# Electronic Supplementary Material (ESI) for Chemical Science
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 911535'
#TrackingRef '10.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H27 N3 O3'
_chemical_formula_weight         453.53
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   P1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
_cell_length_a                   9.552(5)
_cell_length_b                   10.569(6)
_cell_length_c                   13.458(7)
_cell_angle_alpha                71.185(11)
_cell_angle_beta                 76.497(11)
_cell_angle_gamma                77.422(11)
_cell_volume                     1235.5(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1226
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      21.51
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      153(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8160
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0934
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         28.46
_reflns_number_total             7116
_reflns_number_gt                4019
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 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^)+(0.0782P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.0(16)
_refine_ls_number_reflns         7116
_refine_ls_number_parameters     633
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1617
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1494(5) 0.8183(5) 0.2247(4) 0.0298(10) Uani 1 1 d . . .
C2 C 0.1513(6) 0.9549(5) 0.1982(4) 0.0414(13) Uani 1 1 d . . .
H2 H 0.1134 1.0016 0.2508 0.050 Uiso 1 1 calc R . .
C3 C 0.2042(6) 0.7534(5) 0.1466(4) 0.0423(13) Uani 1 1 d . . .
H3 H 0.2024 0.6593 0.1631 0.051 Uiso 1 1 calc R . .
C4 C 0.2633(7) 0.9595(7) 0.0189(5) 0.0572(16) Uani 1 1 d . . .
H4 H 0.3024 1.0080 -0.0514 0.069 Uiso 1 1 calc R . .
C5 C 0.2619(7) 0.8245(7) 0.0442(4) 0.0546(16) Uani 1 1 d . . .
H5 H 0.3007 0.7783 -0.0086 0.065 Uiso 1 1 calc R . .
C6 C 0.2080(7) 1.0250(6) 0.0957(4) 0.0545(16) Uani 1 1 d . . .
H6 H 0.2086 1.1194 0.0783 0.065 Uiso 1 1 calc R . .
C7 C 0.0828(5) 0.7425(5) 0.3371(3) 0.0294(10) Uani 1 1 d . . .
H7A H 0.0228 0.6805 0.3314 0.035 Uiso 1 1 calc R . .
H7B H 0.0164 0.8091 0.3708 0.035 Uiso 1 1 calc R . .
C8 C 0.1915(5) 0.6594(4) 0.4118(3) 0.0260(10) Uani 1 1 d . . .
C9 C 0.2889(5) 0.7483(5) 0.4205(3) 0.0288(10) Uani 1 1 d . . .
H9 H 0.3874 0.7371 0.3853 0.035 Uiso 1 1 calc R . .
C10 C 0.2493(6) 0.8410(5) 0.4731(4) 0.0366(12) Uani 1 1 d . . .
H10 H 0.3216 0.8890 0.4749 0.044 Uiso 1 1 calc R . .
C11 C 0.1060(7) 0.8728(6) 0.5267(5) 0.0447(14) Uani 1 1 d . . .
C12 C 0.1659(5) 0.5171(4) 0.5967(3) 0.0260(10) Uani 1 1 d . . .
C13 C 0.0731(5) 0.4746(5) 0.7028(3) 0.0279(10) Uani 1 1 d . . .
C14 C 0.1072(5) 0.3490(5) 0.7699(4) 0.0351(11) Uani 1 1 d . . .
H14 H 0.1914 0.2906 0.7482 0.042 Uiso 1 1 calc R . .
C15 C 0.0218(6) 0.3047(5) 0.8693(4) 0.0402(12) Uani 1 1 d . . .
H15 H 0.0468 0.2167 0.9149 0.048 Uiso 1 1 calc R . .
C16 C -0.0496(5) 0.5606(5) 0.7355(4) 0.0354(11) Uani 1 1 d . . .
H16 H -0.0752 0.6481 0.6894 0.043 Uiso 1 1 calc R . .
C17 C -0.1336(6) 0.5183(6) 0.8349(4) 0.0433(13) Uani 1 1 d . . .
H17 H -0.2152 0.5781 0.8579 0.052 Uiso 1 1 calc R . .
C18 C -0.1000(6) 0.3897(6) 0.9011(4) 0.0413(13) Uani 1 1 d . . .
C19 C -0.1656(8) 0.2243(7) 1.0660(5) 0.073(2) Uani 1 1 d . . .
H19A H -0.1585 0.1573 1.0282 0.109 Uiso 1 1 calc R . .
H19B H -0.2458 0.2115 1.1271 0.109 Uiso 1 1 calc R . .
H19C H -0.0741 0.2129 1.0912 0.109 Uiso 1 1 calc R . .
C20 C 0.2850(5) 0.5451(4) 0.3672(3) 0.0266(10) Uani 1 1 d . . .
C21 C 0.2906(5) 0.3345(5) 0.3274(4) 0.0311(11) Uani 1 1 d . . .
H21 H 0.3957 0.3177 0.3339 0.037 Uiso 1 1 calc R . .
C22 C 0.2266(6) 0.2063(5) 0.3936(4) 0.0418(12) Uani 1 1 d . . .
H22A H 0.2509 0.1779 0.4652 0.063 Uiso 1 1 calc R . .
H22B H 0.2674 0.1342 0.3593 0.063 Uiso 1 1 calc R . .
H22C H 0.1205 0.2246 0.3989 0.063 Uiso 1 1 calc R . .
C23 C 0.2836(5) 0.3732(4) 0.2108(4) 0.0310(11) Uani 1 1 d . . .
C24 C 0.1507(6) 0.3854(5) 0.1775(4) 0.0415(12) Uani 1 1 d . . .
H24 H 0.0653 0.3663 0.2289 0.050 Uiso 1 1 calc R . .
C25 C 0.4044(6) 0.4014(5) 0.1328(4) 0.0456(13) Uani 1 1 d . . .
H25 H 0.4948 0.3944 0.1538 0.055 Uiso 1 1 calc R . .
C26 C 0.2677(8) 0.4492(6) -0.0051(4) 0.0584(16) Uani 1 1 d . . .
H26 H 0.2627 0.4728 -0.0787 0.070 Uiso 1 1 calc R . .
C27 C 0.3983(8) 0.4393(6) 0.0258(5) 0.0590(17) Uani 1 1 d . . .
H27 H 0.4832 0.4583 -0.0261 0.071 Uiso 1 1 calc R . .
C28 C 0.1451(8) 0.4253(6) 0.0701(4) 0.0563(16) Uani 1 1 d . . .
H28 H 0.0546 0.4363 0.0481 0.068 Uiso 1 1 calc R . .
C29 C 0.8102(6) 0.3124(5) 0.5982(4) 0.0416(13) Uani 1 1 d . . .
H29A H 0.8845 0.2560 0.5591 0.050 Uiso 1 1 calc R . .
H29B H 0.8606 0.3744 0.6139 0.050 Uiso 1 1 calc R . .
C30 C 0.7433(5) 0.2218(5) 0.7017(4) 0.0367(12) Uani 1 1 d . . .
C31 C 0.7478(6) 0.0855(6) 0.7142(4) 0.0472(14) Uani 1 1 d . . .
H31 H 0.7942 0.0496 0.6563 0.057 Uiso 1 1 calc R . .
C32 C 0.6868(7) 0.0011(6) 0.8083(5) 0.0574(16) Uani 1 1 d . . .
H32 H 0.6906 -0.0917 0.8147 0.069 Uiso 1 1 calc R . .
C33 C 0.6208(8) 0.0508(8) 0.8925(5) 0.0687(19) Uani 1 1 d . . .
H33 H 0.5802 -0.0075 0.9580 0.082 Uiso 1 1 calc R . .
C34 C 0.6767(8) 0.2693(7) 0.7870(5) 0.0599(17) Uani 1 1 d . . .
H34 H 0.6737 0.3618 0.7812 0.072 Uiso 1 1 calc R . .
C35 C 0.6133(9) 0.1855(9) 0.8819(6) 0.079(2) Uani 1 1 d . . .
H35 H 0.5649 0.2213 0.9394 0.095 Uiso 1 1 calc R . .
C36 C 0.7000(5) 0.3970(5) 0.5258(4) 0.0325(11) Uani 1 1 d . . .
