5 C6 C11 C16 49.92(16) . . . . ?
C16 C11 C12 C13 -1.2(2) . . . . ?
C6 C11 C12 C13 173.96(13) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C15 1.3(2) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C12 C11 C16 C15 1.5(2) . . . . ?
C6 C11 C16 C15 -173.78(14) . . . . ?
N5 N4 C17 O4 -165.47(13) . . . . ?
C20 N4 C17 O4 -37.4(2) . . . . ?
N5 N4 C17 C18 15.76(15) . . . . ?
C20 N4 C17 C18 143.81(13) . . . . ?
O4 C17 C18 C19 -177.44(14) . . . . ?
N4 C17 C18 C19 1.26(15) . . . . ?
N4 N5 C19 C18 25.40(14) . . . . ?
C22 N5 C19 C18 -85.94(13) . . . . ?
C17 C18 C19 N5 -16.92(15) . . . . ?
C17 N4 C20 C21 -98.19(13) . . . . ?
N5 N4 C20 C21 31.98(12) . . . . ?
N4 C20 C21 C23 170.96(12) . . . . ?
N4 C20 C21 C22 -9.74(13) . . . . ?
N4 N5 C22 C27 155.68(10) . . . . ?
C19 N5 C22 C27 -93.28(13) . . . . ?
N4 N5 C22 C21 33.70(12) . . . . ?
C19 N5 C22 C21 144.74(11) . . . . ?
C23 C21 C22 N5 164.57(13) . . . . ?
C20 C21 C22 N5 -14.69(13) . . . . ?
C23 C21 C22 C27 45.58(18) . . . . ?
C20 C21 C22 C27 -133.68(12) . . . . ?
C22 C21 C23 N6 1.9(2) . . . . ?
C20 C21 C23 N6 -178.96(11) . . . . ?
C24 N6 C23 C21 55.2(2) . . . . ?
C26 N6 C23 C21 -134.82(14) . . . . ?
C25 O6 C24 O5 -173.39(13) . . . . ?
C25 O6 C24 N6 7.64(16) . . . . ?
C23 N6 C24 O5 -2.6(2) . . . . ?
C26 N6 C24 O5 -173.45(14) . . . . ?
C23 N6 C24 O6 176.23(12) . . . . ?
C26 N6 C24 O6 5.43(16) . . . . ?
C24 O6 C25 C26 -16.78(16) . . . . ?
C24 N6 C26 C25 -15.04(16) . . . . ?
C23 N6 C26 C25 173.76(13) . . . . ?
O6 C25 C26 N6 18.30(16) . . . . ?
N5 C22 C27 C28 113.70(14) . . . . ?
C21 C22 C27 C28 -131.98(14) . . . . ?
N5 C22 C27 C32 -66.95(17) . . . . ?
C21 C22 C27 C32 47.37(18) . . . . ?
C32 C27 C28 C29 -0.8(2) . . . . ?
C22 C27 C28 C29 178.54(14) . . . . ?
C27 C28 C29 C30 0.4(2) . . . . ?
C28 C29 C30 C31 0.3(2) . . . . ?
C29 C30 C31 C32 -0.6(3) . . . . ?
C30 C31 C32 C27 0.2(2) . . . . ?
C28 C27 C32 C31 0.5(2) . . . . ?
C22 C27 C32 C31 -178.85(14) . . . . ?
_diffrn_measured_fraction_theta_max 0.946
_diffrn_reflns_theta_full        67.75
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.102