C37 C 0.6047(5) 0.3060(5) 0.5164(4) 0.0328(11) Uani 1 1 d . . .
H37 H 0.5095 0.3094 0.5580 0.039 Uiso 1 1 calc R . .
C38 C 0.6391(6) 0.2219(5) 0.4566(4) 0.0370(12) Uani 1 1 d . . .
H38 H 0.5686 0.1681 0.4616 0.044 Uiso 1 1 calc R . .
C39 C 0.7740(7) 0.2057(5) 0.3853(5) 0.0437(14) Uani 1 1 d . . .
C40 C 0.6487(5) 0.6018(5) 0.5861(4) 0.0342(11) Uani 1 1 d . . .
C41 C 0.5363(5) 0.6952(5) 0.6384(4) 0.0326(11) Uani 1 1 d . . .
C42 C 0.3285(6) 0.8807(6) 0.7219(4) 0.0447(13) Uani 1 1 d . . .
C43 C 0.4027(6) 0.6601(5) 0.6968(4) 0.0374(12) Uani 1 1 d . . .
H43 H 0.3822 0.5721 0.7079 0.045 Uiso 1 1 calc R . .
C44 C 0.4633(6) 0.9140(6) 0.6685(4) 0.0470(14) Uani 1 1 d . . .
H44 H 0.4852 1.0008 0.6597 0.056 Uiso 1 1 calc R . .
C45 C 0.2993(6) 0.7521(6) 0.7388(4) 0.0421(13) Uani 1 1 d . . .
H45 H 0.2087 0.7270 0.7791 0.051 Uiso 1 1 calc R . .
C46 C 0.5665(6) 0.8213(6) 0.6277(4) 0.0448(13) Uani 1 1 d . . .
H46 H 0.6596 0.8446 0.5919 0.054 Uiso 1 1 calc R . .
C47 C 0.0872(7) 0.9564(8) 0.8040(6) 0.0695(19) Uani 1 1 d . . .
H47A H 0.0482 0.9238 0.7572 0.104 Uiso 1 1 calc R . .
H47B H 0.0266 1.0409 0.8133 0.104 Uiso 1 1 calc R . .
H47C H 0.0867 0.8882 0.8736 0.104 Uiso 1 1 calc R . .
C48 C 0.7826(5) 0.4683(5) 0.4149(4) 0.0341(11) Uani 1 1 d . . .
C49 C 0.7512(6) 0.6326(5) 0.2398(4) 0.0372(12) Uani 1 1 d . . .
H49 H 0.8591 0.6257 0.2319 0.045 Uiso 1 1 calc R . .
C50 C 0.6840(5) 0.7737(5) 0.2425(4) 0.0371(12) Uani 1 1 d . . .
C51 C 0.7105(6) 0.8185(5) 0.3231(4) 0.0452(13) Uani 1 1 d . . .
H51 H 0.7694 0.7592 0.3724 0.054 Uiso 1 1 calc R . .
C52 C 0.7220(7) 0.5900(6) 0.1495(4) 0.0561(17) Uani 1 1 d . . .
H52A H 0.7669 0.4957 0.1557 0.084 Uiso 1 1 calc R . .
H52B H 0.7638 0.6483 0.0808 0.084 Uiso 1 1 calc R . .
H52C H 0.6167 0.5986 0.1539 0.084 Uiso 1 1 calc R . .
C53 C 0.5679(7) 1.0321(6) 0.2615(5) 0.0546(15) Uani 1 1 d . . .
H53 H 0.5329 1.1224 0.2644 0.066 Uiso 1 1 calc R . .
C54 C 0.6531(7) 0.9460(6) 0.3323(5) 0.0549(15) Uani 1 1 d . . .
H54 H 0.6724 0.9743 0.3873 0.066 Uiso 1 1 calc R . .
C55 C 0.5912(7) 0.8595(6) 0.1786(5) 0.0556(16) Uani 1 1 d . . .
H55 H 0.5649 0.8309 0.1264 0.067 Uiso 1 1 calc R . .
C56 C 0.5344(7) 0.9884(6) 0.1886(5) 0.0648(18) Uani 1 1 d . . .
H56 H 0.4704 1.0467 0.1426 0.078 Uiso 1 1 calc R . .
H57 H 0.530(6) 0.490(5) 0.592(4) 0.025(15) Uiso 1 1 d . . .
H58 H 0.137(5) 0.447(4) 0.410(3) 0.018(12) Uiso 1 1 d . . .
H59 H 0.594(10) 0.536(8) 0.351(6) 0.12(3) Uiso 1 1 d . . .
H60 H 0.029(6) 0.617(5) 0.525(4) 0.031(16) Uiso 1 1 d . . .
N1 N -0.0118(7) 0.9019(5) 0.5669(5) 0.0673(15) Uani 1 1 d . . .
N2 N 0.1042(5) 0.6022(4) 0.5148(3) 0.0263(9) Uani 1 1 d . . .
N3 N 0.2181(5) 0.4452(4) 0.3727(3) 0.0279(9) Uani 1 1 d . . .
N4 N 0.8785(6) 0.1910(6) 0.3263(4) 0.0679(17) Uani 1 1 d . . .
N5 N 0.6020(5) 0.5000(4) 0.5712(4) 0.0344(11) Uani 1 1 d . . .
N6 N 0.6998(5) 0.5386(4) 0.3436(3) 0.0348(10) Uani 1 1 d . . .
O1 O 0.4133(3) 0.5519(3) 0.3236(2) 0.0330(7) Uani 1 1 d . . .
O2 O 0.3002(3) 0.4775(3) 0.5829(2) 0.0310(7) Uani 1 1 d . . .
O3 O -0.1926(4) 0.3569(4) 0.9956(3) 0.0561(11) Uani 1 1 d . . .
O4 O 0.9164(3) 0.4608(4) 0.3963(3) 0.0418(9) Uani 1 1 d . . .
O5 O 0.7764(3) 0.6219(3) 0.5567(3) 0.0377(8) Uani 1 1 d . . .
O6 O 0.2344(5) 0.9802(4) 0.7570(3) 0.0595(11) Uani 1 1 d . . .
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
C1 0.025(3) 0.026(3) 0.036(2) -0.010(2) -0.007(2) 0.005(2)
C2 0.046(3) 0.033(3) 0.045(3) -0.009(2) -0.014(3) -0.004(2)
C3 0.053(4) 0.035(3) 0.037(3) -0.013(2) -0.012(3) 0.005(3)
C4 0.049(4) 0.062(5) 0.047(3) 0.004(3) -0.014(3) -0.005(3)
C5 0.058(4) 0.065(5) 0.036(3) -0.016(3) -0.011(3) 0.007(3)
C6 0.068(4) 0.039(4) 0.052(3) 0.005(3) -0.024(3) -0.013(3)
C7 0.023(2) 0.029(3) 0.036(2) -0.014(2) -0.007(2) 0.0073(19)
C8 0.019(2) 0.027(3) 0.031(2) -0.011(2) -0.001(2) 0.0001(19)
C9 0.027(3) 0.026(3) 0.033(2) -0.006(2) -0.007(2) -0.007(2)
C10 0.041(3) 0.027(3) 0.045(3) -0.010(2) -0.012(3) -0.008(2)
C11 0.053(4) 0.029(3) 0.057(3) -0.024(3) -0.001(3) -0.008(3)
C12 0.025(3) 0.023(3) 0.031(2) -0.013(2) -0.005(2) -0.0004(19)
C13 0.028(3) 0.026(3) 0.032(2) -0.009(2) -0.008(2) -0.005(2)
C14 0.034(3) 0.034(3) 0.035(2) -0.011(2) -0.007(2) 0.003(2)
C15 0.042(3) 0.040(3) 0.034(3) -0.007(2) -0.005(2) -0.004(2)
C16 0.029(3) 0.044(3) 0.035(2) -0.016(2) 0.000(2) -0.006(2)
C17 0.037(3) 0.046(3) 0.044(3) -0.019(3) -0.004(3) 0.003(2)
C18 0.035(3) 0.053(4) 0.035(3) -0.015(3) 0.001(2) -0.009(3)
C19 0.073(5) 0.076(5) 0.047(3) 0.003(3) 0.006(3) -0.018(4)
C20 0.028(3) 0.019(2) 0.031(2) -0.0077(19) -0.004(2) -0.003(2)
C21 0.027(3) 0.023(3) 0.044(3) -0.018(2) -0.004(2) 0.006(2)
C22 0.048(3) 0.024(3) 0.053(3) -0.012(2) -0.010(3) -0.001(2)
C23 0.032(3) 0.016(2) 0.045(3) -0.017(2) 0.001(2) -0.001(2)
C24 0.041(3) 0.046(3) 0.043(3) -0.022(2) -0.004(2) -0.009(3)
C25 0.040(3) 0.031(3) 0.059(3) -0.019(3) 0.006(3) 0.000(2)
C26 0.079(5) 0.054(4) 0.038(3) -0.014(3) -0.003(3) -0.010(3)
C27 0.069(5) 0.048(4) 0.051(3) -0.023(3) 0.020(3) -0.012(3)
C28 0.077(5) 0.053(4) 0.047(3) -0.017(3) -0.019(3) -0.012(3)
C29 0.025(3) 0.031(3) 0.068(3) -0.012(3) -0.013(3) 0.000(2)
C30 0.027(3) 0.039(3) 0.048(3) -0.017(3) -0.013(2) 0.001(2)
C31 0.045(4) 0.043(4) 0.053(3) -0.020(3) -0.011(3) 0.006(3)
C32 0.067(4) 0.038(4) 0.067(4) -0.006(3) -0.023(4) -0.007(3)
C33 0.065(5) 0.067(5) 0.059(4) -0.001(4) -0.012(4) -0.004(4)
C34 0.077(5) 0.050(4) 0.059(4) -0.027(3) -0.023(4) 0.005(3)
C35 0.084(6) 0.084(6) 0.057(4) -0.028(4) -0.001(4) 0.010(4)
C36 0.018(2) 0.033(3) 0.047(3) -0.018(2) -0.001(2) 0.000(2)
C37 0.023(3) 0.026(3) 0.050(3) -0.011(2) -0.009(2) -0.001(2)
C38 0.031(3) 0.030(3) 0.049(3) -0.010(2) -0.006(2) -0.007(2)
C39 0.048(4) 0.032(3) 0.062(3) -0.026(3) 0.000(3) -0.018(3)
C40 0.031(3) 0.036(3) 0.040(3) -0.015(2) -0.006(2) -0.007(2)
C41 0.029(3) 0.036(3) 0.036(2) -0.016(2) -0.009(2) -0.002(2)
C42 0.049(4) 0.043(3) 0.048(3) -0.029(3) -0.008(3) 0.003(3)
C43 0.038(3) 0.039(3) 0.038(3) -0.016(2) -0.005(2) -0.006(2)
C44 0.046(4) 0.037(3) 0.063(3) -0.024(3) -0.008(3) -0.004(3)
C45 0.032(3) 0.057(4) 0.041(3) -0.026(3) 0.000(2) -0.002(3)
C46 0.034(3) 0.047(4) 0.060(3) -0.029(3) 0.002(3) -0.010(3)
C47 0.047(4) 0.081(5) 0.097(5) -0.060(4) -0.018(4) 0.014(3)
C48 0.026(3) 0.023(3) 0.057(3) -0.022(2) -0.004(3) 0.000(2)
C49 0.029(3) 0.027(3) 0.049(3) -0.008(2) 0.001(2) -0.005(2)
C50 0.028(3) 0.029(3) 0.052(3) -0.008(2) -0.007(2) -0.005(2)
C51 0.045(3) 0.034(3) 0.060(3) -0.014(3) -0.015(3) -0.006(3)
C52 0.071(5) 0.047(4) 0.047(3) -0.017(3) 0.010(3) -0.021(3)
C53 0.056(4) 0.029(3) 0.068(4) -0.010(3) -0.006(3) 0.004(3)
C54 0.058(4) 0.043(4) 0.062(3) -0.021(3) -0.006(3) -0.001(3)
C55 0.067(4) 0.042(4) 0.057(3) 0.000(3) -0.027(3) -0.011(3)
C56 0.056(4) 0.038(4) 0.085(4) 0.007(3) -0.028(4) 0.003(3)
N1 0.062(4) 0.053(3) 0.089(4) -0.043(3) 0.007(3) 0.001(3)
N2 0.015(2) 0.025(2) 0.037(2) -0.0104(17) -0.008(2) 0.0066(18)
N3 0.021(2) 0.023(2) 0.041(2) -0.0142(18) -0.0028(19) -0.0016(17)
N4 0.062(4) 0.065(4) 0.088(4) -0.050(3) 0.021(3) -0.026(3)
N5 0.018(2) 0.038(3) 0.051(3) -0.020(2) -0.003(2) -0.005(2)
N6 0.021(2) 0.027(2) 0.054(2) -0.011(2) -0.001(2) -0.0026(18)
O1 0.0206(18) 0.034(2) 0.0428(17) -0.0122(15) -0.0022(15) -0.0012(14)
O2 0.0189(18) 0.0320(19) 0.0405(17) -0.0114(15) -0.0063(15) 0.0020(14)
O3 0.048(3) 0.070(3) 0.0386(19) -0.010(2) 0.0051(19) -0.007(2)
O4 0.0184(19) 0.047(2) 0.063(2) -0.0249(19) -0.0011(17) -0.0044(16)
O5 0.0225(19) 0.042(2) 0.055(2) -0.0219(17) -0.0079(16) -0.0048(16)
O6 0.048(3) 0.059(3) 0.078(3) -0.043(2) -0.005(2) 0.006(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
C1 C2 1.374(7) . ?
C1 C3 1.378(6) . ?
C1 C7 1.525(7) . ?
C2 C6 1.383(8) . ?
C2 H2 0.9500 . ?
C3 C5 1.388(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.359(9) . ?
C4 C6 1.369(9) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.543(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.458(6) . ?
C8 C9 1.504(6) . ?
C8 C20 1.537(6) . ?
C9 C10 1.329(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.415(8) . ?
C10 H10 0.9500 . ?
C11 N1 1.151(7) . ?
C12 O2 1.249(5) . ?
C12 N2 1.344(6) . ?
C12 C13 1.482(6) . ?
C13 C14 1.364(7) . ?
C13 C16 1.394(7) . ?
C14 C15 1.388(7) . ?
C14 H14 0.9500 . ?
C15 C18 1.380(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(7) . ?
C17 H17 0.9500 . ?
C18 O3 1.357(6) . ?
C19 O3 1.425(8) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O1 1.236(5) . ?
C20 N3 1.324(5) . ?
C21 N3 1.460(6) . ?
C21 C23 1.503(7) . ?
C21 C22 1.526(7) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C25 1.379(7) . ?
C23 C24 1.408(7) . ?
C24 C28 1.379(7) . ?
C24 H24 0.9500 . ?
C25 C27 1.377(8) . ?
C25 H25 0.9500 . ?
C26 C28 1.367(9) . ?
C26 C27 1.378(9) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.502(7) . ?
C29 C36 1.537(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C34 1.365(8) . ?
C30 C31 1.388(7) . ?
C31 C32 1.376(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.364(9) . ?
C32 H32 0.9500 . ?
C33 C35 1.371(10) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(9) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 N5 1.467(6) . ?
C36 C37 1.511(6) . ?
C36 C48 1.550(7) . ?
C37 C38 1.325(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.429(8) . ?
C38 H38 0.9500 . ?
C39 N4 1.137(7) . ?
C40 O5 1.234(6) . ?
C40 N5 1.337(6) . ?
C40 C41 1.502(7) . ?
C41 C46 1.381(7) . ?
C41 C43 1.390(7) . ?
C42 O6 1.360(6) . ?
C42 C44 1.378(8) . ?
C42 C45 1.383(7) . ?
C43 C45 1.384(7) . ?
C43 H43 0.9500 . ?
C44 C46 1.381(8) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 O6 1.441(7) . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 O4 1.233(6) . ?
C48 N6 1.318(6) . ?
C49 N6 1.475(6) . ?
C49 C50 1.499(7) . ?
C49 C52 1.525(7) . ?
C49 H49 1.0000 . ?
C50 C55 1.360(7) . ?
C50 C51 1.406(7) . ?
C51 C54 1.373(8) . ?
C51 H51 0.9500 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 C56 1.335(8) . ?
C53 C54 1.370(8) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
C55 C56 1.390(9) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
N2 H60 0.69(5) . ?
N3 H58 0.82(5) . ?
N5 H57 0.70(5) . ?
N6 H59 1.00(9) . ?
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
C2 C1 C3 118.5(5) . . ?
C2 C1 C7 120.2(4) . . ?
C3 C1 C7 121.3(4) . . ?
C1 C2 C6 120.5(5) . . ?
C1 C2 H2 119.7 . . ?
C6 C2 H2 119.7 . . ?
C1 C3 C5 120.6(5) . . ?
C1 C3 H3 119.7 . . ?
C5 C3 H3 119.7 . . ?
C5 C4 C6 119.3(5) . . ?
C5 C4 H4 120.3 . . ?
C6 C4 H4 120.3 . . ?
C4 C5 C3 120.5(6) . . ?
C4 C5 H5 119.8 . . ?
C3 C5 H5 119.8 . . ?
C4 C6 C2 120.6(6) . . ?
C4 C6 H6 119.7 . . ?
C2 C6 H6 119.7 . . ?
C1 C7 C8 116.0(4) . . ?
C1 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
C1 C7 H7B 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
N2 C8 C9 111.4(3) . . ?
N2 C8 C20 109.8(4) . . ?
C9 C8 C20 109.4(4) . . ?
N2 C8 C7 106.3(4) . . ?
C9 C8 C7 110.5(4) . . ?
C20 C8 C7 109.3(3) . . ?
C10 C9 C8 125.7(5) . . ?
C10 C9 H9 117.1 . . ?
C8 C9 H9 117.1 . . ?
C9 C10 C11 124.0(4) . . ?
C9 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
N1 C11 C10 177.6(7) . . ?
O2 C12 N2 119.7(4) . . ?
O2 C12 C13 121.2(4) . . ?
N2 C12 C13 119.0(4) . . ?
C14 C13 C16 119.1(4) . . ?
C14 C13 C12 119.7(4) . . ?
C16 C13 C12 121.2(4) . . ?
C13 C14 C15 121.4(5) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C18 C15 C14 119.3(5) . . ?
C18 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C13 119.9(5) . . ?
C17 C16 H16 120.1 . . ?
C13 C16 H16 120.1 . . ?
C16 C17 C18 120.5(5) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
O3 C18 C15 124.6(5) . . ?
O3 C18 C17 115.7(5) . . ?
C15 C18 C17 119.7(5) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 N3 122.7(4) . . ?
O1 C20 C8 120.8(4) . . ?
N3 C20 C8 116.4(4) . . ?
N3 C21 C23 110.8(4) . . ?
N3 C21 C22 109.1(4) . . ?
C23 C21 C22 114.0(4) . . ?
N3 C21 H21 107.5 . . ?
C23 C21 H21 107.5 . . ?
C22 C21 H21 107.5 . . ?
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 . . ?
C25 C23 C24 117.7(4) . . ?
C25 C23 C21 121.8(4) . . ?
C24 C23 C21 120.5(4) . . ?
C28 C24 C23 119.7(5) . . ?
C28 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C27 C25 C23 122.2(6) . . ?
C27 C25 H25 118.9 . . ?
C23 C25 H25 118.9 . . ?
C28 C26 C27 120.0(5) . . ?
C28 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C25 C27 C26 119.2(6) . . ?
C25 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C26 C28 C24 121.1(6) . . ?
C26 C28 H28 119.5 . . ?
C24 C28 H28 119.5 . . ?
C30 C29 C36 114.0(4) . . ?
C30 C29 H29A 108.7 . . ?
C36 C29 H29A 108.7 . . ?
C30 C29 H29B 108.7 . . ?
C36 C29 H29B 108.7 . . ?
H29A C29 H29B 107.6 . . ?
C34 C30 C31 117.4(5) . . ?
C34 C30 C29 121.8(5) . . ?
C31 C30 C29 120.7(5) . . ?
C32 C31 C30 121.5(6) . . ?
C32 C31 H31 119.2 . . ?
C30 C31 H31 119.2 . . ?
C33 C32 C31 120.0(6) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C35 119.6(6) . . ?
C32 C33 H33 120.2 . . ?
C35 C33 H33 120.2 . . ?
C30 C34 C35 121.5(6) . . ?
C30 C34 H34 119.2 . . ?
C35 C34 H34 119.2 . . ?
C33 C35 C34 119.9(7) . . ?
C33 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
N5 C36 C37 106.5(4) . . ?
N5 C36 C29 111.5(4) . . ?
C37 C36 C29 109.3(4) . . ?
N5 C36 C48 108.8(4) . . ?
C37 C36 C48 111.1(4) . . ?
C29 C36 C48 109.6(4) . . ?
C38 C37 C36 127.3(4) . . ?
C38 C37 H37 116.4 . . ?
C36 C37 H37 116.4 . . ?
C37 C38 C39 125.1(4) . . ?
C37 C38 H38 117.4 . . ?
C39 C38 H38 117.4 . . ?
N4 C39 C38 177.2(5) . . ?
O5 C40 N5 122.7(5) . . ?
O5 C40 C41 120.6(4) . . ?
N5 C40 C41 116.6(4) . . ?
C46 C41 C43 118.6(5) . . ?
C46 C41 C40 118.7(5) . . ?
C43 C41 C40 122.7(4) . . ?
O6 C42 C44 115.2(5) . . ?
O6 C42 C45 125.0(5) . . ?
C44 C42 C45 119.8(5) . . ?
C45 C43 C41 120.7(5) . . ?
C45 C43 H43 119.6 . . ?
C41 C43 H43 119.6 . . ?
C42 C44 C46 120.1(5) . . ?
C42 C44 H44 119.9 . . ?
C46 C44 H44 119.9 . . ?
C42 C45 C43 119.7(5) . . ?
C42 C45 H45 120.1 . . ?
C43 C45 H45 120.1 . . ?
C41 C46 C44 120.9(5) . . ?
C41 C46 H46 119.6 . . ?
C44 C46 H46 119.6 . . ?
O6 C47 H47A 109.5 . . ?
O6 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
O6 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
O4 C48 N6 123.0(5) . . ?
O4 C48 C36 121.7(5) . . ?
N6 C48 C36 115.3(4) . . ?
N6 C49 C50 108.2(4) . . ?
N6 C49 C52 110.0(4) . . ?
C50 C49 C52 115.2(5) . . ?
N6 C49 H49 107.7 . . ?
C50 C49 H49 107.7 . . ?
C52 C49 H49 107.7 . . ?
C55 C50 C51 116.7(5) . . ?
C55 C50 C49 125.9(5) . . ?
C51 C50 C49 117.3(5) . . ?
C54 C51 C50 121.5(5) . . ?
C54 C51 H51 119.2 . . ?
C50 C51 H51 119.2 . . ?
C49 C52 H52A 109.5 . . ?
C49 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C49 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C56 C53 C54 119.7(6) . . ?
C56 C53 H53 120.2 . . ?
C54 C53 H53 120.2 . . ?
C53 C54 C51 119.6(5) . . ?
C53 C54 H54 120.2 . . ?
C51 C54 H54 120.2 . . ?
C50 C55 C56 121.0(5) . . ?
C50 C55 H55 119.5 . . ?
C56 C55 H55 119.5 . . ?
C53 C56 C55 121.3(6) . . ?
C53 C56 H56 119.4 . . ?
C55 C56 H56 119.4 . . ?
C12 N2 C8 121.6(4) . . ?
C12 N2 H60 116(4) . . ?
C8 N2 H60 122(4) . . ?
C20 N3 C21 122.4(4) . . ?
C20 N3 H58 113(3) . . ?
C21 N3 H58 124(3) . . ?
C40 N5 C36 122.9(5) . . ?
C40 N5 H57 119(4) . . ?
C36 N5 H57 118(4) . . ?
C48 N6 C49 124.6(4) . . ?
C48 N6 H59 126(5) . . ?
C49 N6 H59 110(5) . . ?
C18 O3 C19 118.2(5) . . ?
C42 O6 C47 117.8(5) . . ?
_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full        28.46
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.087


data_9
_database_code_depnum_ccdc_archive 'CCDC 911536'
#TrackingRef '9.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H28 N2 O4'
_chemical_formula_weight         456.52
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_H-M   P2(1)2(1)2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a                   11.118(3)
_cell_length_b                   16.129(5)
_cell_length_c                   26.837(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4813(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3161
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      20.08
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1936
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.9589
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      153(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36807
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_sigmaI/netI    0.0992
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         28.49
_reflns_number_total             12079
_reflns_number_gt                7698
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 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^)+(0.0841P)^2^+1.5998P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.1(15)
_refine_ls_number_reflns         12079
_refine_ls_number_parameters     633
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.0911
_refine_ls_wR_factor_ref         0.2129
_refine_ls_wR_factor_gt          0.1854
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7564(3) 0.7569(2) 0.82947(12) 0.0252(7) Uani 1 1 d . . .
C2 C 0.6284(3) 0.7856(2) 0.81665(13) 0.0241(7) Uani 1 1 d . . .
C3 C 0.4809(3) 0.8147(2) 0.75040(13) 0.0282(8) Uani 1 1 d . . .
H3 H 0.4237 0.8177 0.7791 0.034 Uiso 1 1 calc R . .
C4 C 0.4263(4) 0.7594(3) 0.71135(15) 0.0368(9) Uani 1 1 d . . .
H4A H 0.4081 0.7052 0.7260 0.055 Uiso 1 1 calc R . .
H4B H 0.4832 0.7525 0.6838 0.055 Uiso 1 1 calc R . .
H4C H 0.3520 0.7846 0.6988 0.055 Uiso 1 1 calc R . .
C5 C 0.5019(3) 0.9018(2) 0.73168(13) 0.0304(8) Uani 1 1 d . . .
C6 C 0.5726(4) 0.9161(3) 0.69024(14) 0.0360(9) Uani 1 1 d . . .
H6 H 0.6076 0.8708 0.6728 0.043 Uiso 1 1 calc R . .
C7 C 0.5926(4) 0.9967(3) 0.67417(19) 0.0518(12) Uani 1 1 d . . .
H7 H 0.6420 1.0069 0.6459 0.062 Uiso 1 1 calc R . .
C8 C 0.5405(5) 1.0620(3) 0.6994(2) 0.0592(14) Uani 1 1 d . . .
H8 H 0.5539 1.1172 0.6884 0.071 Uiso 1 1 calc R . .
C9 C 0.4703(4) 1.0479(3) 0.7398(2) 0.0532(13) Uani 1 1 d . . .
H9 H 0.4343 1.0932 0.7568 0.064 Uiso 1 1 calc R . .
C10 C 0.4508(4) 0.9684(3) 0.75614(16) 0.0412(10) Uani 1 1 d . . .
H10 H 0.4017 0.9591 0.7846 0.049 Uiso 1 1 calc R . .
C11 C 0.8554(4) 0.7382(3) 0.91175(16) 0.0395(10) Uani 1 1 d . . .
C12 C 0.8407(4) 0.7486(3) 0.96734(15) 0.0417(10) Uani 1 1 d . . .
C13 C 0.7597(7) 0.7941(5) 0.9884(2) 0.105(3) Uani 1 1 d . . .
H13 H 0.7056 0.8251 0.9682 0.126 Uiso 1 1 calc R . .
C14 C 0.7501(9) 0.7986(6) 1.0407(2) 0.141(4) Uani 1 1 d . . .
H14 H 0.6866 0.8297 1.0552 0.169 Uiso 1 1 calc R . .
C15 C 0.8271(7) 0.7606(4) 1.06969(19) 0.0756(18) Uani 1 1 d . . .
H15 H 0.8201 0.7640 1.1049 0.091 Uiso 1 1 calc R . .
C16 C 0.9141(7) 0.7178(4) 1.0491(2) 0.083(2) Uani 1 1 d . . .
H16 H 0.9724 0.6913 1.0694 0.100 Uiso 1 1 calc R . .
C17 C 0.9210(6) 0.7113(4) 0.9976(2) 0.082(2) Uani 1 1 d . . .
H17 H 0.9842 0.6796 0.9833 0.098 Uiso 1 1 calc R . .
C18 C 0.8501(4) 0.8186(2) 0.80820(14) 0.0315(8) Uani 1 1 d . . .
H18A H 0.9317 0.7962 0.8143 0.038 Uiso 1 1 calc R . .
H18B H 0.8388 0.8225 0.7717 0.038 Uiso 1 1 calc R . .
C19 C 0.8432(3) 0.9043(3) 0.82996(14) 0.0328(9) Uani 1 1 d . . .
C20 C 0.7684(4) 0.9635(3) 0.80989(17) 0.0431(10) Uani 1 1 d . . .
H20 H 0.7208 0.9502 0.7816 0.052 Uiso 1 1 calc R . .
C21 C 0.7617(5) 1.0418(3) 0.8303(2) 0.0540(13) Uani 1 1 d . . .
H21 H 0.7085 1.0818 0.8165 0.065 Uiso 1 1 calc R . .
C22 C 0.8322(5) 1.0617(3) 0.8706(2) 0.0580(15) Uani 1 1 d . . .
H22 H 0.8293 1.1160 0.8842 0.070 Uiso 1 1 calc R . .
C23 C 0.9070(5) 1.0032(3) 0.89114(18) 0.0535(13) Uani 1 1 d . . .
H23 H 0.9541 1.0168 0.9195 0.064 Uiso 1 1 calc R . .
C24 C 0.9140(4) 0.9254(3) 0.87086(15) 0.0421(10) Uani 1 1 d . . .
H24 H 0.9674 0.8856 0.8847 0.050 Uiso 1 1 calc R . .
C25 C 0.7810(3) 0.6728(2) 0.80688(13) 0.0278(8) Uani 1 1 d . . .
H25 H 0.7999 0.6713 0.7724 0.033 Uiso 1 1 calc R . .
C26 C 0.7786(4) 0.6020(3) 0.83053(14) 0.0331(9) Uani 1 1 d . . .
H26 H 0.7546 0.6016 0.8645 0.040 Uiso 1 1 calc R . .
C27 C 0.8114(4) 0.5229(3) 0.80700(16) 0.0344(9) Uani 1 1 d . . .
C28 C 0.8833(5) 0.4545(3) 0.7361(2) 0.0609(14) Uani 1 1 d . . .
H28A H 0.8264 0.4088 0.7409 0.091 Uiso 1 1 calc R . .
H28B H 0.9606 0.4401 0.7514 0.091 Uiso 1 1 calc R . .
H28C H 0.8948 0.4641 0.7003 0.091 Uiso 1 1 calc R . .
C29 C 1.0221(3) 0.2867(2) 0.86779(13) 0.0302(8) Uani 1 1 d . . .
C30 C 0.9297(4) 0.2811(2) 0.91280(14) 0.0318(9) Uani 1 1 d . . .
C31 C 0.7479(4) 0.3339(3) 0.95194(14) 0.0361(10) Uani 1 1 d . . .
H31 H 0.7899 0.3182 0.9835 0.043 Uiso 1 1 calc R . .
C32 C 0.6542(5) 0.2683(3) 0.9419(2) 0.0629(15) Uani 1 1 d . . .
H32A H 0.6934 0.2141 0.9390 0.094 Uiso 1 1 calc R . .
H32B H 0.6120 0.2812 0.9108 0.094 Uiso 1 1 calc R . .
H32C H 0.5964 0.2670 0.9695 0.094 Uiso 1 1 calc R . .
C33 C 0.6979(3) 0.4193(3) 0.95928(14) 0.0332(9) Uani 1 1 d . . .
C34 C 0.7392(6) 0.4685(3) 0.9962(2) 0.077(2) Uani 1 1 d . . .
H34 H 0.8013 0.4492 1.0176 0.092 Uiso 1 1 calc R . .
C35 C 0.6911(7) 0.5476(4) 1.0032(3) 0.096(3) Uani 1 1 d . . .
H35 H 0.7231 0.5815 1.0289 0.115 Uiso 1 1 calc R . .
C36 C 0.6034(5) 0.5768(3) 0.97564(18) 0.0570(14) Uani 1 1 d . . .
H36 H 0.5672 0.6287 0.9829 0.068 Uiso 1 1 calc R . .
C37 C 0.5668(6) 0.5316(4) 0.9373(3) 0.098(3) Uani 1 1 d . . .
H37 H 0.5080 0.5535 0.9153 0.118 Uiso 1 1 calc R . .
C38 C 0.6126(6) 0.4532(4) 0.9288(3) 0.096(3) Uani 1 1 d . . .
H38 H 0.5841 0.4222 0.9011 0.116 Uiso 1 1 calc R . .
C39 C 1.2105(4) 0.2083(3) 0.85330(14) 0.0334(9) Uani 1 1 d . . .
C40 C 1.2830(4) 0.1357(3) 0.87114(16) 0.0472(12) Uani 1 1 d . . .
C41 C 1.2322(6) 0.0553(3) 0.8698(2) 0.0600(14) Uani 1 1 d . . .
H41 H 1.1496 0.0475 0.8620 0.072 Uiso 1 1 calc R . .
C42 C 1.3064(7) -0.0121(4) 0.8802(2) 0.079(2) Uani 1 1 d . . .
H42 H 1.2752 -0.0670 0.8800 0.095 Uiso 1 1 calc R . .
C43 C 1.4238(6) 0.0020(5) 0.8906(2) 0.081(2) Uani 1 1 d . . .
H43 H 1.4754 -0.0445 0.8945 0.098 Uiso 1 1 calc R . .
C44 C 1.4694(6) 0.0749(5) 0.8954(3) 0.089(2) Uani 1 1 d . . .
H44 H 1.5497 0.0823 0.9066 0.107 Uiso 1 1 calc R . .
C45 C 1.3961(5) 0.1439(4) 0.8833(2) 0.0715(17) Uani 1 1 d . . .
H45 H 1.4302 0.1978 0.8842 0.086 Uiso 1 1 calc R . .
C46 C 1.0780(4) 0.3747(2) 0.86555(13) 0.0290(8) Uani 1 1 d . . .
H46A H 1.1445 0.3740 0.8410 0.035 Uiso 1 1 calc R . .
H46B H 1.0161 0.4136 0.8530 0.035 Uiso 1 1 calc R . .
C47 C 1.1257(4) 0.4077(2) 0.91411(14) 0.0327(9) Uani 1 1 d . . .
C48 C 1.0616(5) 0.4682(3) 0.93943(16) 0.0495(12) Uani 1 1 d . . .
H48 H 0.9883 0.4884 0.9258 0.059 Uiso 1 1 calc R . .
C49 C 1.1030(6) 0.4996(4) 0.9842(2) 0.0740(18) Uani 1 1 d . . .
H49 H 1.0566 0.5390 1.0022 0.089 Uiso 1 1 calc R . .
C50 C 1.2119(7) 0.4732(4) 1.0025(2) 0.091(2) Uani 1 1 d . . .
H50 H 1.2427 0.4966 1.0324 0.109 Uiso 1 1 calc R . .
C51 C 1.2761(6) 0.4136(4) 0.9782(2) 0.0788(19) Uani 1 1 d . . .
H51 H 1.3501 0.3945 0.9917 0.095 Uiso 1 1 calc R . .
C52 C 1.2334(5) 0.3809(3) 0.93370(19) 0.0578(13) Uani 1 1 d . . .
H52 H 1.2787 0.3397 0.9167 0.069 Uiso 1 1 calc R . .
C53 C 0.9548(3) 0.2697(2) 0.81998(13) 0.0309(8) Uani 1 1 d . . .
H53 H 0.9001 0.3112 0.8091 0.037 Uiso 1 1 calc R . .
C54 C 0.9641(4) 0.2036(2) 0.79204(15) 0.0349(9) Uani 1 1 d . . .
H54 H 1.0152 0.1596 0.8023 0.042 Uiso 1 1 calc R . .
C55 C 0.8964(4) 0.1960(3) 0.74461(15) 0.0369(10) Uani 1 1 d . . .
C56 C 0.8662(5) 0.1110(4) 0.67458(19) 0.0645(15) Uani 1 1 d . . .
H56A H 0.9063 0.1455 0.6495 0.097 Uiso 1 1 calc R . .
H56B H 0.7809 0.1259 0.6763 0.097 Uiso 1 1 calc R . .
H56C H 0.8739 0.0524 0.6653 0.097 Uiso 1 1 calc R . .
H57 H 1.090(3) 0.195(2) 0.9026(13) 0.012(9) Uiso 1 1 d . . .
H58 H 0.835(4) 0.367(3) 0.8917(16) 0.035(13) Uiso 1 1 d . . .
N1 N 0.7588(3) 0.7548(2) 0.88379(11) 0.0295(7) Uani 1 1 d . . .
N2 N 0.5952(3) 0.7797(2) 0.76886(11) 0.0267(7) Uani 1 1 d . . .
N3 N 1.1098(3) 0.2233(2) 0.87900(12) 0.0343(8) Uani 1 1 d . . .
N4 N 0.8388(3) 0.3339(2) 0.91204(13) 0.0317(8) Uani 1 1 d . . .
O1 O 0.5623(2) 0.81270(18) 0.84899(9) 0.0365(7) Uani 1 1 d . . .
O2 O 0.9516(3) 0.7157(2) 0.89434(11) 0.0557(9) Uani 1 1 d . . .
O3 O 0.8171(3) 0.45852(18) 0.83015(11) 0.0480(8) Uani 1 1 d . . .
O4 O 0.8367(3) 0.52836(17) 0.75894(10) 0.0402(7) Uani 1 1 d . . .
O5 O 0.9449(3) 0.22909(18) 0.94508(9) 0.0391(7) Uani 1 1 d . . .
O6 O 1.2428(2) 0.24799(17) 0.81693(10) 0.0357(6) Uani 1 1 d . . .
O7 O 0.8313(3) 0.2470(2) 0.72756(12) 0.0510(8) Uani 1 1 d . . .
O8 O 0.9216(3) 0.12429(19) 0.72253(12) 0.0504(8) Uani 1 1 d . . .
H59 H 0.696(4) 0.771(3) 0.8972(15) 0.032(12) Uiso 1 1 d . . .
H60 H 0.641(4) 0.768(3) 0.7501(15) 0.032(12) Uiso 1 1 d . . .
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
C1 0.0337(18) 0.0234(18) 0.0185(15) -0.0012(15) 0.0009(15) -0.0001(16)
C2 0.0310(18) 0.0162(17) 0.0252(17) 0.0062(15) 0.0048(15) 0.0024(15)
C3 0.0259(18) 0.036(2) 0.0229(17) 0.0010(16) 0.0036(15) 0.0048(17)
C4 0.034(2) 0.035(2) 0.042(2) 0.0023(19) -0.0065(18) -0.0014(19)
C5 0.0287(18) 0.033(2) 0.0293(19) -0.0020(17) -0.0082(16) 0.0078(17)
C6 0.044(2) 0.031(2) 0.033(2) 0.0003(18) -0.0019(18) 0.0026(19)
C7 0.054(3) 0.044(3) 0.057(3) 0.010(2) -0.004(2) -0.007(2)
C8 0.063(3) 0.022(2) 0.093(4) 0.008(3) -0.016(3) 0.004(2)
C9 0.048(3) 0.037(3) 0.075(3) -0.013(3) -0.008(3) 0.011(2)
C10 0.034(2) 0.046(3) 0.044(2) -0.007(2) -0.0057(18) 0.015(2)
C11 0.047(2) 0.034(2) 0.038(2) 0.0028(19) -0.011(2) 0.006(2)
C12 0.059(3) 0.032(2) 0.035(2) 0.0031(19) -0.015(2) 0.005(2)
C13 0.135(6) 0.146(7) 0.035(3) -0.025(4) -0.032(3) 0.093(6)
C14 0.183(8) 0.199(9) 0.040(3) -0.039(5) -0.035(4) 0.132(8)
C15 0.117(5) 0.078(4) 0.033(3) -0.009(3) -0.015(3) 0.012(4)
C16 0.111(5) 0.092(5) 0.046(3) 0.025(3) -0.040(3) 0.001(4)
C17 0.085(4) 0.110(5) 0.050(3) 0.011(3) -0.019(3) 0.027(4)
C18 0.034(2) 0.030(2) 0.0305(19) -0.0036(17) 0.0035(16) 0.0046(18)
C19 0.0316(19) 0.039(2) 0.0275(19) -0.0048(18) 0.0108(16) -0.0061(19)
C20 0.048(3) 0.032(2) 0.049(3) 0.001(2) 0.007(2) -0.003(2)
C21 0.058(3) 0.036(3) 0.068(3) -0.003(2) 0.015(3) -0.010(2)
C22 0.074(4) 0.037(3) 0.063(3) -0.018(3) 0.032(3) -0.025(3)
C23 0.059(3) 0.063(3) 0.039(2) -0.016(2) 0.011(2) -0.026(3)
C24 0.041(2) 0.051(3) 0.034(2) -0.006(2) 0.0041(19) -0.009(2)
C25 0.0284(19) 0.030(2) 0.0246(17) -0.0021(16) 0.0000(15) 0.0059(16)
C26 0.038(2) 0.034(2) 0.0271(19) 0.0015(18) 0.0031(17) 0.0027(18)
C27 0.033(2) 0.026(2) 0.044(2) 0.0039(19) -0.0045(18) 0.0062(17)
C28 0.080(4) 0.043(3) 0.060(3) -0.004(3) 0.013(3) 0.025(3)
C29 0.036(2) 0.027(2) 0.0277(18) 0.0082(16) 0.0090(16) 0.0034(17)
C30 0.039(2) 0.028(2) 0.0284(18) -0.0017(17) 0.0088(17) -0.0073(18)
C31 0.045(2) 0.043(2) 0.0205(17) -0.0056(17) 0.0079(17) 0.006(2)
C32 0.056(3) 0.055(3) 0.078(4) -0.008(3) 0.030(3) -0.014(3)
C33 0.034(2) 0.042(2) 0.0232(18) -0.0008(18) 0.0007(16) 0.0042(19)
C34 0.101(5) 0.047(3) 0.083(4) -0.011(3) -0.060(4) 0.015(3)
C35 0.141(6) 0.045(4) 0.101(5) -0.032(3) -0.066(5) 0.018(4)
C36 0.079(4) 0.044(3) 0.048(3) -0.007(2) 0.003(3) 0.013(3)
C37 0.098(5) 0.094(5) 0.102(5) -0.036(4) -0.053(4) 0.059(4)
C38 0.107(5) 0.094(5) 0.088(4) -0.054(4) -0.057(4) 0.058(4)
C39 0.042(2) 0.031(2) 0.0274(19) 0.0024(17) 0.0042(17) -0.0013(18)
C40 0.046(3) 0.061(3) 0.035(2) 0.019(2) 0.012(2) 0.014(2)
C41 0.075(4) 0.041(3) 0.064(3) -0.005(3) -0.014(3) 0.009(3)
C42 0.126(6) 0.046(3) 0.067(4) -0.003(3) -0.014(4) 0.017(4)
C43 0.069(4) 0.099(6) 0.077(4) -0.013(4) -0.006(3) 0.046(4)
C44 0.050(3) 0.089(5) 0.128(6) 0.035(5) 0.016(4) 0.020(4)
C45 0.052(3) 0.080(4) 0.082(4) 0.041(3) 0.001(3) 0.001(3)
C46 0.036(2) 0.026(2) 0.0253(18) 0.0063(16) 0.0013(16) -0.0036(17)
C47 0.043(2) 0.028(2) 0.0272(19) 0.0090(17) -0.0039(17) -0.0051(18)
C48 0.070(3) 0.034(2) 0.045(2) -0.008(2) -0.021(2) 0.004(2)
C49 0.114(5) 0.058(4) 0.050(3) -0.017(3) -0.027(3) 0.012(4)
C50 0.133(6) 0.069(4) 0.071(4) -0.018(4) -0.061(4) 0.008(4)
C51 0.098(5) 0.074(4) 0.065(4) 0.008(3) -0.052(4) 0.008(4)
C52 0.060(3) 0.057(3) 0.057(3) 0.003(3) -0.017(3) 0.003(3)
C53 0.038(2) 0.026(2) 0.0290(19) 0.0012(16) 0.0055(16) 0.0013(17)
C54 0.036(2) 0.027(2) 0.042(2) 0.0051(18) 0.0070(18) -0.0005(18)
C55 0.034(2) 0.033(2) 0.044(2) -0.006(2) 0.0119(19) -0.0060(19)
C56 0.066(3) 0.068(4) 0.060(3) -0.036(3) 0.006(3) -0.020(3)
N1 0.0342(18) 0.0305(18) 0.0238(15) 0.0019(14) -0.0024(14) 0.0010(15)
N2 0.0275(16) 0.0312(18) 0.0215(15) -0.0011(14) 0.0080(13) 0.0090(14)
N3 0.0435(19) 0.0343(19) 0.0252(16) 0.0143(15) 0.0118(15) 0.0047(16)
N4 0.0370(18) 0.0318(19) 0.0262(17) 0.0069(16) 0.0083(15) 0.0048(16)
O1 0.0395(15) 0.0496(18) 0.0204(12) 0.0024(12) 0.0070(11) 0.0139(14)
O2 0.0458(18) 0.073(2) 0.0485(18) -0.0047(17) -0.0122(15) 0.0175(18)
O3 0.066(2) 0.0274(16) 0.0502(18) 0.0088(14) -0.0023(16) 0.0132(15)
O4 0.0521(17) 0.0271(15) 0.0414(16) 0.0001(13) 0.0093(14) 0.0129(14)
O5 0.0510(17) 0.0381(17) 0.0283(13) 0.0122(13) 0.0137(13) 0.0051(14)
O6 0.0391(15) 0.0328(15) 0.0353(14) 0.0086(13) 0.0094(12) -0.0047(13)
O7 0.0520(18) 0.0475(19) 0.0534(19) -0.0167(16) -0.0067(16) 0.0084(17)
O8 0.0532(19) 0.0390(17) 0.059(2) -0.0207(15) 0.0064(16) -0.0025(15)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.458(4) . ?
C1 C25 1.511(5) . ?
C1 C2 1.536(5) . ?
C1 C18 1.550(5) . ?
C2 O1 1.218(4) . ?
C2 N2 1.338(4) . ?
C3 N2 1.476(5) . ?
C3 C4 1.503(5) . ?
C3 C5 1.510(6) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.381(5) . ?
C5 C6 1.382(5) . ?
C6 C7 1.388(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.354(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 O2 1.223(5) . ?
C11 N1 1.337(5) . ?
C11 C12 1.510(6) . ?
C12 C13 1.292(7) . ?
C12 C17 1.348(7) . ?
C13 C14 1.411(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.308(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.310(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(8) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.502(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.375(6) . ?
C19 C24 1.393(6) . ?
C20 C21 1.378(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.372(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.370(7) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.307(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.468(6) . ?
C26 H26 0.9500 . ?
C27 O3 1.212(5) . ?
C27 O4 1.323(5) . ?
C28 O4 1.437(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 N3 1.444(5) . ?
C29 C53 1.511(5) . ?
C29 C46 1.551(5) . ?
C29 C30 1.588(5) . ?
C30 O5 1.218(5) . ?
C30 N4 1.322(5) . ?
C31 N4 1.473(5) . ?
C31 C33 1.498(6) . ?
C31 C32 1.508(7) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.351(6) . ?
C33 C38 1.366(7) . ?
C34 C35 1.395(8) . ?
C34 H34 0.9500 . ?
C35 C36 1.312(8) . ?
C35 H35 0.9500 . ?
C36 C37 1.324(8) . ?
C36 H36 0.9500 . ?
C37 C38 1.383(8) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 O6 1.221(4) . ?
C39 N3 1.337(5) . ?
C39 C40 1.501(6) . ?
C40 C45 1.306(7) . ?
C40 C41 1.414(7) . ?
C41 C42 1.393(8) . ?
C41 H41 0.9500 . ?
C42 C43 1.354(9) . ?
C42 H42 0.9500 . ?
C43 C44 1.287(9) . ?
C43 H43 0.9500 . ?
C44 C45 1.416(8) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 C47 1.505(5) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C52 1.378(6) . ?
C47 C48 1.387(6) . ?
C48 C49 1.383(6) . ?
C48 H48 0.9500 . ?
C49 C50 1.374(9) . ?
C49 H49 0.9500 . ?
C50 C51 1.363(9) . ?
C50 H50 0.9500 . ?
C51 C52 1.390(7) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 C54 1.307(5) . ?
C53 H53 0.9500 . ?
C54 C55 1.484(6) . ?
C54 H54 0.9500 . ?
C55 O7 1.188(5) . ?
C55 O8 1.330(5) . ?
C56 O8 1.442(6) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
N1 H59 0.83(4) . ?
N2 H60 0.74(4) . ?
N3 H57 0.81(3) . ?
N4 H58 0.77(4) . ?
O3 H58 2.22(5) . ?
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
N1 C1 C25 112.1(3) . . ?
N1 C1 C2 104.3(3) . . ?
C25 C1 C2 110.4(3) . . ?
N1 C1 C18 111.8(3) . . ?
C25 C1 C18 107.9(3) . . ?
C2 C1 C18 110.3(3) . . ?
O1 C2 N2 122.8(3) . . ?
O1 C2 C1 120.5(3) . . ?
N2 C2 C1 116.7(3) . . ?
N2 C3 C4 110.8(3) . . ?
N2 C3 C5 109.5(3) . . ?
C4 C3 C5 112.4(3) . . ?
N2 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C5 C3 H3 108.0 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 119.1(4) . . ?
C10 C5 C3 120.1(4) . . ?
C6 C5 C3 120.7(3) . . ?
C5 C6 C7 119.9(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 119.7(5) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
O2 C11 N1 123.2(4) . . ?
O2 C11 C12 120.3(4) . . ?
N1 C11 C12 116.5(4) . . ?
C13 C12 C17 116.9(5) . . ?
C13 C12 C11 124.7(4) . . ?
C17 C12 C11 118.3(5) . . ?
C12 C13 C14 121.1(6) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 121.3(6) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 118.6(5) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C17 120.1(6) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 121.9(6) . . ?
C12 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C19 C18 C1 114.4(3) . . ?
C19 C18 H18A 108.7 . . ?
C1 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C1 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C24 118.7(4) . . ?
C20 C19 C18 121.2(4) . . ?
C24 C19 C18 120.1(4) . . ?
C19 C20 C21 120.9(5) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 119.7(5) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C21 120.1(5) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.3(5) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C19 120.3(5) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C26 C25 C1 125.9(3) . . ?
C26 C25 H25 117.1 . . ?
C1 C25 H25 117.1 . . ?
C25 C26 C27 123.0(4) . . ?
C25 C26 H26 118.5 . . ?
C27 C26 H26 118.5 . . ?
O3 C27 O4 123.0(4) . . ?
O3 C27 C26 122.5(4) . . ?
O4 C27 C26 114.5(3) . . ?
O4 C28 H28A 109.5 . . ?
O4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 C53 112.5(3) . . ?
N3 C29 C46 112.7(3) . . ?
C53 C29 C46 109.4(3) . . ?
N3 C29 C30 103.8(3) . . ?
C53 C29 C30 108.4(3) . . ?
C46 C29 C30 109.9(3) . . ?
O5 C30 N4 124.1(4) . . ?
O5 C30 C29 119.4(3) . . ?
N4 C30 C29 116.5(3) . . ?
N4 C31 C33 110.5(3) . . ?
N4 C31 C32 110.2(3) . . ?
C33 C31 C32 114.4(4) . . ?
N4 C31 H31 107.2 . . ?
C33 C31 H31 107.2 . . ?
C32 C31 H31 107.2 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C38 116.1(5) . . ?
C34 C33 C31 120.7(4) . . ?
C38 C33 C31 123.1(4) . . ?
C33 C34 C35 120.4(5) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C36 C35 C34 122.5(5) . . ?
C36 C35 H35 118.8 . . ?
C34 C35 H35 118.8 . . ?
C35 C36 C37 118.0(5) . . ?
C35 C36 H36 121.0 . . ?
C37 C36 H36 121.0 . . ?
C36 C37 C38 121.2(5) . . ?
C36 C37 H37 119.4 . . ?
C38 C37 H37 119.4 . . ?
C33 C38 C37 121.6(5) . . ?
C33 C38 H38 119.2 . . ?
C37 C38 H38 119.2 . . ?
O6 C39 N3 124.4(4) . . ?
O6 C39 C40 120.4(4) . . ?
N3 C39 C40 115.2(3) . . ?
C45 C40 C41 118.9(5) . . ?
C45 C40 C39 121.2(5) . . ?
C41 C40 C39 119.5(4) . . ?
C42 C41 C40 118.3(5) . . ?
C42 C41 H41 120.9 . . ?
C40 C41 H41 120.9 . . ?
C43 C42 C41 118.8(6) . . ?
C43 C42 H42 120.6 . . ?
C41 C42 H42 120.6 . . ?
C44 C43 C42 123.6(6) . . ?
C44 C43 H43 118.2 . . ?
C42 C43 H43 118.2 . . ?
C43 C44 C45 117.9(6) . . ?
C43 C44 H44 121.0 . . ?
C45 C44 H44 121.0 . . ?
C40 C45 C44 122.2(6) . . ?
C40 C45 H45 118.9 . . ?
C44 C45 H45 118.9 . . ?
C47 C46 C29 115.6(3) . . ?
C47 C46 H46A 108.4 . . ?
C29 C46 H46A 108.4 . . ?
C47 C46 H46B 108.4 . . ?
C29 C46 H46B 108.4 . . ?
H46A C46 H46B 107.4 . . ?
C52 C47 C48 118.8(4) . . ?
C52 C47 C46 121.7(4) . . ?
C48 C47 C46 119.5(4) . . ?
C49 C48 C47 120.8(5) . . ?
C49 C48 H48 119.6 . . ?
C47 C48 H48 119.6 . . ?
C50 C49 C48 119.4(6) . . ?
C50 C49 H49 120.3 . . ?
C48 C49 H49 120.3 . . ?
C51 C50 C49 120.6(5) . . ?
C51 C50 H50 119.7 . . ?
C49 C50 H50 119.7 . . ?
C50 C51 C52 120.0(5) . . ?
C50 C51 H51 120.0 . . ?
C52 C51 H51 120.0 . . ?
C47 C52 C51 120.4(5) . . ?
C47 C52 H52 119.8 . . ?
C51 C52 H52 119.8 . . ?
C54 C53 C29 126.6(4) . . ?
C54 C53 H53 116.7 . . ?
C29 C53 H53 116.7 . . ?
C53 C54 C55 121.3(4) . . ?
C53 C54 H54 119.4 . . ?
C55 C54 H54 119.4 . . ?
O7 C55 O8 124.0(4) . . ?
O7 C55 C54 125.6(4) . . ?
O8 C55 C54 110.3(4) . . ?
O8 C56 H56A 109.5 . . ?
O8 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
O8 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C11 N1 C1 125.5(4) . . ?
C11 N1 H59 120(3) . . ?
C1 N1 H59 114(3) . . ?
C2 N2 C3 122.1(3) . . ?
C2 N2 H60 119(3) . . ?
C3 N2 H60 117(3) . . ?
C39 N3 C29 125.8(3) . . ?
C39 N3 H57 122(2) . . ?
C29 N3 H57 112(2) . . ?
C30 N4 C31 120.9(3) . . ?
C30 N4 H58 120(3) . . ?
C31 N4 H58 119(3) . . ?
C27 O3 H58 162.5(11) . . ?
C27 O4 C28 116.0(3) . . ?
C55 O8 C56 115.9(4) . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.49
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.083